Gay Rubber Sissy Stories

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How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

My New Daddy Ch. 03

by sissytoy20 on Mar 6, 2018
Gay Male

The buttplug that Sam had unceremoniously forced inside my tight asscunt had hurt like hell, but I'd enjoyed the feeling of being forced open with no warning. The little, pink butt plug wasn't very large, but it had felt like a giant donkey dick in my ass. It had flashed by in Sam's hand so quickly, maybe it was larger than I thought. It felt huge in my butt...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

The Hanky Code Pt. 15

by His_fag_wife on Sep 14, 2017
Gay Male

Mistress Caprice stood in front of me and looked deep into my glazed eyes, as I rocked up and down on my rubber cock. "I had to pay a pretty penny for you bitch, after so many people had watched some of your more extreme videos. A lot of very depraved people could see just how much use you might be." "But I wanted you before your inevitable trip to the far...

Sissy Bottom Has a Nite Out Ch. 02

by lostsoul1974 on Sep 14, 2017
Gay Male

Last night, my friend Eric and I had some really hot sex down at the Adult Theatre. Eric had me wear a pair of my wife's panties and I was a sissy fuck-boy for a whole theatre full of horny men. My wife is out of town for the weekend, so we are gonna be as lecherous as two bisexual fuck-buddies can be. This morning, I awoke to the sensation of Eric's hand s...

The Hanky Code Pt. 16

by His_fag_wife on Sep 14, 2017
Gay Male

Melinda opened the door to a very large guy, not tall but fat almost round. He waddled in smiling and sweating profusely. He carried a large Gladstone bag giving him the air of an old fashioned Doctor. Mistress Caprice said "Welcome Mr Smotherer, I hope you're pleased with your pig." "Ohhhhh yes, she looks perfect, I really have worked up a sweat on the wa...

Fun and Games Ch. 06

by jm02201960 on Sep 15, 2017
Gay Male

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it an...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

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...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...