Sissy Stories Stories

63,614 results
Orientation
Length
Source
Infinite Scroll

Cuckold Striptease Game

by Iftheshoefits on Sep 12, 2017
Fetish

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once ove...

Behavior Modification Institute Ch. 13: Final

by NancyPan on Sep 25, 2017
Fetish

Thanks to all of you who encouraged me to continue writing this story. Stay tuned for new stories. Please vote! All respectful feedback appreciated. ***** "Wake up, Nancy. Rise and shine. Time to get up, sissy." I hadn't heard the key turn in the door lock, and I hadn't heard Ms. Jensen enter my room. I sat bolt upright, then remembered that I was wearin...

First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

Sex Fifth Avenue

by skywayscribe on Sep 14, 2017
Erotic Couplings

Every day thousands of people walk through skyways above the streets of Minneapolis to stay out of the weather. Business people on their way in their busy lives traipse through high-end stores like Saks Fifth Avenue. Turns out the skyways of Minneapolis are great places to get it on. I'm Sissy and I work downtown. It's always an adventure. My boyfriend, Chu...

Submitting to Dominance Ch. 02

by _pdy_ on Sep 28, 2020
Transgender & Crossdressers

This is chapter 2 in the Submitting to Dominance series where our heroine Perry has some alone time with the man who will take her for himself. I welcome all comments, criticisms, suggestions, and feedback, but in general I just write these stories for fun so please take that into consideration. Thanks and I hope you enjoy! --- The drive to Perry's was ex...

Sarah Was Caught Masturbating

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

After collage, my girlfriend's best friend and I found ourselves working in the same town and so we decided to share an apartment. Her boyfriend had another year to go in college and my girlfriend worked in a different city. I loved living with her; we became the best of friends; just friends but very close. We cooked together every evening and watched TV....

Jackie Pt. 04: Alternative Ending

by Purple_Raihne on Sep 16, 2017
Transsexuals & Crossdressers

(This is a short one-off rewriting of Literotica Author Scribler's ending to his/her four part story Jackie, which in my opinion was horrifyingly mean-spirited, and completely destroyed for me the respect I had for him/her for writing Oasis In The Desert. In Part 4 of Jackie the author ended the story in a repugnant mean-spirited fashion that completely unde...

Mum & Sister Dress Him Up

by Quietoldie on Sep 14, 2017
Transsexuals & Crossdressers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things. "I just don't want to l...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...