Gay Sissy Stories

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Orientation
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The Molly Virus Ch. 03

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

*Jeri... I still got a few looks as I came in from the cab and to my room. Word seemed to have spread a little about me and my transition. The few looks I got were more dumbfounded and not getting it instead of like hateful and I'm pretty sure there were eyes on my ass as I went up the stairs to my room. Jack's there listening to music on his headphones lo...

A Mistress to Obey Ch. 04

by gbr2004 on Sep 12, 2017
BDSM

This story includes female domination, forced fem, forced bi and discipline. Not your thing, please find a different story. I follow Mistress into the playroom wearing just the thigh high nylons and heels. I'm so hoping she is in a good mood after watching her have several orgasms with Terrell. Maybe she will be in a more playful mood, hopefully, thinki...

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...

Neighbourhood Sissy

by Abusedbyfuta on Feb 7, 2019
Fetish

Your a young man in his late teens. Average build, average height, brown hair, green eyes. You know the type never stood out in a crowd for your good looks but never scared children when you went to the store either. Having just finished high school ou decide to start doing odd jobs around the neighbourhood to raise some money. Maybe it was college, maybe it...

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Sissy Bitch Ch. 01

by sissy_memories on Sep 12, 2017
Transsexuals & Crossdressers

After I moved out of my parent's house, I found an apartment with my a girl called Laura. I was nineteen, she was eighteen and, as one of the few left in town after everyone we knew took off for college, we had little choice for room mates. I didn't even know Laura that well: we had mutual friends and that was about it (though I did know she was good fun aft...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Cock Sucking Jail Whore

by RobinTVDaniels on Sep 15, 2017
Transsexuals & Crossdressers

I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with big hard dicks and women on their knees about to suck or be...

Are You a Sissy?

by dominantdadddy on Sep 26, 2017
Transsexuals & Crossdressers

There I was, early Friday evening, standing on the front steps of my co-worker, Liam's house. As instructed, I brought with me a small overnight bag with the following items: a toothbrush, toothpaste, razor, shaving foam, and flip flops. I was nervous. I was not sure what was in store for me. But I had an idea. On Tuesday, Liam had called me into his off...

Getting Help Ch. 01

by azkelkel on Sep 16, 2017
Transsexuals & Crossdressers

I nervously sat in the waiting room for my 1:00 p.m. appointment with the therapist/psychologist. I found her through online searches, as I guess we do all things nowadays, where her credentials and location were most important to me. She received her various degrees from decent universities and chose to open up her practice in an area just far enough away f...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...