Crossdressers Stories

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The Woman Next Door Pt. 01: We Begin

by jableabee on Mar 9, 2020
Transgender & Crossdressers

Do not ever doubt that your life can change in a moment. Mine did. And oh so much for the better. All it took was a knock on the door. On Saturday mornings I take care of my chores: some cleaning, the laundry, shopping, the usual tasks. I'm generally done by noon and then it's time to transform myself into "Barbara", my feminine self. I'll shower, shave, do...

He said "Call me Daddy"

by yvetteinpanties on Sep 12, 2018
Transsexuals & Crossdressers

His personal ad said: dom top daddy seeking submissive, trannies and crossdressers preferred. When I answered his ad as a submissive sissy offering full service as requested, attaching a picture of me in a short camisole and wearing a slave chain between my collar and handcuffs, captioned with "submissive sissy cocksucker can swallow 7 inches. Boi pussy trai...

Bi Pantyhose Passion

by june613 on Sep 26, 2017
Transsexuals & Crossdressers

I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dressed in Pantyhose for quite a long time. I progressed to "batjack...

That Sleepover with Sam

by hannah_xox on Jun 19, 2018
Transsexuals & Crossdressers

"How long will you be?" Sam text me, eager to get the first pint down. We had arranged to meet in a pub after work. Our girlfriends were away together for the weekend so we planned some time together. Drinks in the local on Friday night, followed by a walk around London on the Saturday and then a house party on the Saturday night. Sam had to run some errands...

My Life as Lauren Ch. 04

by Lauren_xxx on Sep 13, 2017
Transsexuals & Crossdressers

The shop became quite busy for the next few weeks and we even developed regulars that some of the staff became friends with. A couple of them only went behind the curtain hoping to get lucky but since realising what I wanted I had lessened the amount of blow jobs I gave. There was one guy in particular called mark who went behind the curtain, but mostly stay...

My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....

Turning into His Toy Ch.01

by vaultdweller111 on Sep 12, 2017
Transsexuals & Crossdressers

So this is the story of how I became daddy's plaything. It all started when I was nineteen and my name was David Romero. I was going through a bit of a depressive stage in my life. My girlfriend left me, I was doing terrible at college, and I hated my retail job. The only safe haven I had was the internet and porn, and let me tell you something there was s...

Crossdressers First Gang Bang

by Erica99 on Sep 12, 2017
Transsexuals & Crossdressers

I stood before the mirror completely satisfied at myself I looked hotter then hell. It was my first time going this far, body fully shaved fake eyelashes professional make up long blonde barbie wig brushed to perfection. Even all my jewelry went perfect with my slutty little outfit I'd bought for the special occasion. Both my matching white lace bra and...

Crossdressing Friends

by kinkyrubber on Sep 12, 2017
Transsexuals & Crossdressers

In the three years that I have lived in an apartment with my friend Joe, I've never thought of him in a sexual way. Recently, I discovered that he is a crossdresser like me. We both just hide it. I was looking in his room for one of my dvd's he borrowed and found wigs, women's clothes and even a Polaroid of him dressed as a woman. The moment my eyes glanced...

A Wife's Surprise

by Aprilsdays on Jul 3, 2019
Transgender & Crossdressers

April's Amazing Day So, my story starts like most of us crossdressers, finding moms lingerie in the clothes hamper as a pre-teen and of course putting things on while getting those first feelings of excitement, sexiness, and that surge of adrenaline. Every day I became consumed with hoping against hope that when I arrived home, no one would be around so tha...