Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

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...

Window Shopping Ch. 03

by kinki on Sep 4, 2017
Exhibitionist & Voyeur

I struggled awake. I felt so drained, it was a long day. I had drifted off with all the lights on and it was too bright when I tried to open my eyes. I managed to stumble out of the bed. By now it had cooled off and I felt a shiver and grabbed the blanket to wrap around myself. I reached to turn off the overhead lights near the window. Then I heard a knock a...

Jeri Ryan Best Sex Ever

by wwekiller on Sep 12, 2017
Celebrities & Fan Fiction

Jeri loved talking to her fans from her Star Trek days getting wonderful e-mails from them. Sometimes she would meet up with her loyal fans and would do certain things to thank them for their support. The odd striptease blowjob and tit wank would really be a good present for a Trekie and made Jeri feel very happy. There was one guy however who Jeri's heart f...