Shemale Sissy Stories

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Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

The Trade: Hooks

by jdjangles on Sep 16, 2017
Transsexuals & Crossdressers

"Pink. It suits you better," I said. I had been eyeing the kid for a while now, he wasn't very stealthy. He'd been examining panties for the past ten minutes. "Oh, these aren't for me. They're for my girlfriend." He said, the nervous giggle did him in, there was no girlfriend. Not today, at least. "She have the same hips and ass that you have?" I asked, hi...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

One Piece Foot Journey

by sofly on Apr 25, 2015
Fetish

Your eyes, wincing as you look out into the distance sea as the sun reflects of its surface, "Is that them?" you think too yourself. In the distance you can see a small outline of what looks like a ship. Everyone too has spotted this in the distance as you hear a huge uproar behind you. "Its them!, the Straw Hats are coming" the screams b...

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Black Girls Have Big Dicks

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

She was like no woman I had ever seen before. She walked into a room and everyone's eyes were on her. She just had that incredible presence that just lit up the room and everyone just wanted to be around her. I was working behind the bar of a trendy club when I first saw her saunter in on her long legs, swaying her hips in a short dress. She walked over to t...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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Die Mädchenschule für Jungen

by Redboom on Feb 12, 2020
Transsexual

In einem kleinen Café: Verträumt blick Leon in den großen Spiegel auf der anderen Seite des Raumes. Das Spiegelbild zeigt zwei Damen in den Enddreißigern, eine junge Dame Anfang zwanzig und ein hübsches Mädchen gerade achtzehn Jahre alt geworden. Zumindest sieht sie aus wie ein hübsches Mädchen: Eng anliegendes dunkelblaues Chiffonkleid mit locker über die S...

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Locked down in a lockdown

by MrTwister5 on Oct 19, 2020
Fetish

Being a junior software developer, you were one of the first to be sent home when the first signs of the pandemic came up. While you thought that it’d be fun to hang out at the house while everyone else was at work, it soon became evident that everyone else would follow suite. By the end of the next two weeks, all five of you were working from home. At first...

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