Gay Shaving Sissy Stories

1,448 results
Orientation
Length
Source
Infinite Scroll

My New Daddy Ch. 01

by sissytoy20 on Feb 13, 2018
Gay Male

I'm 21 years old and I attend college but I still live at home for financial reasons. I've always been fem and young-looking for my age. I like to cross dress, but I don't usually dress fem in public. I've just found that it can be difficult for some straight folks to take a young male who likes to be a sissy slut. So you can imagine my surprise when I was r...

This Thing Called Life

by noodneighbor on Sep 14, 2017
Gay Male

I had it all figured out this thing called life, or so I thought. Turns out life can kick you in the balls when you're not looking and turn your whole world around. I'm a jock, sorry, was a jock; I guess once you graduate high school unless you go pro or get a scholarship you're not technically a jock anymore. I still run and lead an active life though and t...

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...

I Turned Myself Out Ch. 04

by drmweaver705 on Sep 14, 2020
Gay Male

All characters are over 18. This story contains bisexual and cuckolding activity as well as fetishistic name-calling. If you don't enjoy these things, this might not be the story for you. *** Porn seduced me early in life and, even as a married man, it commands part of my loyalty to this day. It happened that I became bored, or maybe just desensitized, to...

Danny Darling Ch. 05

by bjmichaels on Sep 14, 2017
Gay Male

"UNBUTTON YOUR SHIRT AND OPEN YOUR SLACKS, YOU LITTLE WORM!!" she screamed in my ear. I stood there stunned; frozen in place. I couldn't believe the abrupt change in Mrs. Nelson's demeanor. The normally sweet, good-natured woman had never made even the slightest derogatory comment to me, and she certainly never raised her voice when she reprimanded me for...

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...

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...

How I Became a Sissy Pt. 02

by Yngwhiteboi on Jan 16, 2019
Gay Male

I wake startled and suddenly remember where I am. I feel the weight of Abduls arm on my waist. I gently pick up his arm and lay it next to me. He rolls on to his back, now snoring. My asshole is sore and I have an incredible urge to empty. I slip out the bed, look at the clock, it's only 0530. I creep to the bathroom and close the door. I turn the light on,...

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...

Research

by eviltwin52 on Aug 18, 2017
Gay Male

This story is dedicated to Kept Sissy who was so instrumental in helping me understand my urges. I was in the final phase of getting my Doctorate in psychology. My dissertation was to be on the difference between transgender boys, homosexuals, and sissies. You see, the transgender feels as though they were born with the wrong physical sex organs whereas i...