Gay Sissy Caught Stories

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Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

Uncle Marty Pt. 02

by Marty Fisher on Dec 23, 2019
Gay Male

This is a spinoff of my Brotherly Love series where my brother's son discovers his uncle's special talents...Part 2 *** I never thought "tomorrow" would arrive, but it did, and I woke up with my small penis tenting my panties thinking about what I was going to do today. Rose was sound asleep next to me as I thought about what had transpired between my brot...

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

I Turned Myself Out Ch. 02

by drmweaver705 on Jun 9, 2020
Gay Male

"You worship cock," the sultry woman's voice on the video said. "You desire them in your mouth." I caressed my dick as I watched the latest CEI videos online With the kids away at college and my wife on a girl's long weekend away in distant New York City, it was time to lock the doors, turn off the lights, put the cell on silent mode, grab the lube and get...

Office Prostitute: Exotic Discreet

by Alluring_Crimson_Shifter on Mar 26, 2019
Gay Male

Monique, a fit and well groomed office assistant straightened her skirt, and pulled her panties out of her ass crack. She licked residual cum from her lips and swallowing once more to clear her throat, enjoying the taste. She said, "Merci beaucoup," and took the money from Mr. Johnson for the blow job. Monique had been earning extra money for showing her bo...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...

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...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...