Crossdressing Smoking Stories

17,384 results
Orientation
Length
Source
Infinite Scroll

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...

Confession

by holukukkar on Dec 10, 2018
Transgender & Crossdressers

Hello Everyone, This all started when I was 18 years old. Just like any other 18 years old boy I was browsing through the porn website for some porn to watch when I came across a crossdressing video in which the man was forced to wear female clothes, accessories and makeup and then treated as slave to do household chores and then fucked in ass by strapon....

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

So You Want to be a Nurse? Ch. 06

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six - Retribution 'Dr Stephen Mortlock esq' the card read followed by his phone number and his work address in a suite of offices used by medical specialists. The folded piece of paper attached by a paperclip read: 'Be there at 7PM sharp. He likes the nurse uniform so wear it and get dressed before you go. Go there and back in a hire car; Polly wi...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

College Crossdressing Confessions Ch. 03

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the third in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first two installments for context. *...

Feminine Fate Fulfilled

by mattpantyhose on Jun 15, 2020
Transsexual

Like all of my other stories this one had been already published on Literotica. You can find it here: https://www.literotica.com/s/feminine-fate-fulfilled__ For whatever reason Chyoa doesn't include Crossdressing in the category of Transsexual and doesn't have a separate category for that theme. This story does not include any transsexuals, but I considered...

Open in Reader

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

Sarah has a Crossdressing Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before e...