Transsexuals+&+crossdressers Stories

15,868 results
Orientation
Length
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Infinite Scroll

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

He said "Call me Daddy"

by yvetteinpanties on Sep 12, 2018
Transsexuals & Crossdressers

His personal ad said: dom top daddy seeking submissive, trannies and crossdressers preferred. When I answered his ad as a submissive sissy offering full service as requested, attaching a picture of me in a short camisole and wearing a slave chain between my collar and handcuffs, captioned with "submissive sissy cocksucker can swallow 7 inches. Boi pussy trai...

Fucking Insatiable

by McCrow on Sep 12, 2017
Transsexuals & Crossdressers

((Quick author note: This short story has pretty much zero plot, all smut, so no familiarity with the fantasy setting is required. Have fun!)) * Draenei futanari, as many of us have become intimately aware, are fucking insatiable. For many of the same reasons, they also have a tendency towards entitlement and ego issues. This is hardly surprising, being a...

Gothic Love Ch. 02

by ThomX on Sep 15, 2017
Transsexuals & Crossdressers

#2: Another Story I met him at a drag queen bar called Tranz. Mind you, this was not a bar I would normally have frequented, but I had just gone through a very nasty divorce from my wife of 13 years Melissa, partly becase she discovered my attraction to drag queens, crossdressers, transsexuals, whatever you wish to call them and, believe me, she used that a...

'Jenny' & 'Mike': Date Night

by hfernandez1983 on Sep 25, 2017
Transsexuals & Crossdressers

Hi guys, I hope that you enjoy this story that deals with Pegging and Gender Role Reversal. The idea of pegging has always been a hot topic for me. I have tried it in my personal life, though not in the same way as the characters in this story, and have found it to be a highly erotic experience. I have wanted to write this story for a while but have been put...

Bi Pantyhose Passion

by june613 on Sep 26, 2017
Transsexuals & Crossdressers

I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dressed in Pantyhose for quite a long time. I progressed to "batjack...

Turning into His Toy Ch.01

by vaultdweller111 on Sep 12, 2017
Transsexuals & Crossdressers

So this is the story of how I became daddy's plaything. It all started when I was nineteen and my name was David Romero. I was going through a bit of a depressive stage in my life. My girlfriend left me, I was doing terrible at college, and I hated my retail job. The only safe haven I had was the internet and porn, and let me tell you something there was s...

Crossdressers First Gang Bang

by Erica99 on Sep 12, 2017
Transsexuals & Crossdressers

I stood before the mirror completely satisfied at myself I looked hotter then hell. It was my first time going this far, body fully shaved fake eyelashes professional make up long blonde barbie wig brushed to perfection. Even all my jewelry went perfect with my slutty little outfit I'd bought for the special occasion. Both my matching white lace bra and...

That Sleepover with Sam

by hannah_xox on Jun 19, 2018
Transsexuals & Crossdressers

"How long will you be?" Sam text me, eager to get the first pint down. We had arranged to meet in a pub after work. Our girlfriends were away together for the weekend so we planned some time together. Drinks in the local on Friday night, followed by a walk around London on the Saturday and then a house party on the Saturday night. Sam had to run some errands...

My Life as Lauren Ch. 04

by Lauren_xxx on Sep 13, 2017
Transsexuals & Crossdressers

The shop became quite busy for the next few weeks and we even developed regulars that some of the staff became friends with. A couple of them only went behind the curtain hoping to get lucky but since realising what I wanted I had lessened the amount of blow jobs I gave. There was one guy in particular called mark who went behind the curtain, but mostly stay...