Halloween Crossdressing Stories

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Selective Fetishism

by Magnolia13 on Sep 16, 2017
Reviews & Essays

Is it possible to have “selective fetishism”? What I mean is that sometimes in some circumstances I find myself irresistibly drawn to one thing or another that could become a fetish if I were to find it appealing all the time. The word ‘fetish’ doesn’t really fit as it implies a desire that is permanent and always necessary for arousal. I find some things...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

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...

The Birth of Whore Mouth

by KnobGoblin001 on Mar 10, 2020
Transgender & Crossdressers

In 1998, Halloween landed on a Saturday night. I was 32 years old, which means I had already been sober for over 5 years. That said, I can neither blame alcohol, nor reckless youth for what transpired that night. My band Mistress was scheduled to play that night at a private club. A typical off-road, VFW, or Union Hall, or Water Buffalo Lodge type venue. W...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

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...

Halloween: A Pussycat's Tail

by meowjennie on Oct 26, 2020
Transgender & Crossdressers

The Literotica Annual Halloween Story Contest is on! Read the scary sexy stories (new ones daily!) and submit your tale of terror for fame, fun, and a chance at cash prizes!" I smiled wistfully as I read the announcement on my computer screen. While I loved erotic stories almost as much as I loved writing, the unfortunate reality was that I lacked the talen...

Girls Night Out With Wife Ch. 01

by Vanessa_tgirl on Sep 12, 2017
Transsexuals & Crossdressers

I have always enjoyed crossdressing. I remember dressing as a female for halloween when I was younger and would get so turned on. One night while lying in bed with my wife Cindy, she placed her silk panties on my cock. She noticed how excited I got and asked me if I liked it. She then asked me to put them on. I was really turned on and so was she. I then men...

Poppets

by surrealmod on Oct 19, 2017
Fantasy

The Players Introduced The house, such as it remains, is now quite far from the reach of any but the most determined. Those who made it their home are now dispersed throughout the world. Should you meet them, in bars or restaurants, or even walking down the streets of their new suburban climes, they will invariably deny the events I am about to relate. You m...

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Kasey's Confession Ch. 15

by KaseyLegs on Sep 12, 2017
Transsexuals & Crossdressers

Dr. Duckworth, who looked just like the crazy shrink Gary I'd met while apparently imagining myself as a prostitute, had apparently been consulting with Dr. Bennett and others during my coma. He was very interested in the psychological effects that being in a comatose state for an extended period of time had on a person. When he informed me that he was willi...