Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

The Capture of Sweet Pussy Ch. 03

by SirStroker88 on Sep 17, 2017
BDSM

Chapter 3 – Donna's Story 'Damn Sid, you're right, she is a beautiful sight." Donna was looking down at Pam Martini, the bitch she knew from the office. What she saw now was a frightened young lady on all fours wearing nothing but a collar and a blindfold. She was leashed to a whipping post and quietly sobbing to herself. Donna knelt and stroked Pam Sweet...

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

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The Journey Pt. 03

by MissYellowPanties on Sep 14, 2017
Transsexuals & Crossdressers

Training It was an unusual feeling walking down the corridor, my sissyclit was hard with excitement and I had not yet adjusted to the feeling of the butt plug placed firmly in my boypussy. I still tried to move in a ladylike fashion, but the strange sensation was overwhelming and I stumbled suddenly out of time with Mistress Anna's gait. Mistress Anna...

Neighbourhood Terror to Sissy Pt. 18

by Fibaro on Mar 10, 2020
Transgender & Crossdressers

Chapter 20 Marcy had a wonderful night's sleep while she didn't realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn't realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his s...

Girlfriends (Chandra and Nikki)

by girlygay on Sep 14, 2017
Transsexuals & Crossdressers

Nikki and I brought Adam and Dave back to his place. We told the boys to make themselves comfortable while we touched up our makeup and raided Nikki's stash of girl clothes for sexier stuff to wear. "Wanna do a group thing?" Nikki asked me, helping me into a bustier and garter. "Like, share our men?" I asked, pulling a black satin negligee over my tits. "...

Michel and Brent Get Suited

by Sarahcheer on Sep 13, 2017
Transsexuals & Crossdressers

A Continuation of the slave college series * Michel Jenkins and Brent McMasters were freshmen at the slave college. After just celebrating their 18th birthdays, the boys had enrolled in the school, both for the academic achievements of past graduates, and because it was rumored there were 6 girls per guy on the campus. Being boys, both were thinking it wou...

How I Became Vanessa Ch. 01

by vanessa_brown on Sep 16, 2017
Transsexuals & Crossdressers

PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only...

Call Me Katie Pt. 01

by KrierWitz on Sep 18, 2017
Transsexuals & Crossdressers

This is the first part of a story following Kent Wiltshire and his journey from an independent man to a submissive slave girl. Please let me know what you think, and if there is any themes you would like to see incorporated in the future. ***** My name is Kent, I'm 22 years old and live in a two-room apartment in Stanley, Idaho. It's a small city, with ju...

Julie is a Whore Ch. 08

by Pretty_Sissy_Julie on Sep 14, 2020
Fetish

My name is julie. I am a sissy CD that has been working in a brothel for years now. During the week I am a male teacher named Julian, but on week ends and vacations I am a sissy whore that is the property of the owner of the brothel, "Madame." My sister, Becca, also works in the brothel. Since I am a slave there, Madame has given me my own room. Madame has...