Gay Hairless Sissy Stories

2,946 results
Orientation
Length
Source
Infinite Scroll

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...

Wife and I Get a Roommate Ch. 01

by tonyl65 on Sep 25, 2017
Gay Male

It was the early 80s; I was taking a full load in college and working full time. At nineteen I was making good money, going to school, and just married my high school sweetheart. I know it was too young, but it was 80's and I thought the only way out of my parent's house was to get married. We were married for a year now and, at twenty, we had a nice two bed...

Fat Bottomed Girl Pt. 05

by eviltwin52 on Jun 4, 2019
Gay Male

It's gotten to the point that I'm chained to my obsession to a fat bottomed girl. I've allowed myself to be molded into that mate Sheila wanted. I mean before Sheila I was a woman chaser. A woman with a big ass fascinated me, aroused me, and now I'm a slave to my fetish. Sheila dominates every aspect of my life. Me queering off for her is just another way fo...

Cream Puff Ch. 02

by RubixStu on Mar 12, 2019
Gay Male

When I woke Sunday morning, I was completely nude. I'd showered and removed my makeup before bed. The image in the mirror as I pissed standing up was totally male. I was clearly a man, in appearance at least. Sure, I was totally hairless, but that didn't make me less male. Inside I didn't feel manly. I didn't feel independent, willful, or strong. I felt vu...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

Party Pizzazz Ch. 02

by bjmichaels on Oct 6, 2020
Gay Male

Party Pizzazz Ch. 02 by BJ Michaels If Tommy hadn't kept such a close eye on me all night at the party I would've ended up as a boy-toy for one of those rich men. That's what he told me afterwards in the car on the drive to his apartment. "Lucky for you I happened to overhear those five assholes bidding on you or you'd belong to one of them now," he said...

Coming to Terms

by HerLittlePiggy on Aug 18, 2017
Gay Male

I stood naked beside the bed. My hard cock jutted straight out from my body betraying my excitement. "I have never done this before," I said softly. "But it excites you doesn't it?" "I guess so," I answered as my cheeks flushed red with embarrassment. "You guess so? It's a yes or no question. Does it excite you?" "Yes," I replied honestly as I cast m...

Greek Delight Ch. 02

by S_Queen on Sep 25, 2017
Gay Male

When I woke it was morning and I was erect. The sun was up, and I could tell it was hot. Looking over, I saw a slender, feminine body lying naked on its front, face away from me. The back curved into the most delicious ass, round and peachy. I reached out and touched the bottom, the soft skin like marble to my fingertips. I gently squeezed the firm buttocks...

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...

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...