Jerking Off Wearing Lingerie Stories

339,936 results
Orientation
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Infinite Scroll

For His Mistress's Pleasure Ch. 01

by femmepen on Sep 17, 2017
BDSM

A deep sigh escaped my lips as I shivered from the chill in the air. Though the temperature was around 75 degrees the cool cement of the ground did not help in preserving my body heat and neither did my lack of wardrobe. I shivered again taking deep breathes each time to calm my nervous soul as well as to clear my head in preparation. My Mistress had told me...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

A New Slave Ch. 03

by jdk0210 on Sep 14, 2017
Fetish

I took a deep breath as I walked through the door of my apartment. Met by the similar smell of home, I was suddenly consumed with fatigue from the events that played out earlier today. Finally reaching the bed, I collapsed onto my hard mattress, slowly replaying what had just transpired not two hours ago. The pain in my ass, ache in my jaw, and burn in my ch...

The Perfect Blowjob

by ScarlettFaye on Nov 27, 2018
Erotic Couplings

1. Finally, I think to myself as I hear the front door open downstairs. I've been waiting for you all day. You got home late again, but I don't blame you. I know your boss has been working you like a dog these last couple of weeks, with performance reviews just around the corner, but I also know that it's because he can't trust anyone else to do the job rig...

My Valentine

by sexyctcd on Sep 15, 2017
Transsexuals & Crossdressers

It had been about a month since my first experience with Eric, my next door neighbor. We had met about a dozen times since then for some kind of sex. We were getting comfortable in our boundaries and meetings. I had been shopping online and had slightly increased my clothing, makeup etc. and Eric had offered his shop as a delivery location. He got packages t...

Bringing out his Inner Sissy

by jessikab on Sep 24, 2019
Transgender & Crossdressers

I can vividly remember the first time I decided I would feminise my husband. We had been going out for about 18 months and had celebrated living together for exactly three months by going down to the pub beside the laundrette for a drink or two while we waited for our clothes wash. I had noticed pretty early on how Steve seemed entranced by my underwear and...

Revelations of Amanda Ch. 03

by Alkino on Oct 5, 2020
Exhibitionist & Voyeur

After they kissed goodbye and Amanda left to see her mother, John finally had the apartment to himself for a couple of hours. He was actually looking forward to it: it had been a crazy week and a half, and he wanted to clear his head, something that had become nearly impossible with his girlfriend around. Standing by the bedroom window and looking at some ki...

Trish's Weekend with Sean Ch. 03

by sparkyinoh on Nov 18, 2019
Fetish

"Feel free to read the 1st part "an unknowing cuckold Pt 1" and also the 1st two chapters of "Trish's weekend with Sean". ***** The week progressed rather uneventful- work, dinner, cut the grass- a typical week for most. My ass was feeling better by Thursday and I was able to use my office chair again. I was thinking to myself if anyone in the office was...

Sissy Maid Son Pt. 02

by Robyn228 on Jul 18, 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 wept on his mother's bed feeling violated and abused. The maid uniform still on...

Panty Wank Obsession Pt. 01

by stroker00 on Sep 14, 2017
Fetish

Chapter 1 I am in my 60's, single and semi retired & so have lots of time to plan my big wank sessions. I am obsessed with jerking off while wearing panties While I have bought panties myself I prefer to use panties that have been worn by girls that I know. I spent lots of time working out how to get these 'used' panties. I live in a block of apartments...