Gay White Sissy Stories

10,754 results
Orientation
Length
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Infinite Scroll

Beauty and the Beast Pt. 01

by Suzzique on Dec 17, 2017
Gay Male

I hesitated a long time before I advertised on Craig's list. I was 18 and had left school two months before. I had a place at university for the following October, almost a year ahead. I was living at home and had a mindless temporary job in a solicitor's office that made no demands on anything but my time. I'm a very shy person and no one knew I was gay exc...

Fraternity Slut

by oskarwild on Sep 14, 2017
Gay Male

College was great! High school sucked. And Sam was glad to leave it behind. He had been an awkward boy in high school. Short and skinny - only five-six and a hundred ten pounds - and pimply-faced, he had never been able to attract the hot girls that the jocks were able to get. But things began to change when he hit his eighteenth birthday shortly after gradu...

Fun and Games Ch. 06

by jm02201960 on Sep 15, 2017
Gay Male

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it an...

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...

Cadogan Street Carpark

by PicturePainter on Sep 16, 2017
Gay Male

My name is Peter and I am 49 and married but a secret sissy cocksucker. I have a very dirty secret. The feel of women's lingerie against my skin makes my 6 cut cock harder than steel. And it's more than just the cross-dressing. I am bi sexual and I would love to submit to dominant older or younger men. I remember as a child my older sister Janette had the...

Earning Wally an A

by mklit74 on Aug 18, 2017
Gay Male

I realized in college that I was that I was gay, submissive, and that I worshipped my roommate Wally's amazing dick. My relationship with Wally grew over the course of our college career. I would rush home after class to meet him, trying to get home quick enough to change into lingerie, especially a French maid outfit he was particularly fond of, and meet h...

Truck Stop Turn Out

by Ewriter111 on Dec 3, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. *** I was driving home from college for spring break and to celebrate my 19th birthday at home. It was a four hour drive and I got a very late start after having helped my girlfriend and her friends pack their car for Panama City. At midnight, I was still 150 miles away and total...

I Turned Myself Out

by drmweaver705 on Jan 29, 2020
Gay Male

All characters are 18 or over. ***** My journey must have begun with my discovery of porn. When I was eighteen, I discovered a trove of porn magazines hidden out in the abandoned shed of a derelict and condemned house near my childhood home. This was the first time in my sheltered life I had ever seen anything like it. The magazines varied from soft nudit...

Little Sex Toy Ch. 01

by keptsissy on Sep 26, 2017
Gay Male

Rough sex with a big strong man is something I'd always fantasized about. Ever since I can remember masturbating I'd think about being made to do things, dirty things for a man. I thought about being spanked, made to perform for a man, one that wasn't mean but very dominant, somewhat cruel and unusual but not terrifying. I had the fantasy in my head often....

Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...