Ouch. Cock still in mouth “uhhh... helping a brother out?”
 
 He slowly pulls out of your mouth. “Well, I don’t remember any of it, but uhhh... this doesn’t leave this room. Ok?”
 
 You nod vigorously. “Yes Sir”
 
 “No. Just Caleb. This is a little odd for me. And you can keep the boxers.”
 
 He cleans himself up with a tissue, pulls up his pants, and walks out.
 
 You sit there for about a minute, realizing what happened when the door opens up again. It was Caleb
 
 “Actually if you can leave my boxers in my office, that’d be much appreciated. Hate going commando.”
 
 You nod.
 
 “And uhhh... next time, I’ll buy dinner for you.” Caleb winks and shuts the door.
 
 “Shit dude. That worked out way better for you than I though. I just wanted a blowjob while I wedgied the shit out of you, but that fucker broke through the minute things were getting good.”
 
 Still in shock, you just sit there. When suddenly, you’re lifted up into a hanging wedgie. You look down and the boxers are around your ankles.
 
 “Let’s get back to wedgies nerd.”
 
 The wolf bounces you a bit as you squeal from the pain.
 
 “That’s more like it.”
 
 He lets you down, puts you in an underclothes shoulder wedgie, and lets you return the boxers to Caleb.
 
 The rest of the day went without incident. Except for the titty twisters, wet willies, and working in an atomic for the rest of the day.
 
 You finally arrive home, I do your chair wedgie from the car ride, and walk into the house. It’s 11:30 by the time you eat, take a shower, and lay down in your bed in just a pair of pink panties. What Zach (the wolf) left for you to wear.
 
 “Well nerd, you gave me a really fun day today. So I’m going to leave you with two last gifts.”
 
 He hands you two packs of tighty whities one Hanes and one FTL. Nice that he replaces your underwear supply.
 
 “T-thank you.”
 
 Your panties shoot up, causing you to stand on your tippy toes
 
 “Thank you Sir.”
 
 The undies lower. “Better. And for your second gift.”
 
 He lifts you into a hanging wedgie and hangs you in the closet. Unable to get down, you accept your fate of sleeping in a hanging wedgie for the night. As midnight struck, the panties ripped, causing you to fall. You don’t care at this point. You go to bed naked and fall fast asleep.
 
 The End?

It was the night of the American Independence Day. Everyone in town was out and about drinking. You decided to visit the cemetery. You always found the cemetery to be a place of solace.
 
 As the night grew dark, you ventured deeper into the cemetery. A relatively newer section. As you read the gravestones with your flashlight, you notice that the birth/death dates are relatively close together. You then notice that many of them end on the same date. July 6th, 1970.
 
 You decided to write some names and the date. Leaving the cemetery and doing research the next day.
 
 As you google the date and clicked news. The first thing that popped up was the city local events calendar, and found out that a memorial for a school bombing going on tomorrow, in memory of the 50 year anniversary.
 
 Now you were never a social person, so you decided to pay your respects by walking the cemetery tonight.
 
 When you got out of the shower, you realized that it was laundry day, and all of your undies were dirty except for one pair. A pair that you keep for real kinky nights. A pair of bright pink panties.
 
 Now typically boys don’t wear panties, but hey, you love the silky feeling of them, and you’re going to be alone, at night, in a cemetery. No one is going to see you in them.
 
 You decide to do a load of laundry at the laundry mat before your visit to the cemetery, so you stuff a small drawstring bag full of your tighty whities, undershirts, socks, a tide pod, and your half roll of quarters, and went on your merry way.
 
 As you made your way to the cemetery from the laundry mat, you feel a chilled wind. The weather was supposed to be unusually cold tonight, but you didn’t think it would be this cold. You regret not bringing a jacket.
 
 You make it to the cemetery. It’s still a bit light out, so you wander the section you were at before. It looked different. Almost Victorian park-like. There were benches on the perimeter of an open area with stone walkways and a magnificent fountain. There were some nice iron work style pole lamps to light up the area at night. They seem to be flicking on and off during these dusk hours.
 
 The open area was surrounded by low hills, gnarled trees, and gravestones. Lots of gravestones. All of them facing the fountain in every direction.
 
 How could you not stumble upon this earlier? It was well kept, in the back of the grounds, and was absolutely silent. Only the sound of nature, you, and the fountain. You sat on the bench, putting your bag of clean clothes between your legs, and took in a deep breath.
 
 You decided to meditate a bit. Taking in all the smells and sounds of the area. You opened your eyes at the sound of an electronic beep. It was the sound of your watch. It was midnight.

Your heart sinks. Your boyfriend had just dropped a pair of your most personal belongings on you while you are laying down with his arm across your chest.
 You try to get up, but he is holding you down and has his legs wrapped around yours, stopping you from kicking.
 “What’s the matter? Don’t want me to know you like to wear panties?”
 That word. Hearing him say it just makes you freeze. Your cock gets a little hard at the sound of it too.
 “Op. I see that kind of excites you.” You can hear the smirk on his face from that statement.
 “Um... yes. Now can you please let me go?” You say, trying to escape from this nightmare.
 “On one condition.”
 “Sure. Fine.” You say hastily.
 “You are going to have to put those panties on in front of me and show me your kink stash. Then show me how much of a sissy boy you are.”
 Oh my god! Did he really just say that? I mean, being naked in front of him is no problem, you’ve fucked each other on several occasions. But to wear your pink, “Sissy Boy” panties in front of him, you thought you died and gone to Hell. But your dick says otherwise.
 “Is that a deal?” He says, still holding you tight.
 “Yes.” You squeak out. He lets you go and you jump up off the couch. Nervously, you slide your pants off, showing off your tighty whities with your name sewn in on the back and “Tuesday” sewn on the front.
 “Come on nerd. Drop those undies.” He says laughing a bit. You couldn’t help but get memories from that awful day in July. Sounded something like what Sir- you mean Zach the wolf, would say.
 You drop your briefs, and your cock was at full mast. Somehow this was turning you on. Caleb smiles.
 “Looks like someone likes being told what to do. Noted.”
 You slip on the panties and do a little spin. Showing off how the lacy waistband and leg holes. You do a little, awkward butt wiggle, hoping that will ease some tension.
 “Mmmmmm MMMMMMMM! Shake that tushie sweetie.”
 That comment causes you to blush, but more aroused. “How about you take me on the couch right now?”
 “Tempting, but first you’ll show me all of your other kinky shit. I want to know what I’ve been missing out on. You’re going to cum so much tonight.” Caleb says getting up from the couch. She walks up to you, wraps both hands around your waist. He gives you a deep, long, passionate kiss. One hand makes it way down and squeezes your left ass cheek during the kiss, the other finds it way to your bulge.
 “I want to fulfill your deepest desires sweetie. Even if that means treating you like a sissy. Now show me where you keep your panties.”
 That word again. It sends a wave of erotic pleasure over your body. Or it may be him rubbing your bulge. Maybe both.
You make your way to the bedroom, his hand still on your ass as you lead him to the dresser.

You open the top left drawer and reveal a drawer full of condoms, lube, a few butt plugs (one Bluetooth, one wired, and some regular), and a few dildos of various sizes and colors.
 “I’ve seen this one before. Show me the REAL drawer with all of you kinky stuff.”
 You sigh as you know he’s right. You go to your closet to reveal a small part of your closet with some soft dog toys, a purple pup hood on a foam head, a leather harness, a maid’s outfit purple and pink panties of various designs, knee pads, purple puppy paw gloves with padded knuckles, a flogger, and a paddle with the words “Attitude Adjuster” burned into them. Caleb looks at you and smiles. He gives you a big hug from behind, and scratches behind your ear. A sensation you desperately needed to calm you down.
 “Who’s a good boy?” He says in a voice one would ask a dog.
 “I am!” You reply cheerfully, happy that he accepts your kinks.
 “That’s right. Now let’s get you pupped out and give you a treat!” He says in now a more serious and sensual tone.
 You put the hood and collar with “Charlie” written on the tag on and a squeaky toy. Still in only your panties, you hop on the bed on all fours like a puppy, chewing your toy and having fun. It’s been awhile since you did this. But it feels so nice. Bending down, and attacking they toy, you feel something long get pressed between your cheeks and against your hole. You feel hands on your hips, fingers on your waistband, and thumbs in your leg holes.
 “Time for puppy to get a bone tonight.” Caleb says in a gruff tone. You love it when he does that. It makes him appear more dominate and aggressive.
 He pull down your panties just enough to expose your hole. He starts probing your hole with his fingers. They’re slick with lube that he generously applies. You prepare yourself for the main event, you relax your hole like you’ve done many times in the past, but then you hear something unexpected.
 “Keep chewing on that toy pup. It’s not time yet.” Confused, you listen and quickly get back into pup space. That’s when you felt stretching in your hole. You knew what it was.
 Caleb starts off slowly, causing you to squeak the toy in rhythm with his thrusts. Then he goes faster, and faster, causing you to drop the toy and howl and bark. Then he slows down again. Causing you to pant. You get back to your toy and again, squeak the toy in rhythm to the pounding of your hole.
 This goes on for another 3 minutes until he keeps up the fast pace. He’s grunting, your howling, it’s just a madhouse. Your prostate is sending wave after wave of ecstasy as he hits the same spot. Your dick is on the edge of creaming your panties, and then releases his load into your ass. But he keeps going. Not slowing down. You still haven’t came yet. Still on the edge. Just a little bit longer. Another load in you. It feels so warm and nice. Having your hole filled with your boyfriend’s seed as he slows down and lays on top of you, dick still in your ass, as he kisses your back and shoulders. Sending chills down your spine.
 “How was that?” He asks, scratching your head. God that feels amazing.
 “That was great, but I didn’t get off.” You say a little disappointed.
 “Really? Flip over. Puppy is going to give me a bone for once.” Your eyes widen. You’ve never topped him before, and now he’s going to let top him... as a pup... right now? This had to be a dream. You follow his orders and lay on your back.
 “Close your eyes pup. No peaking. Or else you won’t get off at all tonight.”

Halloween. Your favorite holiday. Typically, you’d spend almost every evening in the cemetery to get your spooky fix, but after what happened in July, you’d rather spend it home with your new boyfriend. After you blew him at work while getting wedgied in his boxers, things oddly had gotten better between you two. Despite having to stop your sexual escapades in the office, you two still had lots of fun in the bedroom outside of work.
 The first time you went over to his house to fuck, you decided to keep it vanilla and wear some tighty whities. Didn’t want to freak him out. Turns out, he’s a top, and will bring down the paddle if you were being too naughty, using your undies for leverage as he yanked them up your ass. You don’t know why, but you always like it when he gave you a wedgie while being spanked, despite all four cheeks being red from impact or crying. But he’d always hug you and kiss you to make you feel better.
 Caleb was the best boyfriend. And tonight, you decided to make your love for panties known.
 He came over to your apartment, thinking it was going to be like any other night. Dinner, Netflix, and fucking so hard your ass gets spanked from his pelvis.
 You were so nervous. You had no idea how to bring it up, or if he would think you were too weird. It’s almost like coming out all over again.
 As the movie ended, you were laying in top of the man, almost about to sleep. Damn he was comfortable. When you hear in a low voice, “Hey Carlos, I’ve been meaning to return these to you after I did your laundry a few weeks ago. They must have gotten mixed up with my stuff in the wash.
 He then reaches into his pocket and drops on your face a pair of bright pink panties with the words “sissy” and “Carlos” written on the waistband in metallic purple sharpie. Your heart drops. You thought you lost those. And HE found them. They have your fucking name on them.
 “So sissy boy, huh?” You can hear the smile in that statement. “You want to tell me something?” Halloween. Your favorite holiday. Typically, you’d spend almost every evening in the cemetery to get your spooky fix, but after what happened in July, you’d rather spend it home with your new boyfriend. After you blew him at work while getting wedgied in his boxers, things oddly had gotten better between you two. Despite having to stop your sexual escapades in the office, you two still had lots of fun in the bedroom outside of work.
 The first time you went over to his house to fuck, you decided to keep it vanilla and wear some tighty whities. Didn’t want to freak him out. Turns out, he’s a top, and will bring down the paddle if you were being too naughty, using your undies for leverage as he yanked them up your ass. You don’t know why, but you always like it when he gave you a wedgie while being spanked, despite all four cheeks being red from impact or crying. But he’d always hug you and kiss you to make you feel better.
 Caleb was the best boyfriend. And tonight, you decided to make your love for panties known.
 He came over to your apartment, thinking it was going to be like any other night. Dinner, Netflix, and fucking so hard your ass gets spanked from his pelvis.
 You were so nervous. You had no idea how to bring it up, or if he would think you were too weird. It’s almost like coming out all over again.
 As the movie ended, you were laying in top of the man, almost about to sleep. Damn he was comfortable. When you hear in a low voice, “Hey Carlos, I’ve been meaning to return these to you after I did your laundry a few weeks ago. They must have gotten mixed up with my stuff in the wash.
 He then reaches into his pocket and drops on your face a pair of bright pink panties with the words “sissy” and “Carlos” written on the waistband in metallic purple sharpie. Your heart drops. You thought you lost those. And HE found them. They have your fucking name on them.
 “So sissy boy, huh?” You can hear the smile in that statement. “You want to tell me something?”