Sissy Fantasy Stories

87,403 results
Orientation
Length
Source
Infinite Scroll

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

Cyber Sissy Ch. 02

by missvicky53 on Sep 25, 2017
Fetish

I waited, watching the door as the sound of Megan's heels came closer and closer. I noticed a distinct stirring in my white lacy panties as the anticipation grew. I couldn't help it, I was about to live one of the fantasies I had spent so much time reading about on the net. Besides, since following the list of instructions Megan had left, I was in no positio...

Natalie on Sunday

by natalieukcd on Oct 19, 2020
Transgender & Crossdressers

Lewis had fucked me after i had ridden him to my orgasm. I was no longer horny but he had fucked me anyway and although i wasn't really Natalie in my head during that, I still enjoyed having him behind me, holding my hips and telling me to keep my head down or lift it up. I loved the feelings of his cock inside me and he told me what a sexy fuck i was. I bel...

Pizza Delivery

by Spango on Sep 24, 2019
Transgender & Crossdressers

I could not believe that I was actually going to do it. I had been fantasizing about it for months. I was not really sure where I got the idea, but I had been watching a lot of sissy hypnosis videos online over the past few months, hoping to help release my inner girly girl, and perhaps the idea came from a scene in one of those videos. Anyway, it does not m...

Sissy College Ch. 01

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy! I love your comments! Chapter 1: Mathematics Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Suddenly Sarah, A Different Tale

by grizzley123 on Sep 14, 2020
Fetish

Suddenly Sarah, A Different Tale ************************** This is an alternative Chapter 2 to the Suddenly Sarah story I wrote recently. It takes day number two with Sarah in a whole different direction. It likely helps to read the first story. The themes of this story are not for everyone, but for those that like submission I hope you enjoy. As always,...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...