Gay Sissy Bet Stories

4,726 results
Orientation
Length
Source
Infinite Scroll

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

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...

You are a Sissy Pt. 08: Future

by Roland15Rollin on Dec 30, 2019
Gay Male

Hello, sissy. Well, we have come to the end of our journey together, princess. We have explored every corner of your gay sissy mind and now we have come to the end. And what a journey that was. We learned so much, sissy. We learned about who and what you are. We learned about what you want. We learned about what you need. And we finally got rid of all of...

House Rules Ch. 05

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Nine BEYOND THE PINK DOOR For the next hour I explored the sissy wonderland which Daddy had created just for me. It was a bedroom fit for a sissy princess. I guess that was me now, Kitten, Daddy's sissy princess. There was a closet of pretty clothes and shoes. The large dressers were full of so many girly things my head was spinning. There was a...

House Rules Ch. 08

by EROTICbearscribe on Aug 12, 2019
Gay Male

READERS: The story of Kitten is beginning to cross boundaries into other genres. Just as Kitten has changed and evolved, so is his story changing and evolving. ***** Chapter 14 SEDUCED AND SISSIFIED "What's this, let's see. Oh I feel sexy
. What's come over me? Oh, here it comes again. Oh I feel released. Bad times deceased
My confidence has increased. R...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Sissy Cuckold & The Old Bull Ch. 02

by DirtyDaddyHunter on Sep 19, 2017
Gay Male

"Now for your turn" leers the old bull, stroking the mushroomed head of his gnarled old cock. The old man starts to get hard again and grabs the husband's head. He slams his cock back in the husband's mouth, brutally facefucking him. "Is that what you want Sissy? To be Daddies pantied cocksucker? "The husband chokes and gags on this vile old man's big cock,...

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...

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...

Powerhouse Conversions

by AmberFemXD on Aug 18, 2017
Gay Male

Falling flat on my face was not the greatest way to start off the evening but there you have it. I was unpacking taped cardboard boxes in my newly rented apartment. Such a hassle. "How's it going?" Someone had stepped inside. I forgot I had left the front door open. He was a very big man, somewhere around 6'2 wearing all leather. Quite intimidating actuall...