Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

My First Time CD Sex

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

When I posted my first story, about my most recent experience, I promised to follow up with other stories, including my first time sex as a crossdresser. So here it is. This is the story of my very first time. As I said in my first story, MY stories are totally real, they really happened and happened just as I describe. Nothing at all is made up. I am very l...

Her Bully's College Roommate

by samwalser on Sep 26, 2017
BDSM

Amy was giddy with excitement when her parents dropped her off at the Central University of North Texas. Everything was about to change for her. She'd been teased and bullied all through high-school for her appearance (she's barely five feet tall, skinny, flat-chested (but with big, sensitive nipples, and freckled) and for her general nerdiness—she read a lo...

Open in Reader

Interactive Crossdresser...Dare Me Ch. 04

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

So just to give a small amount of background, besides taking dares from people and performing them, although I don't write about a lot of them, I post ads online using this name, Porsche Karu, seeking men who are looking for a cross-dresser. I get some reply's but they never work out into an encounter. Until one guy, when he first emailed me he was staying...

Crossdresser Gets Found Out

by leathertanya on Sep 16, 2017
Transsexuals & Crossdressers

This story is fiction and is written for my pleasure and any comments or suggestions that anyone would like to make. Any suggestions to the address in my profile. I adore the feel of leather, rubber, pvc and anything silky so it was no surprise to me that at an early age I liked the feel of certain female clothing. I am a perfectly straight male but my fant...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Crossdresser Evolution Ch. 07

by pantyhigh on Dec 9, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - 06 I become addicted to masturbating while wearing panties. There was this part of me that was telling me that I CAN'T like this but there was another part that was saying that I DO like it. I learn about feminized men and I also learn about them sucking cocks and I taste my cum for the first time. I buy my first b...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Super Heroes Ed. 02

by grgy56 on Mar 2, 2020
Transgender & Crossdressers

Super Heroes - Edition 2 There I was. Standing in the front of the full length mirror dressed as Zantanna Zatare - Justice League of America superhero. From the top hat with my long, flowing raven hair cascading down over my more than abundant breast forms barely contained under a tight fitting, frilly blouse and jacket, to the panties that formed my penis...

One of My Favorite One-Offs

by slaveheathen on Nov 27, 2017
Fetish

This is a true story about one of my favorite one-off CL hookups. I had posted an ad, this being back when CL was still actually useful instead of the joke it is today. I mean, seriously, what's with all the time wasters these days? Anyway, I posted the ad; "non-passable crossdresser submissive, I suck cock, eat ass, love getting ass fucked, do ATM, swallo...

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....