Crossdressing Stories Stories

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Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Erika's Story Ch. 03

by Quantarx on Jan 22, 2020
Transgender & Crossdressers

This is the third part in Erika and Mary's widening exploration of crossdressing, if you have not read the first couple chapters I encourage you to go back and read those first. also, thanks for the feedback I have received and please continue to rate and leave feedback and comments so I can continue to evolve as a writer. *** I lay in bed with my loving...

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...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Cindy's Panties

by secretanon on Sep 13, 2017
Fetish

I am around 24 years old and I have always enjoyed wearing panties. I think the feminine feeling of it all really turns me on. At a young age, I discovered masturbation from cumming on my mothers panties after deciding to be bold and try one out from curiosity. I was never able to fufil my love for panties, being in a house full of males, so I never had a si...

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:...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Things That Turn Me On

by Raquels_Panties on Apr 22, 2020
Fetish

I'm a 28-year old male. I live a normal life in public. I like women and men. I'm 5'8" tall and weigh 135 pounds. One might consider my features, my face, my body shape, more on the feminine side of the spectrum, than on the masculine. I'm okay with with that. I use this to my advantage and have allowed my hair to grow out. It falls just below my shoulders....

Me & My Wife Are Sisters Now Ch. 01

by gayindia1980 on Sep 16, 2017
Fetish

Hi I am Ravi, 28 year old from Delhi 5.8, slim, hairless and minimal facial hairs. I am married for 3 years, my wife Shivika is 24, 5.4, slim and beautiful. I was in crossdressing since my school days. I use to wear my sister's and mom's clothes when nobody used to be at home. In 12th class I lost my virginity to a college guy whom I met online but that anot...