Sissy Trap Stories

19,529 results
Orientation
Length
Source
Infinite Scroll

Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...

Mistress Circe

by justincbenedict on Jul 31, 2018
BDSM

PROLOGUE Lara lay on her bruised back, with her legs stuck out. She had clothesline, tightly tied to her big toe on each widespread foot, with the other end attached to a nipple clamp pulling each breast, and the rope wasn't long. This was a tougher situation than last week, when Circe had Lara hanging from her wrists, and having to run her fingers around...

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

The Unsuspecting Candidate Ch. 01

by missvicky53 on Sep 11, 2017
Fetish

I had been told what to expect and there he was, my next candidate! Even if I hadn't been told about this one, I would have recognized the potential he exhibited. How did I know this? I can't really explain it in mere words. All I can tell you is I knew this one would be susceptible to what I had in mind. I had been watching him watch me for more than ten mi...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Sissy Prince: Origin Ch. 01

by SatinSlip on Feb 6, 2018
Fetish

Prince Oliver skipped through the castle garden. He loved the green and the flowers. He was nineteen and yet to be married. In truth his parents had coddled him as a boy. He knew his numbers and letters. He knew how to run a castle and a kingdom. On paper anyway. But he would never be a warlord. Never be a brave leader of men on the battlefield. His gold...

The Chemical Pt. 02

by mountian299 on Sep 15, 2017
Novels and Novellas

CHAPTER 14 Bobby was eating his mother out. That cum in her cunt was delectable combined with her juices. Soon Dora came standing up her legs almost giving way underneath her. Bobby was content then he asked master, "Could I play with my mother's tits?" Dora spoke up, "Master please he is my youngest son." "Dora you have not learned you're my property t...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

The Club Pt. 01

by Paulateevee on Jul 13, 2020
Transgender & Crossdressers

This is a continuation of 'The Trap'. It would be best to read that story (5 parts) first before reading this one although I will try to make this story as stand alone as I can. Background - Paul has been outed as a cock sucking sissy to his friends, family and work. He's lost his job, his wife and friends. Louise offers him a way out. Usual disclaimer. An...