Sissy Training Stories

41,670 results
Orientation
Length
Source
Infinite Scroll

Sculpting Mei-Lien Ch. 07

by anon1940 on Sep 14, 2017
Erotic Couplings

At ten o'clock Saturday morning, my door bell rang, and I found a freshly scrubbed, ebullient Mei-Lien waiting to be let in. As soon as she was inside, she stepped in front of the hall mirror and, with an exultant smile on her face, unbuttoned her coat to reveal that, aside from the socks and sneakers on her feet, the only garment she wore was a leotard. Fur...

Rainy Morning

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to Southronstyle for editing this story. It was a rainy Monday morning, the last week of September. I was tired, very tired indeed because I had been away Friday and Saturday at a training camp with my son Martin's hockey team as an " hockey dad", assistant coach and driver of the rented travel bus. We had come home late that previous Saturday...

Maid for Summers

by MTL17 on Sep 25, 2017
Celebrities & Fan Fiction

Disclaimer: I do not own Buffy the Vampire Slayer and have no association with anyone involved in either shows. I do not make any money from the writing of this story. Author's note: This story takes place mostly in Season 3. ***** Upon hearing her alarm Faith's first instinct was to smash it, but her training forced her to reach over and calmly turn it o...

Playing It Cool

by redzinger on Sep 16, 2017
Romance

This is an entry for the 2014 Literotica Winter Holidays Contest. Contains: snow, high levels of drinking, weather-related peril, references to classic rugby matches, a pitched battle and perhaps some romance. Please vote and comment! *** "Fuckit, I'm cold." "Fucking freezing." "I'm starting to wish the pitch had frozen hard enough for the match to be...

Self Improvement

by GToast on Sep 16, 2017
Romance

This is another story based all too firmly in real life; there is much fictional about it, but there are uncomfortably real parts. Well, you write what you know, and I know something about this subject. It also came out a bit longer than I had anticipated. I try to corral my characters, as a rule; these refused, and the story kept writing itself until it re...

Suzy and 'Mistress' Danielle

by LucyCanyon on Sep 16, 2017
Transsexuals & Crossdressers

I have been chatting to a contact about our shared fantasies centred on her giving up a little control to me, but with me in my feminine guise as she and I both loved the feel and look of this. Finally, after a couple of earlier meetings - both involving sexual encounters - we met again, and we had the space and time to make some more of our shared fantasies...

Carrie's Curiosity Ch. 01

by anon1940 on Sep 17, 2017
BDSM

Prelude: For several months Carrie had been talking about her desire to submit her body to a rigorous training program. Throughout the time that I had known her, it was clear to me that she derived an erotic thrill from having her body pushed to its limits, even when that entailed considerable physical stress and occasional pain. In order to satisfy her crav...

Conceal Me What I Am Ch. 05

by Stultus on Sep 15, 2017
Sci-Fi & Fantasy

**************** CHAPTER FIVE As ass reamings went, I'd grade this one only a C+, but then again I'd been called onto the carpet and screamed at by real professionals before back home. Numerous times. My old bosses at the Austin BMA could give these USA wankers some real management lessons in the art of attitude adjustment, but perhaps with me they'd just e...

The Perfect Man Ch. 02

by Freakboy80 on Sep 18, 2017
BDSM

Please read the "Perfect Man" before reading this. This story is a continuation of that story. * It had been a week since Justin had seen Sandra. He talked to her on the phone everyday, but she had refused to see him until another week had passed. When he would ask to see her she would always remind him of what she had told him the last time they saw each...

LaFemme Michele: Paris Noir, Ch. 07

by Deckard Kincaid on Sep 16, 2017
Novels and Novellas

From far away, Barry was now in emotional hell after having watched his wife's gang bang, during which she had been penetrated by cocks that were nearly twice the size of anything that he had to offer. Especially troubling to him, was the sight of the beautiful and masculine hermaphrodite who had been the last to fuck Michele before the video connection was...