Halloween Crossdress Stories

5,980 results
Orientation
Length
Source
Infinite Scroll

Relax

by BoredTBDL2 on Jan 7, 2021
Fetish

“Jesus man, that’s a lot.” Mike stared at the old metal table between you two in the middle of his backyard patio for what felt like several minutes. You couldn’t blame him for taking his time though; you two were just gonna meet up for drinks, but the alcohol had other plans, and now you feel like you need to pay your friend for being your therapist. “I don...

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Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...

Just a Normal Couple

by Feinux on Sep 25, 2018
Transsexuals & Crossdressers

To the untrained eye we look like just another normal couple walking down the street. Beautiful girl with a handsome guy, both smiling and laughing, holding hands with each other. But if you were to look a bit closer you would realise not all is as it seems. You see, my name is Paul and I am the beautiful girl. My girlfriend's name is Sarah and she is the ha...

Lingerie Does Make the Man Ch. 02

by lingerielover on Sep 16, 2017
Fetish

If you had read my last story you would know by now that I love to wear women's lingerie. I no longer wear guy underwear except when I go to the doctor, I only wear panties. It doesn't matter what type of panties as long as they are either silk or lace, no cotton ones for me. My wife is some what supportive, but she doesn't fully approve either. We have been...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

A New Direction Ch. 01

by MyUncensoredSelf on Sep 15, 2017
Transsexuals & Crossdressers

I was nervous when I texted my wife that morning. She'd gone to the shops and I asked her to buy me some nylons. She knew I liked to crossdress and we'd even fooled around once while dating with me in a leopard print stretch leotard and my breast forms. She'd loved it that time and it was one of the horniest weekends we had together. But since then things ha...

Other Side of the Coin

by NaomiQ on Sep 15, 2017
Transsexuals & Crossdressers

If this is at all popular I will continue the story. The next chapters will be much more sex driven and dirty. ***** "So, you're saying that all I have to do is imagine myself as another form?" Michael asked. "Yes, but you must concentrate deeply in order for the transformation to take place. The change can be as simple as adding a freckle or as drastic a...

What if...

by protoborg on Dec 5, 2015
Miscellaneous

You stand looking about yourself. There is nothing but white in all directions. Nothing but solid, unending white as far as the eye can see and probably further than that. There is light or there isn't. The vast whiteness of the place you find yourself in makes it very hard to tell. The only thing you can be sure of is that you are standing naked in a seemin...

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Chance Meeting on eBay of All Place

by Leighharding on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story of a chance meeting which has turned out to be really rather amazing and surprising. ***** I was trolling eBay for some underwear to buy when I happened on a rather large lady selling some used kit. I messaged her to ask specific sizes and she responded straight away asking if it was for me. Normally I would deny that I was buying...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...