Start Smoking And Crossdressing Stories

359,826 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

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...

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...

My Wife Cheated, But I Liked It

by Jackb120 on May 6, 2019
Interracial Love

I've always been the average guy. I'm into normal things like working out, watching TV, and drinking beer with my friends. That said, I was shown porn as a teenager and found myself into interracial cuckolding and even crossdressing before I had my first real girlfriend. After highschool I moved away from home and stopped the crossdressing but kept the porn...

A Night to Remember Ch. 02

by Master_and_Sex_Kitten on Sep 16, 2017
Transsexuals & Crossdressers

Happy Birthday to me...Friday April 24th was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go! * Author's note: If you haven't read part one -- A Night To Remember -- that might help provide a little context :P this is a transsexual story about love, confusion and exploring a new world of sex. Enjoy! --...

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....

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

My New Family Ch. 03

by eagle166 on Sep 15, 2017
Transsexuals & Crossdressers

Lying in bed talking to my wife, Heather. Rubbing her large swollen belly, Heather is pregnant with twins. Things haven't gone as well as we would have liked. Yes we are still very much in love, so there is no problem there. But Heather is 8 months and 1 week into the pregnancy and with twins, she has been very uncomfortable to say the least. Rubbing her b...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

Open in Reader