Gay Cross Dressing Stories

3,703 results
Orientation
Length
Source
Infinite Scroll

Keep Me Safe Ch. 03

by miles801801 on Sep 14, 2017
Gay Male

Ryan didn't know what was worse as he sat at the hospital, the screams or the quiet. Miles was unconscious when the paramedics arrived and he didn't regain consciousness until reaching the hospital an hour ago. Then the screaming started. The desperate cries coming from Miles made everyone feel sick. These weren't the usual cries from a hospital patient, th...

A New Summer Experience Ch. 04

by TxSmutWriter on Jan 7, 2019
Gay Male

Thursday night, we went out to see "Mad Max", which I liked but she didn't. It was kind of cool to have her on my arm, and we encountered a few people that either knew her or knew me. Some of them raised their eyebrows like "THOSE two are together?" but seemed to accept it. Operation Beard was working. Dad bought the furniture Thursday and had it delivered...

Fellow Traveler

by T@nman on Sep 1, 2017
Gay Male

I don't like traveling for business on weekends, but there wasn't a choice since this business conference was important. It was billed to be an intense, week long session that would be productive and filled with new approaches, new ideas, new processes and techniques, new technology, and new business for your company. I'd soon see if that was all true when...

Do I Want a Sugar Daddy

by Sean943 on Mar 2, 2020
Gay Male

My name is Jason, I am nineteen years old and from the South West of Scotland and I have just completed my first year studying Tourism at an Ayrshire College. I don't have a career plan as yet, as I have still to work out what I want to do; this is my story. Although my parents are funding me through college, I also have a part time job in a local Morrison'...

Out in the Black Ch. 19

by outstandingunderground on Oct 12, 2020
Gay Male

This is a book-length work, so not every chapter will involve sex. If you're just looking for a quick wank, this may not be your story. Thanks for reading! ===== Moving in together did not cause the outcry the captain had feared. For the most part, it was barely even noticed. The XO had her say, of course, but as I'd expected, the vast majority of the cr...

Thoroughly Used

by CSK on Sep 14, 2017
Gay Male

Hey all, here is a nice bit of fantasy for you. As always, please exercise safe sex in the real world and live out these dangerous fantasies here. Please note, before reading, that this story includes a bit of cross-dressing (panties) but not really enough to place in the Transsexual / Cross-dressing category, hardcore gay throat-fucking and sex, public sex,...

Calvins

by sum12watch on Aug 18, 2017
Gay Male

God, I can't believe my eyes. I quickly slip on my sunglasses, both shielding my eyes from the sun and disguising the direction of my gaze. Yes, it's Adonis himself, leaning sultrily against the guardrail outside his third-floor apartment, nude but for a tight-fitting pair of boxer-briefs. Calvin Kleins, I'll bet. The white material is striking, because of...

Turning the Teacher Ch. 02

by Dave933 on Aug 18, 2017
Gay Male

I woke up early, sunlight pushing through the feeble barrier provided by pale yellow curtains. I was lying on a double bed in a strange room, and for a moment I wondered where I was. Then it came back to me. I was at my teacher's house, Mr. Wild. I had found a sordid and sexy video he had starred in before he became a teacher, and used it to blackmail him...

Freddie Pt. 01

by exaucer on Aug 18, 2017
Gay Male

At twenty two years of age it appeared as if I had it all. I was going steady with a very pretty girl. She was a student in another part of the country. I had a good job in the catering industry and I got on well with my new stepfather who was ten years younger than my mum. In the cafe where I worked I was popular with the clientele who were, in the main, ma...

Rick Needed a Beer, Gets Much More Pt. 12

by Iwanttwo on Sep 23, 2019
Gay Male

I was awakened by the rough landing and was surprised I had slept through the entire flight. I was glad I had all my gear in one carryon bag and headed straight to the rental car desk after getting off the plane. I rented an average rental as I wanted to have a low profile and keep to myself this week. After checking in, I looked around the hotel. It had a n...