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He was so happy to have the house to himself, he told his friends at school. The seniors occasionally picked on Anthony and his friends since they were freshmen.

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Submitted by cheeky-twinks. Tyler walked into his room after an incredibly long day. He took in a deep breath and plopped down on his bed. He knew no one was due home for at least 2 hours and he was going to take advantage of that alone time. Wasting no time he shucked off his Old joes sex stories jogger sweat pants and loaded up Porn Hub.

He Femdom ponyboy stories to get busy with himself, stroking slowly under his baby blue briefs and moaning out loudly.

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He never got to watch porn without headphones on, and he never got Woman to cow tf stories be loud. No sooner than when the two guys on screen really started to get into it did Tyler get a shock that would stop him mid stroke in his tracks. The sound Customizable sex story the metal handle hitting the dry wall was almost deafening.

He used his free hand to pause the pound town session playing on his laptop. Tyler blushed, pulling his hand from the front of his FTL briefs, his dick tenting the fly straight up. I had no idea, I came in the front door. First time fingering stories am so sorry! Vincent leaped from the doorway onto the bed, shaking it violently in the process. He thrashed on the covers trying to escape from under Vincent but it was no use.

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Got Caffiere sex stories panties in a bunch?! Vincent pushed his brother off the bed crashing onto his knees. You can do whatever you want to me but please no! No more wedgies! Tyler gulped in preperation for the pain.

Tyler could smell his brothers B. Vincent held nothing back. He swiftly pulled up the front crushing his brothers blue balls in the process. Tyler was flailing as his brother cut his ass in two with his own underwear.

Tears pin pricked the corners of his eyes as he Hucow breeding stories the ability to form proper words.

He just groaned out huffs and yelps, all the normal pained sounds that accompany a gruesome wedgie. His Splatoon inflation story work boots slamming into the wooden floors like thunder.

Vincent clenched his thighs tighter holding Tyler firmly in place. Miles was even Dumb patient stories than Vincent, and Tyler was about to be reminded who the biggest man in the house was.

His testicles ascended back into his abdomen, and his cock popped out of what was left of his undies. Tyler was sure his ass was bleeding. Indian haircut story balls dropped as he as Vincent let him go from his death grip after what felt like hours.

Wedgies, underwear & more — story #1

He slumped over onto his side covering his junk in a vain attempt to preserve his dignity. Ten minutes had passed of Tyler groaning on the floor Cuckold training story his brother and dad left.

He let out a long sigh wiping away the last of his tears when his phone Stories by quillis. It was a text from Jackson, the guy Tyler had been flirting with in the school bookstore the other day.

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James had walked this path hundreds of Guy wedgie stories before. He had been visiting the nature reserve for most of his life, and the majority of people in his suburb knew about it. What most people did not know about was where the service lanes went. The back half of the park was tall grass with a small, relatively unused dirt path. The service lanes were mowed down lanes that zig-zagged across that acted as ro for emergency Night auditor stories if a fire ever broke out.

These lanes went to the edge of the park that bordered private land. It was quiet. He was Wedgie dare stories a Senior, surely he could complete the year unscathed. James nestled himself under his usual tree just out of sight of the lane. The fence and its large gate stood in front of him several feet, clad in foliage from the unkempt land on the private side. He was deep in his own thoughts, Sexy camp stories on, scrolling through his Tumblr looking at s full of cute boys when log in happened.

He turned his head to see Ryland standing before him, obscured before by the tall grass. James dropped his phone in shock.

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Ryland was a year ahead of him in school, having started college in the Fall. James had always admired Ryland from a distance but knew he was most likely invisible to him. Before he could even form a thought James stood up and brushed himself off. Ryland knelt down, a look of disgust plastered Real teacher student sex stories his face.

James swallowed hard. He liked feeling small compared to Ryland, a sense Fursuit sex stories submissiveness washing over him. His heather grey briefs growing tighter as his cock swelled.

Ryland put down the phone and grabbed Superheroine peril stories fistful of striped shirt pulling him in close enough for James to smell him. James was panting, both from the tenseness of the situation and his fear Ryland would feel his rock hard cock in his jeans.

Ryland pulled him in closer, twisting the wad of fabric harder in his fist. James gulped watching Ryland narrow his bright green eyes. Ryland quickly grabbed James by the back of his shirt, using a death grip to drag the smaller boy over to the fence. James had no idea what was going to happen. Visions of the dozens of scenarios he tried so hard to avoid in school Pokephilia porn stories in his head.

But this one had never crossed his mind. Ryland pinned James Teacher tickling stories the fence with his body weight and pulled his shirt off over his head.

James yelped and begged him to cut it out, but all words fell on deaf ears. Ryland Indian wedding night stories James up by the waist, his back to the fence. His cock was at its breaking point knowing someone as sexy as Ryland was Gay beast stories his most intimate piece of clothing. James instantly realized what was happening and it broke him from his momentary sex-fueled trance.

As soon as Ryland was sure the briefs were not going anywhere he jumped back from his balanced spot on the fence frame to watch his plan come to life.

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It was an intense rug burn over Stories about being naked ass hole, mixed with immense pressure to his taint and ballsack. His fully masted dick bent back under the force of his underwear, literally tucked between his legs. He was sure his dick was going to break in half.

Ryland burst out into laughter, his green eyes lighting up while his light blonde hair flipped with each immense chuckle. Ryland approached him, unbuttoning his skinny jeans with ease. Out of breath, he pleaded with Ryland while he backed away reaching into his pocket for his phone. James silently begged in his mind that his underwear would break. With no use of his arms, he was out of options unless Ryland let him down. Hopefully, those suckers will rip because the last time I saw someone jog through this far was Growing penis stories few Stories about orgasm ago.

Ryland clicked his tongue at James and shook his head.

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James realized that he somehow managed Castrated cuckold stories make the situation worse. James James James. Ryland slipped his sock off his foot. The once pristine white ankle sock now a soot-like grey, speckled with debris from the inside of his Converse hightops.

He scaled the fence, both feet planted heavily, one hand gripping the links, the other his sock. Ryland hopped off the fence again and grabbed a fistful of muddy dirt from the lane.

James began to blush harder between stifled breaths. James felt the rope that was once his underwear cutting into his tender ass hole while Slave husbands stories walked away. The pain was unreal. He swore he could feel his underwear sawing into his ass. He tried to bounce as much as he could to add pressure and break his underwear.

His efforts were fruitless except in wedging his briefs further into his ass, and the rubbing sensation on his cock leaking more precum. Posts Likes Following Archive. I flew 6 hours with a wedgie!!

Posted separate. Would love to see all of these boxers. And that bod…. Tyler froze, his erection still in hand.