Masturbating Wearing Lingerie Stories

190,682 results
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Infinite Scroll

The Making of an Angel Pt. 02

by AngelLawrence on Jul 29, 2019
Transgender & Crossdressers

This is the 2nd stage of my biography of how I went from vanilla male to shemale slut. All persons are over the age of 18. *** I gulped. The close proximity of the woman and all the pretty lingerie in front of me was making me feel light headed. "What size are you?" She asked. "28" waist 38" chest" I replied. "No silly! What girl size are you?" she...

Blonde on the Bench

by AceStroker on Sep 1, 2017
Exhibitionist & Voyeur

There she was, a young woman from the local college, sitting all by herself on one of those benches inside of the busy mall. She was quite a cute girl, one whose beauty and sexual flavor caught my eye long enough for me to discover something else very interesting about her. She had dirty blond hair tied neatly in the back, wore a light jacket, and an extreme...

Anne's First Porn Shoot

by Sunupper on Sep 13, 2017
Exhibitionist & Voyeur

Anne watched as the three slim, attractive black men approached her. They'd never met but they were going to fuck her with several people watching. Anne was already semi-naked wearing just a tiny pair of panties and a small camisole. She was already wet and her nipples were clearly puffed up underneath the sheer material. This was Anne's first porn shoot --...

Maid to Order Ch. 01

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele Ascending My wife had left me a year ago. I'm surprised she waited as long as she did really. We were married when we were both eighteen when I was in the army. She had been my only girlfriend and I was scared she wouldn't wait for me because I was being deployed overseas. It was a whirlwind romance. I'd heard rumours that she'd been a bit loose be...

Sexy Slut Fantasy Ch. 03

by pdavis616 on Sep 15, 2017
Transsexuals & Crossdressers

I couldn't believe that I was really going out in public like this! Much less going to the mall with my girlfriend. I began to feel really vulnerable in my tiny sun dress and high heels as I walked across the parking lot. I had so much skin showing and the silky smooth lingerie rubbing against my body was a constant reminder of how sexy I was dressed. I had...

The Life of Janice Ch. 05

by Kim_Oh_No on Sep 16, 2017
Transsexuals & Crossdressers

For several years I explored life as Janice. There are so many stories that I'm not sure I could ever tell them all, or even remember everything that happened. My life as Janice changed so dramatically over those first few years. It started with wearing women's clothing for grief comfort and turned into a whirlwind of sexual exploits and adventures. I'm old...

Panty Consequences No. 06

by PantiesAndPies on Sep 16, 2017
Fetish

This series of stories are all standalone so can be read in any sequence. They are about my favourite fantasy --- my first time wearing, or first time being caught wearing panties. Obviously then they all involve lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men amongst other things. If any of these are lik...

Rick and Darcy Have Some Fun

by rachlou on Sep 1, 2017
Humor & Satire

This story is just a bit of light hearted fun. There are no great charactersations, just pure smut for the most part. I hope you get a chuckle from it at the very least. Unless of course this exact same scenario has actually happened to you. In that case, you have my sincere condolences. Feel free to contact me and i'll give you the number of a great thera...

My Name is Raquel Ch. 03

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. I started out as a thirty-something guy with a fetish for masturbating with and in panties. I was caught and eventually transformed into a girl, Raquel, by my 18-year old stepdaughter, Jessica. Jessica unlocked my inner desires and expanded my horizons. I was now into fully dressing in all varieties of lingerie. And...

Exhibitionism - Games Women Play Ch. 01

by MotherandSonTrueConfessions on Sep 23, 2019
Exhibitionist & Voyeur

Most women are exhibitionists. Luckily for men, nearly all men are voyeurs. While making their flashes appear unintentional and/or accidental, many women show men what they all, seemingly, hope and want to see. Playing on men's inherent penchant for voyeurism, exhibitionism is a sexy game that some women play to sexually tease and erotically entice men. Whi...