Crossdressing School Stories

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My Pleasure

by Lucity on Sep 3, 2017
Erotic Couplings

“I’ll just leave the money on the desk. Is that all right?” Mrs. Markway asked as she slid her feet into her spectator pumps and adjusted her bra. “You were extra special today, Mr. Gregory. I’m surprised I can walk at all.” She looked at him stretched out on the bed as she buttoned her blouse. “Your stamina always astounds me. I must thank Mr. Powers for re...

Love At First Email

by cum_loving22 on Sep 17, 2017
Non-Erotic

Big thanks to MissBoePeep for helping with her amazing editing skills and friendly perosanlity that made it so easy to do this. Thanks :) This is my first post but all feedback is welcome. I have changed the name of the other person mentioned in this to protect their identity, this is a true story it's my story. I've written it so that other people out ther...

Faded Star

by standingstones on Aug 19, 2017
Erotic Couplings

I had just finished my third year at college and was back home at my parent's place. I was driving down the street towards the house when I noticed someone was moving in a few houses up from us. I didn't pay much attention and I headed home. The next day my Mom asked me to mow the lawn and so I fired up the mower and started to cut the grass. I hadn't been m...

Guy Talk

by ReedRichards on Jul 3, 2018
Loving Wives

This is the sequel to Girl talk, published on the 18th. If you haven't read that one first, this one won't make too much sense. This is another short one, because it details just one conversation. ***** It's pretty warm today, in the upper 80s and humid, with a few clouds in the sky and the possibility of thunderstorms later this afternoon. Hi, I'm John, a...

Heather's Revenge

by alphawaves on Jan 14, 2019
Fetish

Heather and Ryan Starwood were twin siblings. Heather was a gorgeous brunette with long soft legs, a nice ass and big double D breasts. She was smart, funny and had a great personality. Ryan was also highly attractive. He had a nice square chin, large muscles and a firm ass. In fact, most girls would agree he is one of the hottest guys in town. However, unl...

My First Time in College

by Total_ROM on Nov 18, 2019
First Time

I did not, by any means, have the most exciting time in college. In particular, my freshman, junior, and senior years were characterized much more by studying and school anxiety than they were with parties, belligerence, and especially encounters with the female gender. Freshman year I lived in a 'pod' with three other guys, two of whom would go on to become...

After the Fact Ch. 04

by cnhemingway on Oct 16, 2018
Interracial Love

SOOOOO much has been going on. I did NOT forget this story. I am finishing up a TON of work and still crazy with school. But here is the next chapter for Marcus! Enjoy! ***** Marcus had tossed and turned all night. His dreams were filled with Lila and what a future would have looked like together. They were the kind of dreams that felt a little too rea...

The Adventures of Astoria Morgan Ch. 05

by Longo_Afar on Oct 29, 2018
BDSM

Chapter 5 - Life Lessons As a top predator, Minx had a highly developed killer instinct. Toying with one's prey is all well and good, in fact often quite delightful, but in the end there must be an end. The prey must be brought down, the decisive blow struck. When the coup-de-grace arrived, it should come without hesitation or mercy. Minx believed that sh...

Hot for Teacher

by j_bakergal on Mar 25, 2019
Erotic Couplings

I'd re-read my message dozens of times. Still I was shaking, and couldn't bring myself to hit SEND. "Thanks for coming to my party! Sorry we didn't get to chat more...now that I'm graduated, does that mean we can finally hang out? :-)" I needed to be flirty & suggestive, but not desperate or inappropriate. Basically, I needed to not sound like a high schoo...

My Sexy Doctor

by drdick69 on Apr 8, 2019
Erotic Couplings

I met Lexi ten years ago while doing surgery. I am a general surgeon at a major hospital in Kentucky. At the time, I worked with the medical school attached to our hospital and allowed medical students to observe me during surgeries. The first time I saw Lexi, she was in a pair of scrubs with a surgical mask on. She looked like every other student that came...