Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Finding the Perfect Fit Pt. 03

by Joshana on Oct 8, 2019
Transgender & Crossdressers

An Awesome Day It took too long for Jamie and I to hang out again but we kept talking the whole time, me working when I could. If I asked what he was wearing, I'd get a picture of a bra strap peeking out from under a shirt, the black comfy one proving to be the most popular. But the peach T-shirt bra got some use too, more often during the weekend. "It's s...

Neighbourhood Terror to Sissy Pt. 13

by Fibaro on Oct 7, 2019
Transgender & Crossdressers

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...

Tablake Pt. 01

by giandomenico on Sep 23, 2019
Transgender & Crossdressers

On the surface I was a successful man working in a profession I enjoyed, earning as much money as any sensible man needs. I lived in London, one of the most exciting cities on earth. I had a pleasant house. I was thirty-five, five feet ten inches tall, slightly built but not at all bad looking. I knew that some of my colleagues envied me my success and my li...

Email to My TV Mistress

by BobbyFingers on Sep 24, 2019
Transgender & Crossdressers

You text me demanding I visit within the hour. It is clear from the tone of your texts that you are not happy and I wonder if it's something I have done. Luckily I am available so I text back, agree a time and get cleaned and ready and make my way over. You had already texted me with your order, to undress until I had a shirt and underpants on and to go to t...

The Trade Show Pt. 08: Boobs First

by GeorgiaD on Oct 7, 2019
Transgender & Crossdressers

I welcome feedback so please, if you would like to comment, feel free. Be kind though! ***** As I rode Cindy's shaft, enjoying varying my position to both enhance her and my own feelings, my mind drifted, dreaming of what lay ahead for Georgia, and how I would handle transitioning at work. Immediately, of course, doubts crept in and I was jolted back to r...

Finding the Perfect Fit Pt. 05

by Joshana on Oct 22, 2019
Transgender & Crossdressers

Finally I bolted awake Saturday morning, instantly knowing what I had to do. It was like Christmas morning when I was a kid, with endless potential dancing in the air and anything was possible. But it was on me now to make it happen. Rolling out of bed, I looked out the window and paused, seeing the light dusting of white over the campus grounds. Sure, it w...

Honeymoon in Heaven

by deweyflower11709 on Dec 9, 2019
Transgender & Crossdressers

I recommend you read my series "Mother in Law to Lover in Law" first to find out how these two became newlyweds. I awoke in the grey dawn, confused by the sensations that were engulfing me. After a couple of moments it slowly came back to me. I was lying in my bed, wearing my new red silk night dress. Heather Ann, my new wife and ex-mother-in-law, was cuddl...

Watching Paige's Back

by S_Hollister on Dec 3, 2019
Transgender & Crossdressers

Melanie swore as her phone started buzzing, putting out the cigarette she had been enjoying and kicking its remains down a neary grate as she pulled out the device that had interrupted what had been a pleasant break. Still, 14:50, mustn't be late... She got into the driver's seat of the sleek electric car she had been leaning against. It came to life with a...

Jerri! Naked!

by TxSmutWriter on Dec 3, 2019
Transgender & Crossdressers

Note: I intended for this to be a stand-alone story, but see how it could easily continue. If you have any ideas on where this should go, feel free to message me! * When I was growing up, I had a huge crush on my neighbor, Jerri Jergens. She was exquisite, simply the ultimate in beauty and femininity to me. I used every excuse to watch her, even when her h...

Neighbourhood Terror to Sissy Pt. 15

by Fibaro on Dec 23, 2019
Transgender & Crossdressers

Chapter 17 "If you don't mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don't trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great." Linda said to Lisa who was still getting her feet wors...