Gay Sissy Stories

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Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...

Sissy con carne

by WinterBreeze on Sep 26, 2017
Gay

You've always known inside that you we're far less heterosexual than everyone might think. It's been a long time since you imagined you were the man getting sucked and fucked in the porn you watch you can't help but imagine taking delicious juicy cock into your mouth and even your ass you'd love to feel these pleasures for real. Luckily fortune seems to be i...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

Sissy Cuckold & The Old Bull Ch. 02

by DirtyDaddyHunter on Sep 19, 2017
Gay Male

"Now for your turn" leers the old bull, stroking the mushroomed head of his gnarled old cock. The old man starts to get hard again and grabs the husband's head. He slams his cock back in the husband's mouth, brutally facefucking him. "Is that what you want Sissy? To be Daddies pantied cocksucker? "The husband chokes and gags on this vile old man's big cock,...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

Sissy Bottom Has a Nite Out Ch. 04

by lostsoul1974 on Sep 14, 2017
Gay Male

Well, following some completely depraved sexual exploits last weekend, I entered the workweek thoroughly satisfied! For those of you not following the series, (see my cocktales) my fuck buddy Eric and I had some really hot gay action at a local Theater, as well as a raunchy, fem-dom 3-some with my wife Toni at home where she showed me all over again why I...

Sissy Bottom Has a Nite Out Ch. 03

by lostsoul1974 on Sep 14, 2017
Gay Male

After two wild and raunchy nights at the local ABS with my fuck-buddy Eric, I still had one night left while my wife was out of town. Eric and I were both pretty whipped (and sore) after the previous two nights play, but opportunities like this only come up so often. We had gotten in late from last nights adventure and crashed in my bed without even showerin...

Sissy Bottom Has a Nite Out Ch. 02

by lostsoul1974 on Sep 14, 2017
Gay Male

Last night, my friend Eric and I had some really hot sex down at the Adult Theatre. Eric had me wear a pair of my wife's panties and I was a sissy fuck-boy for a whole theatre full of horny men. My wife is out of town for the weekend, so we are gonna be as lecherous as two bisexual fuck-buddies can be. This morning, I awoke to the sensation of Eric's hand s...

Sissy Veronica

by slavegurl_veronica on Sep 16, 2017
Gay Male

Hi. My name is Veronica. I am a 21 year old, 135 pound, pale white sissy boy with dark brown eyes and hair. My master is Derek. He is 6 ft 5 in, 175 pounds of beautiful black stud. I have a sissy playmate named Alex who is also Derek's pet. As I already described in an earlier story, Alex's sister Cecilia is responsible for hooking us up with Derek and intro...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...