Gay Crossdresser Stories

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Orientation
Length
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Infinite Scroll

My Life as a Maid Pt. 01

by MissYellowPanties on Sep 16, 2017
Transsexuals & Crossdressers

Outcast My mom bailed me from the county jail after my DUI arrest. I had only been inside for a few hours, but I'd never been more worried or bored in my life. When we got home, my rucksack was waiting by the door, all my worldly possessions were packed in it, my father picked it up, threw it at me, and invited me to leave his house. That sucked. I w...

Stocking Tops

by Egmont Grigor on Sep 13, 2017
Fetish

Chapter 1 Mr and Mrs Peach were called for a urgent meeting with Headmaster but as Victoria Peach was home alone, Albert being on a Trade Mission to South Africa, she went unaccompanied to Tucker's College for Boys at Stitchbury. By the sympathetic look on the face of the woman ushering her into Headmaster's dark paneled study, Victoria stomach hurled to it...

Tapestry Ch. 01

by HLD on Sep 12, 2017
Novels and Novellas

Chapter 01: A New Love The relationships we have are threads in a tapestry, each woven together to show the life we have lived and connections we have with one another. This is the first of an open-ended series that will feature characters from some of my past stories, and introduce some new friends for us to get to know. It picks up right after "McKayla's...

Jamaican Beauties Jaunt Ch. 09

by TB_OrNot2B on Sep 15, 2017
Novels and Novellas

Chapter 9 - Risqué Tours: Her mother adds spice to the Jaunt. Notice: The author listed Jamaican Beauties Jaunt under Literotica's umbrella category Novels and Novellas: Erotic fiction with a broader scope. However, the events in this chapter cover a variety of Literotica categories including: Exhibitionist & Voyeur: this chapter includes the adventures of...

Spoiled Princess Hates Camping Ch. 04: Final

by RetroFan on Sep 13, 2017
Fetish

INTRODUCTION & DISCLAIMER - Welcome to the hot, steamy and hilarious ending to 'Spoiled Princess Hates Camping', a kinky comedy set in 1994. Madison resolves to change herself and be less spoiled and selfish, but will it last? Can Davo, the brash, loud Australian achieve his goal and bed Madison? How about country girl Kate and Davo's New Zealand friend Tra...

Berlin Diary (A Virgin's Release)

by XXscribbler on Apr 2, 2018
Erotic Couplings

It had been a long, hot day – first a 60 kilometer bike ride through variously developed – or variously dying - bits of Berlin, complete with small, well-done on-site lectures by the three German women grad-student guides. Then, afterwards, a semi-obligatory trip to a local night-club – complete with ten-foot visibility due to cigarette smoke. Ugh! And aft...

Hush Little Baby Ch. 11-15

by LoneGirl on Jan 20, 2020
Romance

Chapter 11 "A natural birth is possible," Jared smiled as he entered his office. "What are you guys arguing about?" Luciana leaned back in the chair and crossed her arms, letting her hair fall down the front of her sweater dress. "Chris doesn't want me to have a natural birth," she grumbled. "I never said I didn't want it!" He protested, straightening him...

It's Your Life

by Ephesus14 on Nov 16, 2020
Loving Wives

One good thing about writing is if you make a mistake, all you have to do is hit Backspace to correct it. Real life isn't like that. If you make a mistake, it can cost you a friend. Real life doesn't have Backspace. It's your life. .....Live it the way you like and fuck who you want. The Board of Directors of our little theatre group was having its monthly...

Little Man Pretty Girl Ch. 01

by Scribler on Sep 12, 2017
Transsexuals & Crossdressers

Why I went to the club I didn't know. I guess it was for something to do. I had been alone for so long that I needed the company of others. Even if they did treat me with disdain I still needed to socialize with other humans. You see I live alone and I work from home. I do security consultant work for companies that are having trouble with hackers. Recentl...

The Book of David Ch. 05

by bluedragonauthor on Sep 12, 2017
Group Sex

*** -- CHAPTER 5: The Sisters -- *** FALL QUARTER, JUNIOR YEAR (September 2000) Friends. I could handle being friends. For some reason, having sex with E-Beth gave me closure with her. I'd subconsciously spent the entire summer with her in the back of my head, wondering how we would act around her when we met up again at school. Now I knew. And I knew...