Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Strange Tales of the Deadslayer Ch. 04

by RavynsLand on Nov 4, 2019
Transgender & Crossdressers

"Do you... come here a lot?" I swallow awkwardly, bringing one hand to the back of my powerful, tattooed neck and scratching it, looking away for a moment. Am I seriously gonna be as bad at this as Allara as I was when I was Allan? I thought for sure I'd gotten past this. "Krruya'ta," the girl whispers, and to my surprise, I hear her swallow too. Her lower...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Jack and Jill Pt. 05: Thailand

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab...

Jack and Jill Pt. 04: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

He looked in the mirror, clean shaven with blonde wig and full make up, he was unrecognisable to himself, his false eyelashes fluttered back at him, his shoulders, his hands and his Adam's apple all gave him away on close inspection, but from a distance he was passable as a woman. He couldn't believe he was doing this, he was terrified of going out in public...

And Then It Happened For Real

by DeborahC on Jul 13, 2020
Transgender & Crossdressers

It was the late 90's. I was 19 years old and I knew was developing differently from all the other boys. With hindsight it was obvious, but at that time, not so much. For example, unlike most of my peers who were into Radiohead, REM or Oasis, I had an absolute, devoted love for The Spice Girl and their message of Girl Power. I'd get confused about the unnat...

Maid to be a Housewife

by MakeMeDoBadThings on Jul 14, 2020
Transgender & Crossdressers

I've always known I should've have been born female ever since I could remember. Unfortunately for me I live in a non trans friendly part of the south and never had the courage to openly be myself. I have accumulated a rather large collection of clothes, lingerie, jewelry, shoes and makeup over the years that I loved to dress up in privately. I wanted more b...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Nico's Girlfriend Pt. 04

by SissyDemi99 on Oct 12, 2020
Transgender & Crossdressers

I was ready at 7 am for Jill to pick me up for the first day of school. I wore khaki shorts and was very aware of my smooth legs. I made a sandwich and put it in my bag when I heard the car pull up. I walk outside expecting her to be in the Mercedes she usually drives, but instead she's sitting in the front seat of the red Ferrari with the top down. She loo...

Ems' Dating Tits

by Timjob on Sep 28, 2020
Transgender & Crossdressers

I checked my phone again. She was five minutes late. I sighed but tried to be patient; not all girls are as anal about punctuality as I am. Plus, I suspected, she was a virus girl so she almost certainly had more to worry about than me. I wondered idly which strain she had. The cafe's door chimed, and I looked up. The biggest pair of tits I'd ever seen in...

Kidnapped; Rescued. Ch. 01

by BJGoodhead on Nov 16, 2020
Transgender & Crossdressers

This story is inspired by the single chapter short story "Kidnapped" By LaurenWestley, posted here on Literotica, in the TG/CD forum. Since the original story left the protagonist in such a sorry state, I became motivated to consider a continuation of that story that started out just as dark as the original story but eventually resolved itself with a happy e...