Crossdressers Stories

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Infinite Scroll

Brooke Opens Up

by EnjoyBoth on Oct 6, 2020
Transgender & Crossdressers

The end of spring was making its way into Pennsylvania with summer knocking on the door and I got to enjoy the drive from Pittsburgh to Hershey for a work conference. You know the ones where they stress three days of leadership and team building. This year, the company picked a five-star hotel with its beautiful venue, attractions, and small cottages. It was...

Work Out Curtain Up

by bigthrow on Oct 13, 2020
Transgender & Crossdressers

Black, absolutely, oppressively black. I can't see anything, anything at all. Just an endless sea of black stretching out into the infinite void ahead of me. It hurts my eyes, stinging and biting, but I can't look away. Everywhere is black, as vast, as wide, as all-consuming as the crush of the heavens above. I can't hear anything. The ringing in my ears wo...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

Walk a Crooked Milf Ch. 02

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter Two - Don't Be a Sissy! "I'm not sure I like you referring to me as a MILF," Mrs Cashmore said. I had counted the hours until I was back in Mrs Cashmore's house. Much to my mother's regret I had not elected to go on to university and had taken a job in a hardware store to help my mother pay the bills. I had told her that I intended to continue my e...

True Love Ch. 06

by das4200 on Sep 25, 2017
Transsexuals & Crossdressers

-14- The rest of the night with Sam was spent planning out our business adventure. We spent an hour or so researching how to go about even starting a porn website. We both knew from our limited experience that when you signed up for a site you would go through a billing service. So we figured that the service would take a percentage for their part and offer...

Becoming Cassie Ch. 05

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

The Halloween weekend was rushing towards me. All my life I had these wonderful fantasies of going out for Halloween dressed. While I might not actually go out, I knew that this year was going to be different. Something exciting was going to happen at the Warrens, and that kept me guessing all week long. So when my mom dropped me off to the Warrens on the...

Miss Jennifer's Sissy Housewife

by tiffanyfoxe on Sep 19, 2017
Transsexuals & Crossdressers

My job was much less demanding than my wife's, so she had always "suggested" that I do all the housecleaning, shopping and cooking all week, and of course I never minded because I secretly loved being subservient to her. She loved to tease me when we'd be out somewhere together and she'd see a good looking guy by telling me how attractive she thought he was...

How I Became a Cheerleader Ch. 14

by DMaster_14 on Sep 25, 2017
Transsexuals & Crossdressers

The morning after graduation, I dressed in mini skirt, thong panties, and a white tank top with "Pink" on it, put my hair back in a clip, loaded my suitcase and some of my personal stuff into my new car and headed over to Trent's. He was leaving that morning on a two week business trip with Jason and I had to formally say goodbye. He and I had said goodbye t...

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

The Barbeque

by dysfunctionaldreams on Sep 12, 2017
Transsexuals & Crossdressers

It was your typical Saturday. A bunch of us had decided on a barbeque at our friend Jerry's house. Jerry had the best backyard you see, ample room for a big knee-high card table that we used for drinking games and a beer pong table next to that. All in all, there were about ten people that came over for the afternoon. The group consisted of four girls and s...