Gay Sissy Strapon Stories

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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...

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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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...

Escape Room for Jocks Pt. 04

by MrSunshineBoy on Sep 28, 2020
Gay Male

Mike and Tristan kissed each other before they ended the message on the microphone. They looked at the TV screen at the 4 guys in the 2 different rooms that prepared to leave for the next tasks. "This was a fun introduction to our game." Mike chuckled, recalling the hot make-out sessions between the guys. "Let's just hope they stay just as horny as they we...

Admitting My Secret Ch. 01

by HerLittlePiggy on Oct 22, 2019
Gay Male

I heard the door open but the sound of foot steps was muted by the thick carpet covering the floor. I was hogtied and blindfolded on the floor of our apartment. It was a game Julie and I had played numerous times. She was my Domme and I was her slave, her pet and her filthy little piggy. Julie was my beautiful 30 year old bride and I was her 38 husband. Sh...

My First Time Giving Oral

by MrJimJim on Sep 15, 2017
Gay Male

Through my tears I watched the neon of the bar get brighter. She had left me, for good this time... All my attention had been focused on other things, including porn, and everything but her. I'm not angry with her, but with myself. That's why a few tequila shots will make me forget... This was the alcoholic amnesia, the whole place filled with men who want...

Teaming Up to Turn Them Out

by vikkihawe000 on Oct 8, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sexual situations. * After Kelly graduated from college, she desperately wanted to move to the city, but her mother was hesitant to send her only child to the big city even if she was 23. However, she finally relented after Kelly suggested she live with her Uncle Rod and his long term...

My Journey into Bisexuality Ch. 01

by kinkymmale on Aug 18, 2017
Gay Male

This is a story about my first bisexual experience, but before I get into the details of what happened, let me explain myself a little bit first: I am a 26 year old married man that has been married to a beautiful wife for 3 years. Our sex life has been incredible! I have always wondered what it feels like sexually from the woman's perspective since I first...

My Neighbor the Cop Ch. 02

by tonyl65 on Sep 25, 2017
Gay Male

I found myself walking across the street from my neighbor's house with the taste of cum in my mouth. I walked into my house, not my house, but my wife and I's house. I was married, my wife is out of town for the weekend, and after helping my neighbor with some yard work I end up sucking his cock and being his pussy boy. What got into me, other than my neighb...

Progression Ch. 09: Punishment

by klapperz on May 1, 2018
Gay Male

Once again Nathan found himself lying awake beside Kevin, who was sound asleep. All that was running through Nathan's mind was having Kevin's cock thrust into his ass. Unable to sleep, Nathan sat up and turned on his laptop to watch some porn. He logged into Ryan and Jacks porn channel and watched the videos. Each one made his cock fill the cage more each t...