Transsexuals & Crossdressers Stories

12,315 results
Orientation
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Infinite Scroll

Black Transsexuals

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Whenever I'm off duty, I'm liable to get into some type of adventure. Who am I? I am Troy Shane, a sergeant with the Massachusetts State Police. I was walking around the Boston Public Library when I saw this tall, plump jet-black honey with a big butt. She was walking around strutting her stuff. A Black chick with a pretty face, thick body and a fat ass. Def...

Female Seduces a Shemale

by Tashas Baby on Sep 25, 2017
Transsexuals & Crossdressers

* This story may not be copied or reproduced in any way. This is a story I wrote for my lover.* As you are sitting in your computer chair , chatting online, I walk up behind you and softly massage your arms. I lean around and kiss you on the cheek. You turn your head to see who it is and I kiss you full on the lips. I walk around your chair and sit on your...

A Slut Is Born

by caroletv31 on Sep 16, 2017
Transsexuals & Crossdressers

I've always had a magnetic attraction to slender pointy hi-heel stilettos since way back when. And then these wonderful sensual sexy feelings between my thighs every time I see a young lady strutting and teetering around on these fabulously erotic pointy heels. It all started in the 1950s era. The era "par excellence" for these gorgeous shoes that did so muc...

The Tasting

by IraIrene on Sep 16, 2017
Transsexuals & Crossdressers

"Mmm. You're pretty in frills, sissy. Pink polka dots look good on you, and your lipstick is just so. Lift up your skirt for me, show me the panties you picked out." "Aww, those are too small. Your cock is poking out. Hee! Now turn around and wiggle your cute little tush for me. Good sissy boy. Now get down on your knees." "I suppose you're wondering why w...

A Fantasy

by Sittingwiththedevil189 on Dec 16, 2017
Transsexuals & Crossdressers

I want somebody to worship me, maybe with love or lust. I mainly want the lust right now. This person would wanna kiss me from head to toe and want to please me over and over again. The person would want to savor me; taste me in their mouth for day's to come. I want them to want me so badly they would do just about anything for me to be satisfied. I'd call...

Discovery by Disguise

by jenniferjoannarose on Mar 14, 2018
Transsexuals & Crossdressers

He bent me over and fucked me with a vicious hunger. This was my very first time. This gorgeous hunk of man was popping my gay cherry. He was so big, so very big, that I was afraid he was going to break my ass. I was hurting, but I was nowhere near wanting him to stop. He was bigger than the largest butt plug I had using to train my ass for just a moment as...

Abandoned Parking Lot Pt. 01

by sissyscarlet on May 16, 2018
Transsexuals & Crossdressers

It begins... Well, I found out that Anne fucked that professor again. She came to my dorm drunk at 3am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won't even get started on what she was on about. I tried calming her down, but whenever I said anything she just slapped me, or if I tried to stop her from drinking m...

My Fantastic Transformation

by Crimson_Spectre on Jul 31, 2018
Transsexuals & Crossdressers

My dream starts with me in a strange dressing room. Before me are a lovely pair of boots. They are lavender, with simple heels. They are only at ankle height. Seeing no one around, I decide these boots must be for me. I slip my feet inside and they are like a second skin around my feet. Heels were not made to be this comfortable, and yet they feel like they...

When the Balls Drop; A New Years Tale Ch. 08

by LuciousBi-Writes4U on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight- A Night on the Town… While the two lay their sprawled on the couch trying to recuperate Veronica asked, "Now what will happen when next week comes, and your world goes back to normal?" In a half mocking question so she wouldn't sound too serious. "What do you mean—we'll date just like everyone else does …" Mason replied. "You won't be asha...

When the Balls Drop; A New Years Tale Ch. 03

by LuciousBi-Writes4U on Sep 16, 2017
Transsexuals & Crossdressers

As they chatted Veronica wiggled her hand over to Mason's leg. She began to stroke his thigh as they talked and drove. Before he knew it Veronica had worked her hand up under his seat belt and begun rubbing the front of his slacks. Mason quickly struggled out of his seat belt to allow her full access. "Mmm, A big boy too aren't you," Veronica giggled as sh...