Gay Sissy Maid Stories

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Enticed and Humiliated Ch. 07

by FantasizeAndRealize on Sep 14, 2017
Gay Male

The French Maid in the Sex Shop It was Sunday morning and I rode the metro into downtown Buffalo in order to visit the sex shops. Although I had a hot session with Glen just yesterday I knew that I could not wait too long before I needed to see him again. When I left his apartment the previous day he had told me to purchase a French maid uniform before comi...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...

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...

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,...

Punished Asian Shoplifter Ch. 12

by asianspankee on Sep 19, 2017
Gay Male

After my oral submission to you, I'm left quietly in the corner to reflect on everything that's happened so far till now. Mrs. Jones leaves satisfied, having "conquered" yet another sissy boy with her obscene weapon. After ten minutes you call me back to your side and announces that next week will be my final punishment session. I feel both relieved and sad...

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...

The Long Trip Pt. 02

by TheBlackStallion on Mar 20, 2018
Gay Male

A few weeks went by since my incident in Thailand. Everything felt like a bad dream, but the guys at work didn't bother me at all. No one mentioned a thing, the guys seemed pretty happier than normal but acted like nothing happened. When we pulled into Japan together, Rick insisted we go together. I wasn't going to, but I didn't have anyone else to go with a...

Turning Myself Gay Pt. 04

by bart_allen on Jun 25, 2018
Gay Male

Things changed slowly over the next half a year or so. Work was work, boring and uninteresting, but between that, my consistent aerobic gym work outs and keeping up with Danny took up the majority of my time. We saw each other every week or two, but sometimes he'd go days without texting me. He was definitely a bit of a bro, but he was always friendly and he...