Jerking Off Wearing Lingerie Stories

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Aunt Cathy Ch. 1

by HIHEELS on Sep 13, 2017
Fetish

My Aunt Cathy had fascinated me all my like and I had only just turned seventeen. She was single and worked in a ladies department store selling women's clothing and lingerie. Cathy was in her early forties but looked like she was in her thirties. She is petite - 5' 3" and a little over 100 lbs. She had a nice figure and beautiful legs and feet which is wha...

Capitol Kathy

by MaxLoad on Sep 12, 2017
Erotic Couplings

So Kathy was 18. We had met a while back; months ago, actually. I don’t exactly remember who introduced themselves to whom, but one way or another we met, VIA Instant Messages of all things. Kathy was a freshman in college. She still lived with her parents, attending BU to save money rather than going to an out of state college. She had described herself...

Bra, the Irreplaceable Item

by sisifo on Jul 6, 2020
Fetish

I absolutely depend on bras to get sexual arousal, indulge my fantasies and reach orgasm. Somehow, my fascination with this female undergarment triggers a wild desire of submitting to the women who wear it, not implying their approval, tolerance or even awareness. This transgression -- (ab)using a bra when you're not supposed to -- boosts the native sensua...

Need a Ride

by BakersfieldCdTerri on Sep 13, 2017
Transsexuals & Crossdressers

Ever since I can remember I've loved wearing girls clothes and lingerie. I was attracted to girls and considered myself straight but still had the desire to wear panties every chance I got. So I'd sneak into my friends moms and sisters bedrooms and take some panties, bras, garters, stockings, even skirts and dresses found their way home with me. I'd wear pan...

Cuckold CEO Ch. 05

by drdick69 on Oct 9, 2018
Fetish

Day three of our vacation started with a thud. I woke up rolled over and my wife informed me that she had started her period. Well at least I was getting unlocked from my cock cage for a week. Usually, when my wife has her period, she unlocks my cage and lets me jerk off to relieve myself for a week. Sometimes we play sexy games with each other, but mostly i...

The Sitter

by sub-alan on Sep 14, 2017
Fetish

The following story was a request by a reader to be written in as a character in one of my stories. So here it is Paul, hope you like it. * * * * * My wife and I were going out for the evening and asked our neighbor, Paul, to baby-sit. Marny said she was driving so I sat in the passenger seat and settled in for a nice ride. Marny looked younger than her a...

My Present Problem

by nolimits2000 on Sep 14, 2017
BDSM

My name is Steve; I'm a single guy, early thirties, average looking, decent build, nothing special, just your average guy you would meet most anyplace. I am very shy, basically an introvert, therefore I have never been married, seldom even date. It's not that I can't get a woman, just too damn shy to approach most and ask them out. So basically I am a homebo...

Caught in a New Life Pt. 01

by Fibaro on Apr 20, 2020
Transgender & Crossdressers

(Hello everyone, this is a story that has been written for a very special reader of mine.) Intro Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn't really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to mu...

Crossdressing Playdate at the Lake

by montrealjane on Sep 16, 2017
Transsexuals & Crossdressers

At the end of the summer, I was lucky enough to have some playtime at the lake. I had been emailing and IM'ing back and forward with a girl that I had found on Craigslist. Craigslist is something of a lottery full of timewasters and scary people using many bogus identities, so it takes some time to filter out who really serious to get together and have fun,...

Never Lose a Bet with your Wife

by Everyday2 on Sep 15, 2017
Fetish

I had been married to my wife for 9 years when a life changing event happened. Julie, my wife, is a very attractive 28 year old woman. She is 5'5" tall and is in very good shape. She has a beautiful ass and likes to show it off in tight jeans and short skirts. My name is Tom, and I'm just a bit taller than her and also in very good shape. She tells me that I...