Sissy Fantasy Stories

87,403 results
Orientation
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Infinite Scroll

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

Neighbourhood Terror to Sissy Pt. 10

by Fibaro on Jun 10, 2019
Transgender & Crossdressers

Chapter 12 Mark had just about time to put his dildo down before the door to his room opened. His hand was still wrapped around the base, and well there was no real way he could ever hide anything of what had been going on. He was caught red-handed and could only really look at his girlfriend, or rather his ex-girlfriend in horror. After all, why else than...

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

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The Descent

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence....

Surprise

by cwsissy on Sep 13, 2017
Fetish

Yesterday my wife called on my cell phone and told me to get home because she needed me. Having an inkling that there might be some fun in it I rushed home. When I got there the bedroom door was closed and there was a note stuck to it telling me to have a shower and make sure I was shaved clean - face and pubes. I obeyed as fast as I could. Then I went into...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Sissy Whore Ch. 02

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I wrestled with my emotions for the rest of the afternoon, sitting on the sofa trying to distract myself from the mysterious web chat. I'd been at this a long time now and I was used to conversations that went nowhere. Most of the guys that contacted me followed up with a dick pic and were not really capable of continuing the fantasy beyond the scant descrip...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

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...