High School DxD: ERO!, Chapter 27: Seven Girls, One Date
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It was clear that Gasper didn't want to open up and go out of her room. At the same time, she needed to! I'm sorry, but nobody how much of a cute bishoujo you are, no matter how much I want to protect you, you have to be able to leave your room! If, in the future, Gasper becomes a strong young woman who doesn't claw and wail at the thought of going outside without me, and she still wants to stay inside and goon all day, then I'll happily support her - but that wasn't the situation! There's a big difference between being afraid to leave your room, and enjoying staying in your room!

(I spent a lot of time in my room nowadays, because it was the best place to have sex with your girlfriend, especially because my mom was much more understanding than most moms probably would be... thanks, Mom!)

Gasper could leave her room when I was with her, because she implicitly trusted me to protect her. But I didn't want her to be totally reliant on me either, even if it was cute and gave me a boner!

Thankfully, I had an expert on girls with me.

"Hmm," Tsubasa hummed. "I have never had a hikikomori girlfriend," she said, carefully avoiding saying that she'd never had a girlfriend. "So I do not know for sure what to do... but I think that what would probably be best, is to give her a reason to want to go outdoors. From everything you have said so far, the only reason she is even going out at all is because you are taking her there. Not just in the sense that you are protecting her, but in the sense that you want her to."

Tsubasa really was an incredible and thoughtful partner. However, I had no idea what she meant. "Sorry, I don't understand."

"Imagine that, for some reason, you suddenly became deathly afraid of leaving your room. You would want to leave your room and work to overcome the fear, right? Why? It's because if you don't leave your room, how can you do fun things like go buy a maid outfit for Kiyome, or go on dates, or meet new girls, or spend time with your friends."

"Ah! I see!" I smashed my fist into my palm. "In other words, part of the reason Gasper stays in her room is because she doesn't have any reason to leave!" Tsubasa nodded. "So I need to come up with fun things she can only do outside... we could go to the park." She might not like the park, though. There was the arcade, but you can play video games on your computer! We could go out to eat together, but that was just a date, and it would just be 'me taking her out', rather than 'her wanting to go out'...

"I think it would help if she had many friends outside of her room. Right now, her friends are you and the other members of Rias's peerage," Tsubasa explained.

"Oh! Like a big group date with all my other girlfriends! And it would be unreasonable for them to all come over to visit, so if she wants to see them, then she has to leave!"

"Exactly," Tsubasa agreed. "I've never had a harem, so that wasn't what I was thinking, but it's a very good idea."

"Ah... but a big date for everybody would be really expensive..."

"We can go somewhere cheap, like the park, and you don't have to pay for everything."

"Eh?! No, I do, right? I'm the guy, so I do." Tsubasa only had girlfriends before me. Did lesbians go dutch?

"Issei." She raised one finger. "This is an important lesson about girls I am about to teach you. It is a lesson many men don't understand, and it causes their girlfriends no end of headaches." Wait, their girlfriends? Don't tell me you do NTR, Tsubasa! I don't want a homewrecker girlfriend! "Men think women want a man who is a 'provider,' but really, women want a man who is a 'protector.'"

"...Huh?"

"What makes a woman swoon is when you gently take hold of her hip, moving her from the side of the sidewalk facing the street, to the side away from the street. Even when an expensive date is nice, it is because it is tailor made for her, not because it is expensive. Women don't want a cheapskate, yes, just like men don't want a gold-digger, but if you are asking out a large group of people to spend time with you, it's okay to ask them to spend their own money. Of course, you must be ready for them to say 'no' in that case," she added. Maybe something in my face said I was doubtful, so she continued. "Think about it. When you went out with Gasper and the ORC, did Gasper cling to you because you were paying for her to play video games, or because she felt safe around you?"

Eh? That was true! It was definitely the feeling of safety, I don't have any doubt! But- "Gasper was a boy then, though..."

Tsubasa crinkled her nose at that. "Issei..." Don't look at me so disapprovingly, Tsubasa! What did I do?! "I always thought that Gasper was just a boy who liked crossdressing, but it's obvious she was trans now, isn't it?"

Oh no! Tsubasa thinks Gasper turned into a girl purely because of her own feelings rather than because I said it was a precondition to dating me! Of course from that perspective, it would be horribly rude to say something like that about my girlfriend!

While that wasn't the case, the truth was probably even worse to say out loud-! But Tsubasa was my girlfriend, and I needed to be honest with her. Also, there was no way I could keep it a secret, not with all the ORC knowing about it... "Tsubasa... ah..." I swallowed. I was probably going to lose my cute girlfriend, Tsubasa, who was sweet and earnest and hardworking-! But a relationship based on lies is no good at all! "Gasper... became a girl for me. I'm straight, so I had no interest in her before-! Well, I kind of had an interest in her, but I would never have acted on it, because I'm straight. But I told her as much, and she decided to become a girl!"

Tsubasa just hummed. "In other words, Gasper didn't become a girl because 'she always wanted to,' she became a girl because 'it's the only way to be with Issei'?"

"Yes."

"Hm. Okay then."

"Okay? You're not mad at me for making Gasper become a girl?!"

"Issei, if you want to be my partner, you must become a girl."

"What?! B-but! I'm already your partner."

"Yes, and? You must become a girl to remain my partner."

"Wha... no. I'm sorry! I won't do that! I like being a boy too much!"

"Exactly. See?" Tsubasa said. I just blinked. "Gasper must not have been too attached to her biological sex, to so quickly transition just to be with you. Although, the fact that she has access to an easy sex change device probably helps her along..." She hummed. "I don't like labels too much, myself, so I don't understand why you were so bothered by Gasper being a boy, but if you are both happy, then it's fine."

"Tsubasa! Thank you for being my girlfriend!" I wrapped her in a big hug, and she just smiled and gently patted my back.

* * *

Following Tsubasa's idea, I took Gasper out with a whole bunch of people - Akeno, Aika, Asuka, Rias, Tsubasa, Kiyome... but not Yuma or Azazel. I figured that Gasper would enjoy spending time with people her own age more.

I was a little worried, going out for a picnic like that. Not because I thought my girlfriends would be mad about a nice picnic. (I had a great excuse if they called me a cheapskate, since Asuka is a harpy so she can't just go to the arcade in Kuoh, but nobody did!)

It was because... what if they didn't like each other?! While I had a guarantee they wouldn't be jealous as long as I treated them all well, that didn't mean they'd get along well! I wasn't jealous of Kokabiel at all, and he wasn't jealous of me (probably?), but he still tried to kill me! People can dislike each other for reasons besides jealousy!

Gasper, predictably, clung to me constantly, just plopping herself in my lap as the moment settled down together. She briefly shrieked when Asuka landed, even though I'd told her in advance one of my girlfriends was a harpy. She actually activated her Sacred Gear - Forbidden Balor View - which caused Asuka to freeze mid-landing, her taloned feet clawing at dirt, the puffs of it caught in midair. It looked kinda cool, so I tilted my head from side to side for a couple seconds to look at the dirt, then realized - "Gasper, turn it off!"

"Eep! Sorry!" Gasper shouted, closing her eyes. Asuka finished her landing, not even seeming to realize that anything had gone wrong. "Sorry, Asuka."

"For yelling?" Asuka asked, idly playing with one of her ears with her wing-hand. "It wasn't that loud."

"N-no, I used Forbidden Balor View on you... sorry..."

"What's that?" Asuka asked, peering at me suspiciously. Why are you suspicious of me? Gasper is the one who did it!

"It freezes time," I explained.

"Hm. Isn't that a sex thing?" She reached for her breasts, briefly cupping them and letting them plop down; Gasper's cheeks glowed at the show. "You didn't do anything weird with me while I was frozen?"

"No!" Gasper defended. "Issei wouldn't do something like that, right, Issei?"

"Right," I agreed, gently patting Gasper's head. The girl herself beamed with pride at having defended her boyfriend, which was super cute.

"Hmph." Asuka plopped down at where I'd already laid out the picnic. "Where's everyone else?"

"Ah- I decided to come with just Gasper, but everybody else knows the time and place." Wait! What if they forgot, or stood me up?! I hurriedly pulled out my phone and sent a text to every one of my girlfriends (other than Yuma and Azazel) to make sure they knew where it was!

"Apparently you left Kiyome behind?"

"She can walk, it's not like we're on top of a mountain," Asuka said, picking over the food from the picnic basket. "Ooo, nice," she said, grabbing a bag of potato chips. "I love these." She popped it open, and I suddenly wondered - was Asuka unable to get bags of potato chips on her own?! After all, she was a monstergirl, forbidden from interacting with normal human society... "What are you looking at me like that for?"

Ah! That withering gaze of hers! She had strong tsundere energy, always suspicious of me and my intentions even though they were nothing but pure. I hoped it was just her personality, rather than some horrible trauma, because I don't want any of my girlfriends to have horrible trauma! "I was wondering if you can get potato chips on your own, since you look like that," I explained.

She snorted. "Kiyome buys food for me, don't worry." She started eating the potato chips at that point - though not with her hands, instead wiping one of her talons off with a handkerchief, and then using it to pluck them out. I guess I wouldn't want oil all over my wings either...

Kiyome showed up next, pretty much running to the site, wearing her tennis outfit and looking amazing as her tits bounced in her rush. "Suh, sorry, Issei!" She panted heavily, planting her hands on her knees as she leaned forward, and Gasper's gaze went to exactly the same place mine did: her cleavage, presented through her top, her cheeks warming as she stared.

"It's okay!" I reassured Kiyome. "It's totally fine! You're actually the fourth to arrive, so you're faster than most people!" I patted the spot on the grass next to me, while Asuka gave Kiyome a half-hearted wave.

The rest of the group filtered in - Akeno and Rias together, then Tsubasa about two minutes early, and then Aika about five minutes late. Everybody except Aika and Asuka started treating Gasper like a cute little sister (Asuka was busy munching on potato chips, and Aika was clearly trying to figure out how one guy could fuck seven women at the same time), and Tsubasa in particular seemed to have a keen interest in Gasper's feelings about her recent sex change.

"It's... um... well, I wasn't that attached to being a boy, and Issei makes me happy, so..." Gasper explained in a mumbly, shy voice as she was interrogated.

"I see," Tsubasa said. "If Issei makes you happy, then it's your body, and your choice," she said, smiling softly at Gasper - and then surprising the girl with a hug. "If you ever need any advice on girly things, including biological ones, then you can ask me."

"Ah!" Gasper's eyes widened in surprise. "I- oh, I don't know about periods or other things like that-!"

"Gasper, you don't have a womb," I reassured her. "Azazel didn't add that feature. You can't have a period without a uterus."

"That's true," Tsubasa said, "but there are other things to keep in mind that a boy might not know."

"Such as?" I asked. Tsubasa crinkled her nose at me, as if to say, That isn't your business. "Rias?"

"Hm?" Rias hummed. "Lots of things."

"Aika?"

"What am I, your sex ed teacher? I've studied sex vociferously, as a supposed pervert you should already know all this stuff."

"Guh!" They were ganging up on me, weren't they? "Akeno! You're my sub! That means you have to tell about your womanly secrets!"

"Issei-sama, there are things about womankind that men are better off not knowing," Akeno explained.

"Also, it's kinda messed up to try to use your sub's status against her," Asuka said, slurping on a juice carton as she finished her thought.

I turned to look at Kiyome. "Y-yes, I agree," Kiyome said, flushing, seeming to think I was asking about her opinion on how to treat subs, rather than information on feminine secrets. "Even if someone is a sub, you should ask them things like that instead of ordering them around! Submission is about the mutual joy of domination, not ordering someone around..." Kiyome I'm sure that line makes sense in your head, but it's complete gibberish to any normal person!

Still, everyone was nice to Gasper, even when it became obvious that she was extremely visually-oriented for a girl, and extremely interested in big tits for a girl, which took probably less than half an hour for even the densest person to notice (Asuka, who flew around in a bikini). My worries about the girls fighting and not getting on failed to come to fruition. I should have been worried about them ganging up on me like that! Once a couple of the girls agreed that I shouldn't do something, that basically made it certain the rest would all fall in line! My harem was becoming a cartel!

The picnic did end up mostly being the girls chatting about things like I wasn't there, while Gasper kept her pert butt on my cock, but that was the point. I wanted Gasper to think of all my girlfriends as friends, and think, Boy, I'd like to spend time with Kiyome, but she's playing tennis - what if I want to watch her play tennis, though? and similar things so that she'd stop hiding in her room and start leaving to spend time with her new friends.

"Alright," Aika said, as I started to pack up the picnic. "So how is the orgy going to happen, Issei?"

You might expect everyone to gasp at Aika's inappropriate statement - but the exact opposite happened!

"Yes, as a man with ten girlfriends, you should have a plan on how to please them all in situations like this," Tsubasa agreed.

"I'm such Issei has wonderful, debauched plans for us all," Kiyome said, her certainty in me much greater than I felt!

"Yeah, I don't get fucked enough because I can't live in town," Asuka agreed. "You can't ask me out and then not fuck me. What's the plan, Issei?"

"Don't worry. I have a plan." I... I actually didn't have a plan! "Let's go to Rias's apartment." My apartment was definitely too small to fit seven girls comfortably. Also, Rias's apartment was further away, so I had more time to come up with an idea.

"Ah! I can teleport us there quickly, then, using your magic, Issei-kun," Rias said. No! No!

"Oh, um. I was hoping we could walk, since it's nice to get some open air."

"Asuka will probably have trouble walking all that way," Rias pointed out.

"I can fly," Asuka said, casually bending her legs, clearly contemplating flying into the air. "If you really want to walk."

"Isn't it difficult to walk around with an erection, Issei-kun?" Tsubasa asked curiously, glancing down at my boner. (Gasper did it! Her butt was planted in my lap the whole meal, so of course I got a boner!)

Yes, but-! Akeno spoke up then, chuckling lightly. "Let's let Issei-sama decide what to do. Bullying him is no good."

The girls decided to listen to Akeno, who I silently forgave for every teasing comment she gave throughout the whole meal, for that act of mercy!

* * *

Rias's apartment was actually quite similar to Gasper's room in terms of size, but the important thing was: it was bigger than my room! The unfortunate thing was, I hadn't really come up with any ideas better than 'fuck one girl while fingering two others!' Ah well! I'd just make the sex last a long time!

"First thing's first - everybody get naked."

"Really? That's it?" Aika asked flatly, even as she started to unbutton her blouse. "I thought there'd at least be costumes or bondage or something... I guess you're just too vanilla."

Stop saying things like that, or maybe I'll put you in bondage and make you watch in a cuck chair as I have sex with all my other girlfriends - wait! That's it! "I'd like to try something first. Akeno, can you make me a bullet vibrator? With a remote," I added. She hummed, currently in her underwear, grabbing her phone and fiddling with it before she pressed her hand against me, withdrawing a perfectly functional bullet vibrator - which she promptly shoved into her panties.

"It's nice to know you only practice this sort of thing with me," Akeno said, a sweet smile on her lips. Ah! That was the wonder of having a perverted girlfriend like Akeno! She took things like this as a show of your love!

"Let's try it," I breathed, hitting the button on the remote control, and willing Akeno to come at the same time. She moaned and gasped in response, her hips bucking as she collapsed to her knees in front of me, my dick getting insanely hard - both to Akeno on her knees in front of me in nothing but her underwear, and the fact that I had a way to make sure all my girlfriends were satisfied! "It worked! Make six more, for everybody, but make them all attached to this remote," I ordered Akeno, who just panted heavily.

"Ah, only five, Issei-kun," Tsubasa said, raising her hand. She was naked, but she looked completely proud and undaunted, as natural in the nude as she might have been in a bikini or her normal clothes. "I don't like that sort of thing."

"Huh?" Aika asked in confusion. "You don't like orgasms? He used his orgasm magic to make Akeno come, obviously. He's gonna use it on all of us, since he's only got the one dick."

"Yes, I understand," Tsubasa nodded. "For me, orgasms are something I like to give my partner, not to chase after myself. As long as Issei-kun is satisfied at the end of this sex, then I'll be happy."

"What a weirdo," Aika muttered. No, Aika! Be nice to my girlfriend!

Tsubasa just shrugged. "I have never had complaints that I made a girl feel too good." Wait, you should be saying that about me, Tsubasa! You forgot to say 'I made Issei feel too good'! "Issei hasn't complained either. No, Issei-kun, you've been even nicer than a girl. Some girls feel bad about me making them come, while they don't reciprocate, but you just accept it."

"Wow... a guy who accepts having his dick sucked, and doesn't complain that he doesn't eat you out... he's just chasing his own pleasure, duh," Aika said.

"No! It's because I have magic sex skills, so from the very first time Tsubasa sucked my cock, I knew she didn't want me to make her come! It's different, but Tsubasa is special, and she's my girlfriend, so of course I'll treat her the way she likes."

Tsubasa smiled at that. "That's a good line, Issei-kun. I'll remember it."

"Ready," Akeno said, having recovered and used her phone to prepare the magic. She planted her hand on my chest, and pulled out five more bullet vibrators from it. She then gave them to all my girlfriends present (except Kiyome). "Ah, Gasper, let me show you how to use it," she said, to the fidgeting, blushing Gasper.

I wasn't sure if she was more embarrassed or horny - on the one hand, she was naked in front of a bunch of other girls for the first time, and on the other hand, her eyes were more preoccupied with staring at Rias, Akeno, Kiyome, and Asuka's big tits than checking their faces for any sign of judgment.

Akeno just knelt in front of Gasper, gently placing the bullet vibe against her clit, gently smoothing the tape into place against her pubic mound, and doing the same with the battery against her thigh. When it was done, she gave Gasper a little kiss on the tummy, which made Gasper turn bright red. "There you go, Gasper-chan," she said, giving Gasper a little wink.

At that point, everybody was ready: the girls except for Akeno were naked (Akeno was still just in her underwear), and the girls except for Tsubasa were wearing their vibes now, the remote in my hand. Also, I was naked by that point, my big cock throbbing in the air as I tried to decide who to start with. There were so many girls! Ah! I decided to just use the remote and make everybody come, which they promptly did. Akeno once more dropped to her knees, panting as she leaned forward, while Gasper wound up grabbing onto Akeno's head for balance, lewdly bucking her hips in the air. Rias, Aika, and Asuka managed to remain standing, with Asuka seeming to have the best balance of the three, while Aika swayed in place, knees clacking against each other.

Kiyome just moaned and threw herself towards me. "Oh, Issei," she moaned as she rubbed her tits into my forearm. I guess there was my answer on who to fuck first! I hefted her into the air in a single quick movement, then laid her out on the bed in front of me. "Issei~," she moaned happily, as I just shoved my cock into her waiting pussy, grabbing her thighs and pushing them up, letting me get extra deep inside her. I rolled my hips around in her pussy, making her writhe as her cunt went crazy around my cock.

As I started to fuck Kiyome, Tsubasa approached smoothly, leaning in to kiss my cheek, and then leaning down to kiss Kiyome's as well. "Issei-kun, it's so nice to see you and Kiyome making one another happy like this," she said, with a warm smile on my lips. "Make Kiyome come again, she has the cutest o-face." Kiyome blushed a little, but I made her come! She moaned and cast her head back, and Tsubasa proceeded to get on the bed behind me, softly kissing at my neck as her fingers ran along my chest, just groping me and feeling me up. "Issei-kun, you have so many girlfriends, I'm a little jealous." Jealous?! No, that wasn't possible-! "I've never had more than one girlfriend at a time..." Oh, she meant jealous of me. Whew.

"W-well, if one of my girlfriends wants to do stuff with you, she can," I declared, glancing over at the girls standing off to one side. Akeno was still kneeling and wearing her underwear only, which was dead sexy, her hand on the back of Gasper's head (Gasper having apparently fallen to her knees), holding her to make her watch the scene unfolding in front of her.

"Issei-kun, thank you for being generous. I promise to help you make your girlfriends happy." She nuzzled at my neck, kissing at it, and I could tell she had nothing but the purest feelings when she said that! Well, also she definitely wanted to do sex stuff with my girlfriends. Wait! Had she not done sex stuff with Kiyome yet, purely out of concern for me, despite the way she and Kiyome got on so well?! "The other girls have recovered, give them another orgasm, Issei-kun," she said.

I glanced over at the group again. I pushed the remote button, and willed Gasper to come - which she alone did. Incredible! This sex power was incredible! I held the button down, and in sequence, made Rias, Akeno, Aika, and Asuka all come, waiting a second or two between each, but not removing my fingers from the button at all. It was really amazing to watch them all moaning, and seeing Aika collapse to her hands and knees on the floor... made me want to make Rias do it too! Especially since she had much bigger boobs than Aika!

"Oh, Issei~," Kiyome whined out. "Issei, Tsubasa, look at me~eee," she squealed out the last word as I made her come. I shifted my hands from her thighs, to instead grope her tits, pushing them together and suckling on the nipples. Her body was contorted into a new position, and Tsubasa followed me up, leaning over me to watch me fuck Kiyome hard.

Now that I had Kiyome suitably distracted, I could go back to making sure the rest of my girlfriends were satisfied! I glanced their way, hitting Rias with one orgasm, waiting several seconds before hitting her with a second, sending her collapsing down to the floor, her huge breasts jiggling freely as she landed on hands and knees. Asuka was the only one left standing, panting heavily as she stood there, naked, her arms at either side, large wings subtly fidgeting for balance, her taloned feet straining against the floor... then I decided to knock her over too! It took a half-dozen orgasms before Asuka's superior avian balance was overcome, but she crashed forward with an animalistic squawk, wings hitting the ground as she landed on hands and knees, big tits swaying back and forth.

Kiyome looked about ready to complain about my wandering eye again, so I hit her with a fresh orgasm too. It was exhilarating! Fun, easy, and dead sexy, and I got to fuck Kiyome as I went at it! But there were other girls I wasn't fucking, so I hit Kiyome with a couple fresh orgasms, then pulled out of her pussy, shifting up to plop my dick in between her breasts. I just squished them together around my cock, starting to pump back and forth, admiring Kiyome's cute flushed cheeks, her half-parted lips - and the girl herself soon leaned forward, suckling on my cockhead as she looked up at me for approval.

Then I made her come, and I promptly came myself, spraying hot spunk all over the inside of her mouth. She tried to gulp it down, but some spurted out of her nose and mouth due to the quantity and the fact that she was coming. When she was done with her orgasms, I pulled out of her mouth and tits alike, leaving her panting on the bed as I turned my attention to the group of other girls. As I considered them all... I hit the button on the remote control and made everybody come again! Girls were thrashing and crawling, big tits bouncing, Aika gasping as she looked up at me.

Yeah! Aika going next made sense! I'll teach her to doubt my sex skills! I grabbed her under the arm, just bending her over the bed, letting Tsubasa watch from the sidelines this time as I unceremoniously slammed my cock into her waiting pussy. She moaned and gasped as I pounded away, the bed faintly creaking from the sheer force with which I was going at it. "Fuck me harder," Aika mewled, and I dutifully upped my pace and sent another orgasm through her body. "Ahm, ahn, fucking, huh, harder," she gasped out, and I intensified my pace still further, always willing to grant my girlfriends' wishes! Aika squealed and came without me actively helping her along - and I made her come a third time anyway!

It felt so good! So nice! I just railed away, forgetting about anything else, until Rias came to sit on the bed on one side of Aika, and Asuka sitting on the other, their naked bodies on full display, their tits jiggling a bit as the bed bounced beneath Aika. "Issei, you're way too distractible," Asuka said with a small huff, crossing her arms in a way that hid her tits.

Whatever! I made her come too, and Rias, and I just kept fucking Aika. Whenever Asuka or Rias seemed about to give me some lip, I'd make them come again! And then, when I decided I really wanted to come, I didn't do it inside Aika - instead, I pulled out. "Tsubasa, I want to come in your mouth," I said.

"Ah, if that's what Issei-kun wants, then of course," Tsubasa said, getting down on her knees in front of me, casually wrapping her lips around my cockhead, fluttering her eyelashes up at me. I just ejaculated, spraying all over the inside of her mouth, letting her greedily gulp it all down.

When I was finished in her mouth, I pulled out, looking over to Gasper and Akeno, who were both staring at me with flushed cheeks, my dick throbbing in the air.

They'd been watching the whole time, left unsatisfied... wait! I had a great idea! I grabbed Gasper, throwing her atop Rias, and then slammed my dick into Gasper's pussy - before shoving her face into Rias's boobs! Gasper liked big boobs (a girl of culture, like myself), and now she was being smothered in Rias's! Rias responded by panting, and then starting to gently pet Gasper as the girl came her brains out on my cock (mostly because I was spamming orgasms). I made Akeno orgasm as I fucked Gasper, hitting her with orgasm after orgasm, pleasure racing up her spine as her pussy gripped, squeezed, and oozed all over my cock, moaning and drooling incoherently.

I made Akeno come a whole bunch while I fucked Gasper, not even bothering to glance behind me. Tsubasa watched the whole scene with a smile on her lips, her gaze going from me, to Gasper, to Rias, and occasionally leaning over to kiss Kiyome on the cheek or forehead.

Asuka fidgeted needily, and after I finally blew my load inside of Gasper, I pulled out, had Tsubasa give my cockhead a quick cleaning, and then shoved it in Asuka's waiting harpy pussy! I fucked her with her legs dangling off the edge of the bed, big tits bouncing as I pounded away, her eyes looking up at me half-focused as orgasm after orgasm hit her! It felt so good! Her pussy felt fantastic, and her cute face all twisted up with pleasure was nice too! Her tsun elements melting away to be replaced by dere dere was cute as hell!

Once I got too close, I once more used Tsubasa's mouth as a place to deposit my load, since it seemed like she didn't mind at all suckling on my tip as I came in her mouth. She just smiled warmly up at me as I blew my load, gulping it all down with ease...

And then I turned my gaze over to Akeno, who had at some point collapsed onto her side due to all the orgasms I'd given her. She was still in her underwear, skin slick with sweat, and I just grabbed her, bent her over the bed next to Rias, and ripped her panties off before shoving my cock in her pussy. "There we go! Nobody can say this wasn't a good orgy, can they?" Before anybody could actually answer sincerely, I used the remote control and made everybody (except Tsubasa) come simultaneously, moaning and twitching as they did. My cock throbbed at the show, enjoying Akeno's pussy spasming around my cock as the beautiful young woman came beneath me.

Once I finished across Akeno's butt, splattering it with a thick sheen of cum, I made Tsubasa lick my dick clean again, considering which girl would get fucked next. I had a good way to make sure everybody was satisfied in the end... so I decided to pay special attention to the girl who was probably the neediest among all my girlfriends - Asuka! I shoved my freshly-cleaned dick in her pussy and went right back to pounding away, watching her big tits bounce, cries of pleasure escaping her throat as I made her come over and over!

Eventually, I ran out of juice to keep going. My cock wilted (which prompted Tsubasa to hungrily lick and play with it as she knelt in front of me. I stopped using my orgasm button on the girls as I just relaxed on the edge of the bed, panting softly for breath as I recovered...

"Dibs on side cuddle," Asuka said.

"Side cuddle? Dibs?" Aika asked, still woozy from all her orgasm.

"When we all lie down for a cuddle, I get to put my cheek on his chest as I cuddle in from the side. His right hand side, I now declare."

"You- you cannot claim such a position by dibs! The position of chosen lady is not so crass!" Kiyome sputtered, while Tsubasa just kept sucking away.

"I can, and did. Dibs," Asuka repeated.

"In that case, dibs on left hand side," Aika added.

Eventually, we did wind up in a giant cuddle pile. It was a bit awkward, given how many bodies there were, but we made it work.

And yes, Aika and Asuka got the side cuddle positions. Gasper wound up cuddling into me from the top, and Tsubasa let me use her lap as a pillow. She was the only girl who hadn't come her brains out, so she was happy to remain conscious for longer.

Honestly, the post-coital cuddling was harder than the sex, once I had that genius idea to make everybody come a bunch using devices!

Next Chapter

High School DxD: ERO!, Chapter 26: Genderbender
Previous Chapter
After I gave Gasper my ultimatum... after I gave Gasper my ultimatum...

Every single member of the Occult Research Club decided to bully me! I don't think they coordinated or anything, but they all did it!

"I thought your love was deeper than just a body?" Koneko asked, the faintest smug smile peeling at her lips, as she enjoyed the fact that everyone had decided to agree with her that I was a cad.

"That's not what I said! I said if I was indifferent to Gasper's gender, that made me less of a pervert!" I wasn't indifferent at all!

"You can't just demand that somebody change something so fundamental about themselves, Issei," Rias said, channeling her onee-sama energy against me rather than in my favor. Rather than speaking as my sempai, she was speaking as Gasper's sempai, and her onee-sama energy was like a crushing force, trying to destroy my will! "Especially when you hardly know each other at all."

"I can't really approve either," Yuuto said. Even Yuuto-! "You were doing so well at helping Gasper come out of his shell, and then you just threw this demand at him..."

"Akeno! You haven't said anything nasty yet, please defend me!"

"Ufufu," Akeno said, a playful smile on her lips. No! She had her sadistic side, and it was coming out right now, directed at me, wasn't it?! "Issei-sama... I'm the one who suggested he try out maid cosplay, you know?" Koneko glared at Akeno at that point, and even Rias threw a sharp gaze of disapproval in her direction. "I thought you two would be cute together. But your response... mm... it is cute to see a young man who's normally so calm and collected completely fall apart with lust, you know?" She casually brushed aside her hair like this had been her plan from the very start!

"Wait-! But you suggested Azazel's gender bending! Yeah! You're the one who made me say those things, actually! Everyone, bully her instead of me!" Nobody agreed to my plan, sadly.

"Even if she suggested it, you're the one who actually said it," Yuuto said. No! Stop using logic on me! I don't like being bullied!

Rias sighed. "You should apologize, sincerely, to Gasper for making that sort of suggestion to him." She crossed her arms, which made her glorious boobs bounce pleasantly in her shirt. "You know that crossdressing and transgenderism are two different things, don't you?"

I did! I'm pretty sure that Tsubasa was the one who gave me top-level talent at understanding that sort of stuff, though maybe one of my other girlfriends was also hiding something? I hope she feels comfortable enough to come clean about whatever it is! "Y-yes, but-! Some people aren't that attached to their gender identity, right? A-and it's not like I said Gasper had to do anything! I just said that he should stop trying to seduce me!"

Rias just sighed. "Issei-kun..." I felt like I'd brought home a failing grade on a test to my parents! It wasn't that I was worried about punishment, or even that they'd make me study more (I got good grades, even before the CYOA!)... but I didn't want to feel like I'd disappointed them! Rias was channeling her powerful onee-sama energy to make me feel bad. "Issei-kun. You do understand that what you said to Gasper was hurtful, right?"

"I... maybe," I said. I didn't know if it was hurtful! Maybe Gasper was thinking Wow, I can be with a big strong handsome guy like Issei, and all I have to do is get rid of my pesky dick?! "If I hurt his feelings, I'll apologize! I promise! I'll go do it right now, in fact!"

Yuuto hurriedly grabbed my school jacket. "I think you should give Gasper some time alone, Issei."

"Seriously..." Koneko said. "What, would you just barge into his personal space like that?"

"I have Safe With You, so it won't come off as threatening!"

"I think Yuuto is right," Rias said with a nod. "Give Gasper some time, Issei."

The uncoordinated bullying-! It was too much! I needed to escape to one of my girlfriends who wouldn't judge me for this sort of thing!

Namely, Yuma/Raynare!

* * *

Gasper laid on his bed, staring up at the ceiling, as he thought about what Issei had said. Ahh! Obviously a normal guy like him wouldn't be into traps! It was just the weird perverts that were his clients who wanted to have sex with him... why had Gasper done something so dumb?!

He knew why he'd done something so dumb... nobody had ever made him feel like Issei did... it wasn't just that Issei was (really, really) hot. (Even though Gasper was normally into girls.) It was that, when he was near Issei, he just knew that everything would be okay.

Issei hadn't been judgmental, even! He'd said, If you want to dress like a girl as a hobby, that's okay! He swallowed as he remembered Issei's hand on his shoulder. His mind started to fantasize, about Issei using that hand, not to reassure Gasper, but to guide him down to his knees.

His cheeks heated up at that mental image. He masturbated regularly, and it wasn't to guys like Issei, okay?! But Issei... ah! It was fine if it was Issei!

He was pretty sure that Issei felt so conflicted because he was straight... and even though Gasper was normally completely straight, he wasn't conflicted at all! Issei was just special, and that was fine!

...maybe Issei would realize that it was fine to have a special exception for Gasper, too? He'd definitely reacted to the maid outfit!

...but probably Gasper had an easier time accepting these feelings, since he wasn't trying to be manly or anything... there was no way that Issei looked like that without wanting to be a big, buff, masculine guy, which meant he wouldn't want to do anything with Gasper.

Ahhhh! Why couldn't it just be easy?! Why couldn't Issei just say, It's okay if you're a boy, you can still be my cute foreign girlfriend! That'd be so much better than this!

Gasper bit his lip, contemplating the feeling of Issei's hand on his shoulder again. He mostly jerked off to stuff where the guy was dominant (probably because it let him feel powerful in a way he didn't in his normal life), but that mental image of looking up at a tall, muscular manly man like Issei, who was directing him down onto his knees... it was also really hot... probably because he knew that Issei wouldn't hurt him at all... (Even if he didn't have any super-strong reason to believe that, it was just Issei's vibe!)

He was just about to start shifting his way out of his skirt and undershorts, when the door opened. Akeno smiled warmly as she entered his room, and he did his best to hide his awkward boner. "Are you okay, Gasper?" She asked, a warm and reassuring smile on her lips.

"Yes," he responded, breathing in deeply through his nose as he sat up on the bed to better hide his boner. Akeno soon sat down next to him. With her sitting so close, he tried to erase his fantasies of doing this and that to her from his mind. She was Issei's girlfriend! You can have thoughts like that about another guy's girlfriend, but not while she's in the room! "I shouldn't have dressed up like a maid."

"Ufufu," Akeno gave that pleasant laugh of hers. "I think it had quite an effect on Issei, didn't it?"

"W-well, yeah, but..." He trailed off, and Akeno let the silence stretch out uncomfortably for several seconds, until he continued. "He got upset and said I should change my sex."

"Mm, I see," Akeno nodded. "Are you more sorry that you made him upset, or that he told you to change your sex, Gasper?"

"I didn't want to make him feel bad! I wanted him to, you know - to look at me, like- like what he said he looked at Kiyome like, when she was in a maid uniform..."

"Yes, it is very fun to have Issei look at you like that," Akeno agreed. "But you know what's even more fun?" She prompted him, and he shook his head. "It's when he stuffs his cock inside you and stirs up your guts."

Gasper's boner, which had probably managed to get down to 75% power, restored to 100% at the mental image of Issei doing that sort of thing with Akeno. She was really hot and he was really hot - it would definitely be insane energy, like a porno come to life. He quietly crossed his legs to try to keep Akeno from noticing his erection.

Akeno just smiled. "I asked Azazel-sama about the way she changed her sex, and it's a very simple process. You just stand there, she points the device at you, and poof! You're the opposite sex. She said it feels totally natural, no dysphoria at all! Oh, and don't worry, if you don't like it, she can just turn you right back," she said, snapping her fingers to make that point. Gasper just swallowed. "You could try it out, and then Issei could do all sorts of incredible things to you... Azazel-sama says girl orgasms are just as good as boy orgasms, but with Issei, they come fast and hard. No refractory period or anything."

Gasper could feel the heat in his cheeks burning away as he fidgeted in place. Akeno placed her hand on his lap, and for a second his horny brain thought she was going to do something sexual to him - but she was actually depositing a little business card there. He took it, fingers trembling. "E-eh?"

"It's Azazel-sama's personal number. If you say Issei told you to call her, I'm sure she'll listen and help, Gasper-chan," she said, giving his back a quick pat. "And if you want to experience the pure bliss that Issei can show you... then you'll have to do it." Her voice was that of a silky seductress, the proverbial devil of legend, as she whispered in his ear!

At that point, she left him there. Instead of calling Azazel, he jerked off. It was to Issei.

He laid in a haze on the bed, still half in the maid uniform he'd worn just to try to seduce Issei. If it was really the sort of thing you could turn off and on... then it would be fine, right? He could try it out, and if he didn't like it... then that would be that.

He got up and called Azazel.

* * *

I laid in bed with Raynare (she told me that she wanted me to call her that in private, now that I knew she was a fallen angel), her naked, sweat-slick body curled up against me. She just sniffed me, stuffing her nose right in my armpit to appreciate the scent, her hand sliding down my stomach towards my cock, teasing and playing with it. "Issei-kun, get hard," she breathed out into my armpit, the feeling of her breath tickling me a little.

"You really don't think I'm bad for suggesting Gasper turn into a girl?" I asked her again. I did feel a little bad! The whole ORC told me it was bad! Except Akeno, kinda, but mostly because she thought it was funny to see me squirming like this!

"Of course not. Azazel-sama turned into a woman, didn't she?" Raynare asked me. "She even did it to be with you! How could it be bad to suggest that Gasper copy her? It isn't like you ordered him to. Those devils just don't understand these things. If they spoke to Azazel-sama, they'd understand that Gasper should count himself lucky to be asked to turn himself into a woman! There are three billion men on this planet, but only one of them has been offered the opportunity to join your girlfriends in sexual bliss! Even Azazel-sama hit on you, didn't she?"

"She did..."

"Does Gasper think he's more amazing than Azazel-sama?"

"Gasper didn't say anything bad about it!" I quickly defended. "He just shut the door! I think I embarrassed him too much! It was the other members of the Occult Research Club who criticized me!"

My cock was back to full mast thanks to Raynare's fingers sliding around it. "There you have it, then. Probably, Gasper was overwhelmed by the opportunity to enjoy sex with you, and didn't know what to say!" She started to lick and kiss her way down my chest towards my groin. "Sex with you is the best, Issei." Her lips wrapped around my cockhead, and she smoothly swallowed up my whole cock with a solemn gulp, her throat swelling as she took me deep inside her mouth.

Okay, so Raynare was maybe (definitely) a little biased because she was a sex addict-! But I needed reassurance, and Raynare was giving it to me! I made her come, since I knew she liked coming, sliding my hand down to grasp her long, silken dark hair, starting to fuck her face, my cock sliding out of and then plugging up her throat, my balls slapping against her chin as I pumped her up and down, keeping her in heavy orgasm bliss as she moved around. My cock furiously throbbed and pulsed as I put her mouth to good use like that, and I just groaned and let myself enjoy all the wet, choked noises of her mouth around my dick.

"Thanks, Raynare," I breathed out, as I f ucked her face, while her eyes peeled back in their sockets from pure pleasure. "You always make me feel better!"

"Gluk gluk gluk," was her only response, accompanied by the wet noises of moans that got repeatedly cut off by my dick, vibrating my length inside her throat. I made sure she kept coming constantly, not letting her stop orgasming for a single second, while she moaned and quivered on my cock in pure pleasure. I hit her with each orgasm only ten or fifteen seconds after the last one, and she spasmed and twitched around my cock, unable to do much more than just enjoy herself.

Then there was a buzz from my phone. I decided to keep fucking Raynare's face, absently continuing to use my sex powers to keep her orgasming, as I leaned off the bed to grab my pants and find my phone. She just moaned incoherently as my cock rolled around in her throat, and then I laid back on the bed, checking the messages.

I just stared at it in confusion. This couldn't be Gasper, could it? That was wishful thinking, right? The message wasn't in my contacts list, though! Maybe it was him?! Maybe he was now a cute girl who I could fuck and make happy?

Ah! He'd (?) seen that I had read his (?) text!

"He did it!" I told Raynare, my cock throbbing and pulsing as I held her down in my pelvis, sending waves of pleasure through her. I resisted the urge to come, though! I had a new girlfriend! Well, we'd probably have to go on at least one (more?) date before we were officially going out, but-! "I- I need to get dressed and cleaned up!" I tugged Raynare off my cock, and she just sat there, panting, mouth half-open, her face pink with exertion and arousal. She was so cute like that! "I'm going to take a shower," I told her, hurriedly heading for my bathroom to wash up.

I scrubbed myself down with soap, getting everywhere I could! I didn't want to stink when I met Gasper again, after all! I shampooed my hair! It took a while, and Raynare wound up arriving in the shower with me, looking at my naked body with obvious arousal, her nipples perky, her slick sex visible. Raynare! Ah! We can't do it in the shower, Raynare, even if you want to! I need to get cleaned up to visit Gasper! "Issei, can I watch you claim Gasper as your latest conquest?"

Oh, right. Raynare was really into watching me dominate other girls, like Mittelt, and Kalawarna... "I'm sorry, but I don't even know if Gasper will want to have sex right away! Plus, it'll be her first time! She might not want somebody watching!"

Raynare pouted, but nodded in acceptance, approaching me in the shower. "In that case, Issei, let me help make sure you're totally clean," she said, leaning into me and starting to sniff and lick her way across my body.

It did turn out I'd missed a couple spots! Thanks, Raynare!

* * *

Gasper was back in the maid outfit, fiddling with the skirt, as she sat on her bed. Issei apparently had really, really liked the maid outfit, given his reaction, and what he'd said about Kiyome... ahhhh! She was doing it! Wait, if he came in here, he'd immediately want to do it, right?! Shouldn't she change?! No, but she wanted to do it, right? She definitely wanted to do it with Issei, so...

Gasper had always fantasized about somebody else just showing up and doing all the tough parts of a relationship for him- for her? Either way, the ideal girl would just pop up in Gasper's room and want to fuck and cuddle without any expectations. Wasn't that exactly what Issei was doing? Except Issei was a guy. A really hot guy. Who was going to make her come her brains out when he came by.

Gasper gulped softly. Azazel-sama had said she could have huge tits... but Gasper wasn't sure about that... for one thing, Issei liked how cute she was when she was a boy, right? And obviously, boys have flat chests. For another thing, she had clients as a devil! Clients who liked her for being a cute trap! If she had huge boobs, she wouldn't look like much of a trap, right?

There was a knocking at the door, and Gasper's breath caught in her throat. She listened, long ears twitching a little, as she gingerly rose to her feet. That was Issei, right? She wasn't wearing shoes, so her socks silenced her footfalls as she approached the door. "Gasper?" Issei called out. "You are the one who texted me, right?"

"Ah! Yes! Coming!" Gasper hurriedly rushed to the door, pulling it open. Issei stood in the doorway, and she felt a sensation she was starting to become familiar with as he loomed over her: her pussy clenching around empty air, her clit throbbing faintly. They were the new base signs of arousal that she had been previously unfamiliar with. "Hi." She waved her fingers awkwardly as she looked up at him.

"You look super cute in that maid uniform, Gasper!" Gasper felt her cheeks light up at that comment. "Um. I was planning to take you out, do you want to go out as a maid? It's cool if you do! Actually, it's great if you do, it was sexy walking Kiyome around in her maid uniform, though I wound up just taking her back to my place..."

"E-eh?! Public... dressed like this?" Gasper felt almost dizzy at the thought. Dressing like a girl in public was one thing, dressing like a sexy maid was a whole other! Wait, she was a girl now, so it was normal to dress like a girl! Also she hated going out in public! Well, she didn't hate it when it was with Issei...

"Okay, you can get changed," Issei said. "I'll wait!"

"I-Issei... um..." She awkwardly stood in the doorway. She wanted him to fuck her right away! She was horny! Becoming a girl hadn't made her less horny! (Surprisingly!)

"Oh! Sorry, Gasper," Issei said, just stepping into her bedroom and closing the door behind him. Gasper felt her pussy clench again as Issei loomed over her. "I just assumed you wanted to go on a date before losing your virginity!" He reached down in between her thighs, sliding his hand up, and up, pushing up her skirt inch by inch. She just panted as she felt his fingers move, her eyes on his face, her lips slightly parted. His lips looked so goo~ood- and her thoughts short-circuited as he leaned down to kiss her on the lips. It was a firm, forceful thing, little fireworks going off in her brain as she experienced her first kiss in a way she never expected.

Issei slid his hand further up, reaching towards her pussy, teasing it through her panties. His fingers felt so good, rubbing against her lower lips, and she trembled in place, gulping as he continued to firmly kiss her, his tongue sliding into her mouth.

His other hand came up to the back of her head, and as he teased her pussy like that, he slowly pushed her back, and back, and back, towards her bed. He laid her out on it, looming over her, and she just sort of awkwardly laid there. Ah! This wasn't what a sexy girl was supposed to do, just lie there and take it! What was she supposed to do?! She tried to remember a hentai where the girl was a maid - and she popped off Issei's lips as she remembered one. "Master, how can I be of service?"

Issei's response was intense! He practically tore his way out of his own pants, tossing them off the bed, and she went cross-eyed as she saw just how huge he was. He had a cock meant for hentai! She hadn't been (that) small as a guy, but that thing was a monster that put her (missing) penis to shame! She was actually a little glad that Issei would never know how much he'd had her outmatched in that department! "Ahhh, Gasper-chan," Issei breathed out, reaching down for her panties. They stuck for a moment, the wetness that came with excitement making them sticky, but he just yanked them off and tossed them aside and left her new pussy to wink in the open air, wet lower lips feeling so strange as the air brushed against it. It was the first time she'd been wet with her pussy exposed like this, and the tender caress of the air sent waves of frisson up her spine. "I'm going to stick it in, Gasper-chan! Are you ready to stop being a virgin?"

"Eep! I mean, yes!" Gasper agreed, nodding her head rapidly, and Issei just plunged his cock forcefully inside her, spreading her lower folds as he laid claim to the insides she hadn't had just yesterday. Her guts felt like they were being rearranged, her body trembling on that wonderful fat massive cock, the alien sensations intense and wonderful. Her legs tried their best to lock around Issei's hips (not that she could hold back a powerful guy like him), and he was soon hilted deep inside her, making her head swim at the sensation of their bodies merged like that. With how big he was, and how small she was, she expected it to hurt, but it felt surprisingly good!

Then an orgasm hit her. It was like a lightning bolt to her brain, white hot pleasure cascading around her thoughts as she orgasmed so, so quickly. She moaned in surprise, hands reaching up to claw at Issei's back as best she could, scraping along his skin through his shirt. He just held himself inside her, as her pussy spasmed and went crazy, her legs locked tight around his hips. This was so much faster than she'd ever come as a boy! It felt just as good, no - it felt better, because she was doing it with somebody else, rather than herself! He rolled his hips around, and his cock rolled through her insides, making her moan in pleasure, before he started to slowly, forcefully, peel his way out of her pussy.

Her mouth just opened and closed as he slowly wormed out of her insides, her head spinning from just how good it felt. It took so long, too, his massive bitchbreaker of a cock making her shudder and drool. If this was how it felt to get fucked by a big, huge cock normally, then she understood why all the girls in hentai were always getting mindbroken by it! Issei slid all the way back so that just the tip was inside, and she whimpered, her orgasm finally finishing so that she could start to put together a sentence. "Issei-"

That was as far as she got before Issei just slammed his hips deep inside her again, making her head spin all over again. She moaned as she came all over again with that massive cock inside her, feeling it pressing around in her insides, her legs once more hooking tight around Issei's lips, trying to hold him inside her. "Gasper! I promise to be a really good boyfriend for you, okay? You're super cute and sweet and having you climbing all over me on our first date was really amazing! Thank you for becoming a girl for me!"

She could only blankly mouth words, but Issei seemed to know what she wanted - or at least what would make her feel good. He grabbed her thighs, holding them apart, and started to pump inside her, his cock pounding away at her fresh pussy. Pleasure ran through her as he just manhandled her like that, so big and strong and powerful, yet she felt safe in his arms, safe being held by him, she wanted this to never, ever end, she wanted him to fuck her silly into a good little puddle of goo for him. She wanted to melt into mindbroken bliss like all those girls in those hentais! She'd always wanted to be dominant because she was scared, but with Issei, she didn't feel scared at all, she felt safe and protected, so she was willing to just let him do whatever he wanted to and with her. He wouldn't hurt her or do anything she didn't like!

He leaned down over her to kiss her on the lips again, and she once more threw her arms around him, hugging him close. She wanted that dumb shirt of his out of the way, wanted to feel up his big muscles, and as if he could read her mind (could he?), he popped off the kiss for a moment, letting go of her thighs to yank his shirt off and toss it aside. She stared up at his muscular chest, eyes wide, her pussy clenching around his cock as a base level part of her (new to being a girl?) said, A guy like this can definitely protect you.

Then he started making out with her again, his tongue diving into her mouth, and pleasure hit her like repeated hammer blows to the head. Orgasm after orgasm, as he thrust inside her, as he held her up by the thighs, letting him get so, so deep inside her, her fresh pussy getting permanently reshaped around his cock. Drool slipped down into her mouth as she took it, her cunt spasming, writhing, gripping, squeezing, milking, as she just kept coming and coming in that position.

He popped off the kiss again, grasping her thighs and rutting away all the harder. She squeaked alongside the mattress, his repeated, forceful thrusts making her brain melt. "Azazel-sama says she didn't figure out how to give you a womb yet, so it's okay if I come inside," Issei told her, and her brain fizzled a little at those words. In hentai, a guy creampieing you was the ultimate pleasure a girl could experience-! Was that real?!

"Come inside!" She cried out, and Issei slammed his cock all the way inside her. She felt as he spurted out cum, and she promptly came right alongside him, moaning in pleasure at the pure white-hot sensation. Her legs struggled against his grip for a moment before snapping around his hips, yanking on him, tugging him deep inside her. Her moans became even louder as her fingers scraped along his back, as they both experienced that perfect ecstasy, together!

Eventually, he finished coming inside her, gasping and panting as he pulled out. His cock was still hard, so big and throbbing, coated in her juices. Her eyes fell on it, considering it strangely beautiful. She'd always liked in hentai when girls were practically hypnotized by the guy's big cock, but now she was on the other end of that equation... and she still liked it! She shifted on the bed, approaching his cock slowly, her fingers reaching out to stroke him. He was still hard, even though he'd come so much inside her... and she leaned forward, wrapping her lips around his cockhead. She was supposed to do this, right? It made the magic power boost work, right?

Her tongue flicked out at the tip of his cock, and her eyes widened as she realized just how good Issei tasted! Her tongue got more active after a moment, slithering around and around, teasing and playing with the very tip of his cock. He tasted soooo good, she let out a hot little pant as she enjoyed his flavor.

"Ahh, Gasper-chan, you're doing great! Thank you! Um, but, could you take more than just the tip, please?" She felt her cheeks glow at that. Duh! The girl suckling on the tip was just foreplay! What was important was taking the cock into her throat! Probably she'd gag, but that would be okay, she could stop wherever she gagged.

She began to descend down his cock, closing her eyes and just trying to remain calm. Issei shifted as she moved, tilting his hips so that they faced her, making it easier for her to descend down his length. His cockhead pierced her throat, and she was shocked to find that her gag reflex was apparently completely inactive (??), but she just kept going, and going, and soon she had that entire, massive, thick, throbbing cock stuffed down her throat, her nose pressed into his pelvis.

Her eyes flashed open, glancing up at Issei, and his cock twitched deep inside her mouth in response. She swallowed around his dick - and then she came! She came from giving a blowjob! It was like something out of a hentai, but she was coming while giving a blowjob! Her hips bucked at the air, her juices practically gushing out, and she was still wearing her maid outfit as she gobbled up Issei's massive bitchbreaker cock while acting like some fellatio slut from a hentai! It felt so good, having his cock deep in her throat like that, pleasure racing through her as she came.

Issei just gently grabbed her head in both hands and peeled her off his cock, though. The wet pop accompanying the exodus of his dick from her lips was like a finger snap (temporarily) breaking the hypnotic power of his dick, and her eyes turned up to him. "You need to breathe, Gasper! It's hard to breathe with a cock in your throat, so-! So I'll make sure you have time to breathe, okay?"

"Okay, Issei," Gasper agreed immediately, her tongue stretching out to flick at the tip of his cock. "I trust you." His cock twitched in response to that, a drop of precum oozing out the tip, and she promptly licked it up.

"Nng! You're so cute, Gasper-chan! I promise to make sure you're happy and safe, okay?! I won't betray your trust, no matter what!" He then gingerly used his grip on her head to direct her down towards his cock again, his massive dick slowly stretching out her lips all over again. He tasted so good on her tongue, her tongue slithering around like his dick was chocolate ice cream, and he just groaned as he guided her all the way down - and once again, she came hard with his cock stuffed deep in her throat.

He started to peel her back immediately, her choked moans massaging his dick, and he began a slow, steady, gentle pace of fucking her mouth and throat. He'd pull out so far that his massive bitchbreaker was no longer in her throat, and then she'd breathe through her nose and mouth, his pleasant scent filling her nostrils, before he pushed her back down. Her nose would mash into his pelvic bone, and she'd promptly orgasm at the sensation of it stuffed all the way down her throat. Then he'd peel her off again, making sure she could breathe even though the pleasure was so much she couldn't remember to care.

Up and down she went, bobbing on his cock. Her throat swelled around his cock over and over, and the entire experience was almost hypnotic, her thoughts feeling like they were slowly fleeting her mind. She could just let Issei handle everything, couldn't she? She could trust him. She could let him take the lead. He was a sex god with a bitchbreaker cock, and she was his cute girlfriend, so it was natural for him to take charge like this. She let her eyes just stare at his muscular chest, only half-focused, as he pumped her up and down his cock.

Occasionally, he'd speak up, telling her how cute she was, how good her mouth and tongue felt, how he'd make sure to keep her safe, and it was like a warm, pleasant dream. She didn't even always consciously process his words, often interpreting them like a dog might: nice and sweet, but what was the meaning exactly? It didn't matter, though, she understood, Issei would protect and take care of her. She didn't have to change anything, didn't have to overcome her hikikomori nature, he'd take care of her even if she was a hikikomori...

And then, suddenly, the blowjob ended, his cock erupting inside her mouth. Thick ropes of hot, tasty cum filled her mouth, and she jerked in surprise as an orgasm simultaneously hit her, eyelashes fluttering rapidly at the sensation. She looked up at Issei and just started to swallow, gulping down his cum in the midst of her orgasm, enjoying his sexy o-face as he unloaded in her mouth. She'd made him feel good, which was the least he deserved, for how good he made her feel, for how safe he made her feel...

When he was finished coming, he popped her off his cock. She sat there, a dazed smile on her lips, as she sat on the bed next to Issei. Him naked, her in her maid uniform. His eyes roamed up and down her body. His cock was still hard. But she'd let him tell her what he wanted her to do next. That just made sense. "That was really good, Gasper-chan! You're a natural at blowjobs-! Er! I mean that in a good way!"

"Thank you, Issei," she said, still dazed.

"U-um... could you call me Master when you're dressed like that?"

"Yes, Master," she told him, feeling a smile tug at her lips. He wanted to do sexy maid roleplay with her. His cock throbbed in response to her words.

"Ahn-! Actually! Actually, you have lots of outfits, don't you? That's what your clients want photos of?"

It was a real question, one that required conscious thought, so the spell broke as she pulled together a response. She felt her cheeks glow as she realized how she'd been acting, like a subby little mindfucked slave! Girls really got like that?! That was kind of scary! She knew Issei wouldn't take advantage of her like that, but still-! W-well, as long as it was Issei, she'd be fine, right? And Issei was the only guy she liked, so it was okay, right? Right... "Yes, I have a lot of photos, Iss- I mean, M-Master," she said, stumbling over his name and the sexy title he wanted her to refer to him by. "I mean sexy outfits! I have lots of sexy outfits! I'll dress up however you want! I can be your cosplay hikikomori girlfriend!" It was perfect, right?! She got up from her seat, planning to go to her closet, but Issei grabbed her by the wrist, stopping her motion immediately.

"Gasper-chan," he said. "Look! It's really sexy how you're dressed, and that you have lots of high-quality sexy cosplays from your time as a G-rated prostitute!" She felt her cheeks heat up at that comment (okay, it was basically true, but-! She was a G-rated camwhore, you know!), but she knew Issei was about to say something serious, so she didn't comment. "But! I don't want you to just live a life as a hikikomori, okay? You're a cute sweet girl, and my girlfriend, but I'd say this even if you were still just my male kouhai! You can't live your life locked away like this, it isn't right!"

Wait! He was still going to make her stop being a hikikomori? Even though she was his girlfriend?! Outrageous! That was outrageous! She felt herself start to tear up at the thought of being forced to leave her room!

"I-! I understand it'll take time, Gasper-chan, but you can't live your life in one room! I'm not saying you have to start doing normal things every day or anything! Don't cry! We'll work at your pace, okay?! And I'll be there to keep you safe!"

Issei did a pretty good job of comforting her... but the mood was ruined, so she didn't wind up showing off her virgin killer sweater to him! Which was what he deserved for ruining the mood anyway!

She changed her sex, and now she had to go outside too?! So unfair!!!

Next Chapter

High School DxD: ERO!, Chapter 25: Too Many Maids!
Previous Chapter
Just fucking her in a maid uniform in the closet hadn't been enough for me - I'd dragged Akeno back to my place and fucked her absolutely senseless into the bed, thoroughly using her sexy body and making her brains all dribble out of her cunt as I sprayed hot cum all over her sweat-soaked body and down her eager gullet.

Once I had used Akeno to fully work out the pent up libido born from having a cute blonde foreign girl curled up next to me all day, constantly looking to me for protection and safety without a hint of concern or worry, making me feel like a real man, making every part of me want to reciprocate that trust with genuine protection...

I realized it was way too presumptive to ask Gasper to magic away his cock after one day spent together! It was actually like asking a girl to marry you after your first date, wasn't it? No, it was even worse, since it wasn't even officially a date! I'd been so horny that I'd completely forgotten all about that, just thinking about how much I wanted to have sex with the cute blonde foreigner that, once Akeno came up with the idea, I forgot about anything reasonable!

Once I realized as much, I tied up Akeno, put her on a saddle vibe, and left her to stew in her own arousal as punishment! Akeno! Hopefully in the future you'll learn not to say that sort of thing and drive me crazy with lust, though frankly I doubt it!

I left Akeno in my bedroom and told Mom to go check on her in the morning if I hadn't come back. "You want me to check on her?" Mom asked, glancing up towards my bedroom. "Did you hurt her?"

"No, I just, uh... look, please just check on her if I don't come back and she doesn't leave on her own! She's breathing and conscious and everything, okay?! It's embarrassing to ask me to say more."

Mom's lips thinned, then she sighed and smiled. "I see. Akeno is that sort of girl, huh?" Argh! Whatever you're thinking, Mom, stop thinking it! "If I do end up needing to check on her, then we'll have to talk, Issei. If you're too rough with your girlfriends, that isn't good. It doesn't matter how they feel about it in the moment. I had a friend back in college who showed up for classes with bruises around her neck one day from some play that got a bit too rough - her boyfriend paid a terrible price for that."

Mom! No! Stop telling me this story! Also, I'm not going to think about the way that people often say 'it was my friend' when describing a situation they went through themselves! I won't think about my Dad choking my Mom during sex back in college! I won't!

I just left without saying anything more, since that would only encourage her further!

* * *

Gasper fidgeted at his desk, his legs pulled up against his chest. Issei-kun was so amazing... he was brave, and strong, and handsome, and he had a whole harem of girls! He was nothing like Gasper at all, really...

He rolled around in his seat a little, sure he looked like one of those wobble toys as he bounced from side to side. When Gasper thought about Issei-kun, he didn't just think, What a cool guy, I wish I was more like him... he thought He's so amazing, I want to do things with him.

Wasn't Gasper straight? He was straight, right? He did cross-dress, but that was because he obviously looked cute! If anything, he was better at appreciating cute girls than a normal guy, since he understood how much effort it took to look that good! His porn folders on his laptop were full of cute girls getting absolutely wrecked by big-dicked traps, okay?! But when he remembered sitting in Issei-kun's lap, or being held in Issei-kun's arms, he had thoughts that weren't anything like a straight guy's thoughts!

The computer pinged as one of his clients requested a new photo set. Gasper bit his lip, then decided to just do it. It'd be a distraction from thinking about Issei's big muscles, and his bulging... thing... and how good he smelled... and how safe he made Gasper feel, and...

Nyooo! You're fantasizing again! Just get in the plugsuit, Gasper!

* * *

Tsubasa hummed along to my story, nodding to herself and placing her hand reassuringly on my thigh as I spoke. She listened calmly, without any apparent judgment, until she finally spoke up when I finished. "I see. It can be troubling for someone, when they first feel attraction to a member of the same sex."

Tsubasa! No! Wait, this is another conversation you've had many times, isn't it, you heartbreaker?!

"Attraction is a feeling that emerges from deep inside. As Blaise Pascal put it, {The heart has its reasons, of which reason knows nothing.} It doesn't matter why you have these feelings, Issei-kun. Words like 'straight' or 'lesbian'-" Tsubasa, you need to adjust this speech when you talk to your boyfriend! "-these are just ways that other people fit you into a neat category so that they can stop thinking about you. It isn't about them being cruel - there are just too many people, with too many different tastes, not to simplify. But it's your life, so you can like who you like, and you don't have to put a name to it, because you'll always know what sort of person you like."

"Yeah, but I'm straight."

Tsubasa smiled warmly at that. No! She's totally had girls say that to her tons in the past, hasn't she?! "If Issei-kun wants to say that, then how can I argue with him?" She raised her hands in a shrug of surrender. Another step down her well-worn decision tree of these sorts of conversations. "As long as Issei-kun makes a decision he's happy with, I don't care what words he uses to describe himself." She leaned into me, placing her cheek against my shoulder. This girl was truly a menace!

"Right, but if I used Azazel's gender bender magic on Gasper, then..."

"Issei-kun." She leaned up from her position on my shoulder, her fingers delicately reaching out to my cheek. "You shouldn't start a relationship by demanding the other person change to suit you."

Nng! That was true-! Fine! I guess I will simply sit in weird unrequited lust where I want to fuck Gasper but not deal with him having a penis forever, is that what you want, Tsubasa?! "You're right," I said instead of all that. I decided to change the subject to the other great question that the past day had given me! "I want one of my girlfriends to dress as a maid full time."

"...huh?" Tsubasa just stared at me in confusion.

"Rias's big brother, Sirzechs, is married, and his wife dresses as a maid and calls him Sirzechs-sama! I'm so jealous, it's like my fantasy come true and he's living it!" I punched my fist into my leg as I admitted as much.

"Issei-kun, I don't understand what you're talking about. Sometimes it can be cute to see a cute girl dressed in an embarrassing way, but isn't that a bit much?" Tsubasa! This is a no judgment zone! Please treat me wanting to stuff my girlfriend into a maid uniform with the same kindness and compassion you treated me having awkward sexual feelings for another guy! Thank you! "It's one thing to ask your girlfriend to go along with a fun idea in the bedroom, but you're talking about something very different from that. It was Grayfia who suggested dressing like a maid, not Sirzechs, you know?"

"Yeah, that's why I wanted your help. I think Kiyome might like it, since she likes being 'forced' into things..."

Tsubasa let out a long sigh as she looked at me, shaking her head. "Issei-kun... there's a difference between a 'ravishment' fantasy and a 'maid' fantasy, you know?" Nng! Okay I actually do know that! They're totally different tags on exhentai, too! "If you want her to play that kind of game with you, you should... hmm. Well, she does prefer being told what to do. Some girls are like that," Tsubasa admitted. "But, Issei-kun, she's a student. She can't be a full-time maid. She has to attend classes, you know?"

"That's true... ah... why must I be tormented by still being in high school?! Why can't I be an adult already so I can make my girlfriends dress up as maids full-time?!" Not all of them! Just most! Or at least some!

Tsubasa smiled lightly, letting out a pleasant little laugh. "If you really want, I could dress up as a maid for you. Just as a fun game in the bedroom, of course."

That's very sweet of you, Tsubasa, but that's absolutely not your vibe! "I don't think that would suit you very well, Tsubasa."

She hummed at that thoughtfully. "Aren't there maid characters who have that vibe? I would definitely be more the 'battle maid', I suppose, but Grayfia is a very powerful devil, you know?" Yes, Rias told me that already! She can crush me with her pinky finger! I get it!

"Wait! I want to rewind the conversation!" Tsubasa quirked one eyebrow at me in curiosity. "The whole idea is that it's sexy for a girl to stay dressed up as a maid, not to do it for sex! I've already had Kiyome dress up as a maid and had sex with her like that!" Also, Aika, and Rias, and Akeno, and Asuka... but Kiyome-! Kiyome seemed like the kind of girl who might do it full time! "So..." I pushed my fingers together awkwardly. "Do you have any advice? You're good at seducing girls, right?"

Tsubasa smiled. "If you want your girlfriend to try something new, you should just explain why it would make you happy. After all, she's your girlfriend, so she wants you to be happy." Thank you for subtly saying that you want me to be happy, Tsubasa! You're very smooth! "Kiyome does like people who take charge with her and set the pace." Wait, people? Are you having sex with Kiyome while I'm not around?

Well, you're both my girlfriends, so it's fine, right? I also definitely am better at sex than you, Tsubasa (sorry!), so I don't have any reason to worry or feel jealous...

"There is one thing, though. The last time you had her dress in a maid uniform, she talked a lot about how flimsy it was." It was a spontaneous wish uniform! You can't be mad at how low-quality it was, Kiyome-! "She liked it." Of course she did, I am a sex god so I got it right without even trying. "But if she's going to be, say, dressing as a maid to go shopping with you, then it can't be that kind of material, you know? As the dominant, it's your responsibility to make sure the sub doesn't do something stupid because they're too horny."

What pearls of wisdom from Tsubasa... "Thank you, Tsubasa."

"You're welcome, Issei-kun," she said. "I would like to see Kiyome in a maid uniform, if you put her in one," she added with a smile.

"I'll make sure to show her off to you!" I agreed immediately. I was gonna do that anyway, because the whole thing that makes it sexy to have a girl dress like a maid all the time is getting to show it off!

* * *

It was getting really late, so I headed home, only to find Akeno talking to my mother over the dinner table. "Oh, Issei, you're back!" Mom said.

"Ufufu. I was just talking about this and that with okaasan," Akeno said with a teasing smile. No! You were talking about sex with my mom, weren't you? "It's clear that the apple doesn't fall too far from the tree. Your mother is a very lucky woman, but then, your father is a lucky man too."

Mom just laughed pleasantly at that. Akeno! Stop buttering up my mom by talking about how great her sex life is! I don't want to hear itttt! "You two are more adventurous than I was at that age, though I suppose nowadays there is the internet to learn about all kinds of things. Back in my day, if you wanted to try something new and exciting, you didn't necessarily know if it was safe, but nowadays, there are guides and everything just a quick google search away!" No! No, I won't think about this!

"I'm going to my room," I declared, hurriedly making my way to the stairs.

"Ufufufu. He's so cute when he's embarrassed," Akeno said.

"He is!" My mom agreed. I slammed the door to my bedroom shut to escape their terrifying and haunting conversation!

* * *

I homed in on Kiyome the next day after school. I didn't have any clubs (fucking my girlfriends  was my club activity, and thanks to Share Interests and Harem King, it was far more personally enriching than any normal club activity could hope to be!), so I went right for her before she could go to her tennis practice. "Kiyome, I want to spend the afternoon with you," I told her.

"Oh! Well, I was planning to do tennis practice, then go home and read some novels, so I suppose you can come along... ah! But in between, I would be in the women's locker room, and you can't go in there!"

"No, Kiyome. I have a specific idea for what to do this afternoon, with you. Skip tennis practice and come with me." I didn't actually physically force her to come (since, you know, I'm super strong but she's just a normal girl), but she followed after me anyway. Once she started, I casually slid my arm around her waist, and she practically purred and leaned into me.

"What are we doing, Issei?" The way she asked the question made me want to just bend her over and fuck her!

I resisted the urge, though! "We're getting you a new outfit." Wait! She'd think we were going on a regular shopping trip and be excited, even if she wasn't willing to be my maid outside the bedroom! "I've decided to play dress-up with you." She nodded along, softly panting as I dragged her out of school. "Remember that time you and some of my other girlfriends dressed up as maids? I want to get you a proper maid uniform, so you can wear it around town. It's the perfect outfit for you." My fingers slid down to grope and knead her ass cheek at that point, wanting to keep her horny so she'd go along with my plan.

"A~ah? Issei... you're... going to force me to dress as your maid? And all these strangers will see me, Kiyome Abe, forced to follow you around in a maid uniform?"

"Yes," I told her. This was the moment of truth! Was she willing to do it?! "You'll also be calling me 'Master' and following my commands."

"And... when will it stop?" She looked interested and horny!

"Kuoh Academy has a uniform code, so tomorrow morning."

She swallowed at that, her breasts rising and falling, her cheeks hot pink. Say yes, Kiyome! Please dress as my maid, I promise to still love and protect you and make you come lots and lots! "I suppose that this is the final fate you always had in store for me," she breathed out.

That was a yes, right? Right? "You forgot a word," I pointed out.

"...becoming your maid was always my doom, Master."

Hnng! She wore this cutely sexy expression, like me ordering her around was foreplay and I was playing with her pussy! Admittedly, I was groping her ass, but I just smiled, kissed her cheek, and moved all the faster to buy her a sexy maid uniform!

* * *

High quality sexy maid uniforms were surprisingly expensive, but in the name of love (and horniness), I was willing to splurge! Kiyome! You look beautiful dressed up as a sexy maid! She smiled as I ate her up with my eyes, my gaze naturally dipping to her full cleavage that the outfit put on display! "Master, do I look acceptable in my new uniform?"

"You do!" I told her immediately, my cock throbbing threateningly against my pants. "Follow me," I declared, her old school uniform now folded up in a bag as she followed after me, heels clacking against the floor.

What should I do now? Take her out for a meal? People were looking at us as we walked, which I didn't mind - and Excellent Lover told me that Kiyome didn't mind either! On the contrary, she was enjoying the attention!

I was too horny to think about taking her out on a normal date, so I just took her home and back to my bedroom! Wait, didn't this round off to costumed sex but we walked back from the store with her in costume? I hadn't even thought of this issue! How was I supposed to put Kiyome in a maid uniform and have her call me master all the time, without immediately dragging her into the nearest private place and fucking her brains out?!

"Ah... Master..." Kiyome breathed out as she stood, trembling at the doorway to my bedroom. "Are you going to ravish and despoil me, ruining my clothes already?"

No! Those clothes cost me money, Kiyome! I'm not going to ruin them! I sat down on the bed, still trying to think of how to control myself. "First... collect all my dirty laundry, and then put it in the washing machine, starting with darks!" Yes. That would give me time to think. It would also let me watch Kiyome do sexy maid duties in her sexy maid outfit, and my cock was certainly enjoying that.

Now, most of my dirty clothes were in the laundry hamper, but there were socks scattered around, a shirt left in the bathroom, that sort of thing. Watching Kiyome diligently following my directions was surging my arousal to its limit, and the fact that she was actually enjoying herself (mostly because I was staring at her constantly) was definitely annihilating my self control. Just barely, I managed to hold back as she carried the laundry hamper off.

"Your laundry has begun, Master," she said, hands primly crossed in front of her skirt. "Are there any other chores your maid needs to do?"

My brain was melting at the sight of her like that. There was no way I could actually make Kiyome dress like a maid constantly, because I'd take one look at her and start wanting to fuck her again! "Yes! My dick needs cleaning!" I declared, hurriedly yanking my pants down, my hard-on surging into the open air, full of desperate energy born of having to hold back so long.

"Yes, Master," Kiyome said, letting out a hot pant as she descended to her knees in front of me, my throbbing cock pulsing in front of her face. She leaned forward and just started to lick, running her pretty tongue across my huge dick, her cleavage on lewd display as she knelt in front of me. Her cheeks were pink with arousal as she moved around, one hand going to the base of my cock to control it, letting her tilt it left, and right, and back again, her hot breaths tickling the underside of my dick as she worked. I just groaned softly in response to her oral ministrations, my dick twitching as she slithered around and around, coating my cock in spit.

Her tongue tasted every last inch of me, her head tilting this way and that as she moved all around. Hot breaths spilled out and tickled my dick, her eyelashes fluttering rapidly, while her tongue teased along the crown of my cock, sliding through it lovingly, brown eyes flicking up to me as if to confirm she was doing a good job. "That's a good maid," I told her, patting her head lovingly. "Your master is very pleased," I told her, and she let out a little noise of delight, continuing to work me over like that, running her lips down as her tongue dashed out, slobbering on my cock in the process.

Soon enough, though, my dick was thoroughly spit-shined, and her tongue was running along the underside of my dick, my length throbbing over her face as she moved up, and up, hot breaths spilling out and tickling the underside of my cock. Kiyome's cheeks were pink - and I just casually planted one hand atop her head, the other taking over holding onto the base of my cock. She let out a hot, wet pant, as I pulled her up to the very tip of my cock - and then her mouth opened wide and expectantly, letting me slide my dick past her lips and shove her down my whole cock in a single quick thrust!

Now that I was 'fucking' her, I could make her come, so I did, enjoying the way she moaned around my cock, her eyes peeling back in their sockets as she came, her hips bucking at the empty air as saliva dribbled freely out of her mouth. "That's a good maid. You cleaned your master's cock, so now you're getting rewarded!" I told her, grabbing her head in both hands and starting to fuck her face. She moaned around my cock as I made her come over and over again, and I didn't even try to hold back. I was pent up! From the moment I'd stuffed her in that maid uniform, I'd wanted to fuck her, and that had taken the whole trip home, plus watching her pick up my dirty clothes, plus waiting for her to return from the laundry room!

It only took me a dozen or so thrusts for me to force her mouth down my cock and just unload straight down her throat, groaning as I found sweet release. I made sure she came right alongside me, her hips bucking at the air as she spasmed and jerked, yet more drool slobbering out of her mouth. "That's a good maid! A good maid helps milk her master's cock when he gets horny looking at her sexy body!" I told her, and she wetly gurgle-moaned around my dick, saliva dribbling out of her mouth as I held her down.

Once I was completely spent down her throat, she slowly, languidly peeled up and off my cock, panting as she caught her breath. Her chin was caked with drool, there were tears in the corners of her eyes, but a smile on her lips, and a rosy pink color to her cheeks as she recovered from the arousal and facefucking. "Master, you had quite a load - oh! Your cock is still hard, Master! Do you need your sexy maid to continue to milk your cock and work out all your arousal?" She asked it genuinely excitedly, clearly wanting to keep going. I guess for her, getting forcibly dressed up by her boyfriend and made to do maid roleplay was also like foreplay that went on way too long!

"Yes, use your mouth for now while I think about-" she slurped my cock into her mouth at that point, hungrily bobbing up and down, hands resting on my thighs as she moved. I just groaned, cut off by the sensation of her throat coiling hungrily around my dick. I gave her an extra orgasm as a reward for being such a horny, eager fellatrix, and she moaned around my cock in response, eyelashes fluttering as she fucked her face on my cock. "While I, think about," I got out, "how I want, to put your sexy body to good use." I made her come at that point, enjoying the way she wetly moaned around my cock, eyelashes fluttering rapidly as she deepthroated my cock over and over, spit slipping out of her mouth and splashing onto my thighs.

My hands just gripped my bed on the edges as she dutifully, hungrily, slurped and sucked and licked on my cock, her mouth bobbing up and down, lips maintaining a tight seal around my dick. The wet glugging noises of her throat around my cock were wonderful, and I could only groan and pant, my cock throbbing in her throat as she went at my cock with relentless force. I finally gripped her head again, holding her down in my pelvis, and unloaded straight down her throat, shuddering softly as I found sweet release down there, with her gulping it all down eagerly.

When I was spent, I pulled her off my cock, and once more, she was left panting, pink-cheeked, but obviously aroused and excited for what came next. Her sclera were pink from all the exertion, and I considered just getting another blowjob. After all, it was 'cock-cleaning'! That was a maid's duty, right? On the other hand-! Actually, you know what, there was no other hand! I could make her come lots, so we could just do all blowjobs right now. "More cock-cleaning! You made it all messy with your spit and drool!" I commanded. "Clean my cock with your lips! Slurp it dry!"

"Master, how can I make it clean with my mouth when I also made it messy with my mouth?" Kiyome asked, sounding genuinely confused. I just want you to suck my cock, Kiyome! Don't apply logic to this!

"Are you questioning your master?" I demanded of her.

She let out a little pant at that, apparently enjoying the arbitrariness of the new rule! "No, Master. Sorry. I'll clean your cock off," she noted, leaning forward to slurp my cock deep into her mouth all over again, slowly swallowing it up in a long, smooth movement. I planted my hand on the back of her head, but it was just to pet her this time, luxuriating in the tight, warm wetness of her throat.

* * *

I laid on my back on the bed, panting heavily as I caught my breath. Kiyome somehow wasn't as exhausted, even though she was moving more? She peeled my shirt off my body as I laid there, my sweat making it stick a little. "Since this shirt is a 'light,' Master, I can go add it to the laundry," she said, my brain dribbling away as she headed off with my shirt, wearing the sexy maid outfit, her juices visibly trickling down her inner thighs from all her previous orgasms.

I'd come down her throat thirteen times. The desire for the cute maid girl was unmatched! My cock had finally given up, though, and as I laid there, I remembered: Tsubasa wanted to see Kiyome in her maid uniform! Also, even if it was a little strange, she thought my flaccid cock was 'cute'! Wait, hadn't I previously called that an emasculating thing to describe my dick as, instead of calling it strange? Had Tsubasa started wearing me down?!

"Maid!" I called out, and I heard as Kiyome hurriedly rushed back to the bedroom, panting as she opened the door, her big tits on full display. "Give me my phone. It's in my pants," I gestured vaguely in their direction on the floor.

"Yes, Master," Kiyome agreed, collecting my pants, fishing out my phone, and handing it to me.

"Thank you. You may go back to washing my clothes," I told her, and she nodded, dutifully leaving the bedroom. Hnng! Truly, the maid girlfriend thing was too sexy! Even my flagging cock, exhausted by the marathon blowjob session, seemed like it might regain its power thanks to her actions! I called Tsubasa! "Hey, Tsubasa, please come over to my place, I have two nice surprises for you."

"Oh, two?" Tsubasa asked. "Hmm. One of them is probably Kiyome in a maid uniform, but what could the other one be?"

"You'll see when you get here!" Hopefully! My dick was starting to come back online. "Please come by soon!" I hung up the phone at that point. I waited until I heard the washing machine start, then called out: "Maid!"

Kiyome arrived quickly. "Yes, Master?"

"Maid, my cock needs you to milk another orgasm out of it with your mouth," I told her, pointing to it. It was only half-erect. "Tsubasa is coming by, so I want to be soft for her."

"Oh! I see, Master," Kiyome agreed, clambering up onto the bed in between my legs. Her lips wrapped around my tip, slurping and suckling on it, one hand starting to jerk me off - then she just dove forward, mashing her nose into my pelvis. Since I had total orgasm control, and Tsubasa was a devil who could fly over to my place at any time, I decided to come right then and there, even though I was only about three-quarters of the way hard! Kiyome just glugged wetly around my cock, desperately gulping it down as it spurted in some mix of her throat and the back of her mouth. A little bit snorted out of her nose, but she didn't seem to mind at all, just breathing through her nostrils before leaning back to clean herself off.

The doorbell rang almost as soon as Kiyome finished licking up my cum, dabbing at the remnants with a handkerchief. Wow! Being able to just fly to your destination was really useful! I could hear Tsubasa's "okaa-sama" from way up here, and soon enough, there was Tsubasa, standing in the doorway, wearing a blouse and jeans. "Oh my," she said, her nostrils flaring. Her gaze wasn't even on my dick - it was on Kiyome's butt! Which, admittedly, was a very sexy butt, and currently in a maid uniform, so I couldn't complain. "Kiyome, you look truly beautiful dressed as a maid."

Kiyome blushed. Hey! Blush when I compliment you like that-! "Thank you, Tsubasa-sama," she said, with a soft smile. "I've been spending all afternoon cleaning and milking Master's cock."

"I see." Tsubasa's gaze went from Kiyome to my cock, and her expression lit up as she saw it, her tongue flashing out past her lips. "It's flaccid... oh my..." She breathed out, shoes clacking as she walked straight for me, my cock trying and failing to become hard again out of pure instinct. "You must have done a very good job of pleasing your master, Kiyome," Tsubasa said, before just clambering up onto the bed and diving down towards my cock, her lips wrapping around my soft cock and starting to suckle and lick lovingly.

I groaned, still sensitive down there even if I couldn't get a boner, and I just shuddered and sighed. Kiyome watched the scene, clearly perfectly happy to take a break from sex thanks to how much great sex she'd already had... ah! There was a great way she could contribute! "Maid, clean my room while Tsubasa-chan sucks my cock," I ordered. Because I wanted to watch her do menial chores! Not because my room was a mess!

"Y-yes, Master," Kiyome agreed, gulping before getting off the bed, her eyes running across my bedroom.

"Try to keep your work to places that Tsubasa-chan and I can see you," I added. My cock twitched a bit in Tsubasa's mouth, and she suckled all the harder on it, trying to somehow force me back down to pure flaccidity. I just sighed as Kiyome realized what I wanted - a sexy show of her cleaning my room, with lots of bending at the waist to show off her tits or ass - and got to work, picking up a few pieces of trash and throwing them in my room's bin, leaning down in such a way as to show off her sexy body every time.

She wasn't efficient, but it was sexy - and Tsubasa agreed, looking at her out of the corner of her eyes as she worked! It was super sexy! Also, Tsubasa kept licking and suckling on my cock, just getting more intense as my body decided to try even harder to get a boner. I shuddered and sighed under Tsubasa's hard work, her tongue dancing around, my gaze repeatedly going to the sexy maid bouncing her tits and ass all over my bedroom as she cleaned.

Tsubasa didn't mind how distracted I was, since she was also distracted! Sometimes, she'd even stop licking to just stare at Kiyome for a bit, and Kiyome definitely enjoyed being the center of attention, flushing and fidgeting as she worked. She practically bounced into the bathroom to grab some paper towels, wetting them and wiping down my desk, scrubbing at one particularly stubborn stain for several seconds before pulling away with a satisfied smile.

All the while, Tsubasa kept suckling my cock, watching Kiyome whenever she was in sight. I just relished the feeling of Tsubasa's lips around my cock, her tongue dancing inside her mouth, and my length eventually began to harden in her mouth, prompting her to get even more energetic in her fellatio, trying to wring an orgasm out of me before my cock could get fully engorged. The rapid slapping with her tongue, the hurried gulping and swallowing around my tip when it started to press against the back of her throat, her sucking and slapping of her lips, just excited me further, making my sadistic side want to bully her at least a little by letting my cock get to full mast - sorry, Tsubasa!

Soon enough, she was plastered to my dick, my cock throbbing and pulsing in her throat as she desperately gulped around my fully erect cock. My attention was now on Tsubasa, ignoring Kiyome prancing around the room as my cock furiously throbbed and twitched in her throat. She swallowed all the more rapidly, her brow furrowing as she tried to wring an orgasm out of me - and I finally let go, sighing as I unloaded straight down her throat. She eagerly gulped and licked, and didn't pull off for one second as my cock began to soften inside her mouth, smiling with her eyes as I returned to full softness.

When I glanced her way again, Kiyome was pouting slightly as she put my pens back in the cup - but when she saw I was looking at her once more, she lit up immediately, starting to sway her hips as she performed a variety of mundane tasks.

My room ended up clean, and in the end, I ended up naked, with a maid Kiyome attached to one side of my body, and Tsubasa - still in the casual clothes she'd shown up in - to the other.

They woke me up with a double blowjob, too! Ah! The harem life was definitely for me!

* * *

"Sorry, Issei-kun," Rias said, as I showed up at the building, starting to guide me to Gasper's room. "He says he won't leave unless you're there... it's much easier to get him out of his room without a fight. I can pay you for your time, since I'll probably be asking you to help with this again."

"I'm happy to support my kouhai," I said. I didn't want to look like a stingy guy who made his girlfriends pay me for stuff like this! Still, why did Safe With You apply to Gasper? He was a man! A man! It didn't make sense!

Akeno laughed lightly, apparently picking up something from my expression. "Ufufu. Issei-sama is at his cutest when he's flustered, right, Rias?"

Rias just sighed, shaking her head. "You shouldn't tease Issei-kun so much, Akeno."

"Ah? Issei-sama hates it when I tease him?" She wore a cute worried expression as she looked up at me, her lip trembling. "Issei-sama, is that true? Am I being mean to you when I tease you?"

No! I like it," I said. Did I like it? "It's fun as long as we do stuff afterwards."

"Ufufu. Issei-sama truly does have a one track mind. I'm not teasing Issei-sama right now, anyway," she said, giving my butt a light pat, and we finally arrived at Gasper's room.

I swallowed and approached. Yes, he's cute, but he's a boy. You can't make him do sex stuff with you! You can't make him change his gender! Even if he dresses like a girl, that's his choice! Actually, if you think about it, isn't it brave to continue dressing like a girl even in a situation like this?! To be so in touch with whatever makes him want to dress like a girl that he doesn't care?! Yeah, it's actually admirable that he's being this way, kind of! I knocked on the door. "Gasper?"

"Ah! Issei! Hang on, hang on! Rias didn't say you were coming!" He sounded all flustered, and I could hear something fall over inside the room. "Shoot, shoot-! Please wait a second, okay?! I'm not decent! Eee! Don't open the door, for real, okay?!"

"Ufufu. He really is just like a maiden in love when Issei-sama is around."

Rias just sighed. "Of course he is. Gasper doesn't want to be a hikikomori, so the fact that Issei provides him with the ability to leave his room with confidence makes him act attached. You shouldn't read too much into it, Akeno."

Yeah, Akeno! Our friendship is purely platonic!

"Okay. Okay," Gasper said. He was now on the other side of the door, clearly hyping himself up to open it, so I just stood there patiently and let him take the initiative. I could hear his heavy breathing as he readied himself.

It took him a while. I'm pretty sure he touched the doorknob, then withdrew his hand, then touched the doorknob, at least three times. But then, finally, he pulled it open.

He was wearing a cute maid outfit. Even though he was a guy he wore it bashfully yet gracefully at once, with all the energy of a shy girl who's prepared homemade chocolates for the first time as he stared up at me, hands clasped in front of him. "I-Issei-kun, h-how do you like th-this cosplay of mine?"

I stared at him, time seeming to telescope around me, my brain trapped like an old sci fi computer confronted with a paradox. Gasper was a super cute maid! Gasper was a boy! Gasper was looking for my approval at having put on sexy fetish wear! I was straight! Gasper was adorable! Gasper was male!

"Ufufu. It looks like your outfit had a strong effect on Issei-sama, Gasper."

"I-is that good? Do you like it? I-I heard that you like maids..."

"Gasper!" I planted one hand firmly on his shoulder, and he straightened up immediately. My brain had only one thing I could say! "I know somebody who can turn boys into girls, if you want to keep trying to seduce me then I need you to be a girl, okay?! If you're a girl then you can seduce me all you want and I promise to make you feel really good!"

Gasper stared up at me, his mouth slightly agape. I'm sorry, Gasper! But it had to be said!

"Issei! You can't just make Gasper do that sort of thing!" I'm sorry, Rias! But it had to be said!

"So cruel... you didn't even say that Gasper looks good in that outfit." I'm sorry, Akeno! You're right!

"You look really good in that outfit, but you're a guy! Please get your gender changed if you're going to try looking so sexy for me! I barely managed to hold back when I took Kiyome out to buy a sexy maid uniform, and even then, I immediately took her home, had her start one load of laundry, and then we had sex basically all night!" Gasper's cheeks turned scarlet at that, and he slammed the door shut.

No longer confronted by my stupidly sexy kouhai, I could restart my brain to see Rias looking at me in annoyance, and Akeno just looking amused at my behavior.

"Sorry, Gasper! If you want to dress as a girl as a hobby, that's okay, but if you're going to seduce me, please get your gender changed! I'll give you Azazel-chan's phone number so you can talk to her about it!"

Rias just shook her head slowly, while Akeno laughed.

Sorry! But it's the truth!

Next Chapter

High School DxD: ERO!, Chapter 24: An Inobvious Trap
Previous Chapter
“So the Governor-General of the Fallen Angels is now your girlfriend…” Akeno seemed bewildered by the idea.

“Issei-kun…” Rias started. “It isn’t that I am jealous, but she is obviously using you for your Booster Cock ability.”

“Maybe that’s how it started, but now! Now Azazel has learned the joys of being a woman! Namely getting to orgasm lots and lots while I fuck her mouth!” I countered.

“Even if you say that, is that really the basis for a relationship?” Rias asked.

“Yes! Sex is a physical expression of affection! It’s no different than if Azazel-chan wanted to cuddle!”

“Azazel-chan, hm?” Akeno asked, reaching out to pinch my cheek. Her pinch was pretty fierce!

“I think it’s quite different than if she wanted to cuddle,” Rias replied.

“Look, lots of relationships have gotten started because the boy and the girl were both interested in the same thing. It happens to be that me and her are both interested in sex. Specifically, blowjobs.”

After a few seconds, Rias turned away from me to Yuuto. “Yuuto,  you’re a boy,” Rias said. “Please reason with him.”

"Issei can make his own decisions about things like this. If I were in his shoes, I wouldn't have eight girlfriends, but it is his life. If he thinks that his relationship with Azazel is a good one, that's his decision. Also, she just saved my life, so I wouldn't feel good about encouraging him to break up with her."

"Yuuto! Thank you for your honorable words!" I decided to just hug him, making him briefly stiffen in surprise - and then hug me back.

"You're just saying that because he's saying that it's okay for you to keep expanding your harem," Koneko said, sitting upside down on the couch. "Also, doesn't Azazel make it nine girlfriends now?"

"That's right," I said, releasing Yuuto from the hug. "Azazel is one of my girlfriends, just the same as Rias, or Akeno, or Yuma- Raynare?"

Rias sighed, crossing her arms. "That's another thing: Issei, I understand you're very good at sex. But Raynare literally only became your girlfriend to try to kill you. Can you really consider that a good foundation for a relationship?"

"No. The foundation of our relationship is that she loves me! In fact, now that I know her true nature, I feel much more confident in our relationship!"

"Really?" Koneko said flatly.

"Really! Before, yes, I did worry that Yuma-chan was just using me for sex. While she was very affectionate in the bedroom-" Koneko made an exaggerated gagging noise, "-maybe she was just like that because she enjoyed the sex! Now, though, I know that she didn't just make Mitsuru and Kaori fuck me because of her incestuous threesome fantasies, but instead because she was trying to protect me from being killed!"

"Issei-kun, that might just be because she wants to keep having sex with you..." Rias pointed out.

I had already prepared for this line of argument! "If she wants to keep having sex with me, and protects me from danger as a consequence, isn't that no different from a normal relationship?!"

Rias's eyes tilted up and to the left as she thought through my impeccable logic, then at last she let out a sigh. "Alright, Issei-kun. I just don't want you to be hurt." She stepped up to me and gave me a hug, her large breasts pushing into my chest in the process as she just sighed against me. It was a nice feeling, being hugged by my big-titted girlfriend! I hugged her back so she knew I cared about her too! "If anything happens, tell me right away, alright? I won't say 'I told you so' or anything. I'm on your side." Uwaaa! She had incredible mature onee-sama energy, where you anticipate future relationship problems and head them off with your greater life experience!

Which was sort of weird, since she didn't have a boyfriend before me, whereas I had nine girlfriends, so I had much more relationship experience than her! I guess that's just the power of being one year older than me! Wait, is that correct? Well, people say girls mature faster than boys, so maybe that's it? Either way! "Alright, Rias! Thanks!" I squeezed her back tightly, making her let out a little laugh at the pressure. "I know Yuma and Azazel will prove you wrong!"

"You don't have anything against fallen angels?" Akeno asked.

"Of course not!" Firstly, I barely even knew what a fallen angel was! Secondly, I'd only met five of them, and four of them were hot girls who sucked my dick!

Admittedly, the fifth had tried to kill me, but you can't judge a whole group by the actions of one individual!

"I'm not racist! I have multiple fallen angel girlfriends, you know?"

Akeno let out a light chuckle. "Of course, Issei." She then came in to join in on Rias's hug, making it a group hug! I was being double-hugged by two earnest sweet busty beauties! I was in heaven!

Unfortunately, at that point, our conversation was interrupted by a sudden, magical glow that filled the room - and then Sirzechs stepped forward, his wife at his side. Urgh! I was so jealous! His wife dressed like a maid all the time! Being an adult was amazing, you can just dress however you want! At the same time, I'd feel bad about making one of my girlfriends dress like a maid 24/7, but apparently Grayfia was into it? Where was my maid fetishist girlfriend, God?!

...actually it was probably Kiyome, wasn't it? She liked being forced into things, and wouldn't it fit to be forced to dress like a maid all the time? Mwahaha, you are now lowered from the position of tennis princess to bangmaid! Something like that... I'd need to workshop it. Akeno, Aika, and Tsubasa would probably know best...

Rias and Akeno stopped hugging me as Sirzechs arrived. "I've heard that there's been a bit of a shakeup in your boyfriend's harem," Sirzechs said, a pleasant smile on his face. Didn't this guy have a sister complex? Shouldn't he want to kill me for fucking his sister and also a bunch of other women?!

"That's... correct," Rias said at last. "Azazel-sama is officially one of Issei's girlfriends. Additionally, it turns out that Yuma was in fact Raynare, a fallen angel, and Issei has chosen to stay in a relationship with her." She was just arguing I should break things off with them, but now she was speaking to her brother as if our relationship was assured! Rias! I love you! Thank you for supporting me in my decisions, even when you disagree!

Sirzechs was completely ignorant to such subtle undercurrents in Rias's words, of course. That was the whole point! "Heh. To seduce the great Azazel-sama... I did think it might happen one day, but I certainly didn't imagine the person to do it would look like you, Issei," Sirzechs said, humming to himself. "I imagined that person looking more like Rias, perhaps. Obviously, not Rias herself, since she's far too pure to seduce a man... although, I suppose she's very young, so perhaps in time she'll become more of a femme fatale..."

"Sirzechs-sama," Grayfia interrupted. "Please, focus on what we actually came here for." And not your sister complex, she didn't say.

"Ah, yes." Sirzechs cleared his throat. "There will likely be some diplomatic talks with Azazel-sama, now that we are possibly looking at a marriage alliance down the road... heh. Riser thought he was a far better political match for you than Issei, but look at you now! You're not that far off from becoming the co-wife of the Governor-General of the Fallen Angels! My little sister truly knows how to pick her future husband!"

"Otou-sama, if you're just here to say things like that, you can go. I will just imagine your fawning, it will be less embarrassing than this."

"My apologies, Rias-sama," Grayfia said, apparently deciding her husband was never going to get to the point. "Due to the changes in your circumstances, it has been decided that you may unseal your Bishop, Gasper Vladi."

"I know you can handle it, Rias," Sirzechs said. "The other devils didn't think so, but they decided it was too risky to keep one hand tied behind your back, so I managed to talk them into it! Aren't I a great elder brother?"

Rias just ignored him, looking at Grayfia. "Thank you for the information, Grayfia. Is that all?"

"My master-" uwaaa! His wife calls him 'my master!' Can I get Akeno or Kiyome to do that? Actually, just Master would be best! "-also wanted to talk about how wonderful you are, but I believe he's mostly gotten that out of his system."

"My sister and wife... conspiring against me!" He let out a laugh that made it clear he wasn't actually offended. "Alright, Rias. You'll probably want to go speak to Gasper anyway."

At that point, Sirzechs and his wife both used teleportation to leave the room. I was left to think about the idea of making Akeno dress up as my maid full time. Would she go along with it? She was very subby and masochistic in the bedroom, but she also had strong onee-sama energy outside of it... that gap moe was very sexy, but how would it play with a maid cosplay? I tried to imagine Akeno as a teasing onee-sama maid, and blood started to pour from my nose.

"Ugh. Pervert. There's not even anything happening," Koneko said.

"That's only a thing in manga! This is a perfectly normal, banal nosebleed!" I lied, grabbing a tissue and dabbing at my nose.

"Come on, Issei," Rias said. "It's best that you meet every member of the Occult Research Club, after all." I nodded and followed Rias, along with the rest of the ORC, to a room that was sealed up with magic seals and a big line of tape with the words  KEEP OUT emblazoned on it. It had a certain forboding sense, but Rias casually made it all disappear, and then opened the door.

"Eeeeeeeek!" A girl screamed in panic and shock and I saw her dive into a large cardboard box located in the corner as the door opened up.

"Ah... sorry," Rias said with a sigh, as I pulled my hands away from my ears. "Gasper's an enormous hikikomori."

"I see..." So it was this type of character. The cute but shy girl, who would act all bashful and meek, but eventually realize her own inner strength, thanks to the protagonist's help, and develop a crush on him! Hopefully that protagonist would be me rather than Yuuto, because he already had a girlfriend and was monogamous! (If he hadn't been monogamous, I would have let him have Gasper if things worked out that way! I definitely think the prince type is a classic match for such characters!)

"What are you thinking about, perv?" Koneko asked.

"I was just thinking that I wanted to offer Gasper my help in going outside!" I declared. It was even basically true!

"Noooo..." Gasper whined, closing up the box she was hiding in. "I don't want to go outside!"

I decided to approach Gasper. I did have the Safe With You bonus from my CYOA, after all! "Gasper," I said, as I stepped up next to the box, gently planting my finger on the lid, then slowly tugging it up.

Up close like this, she was super cute, staring up at me with big round red owl eyes. She had pointy ears and blonde hair. A cute foreign beauty! Yes, she didn't have much in the way of a chest, but that's okay! I like all kinds of girls! If anything, I was happy to have some variety- oh, okay, that's a lie, I do like big boobs the best, but still!

"Hi. I'm Issei." I reached down with my hand towards her.

She remained in that weird crouched position that let her (mostly) hide in the box, but she nervously reached out towards my hand, giving it a (very flaccid) handshake. "H-hi, Issei," she said. "I really don't want to go outside. Don't make me!"

"Okay. I won't make you do anything. Can you come out of the box now? Everyone here is your friend - Rias, Akeno, Koneko, and Yuuto. Plus me, and I'd like to be your friend." She turned bright pink at that. So cute! Even with Safe With You, I didn't want to do anything to scare her, so rather than just smothering her in a surprise hug like her reactions made me want to, I just gently helped her out of her box.

"Wow," Koneko said. "I'm surprised you got Gasper to come out so easily."

"Isn't it obvious?" I couldn't help but smile smugly at Koneko. "Don't you know why I'm this hot?"

"Because of a CYOA?" Koneko asked flatly.

"Because of a CYOA. And you know what else I picked? Safe With You!" I gave Gasper's hand a little squeeze, and she blushed again, nervously smiling up at me. That pick had been truly perfect for this situation! Now that I thought about it, maybe it was helpful for Xenovia too? After all, she constantly let me be alone with her and 'force' her into sex... could the CYOA's magic have helped that absurd situation along?

"Hm." Yuuto took out his phone with a frown. "I remember I tried out that CYOA too, though it didn't do anything for me. I picked that option too. Yes, here. Women never think you're threatening to them. They will be comfortable and feel safe being vulnerable around and with you. They trust you won't hurt them or let them be hurt."

Koneko's brow furrowed at that. "But Gasper isn't a woman."

"Well, obviously it's meant to include girls around your age, too! Otherwise none of it would work on Rias-sama and Akeno-sama, since they're both technically underage." Older than me, though!

"No, Issei," Rias said. "Gasper isn't a woman." I just tilted my head in confusion, then looked down at Gasper, who was beet red at this point. Rias! Don't bully poor Gasper like this-! "Gasper is a boy who likes to wear girls' clothing."

"What?" I responded, my brain stuttering.

"Ufufu," Akeno laughed. "I wonder if Issei-sama's Safe With You will stop working now that he knows Gasper isn't a girl?"

"Th-there's no way, right?" I turned to Gasper - she would surely defend her honor against these crass girls! "No way a girl as cute as you is actually a boy? They're teasing me, right, Gasper?!"

"I-I'm sorry!" Gasper said, on the verge of tears already. No! "I'm- I'm a boy, like they say, I'm sorry I have such weird hobbies!" She- no, he pulled his hand away from mine, hiding his face behind his hands.

On the one hand, Gasper was a boy. On the other hand, even if he was a boy-! Yes, that's right! Even if he was a boy, I wasn't here to have sex with Gasper, or get another girlfriend! I was here to offer support to someone in need, that's right! I should still be the cool senpai to my cute underclassman! Even if he looked so cute and girly that he gave some of my actual girlfriends a run for their money! Sorry, Tsubasa, but if you bound your breasts or Gasper padded his chest, I'd probably think you were the boy of the two of you! Not that I don't think you're pretty, you absolutely are-! Ah! These complicated emotions! They've prevented me from protecting this innocent young kouhai! "Gasper," I said, placing one hand on his shoulder and giving it a firm, reassuring squeeze. "It's okay. I'm not upset."

Okay, that was a lie - I was upset! Upset at God! Why would He make such a cute girl and then decide to make Gasper a boy instead, huh?! To take such a shy cutie with lovely blonde hair and a petite little body, a waifish physique and personality, even a love of girly clothes - and then make them male? Isn't that too cruel?! To me and Gasper both, in fact?! If Gasper was a girl, then she would get to be part of my harem and I would treat her nice and teach her the wonders of womanhood and make her come over and over again-!

"You seriously are a pervert," Koneko said with a huff.

"I'm not!" Wait, or should I say I was?

"Gasper is a boy and you still want to fuck him."

In one sense that was true, and in another sense it was false. On the one hand, I wanted him to be a girl since he was super cute and adorable, and if he was a girl, I would have sex with her for sure! On the other hand, Gasper wasn't a girl, so I didn't want to have sex with him! I didn't say either of those things, though, because a great counterargument came to mind: "If I'm indifferent to his gender, doesn't that make me less of a pervert?"

"Wha-?" was as far as Koneko got before I continued my explanation.

"If I'm indifferent to his gender, that would mean that I admire the beauty of his soul, rather than his body!"

"You've been in this room for two minutes," Koneko said.

"And I already learned lots about Gasper! I learned about his hobbies, about his shyness, and I can even see the computer he works on!" I pointed to the computer, which was currently displaying a chatlog with a client... I ignored the fact that the client was making suggestions on what sort of cosplay Gasper should wear, and that the client's taste was so good-! A gym uniform with bloomers and thigh-highs! Seriously, these guys really were just doing G-rated prostitution, weren't they?! "It's not too difficult to tell what someone is like from only a short interaction!"

"Ara ara... truly, Issei-sama is an enlightened man," Akeno said, in a way that sounded sort of sarcastic.

"This is ridiculous..." Koneko muttered under her breath, but I had expertly outmaneuvered her in the field of debate, so she had no choice but to accept her defeat.

I looked at Gasper again, whose eyes were moist but shining as he looked up at me, exciting every instinct within me that made me want to protect a cute innocent frightened waif! Uwaaa! Cruel God who made this poor thing a boy! I'll become overwhelmingly powerful and beat you up for this cruelty!! "Let's go outside, Gasper," I said, offering my hand again. "I promise to protect you." Safe With You had worked earlier, so it should still work now, right?

Gasper tentatively took my hand, his other hand going to cover his mouth as he nervously blushed.

"Oh my..." Akeno said. "I expected it to be a lot more difficult to get Gasper to leave his room."

"Last time we asked, he used his Forbidden Balor View, and hid in the closet," Rias explained. "Specifically, on the top shelf, in the back... it took ten minutes for us to find him, and he promptly clawed at every single surface to stay in his room." She sighed, then smiled. "I'm glad that you are getting on so well with Gasper, and that Gasper is getting on so well with you. Let's start with something easy, like going out to eat at a restaurant. Where would you like to go, Gasper?"

"Ah!" Gasper squeaked in shock at the sudden question. The shy waif character who couldn't answer simple questions like this-! Just make him a girl, God! Why do this?! I understand some men might be totally okay with a trap character, but surely it would be even better if such a character had two holes down south for you to put your dick in, right?!

After a few seconds of Gasper fumbling for words, Koneko broke the silence. "Gasper always orders pizza delivery."

"Eh?! How did you know that?!" Gasper replied in shock, and Koneko raised one finger, pointing towards a corner. In that corner was a tower of twenty pizza boxes, all stacked atop each other.

That is the hikikomori life, I suppose...

* * *

As we all went out to the nearest pizza place, Gasper clung to me like I was a life boat, he couldn't swim, and we were in the middle of the ocean. His eyes darted around constantly, but whenever he saw something even vaguely scary (which included but was not limited to: guys who looked like yakuza, guys who looked like delinquents, girls who looked like delinquents, police officers, people who were particularly tall, foreigners, people who were particularly muscular...). Any guy would probably have felt intense jealousy at having such a cutie clinging to me at all times like that. He sat right next to me at the restaurant, and whenever anyone who wasn't part of our group tried to talk to him, he'd instead talk to me.

If he was a girl it would have been a perfect 100% route clear maneuver! Even though Gasper fit the shy waif archetype, it wouldn't be a surprise at all for such a girl to quickly spread her legs for the man she trusted to protect her in all things, even though she was a complete virgin otherwise!

Unfortunately, he wasn't a girl! Damn you, God!

After the restaurant, Rias convinced our party to go to the arcade. It turned out that Gasper was quite good at video games! He also only played games that could be played with at least two players and cooperatively, and only if I played with him... ahhh! I wanted to go find God and beat Him up!!! This should have been heavy advancement on the Gasper route, but I don't like guys, damn you God!!! You should go to Hell and get torn up by devils, I bet they don't do things like this! Perhaps this was even the reason why Hell had gone to war against Heaven in the first place?!

"Seriously... I can tell you're thinking weird things," Koneko said. (This was a four player machine, so she was playing alongside us.)

"I am not!" I lied.

"Stop being mean to Issei-sama," Gasper said, his voice sharp. My eyes tinged with tears. Such a beautiful and sweet thing-! Argh! "He's a perfect gentleman."

I'm not, but thank you for your trust, Gasper!

* * *

In the end, we wound up taking Gasper back to his hiki hole, with him trading emails with me... he promised to send me lots of emails in the coming days and weeks, and I was sure he'd keep that promise.

"Issei-sama, you get on very well with Gasper," Akeno said. "I never would have thought it would be so easy to get him to leave his room."

I didn't have the capacity to hold back! Even though I knew he was a guy, my body still responded to such a cute thing clinging to me! "Akeno, come," I ordered her, grabbing her wrist and just tugging her along with me. She let out a small noise of surprise - then smiled as I just dragged her into a nearby closet.

"Are you seriously going to just do it right there?" Koneko asked from outside the closet.

"Yes!" I told her. "If you don't want to listen, then go away! Akeno, use your devil wish magic to make a maid uniform and then put it on!"

"Ara ara, Issei-sama is hungry right now... did having Gasper clinging to you get you excited?" She sounded horny at the thought, but she also just raised one hand into the air, a magical sigil appearing - and her clothes vanished, then rearranged themselves into a maid uniform.

"No, it was thinking about Grayfia," I lied (well, it was partly Grayfia), my hands reaching out for her breasts immediately, fingers sinking into the soft flesh - she'd decided not to wear a bra during her maid uniform wearing. "That's why I'm making you dress up as a maid. It's so sexy that Sirzechs's wife just dresses like a maid and calls him Sirzechs-sama all the time!" My cock throbbed inside my pants, and Akeno reached down to stroke my hard-on through my pants. "Ahh... let's pretend you're my full-time maid-wife right now!" I declared, my dick twitching in her grasp.

"Ara ara... and what does a full-time maid-wife do, Issei-sama?" Akeno asked, fluttering her eyelashes up at me.

"First off... she gets my dick out!" I declared. Akeno laughed melodiously, but dutifully unzipped my pants, pulling them down, my cock emerging from my underwear and throbbing in her grasp. Her fingers delicately, lovingly started to stroke me, a smooth movement clearly meant to tease rather than get me off. "And then... ah fuck it!" I declared, flipping up Akeno's skirt and then just slamming my cock inside her, making her come as I bottomed out in her pussy.

She moaned in delight as she felt me filling her up, her tight pussy coiling around my cock hungrily. I shuddered at the sensation, all that pent up desire now allowed to be excised with this act of pure bliss, holding myself inside her even as I gripped her thighs. Her legs were spread, and I started to fuck her pussy at that point, pounding away, my balls slapping against her ass as I hefted her up and down, pinning her against the wall as her arms dangled around my neck.

"Oh, oh Issei-sama," she panted out, huge breasts bouncing, scarcely contained in her top. My eyes were drawn to them naturally, due to the fact that they were huge, jiggling tits, the biggest pair in my harem probably. I leaned down into them, mashing my head against her breasts, relishing the feeling of the soft funbags on either cheek. She moaned in delight at the feeling, as I pumped away at her pussy, finally able to unleash my pent up energy on her compliant body. "Issei-sama, ahm, yes, I'm your maid-wife, I clean your house and fuck you silly, ohhh, I love you Master, ahn~!" She squealed as she came anew, her eyes rolling back in their sockets as her pussy just squeezed and milked my cock extra hard.

I let go on her body, acting relentless with it, groping her tits, her ass, and pounding at her slick cunt. Sometimes I forced her to orgasm several times in rapid succession, and other times I just let her enjoy the feeling of my huge cock pounding inside her au naturel. When she could talk, she did a very good job of dirty talking in her role as maid-wife.

"Oh, yes, Master! Servicing Master's cock is a maid's duty, and my duty as your wife, too!" "Oh, we're making such a mess, Master, but it's okay, this is a wife's joy too, servicing her husband and making a big mess in the process! Don't worry, I'll clean it up after!" "Ohhh, you love my big tits, don't you? That's why my maid uniform always has them on display for you, Master! I love it when you stare at my boobs!"

The mental freedom of simply roughly fucking Akeno was intense and pleasurable, especially with the way she responded to my every movement with arousal and enthusiasm. There was one problem, though: I couldn't come inside her! While Perfect Control meant that it didn't hurt to hold back, and didn't require any willpower either, it was kind of like being teased, and I wasn't in the mood for being teased! So after giving Akeno a dozen back-to-back orgasms as I pounded inside her that many times, her pussy spasming around my cock wildly as her eyes rolled around in their sockets, I finally pulled out of her.

She instantly collapsed to her knees on the ground in front of me, panting for air, her face bright red, blinking away tears as she stared up at my cock, mouth half-open as she caught her breath. I didn't wait for her to fully recover, instead grabbing her ponytail and stuffing my cock past her pretty lips, sliding into her mouth smoothly. She licked and slurped, doing her best to clean my cock of her juices, while she started to masturbate, playing with her cunt as she sucked. Her violet eyes stared up at me, earnest and loving and sexy, and I soon had her nose pressed into my pelvic bone, her face mashed up tight against my groin. I made her come in that position, enjoying as her body spasmed beneath me, her throat hungrily coiling around my cock, her moan serving to vibrate my dick as it rested deep inside her.

Then I unloaded. I hadn't come since before Grayfia and Sirzechs stopped by, and since then, I'd made a new friend, had dinner, played at the arcade, until at last now I could blast thick ropes directly into Akeno's stomach. That was at least six hours of pent up lust, all of which was spent not just being clung to by the cutie Gasper who my body refused to recognize as a man, but also being surrounded by Akeno and Rias's bouncy breasts.

When I finished down Akeno's throat, I peeled her off, enjoying the wet pop. She caught her breath, desperately sucking in air, looking up at me with pink sclera as she knelt before me. My cock loomed over her face, and she casually leaned into it, rubbing her cheek against my dick as she looked up at me, one hand coming up to handle and angle my manhood. "Ah... my husband-master's cock is still hard... I pleasured it with my pussy and cleaned it with my mouth," she said, her voice husky with arousal and exertion. "What shall I do next, Master? As your maid-wife, it is my duty to please you, and I love pleasing you." She started to kiss my dick, soft little pecks that ran all across my length, full of love and sweetness.

"Keep sucking me off," I told her, and her kisses ran up my whole length. "I have a lot more than one pent up orgasm waiting to have my maid-wife wank me off for."

"Mhm," Akeno said, wrapping her lips around my cockhead, then sliding smoothly down my length. There was no resistance, only the feeling of her lips forming a tight seal around my cock, and her tongue dancing hungrily all around the inside of her mouth. Hot, wet, sloppy drool escaped her mouth, dribbling down her chin into her cleavage, as she bobbed up and down my cock, smoothly moving all along it. Her head twisted and tilted from side to side, her smacking, eager lips serving to further stimulate me - and then I reached down for her top and just tore a hole in it, earning a small squeak of surprise at the sudden, forceful action.

With only a little effort - by this point, I really was super strong by any reasonable standard, and while Akeno was a devil, she weighed the same amount as a normal girl - I pinned her up against the wall, stuffing my cock into the crevice of her pre-slicked-up tits. Her fingers reached up for her breasts, squishing them around my length, and I just grunted as I started to fuck her fat tits, relishing each and every thrust of my cock in between them, humping away, my cock pulsing and throbbing as she applied intensive pressure to my length, leaning down to wrap her lips around my tip whenever I pounded her tits hard enough.

I made her come in that position, making her moan around my cockhead in delight, but I just kept pumping, enjoying the way she squirmed and jerked with each orgasm. After a couple minutes, I pressed my cock deep into the valley of her tits, grabbing the back of her head and holding her in position, letting out a cold roar of excitement as I unloaded directly into her mouth, splattering her palate and tongue with thick globs of cum. She eagerly gulped it all down, and once I was finished coming, she popped off.

"Ara ara... Master really was so pent up. Even though it was his second load, there was so much," she said, idly running her fingertip along her lower lip as she looked up at me lustily. "Is Master done working out his libido on his maid-wife?"

"No, absolutely not!" I told her, my cock twitching in front of her face excitedly. I contemplated her body - and then decided to just stick my dick in her mouth again, groaning as I pumped at her face, balls slapping her chin as she wetly glugged around my dick.

We went on like that for about an hour, with me fucking her mouth, tits, cunt, and ass in various different positions, and unloading in her mouth multiple times. She didn't mind going ass-to-mouth! I can tell! I have Excellent Lover!

By the end of things, cum had stained her chin, neck, cleavage, ass, and outfit, which was also a mess in other ways. Torn in several places, tits on full display, sweat sticking to it, her juices having similarly stained it from a few squirts... she was a complete mess, but she was also very satisfied, nuzzling my impossibly erect cock in the aftermath, her face a total mess as she snuggled into it, hand caressing the base of my dick as she rubbed her features against me.

"Ah... Master... are you done?"

"For now," I told Akeno, patting her head. "Good girl," I told her.

She used her magic to turn her complete mess of a maid uniform into an undamaged school uniform and stood up. "I'm happy that I could help you work off all that energy, Issei-sama. If you ever decide to use that energy on the poor boy who excited you so much, please, let me watch, okay? Ufufufu," she tittered with a smile as I blushed.

"I-I don't want to have sex with Gasper! He's a guy! I don't want to have sex with guys!"

"Issei-sama..." She hesitated for a moment, then gave a single peck to my cockhead. "Ah... if Issei-sama really doesn't wish to satisfy his fujoshi girlfriends by letting them watch him rail a tiny cute trap..."

"He doesn't!" I told her.

"...then doesn't Issei-sama have a girlfriend who used to be a man? Gasper seemed to like you very much, so if the cost is becoming a girl, he might be willing to pay it, you know?"

Gasper as a girl! The whole reason Gasper was so enticing and yet horrible is that he looked like a girl, even though he was a guy! But if he became a girl... no! I couldn't just assume that he would be willing to do something like that! He was my friend, he probably liked his dick and didn't like me having thoughts like this-!

But...

Well...

If he did like me and want to do that sort of thing with me... and was willing to accept that price...

Wasn't I being cruel to deny him...?

Yes, actually, if you look at it rationally, if Gasper is the sort of person who is willing to change their sex to be with the person they like, and that person is me, then it would be cruel not to mention this possibility to him!

My cock was raring for another go at that thought! Maybe fem-Gasper would even have huge breasts!

Rather than risk Gasper telling me 'no,' though, I just put Akeno's mouth to good use again!

Next Chapter

High School DxD: ERO!, Chapter 23: Sexy Older Woman
Previous Chapter
I blinked awake, staring up at the ceiling. It wasn't my room. The surfaces were tile, like a hospital room or something, and I swung my head around. It was Rias and Akeno! "You two saved me!" I said, smiling. "I knew you wouldn't go along with the stupid idea of abandoning me to an obvious trap."

Rias hesitated for a moment, then spoke. "We didn't abandon you, Issei, but shortly after you entered the church, a powerful force field appeared around it. We couldn't help you."

"Huh?" That was all I could think. "Then how am I not dead? I'm pretty sure I got stabbed a bunch."

"That would be my doing," came an older female voice. My head immediately swiveled, and I remembered vaguely what had happened just before I'd passed out: this sexy older woman had shown up to save my life! Yuma's mom (?), Raynare (?), had called her Azazel-sama. "Raynare told me about Kokabiel trying to have you killed. With my power, it wasn't too difficult to stop Kokabiel."

"Oh, okay," I said, nodding along with her words. I then turned to Rias. "Could you explain to me what happened?"

Rias giggled at that, patting my head, exuding powerful onee-sama energy in the process. "Kokabiel wanted to restart the war between the fallen angels and devils, and decided that you were an obstacle to doing that, so he had to kill you. Azazel is the leader of the fallen angels, and doesn't want the war to restart. Raynare is a fallen angel, and Kokabiel's direct subordinate."

"So, Azazel is a good guy?"

Akeno let out a laugh. "He really doesn't understand anything."

"I'm a good guy," Azazel agreed - or maybe argued with Akeno. Azazel looked down at me, running her fingers through my hair softly, exuding something even more powerful than onee-sama energy: MILF energy! She had the sort of energy that said, It would be totally normal for you to put your head in my lap and let me clean out your ears! "I think that someone like Issei-kun is exactly what our peoples need right now. Someone who can bring fallen angels and devils together."

"Um. I think I missed the part where I'm bringing fallen angels and devils together?" I prompted. Did I have sex with Azazel and forget it?! I'd be super upset if my first ever sex with a much older woman was completely forgotten!

"Oh, right," Azazel said, turning away from me towards elsewhere in the room. There was Raynare, looking shy and unsure, averting her gaze and rubbing her arm awkwardly. She was still dressed in that super sexy slutty angel outfit. "This is Raynare," Azazel said, "but you probably know her better as Yuma."

"Wha-?!" I gasped in shock. "No! Yuma is a cute girl my age, this is her mom, right?!"

"Azazel-sama wouldn't lie to you!" Raynare snapped, sounding angry at me for daring to question her. "What she said was true," Raynare said. "I was sent by Kokabiel to investigate you, after your fight with Riser." She was?! Wait, huh?! I don't understand this situation at all... Yuma didn't really investigate me at all, did she? We went on a couple dates and then pretty much just fucked in my bed for hours? I know she likes me, but we never really talk about much, right? I thought she was just really into physical shows of affection like sex, but it makes even less sense if she was supposed to be investigating me! I don't think Kokabiel wanted to find out what my sweat tasted like, but Yuma learned a lot more about that than anything about Rias or Akeno or devils! "I used magic to disguise myself as a girl your age, to seduce you."

"But... then... huh...?" I sputtered out, and Raynare used that magic, turning into Yuma, proving she wasn't just making things up! Probably!

Rias crossed her arms at that, giving the other girl a glare. "If I had known that Yuma was secretly a fallen angel, I don't know if I would have been so approving of her being your girlfriend."

"Isn't that racist?" I replied. Akeno stiffened at that for some reason. "Rias, remember when Kiyome was upset because you were a devil? Isn't this just the same thing?"

Azazel laughed at that, having a very 'ojou-sama' laugh. "Well, I don't think it's quite that bad on Rias's part. When Raynare says she was sent to investigate you... she's kind of lying."

"A-Azazel-sama, please!" Yuma was instantly on the verge of tears. What?! Why was this old hag making my girlfriend cry?! I'll mess her up!

"You can be the one to tell him the full truth, but lying is no basis for a proper relationship," Azazel said, crossing her arms. "I think it's high time you come clean. Hopefully, Issei will still accept you."

"I will, Yuma!" I promised instantly, having no idea what I was promising!

Yuma swallowed. She didn't look at me, but instead at her feet, and her voice warbled a little. "Th... that first date... our first time together... I was s-supposed to kill you," she admitted, fidgeting with the hem of her skirt. What?! Yuma, you were supposed to kill me?! I guess that explains why I didn't think you wanted to have sex that first time... wait! That's not what I should be thinking about right now, right?!

"But you changed your mind, right, because I'm so awesome?" I asked her.

"Yes!" Yuma agreed immediately. "I don't want to hurt you at all, Issei! Ah! In fact, that's why I had you fuck Mittelt and Kalawarna!"

"Who?"

"A-ah... Mitsuru and Kaori," Yuma said. Wait... her sisters...? I guess it makes sense that they were fallen angels too. "They were my subordinates, but they disagreed that you should be left alive, so I thought that if you fucked them, they would understand that you should continue to live! And I was right!" She added, when everybody gave her various weird looks!

"It makes sense!" I said, defending my girlfriend, as is my duty as her boyfriend! "After all, sex with me is really good!"

"Thank you for still loving me, Issei!" Yuma just about glommed onto me on the bed, hugging me tight, pressing her cheek into my chest.

It actually hurt. "Ow, ow," I gasped out, and Yuma hurriedly released me.

"You still need to finish recovering," Azazel explained, her voice soft. "Your injuries were quite bad. I think you'd be dead by this point, if you were just a normal person."

Oh, yeah, that's right, I got stabbed with a bunch of magical light beams by Kokabiel. Wait! "What about Yuuto? Is he okay?!" He wasn't here, after all!

"He's okay," Rias reassured me.

"He's convalescing in the next room over," Azazel told me. "He just needs to sleep it off - Kokabiel wasn't nearly as thorough in messing him up."

I nodded along. That did seem to make sense. "Ah! I should go check on him, right?"

"You should stay in bed, Issei," Rias said, gently placing one hand on my shoulder.

"Issei is very energetic, even when he's horribly injured," Akeno said, nodding to herself.

"I know!" Yuma (or should I say Raynare?) said. "I completely forgot all about his injuries because he was defending me! Issei, don't do something stupid like that again, okay? It's fine if Yuuto dies as long as you're alive!"

"It absolutely is not fine for Yuuto to die!" Rias said, scowling at Yuma.

Azazel laughed pleasantly at the scene, a gentle, feminine chortle. "Oh my, Issei. Looks like having such a big harem can have its own kind of woes, even if the girls aren't jealous of one another. This is why Sirzechs is only married to one woman, isn't it?"

"It's because his wife has huge breasts and dresses like a maid as a hobby," I replied, making Azazel laugh uproariously.

"True," Azazel agreed, as she finished laughing. "What man could resist monogamy with a woman like that?"

"I-I'll dress like a maid as a hobby!" Yuma offered. "If you want!" Yuma! That's very cute, but unnecessary!

"If Issei-kun ordered me to dress like a maid, I suppose I would have to," Akeno teased, placing one delicate finger against her lower lip as she contemplated the idea.

Eh?! Was today the day my maid harem life began?! No, wait, there are more important things to think about, like Yuuto! Or Yuma secretly being a fallen angel sent to kill me but who had fallen in love with me instead!

* * *

In the end, Yuuto recovered faster than me. It took him a while to wake up, but once he did, he was walking around with ease, telling me that he was sorry for being defeated by Fried, how he wished he was stronger, how he unnecessarily endangered me - and I was responding by telling him that it was okay, I was his friend, he didn't have to be the 100% perfect most invincible guy in the world!

Eventually, his weird guilt complex subsided enough for him to stop apologizing for stuff that wasn't his fault, and my body recovered enough to stand and walk around without any issue. I stretched and cracked my neck and bounced on my feet.

Azazel had stayed by my side the entire time. She apparently was deeply concerned about my recovery and wanted to make sure I was okay, which was sweet, especially since I didn't know her at all! Was it because she had concern for her subordinate, Raynare, who was in love with me?

Oh, right, Raynare! While I totally forgave her for planning to kill me since she never actually even tried to do it and instead was now my sweetheart girlfriend who liked licking up my sweat (and had me fuck her comrades so that they wouldn't try to kill me either), the revelation of her true nature did make one thing clear:

The reason our dates were always so miserable!

After all, she was actually much older than me, so when I took her out on a date for a girl my age, obviously she didn't enjoy herself! Would a thirty year old lady like the sort of date you take an eighteen year old on? Of course not! "What sort of dates do older women like?" I asked Azazel, since she was an older woman.

Azazel chuckled at that, a smile on her lips. Her fingers rested against her cheek. "Hmm, dates for older women? A nice dinner, with some champagne and candle light, I think that's the standard. Imagining your future together. If you talk about sex, you should always be, hmm... seductive, I suppose is the word," Azazel explained.

"What do you mean?" This was important! As Raynare was my older girlfriend, I wanted to be able to woo her.

"Oh, it's hard to explain to a boy your age," she said, leaning back and crossing her legs and arms, closing her eyes as she bent her head forward slightly. "You should hint at sex. Nothing too crass. You're teasing her, suggesting you'll make love later on, and that gets her warmed up."

"I see," I nodded along. "But Yu- Raynare seems to like just jumping to the sex?"

"Ah, well... that girl's a sex addict," Azazel said, shrugging her shoulders, which did interesting things to her breasts. "You were asking about dates, not how to have sex with a sex addict. I think you've already figured that one out," she said, wearing a sly smile. "Just make her come her cute little brains out, like you did to Mittelt."

"Mittel... oh! Mitsuru! Right! Yes... oh no! Wait, um, Raynare wanted to make her my permanent sucktoy!"

Azazel snorted at that. "I heard. It's cute, seeing you kids play together - oh, from my perspective, you're both young," Azazel explained, licking her lips. "She got very defensive when you were threatened, and decided the appropriate punishment for Mittelt was to become your permanent sucktoy. As to Mittelt's feelings..." Azazel shrugged, her breasts pleasantly bouncing again. "If she was bothered, she could just... not suck your cock, you know?"

"That makes sense," I said. I thought about it for a long moment. On the one hand, Raynare was into sadistically dominating Mittelt, and she was my girlfriend. On the other hand, maybe Mittelt wasn't as into it? Well, if Mittelt ever said to stop, then I'd stop! Actually, last time I'd facefucked her, she'd wanted me to keep going, so I guess it was fine, right? "Thank you, Azazel," I said bowing my head.

Azazel just smiled warmly at me, radiating bountiful MILF energy. You know - that sort of warm energy that said, Ufufu, isn't this junior cute? I want to just ruffle his hair, he's so adorable! "If you really want to thank me, you could take me out on a date. I've never been wined and dined before."

"Wha-?! No way! You're crazy hot, Azazel-sama! Nobody ever asked you out?!"

"Nope," she told me, speaking with utmost sincerity.

"Then let me be the first! Please, be my girlfriend, Azazel-sama!"

She chuckled at that, a light smile on her lips. "That's a bit forward, I think. First we go on a date, then you take me home, kiss me at the threshold... oh, hell," she said, laughing warmly. She leaned towards me, pressing her lips up against mine. Her tongue was aggressive and experienced as it pushed past my lips, tasting at my teeth and my gums, making me half-moan into her mouth. When she pulled back, I was left panting softly. "Let's skip all the foreplay, Issei-kun. I want you in my mouth - can you give me that? We can do other things later - oh, that's an idea. You can come up with a date while I suck you off."

To emphasize the point, she gently placed one finger on my chest, pushing me until I was lying down on the bed I'd been so recently convalescing in - and then she clambered up atop me, her breasts swaying beautifully beneath her. I shuddered as her breath teased my skin. "A-ah, where are Rias and Akeno and Y- Raynare?"

"Mm, it's school time, Issei. You're excused because you're injured, of course," she noted, her lips kissing along my neck as her hands expertly unbuttoned and unzipped my pants. She got down to my waist and pulled my pants and underwear down together - and she gasped as my cock burst free, her violet eyes widening as she saw the enormous thing bounce out into the open air in front of her. "Holy hell. This thing's a monster," she breathed out, going a little cross-eyed as she stared. "How big?"

"Twenty-eight centimeters," I told her.

She let out a small laugh at that. "Yeah, I'll bet you measured this thing," she said, her hand reaching out to stroke along my cock. She leaned forward, tilting my cock towards her mouth, her tongue reaching tentatively out towards my slit, moving with genuine uncertainty, like she'd never done this before and had no idea how it tasted. Had she somehow been a virgin? Maybe it was because she was a fallen angel, and they were all virgins? Had Raynare been a virgin and I'd taken her first time?!

Such questions fell away as she let out a soft breath of delight as the taste of my cock ran across her tongue, her eyelashes fluttering. Her expression twisted into one of raw lust, and she leaned forward, wrapping her lips around my cockhead and moaning softly as she started to slide down my cock. She paused when my cock filled her mouth, most of it still outside - my dick was just outside her throat.

"Don't worry!" I told her. "You can suck it down easily, like magic!" She raised one questioning eyebrow, but followed my suggestion, pushing her lips slowly down my length. Tentatively, at first, but as my cockhead entered her unresisting throat, soft wet noises vibrated around my dick. My fingers bunched up on either side of me. It was her first time! I definitely didn't get the impression that she was into rough stuff, so I let her take her time, slowly but surely enveloping my entire cock, swallowing me up and pressing her nose into my pubes.

"Oh, that's good," I breathed out, once she was all the way down. "That feels really good!" I got the impression that she wanted to come - so I gave her an orgasm! She let out a choked moan around my cock, her hips bucking wildly back and forth, her eyes wide as she spasmed in pleasure, cheeks flush with arousal. My length furiously throbbed and pulsed inside her throat.

For several pleasant seconds, I watched her ass wiggle in the air behind her, her large breasts pushing into my thighs - and then she slid back and off with a wet pop. Her eyes were wild with lust, licking her lips hungrily, her fingers stroking my cock almost absently. "Wow," she breathed out, the word exuding nothing but pure sincerity, and my cock twitched in her hand. "That was the best orgasm of my life, Issei."

"Th-thank you?" Wait, had any of my girlfriends had the sexual experience necessary to compare it? Were my orgasms super effective?! I'd have to make sure to make my girlfriends come lots, so they didn't end up experiencing withdrawal from my super orgasms!

She smiled at that, leaning down, running her tongue slowly and lovingly around the ridge of my cockhead, making me pulse, a single droplet oozing out of the tip, which she gladly licked up a moment later. "I think I should be thanking you, Issei. Without you, I never would have gotten to experience such pleasure. Please, make me come lots and lots."


"Yes ma'am!" I told her. She let out another small laugh, and then slurped my cock into her mouth once more, eagerly diving down to the base of my dick. After a couple seconds of happily twisting her head around my cock, she looked up at me, eyebrows raised. "Oh, right now?" She nodded around my cock, twisting it around in her throat, and in response, I made her come, groaning as her throat spasmed wetly around my cock, her eyelashes fluttering rapidly. She just held herself down, fingers gripping my waist, as my length throbbed and pulsed inside her throat.

The feeling of her pleasantly tight throat around my cock, moaning and vibrating, brought waves of pleasure to me. Her tongue slapped wetly and inexpertly, and as her orgasm wound down, it shifted to just licking the way one might an ice cream cone, hungrily slithering along to taste me. After a few long, pleasant seconds of her twisting her head around, wet little noises of pleasure vibrating up my cock as she tasted me - I made her come again, enjoying as once more her whole body vibrated, her breasts jiggling and bouncing, her ass waving in the air as she humped it, her cheeks flush with color.

Since she was already sucking my dick, I decided - what the heck! I reached down for her breasts, fingers sinking into them, and she let out a soft noise around my cock, vibrating it in her throat and mouth. She peeled back, which made me briefly worry that I'd gone too far. "You like them?" She asked, jiggling them in my hands, and I nodded rapidly. She stripped herself bare with remarkable speed, simply grabbing the base of her dress and peeling it up and over her heart, revealing her completely bare breasts! She wasn't wearing a bra?! My eyes stared in wonder at the large round orbs. She giggled pleasantly at them, bouncing her hips up and down, acting more like a schoolgirl than the ancient and venerable head of the fallen angels! "Bouncy, huh? Do you think they should be a little bigger?"

She asked it so mildly that it seemed like it was just sincere curiosity - but no girlfriend of mine should feel ashamed of her body! All my girlfriends were beautiful in their own ways, and Azazel was definitely very sexy, even if somehow nobody had ever asked her out! "No! You're beautiful just the way you are, Azazel!"

She smiled warmly at that. "Oho. A real sweetheart, hmm?" She smiled, wrapping her breasts around my cock, starting to massage up and down my spit-slick length. I let out a soft breath in response to the pillowy things wrapped around my dick. "It's fine, though, Issei. I'm just asking what sort of breasts are sexiest. If I make them bigger, or smaller, that's just my body, my choice, right? I mean, I doubt you were packing a dick this big before your own body remodeling!" As if to emphasize the point, she squeezed her breasts extra tight around my cock, making me groan, leaning down to suckle on the tip, tongue dancing around inside her mouth as she tasted me.

"A-ah, I don't know, Azazel," I admitted, my cock pulsing in between her breasts as she suckled all the harder. Her tongue danced this way and that around the tip of my cock, hungrily tasting my cockhead like it was delicious. "You really are pretty just the way you are!" She tightened up her soft breasts on my cock in response to that, either to try to urge a real answer out of me, or just because she wanted to reward me - I didn't really know! I just groaned in pleasure, my cockhead pulsing in Azazel's mouth, and she hummed hungrily, nonverbally begging for my cum!

So I decided to give her what she wanted, and exploded in her mouth. She greedily sucked down my cum, gulping and moaning happily as she tasted it. When I was finished, she popped off, swilling some of my cum for a while, her large breasts pink with arousal and exertion, her fingers having left visible markers across the outside that only added to their natural beauty. Eventually, though, she swallowed.

"Amazing... your cum tastes so good, Issei!" She told me, a bright smile on her face. She hopped off the bed for a moment, tits bouncing, and she hurriedly peeled her way out of her panties - a very bland, utilitarian pair, nothing sexy - before bounding back atop me, pointing her pussy right at my cock. "I always heard cum tastes salty and unpleasant, but yours is delicious," she told me, rubbing her slit against my cockhead, letting out a shuddering pant.

"Ah, is this your- first time?" I asked her, unsure if that was appropriate thing to say, but if she was a virgin, I wanted to make it special-!

Azazel blinked at that, looking thoughtful, her lips pursing... "Yes and no. Don't worry about it!" She declared, then slammed her hips down my cock anyway, her pussy going wild around my cock.

I groaned at the sensation, the wet warmth of her slick sex tight around me something truly incredible and obscene. Azazel's tight inner walls squeezed taut around my cock. She wriggled and writhed atop me, grinding my dick around inside her. "Ohhh, sex is so goo~ood, getting a big dick deep insi~ide you, Issei," she breathed, twisting her hips as my cock rubbed all over her insides, grinding every which way. "Ah, ah, I want to know what it feels like when you come inside and knock me up!" She sounded deliriously aroused and I could tell she definitely wanted to feel my cum splatter her womb!

"I don't! I'm too young to be a father!" I grabbed her hips, trying to pull her off, and she moaned and came - even though I wasn't using my power to make her come! It did make it easier to pop her off entirely, my dick slapping against her taut stomach. "Azazel, I barely know you, I can't have a child with you!"

Azazel panted for several seconds, blinking with flushed cheeks. "Oh, Issei..." She sighed softly, idly trailing her fingertips across my cock. "I can't get pregnant, don't worry. That was just dirty talk."

On the one hand! It was totally fine to dirty talk about all sorts of things that weren't true, like Kiyome dirty talking about me forcing her to do all kinds of things! On the other hand, you should tell your partner stuff like that! On the first hand again, though, if she couldn't have children, then I could understand not wanting to just say that outright...

She smiled. "Oh, it's just a little issue," she told me, shifting her body up, teasing my cock at her pussy again. "I can fix it later, don't feel bad." Huh? You can just fix infertility? Well, okay, I guess. "Please, fuck me like one of your girlfriends, Issei! Do to me what you did to Raynare to turn her into your fawning fuckpuppy!"

"I don't think that's a very appropriate way to talk about my girlfriend!" I told Azazel - and then decided to go for it! I grabbed her by the hips, earning a momentary giggle before I slammed my cock into her waiting sex. I started to roughly pound her up and down my cock, making her orgasm over and over again, moans escaping her throat, her breasts bouncing wildly up and down! "Be nice to Raynare, I know she has a hard time expressing her feelings, but she's actually-" Well, actually, she's sort of sadistic with her underlings and gets off on forcing them to fuck her boyfriend, so...

Luckily, Azazel was too busy coming hard on my cock, her eyes rolling around in their sockets, to notice that I'd trailed off. "Yeah! You're both my girlfriends, so you have to get along, and Raynare has seniority, so if you can't, then I'll stick with her!" I declared, shifting her body so that now Azazel was the one on her back, grabbing her thighs and spreading her legs to let me get deep inside her. Her breasts bounced with every thrust.

"O-oh," she said, her voice coming out with a staccato stutter as I furiously fucked her, her eyelashes fluttering wildly as she got fucked hard, orgasms constantly running through her as her eyes peeled back. Her breasts looked gorgeous, and I soon hooked my arms around her thighs and reached up for her large, soft breasts, fingers sinking into them. "Oh, don't worry, I-I-Issei," she stuttered out, in between orgasms, "Raynare, likes me, a lo~ot, we can have threesomes, oooo," she moaned and quivered.

"Okay! Yeah! Let's have threesomes!" I told Azazel, who nodded rapidly.

"A-ah, this is what it is, to be a woman," Azazel moaned, casting her head around, her skin growing pink with arousal and slick with sweat as I furiously pounded her. "Ooohhh, I'm so jealous, I wish I'd done this befo~ore, make me your woman, Issei, fuck and claim the Governor-General of the Fallen Angels!"

"Yeah!" I grunted, fucking her all the harder. "You're part of my harem now, Azazel!" I told her, and she nodded rapidly, moaning as I kept her orgasming, making her come again and again. "It's pretty big, but I promise to be the best boyfriend I can for you!" She moaned happily, eyes rolling back, though that may just have been because of all the orgasms!

With one hand, I took hold of her hip, using it to keep her on my cock, as I moved over to my pants. Luckily, any awkwardness in terms of movement was overpowered by the continuous waves of orgasms I was sending through Azazel, who was just moaning incoherently by this point. I found my phone, pulling it out, and calling Yuma! She liked threesomes, after all!

I heard the sound of the phone going off from just outside the room. Huh? She was right outside the room the whole time?! But Rias and Akeno were at school, so she should have been there too-

Oh yeah, she didn't actually go to school, since she was only pretending to be a school girl my age! Right! "Yuma! Come in here!" I commanded, continuing to fuck Azazel - and a sheepish Raynare entered the medical room. I realized that the fingers on her right hand were drenched in her juices, which meant-! She'd been struggling all alone out there with her needs just to give me and Azazel private time! She'd even heard me say that we should have threesomes, and had resisted the urge to come in because she didn't want to ruin Azazel's special moment of losing her virginity! She was truly a sweetheart deep down! "Come kiss me while I fuck Azazel!"

"Y-yes, Issei!" Raynare said, hurriedly dashing up to me, glancing out of the corner of her eye down at Azazel. "You aren't mad at me for-mmph!"

I cut her off - and answered her question! - by grabbing her and pulling her into a forceful kiss. My tongue danced around inside her mouth, and she moaned softly into my mouth, her fingers reaching up to stroke my hair lovingly, her hand running along my chest, her own tongue becoming just as energetic as mine as we sloppily made out. After a few seconds - with me continuing to fuck Azazel's brains out, of course! - she reached for my wrist, guiding my hand down to her pelvis, inviting me to start fingering her, which I obviously did, making her moan happily into my mouth, pressing up against me.

I could tell that she wanted to watch Azazel get fucked too, though, so after a while of making out with her, I popped my lips off Raynare's, letting her rest her cheek against my shoulder as I continued to pound her sexy boss into the mattress! "Ah... even Azazel-sama cannot resist Issei-kun's cock," Raynare breathed, giggling softly as she spoke. "Show Azazel the delights of womanhood, Issei. Show her your power!" My cock throbbed inside Azazel, and I took the advice to heart, pounding away - and continuing to finger Raynare, and making her come repeatedly.

Azazel mostly just moaned and twitched on my cock as I fucked her silly. When she did speak, it was to offer up all sorts of lewd lines about how wonderful sex was, how wonderful womanhood was, how she wanted me to come inside her... which prompted Raynare to suggest that it would be amazing for her "two favorite people" to have babies together, and start begging me to come inside Azazel.

I didn't, though! After a good hour of fucking, when it looked like Azazel had been thoroughly wrecked by a couple hundred orgasms, I pulled out of her pussy and came all over her stomach, thick splatters of cum racing up to her full breasts as I let her come to rest on the bed, panting heavily.

Raynare responded to the act with a little whimper of unhappiness - and I gave her one last orgasm, her hips bucking against my hand. She moaned and pressed her forehead into my shoulder. When she was done coming, she got down over Azazel and started licking my cum up, her tongue dancing along the older woman's naked body, licking up sweat and my cum with equal delight.

It was super sexy! My cock was raring for another round!

"Ahh... this isn't how I would have thought a threesome with you and Azazel would go at all," Raynare said, her voice soft.

Wait! She had fantasies of exactly this? As her boyfriend, I should try to make them real! "How'd you think it would go?"

Raynare giggled at that, slurping up cum. "Mm... I thought that you two would both fuck me together. Azazel's cock in my pussy, yours in my mouth."

"Um, Azazel doesn't have a cock," I pointed out. Did she mean a strap-on?

"Oh," Azazel breathed out, shuddering on the bed. "I invented a device to turn myself into a woman, so that I could become your lover."

"Huh?" I asked.

"Well, I did tell her about how sucking your cock gives you a power boost," Raynare said, like that helped at all!

"Huh?" I repeated.

What the pair had said, though, actually made perfect sense. After taking the time necessary to fully process the surprise that the pair had just dropped on me after fucking Azazel for an hour... Azazel herself looked up at me, her expression concerned. "I understand if you don't want to keep me as your girlfriend any more, Issei-"

"No! You're still hot, you still have big boobs, you still saved my life, and you're still nice to me! Plus, Raynare! She wants threesomes with the two of us, but I don't want to share my girlfriends with other guys!" Sorry, Aika! I understand totally how you want to have threesomes with two hot members of the opposite sex, since I do it all the time! I'm a big huge hypocrite and I understand if you want to break up with me for this, but this is my hypocritical rule and I'm not changing it! "So you'll stay a woman, and my girlfriend, got it?!"

"Yes, sir," Azazel said, a sly smirk on her lips as she lazily saluted me.

"Fuck her some more, Issei-kun," Raynare said with eagerness, having finished lapping up all my cum.

I did as directed.

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