Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

Day After Class

by ArousedAmy on Aug 18, 2017
First Time

My sexual adventures started when I was a senior in high school. I had a few boyfriends but was only sexually active with one. We had to sneak around so we could have sex, which might have made it more exciting. Once I started, I could not get enough of it! In May of my senior year, I needed some extra math help so I could graduate. I went to see my teache...

Cannonball Belly Fever

by Subtext on Sep 1, 2017
Fetish

One day when Tom was leaving for lunch from his substitute teaching job at a grade school, he spotted a Mexican mother with two of her children in the parking lot. She wasn't beautiful, just plain-looking, but she was hugely pregnant! Now Tom was not a dawg by nature or even a guy who got off on every pregnant woman he saw, but this one was different. So d...

Law School Ch. 01

by chicagosslut on Sep 1, 2017
Group Sex

The blonde in your first ever class of law school catches your eye, even from across the room. Intoxicated with the sight of her hair brushing her tan skin, you sit down beside her before you even know what you're doing. As soon as you do it, you see my face in your mind and feel a surge of guilty. Looking around the room, you see a lot of guys who are proba...

Wishes Come True

by mojobwoikin on Sep 17, 2017
Loving Wives

I was in a variety of relationships, before I met my future wife, and was in a few relationships, during the time we were seriously dating. The last two women in my life, before the engagement, were very open sexually and had additional people join us in our bed on multiple occasions. I was never able to convince my wife-to-be to engage in sex of this type,...

A Slow Unwinding Ch. 01

by deSilentio on Sep 1, 2017
Group Sex

"Alright, love, I'll be there in about five minutes." John closed his cell phone and pulled out of the parking garage. Behind him in the car, piled up on the back seat, was an absurd amount of luggage for a single week vacationing on the North Fork. It had all been carefully packed that morning by Sara, his girlfriend of four years, who now awaited him outs...

A Grade Training Camp

by daysleeper on Sep 14, 2017
Group Sex

Upon my arrival at the training school a woman met me in her 30's who took me to her office to explain to me the training techniques that took place here and to explain to me the rules that I must abide to while I was here. "We train the girls here to please their husbands when they are chosen and bought from us here, as you know." She then turned on the mi...

Heather & Mrs. Harley Ch. 01

by UBU on Sep 14, 2017
BDSM

We moved, my Mom and Dad and me, to a new, bigger house my senior year of High school. Forget the “better” neighborhood -- for me the principle advantage of our situation was that I now lived next door to my classmate Heather and her mother, Mrs. Harley. Heather was one of the wildest party girls around and Mrs. Harley was a teacher at our school, still youn...

Loops

by MusicianElf on Aug 18, 2017
First Time

There's a place I know off the bike path near Alexandria, Ohio. You pull off, go down a tractor path through a bean field, then through a stand of sycamores and maples to a swimming hole in Raccoon Creek. I left my virginity there on August 17, 1976. Of course, there wasn't a bike path then, just the tractor access from the road. Kids used to go there in t...

Fingered at the Game

by Exporoni on Sep 11, 2017
Exhibitionist & Voyeur

In school I was a cheerleader and what better way for people to look at you than to be cart wheeling, leaping and jumping in front of hundreds of people. Though I hated Home EC I made use of the Susie Homemaker sewing skills. One of the first things I did was make my cheerleading uniforms tighter. Then there were those tights. We had to wear tights under o...

My Chemical Romance Ch. 07

by velvetpie on Sep 16, 2017
Toys & Masturbation

"That was amazing." Rita breathed, no longer shy about being naked as she lay between Casey and me. "Jesus, I've never cum so hard in my entire life." "Me, either." I started putting my clothes back on until Casey touched my hand, stopping me. "You're leaving so soon?" "Well, I want to take my stuff home and start practicing." "Are you sure?" She rubbed...