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Sterling Stories
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Sterling Stories
I write erotic literature! Mainly femdom and feminization themed, but I don't limit myself to just those topics. Finished stories can generally be found on LushStories, https://www.lushstories.com/profile/SamanthaJackson/stories
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[EXCLUSIVE] Alice's Wonderland: Chapter 12: Endings And Beginnings

Alice says goodbye, but does she really?

"Good morning!" Laura said cheerfully as she served me a tray of food. "You must be starving, considering you slept ever since that hypnosis role-play we did yesterday. It seemed really intense!"

"Hypnosis?" I asked confusedly. I couldn't remember much about what had happened the day before.

"Oh, I get it," Laura said with a wink. "Either way, eat up! Alice should be arriving soon."

Alice, today?  I thought as I chewed on a sandwich. But wasn't she here yesterday? I swallowed the food, and asked, "I thought you invited a guy over for today?"

"I did, and he'll be arriving too, don't you worry," Laura teased. "Alice will only be here temporarily to doll you up."

I tensed up. "Doll you up". The words echoed in my head. Like a progress bar slowly creeping its way to completion, I could feel it slowly taking over. A moment of panic set in as I started to realize what was happening.

"Laura," I blurted out. "The hypnosis-"

"Yes, Doll?" Laura interrupted smilingly.

I tried my best to fight it and warn Laura, but her second mention obliterated my ability to resist. Once again, I found myself no longer in control, but a mere passenger in my own body.

Laura observed how my body language became static and how my eyes stared blankly forwards. "You want to play already?" Laura asked, surprised. "First, eat. You'll need to recover some energy before we start, silly girl."

Without a word, I continued eating.

Laura patted my head. "Good girl," she chuckled.

A smile appeared on my face as I felt a spark of joy. I don't know why I was being rewarded for doing such a mundane task, but I wasn't going to question it either.

"Finish your food and wait here," Laura said. "I'll start getting ready as well." She got up from the bed and walked off to take a shower.

I continued eating my food until the tray was empty, save for a few crumbs, and placed it beside me on the bed as I moved to the edge of the bed. Remaining on the bed, but also being ready to leave at a moment's notice if requested.

After a few minutes had passed, the doorbell rang.

"That must be Alice," Laura yelled from the shower. "Be a doll and open the door for her."

Without hesitation, I left the bed and hastily walked off to open the door.

"Heya, Doll," Alice said as soon as she saw me. "Thanks for opening the door." She patted my head and walked past to hang her coat on the coat hanger. "Today is going to be an eventful day, so let's get to it. Close that door and follow me!"

Alice led the way back to the bedroom, where she made me undress. "I stopped by at work for a quick purchase, just for you," she said as she started emptying a shopping bag she had brought with her.

Out came a skirt and crop top, both in blue and white colors. It resembled a cheerleader's outfit, except this version was purposefully refraining from being modest. Besides the outfit, there was also a blue thong, the front of which was way too small to possibly cover my chastity cage, and white knee-high socks with blue horizontal stripes.

"This will be for you," Alice said, smilingly. "I know the thong won't cover that cage of yours, but that's the point. I want to see it dangling outside of it, freely swinging when you get fucked." She paused in thought. "Not that I'll be here much today, but you know what I mean." 

"Hey Alice," Laura suddenly said. She had finished showering and was standing at the door of the bedroom. She had already blow-dried her hair and dried herself off, but she was still naked, apart from the towel she was wearing, which barely covered her intimate areas.

"Hey Laura!" Alice responded cheerfully. "I brought along an outfit for Sammy today, I figured you and your companion might enjoy seeing her dolled up in it."

Laura looked over and giggled. "I'm not sure if my 'companion' is much of a sports person, but I can imagine he'd be more enthusiastic about fucking my little doll if she were dressed like that. Thanks for bringing it along."

Laura walked over to her wardrobe to grab some clothing and underwear when Alice interjected.

"Before I forget, again," Alice said. She reached into her pocket to reveal Laura's phone and placed it on the nightstand. "I accidentally took it with me yesterday," she added. "I only realized last night when I went to bed and wanted to set my alarm that I put someone else's phone in my pocket."

"I figured as much," Laura said and winked. "Don't sweat it. I knew you'd drop by again today, so I wasn't too worried about it." She left the room again, carrying the items she selected from her wardrobe, and said, "I'll get dressed and do my makeup and hair, you go and have fun with Sammy. Our play date won't arrive for another hour at least!"

"Another hour, huh?" Alice said with a smirk. "I reckon I only need half of that to get you ready..." She slowly paced around the room in thought. "Ooh!" She eventually said, and chuckled. "I know exactly how I'm going to have fun with you..." 

She walked up to me to show me her phone. "Just so you know, I copied yesterday's entertainment onto my phone as well. Mainly just to add to my collection of memories of our fun activities," Alice said and winked. "Just make sure to remain friends with me and occasionally drop by after today. I think we'd both dislike becoming strangers to one another."

Alice paused for a moment, but I gave no response. She stared me down with a look that felt like a mixture of hopeful anticipation and annoyance.

"Ah, you know what," Alice finally sighed. "I may have overdone it a little bit with the whole hypnosis thing. It's no fun when you're completely obedient. There's no struggle, no difficulty... It takes away all the fun of teasing you." With a defeated look, she leaned in close and whispered, "Wakey, wakey."

Slowly, I felt myself regain control of my body. I figured I had two options now. I could try to run and warn Laura, and likely be put under again before I even made it out the door... Or I could play it safe, and tell Laura about it later... Alice no longer had the keys, but she still had plenty of blackmail material, so playing it safe seemed like the better option.

"I know I have a habit of getting too excited and taking things too far," Alice said. "But I also try to make things right when I can... So how about you drop by the store sometime next week, and then I'll see to it that those hypnosis triggers get dismantled?"

"No tricks?" I asked.

"No tricks," Alice answered truthfully. "I can't promise they'll leave you completely unaffected, but I should at least be able to greatly reduce their effects. As much as I enjoyed being in control, you deserve to live your own life too." She paused briefly. "Especially since it's becoming time for us to go our separate ways... Apart from the occasional shenanigans," she added, teasingly waving her phone around.

"As long as it doesn't get in the way between me and Laura," I replied. As much as I desired to be back with Laura, and put the strange adventures with Alice behind me, I had to admit I kind of liked the various experiences she introduced me to. They weren't always that amazing, but I would likely never have experienced them otherwise. 

"I won't use the command on you anymore," Alice said. "No promises on your girlfriend, though." She winked. "But don't worry, if she does, it will only last until you fall asleep or pass out. So, regardless, you can come visit me tomorrow morning, or any other day, and we'll get that stuff deprogrammed."

"Knowing my luck, she'll say it every morning as soon as I wake up," I said, rolling my eyes. "She's notoriously bad at handling being in control."

"Now there's an idea," Alice said with a giggle and started walking to the door as if she was going to suggest it to Laura. But before she got to the door, she stopped and laughed softly. "Nah, I'm kidding. I've had my share of fun with you, for the time being. You're Laura's toy now." Alice smiled.

"At least it won't be as extreme as what you've put me through. Laura is a lot more vanilla," I said.

"I'll be honest with you," Alice said as she looked over her shoulder. "I think Laura might actually be into that stuff too. I feel like she would enjoy experimenting a bit with you. She just needs a little bit of help getting there." She winked. "I won't force anything on your relationship, but if you'd both like it, I'd be open to lending my expertise."

I blushed. Laura? Kinky? I couldn't remember us ever doing anything other than the generic sexual things, and she had never mentioned wanting to experiment with more... 'niche' things before. "I'll talk with her about it," I said after giving it some thought. "But only after you've helped me get rid of those hypnosis triggers."

"Fair point," Alice nodded and grinned as she continued, "Now, let's get you ready for your play date. I want to make sure you're ready on time, and still have a little bit of time for some fun of our own."

The next half hour or so was spent getting me ready. Alice couldn't help herself but giggle as she made me put on the thong and ordered me to pull the front to the side so that the cage remained fully exposed. After that, she went back to business by helping me in the cheerleader outfit and expertly covering my face in makeup and giving me a high-school cheerleader look, as she described it. She then restyled the extensions in my hair into twin tails, which she teasingly referred to as handlebars.

"Alright," Alice said as she took a step back. "I think that about covers it all. I'll just go and grab some final things, and then you're set. Stay here, D-... Dear," she quickly corrected herself.

I sighed in relief and awaited Alice's return as she rushed out the door to grab something from her car.

When she came back, she brought along another bag of items. "I forgot to bring this one in earlier," she said, as she repeatedly sprayed me with perfume. The scent was very strong and typically feminine. "Now you smell the way you look," she said with a grin. "Like a hot slut."

I blushed and tried to look down to evade eye contact, but Alice quickly lifted my chin and stared straight into my eyes.

"There's the Sammy I love," she said. "Pretend to be shy and embarrassed all you like, but we both know you love this. I think you're not even ashamed of the act itself... You're just ashamed of how much you love it."

"Maybe," I said shyly and pursed my lips as I shifted from one leg to another.

"Adorable," Alice said as she turned back to her bag, and removed several ropes of various lengths, and placed them on the bed. "These are for a bit of quick fun before our guest of honor gets here. Don't worry, I'll take them off before I leave."

Having walked to the dining room to grab a chair, Alice brought it into the bedroom, made me sit on it and proceeded to tie my legs to the feet of the chair, and my hands to the back of the chair's support. Satisfied with her work, she put all but one of the remaining ropes back in her bag.

"Hey, Laura?" Alice asked loudly from the bedroom. "How long do you still need?"

"Just about finished!" Laura replied. "I'll be right there!"

Alice turned back to me. "Alright... ready for a little fun?" she asked, sporting her usual devious grin.

"Not like I have a choice," I replied.

"Right you are," Alice said happily as she spun around and opened Laura's lingerie drawer. After a bit of searching, she settled on a dark blue pair of panties, which she brought back to me.

My look became confused. "You already made me wear a thong, AND my legs are tied. Why are you bringing that here?"

"Because you talk too much," she giggled as she forced my mouth open and pushed the panties in my mouth. "Try not to drool on your outfit, it would make a bad impression on your valuable guest."

"Alright, I'm done! What's up?" Laura said as she entered the room. She was dressed in a loose top and denim hotpants. "Oh... Well, what have we here?" she grinned as she slowly approached me.

"Well, you did tell me to have some fun with Sammy as well, so I did," Alice chuckled as she stepped aside to let Laura approach.

Laura now stood in front of me and trailed her index finger down my chest seductively. "Hey there, darling," she teased as she looked into my eyes. "Is this seat taken?"

"Hm!" I mouthed past the panties.

"Great!" Laura said as she grabbed my shoulders and planted herself on top of my lap and started slowly inching herself forwards, grinding against me as she kept her eyes locked on mine.

"Look at you go," Alice cheered on. "Mind if I take it a step further?"

Laura turned her head towards Alice and asked, "What'd you have in mind?"

Alice pointed at the single rope on the bed and asked, "I assume you have a wand, right?"

"The vibrating kind, or the magic kind?" Laura responded laughingly as she got up.

"Numero uno," Alice replied.

Laura walked to the nightstand to retrieve her wand, and gave it to Alice.

"Thanks, dear," Alice said, as she grabbed the rope and lifted my cheerleader skirt. She pressed the wand against my cage while pushing it against my leg, and wrapped the rope around them to keep the wand in place. After she finished, she pressed the power button and watched as I started squirming in the chair.

"And with that settled..." Alice said suspensefully as she walked toward Laura, placed her palm flat on her chest, and gently pushed her onto the bed, causing Laura to let out a surprised yelp.

Alice turned to me one last time to wink at me, before turning back to Laura and crawling on top of her. She flipped up Laura's loose top and started playing with her breasts.

Laura grabbed hold of the bedsheets as she started moaning softly.

Alice moved on to gently circling Laura's nipples with her fingers to tease her as she kept on moaning.

It didn't take long for Laura to take matters into her own hands and grab Alice's head. Alice instinctively knew what Laura wanted and placed her lips around Laura's nipples, giving each of them a gentle sucking, licking, and some playful biting.

But Laura was not the only one moaning, as, while Alice was laying claim to Laura, Laura's wand relentlessly buzzed away against my cage. And as Laura moaned, most of my view consisted of Alice towering over Laura, asserting her dominance over both me and Laura at the same time.

Hearing my moaning, Alice decided to take her teasig to the next level by sitting upright on top of Laura's crotch, dry humping her as if they were both naked and Laura was wearing a strap-on, moaning as she was doing so. Laura quickly caught on and joined in, grabbing hold of Alice's waist, and making grunting noises as she pretended to fuck Alice.

My muffled moans became louder and louder as my struggling in the chair became more violent as well. The chair started rocking sideways as I struggled to remain still. I could feel my climax nearing, and there was no way of stopping it.

Without even bothering to turn around, Alice said, "What's the matter, Sammy? Are you about to cum? Don't you just wish you were on this bed instead?" She paused shortly, but then continued, "I wonder, would you rather be in Laura's position... or mine?" she giggled.

I briefly imagined the possibilities. Getting payback for all of Alice's trials and fucking her, or riding Laura and shooting my load onto her chest as I bounced on her strap-on... With that final thought, I realized I had reached the point of no return and tensed up. Thankfully, Alice had left my skirt flipped up, so when I came, I did not make a mess on the skirt. Instead, with the continued stimulation of the wand, I spurted out several ropes of cum in front of me. Some still landed on the chair, but the skirt itself remained completely clean.

From the way my moaning had changed into a series of groans and heavy panting, Alice and Laura realized what had happened and brought their show to an end. Alice bent down, bringing her face down to Laura's, and kissed her on her lips, much to Laura's surprise, which caused her face to briefly become flushed. Alice then got up and left the bed, walking over to me to examine the fruits of their labor.

"My, my," she said in admiration as she turned the wand off. "Looks like you sure were a very 'excited' cheerleader!" She grabbed some tissues to quickly wipe the chair and my cage as clean as she could, before moving on with wiping away the cum on the floor and throwing the dirty tissues away.

Having disposed of the dirty tissues, Alice returned to me and kneeled in front of the chair. She loosened the rope tying the wand to my leg and removed it. She then looked up at me and said, "Thanks for joining in on the fun, cutie," and planted a kiss on my cage before lowering the skirt back down, removing the panties from my mouth, and further untying me from the chair.

Putting the ropes back in her bag, Alice thanked Laura as well for her participation in the impromptu activity and said her goodbyes. "Don't forget to drop by next week, Sammy! And have fun, you two!" Alice said, and turned to me, saying, "I hope you have enough energy for round two. At least you should be able to last longer now."

Laura accompanied Alice to the front door and hugged her. "Thanks for the help, darling," she said. "You think you could maybe teach me a few tricks too, eventually? I mean, if you're not too busy."

Alice giggled. "Funny you mention it," she said. "I told Sam earlier that I would be more than willing to do exactly that! Feel free to contact me whenever. You have my number!" And with those final words, Alice left the building.

Laura returned to the bedroom and kissed me on the cheek. "I've always wanted to be a bit more adventurous," she confessed. "But I was always too insecure about it, so I asked Alice to teach me a few things. I hope you don't mind."

"Of course not," I replied. "I'd happily experiment with you, as long as we can keep the more extreme things private?" I let out a nervous laugh.

"Of course!" Laura said. "Nobody needs to our naughty little secrets... unless, of course, we both agree to include others in some adventures." She giggled and suggested moving to the living room to watch TV and cuddle while we await the arrival of our special guest.

"When is he arriving, anyway?" I eventually asked.

"Between 14:00 and 16:00," Laura replied. "But I have to admit, it might be a bit improvisational."

"What do you mean?" I asked.

"Let's just say there's a reason I asked Alice for help. I was too afraid to ask people I knew, so I kind of winged it, and I'm hoping for the best."

"Oh, okay?" I replied with a nervous chuckle. I realized Laura was feeling a little guilty, so I tried to comfort her and added, "Well, I trust you, so whatever your plan turns out to be, I'll support it."

We continued cuddling and waching TV, and a while later, the doorbell finally rang.

"That might just be him," Laura said anxiously as she jumped up and went to the door. I carefully followed behind her, but remained mostly out of sight, peeking just around the corner out of curiosity.

Laura opened the door and greeted the man, he was dressed like a mail delivery person and carried a small, wrapped package and a clipboard.

"Hi there, I've got a package for Sam," the man said.

Why is he dressed like a delivery guy?
I thought. And did he really do that just to make a pun about packages? What a strange guy... Where did Laura even find this person?

Laura nervously tried to lure him inside, saying, "Sam's inside, you can give her your package personally."

The guy shrugged and stepped inside. As he entered, he saw me and started walking toward me, but stopped dead in his tracks when he heard the door shut behind him.

"Why don't you call your boss and say you got stuck in the elevator?" Laura suggested lustfully as she had quickly moved up behind him and pressed her body against him.

"I beg your pardon?" The man said nervously, breaking out into a spontaneous sweat.

It was only now that I realized what Laura meant with her improvised plan. The man she lured inside was an actual delivery man! A mixture of feelings erupted, and I wasn't sure what I was supposed to think. Was this amusing? Embarrassing? Arousing? Or something else entirely? I couldn't decide. All I knew was that Laura had started her improvised plan, and I had to support her.

I slowly emerged from behind the corner and approached the delivery guy as well now, trying to pull off a seductive walk. "Please, mister," I said, trying to sound as feminine I could. "You said you had a package for me, and I REALLY want it." I dropped to my knees in front of him and stared up at him in anticipation.

"I, uhm," he stammered. "Oh dear."

"Look at how desperate she is," Laura pleaded. "We promise it won't take long."

Deep inside I knew I was originally doing this for Laura and only pretended to be desperate for this random guy's dick, but when Laura called me desperate, I felt humiliated. Not in a shameful way, but in a slutty, arousing way. Suddenly, I felt like I actually wanted this guy's dick in my mouth, and I found myself reaching for his belt.

"Please, mister," I repeated as I unbuckled his belt.

The delivery man's breathing became heavier. "Alright, alright," He finally said. "Just let me text my boss that I'm delayed, but I really can't make this long."

Laura cheered, "Don't worry, sir, this slut will have you drained in no time!" She ran off into the bedroom to fetch her strap-on and put it on so that she could join in on the activity.

Meanwhile, in front of me, the man had already dropped his pants, and I was staring right at the bulge that was growing from inside his boxer shorts. Seeing Tyler's dick many days ago was an entirely different feeling than what I was feeling today. It probably was the fault of the hypnosis booth and all those videos, along with Laura's encouragement, but I sensed that my mouth was watering as I eagerly pulled down the man's boxer shorts.

The man's dick was roughly 5 inches and already seemed to be erect. Thankfully, he wasn't as big as Tyler or the training models Alice had used, allowing me to feel more confident in my ability to accommodate his member in my mouth without making a scene. I shifted my body to be on all fours and arched my back as I moved my head forwards, but as my lips opened up to slowly accept the man's dick, he grabbed hold of my twin tails and pulled me in all the way, until my nose flattened against his skin.

"Sorry, dear," He said matter-of-factly as he rhythmically continued pulling my hair back and forth. "But I'm on the clock."

All I could respond with, was to give him a thumbs-up as my head kept bobbing up and down his shaft. There was nowhere I'd rather be... Well, besides Wonderland. Though, in my current state of mind, I'd rather have another go at that high score than deprogramming myself.

Laura exited the bedroom again, wearing her lubed-up strap-on. She saw me on all fours, already servicing the delivery man, shook her head, and said, "She couldn't even wait for me to get ready? Must've been having cock-withdrawals." She walked up behind me and gently raised my skirt, so as not to give away my secret to the delivery guy, and pulled my thong slightly further to the side to slowly push her strap-on inside me.

"There you go, darling," Laura said as she slapped my ass. "Does that satisfy your cock craving?"

"Hm-hm," I mouthed, as my head was still being pulled back and forth by the man in front of me.

"So," the man said, looking at Laura. "Is this something you two do more often? Or?"

"It was her Valentine's Day surprise," Laura said as she placed her hands on my waist and picked up the pace. "It's our first time trying this, actually." She giggled and admitted, "If you weren't game, I'd likely just have taken her clubbing instead."

"I guess it worked out well then," the man said laughingly. "I have to make it quick, so your friend gets to have my cock, and you'd still have time to go clubbing later!"

"Maybe," Laura giggled, moans occasionally escaped her lips as she fucked me. "I still want to get my own orgasm and fuck this bitch silly in the process."

"Fair point," the man said. From the way he spoke, it was clear that he was getting closer and closer to an orgasm. "You young ladies have the time to properly enjoy each other." He said and let go of my hair, only to instead grab hold of the back of my head, pulling it towards him as closely as he could. He tensed up, and his balls contracted, a rope of sperm shooting down my throat with every break in his speech as he grunted, "I, on the, other hand, am, running, late."

The man kept me locked in place even after he finished his orgasm, looked at me, and said, "Would you kindly lick it clean when I pull it out? I can't have my work uniform get stained."

I made my best effort to nod, and he slowly let go of my head as I swirled my tongue around his shaft and glans while slurping it as clean as I could. When I finished, I proudly showed him my open mouth, before swallowing the final remnants of his cum and showing my empty mouth, as proof of my gratitude for his cooperation.

All the while, Laura had not stopped fucking me with her strap-on. Granted, she did slow her pace down for me to focus on 'the task at hand', but she now seemed to be impatiently waiting for the man to leave so that she could return to use me at her leisure.

After the man finished up, made himself presentable again, and thanked us, he quickly left. And as the door fell shut, Laura reached to grab each of my arms. "Try not to fall," she said as she pulled on my arms and I started falling toward the ground, only to stop suspended slightly above the floor by the force pulling on my arms.

Laura increased her pace again as her moans started sounding more aggressive. She was no longer holding back for the sake of others and took what she desired. "The impromptu threesome was a nice experiment, and I'm glad it worked out, mostly," Laura said, panting. "But I much prefer to have you to myself." She temporarily paused fucking me and leaned in as close to my ear as she could and quietly growled, "So I can use you to my heart's content."

Hearing her say that so animal-like gave me a shiver, and Laura responded by lustfully nibbling on my ear to further drive home the point that she was in complete control now. Returning to her earlier stance, she continued fucking me as the other end of the strap-on slowly brought her closer to her much-desired orgasm, too. 

A few minutes later, Laura and I were both moaning at the top of our lungs as we reached our climax. I figured I was following closely behind her and that I'd likely cum during or shortly after her orgasm. But suddenly, Laura gripped my cage and said, "You already came today, remember? Now it's my turn... So be a good girl and don't be so greedy. Hold it in for me."

Part of me now felt even more aroused and ready to burst, but, at the same time, I felt an even greater sense of duty to withhold my orgasm and hold my 'good girl' title, so I focused all of my energy into denying my orgasm while Laura achieved hers.

I didn't entirely succeed, as I was already overstimulated, so, instead of reaching an orgasm that I could enjoy, I simply ended up leaking out of my cage. It was frustrating to know that I came, but didn't get to feel the euphoria of an orgasm.

Laura took notice of the cum leaking out of the cage onto her hand and cooed, "Awh, did someone just have a ruined orgasm?" 

I quietly nodded in embarrassment. 

"That's okay," Laura said understandingly and giggled. "As long as they're ruined, you can have as many orgasms as 'you' want... Well, under one condition." She waited until I stopped leaking before removing her hand from my cage, and slowly got up as she pulled out her strap-on. She walked around to my face and crouched, lowering her cum-soaked hand in front of my mouth. "If you swallow the evidence, I'll pretend it didn't happen," she said mischievously and winked. "It'll be our dirty little secret."

I felt like the Laura I knew and had been dating for countless of months, had practically evolved overnight. This Laura was a lot naughtier and kinkier, which was both a welcome surprise and something to fear, as I could not yet tell where it would lead our relationship. Though, to say I was curious to find out how deep the rabbit hole went, would be an understatement, as I was more than willing to partake in this shared adventure.

Obediently, I gently licked Laura's hand, but we both quickly realized that my cum did not want to transfer easily from her hand to my tongue, so Laura instead commanded me to open my mouth, so she could wipe her hand on my lips to more easily return the cum to me. 

"There. That's better," Laura said encouragingly as I swallowed my cum. She got up and reached out with her clean hand to help me up. "Let's shower and get back in some regular clothes," she said. "Do you want to order anything? And let me help you out of those clip-in extensions."

"Actually," I said shyly. "Mind if I leave the extensions in? I kind of like them."

"Of course!" Laura cheerfully responded. "Whatever you feel happy with."

"On that subject..." I continued. "Would you be okay with sharing your wardrobe with me more often?"

"Sure!" Laura replied. "If you want, we could even go shopping sometime to get you your own 'special' collection," she added teasingly and winked. 

"Shopping... Special collection... You mean at Wonderland?" I asked flushed.

"Hm-hm," Laura hummed and nodded. "But we can cross that bridge when we get there. First, let's shower and enjoy the remainder of our Valentine's Day," she said as she kissed me and pulled me into the bathroom with her, locking the door behind her...
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Sterling Stories

[PREVIEW] Alice's Wonderland: Chapter 12: Endings And Beginnings

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 Share A Drink With: Chapter 2: Elizabeth

Spin the bottle, and let the bottle spin you.

"Ugh, I'm still sore from last time," Stephany groaned. "Can we skip today and just play again next weekend?"

"How about we spin first and then decide?" Jeff argued. "Besides, you can always spin the safety bottle."

"Alright, alright," Stephany said after giving it some thought. "This time you're spinning the bottle, though."

"That's fine," Jeff said, grabbing a bottle. "You want to share it again or drink it by yourself to numb your soreness?" he asked laughingly.

"Sure, I'll have it," Stephany said. "I could use a liquid painkiller."

Jeff poured the beer into a single, glass tankard and gave it to Stephany. He then placed the empty bottle between them on the floor and spun it. Once again, it came to a halt, facing mostly toward Jeff.

"Next time it should land on you. These odds are rigged," Jeff joked, grabbing the bottle. "Today's winner is..." he said dramatically as he slowly removed the paper from it. The smug smile on his face made way for a look of confusion. "Elizabeth? Oh boy..."

Stephany giggled and curtsied. "Your Highness."

"Yeah, let's not go there," Jeff responded with fake retching at the thought. "I hope you can also imagine someone else when you hear that name."

"Hm," Stephany hummed in thought as she took a sip of her tankard. "Honestly, I'm not sure," she said. "It strikes me as a very 'girl-next-door' kind of name."

"So..." Jeff hesitantly said.

"So," Stephany said. "We can just take it easy with that one. No need to spin your safety bottle... Unless you insist on making it sexual." She giggled.

"No, no," Jeff quickly replied. "A casual play sounds good to me!"

"Alright," she said. "In that case, I guess we can do it today then, instead of next week. Let's just have a fun, casual day indoors." Stephany finished her tankard, got up, and started walking out of the living room.

"Where are you going?" Jeff asked.

"The bedroom, of course," Stephany replied. "I'm going to have to check my wardrobe to see if I have anything that could resemble Ellie's style. Because you 'are' going to become Elizabeth, those are the rules." She giggled as she left the room.

Jeff gulped and mumbled to himself, "Maybe we should have shared that beer after all..." He poked his head out of the doorway and said, "I'll calm my nerves with some phone games on the couch while you do your thing!"

"Nuh-uh!" Stephany replied from the bedroom. She jolted into the bathroom and returned to the living room with a body trimmer and handed it to Jeff. "You, Ellie," she said sternly, "can help prepare yourself by trimming those unsightly body hairs down."

"But," Jeff stammered.

"No buts," Stephany said. "Ellie is not going to half-ass her looks when she goes out to visit her friend."

"Yeah, but, what about work?" Jeff asked, concerned.

"I'll go easy on your eyebrows," Stephany said, comforting. "But the body hair has got to go. If anybody cares enough to ask, you can say you lost a bet with me or something. It'll grow back soon enough, don't worry. Or did you think I only shave my body once a year?" she chuckled and left the room again.

Great, Jeff thought as he took off his shirt and started trimming his upper body. Hopefully next time, it'll be her turn to do the role-playing. At least we'll be taking a few days off after today... In hindsight, with these stakes, it's a bit too risky to play this game on both weekend days, but I can't back out now. At least it's not going to get sexual. That would be so awkward. Jeff shivered.

"How's it going over there?" Stephany asked from the bedroom.

"Just finished my upper body, moving on down now," Jeff replied.

"Alright!" Stephany said. "Just, please, only trim your legs and then use a razor in the shower for your more private areas. Hygiene reasons."

"As if I was going to let an electric blade get anywhere near my groin!" Jeff replied.

"Better safe than sorry," Stephany commented. "I'm nearly done here, too. I put together a few outfits, and then I'll let you choose what you'd feel most comfortable in."

"Is it too late to run out the door and hide for the day?" Jeff joked.

"I mean, if you're not going to be Ellie today, then we'll just have to do it tomorrow," Stephany said matter-of-factly. "Should I call your boss to let him know about his new female employee?" She giggled.

"Today's fine!" Jeff quickly replied.

"Glad to hear that, Ellie," Stephany said laughingly. "When you're done trimming, join me in the bedroom to pick out your outfit before you head for the shower."

Jeff finished trimming his legs and approached the bedroom. "Should I be afraid of what I'm about to see?" he teasingly asked as he entered the room.

"They're just clothes," Stephany said and laughed. "If that scares you, wait till you see the makeup kit!" She pointed at the bed, where she had laid out several clothing sets. "So, for the first option, we have some regular blue jeans, you can choose between either the full-length or short jeans, accompanied by a white blouse and white heels."

"You do remember I'm two shoe sizes bigger than you, right?" Jeff asked.

"They've got some extra space. I'm sure we could squeeze you in there," Stephany answered. "It might be a little uncomfortable, but it's just for a single day, you can handle it!" She moved on to the next set. "Up next, we have something a little more girly. A short, lightish-red dress, with a black jean jacket, black pantyhose, and black pumps."

"Not gonna lie, it does look kinda nice. You should wear that set sometime!" Jeff said.

"Duly noted," Stephany chuckled. She moved on to the final set. "If you want to be truly boring, you could also go super basic and choose this outfit. Simple blue jeans, white sneakers, and a grayish cashmere sweater."

"I mean, I know I complained, but I can hardly role-play Elizabeth if I don't 'feel' like an Elizabeth," Jeff said. "I'll probably regret saying it later, but even though the last set is the safest and easiest way out, my gut says it should be one of the first two options."

"I was hoping you'd say that," Stephany said happily. "You won't regret it! I'll turn you into a real cutie!"

Jeff blushed. "Me? A cutie? Have you seen these shoulders and arms?" he asked with a hint of sadness.

"That's why I made sure to include ways to cover it up a little," Stephany said. "You'd hardly notice them! I'm more concerned with hiding that package of yours." She giggled.

"Wh- What's that supposed to mean?!" Jeff stammered, blushing even harder now, doing a double take to ensure he wasn't sporting a boner unbeknownst to himself.

"Well, you've got to change underwear too, of course!" Stephany elaborated. "And I don't want you to rip through my undies!"

"Oh, like that," Jeff said.

"Thankfully, I've got some medical tape that I can use to tape it all down and flatten it a bit," Stephany said matter-of-factly. "That's why you need to make sure it's all shaven smooth down there. Otherwise, the tape removal is going to hurt even more at the end of the day."

"Noted," Jeff said, slowly exiting the room by walking backward. "I'll head to the shower and take care of that, then. I'll leave the picking of the underwear to you, lest I faint before we've even started."

"Sure thing, cutie," Stephany chuckled. "Oh, and use my shower products! Ellie is not going to smell like 'Woodland Enigma'."

"Actually," Jeff said. "It's 'Wild Temptation'."

"Same thing, different name," Stephany said and shrugged. "You're using my Fruity Passion soap today. And when you've dried yourself, use my deodorant and perfumes." She paused. "Actually, I'll use those on you, lest you empty my entire bottle."

"Probably for the best," Jeff said with a chuckle from the bathroom as he closed the door behind him.

Stephany returned to the bed and looked at the clothing she had laid out.

"Hm," she pondered. "Basic girly or cute girly?" as the words left her mouth, she realized that going with the latter was the only real option, and put the other two outfits back in her wardrobe. "Alright... underwear," Stephany said aloud as she opened her drawers. "Well, given the dress, red would make the most sense, but that's also more... sexual? Black might fit better in that case, and the rest of the outfit is black too..."

Stephany took a moment to weigh her options, but eventually decided to stick with red, as it would be less likely to show beneath the dress. "Ellie can be cute and sexy," she smilingly said as she picked out a red slip containing a simplified, monochrome print of butterflies and combined it with a simple red push-up bra. She may stand out a bit more than a 'girl-next-door' would like to, Stephany thought. But I have an obligation to make Ellie feel like a woman today, even if that means using some encouragement.

"How's it going in there?" Stephany shouted.

"Almost done!" Jeff yelled back. Not long after, he turned the shower off and dried himself. He opened the door and motioned for Stephany to bring his outfit for the day.

Stephany energetically jumped up from the bed, grabbed the clothing and underwear, and rushed off to the bathroom, where the placed them on the top of the laundry machine.

"The more time that goes into this, the more I'm glad we're not making it sexual this time," Jeff said, looking at the underwear Stephany choose for him.

"I mean, if you were a little more confident, it could have led to you doing me," Stephany teased. "But if you're just going to be shy and submissive like that..." Her face displayed a smug grin.

"I'm just not used to... this," Jeff said, holding the red slip. "At least, not to wearing it myself."

"If you hold it next to your face, I'm quite certain it could act as camouflage," Stephany giggled. She grabbed the medical tape from the mirror cabinet. "Alright, time to conceal your firearm," Stephany joked as she kneeled in front of Jeff to start applying the tape and apologized. "It could have been a once-in-a-lifetime opportunity to say that, I had to take it."

"I'm happy at least you're having fun," Jeff said, embarrassed. "Can you hurry it up a little?"

"Is Ellie afraid she's going to get an erection?" Stephany teased.

"Oh shush, you know I'm just easily aroused when you touch me there," Jeff blurted out.

Stephany giggled as she continued applying the tape. "And... Done," she said reassuringly a few moments later as she finished taping Jeff's scrotum and penis to the skin, making it look as flat as she could. "Next time, I'll buy some pads to help with the flat look," she said. "But for today, this will have to do."

"Next time," Jeff repeated. "Let's hope that's going to be many months away."

"Loser accepts their defeat without complaints, those were the rules," Stephany said matter-of-factly. "You had your fun yesterday, now it's my turn." She smiled. "Now put these on and see how they fit," Stephany said as she handed Jeff the red slip and bra.

Jeff hesitantly put them on and said, "A bit tight, but they fit."

Stephany walked around to Jeff's backside and checked the fit. "Looks just fine to me, Ellie," she said and slapped his butt.

"Hey!" Jeff shrieked. "I thought we were going to keep it casual today?"

"We were going to keep it non-sexual," Stephany corrected. "A little bit of flirting and teasing my cute little Ellie still seems within the realm of allowed activities."

"Ellie will remember this," Jeff said.

"Oh, so Ellie is a gamer too, now?" Stephany giggled as she sprayed some perfume on Jeff and handed him the dress and pantyhose. "Put on the maid outfit, gamer girl."

"Maid outfit?" Jeff responded confused and paused. "Oh. Right. I sometimes forget you speak meme, too." He rolled his eyes but proceeded to put on the clothing regardless. "Hey, Steph?" Jeff asked. "Are you sure this dress is long enough?"

"Barely, but, yes," Stephany replied. "It was not meant for someone your size, but it still works out, your ass is covered."

"Barely," Jeff repeated as he shifted about. "I can feel the breeze coming through."

"Want to go out and buy a bigger one?" Stephany teased.

"As a matter of fact, this dress fits perfectly!" Jeff quickly replied.

Stephany giggled. "Glad to hear that, Ellie," she said. "Now let's get back to the bedroom, so I can do your makeup and finish your look."

Stephany grabbed Jeff's hand and led him to the bedroom, where she brought him to the bed. "Sit," she instructed, as she gently pushed him onto the bed. She walked off to grab her makeup bag and opened it to reveal several small glass containers containing liquid makeup, brushes, pencils, and other items Jeff could not decipher.

Jeff anxiously let Stephany apply the makeup to his face, apply and brush powders, curl his eyelashes, rework his eyebrows, which she promised not to overdo, and draw around his eyes with an eye pencil.

"Are we done now?" Jeff asked. "My back is starting to hurt."

"A small price to pay for beauty," Stephany argued laughingly. "But, yes, I'm pretty much done. Dare to take a look?" She stepped aside so that Jeff could look at himself in the standing mirror that was behind her.

"That's... me?" Jeff asked, astonished. "I knew makeup could make a lot of difference, but, damn! I never imagined it could make me look even remotely girly!"

"Thank you," Stephany said with a curtsy. "So, I take it you like it?"

"I mean, it looks amazing, and it's perfect for Ellie," Jeff answered. "But I don't see this as a style for 'Jeff'. So I'm feeling a little conflicted."

"Well, luckily Jeff isn't here today," Stephany giggled. "So I'm glad to hear Ellie likes her look... One last thing, though!" She rummaged through the makeup bag and pulled out some lipstick. "These don't smudge easily, and they match your outfit," she said as she applied the lipstick to Jeff's lips.

"So, now we're done?" Jeff asked.

"The day won't be over any faster if you keep asking," Stephany replied. "Your makeup is done, but your hair still needs some work."

Stephany walked over to her wardrobe, where she opened a box containing various blonde and brown wigs. After removing a few, she found one she was satisfied with.

"This'll do nicely," Stephany said, holding out a dark blonde wig, its hairs were long and wavy. "Thankfully, your hair is short, and its color is similar to this wig, so we can just put this over your natural hair without having to make any adjustments," she said as she walked behind Jeff to pull the wig over his head.

Jeff had mostly just kept staring at himself in the mirror while this happened, trying to process how his appearance had changed so drastically in just a single day. It was like he stared at a completely different person, yet, he was staring at none other than himself.

"There," Stephany said. "Now you're done." She grabbed the black jacket that she had left on the bed and handed it to Jeff. "Now put this on along with the pumps and then Ellie will be fully dressed," she said with a smile.

"Indoors, though?" Jeff hesitantly asked as he took the jacket from Stephany.

"We can also go outside with it if you want," Stephany said and giggled. "Just put it on for the looks. If it gets too warm, you can take it off later."

Jeff put on the jacket and, with some assistance from Stephany, squeezed into the pumps, which, surprisingly, were a bit tight, but not tight enough to be uncomfortable.

"What time is it even?" Jeff asked. "I feel like we've spent half our day on just the preparations."

"Well, there's still natural light coming through the window, so it can't be that late," Stephany reasoned as she grabbed her phone to check. "Oh. It's nearly 6 already."

"I guess we'll be ordering today, then," Jeff responded. "Pizza?"

"Sure," Stephany answered. "And then we'll just watch some TV for the remainder of the day, nice and laid back."

"Say no more," Jeff said as he rushed to the living room to drop down on the couch. A long drawn-out sigh of relief escaped his lips. "Much better," he said.

"Stephany casually walked after him, absentmindedly browsing her phone. "Which pizza would you like, Ellie?" she asked as she sat down next to him.

"Uhm," Jeff said, directing his gaze at the ceiling as if the answer to her question was there. "Meat lovers," he finally said.

Stephany chuckled and slowly brought her hand to Jeff's inner thigh as she teased, "So Ellie is a meat lover, huh?" She gently squeezed his thigh as she stared into his eyes with a longing gaze.

Jeff turned red and froze up. "Steph!" was all he managed to say.

Stephany released her grip. "I'm just having a bit of fun, darling," she said laughingly and added, "I think I'll just upgrade it to a family-size pizza. I'm feeling like a meat lover too tonight." She brought her face closer to Jeff and kissed him on the cheek.

Jeff wobbled around on the couch trying to contain his nerves. "If you keep this up, that tape is not going to hold," he said.

"Let's hope it does," Stephany said. "Because you're going to open the door to accept the pizza when it arrives. I already ordered and paid online, so Ellie is going to have to open the door and bring that pizza in." She giggled.

Jeff's breathing became noticeably louder, but he remained speechless.

"I'll stop teasing you for now, for Ellie's sake," Stephany said. She threw her arm around Jeff's shoulder and gently pulled him towards her. "Here," she said reassuringly. "Lean your head against my chest, like I usually do to you. Feel my heartbeat? It's calming, isn't it?" She gently planted a kiss on the back of Jeff's head.

"Hm-hm," Jeff eventually hummed as he slowly calmed down again while they watched an episode of SuperHeroes.

Shortly before the episode finished, the bell rang, and Jeff jumped up. He knew what it meant and that it was his cue to greet whoever was at the door and bring the pizza in. He anxiously waddled his way over to the door and opened it. A person was standing in front of him, Jeff had already directed his face down to evade eye contact and instead focus on the pizza box and remove himself from the embarrassing situation as fast as he could.

But there was one issue. The person in front of him was not holding a pizza box.

"Hi!" a friendly voice said. "Is Stephany home? I was supposed to return some music CDs to her last week and I kept forgetting, but I saw her car on the driveway and I happened to still have them in my bag, so I thought I could drop by and deliver them!"

Jeff was not prepared for this interaction. His fight-or-flight response could not decide and instead froze in place like a deer in headlights. Thankfully, Stephany remained nearby to assist if needed, so she was able to quickly interject herself into the situation and take over.

"Hey, Kayleigh!" Stephany said. "Sorry, don't mind Ellie, here, she's a bit socially awkward. We were expecting a pizza delivery, so she probably froze up when she was met with a different outcome than what she had prepared herself for."

"Oh, it's fine," Kayleigh responded. She grabbed a couple of CDs from her bag and handed them over to Stephany. "Here you go, dear. Sorry for being so forgetful! And my apologies to you too, Ellie. I didn't mean to startle you." She gently put her hand on Jeff's shoulder as a means of comforting 'Ellie'. "Have a nice evening, you two!" she said as she turned to walk off again.

Just as Stephany was about to close the door, she noticed the pizza delivery car approaching from the distance. It drove up to the building and came to a stop.

Stephany grabbed Jeff's hand and said, "Sorry about that. I wasn't expecting that one either. But on the plus side, I don't think she recognized you."

"Do I still have to take the pizza?" Jeff asked anxiously.

"I'll do the talking and the interactions, just stay here with me and look friendly, that's all you'll have to do, darling," Stephany said reassuringly.

Jeff pulled himself together to muster a friendly, shy smile as he faced directly forward again to silently greet the delivery person as they approached.

"One family-size meat lovers pizza?" A male voice read from a piece of paper sticking out of the pizza box. He looked up from the paper and looked at Stephany and Jeff. "Oh, wow," he said, "Must be my lucky day, haha."

Stephany raised an eyebrow. "How so?" she asked.

"Just, uhm. Well," the guy stammered. "I don't usually get to make deliveries to cute women."

Stephany chuckled and responded, "You're just saying that to get a tip."

"No, I mean it!" The guy said. "You both look amazing." He looked down at his pizza box and comically shook his head. "Anyway, here's your pizza!" he said, extending the pizza box towards Stephany.

Stephany reached out to accept the pizza and thanked the delivery guy, giving him a small tip before saying goodbye and closing the door.

"I'm not sure who was more shy, him, or you," Stephany laughed. "Now come on, let's have some pizza, watch another episode or two, and then we remove that tape, so I can have my extra topping of meat." She winked at Jeff as she walked back into the living room.

Jeff paused for a moment before following Stephany into the living room. "Babe?" He asked as his head poked around the corner.

"Yes, Ellie?" Stephany replied as she looked up from the couch.

"The tape is already loose." Jeff shyly admitted as he walked around the corner to display his erection in the dress.

"Well," Stephany said as she closed the pizza box again. "I suppose we can reheat this and have dessert first tonight." She smiled.

"Can I-" Jeff asked.

"Nope. The dress and makeup stay on," Stephany interrupted. "Come join me on the couch, and I'll help myself to that meat topping."

Jeff did as instructed, and Stephany wasted no time in fully removing the tape. Thankfully, the tape left no sticky residue, so Stephany decided to leave it as is. "I know we said non-sexual at first... But I think we both got a bit ahead of ourselves," Stephany giggled. "So assuming it's okay with you, we can do just this one thing that we both know you're comfortable with. The only difference is that you still look like Ellie, that's all."

Jeff nodded eagerly with his flushed face and Stephany proceeded to give him a slow, sensual blowjob as the TV continued producing background noises of their show. Jeff did not last long as all the teasing Stephany had subjected him to, along with his mind constantly wandering to sexual thoughts as he couldn't shake the fact that he was wearing feminine underwear, clothing, and makeup, had already put him in a heightened state of arousal.

When Jeff climaxed, Stephany remained in place. She kept her lips wrapped around his shaft, but seemingly made no effort to swallow any of his sperm down. When he finished, she finally came up, looked at Jeff with a smile, paused, and then placed her hand on the back of his head.

Jeff's face turned from satisfaction to horror as he realized what was about to happen, but it was already too late. Stephany's lips were already locked to his, and instinctively his lips parted to kiss his partner, only to be greeted with his own salty load pouring into his mouth.

Stephany moved back and swallowed as she covered Jeff's mouth with her hand. Showing proudly how her mouth was empty, she chuckled and said, "While I was down there, I remembered that I already had my drink earlier, but I hadn't shared it with you. So I decided that, instead, I'd be sharing 'my drink' with you now."

Jeff figured that Stephany would not let him off the hook easily, and the longer he'd refused to play along, the more the taste would linger in his mouth. So he gave in and swallowed. His face went sour, and Stephany giggled.

"Clothing shared, pizzas shared, drinks shared, this truly is an amazing day. So much better than I thought it'd be!" Stephany said happily. "Now, let's put this back in the oven for a few minutes, and then meanwhile we can brush our teeth or get something else to wash away this taste."

Jeff immediately got up and rushed to the bathroom.

"Be careful of your makeup, Ellie!" Stephany shouted and chuckled as she got up to preheat the oven... 
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Sterling Stories
Public post

Share A Drink With: Chapter 1: Christian 

 Spin the bottle, and let the bottle spin you.

Stephany and Jeff had been wanting to spice up their sex life, but as neither one of them was very spontaneous, they had difficulties coming up with ways how to achieve that goal.

"Oh, I know!" Stephany suddenly exclaimed, breaking the silence in the room. "How about a game of spin the bottle, but with a twist?"

"Ha!" Jeff chuckled. "With a twist? I don't think you can even play that game without twisting the bottle at the very least."

Stephany sighed. "Jeff! Now is not the time for your witty remarks. I'm trying to be serious here." She crossed her arms and pouted.

"Alright, alright," Jeff said. He took a deep breath to recompose himself. "So, what's the twist?" he asked, scratching his head. "Don't get me wrong, I enjoy kissing you, but I'm still a little confused about how this game would improve our sex life."

"Well," Stephany started. "You know how Hoppeken released that ad recently?"

"The 'share a beer with x' campaign?" Jeff replied.

"Yes, that one!" Stephany confirmed. "What if we buy a bunch of those bottles without looking at the names, cover them up at home, and then shuffle them, so we forget which bottle had what name?"

"Okay?" Jeff said questioningly. "And then what?"

"Then we spin a bottle," Stephany resumed. "And whoever it lands on, has to reveal the name and assume the role the way the other person imagines a person with that name to be like."

"Oh, like, role-play?" Jeff asked.

"Exactly!" Stephany said cheerfully. "It could lead to fun role-play ideas, which takes a load off of our shoulders on thinking up scenarios from scratch."

Jeff thought about it for a moment and laughed. "So, like, if you land a bottle that says 'Jack', you have to role-play a lumberjack?"

"If that's what you imagine someone named 'Jack' to be like, I suppose so!" Stephany answered and laughed along. "Some bottles could lead to ways to spice things up sexually, while others could just be a bit of non-sexual fun on the side, to keep it light."

"Fair," Jeff said. "I don't know if I could recover if I had to pretend I was making love to a gay lumberjack." He shivered.

"And why's that?" Stephany asked teasingly. "Weren't you pestering me about trying out anal for the past few months?"

"I mean, yeah," Jeff admitted. "But I'm not sure if finally fucking you in the ass would outweigh the mindfuck it'd give me if you looked like a guy while we did it."

"Oh, babe," Stephany said, softly pushing Jeff. "Do you really think you would be the one fucking the big, burly lumberjack?"

Jeff's face turned red. "I didn't-, you-, I-," he stammered.

Stephany laughed. "You know I have a strap-on, right?" she teased and give Jeff a kiss on his red cheek.

"How about a second bottle?" Jeff suggested, still beet red. "If either of us is uncomfortable with the scenario, we can spin for safety. Whoever it lands on gets to decide if it's a sexual scenario or a non-sexual one?"

"A second spin in case we don't already agree on the setting?" Stephany asked. She took a moment to think about it. "Alright!" she finally said. "But whoever loses that coin toss will have to accept their defeat and play along. No sore losers!"

"Hmpf," Jeff pouted. He took a few seconds to recompose himself and added, "You just wait till you're in an uncomfortable situation and you have to swallow your pride!"

"We'll see about that!" Stephany jested. "Now c'mon, let's do our groceries and buy some Hoppekens while we're at it."

The couple got in their car and left for the store, where they placed their regular groceries in the cart and headed to the beer aisle to check out the Hoppekens.

"Haha!" Jeff laughed as he revealed one of the bottles to Stephany. "They even have a bottle to share with 'Barbie'. Can you imagine someone with that name being a beer drinker?" he chuckled.

Stephany laughed. "I guess the common names sell faster," she argued. "So we're more likely to find odd names if we just get a large number of random bottles. Anyway, what did I say about looking at the bottle names?"

"Right, right," Jeff said. "I know. I shouldn't. It'd spoil the surprise. But I couldn't resist having a quick peek. I'll stop now... How many should we get?"

"Uhm, I guess we could start with six," Stephany suggested. "If we enjoy it, we can do another six at a time. That way, we shouldn't end up having that many odd names."

"Each pick three at random, then?" Jeff asked.

Stephany agreed, and the couple finished their groceries. Upon arriving home, Stephany immediately grabbed paper and tape to cover up the names on each bottle while Jeff put the rest of the groceries away.

"Want to play one round already?" Stephany asked from the other room.

"Sure! I just finished here too," Jeff replied, entering the living room.

"Alright," Stephany said excitedly. "I covered the bottles, so, who gets to pick and spin first?"

"Well," Jeff reasoned. "It was your idea, so how about I shuffle the bottles around, and then you pick and spin one?"

Stephany agreed and turned her back to Jeff, who randomly changed the placement of the bottles. After he finished, he let her turn back around and pick a bottle.

"This one!" she said, picking a bottle from the pile.

Stephany walked to the kitchen to empty the beer into two glasses before returning. After they drank the beers, Stephany placed the bottle on the floor and spun it. It spun around for a few seconds, but eventually, it slowed down and stopped, facing Jeff.

Jeff picked up the bottle. "Alright," He said suspensefully. "Let's see what's behind door number one..." He removed the paper covering the name on the bottle. "Looks like you just shared a beer with... 'Christian'?" Jeff said. There was a pause. "Want me to do a religious role-play?" he then asked and laughed. "Lord knows it's high time for confessions to be made in this household."

"Actually," Stephany said teasingly after a moment of thinking. "I was thinking more of a certain Mr. Grey."

"Oh," Jeff said awkwardly. "Well, you'll have to help me out, then. You know I haven't seen or read anything about that series."

"That's fine," Stephany said. "If you just set up some toys in the basement for a bit of BDSM fun, that'd be good enough for me."

"BDSM?" Jeff thought out loud. "I can do that. Give me... let's say two, maybe three hours? Meanwhile, you can get dressed for the occasion while I make a quick trip, and then I'll set something up.

*****

"Well, look at you!" Jeff said, looking at Stephany. He had just finished his preparations in the basement and got dressed in a two-piece suit, as he vaguely remembered depictions of Mr. Grey in a suit.

Stephany was seated in the living room. She was dressed in a thin, red, see-through night robe. Underneath it, she wore red laced lingerie. She had applied a lot of makeup to make herself look even more attractive than her usual self. Even though half of her face was now covered with a black, laced masquerade mask, she looked absolutely gorgeous. She even took the time to polish her nails red and put on matching stiletto heels.

"Good evening, Mr. Grey," Stephany said nonchalantly. She reached out her hand in a rather posh way.

Jeff reached out, took Stephany's hand, bowed forward, and kissed it, before standing back up straight and tugging Stephany's hand to pull her out of her seat.

"Good evening, miss..." Jeff said inquiringly.

"Palmer. Stephany Palmer," Stephany replied.

Right, I'm the only one who's supposed to be role-playing a different person, Jeff thought. He placed his left hand on the back of Stephany's neck, brought his face closer to it, closed his eyes, and got a whiff of her perfume before planting a kiss there.

Stephany was impressed with Jeff's directness. It was not his usual self to act this way. For not knowing much about his role-play character, he made a very good impression on her with his newfound attitude.

"Say, do you fancy a drink?" Jeff asked.

"A drink? Hm. Like what?" Stephany asked, trailing her index finger down Jeff's chest.

"Why don't you come down to my wine cellar and take a pick?" Jeff asked.

"A wine cellar? Not the answer I was expecting," Stephany said, imitating a mild shock. "I was hoping you had a playroom down there, instead," she teased.

"Oh, but it is," Jeff replied, his face turned smug. "I just call it the wine cellar because you'll be 'whining' for release by the time I'm done with you."

"Clever play on words," Stephany admitted. "But I remain unconvinced. Let's see this cellar of yours, so I can be the judge of those claims."

"But of course," Jeff said with a malicious smile. He led the way, holding Stephany by her hand to guide her to the basement door. He opened it to reveal a very empty-looking basement. "Ladies first," Jeff said. "Watch your step."

Stephany was confused. How had Jeff spent hours down there if nothing had changed? She slowly descended the staircase and as she did, she slowly noticed the view she had of the basement became distorted. In truth, a small fake wall was made with a print of the original basement view from the top, giving the illusion of it being empty.

Jeff entered the basement as well, locked the door, and closely followed Stephany. Arriving at the bottom, Stephany glanced past the fake wall to get a look at the devices Jeff had placed in the basement.

"Wow, you really went above and beyond on this one," Stephany said, both amazed and mildly worried. "Should I be worried about our finances?"

"I made some calls," Jeff said matter-of-factly. "I pretended to be some big entrepreneur and talked them into giving me a 'free trial' of their equipment. It's astonishing how much you can get away with if you can fool people into thinking you can make them rich."

"Impressive," Stephany complimented. "So... what do you want to do first?" she teased, giving Jeff a sultry look.

"Let's start with a safe word," Jeff said as he walked behind the fake wall to grab something.

"Uhm, 'cotton candy'?" Stephany said questioningly.

"Works for me," Jeff said, reemerging from behind the fake wall. He was holding a ring gag. "Open wide," He said as he inserted the ring into Stephany's mouth, forcing it wide open. He then moved behind her to fasten the straps and ensure a tight fit. "What was your safe word again?" he asked smugly.

"Koh-uhn Kenny," Stephany said indistinctly.

"Good," Jeff said. "I suppose that means your fate is in my hands now." He walked over to a spot in the middle of the room where a sex swing had been built. "Undo your panties and bra and come over here. The robe and heels are up to you," he said with a commanding, stern voice.

Stephany excitedly obeyed, dropping her lingerie on the floor and following Jeff to the sex swing.

"Keep facing me as you step into these holes," Jeff said, pointing at the padded cuffs.

Stephany complied and Jeff tightened them securely. He then made her place her hands in another set of cuffs behind her. With the cuffs tightened, Jeff then used the swing's pulley system to hoist Stephany up. Arms first, then feet. When Jeff finished, Stephany was hanging weightlessly on her back. Her head was hanging upside down and she had to pull herself up to see Jeff rolling in a fucking machine.

"Now," Jeff said with suspense. "Where shall we make this one go? Mouth? Or..."

"Huussy!" Stephany exclaimed to her best extent.

"Oh," Jeff responded in a fake surprise. "You wanted it in your pussy? I guess we'll need to mount a second dildo on it then." He let out a sinister chuckle and continued, "Good thing I have some attachments right here." He walked back to what looked like a mechanic's tool trolley and opened it to reveal various attachments for the fucking machine.

Jeff pulled out a dual dildo attachment from the trolley and mounted it on the machine. He then slowly brought the machine in closer and adjust its height to line up with Stephany's suspended height off of the floor. Grabbing a bottle of lube, Jeff quickly and carelessly squirted some lube against his girlfriend's vagina and ass. Instead of spreading the lube around, Jeff instead decided to give Stephany's pussy a couple of gentle, but firm taps with the tip of his fingers.

Stephany exclaimed with indistinct noises. Jeff responded only with a chuckle as he moved on to apply light lubrication to the dildos on the fucking machine. Having finished up, he then pushed the tip of the dildos in place so that they were firmly pressed up against Stephany's ass and pussy.

"I might not experience taking your anal virginity personally, but for today that's fine," Jeff said and grabbed hold of the dial on the fucking machine. "Any last words before we turn this 'wine' cellar into a 'whine' cellar?"

"He hennel?" the now-insecure Stephany voiced.

"Gentle? You wish!" Jeff laughed and started turning up the dial of the machine, making it spring to life. "You wanted this fantasy, I suggest you try to enjoy it."

As the dildos started pushing their way into Stephany's vagina and ass, Jeff repeatedly switched from observing the action up close and often rubbing Stephany's clit for his own amusement, and idly standing about while observing Stephany's face and moans, occasionally teasing her verbally and either fondling or slapping her breasts in varying degrees of intensity without losing eye contact.

This went on for several minutes before Stephany finally caved in and her moans turned into whines. Begging for release, from the machines and the swing. It was then that Jeff dropped his pants along with his underwear, and went to stand in front of Stephany's face, his erect nearly touching her face.

"I hear whining, but no safe word," Jeff said. "You still remember what your safe word is, right?"

"Yes," she began. "It's-"

"Good," Jeff interrupted as he carelessly forced his dick into Stephany's open mouth. "Let's put that ring gag to use then. I want to enjoy myself too tonight."

With the fucking machine giving Stephany a continuous double penetration, and Jeff now also using Stephany's mouth, only focusing on his own pleasure, Stephany's eyes slowly rolled to the back of her head. Stephany had never before experienced a feeling like this and it visibly started to overwhelm her.

Within minutes, Stephany was nothing more than a drooling mess, still conscious, yet barely responsive. She completely surrendered to the situation she found herself in. Jeff, on the other hand, felt in complete control. And although he enjoyed the experience, he also felt it was best to slowly bring things to an end, before Stephany passed out from the various stimuli her body was experiencing.

Before doing so, however, Jeff wanted to make sure they both orgasmed at least once. And judging by Stephany's state and the accumulation of bodily fluids underneath her, Jeff concluded she had probably already orgasmed multiple times by then and decided to instead solely focus on his own climax.

With his cock sliding in and out of Stephany's mouth as her head was hanging upside down in the swing, Jeff could see how his thrusts caused a bulge in Stephany's throat. The sight gave of which, gave him the idea to place his hands around Stephany's throat, so that, in a way, he could jerk himself off as he fucked his lover's throat.

After quickly confirming that Stephany was still conscious and not mentioning the safe word, Jeff put his idea to the test and discovered it was just what he needed to arrive at his climax. A mere minute later, Jeff found himself tensing up, and thrusting himself in Stephany's mouth as deep as he could, while simultaneously using his hands to pull her head into him in what could practically be described as an airtight seal.

When Jeff finished cumming down Stephany's throat, he slowly pulled out and released his grip on Stephany's head. With her lips still forced apart by the ring gag, There was no stopping the mixture of cum and mucus from drooping out as Jeff's cock left her mouth.

"Ah, now THAT was a good fucking orgasm," Jeff said, satisfied. He knelt down to put himself at eye level with Stephany. "So how was that?" he asked. "Did you have a good time too?"

"Hnggg" Stephany moaned as her body spasmed into yet another orgasm.

"I'll take that as a yes," Jeff chuckled as he stood back up and turned the machine off. He grabbed some towels, tissues, and hand soap and placed all but one of the towels on top of the trolley. Jeff then returned to Stephany and undid the ring gag, tossing it toward the trolley. He gently wiped Stephany down and moved the fucking machine backward before carefully lowering Stephany down from the sex swing and undoing her cuffs.

Stephany could not stand on her own strength as her legs still trembled heavily from the experience, so Jeff carried her back upstairs in his arms, covered the length of the couch with a set of towels, and placed her on top of it to recover.

"I'll go clean up downstairs. but I'll be back soon," Jeff said, giving a kiss on Stephany's forehead.

Stephany reached out to Jeff, gently touching him. "I love you," she mumbled.

"I love you too, Jeff replied softly, watching Stephany's eyes close as she slowly dozed off. 
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