Gay Shemale Mistress Stories

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Infinite Scroll

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

Exploring Sexuality: Cock Sucking

by silkstockingslover on Sep 19, 2017
Gay Male

Summary: Straight guy sucks three strangers' cocks for sister-in-law. Thanks to: Tex Beethoven, Robert, goamz86, Dave and Wayne for editing this story. Although this story can likely be read on its own, reading the first part will probably be useful. But in case it helps, here is a summary of Exploring Sexuality: A Pegging: Ben gets intrigued by the idea...

The Truth

by bjakelow on Aug 18, 2017
Gay Male

There it is... the most beautiful woman I have ever seen. She is just the way I wanted a woman to look when I was a teenager. Giant breast with perfect nipples that just had a way that made me want to suck them. And this is the moment I realized I am no longer that masturbating little teenage boy who just wanted boobs, ass and pussy. It was done. How did thi...

Co-worker's Man Ch. 24

by rmdexter on Sep 14, 2017
Gay Male

As Claudia ascended the stairs and crossed a raised area that overlooked the main foyer, my eyes were glued to her long shapely legs encased in her sheer black stockings. As I mentioned after meeting her in the sex shop, she was a tall women about 5'-10". With her high-heeled sling-back shoes on, she rose to over 6' tall and towered over me. Her round perfec...

My Sweet Bitch Ch. 05

by JasonClearwater on Jul 2, 2018
Gay Male

Author's note: Contains non-consensual/reluctant sex / femdom / BSDM / bondage. Please note, I understand that in the BDSM community consent is paramount, and that is not accurately reflected here in some scenes. Which is, in fact, the whole point. * * * 7.49 a.m. What kind of a time was that to a university student? 7.49 a.m. wasn't supposed to exist for...

Co-worker's Man Ch. 26

by rmdexter on Sep 14, 2017
Gay Male

I had just spent most of the evening with my mouth glued to Mistress Claudia's beautiful pussy and I felt thoroughly soaked with her pussy juice. I couldn't believe that she had sat on my cock and fucked me! She had felt so incredibly hot as the lining of her vagina gripped my pulsing cock. I'm surprised that I lasted the short time that I did! I hoped she'd...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

LoveLocked: WokeWired

by adamlily1972 on Dec 9, 2017
Gay Male

Dear reader: A political satire of "woke" white people, particularly woke white women. Definitely not to everyone's taste. Intended to be humorous. Skip if offended by the notion of a white gal mind-controlling her white boyfriend to service a black dude. But quaff heartily if the idea gets you hot. Adam ********* SCENE 1 [Setting: A spacious but d...

My Tortuous Path to Bi-sexuality

by Cire on Aug 18, 2017
Gay Male

When I was in my mid-20’s, I was sexually molested by two men. Although I was raised during the period of the “sexual revolution”, I didn’t really participate in it. “Things” conspired to keep me out of it. Family financial difficulties made me decide to go out to work at the age of 15 (so that I could buy what I desired) and I undertook to continue my studi...

Becoming a Cock Slave Ch. 03

by John Hamilton on Sep 14, 2017
Gay Male

A fictional fantasy of a bi-curious guy. Chapter 3: The Three-Way I walked into the house and saw my wife at the kitchen table checking her small duffel bag. She was wearing a short, tight one-piece green dress that showed off her figure perfectly. I could see the hard nipples on her large breasts through the dress. I could tell she wasn't wearing a bra. A...