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First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Bicurious Fantasies

by RoundAss30 on Apr 22, 2025

It was 3 PM, on a rainy Friday afternoon, and I was home alone, my room mates were out for the weekend. The door bell rang, it was the last of the packages I ordered over the last days. I felt excited and had planned a horny night. Although I was a quite manly male, I sometimes had these very submissive bottom gay fantasies. A left-over from my college years...

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Delta City: Rise of Chameleon

by Miles63 on Sep 26, 2017
Transsexuals & Crossdressers

Authors Note: Hey everyone, I thought I would try a comic book/superhero type story with my usual type of sexy fun in it as I am a bit of a geek and I love graphic novels. I'm not sure if this will continue or if it's a one off. But if enough requests come in to add to it, maybe I will add to it but no promises. It's a bit long but I love it and I hope you...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

2020 - WIC

by Rekki on May 10, 2020
Miscellaneous

WIC, short for „Weekly Image Captions“, is a project I started this year to post an image caption each week. The characters, scenes and kinks are often different from piece to piece but there are some reoccurring themes like Timestop and Mind-Control, since these are my own favorite kinks. Since March, it‘s possible to choose the character for an upcoming we...

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AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

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...