Sissy Cocksucker Stories

13,753 results
Orientation
Length
Source
Infinite Scroll

Black Cop's Stress Relief

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

"We think you're doing a hell of a job, Corporal," the bronze-skinned police lieutenant explained. "But at this time we're going in a different direction." "Alright. Thanks for letting me know, Lew," replied Christopher Patterson with a fake smile. "Is the candidate internal or external?" "External," the supervisor revealed. "Alright. I'm kinda tired," Cp...

Kasey's Confession Ch. 08

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I woke up the next morning feeling incredibly sore all over. I was lying on the couch in Mr. Smith's living room, covered up with a blanket, with only vague memories of what had happened after Mr. Smith finished fucking me. I knew Pedro and Jake had taken turns with me as I had flashes of memory, almost like photographs, of them putting me in different posit...

Who's The Sissy Now?

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going through something of an identity crisis surrounding my body a...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...

Happy Marriage Ch. 02

by yesplease8 on Sep 25, 2017
Loving Wives

Well, our marriage just keeps getting better. My wife and I love that I'm submissive and that I was bi-curious. I say I was bi-curious, because my wife set me up to realize I am truly bisexual. After begging her to use me like a sissy slut with a strap on, she not only treated me like a slut with her strap on, she happily watched me with another man. She se...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

On Line and Linda

by vinceh23 on Sep 16, 2017
Romance

Linda and I had met through one of those ubiquitous on line dating sites. When I saw her photo it grabbed my attention. We all have certain characteristics in face shape, eyes, kips, those things we can't necessarily define but when we see them we know immediately that we like that face. And she was tall, 5'9", and though not slender she was not overweight....

A Roleplay Gone Awry

by ronald81 on Sep 15, 2017
BDSM

All people within this story are over the age of 18. ***** For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember. It all started when I was playing a roleplaying game featuring a text based game that was su...

Becoming CD Mistress Raven's Slut Ch. 02

by Vodka_Jim on Dec 10, 2018
Transgender & Crossdressers

Author's Note: I took some inspiration for this next chapter from some of the comments, both public and private, that I had to the first chapter. In doing so, I've written about things (e.g. forced cross-dressing) that I've never personally experienced. Most of my writing is based on things that I've experienced and that I think I can relate. So, if I've mis...