Gay Cross Dressing Stories

3,703 results
Orientation
Length
Source
Infinite Scroll

Top or Bottom Ch. 01

by sandyvalleylad on Aug 30, 2017
Gay Male

MWM 7" Cut Looking for c/d Top Those seven words in a personal ad in our local gay/lesbian weekly got me thinking about what I wanted in my sex life. I've been married, dated a woman and am now married again but I've never tried having sex with a man. Hell I didn't even know the lingo -- what's a MWM and is a Top the person who's on top? I needed to underst...

Alice, My Uncle, & Me Ch. 04a

by John Hill on Sep 14, 2017
Gay Male

This continues the account of the of five days and nights that studly 18 year old Mikey spends together with Mike, the 24-year old uncle he idolizes, and Mike's fascinating and beautiful 22-year old fiancée Alice. The beginning of their story is told in "Cross-Country with My Uncle," and continued by "Alice, My Uncle, and Me," day 1 and day 2, and Day 3, par...

Humanities 301: A Lesson in Life

by LuciousBi-Writes4U on Sep 16, 2017
Gay Male

Dan and Mike where students at the same university, and after 3 years they finally crossed paths in Humanities 301. Dan was a very shy, uptight young man, very serious about his studies and his life goals. Mike on the other hand was a performer, and was the resident pretty boy dancer who knew he had the talent to go somewhere big one day. So what, or shall w...

The Fallen Ch. 02

by Acacia_wolf on Sep 14, 2017
Gay Male

Thank you for all the comments on the previous chapter I hope that this chapter and so on will be better thanks to your comments and suggestions. I hope you readers enjoy! All characters are 18 years or older. * Finding a white button up shirt and a small pair of old jeans, Seiji helped Tenshi get dressed. He smiled at the strange teen, he seemed so energ...

Castaway Love Ch. 01

by kwchancellor on Oct 29, 2018
Gay Male

I awoke to the sound of a roaring I couldn't place and a pounding headache. Forcing my eyes open, I saw blue, a deep sky blue. I turned my head to the left and saw a row of thick mangroves and palm trees. To the right I saw the ocean crashing on the shore. I was on a beach. Sitting up, the world tilted, and I was hit with a wave like dizziness that threw me...

The Ffitch Nortons

by RickyRooster on Sep 16, 2017
Gay Male

Notes for the Reader This is my second submission to Literotica. This story is intended as the first tale in a series describing the sexual experiences of a young man through University and his relationship with a hedonistic family with whom he becomes more than acquainted. There are some elements of my real experiences woven into the series but overall it...

Doing Nate a Favor

by ibjtjones on Jun 19, 2018
Gay Male

I got a call from Nate, David and I introduced him to Bruce, and they hit it off great. He wanted us to "surprise" their friend Tanner and fuck him silly to help get him over everything that had gone sour in his recent life. Nate said he had always fantasized about big black cocks like ours. They had given him the code to the lake house and he'd be visiting...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

An Afternoon 'Bi' the Pool

by Rckymtn110 on Aug 18, 2017
Gay Male

I had always felt a little different growing up. I was probably a little more sexual than most people were, but it was a private thing. I didn't sleep around or do anything most would consider wild; but nonetheless, a part of me was different from most guys. It is difficult to explain, but it is as if I have lace under my exterior of leather. It wasn't an ev...

Bathhouse Lessons

by glory_first on Aug 30, 2017
Gay Male

Thursday provided a rare opportunity to spend an entire late afternoon at the bathhouse, before meeting my wife at a public mixed sauna at 7pm. I'd arrived a bit later than normal, but the number of visitors seemed small. Finishing my beer at the Internet PC, I'd noticed several men entering. Going downstairs, the whirlpool was empty, and the number of tow...