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Cross Dressing Stories

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification.

Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender.

The crossdresser can be of any sexual orientation.

Popular Stories

SissyMandy - Insatiable Little Me

I had no idea last night was only a prelude to what's in store for me tonight

It's hard to believe I'm waking up so energetic after my guys pounded the hell out of me last night. The more they gave me, the more I wanted, and I might have gone all night if their cocks could have stayed hard. I'm not sure what time we finally crawled...

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My Air BNB Experience Part 2

Things get a little more heated at the Cabin.

I got ready at 1 and ensured I was clean and prepared for this afternoon’s adventure; I put on a cute white and blue matching lace bra and pantie set and a green summer dress with heeled boots. I waited patiently till bang on 2 when I heard the quad bike...

SissyMandy - Flying Home To Mistress

Mistress unveils a special surprise upon my return from my weekend in Carmel

I wish Rob wasn't taking me to the airport to catch my flight home after my fantastic weekend in Carmel. I'll miss the almost non-stop sex, and I'll never forget the incredible sex party they gave me last night that was simply out of this world. It was so...

Chrissie Chapter 4

Chrissie makes a deeper committment

My masters had wanted me to get an early start Saturday morning, so by 9:30am I was already in my maid’s uniform scrubbing the hallway baseboards while Rebecca and Karl relaxed in bed smoking a wake-up joint and watching cartoons. From my kneeling positio...

SissyMandy - Insatiable Little Me

I had no idea last night was only a prelude to what's in store for me tonight

It's hard to believe I'm waking up so energetic after my guys pounded the hell out of me last night. The more they gave me, the more I wanted, and I might have gone all night if their cocks could have stayed hard. I'm not sure what time we finally crawled...

Waxing – Really?

Oh, Learning the Things a Woman Does

We have been home several months after our summer-long RV trip. I am femme all the time and have so much fun learning and experiencing things associated with being accepted as a woman. Upon returning home in the early afternoon after working at the office...

Chrissie, Chapter 3

The submissive crossdresser falls deeper down the rabbit hole of submission

Wednesday’s cleaning shift took a lecherous twist and my Rebecca Anne Martin obsession boiled over into full-blown delirium. Since the schedule called for light house cleaning on Mondays and Wednesdays after work, I normally would have waited until the we...

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Chrissie, Chapter 2

A submissive crossdresser serves his ex-girlfriend and her hubby

Rebecca’s text triggered the panic button, and in my haste to get ready I stubbed my toe on the bathtub. Ignoring the pain, I focused on my mission: “house needs clean.” Because it was a Saturday and I wasn’t worried about concealing a lumpy garment benea...

Becoming Anne - My Feminization Chapter 3

My wife discovers my need to be feminized and begins my makeover to Anne (series)

Jess took a few steps back to consider the answer to her question. As she did I was reminded of just how strongly I was attracted to her. My beautiful wife stood 5’6 and weighed 145lbs. Fair skin perfectly molded to her curvaceous figure. Generous D-cup b...

Sissy Riley: The Dream Of Las Vegas. PT 1. Gooning, Sucking And Cumming

The Start of Sissy Riley's Journey to Las Vegas!

John had finally done it. He had started an online self-sustaining store that would help him quit his 9-5 job. He was only a few weeks away. This store would help John focus on something he had always wanted to give time and effort to, becoming a Sissy. J...

Caught!

Getting caught was his worst nightmare, or was it?

I’d been looking forward to the long holiday weekend for a while. Christa, my girlfriend, was going away on a girl’s trip, allowing me three days of uninterrupted alone time. Don’t get me wrong, I loved Christa and enjoyed our time together but, there wer...

Becoming Anne - My Feminization Chapter 2

I revisit the beginnings of my cravings to become feminized

"Newly discovered persona,” she said. Jess’s choice of words was never accidental. This previously concealed aspect of my character was now on full display. I was not playing a role, this was not contrived, this was me, an emerging new identity. So there...

SissyMandy - Game Changer

I expected an exciting weekend, but I didn't know just how exciting it would be

It's been a while since I've been with a man, and never by myself for an entire night, except for with Rob. So it's no wonder I'm in a sissy daze as we're holding hands during the thirty-minute drive from the Monterey airport to his home in Carmel. I've b...