Caught Cross Dressing Stories

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These Boots are Made for Sniffing

by MarksAdams on Jul 15, 2020
Fetish

Adam watched as Kim walked down stairs in her skinny jeans and cream fitted silk blouse. She had her black leather boots in her hand which got Adams full attention. They were her stiletto ankle boots. Pointed toe and a zip on the side. "I'll meet you at the pub later then?" She said as she sat on sofa. "Yeah, there's a few of us going so I'll slip out whe...

Be Careful What You Ask For...

by StephanieLGFrancis on Sep 16, 2017
Transsexuals & Crossdressers

I've been living with Janet for ten years now and for the first eight all was well. But over the last two years things have changed completely, and not for the better. I started looking at various sites over the years, you know the type, and I concentrated on cross-dressing and transvestite sites. But this would only be every now and then. I did look at othe...

Cindy's Makeover

by CindyUSA on Sep 16, 2017
Transsexuals & Crossdressers

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dre...

Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...

Pussy-Licker: The Man Who Loved Vaginas

by tristantrotsky on Jul 13, 2020
Group Sex

The Yorkshire village of Hornsthwaitedale straddles the lazy curve of the river around the old stone bridge where the oak tree bends low beneath the lush weight of its own greenery, and willows ripple shadows up from the shingle riverbank across the cemetery towards the tall spire of the Norman church. Several narrow ginnels and snickets radiate between clus...

Influential Factors! Ch. 15

by gummidurango60 on Jan 1, 2019
Transgender & Crossdressers

I woke in horror; only to realize I was in bed... my bed. Nothing seems to have changed from yesterday; I was still in my LA Rams Cheerleading outfit... boots and all. I reached up and felt the collar around my neck, it wasn't tight; but it wasn't loose either; and to my delight the cuffs were gone. I got out of the bed and headed toward the bathroom to d...

Caught

by Geraldine01 on Jul 27, 2020
Transgender & Crossdressers

My name is Geraldine and here is a story of how a friend discovered that I was a secret cross dresser. The experience I am about to tell you about happened when I was about 23. I had been dressing for years and loved how sexy wearing female clothing made me feel. I about 5ft 7 and have a very slim and toned body which I keep in shape by going to the gym and...

Freddie Becomes a Cross-Dresser Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Now, that I bought everything that I needed to transform myself from a handsome and modest man to a beautiful and sexy woman, I realized that I had completed the easy part in buying the clothes, the makeup, and the perfume. The difficult part, of course, would be dressing up like a woman without having a woman there to help me. I certainly did not want to as...

Sonia's Panty Slave

by illegalsmile38 on Sep 17, 2017
Fetish

This is a variation on a theme dear to the hearts of many (or at least some). If you feel like voting – vote. If you can't be bothered – I don't care. If you feel like giving me feedback – then do. If you can't be stuffed – then pour yourself another glass of wine and skip on to the next rollocking yarn. The fishnet pull-up stockings were stretched up over...

Hot Sex Instead of Dancing Ch. 02

by SusanJillParker on Sep 12, 2017
Toys & Masturbation

Please give me the support of your vote. * Walter masturbates himself while watching his shapely neighbor cleaning her kitchen in her sexy nightgown. Bill worked long hours as a desk sergeant and wasn't always home to care for such a beautiful woman. As far as Walter was concerned, if Tiffany was his wife, he'd never leave her side but realistically, he'd...