Crossdressing Stories

1,097 results
Orientation
Length
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Infinite Scroll

Pottery Party

by tophatter77 on Sep 14, 2017
Transsexuals & Crossdressers

[Our story is about a 25-year-old potter called Jeremy Harding. He makes ceramic art and is doing pretty well for himself having found some success after leaving art school. He lives and works from his studio in Bethnal Green, London. Alone, since his girlfriend, Alice, walked out on him for some other guy 6 month's ago. He still thinks about her but doesn't...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Maid The Wrong Bet...

by Lea1234 on Sep 25, 2017
Transsexuals & Crossdressers

Part 1 Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn't explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years... A friend of mine, Peter, was into the same video games as I was, and we made a bet on who would win the next ga...

Erectile Dysfunction

by chandler831 on Sep 25, 2018
Transsexuals & Crossdressers

"You can never tell anyone about this, promise?" "Yeah man, I know!" "I'm serious, dude, not a soul. I am so ashamed and it's seriously been killing me for two weeks." "Okay, just tell me, I promise I will never say anything to anyone, ever." "The reason Rachel and I broke up is because I couldn't perform." "Perform what?" "Perform... sexually?" "Like...

The Deal Ch. 01

by KaseyLegs on Jan 7, 2019
Transgender & Crossdressers

I would like to say my first time was beautiful and special, but while it was many things, it certainly wasn't either of those. To understand, you'd have to know how it came about. For years, I'd been a secret crossdresser. I shaved my body, including my arms, all the time and told people I "just don't have body hair." At home, I'd pose in front of the mirr...

Julia, Ben and Lisa Ch. 04

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 04: THURSDAY A few quick notes: 1. this is the fourth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned Julia said, "Yeah, for a minute there I thought she would think we w...

The Game Ch. 06

by MicheleNylons on Mar 12, 2019
Transgender & Crossdressers

Chapter Six - End Game March 2008 A well known online resource defines 'dogging' as: the British English slang term for engaging in sexual acts in a public or semi-public place or watching others doing so. There may be more than two participants; both group sex and gang banging can be included. As observation is encouraged, voyeurism and exhibitionism ar...

Husband's Transformation Ch. 01

by Prematurelimphubby on Jun 10, 2019
Transgender & Crossdressers

Brett was sitting at home alone while his wife Mandi was gone shopping. It had been a few days since their last sexual escapades. He was horny and he wanted release. He went to the bedroom and opened Mandi's drawer. He loved her panties and wore them often whenever he was home alone. In fact, he's even wore a pair while she was home. They were relatively t...

How I Became a Sissy Slave

by Sissy_Sasha on Jul 27, 2020
Transgender & Crossdressers

I had never been so embarrassed in my life. The woman in front of me looked at me with disgust that burgeoned on fear. Seconds prior, I was knocking on her door and ringing her doorbell expecting for a man to answer. This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...