Rubber Sissy Stories

28,680 results
Orientation
Length
Source
Infinite Scroll

Sissy Dreams Ch. 01

by SissyJane on Sep 13, 2017
Transsexuals & Crossdressers

I wake slowly, lazily, in a soft fog of deep relaxation. A slight shift of my body reminds me of the satin lingerie that swaths my body in sissidom. I wait for you. I feel the brush of something, cloth, no satin. Flittering over my skin like a drizzle of wax leaving me on fire. It moves like snake and slithers over me, making me shiver in a fever. It finds...

In Need of Counselling

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

I knew my wife, Becky was unhappy just before Christmas. We had been married for five years and she seemed dissatisfied with everything. We had been incredibly unlucky. I'd been made redundant, we seemed incapable of having children and I had lost interest in sex. I refused to accept that there was anything wrong with our relationship yet she insisted we saw...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Jacki's Journey into Sissyhood Pt. 02

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. ***** I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from unde...

The Hanky Code Pt. 17

by His_fag_wife on Sep 14, 2017
BDSM

Mistress paused, to let the enormity of her comments sink in. What would Archie her husband be doing now? Would he be stripping at this point or frantically checking on the websites he'd been on and erasing his history. He was caught and if he only knew how his life was going to change, he might not have looked at some of the more extreme sites he had. "Yo...

Stroke Slut: Goddess' Cuckold

by StrokeSlut on Oct 19, 2020
BDSM

"Well don't just stand there drooling on the doormat, come on in." The black hood had come off Stroke-Slut's head, the sudden burst of sunlight that hit his eyes was nothing compared to the radiant beauty that stood before him. Despite hours of jacking off to her on the internet, not the mention their previous sessions, he never seized to be amazed at the si...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

My New Neighbours Ch. 02

by csm1967 on Dec 19, 2018
Transgender & Crossdressers

Apologies for the time it has taken to write this second chapter. I went on an overseas holiday and when I returned had to move house. Still settling in so hopefully, this won't be too disjointed as a result. ***** I closed the front door behind me and leaned back against it, eyes closed. My mind was swirling with what I had just been through. It was witho...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Mistress Marisa's Estate Pt. 21

by keptsissy on Sep 15, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** As I enter your bedroom I see the box on your bedside table. THE box. My face flushes. You are at your makeup table, che...