Halloween Crossdressing Stories

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Halloween Problems

by Haley_Hazel on Oct 22, 2019
Fetish

Your not that old... So it makes sense you'd want to celebrate Halloween still as an adult. The thing is, you don't care about candy, and costumes, and spooky stuff. Nope, not you. YOUR into this holiday for the skimpy outfits, and parties... for the easy woman at those parties who are even better than candy! So as you walk downtown ignoring the kids in thei...

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Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

It All Started When...

by crashmatt on Oct 24, 2018
Transgender & Crossdressers

It all started when... well, perhaps that's not a great way to start. It's difficult to say exactly when it started, or perhaps even what "it" is. For the purposes of this story "it" relates to an episode at Halloween, yes I know, another Halloween story. But, you see, in the UK Halloween isn't the event that it is in the USA, and crossdressing for Halloween...

Caught For the Last Time Ch. 07

by TGJamie on Sep 15, 2017
Transsexuals & Crossdressers

We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top. "That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head. Th...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Eric's Dreams Pt. 03

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

Eric kept thinking about his sex problem. He was a crossdresser. But most gay men didn't like that. The sex, yes, but not the crossdressing. Gay men, at least most gay men, had no interest in lipstick and lingerie, and the thrill of passing as a woman. They wanted to fuck and be fucked by men. They wanted to have their cocks sucked by men. And they wanted to...

Crossing over

by twizted77 on Nov 14, 2019
Transsexual

In the year's that you've been married, you and your wife have rarely spent a night apart, so you'd be telling a lie if you said you weren't somewhat thrilled about her week long business trip outnof town. You already had mental plans to drink too much, sit around in your boxers, maybe smoke a cigar or two and watch porn on the big television in the living r...

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