Gay Sissy Piss Stories

4,102 results
Orientation
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It Could Be Worse Ch. 06

by eviltwin52 on Sep 14, 2017
Gay Male

In chapter 5 Leon took control of what he called his new sissy and fucked Cin into submission. We both became addicted to his superior black cock. Besides falling for his cock, Leon's predatory nature was evident. He wants Cin and I to prostitute ourselves for him. In the throes of black cock lust, we agreed. It could be worse Part 6 "Did you remember t...

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

Number 86 Ch. 06

by SaucySexySlut on Sep 16, 2017
Gay Male

This is the penultimate chapter of Mark's varied experiences at number 86. This story is fictitious and all characters depicted are 18 or over. Any resemblance to anyone real is purely a fortunate coincidence on their part if this is what they enjoy. * Kevin sat almost motionless on his chair, his legs kept apart by the spreader bar on the floor and his l...

The Man Cherry Fetish Ch. 01

by blondeallover_00 on Sep 2, 2017
Gay Male

This is the story of how I came to be an Asian cock and ass freak. I had no idea how much I craved dick until I became a student in the eastern U.S. I was attending a party that was being thrown for the better students in my department by professorial graduate school assistants. The event was located at a professor's home who was known to "swing both ways",...

Juera

by nancyvasquez on Aug 18, 2017
Gay Male

My name is Kevin Jean Bardot and, yes, I am a sissy. Most guys of my age had matured to where they had begun to look and act like men. I was small and skinny and had no body hair to speak of other than a few sparse, very blonde hairs on my pubis. I had sex with another person for the first time when I went into the navy and was stationed in a small city...

How I Became a Sissy Pt. 03 - Final

by Yngwhiteboi on Jan 23, 2019
Gay Male

Abdul opens my door and I slip in, then swing my legs in. He closes the door. He gets in next to me and starts the car. As we back out the drive, I ask "Where are we going sir? I thought I wasn't allowed to remove my new collar? Did I displease you?" "I wasn't displeased but the collar is for home and special occasions, not for everyone. We are going to my...

New Neighbors Ch. 01

by chained_sinner on Aug 31, 2017
Gay Male

I was so excited. A new city, a new apartment....a new life! I was newly divorced and ready to meet someone to settle down with. Someone nice to see the city with, laugh with, and maybe start a family with. It took me more than four days to get everything unpacked and set up to my liking, which left me just three more days before I was scheduled to start my...

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...

At the ABS Again

by TerriC on Sep 21, 2020
Gay Male

I was 18 when I sucked my first cock. A trip to the local adult bookstore had ended with me blowing the owner. This was already told in a previous story, The Book and Video, if you're interested. After a rather shameful departure on my first visit I did manage to make it back for another round, with much better results. After those first few visits, I real...

The Making of an Army Slut

by raylene on Jun 25, 2019
Gay Male

My name is Kevin and this is my story. I was raised by my mother. My dad died in a car accident when I was four. My mother done her best. She never remarried and focused her time on providing for her little boy. I was finishing high school. The small town in southwest Georgia didn't have much to offer. I had the grades but not the funds to go to community...