Sissy Training Stories

41,670 results
Orientation
Length
Source
Infinite Scroll

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...

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

Taken Too Far Pt. 02

by SwitchSissy on Mar 10, 2020
Transgender & Crossdressers

"Good girl" He smiled in approval. "Now, I noticed something earlier, when I was clicking that new, secure padlock onto your clitty" he reminded me, pulling me up so I was now sat on the bed, my arms bound behind my back with duct tape. "You've written something there, and on your thighs. And I think I can also see something on your belly button too, you lit...

Training Aide Ch. 02

by Angelscuck on Sep 16, 2017
BDSM

Mistress Elaine stoop up, causing me to roll off her lap onto the floor. I just lay there naked, sniffling like some little sissy, waiting for my next ordeal. My Mistress then said, "It's a good idea, at this time, to let your slave have a few minutes to recover. It also gives him time to let the realization set in, that he has been totally broken and is...

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...

Few of My Ultra-Perverted Fantasies

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

Hello, I am a white boi who's addicted to sissy porn and have a lot of wicked and perverted fantasies. In this list, I will enumerate some of them. I would ask the readers to name the one that they like the most in the comments section so I can write a story about it. Authors are more than welcome if they want to write about any of the themes mentioned here...

Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....

Sissy Sisters

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

This was the letter I wrote to an older Sissy in an attempt to convince Her to accept me as Her littler sister and use me. * Stop, You make me blush. I too luv wearing feminine luxurious things. I believe now I need to wear sensuous feminine things under the direction of some one else. Could that possibly be You. Please. You would treat me like a little...