Boy Wedgie Stories

105,330 results
Orientation
Length
Source
Infinite Scroll

A Night at the Gym - F/M Mixed

by Notbob8448 on Jul 1, 2019
Fetish

She was introduced as Margot at a party of a mutual friend. She was very attractive and I was thrilled to be introduced to her at first, but her conversation starter was, "You look kind of wimpy." I'm not a big muscular guy, but I'm relatively fit and I get occasional compliments on how I look. I'm pretty confident in my physical abilities. I played footbal...

Sally's First

by sally_spandex on Sep 16, 2017
Transsexuals & Crossdressers

My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Altho I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's and catching my cum in my open mouth, and craving the load of ano...

Book Store Slut

by fuckup77 on Aug 19, 2017
Exhibitionist & Voyeur

Henry always was fairly shy. Always scared to reveal his true self to the world. Terrified to find out exactly what the rest of the world might think of him. 6' tall, combed back shaggy hair, and a relatively average body. Never overly popular with the ladies, but still some experience. Henry worked at a local bookstore. One of the most exciting moments of...

My Life as a Crossdresser Ch. 02

by asian_CD on Sep 16, 2017
Transsexuals & Crossdressers

The next morning I woke up with a little extra jump in my step. I quickly went through my morning routine, and threw on a random pair of shorts and t shirt to hide my thong while I went downstairs to grab a quick breakfast. Looking around the house, I made sure that nobody was home before I went back to my room to start making my profile for the swingers' si...

Bliss

by IreneXXX on Sep 14, 2017
Erotic Couplings

His meeting took longer than expected and he was late picking me up. Nonetheless I was glad to see him after his busy week. He looked really tired. I was worried that he'd be exhausted since he'd just had a long day at work. But he insisted he was fine and despite a headache, wanted to dance, too. We were supposed to meet 2 girlfriends at Brix, so he decided...

Re-submit

by Mine0214 on Sep 16, 2017
BDSM

So there she was lying naked, exhausted, feeling the coolness of the bed clothes beneath her. She was in an intimate space all her own; completely satisfied, completely loved, completely owned. The memories of how she got there played out in her mind as she gradually drifted off. ------------------------------ She was wearing her favorite pair of panties,...

Not My Fault

by Myxy on Sep 19, 2017
Transsexuals & Crossdressers

Look, it wasn't my fault. I was over at my sister Sally's house; she was having a party that night, and I, as usual, was there early to help her with her outfit. I know that makes me sound kind of girly, but whatever, it just shows that she values my opinions! Anyways, I had come over straight from the gym (I'm not what you'd call bulky, but I do keep in sh...

Alex's Feminization

by Bcriswell on Sep 13, 2017
Transsexuals & Crossdressers

Alex hated his body. At 18, he expected to have gained some muscle or some body hair. Instead, he was hairless everywhere but his head and was still slight of frame. But there was one part of his body he hated more than anything. His butt. He had been cursed with a butt that was in a word, fat. His rump was round and looked like it would have been more at ho...

The Holiday Discovery Ch. 05

by tach14 on Mar 27, 2019
Fetish

This story continues after Anna finishes her drive home from the park. Anna sighs deeply as she pulls into her driveway calming down after the events that took place earlier this morning. She gets out of her car and goes inside to change. Taking her dirty jeans and thong off, she pulls on a bikini style pair of pale green panties that are a little small ca...

The Joys of Air Travel

by Voboy on Sep 13, 2017
Loving Wives

Late in the boarding process of Flight 5608 from Phoenix to Chicago, and my husband and I were getting tense. "Come on..." he whispered under his breath, jammed into the space beside the window on my left; I, so much smaller than him, had the middle. The aisle seat on my right was still open, and with each passing boarder we crossed our fingers more tightly...