Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

The Journey Pt. 01

by MissYellowPanties on Sep 13, 2017
Transsexuals & Crossdressers

Part 1 The Journey. I sat in the back seat of the car, my legs stretched in front of me and crossed at the ankles, the short skirt I wore barley covered my panties, and I could feel the cool leather of the seat press against my legs. I smiled at the reflection of the drivers hungry eyes in the rear view mirror, longing, lust, and power, mixed together in...

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

My First Feminization Pt. 03

by npbear on May 29, 2018
BDSM

Startled by a hand sliding under my arm, I jump. The shock brings me out of my sex-induced haze and I realise that they are helping me up, off the cushions, onto my feet. Slowly I tune in to the fact that they're actually talking to me as they pull. "You poor dear," a gentle voice says "they just left you here, didn't they? No one picks up after themselves...

It's Just Dinner Honey

by justme6996 on Oct 8, 2019
Fetish

This story is about cuckolding, and forced bi , if this is not your thing please find other stories that are. I would love to hear your opinion regarding the story, in commends/messages. Thanks P.S. English is not my main language and their might be some grammar mistakes here and there. Also, this is the first story i am posting in here... if there are g...

My First Experience as a Femdom

by lushusboobs on Sep 11, 2017
BDSM

I'm a 40 year old bisexual Femme Dom, but I wasn't always so open minded about my sexual interests. I came from a very rural, homophobic sort of background. Homoeroticism, bisexuality, or reverse role playing were strictly taboo for me. Perhaps one of the reasons why anal sex and strap on penetration has held such a fascination for me is because it because...

Sarah was Trained to be a Girl

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I love to search on-line for sites related to crossdressing, that's how I found Literotica. I've also found sites for 'Men in Panties', videos of crossdressing, girls clothes for men, etc. One time, I was really lucky, I found a site offering a weekend of 'girly training'. We would be taught how to walk, sit and act like a girl. We would be dressed the whole...

Sissy Prodigy Ch. 01

by daisyboi_sissy on Sep 15, 2017
Transsexuals & Crossdressers

If you are offended by sexual content please leave now. This is a work of fiction. Everyone in this story is above the age of 18. Thanks for your comments and ideas for future content. * "I have no idea what you are doing, and I don't want to know Kel. All I know is that something is going on while I am not here and I ought to call the school to have his...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...