Crossdressers Stories

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Orientation
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The Life of Janice Ch. 03

by Kim_Oh_No on Sep 13, 2017
Transsexuals & Crossdressers

Her name was Cindy. The barista at the coffee kiosk. I ordered that coffee as Janice, I paid for that coffee as Janice, I made a friend as Janice. She was a petite brunette; pretty eyes. I discovered my voice wasn't as masculine as I had feared as long as I softened my tone and spoke with intent and sincerity. When she got off work, we sat and talked for...

The Psychosexual Motive in Writing

by Da_Vida on Sep 16, 2017
Reviews & Essays

I have been a writer all of my life. My employment as an adult has, to a large extent, depended on my ability to get published, which I suppose makes me a professional writer. In addition to writing, I've also served as a consulting editor for a number of publications. I am no stranger to the written word. The motives for writing erotic fiction no doubt va...

The Parking Lot Ch. 01

by LatexSolarBeef on Jul 13, 2020
Transgender & Crossdressers

My buddy Robbie, an old family friend, is much younger than I am by nearly 20 years. But we've always been close and enjoy hanging out. He was working as a landscaper one summer while in college. He invited me to hang out at a bar in Lavallette where he and his pals shot pool and drank beer on weeknights. It sounded relaxing, so I went. Only one other guy w...

A Great Day Off Work

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Days off are great. Any day off is a great day. You can catch up on things, relax, take care of business, chill out, and just have a good time. Days off also open the door to many opportunities and possibilities. This day would prove to be a very good day. My wife was working this day, and I had taken the day of from work, just because. I stayed home and d...

CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

My Secret Revealed Ch. 05

by jealouscuck on May 30, 2018
Transsexuals & Crossdressers

The trip to New York was indeed the watershed moment in our relationship. Karen was showing me off as her submissive husband. I could have been resentful of the way she had me come out, but I was enjoying the excitement too much to complain. She had made such a show of chastising me when she found out about my fetish because we were not to have secrets from...

The Perils of Young Guys

by Etaindarcy on Aug 7, 2019
Transgender & Crossdressers

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up. I met Jack and Kyle in...

The Panty Raider

by ValoryG on Oct 30, 2018
Transgender & Crossdressers

There, I did it again. Filching another pair of delicious panties from an unsuspecting girl - well, young woman. I'm a sophomore at a conservative Christian college in Tennessee (Robb Relertson College) and I'm having problems balancing studies and women. You see, the word seems to have gotten around that I'm a great kisser and well, great beyond that 'ol fi...

How I Became a Crossdresser

by Chrispe69 on Sep 16, 2017
Transsexuals & Crossdressers

I've always loved everything about women. I love their curvy feminine features, their long painted fingernails, the high heels they wear and their silky smooth clothing. When I was young, I liked the women I dated to be flashy and slutty looking. I never had much trouble getting the sex I was after from these women either. I got married in my late twenties...