Gay Crossdresser And Sissy Stories

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Infinite Scroll

The Fallen Ch. 08

by Acacia_wolf on Sep 14, 2017
Gay Male

This story contains characters 18+ Author's Note: Hey everyone! Here's the next chapter of The Fallen. Sorry if it took me so long to post. I am working on two other stories I plan on posting soon as well. As for you my readers, thank you for all the support and feedback! I have read your messages and comments and anyone is free to add me on Facebook! Rose...

Night Games Pt. 02

by EROTICbearscribe on Jul 17, 2019
Gay Male

I stripped down to my boxer briefs, turned off the light and joined the two of them on my bed. I lay there for a second, processing everything. It had been a while since I had shared my bed with anyone. Much less two people. Much less two other guys. It was a lot to take in. I could feel the heat we were generating under the thin sheet that covered us. The...

The New Slave Ch. 08

by martin_x59 on Sep 14, 2017
Gay Male

At five thirty Shane, Joe and myself get in the van and climb into the back. We pick up the blindfolds and I'm about to put mine on when my phone vibrates. It's from Sir again. "Tie their hands behind their backs then put on your blindfold." "I'm to tie your hands," I tell them, "Sir's orders." I find leather restraints in the back of the van and I tether...

Bright Arrow Ch. 02

by dagan732 on Sep 25, 2017
Gay Male

Kevin woke the next morning and headed to the bathroom to release a steady stream of piss into the toilet. He hadn't drunk in a while and though he hadn't had a lot, the beer still had left his bladder full and his head feeling funny that morning. He flushed, and made his way into his office. "Computer?" Kevin said as he sat down in front of his terminal....

Diary of a Cock Sucker Ch. 07

by Bicyclist on Sep 14, 2017
Gay Male

It is all in slow motion. I see his bare chest above me. My gaze travels downward; the smooth hairless belly, his fantastically engorged cock jutting out. He has a condom on but it is translucent. And I can see the lovely olive skin of his hard shaft. A gorgeous rolling pin shaped cock. He thrusts his hips and I feel his cock drive into me. I hear myself cry...

Satisfaction Ashram

by sr71plt on Aug 30, 2017
Gay Male

As I stood outside the entrance to the old British colonial-style Windsor Hotel in Nuwara Eliya, Sri Lanka, in the shadow of Mount Pidurutagala, waiting for someone to take me up to the ashram, I couldn't believe how far—and how far back in time—I had moved from Teddy's cabin in the Catskills. From the moment Teddy's business partner, Mort Whitley, had drive...

Bangkok Defection

by sr71plt on Sep 14, 2017
Gay Male

I froze in the middle of talking about the next season of the Bangkok Chopin Society at the ambassador's residence, as the ambassador walked into and around the side of the room to get into another room. I don't know if I audibly gulped or not, but none of the women—and the few men—sitting in a circle of upholstered chairs and couches in the commodious room...

Cabin Fever Ch. 03

by DerelictionOfSanity on Aug 17, 2017
Gay Male

I woke up after a night of unusual dreams. For the most part, they hadn’t been unpleasant, but the last one had me sitting bolt upright in bed and sweating profusely. Strangely, I couldn’t remember anything that had happened in any detail, just a cold fear in my stomach as I faced something terrifying. My breathing slowed down to a normal rate as I let mysel...

Becoming a Gal Friday Pt. 05-06

by Showoff888 on Sep 14, 2017
Gay Male

Oh my god! I'm naked except for a pair of slutty fire truck red platform high heels, you know the kind you call 'fuck me shoes'. I'm on a bed with David this great looking black guy and Saul, his white gay curly brown hair partner, with the dashing goatee, kind of a Jewish swashbuckler thing going with that goatee. Saul and David are built tall and solidly m...

My Voyeur Love Affair

by 69clambake on Sep 24, 2019
Gay Male

I went to college at a medium sized university in Southern California. My junior year, I lived in a nice little one bedroom studio apartment off campus. My building was one of about ten two-story apartment buildings scattered around a nicely landscaped complex. My apartment was on the second floor of my building. Out my front windows, I had a nice view of a...