Alpha Fucks Crossdresser First Time Stories Stories

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Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

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...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

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...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Man in the Mask

by MiOtroYo on Sep 16, 2017
Transsexuals & Crossdressers

Mel was sitting on the corner of the cheap hotel king-size bed. Aroused, nervous, simply scared by the whole story, he still wanted it to happen. Once a lifetime dream, now a striking reality -- it was all here, from the remote sound of the cars passing by to that filthy, nasty smell of the motel building... "Hi, my name is Melinda. I am a young closet cros...

Michele Nylons' True Stories Ch. 03

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures. In the next two instalments I will tell you about some of my encounters that were not particularly satisfactory. As most closet Transvestites will know, there are a lot of losers out there and some of them can even be a little scary. * Story One - The R...

The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...