Jerking Off Wearing Lingerie Stories

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Sissy Maid Son Pt. 01

by Robyn228 on Jul 16, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter walked into his house, feeling excitement clenching in his stomach. He's been pa...

My Friend, His Wife

by hollandguy on Sep 16, 2017
Transsexuals & Crossdressers

Okay this is my first ever stab at a story so please cut me some slack. Intro: Hi my name is Ryan and this is my story The following is 100% true and I have not changed the names as no one is innocent. So about me I am a 35 year old WM, I am 5'11" and 165lbs with a pretty thick 7" cock. I have been a closet cross- dresser since the age of 11 when I discove...

My New Life in Lingerie

by Everyday2 on Jul 14, 2020
Transgender & Crossdressers

It started innocently enough. There was that time many years ago when I saw a pair of my wife's panties in the laundry hamper. I couldn't help myself and decided to try them on. They were amazing! The way they hugged my ass and balls is impossible to describe. I left them on most of the day as my wife was gone to work. Walking in the panties made me hard, an...

Brother In Law Spends The Night

by NicolePink on Sep 12, 2017
Exhibitionist & Voyeur

I can't stop thinking about a kinky experience that I shared with my husband and his brother. Even though it happened six months ago, it still makes me feel extremely naughty every time I relive it in my mind. My name is Nicole, I am 135lbs, 5'10" brown hair and eyes. I like to stay in shape, as I'm getting older, at 28 years of age. I've been told my whol...

My Sexual Story Ch. 02

by bisexual_slut on Sep 14, 2017
Erotic Couplings

Since then she has stopped having sex with other men and we got married and sex became ordinary between us but she is still a very horny woman and wants sex all the time from me, which I am not complaining about. She has also put on a couple of kilos or so since we first started dating. However, I still have my kinky desires and although we have good sex I s...

The Maid and the Pizza Guy

by hollandguy on Sep 13, 2017
Transsexuals & Crossdressers

My name is Ryan I am 33 years old. I am 6'1 #200 with auburn hair and brown eyes. I am not in the best shape anymore but I wouldn't call myself fat either. I have been cross-dressing since the age of eleven. It started with just panties but has evolved to full dress over the years. I work as an electrician and take on side jobs when I can. With the recent...

Window Lady

by dsoul on Aug 31, 2017
Exhibitionist & Voyeur

The rain is pouring outside like mad. The street is empty of walking pedestrians except for moving automobiles. Claps of thunder echo across the dark underbelly of the sky. It’s been pouring like this since the new week began. It is past eight in the evening. Soft music is coming off the little radio by the head of my bed but my mind is barely hearing it....

Slut: My Stripper Slut Wife Pt. 02

by NeilMc123 on Sep 26, 2017
Loving Wives

I've just dropped my lingerie clad wife off at a hotel in the city centre, to be fucked in all of her holes, by a client she has already cheated on me with, wearing the lingerie that he bought her! She met him at the club where she works as a Stripper. She'd only been working as a Stripper for two weeks, but here she was fucking her client, for the second...

Wife Converts Husband Ch. 01

by bisexual_slut on Sep 25, 2017
Transsexuals & Crossdressers

This story is totally fictional and any resemblance to anyone is purely coincidental. My name is Tony and I am 5'8" in height, weighing only 58 kilograms, with no body fat and a figure most girls would kill for according to all of the girls I know. I have an olive complexion and tan very nicely, I have short brown hair and hazel coloured eyes. I am in my la...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...