Crossdressing School Stories

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Master's Degree in Crossdressing Ch. 01

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

This series is the follow up to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making confessions to the public for the first time, my wife has generally been aware o...

Confession

by holukukkar on Dec 10, 2018
Transgender & Crossdressers

Hello Everyone, This all started when I was 18 years old. Just like any other 18 years old boy I was browsing through the porn website for some porn to watch when I came across a crossdressing video in which the man was forced to wear female clothes, accessories and makeup and then treated as slave to do household chores and then fucked in ass by strapon....

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...

Crossdressed by Hot Girls

by tgirlchrissy on Sep 16, 2017
Transsexuals & Crossdressers

While I was a senior in high school I had an experience I would never forget. I had a group of girls that I called my "Ladies" and I was always close with them, I even hooked up with 2 of the 6. One summer night there was going to be a party and they were all going so me and a couple of my friends were going to go too. Earlier that day I was hanging out with...

Forbidden Codex

by TheCanadian on Aug 30, 2018
BDSM

You’ve got a freind named Denise, with a strong interest in the supernatural--something you have in common. At times, it seems she has a crush on you, but you’ve been friends for years. Besides, Denise was just older than you by enough that you figured she didn’t think of you that way. One afternoon, you knocked on Denise’s front door. When the door opened,...

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The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Transnational

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Malcolm Nyland was looking forward to his farewell party; he was leaving a job that had not only been a drudge, but had been a constant source of angst and worry. Malcolm worked for MI6; not in any capacity that involved glamour, mystique, danger or intrigue. Malcolm was a database analyst, and although he had a top secret security clearance, his job was on...

Pearl Ch. 02

by allourdesires on Oct 22, 2019
Transgender & Crossdressers

The fact that Her boyfriend would be coming over to my flat, on the evening of my birthday, to bring Lori out was enough, of itself, to overshadow my whole week but, add in the fact that she had told him all about my crossdressing and our relationship and I would have spent the entire week cowering in my room! I think Lori realised that her actions had inst...

Becoming My Neighbor's GF Ch. 01

by BaileyJensen on Sep 12, 2017
Transsexuals & Crossdressers

This story is focused on a guy getting swept away in the world of crossdressing, only to find his neighbor has equal interest. Pretty tame stuff, compared to everything else I write. Enjoy! ***** I had always considered myself somewhat feminine, but I never thought it would get this far. I grew up in the suburbs, and my family was always a bit out of plac...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...