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Destroying his Tighty Whities 😈

You’re at your friend’s house swimming in their pool. You are there with 4 of your other friends just splashing around, having a good time. You change over to a new game, Marco Polo, and the guys decide that you should go first. You close your eyes and loudly count to 10. You’re walking around the pool shouting “Marco!” to no response. You don’t want to cheat so you keep your eyes closed and keep calling for them to figure out what’s happening. After some time, you open your eyes, to see all 4 men standing around you on every side.

One guy goes underwater to pull your swimsuit down. As you’re shocked and try to pull them back up, one man is on each of your sides and grabs your underwear: a pair of grey Nike boxer briefs. They start with the waistband and lift you up from all 4 sides at once. You groan and shriek, wondering what caused this to occur. The guys are laughing as they continue to bounce you, watching as the wet, dark grey, fabric moves from your waistband and up to your chest on all sides, your pale ass beginning to appear. They begin to switch places so they can all have a turn giving you a wedgie from all sides. They begin to grab fabric and bunch it up to make it move faster up your ass, your cock and balls being in pain from the seams being wet and rubbing into you.

Can you imagine your bully seeing you in the hallway? Just the two of you in the room? Imagine that he grabs your hair, yanks you back towards him, then pushes you into the wall. He chuckles, as you and him both know that he’s in charge as you grunt and groan with your hands against the wall and your back turned towards him as he stands behind you.

Imagine that the next thing you feel is his large hands on your hips, as he mentions that he’s about to have his way with you. Imagine his hands pulling your shirt up from being tucked into your pants, and he digs his right hand into your pants to grab a fistful of your nerdy tighty whities. He chuckles as he knows that you know what’s about to happen. He whispers in your ear and you can’t help but know what he says before he says it, “it’s wedgie time.”

He yanks you up with his right arm as he lifts the waistband of your underwear out of your pants. You can feel your legs tighten, and every spot of your body coils up as your ass is in pain. He switches to putting both of his hands on your undies and lifts with all of his strength, lifting you up into the air, bouncing you, and holding you in the air by nothing but your tighty whities. Imagine that you hear him grunt and chuckle, reminding why he’s in charge, and why you deserve this. Your choice in underwear reminds you why you’re such a loser. He bounces you one more time as your legholes peek out of your pants and he descends you back down to the ground.

He ends his torment with you by pulling your pants down and smacking your ass. Right before he walks away, he whispers in your ear, “anytime you want a wedgie, just keep wearing these fucking tighty whities, bitch.” He punches you in the balls as you recoil in pain, your ass being in pain from your wedgie, and your balls being squished from his fist, and from the front of your briefs that have been pressed into your stomach from the wedgie. He slams you into the ground and walks away, leaving you to figure out what to do next with your miserable life.

Rough submission. Locked up getting chocked out while holding yourself up. The extra salt in the wound is the trunk wedgie Thong reveal.

Devastating Thong wedgie.

Scrappy recieving a vicious Melvin with the humiliating Jock reveal. Embarrassing.

Danny had just gotten home from a long day at work. He after showering decided to hop on the unholy app to find a guy to help him get his rocks off. He got a “dtf?”message from a blank profile. They exchanged pictures of everything below the head. They decided to hookup at Danny’s place. Danny hoped that by having some rebound sex he could get over Andy his ex boyfriend.

He told this mystery guy to just walk in and come to bedroom down the hall and to the right.

As Danny waited anxiously he heard a knock and then the door open. Danny lay there on his bed on his stomach in nothing but his tightie wighties. The doorknob to his bedroom opened. Danny glanced backward to see the mans face. Lo and behold it was Andy. Danny quickly looked back at his headboard questioning his every decision.

“I can leave it you want…” Andy says.

Danny thought for a second. “I mean… it would just be sex right? You haven’t changed your mind?”

“No… you still cheated… so it’s just sex.” Andy replied.

It was true. Danny had run in with a run in with Long Island iced tea and hot Italian man. He was still ashamed but understood why Andy didn’t want to stay together.

“Okay is there something you want to do?” Danny asked. Still facing the headboard embarrassed to look at his ex.

Andy thought for a moment. “We can do anything?” He said.

Danny could hear the smirk forming but felt guilty so he nodded.

Andy walked closer to the bed and laid down next to him. Danny could feel Andy hand sliding down his back slipping it under his white briefs into bare his ass. Danny could feel his cock starting to harden. He slipped a moan from his mouth.

“You like that?” Andy asked

Danny moaned in reply. Suddenly. Danny’s ass crack was met with the slight burning sensation of his tighty whities being logged up his ass! He let out small yelp in between moans.

“What the fuck are you doing?” Danny said. Andy still having a grip on his underwear.

“What? You said we could do anything and this is what I want to do! Remember the night before you slept with Italian man whore? Well you forgot to delete your internet history. I went to search something and saw auto fill for wedgie porn. I saw this as the perfect opportunity for me to get a little revenge.” Danny’s underwear was halfway up his back but the time Andy finished his monologue.

All Danny could think of was how he deserved this wedgie punishment. The only thing he couldn’t figure out is if he liked it or not. He was still hard and it was doing something for his dick.

“Please stop I’m s-“ he was cut off by his waistband being strapped over his head. He moaned he could fill himself getting ready to cum.

“You don’t really want me to stop do you wedgie bitch?” Andy said as he moved to foot of the bed where Danny’s ass was sticking straight up from the wedgie. Andy slid Danny closer to the edge of the bed. Danny still trapped by his underwear.

“What now?” Danny said accepting that he was in fact Andy’s wedgie bitch. At least for the time being. Danny wanted it last. After all he was still in love with Andy. Maybe this could win him back Danny thought for a split second as he felt a rip. Andy was spreading his ex’s ass cheeks open with his white briefs. Exposing Danny’s tight asshole. Before this Danny had always been a top. Why was okay with happening he thought? He felt Andy’s throbbing penis start to tease his crack. After spanking him a couple times. Andy entered Danny’s bussy they both moaned calling out each others names. Andy pulled the front of Danny’s briefs as he thrusted. Danny felt himself getting closer and closer to climax. With one final tug on the front of his tightie whities. He finished. The sounds of Danny’s completion was just enough for Andy to finish still inside his ex boyfriend’s hole they both collapsed on the bed Andy still on top of Danny.

“How was that my wedgie boyfriend?” Andy whispered in Danny’s ear.

“Does that mean we’re back together?” Danny said with his underwear still over his head.

Andy rolled Danny’s wedgied body facing each other they kissed.

Friday's were a good day for me as they are most people. Why were they normally good for me? Well my Fridays always started at 5:30am I'd go to the gym, I'd go the gym, work a shorter shift at work, and then going out to the bar with friends to shamelessly hit oh hot older men who's wives didn't know they were at a gay bar. I'd pull one every once in a while. I give him the best orgasim of his life and then send him back to his wife in shame.

This Friday was different, though. I slept through my alarm and was late to work. I shot out of bed. Put on whatever clothes were on the floor and ran out the door. I got to work and saw a text from my mates that they all had to cancel at the last minute. I am a little relieved that I didn't need to rush after work to get ready for the evening. I figured I might as well go to the gym after work instead. So after work, that's exactly what I did. I'd never been to the gym on a Friday evening. I walk in past the cardio floor and make my way to the locker room. It was a ghost town no one in site except for one older gentleman seeming to be in his mid to late 50s. I paid him no mind as I got into my gym clothes and headed to the weights. I had a greeaat workout. I had been so in the zone that I didn't notice the same man from the locker room was working out near me. I thought it was a little strange considering the emptiness of the gym. I went back to the locker room, stripped down to my briefs, wrapped a towel around my waist, and headed to the steam room. A few minutes go by, and guess who decides to also take seem the man from before. He's got salt and pepper hair on his head chest and face maybe 6 foot at least. He looked like the kind of older man I'd pick up while out at the bars. Not completely ripped, wide body with a bit of a gut, and an ass the won't quit. He sat on the bench just below where I was sitting. His loosened his towel just a bit. I look down and see a bit of hairy ass crack pocking out. Just below it was the waistband of a pair of Goodfellow underwear. I wanted to see what else was underneath, but as my hand started to move toward his underwear. Before I really registered what was I was doing, I heard a deep "hoop" come from the man. I realized I had a handful of his briefs.

I let go, "I'm so sorry, mate. I don't know why I did that." He stopped me and turned chuckling a little and said, "I haven't been wedgied like that since I was in school." I smiled, released. Looked and noticed a small tent pitched in the front of briefs. "That turn you on?" I say smiling wider. "Well... uhh..." with a tone defense in his voice. I pulled my towel open to reveal the growing bulge in my underwear. He looked down and smiled. "Looks like you also enjoyed it. Dominating an older man turns you on?" He said. "It looks like it." I said.

He looks at me and touches my thigh. I look at him and ask "Does daddy need more cotton up is ass?"

"No! Stop!" Jason yelled, but it was all in vain. He was on his stomach as Bryan sat on top of him. Bryan pulled on Jason's red breifs "but these are so stretchy, why would I stop?" He replied "oh and look!" He grabbed Jason's foot and attached Jason's waistband to it. "The perfect spot to place these." He says as he repeats the action with Jason's other shoe. Now not only was he in an uncomfortable wedgie but his hairy ass was also on display. Bryan steps back and watches Jason squirms as Bryan appreciates his work. Jason's mind is rushing trying to figure out how he got here and if he should keep fighting it. He's had a secret crush on Bryan for a year now and likes the attention but if people found out he was an actual freak he'd never be able to recover. It started after he got a job working with Bryan on the night shift at a hotel. They've been working together for a year. He took one look at Jason and he was hooked. Just like his underwear was hooked to the back of his feet on his apartment floor.

He had invited Bryan over one weekend to watch a movie and play card games. Jason answered the door to see his fantasy man standing there. Bearish in stature, hairy arms, face, and hair up in a messy man bun. Jason's heart skipped a beat. They walked over to the couch where he had set up the coffee table with pizza, chips, and vodka crans. "Sorry do you drink? I have alternatives if you don't." He looked at Bryan as they sat on the couch. Bryan crossed his legs, "haha yeah I drink. I should warn you... vodka cranberry drinks lead to bad choices." He winks. Jason didnt know how to read that so he just laughed and adjusted his shirt. Jason was a little chubby, he was hairy in the pits, and privates, especially his butt.

"What are we playing first?" Bryan asks "I was thinking Phase 10." Jason replies. "I kick ass at this game!" Byran says with competitive nature. "You're on!" Jason says dealing the cards. The first several rounds are pretty uneventful until Jason says "whoever gets their cards out last in a round has to take a drink." Bryan smiles and agrees. The next few rounds get a little more intense each one having had several shots of vodka on top of the drinks they started with. Finally they both get to the 10th round. "Looser has to get punished winners choice." Bryan says with a smirk and a sexy drunk voice. Jason smiles and nods. The round gets intense as they make their way through the cards. Jason just needs one more card when Bryan places all his cards down and says "I want to give you a wedgie." He looks at Jason. Jason is mortified but trying to play the good sport and says okay.

They move to an open section of the living room. Bryan stands behind. Jason, trying to ignore the slight boner he has casually says, "I've never actually had a wedgie bef-HUH!" Before he can finish his sentence. Bryan starts pulling the back of Jason's underwear. Not knowing how to react or how long to let Bryan pull he just stands there and takes it. "Wait..." Bryan stops for a second and in a second jason is on his knees and then stomach. "I was bullied like this all through high school and you've never been wedgied? Well... I'm about to give you a crash course." He laughs but Jason finds it to be kinda sexy instead of scary.