Gay Crossdressing Stories

23,246 results
Orientation
Length
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Infinite Scroll

The Rendezvous Ch. 01

by CassidyCaine on Sep 26, 2017
Transsexuals & Crossdressers

(Author's note: I have tried to get an editor for this story but failing that after over a week of looking I'm publishing it. Please be aware this work has some fictional coercion and other sissification elements.) Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed t...

Me & My Wife Are Sisters Now Ch. 01

by gayindia1980 on Sep 16, 2017
Fetish

Hi I am Ravi, 28 year old from Delhi 5.8, slim, hairless and minimal facial hairs. I am married for 3 years, my wife Shivika is 24, 5.4, slim and beautiful. I was in crossdressing since my school days. I use to wear my sister's and mom's clothes when nobody used to be at home. In 12th class I lost my virginity to a college guy whom I met online but that anot...

Caught For the Last Time Ch. 07

by TGJamie on Sep 15, 2017
Transsexuals & Crossdressers

We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top. "That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head. Th...

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...

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...

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

How Marissa Became a Woman

by CDSean on Sep 19, 2017
Transsexuals & Crossdressers

This is a work of pure fiction. It deals with adult subject matter including crossdressing, and consensual male on male sex. If any of this offends you, please stop reading now. This is my first story for others so any feedback would be appreciated. ***** Henry and Lisa have been married for many years. During that, time both of them made many little pe...

Cocksucker: Drag Queen

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is turned into a twink and drag queen. You do not need to read the first parts to enjoy this story of a straight man who gets submerged into the drag queen world of San Francisco. (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first five chapters...