Gay Transvestite Stories

71 results
Orientation
Length
Source
Infinite Scroll

Yet Another Frat Initiation Story Ch. 07

by Cyanlot on Aug 18, 2017
Gay Male

Part 7: Fraternity Service The morning's activities were once again labeled cryptically, this time as "Fraternity Service". When we got down to the breakfast table, we found that there was no food there. Instead, there was a note that said that pledges were required to service fraternity members before they would have anything to eat. We were to draw a name...

Tennis Interview

by sr71plt on Aug 18, 2017
Gay Male

"Perhaps stand over there at the center of the net with the grandstand and the Bangkok skyline in the background." Dent Douglas tore his eyes away from the young man who was interviewing him; turned his gaze on the photographer, Rick Rodriguez; and then, with a smile, moved to the center of the tennis court net and struck a pose. He was a tall, well-built s...

Sharing Secrets Pt. 04

by Showoff888 on Sep 14, 2017
Gay Male

NOTE: This story entails piss play. ***** Hoshi slowly returns to consciousness and awareness as the wisps of sexual bliss begin to fade. He can feel the warmth of his naked body lying under the warmth of his friend's naked body. He can feel the mass of cooling river of cum that was deposit between his ass cheeks and is making its way down his ass onto t...

Lottery Winner

by KeithD on Jul 4, 2018
Gay Male

Gene jutted his buttocks out from the rim of the swimming pool on Deck 11 of the Jewel of the Seas as it steamed its way from Key West, Florida, toward Puerto Costa Maya, Mexico. Another young man was standing next to him in the pool in water that rose up to his and Gene's nipples. He was leaning on the rim of the pool on one elbow, the palm of one hand pres...

Alex in Wonderland

by Johnboy9 on Sep 16, 2017
Gay Male

Thanks in advance for any and all feedback and votes. I welcome all sent me. Please, 18 years old and up only allowed. Characters in this story are at least of that age as well, even if not indicated. I put this in the gay category though I am really not sure. Its a slow developing tale, unlike my other stories. It will again develop into a transvestite/t...

Pony Boy Ch. 10

by ChestersBoi on Sep 14, 2017
Gay Male

The story so far... Ben, when desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Ar...

Lady Fortune's Smile

by Malice2 on Aug 18, 2017
Gay Male

From deep in the bowels of Hell, the Prince of Darkness releases his hordes of foul, evil and dysfunctional minions bred for the sole purpose of showing up to roommate interviews. And I, Theodore, the legal head of household, must sit here through each horrifying, grueling one on one session with these abominations and remain cordial, collected and most of a...

The Bonus

by sr71plt on Aug 18, 2017
Gay Male

"Welcome to Key West, Mr. Jabril. You were quick getting out of the airport. Tuesdays are good days for traveling here." Scotty was standing there on the curb outside the baggage claim area at the Key West air terminal much like last time and the time before that. He was leaning up against a red Jaguar XK-8 convertible and looking oh so preppy: spiky froste...

Rich and Scott

by Markymark9053 on Aug 18, 2017
Gay Male

Chapter 1 Rich "Thats the last box," I told my friend Matt. "It goes in the kitchen" "I know how to read you know," Matt said. "Although your handwriting is so bad that I don't honestly know how I can read it." He got into the truck and pushed the box to me with a sly grin on his face. "What do you expect me to do with this? I can't lift more than ten po...

Ben Loves a Challenge Ch. 08

by PDreadful on Dec 9, 2019
Gay Male

**I promise this isn't the end, there's more Dean and Ben to come. I hope you enjoy. -Penny** What he'd felt after Laura left him felt shallow in comparison to the pain-coated emptiness inside him now. Nothing mattered anymore, Dean's cold dismissal broke something in him. Worst part was that he couldn't figure out where he'd gone wrong. Dean didn't call,...