Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

Silken Seductions - Step 01

by AdamZasse on Sep 14, 2017
Transsexuals & Crossdressers

It was one of those days at work. Nothing was going right and I was getting a headache. I slipped out a half-hour early and headed home for aspirin and a hot shower. I was surprised to see my husband's car in the driveway so I thought I'd surprise him and get him in the shower with me. I stripped down to just my panties while still down stairs and padded qui...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Arabian Nights Ch. 01

by kayla_femboi on Sep 14, 2017
Transsexuals & Crossdressers

I was in Dubai for business. I was essentially a salesman for a company that specialized in medical equipment for hospitals. Nothing terribly exciting, but the pay was decent and I got to travel quite a bit. I wasn't cruising around the world in first class by any means, but the companies would put me up in hotels for the trip. I loved this since it gave the...

iPad Roommate

by Oddballs on Dec 31, 2020
Science Fiction

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, b...

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The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Staying Together

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"I'm not sure further sessions will be of much use to either of you. After seeing both of you twice of week for two months, neither of you is any closer to resolving your concerns than we were when you first came to me." Dr. Nelson was good. She had the ability to examine a problem, bound it, and then dissect it into smaller pieces. She'd done that with bot...

Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...