Sissy Black Stories

190,488 results
Orientation
Length
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Infinite Scroll

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

Sissy Life

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here.... I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, s...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...

A Week End with Mistress Pt. 02

by gasissynora on Oct 30, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** I arrive at Mistress Nikki''s a couple of minutes before 2:0...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...