Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Groomed to Depravity Ch. 01

by ssamlee2000 on Apr 22, 2020
Transgender & Crossdressers

I kind of liked it. The feeling of black sheer stockings on my legs. I rubbed my legs together to enjoy the smooth, silky sensation. I looked in the mirror and take the sight in: a thin Korean boy, just about 5'6" in height, dressed like a cute skater girl. I was getting ready for the big college Halloween party. As a long-standing tradition, the college he...

Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

The Molly Virus Ch. 03

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

*Jeri... I still got a few looks as I came in from the cab and to my room. Word seemed to have spread a little about me and my transition. The few looks I got were more dumbfounded and not getting it instead of like hateful and I'm pretty sure there were eyes on my ass as I went up the stairs to my room. Jack's there listening to music on his headphones lo...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

More Domme Club: The Appointment

by NancyPan on Sep 26, 2017
Loving Wives

For this sequel to The Domme Club, I am switching the category from BDSM to Loving Wives. Seems that many of the stories in the BDSM category are more hard-core. And this story is about Loving Female Authority. As it is a sequel, the story is best read AFTER reading The Domme Club. Once again, all respectful feedback, as well as voting, is very much appr...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Cum at the Mall

by bottomhub on Jun 11, 2019
Transgender & Crossdressers

"Eat that pre-cum, sissy," -- I masturbated furiously in the passenger seat of her car. I was wearing panties under my jeans, and Mistress knew this; she found it amusing. So would some of the passers by if they only knew what was going on. I could barely keep up with the complications. "And don't waste any!" she continued, sternly slapping her right index...

Not What We Planned Ch. 02

by KinkyDirty on Jun 15, 2020
Loving Wives

I'll get around to telling how the last twenty minutes of the first story finished at some point, but it suffices to say, it was awkward. Abby and I drove home without speaking and went to bed without speaking. I didn't know how to feel. Was I mad? Maybe at the overall situation, but I suggested the night. I really couldn't be "mad" at Abby. She obviously ha...

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...