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A brief game of truth or dare Other One time when I was 12 I slept over a friends house and we played truth or dare with dares only. My friends are the same age as me, and their names are sam and nick. First Sam dared me to strip into my undies, white briefs, for the rest of the night. We destroyed his undies at headheight. He had to go change them while me and sam laughed like hell. Nick got his venagence by daring me and sam to trade undies for the rest of the night.

Name: Gina
Age: 50
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Wedgie dare #1

Stories are fiction and intended for readers 18 and up. All characters are assumed to be legal, consenting adults. Images are reblogged exclusively from other Tumblr s. James had walked this path hundreds of times before. He had been visiting the nature reserve for most of his life, and the majority of people in his suburb knew about it.

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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 vehicles if a fire ever broke out.

These lanes went to the edge of the park that bordered private land. It was quiet. He was finally 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.

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He was deep in his own thoughts, headphones on, scrolling through his Tumblr looking at s full of cute boys when something happened. He turned his head to see Ryland dare before him, obscured before by the tall grass. James dropped his phone in shock. Ryland was a year ahead Wedgie 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 on his face. James swallowed story. He liked feeling small compared to Ryland, a sense of submissiveness washing over him.

His heather grey briefs growing tighter as his cock swelled. Ryland put down the phone and grabbed a 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.

Wasn't expecting that

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 flashed in his head.

But this one had never crossed his mind.

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Ryland pinned James against the fence with his body weight and pulled his shirt off over his story. James yelped and begged him to cut it out, but all words fell on deaf ears. Ryland lifted James up by the waist, his back to the fence. His cock was at its breaking point knowing someone as sexy as Ryland was touching 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 Wedgie anywhere he jumped back from his balanced spot on the fence frame to watch his plan come to life. It was an intense rug burn over his 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 dare.

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.

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Hopefully, those suckers will rip because the last time I saw someone jog through this far was a few weeks ago. Ryland clicked his tongue at James and shook his head. James realized that he somehow managed to make the situation worse. Ryland slipped his sock off his foot.

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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 Ryland walked away. The pain was unreal. He swore he could feel his underwear sawing into his ass.

Ouch - i never wedgied him again

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.

Superheroes in Underwear Just a gay guy who loves superheroes and underwear briefs tho, boxers do not interact main: timothykaplans. The OG WedgieAddict. Wedgies And More.

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Sans titre. Recently Liked. This is where James liked to go.

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Uhm hi there Ryland! James stammered for words, his cock now clearly visible through his dark grey skinny jeans. He was getting a wedgie. Ryland pulled James jeans to his ankles with a few easy tugs. He felt humiliated like. The older boy gingerly slipped his phone into his pocket and walked up to James.

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As Ryland walked away James burst without thinking. James James James. Ryland walked off down the lane only to stop and turn back for a moment to speak. He sighed and thought between faded breaths.