Gay Sissy Wedding Stories

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Job Interview

by BW3 on Aug 18, 2017
Gay Male

We're doing some hiring at my office, and I wish that you applied because I get to do the interviews now. I will lead you back to what I tell you is the office for the interviews. You follow me down the secluded hallway, further and further away from the noise of the office, all the way down to the end. I unlock the door and we enter. It's small and sparse...

How I Became a Sissy Pt. 01

by Yngwhiteboi on Jan 14, 2019
Gay Male

As a young man growing up I knew that I liked both men and women, but never had much success with either due to lack of confidence. Being only 5 foot tall and very small I had never been a hit sexually. To top it all off my shoe size was 5 in the UK. I was a rocker as well, which put off most people, shoulder length brown hair always in a pony tail, ripped j...

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

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...

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...

House Rules Ch. 06

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Eleven WORK TO DO & BUTTERFLY KISSES I fixed breakfast the morning for the both of us. I was wearing pink hipster panties with the word SASSY across the seat and a white cami with pink trim which showed my flat belly. The material was lightweight and tight against my lean torso. You could clearly see my nipples which were as pointy as gumdrops. My...

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,...

Steve's First Gay Sex Ch. 01

by stevemike08066 on Dec 12, 2018
Gay Male

My name is Steve, and I recently turned homosexual, and I now serve a very tough, but fair Master who loves and let's me cum as much as needed. This is the story of how I was not only turned gay, but also submissive. I was having dinner with my girlfriend one night, and we're about to leave when I had to use the men's room. Now to describe myself, I'm 5'...