Sissy Bikini Stories

40,840 results
Orientation
Length
Source
Infinite Scroll

Inaugural Crossdress Sexfight Ch. 04

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The league's first tag team match featuring another newbie. Participants Dani Davis (me): Record 1-3 Jamie Play: Record 1-0 vs Dani Delights: Record 1-1 Mandy Spencer: Record 0-0 After hearing about our club, I was approached by a new gurl, Mandy, who had the body to fit right into our league. She was a rookie, but was interested in a tag team match after...

The Sexy Cuckold Couple Pt. 11

by cuckcpl4play on Sep 19, 2017
Fetish

This is part 11 of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneducated or despi...

High Society Sissy

by beyondkink on Sep 11, 2017
Transsexuals & Crossdressers

I guess I can say I was one of the lucky ones. Fresh out of an ivy league school with a degree we were met with two different tales. "Sorry, you're over qualified," they said. Or we would hear, "We're looking for someone with more experience." An alum that I had befriend however was able to land me a waiter position in a posh New York country club that ca...

Mom's Big Black Hobby Ch. 07

by MiddleKoala on Jul 13, 2020
Transgender & Crossdressers

This story has with homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is fiction as are all characters. Any likeness a...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Bukakke Sissy/Angel

by hyperpress on Sep 14, 2017
Fetish

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how fem...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...