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...

The Switch Hitter

by Biskit on Sep 12, 2017
Transsexuals & Crossdressers

This love story could have been submitted in the Incest section but since for the most part its bisexual, transsexual and cross-dressing, I decided not to offend the incest purist and submit it here. All the characters are of course fictional. Not sure why I couldn't get one of the volunteer editors to help me, lord knows I needed one and I certainly did try...

1963

by cerection on Sep 16, 2017
First Time

I love to jerk off. I loved it the first time, and I love it thirty six years later. I hope I'll always love it. No matter what my lovers have thought, yes it's sexual, but it has absolutely nothing to do with my sex with them. My masturbating has nothing to do with whether I like sex with them, it doesn't mean I do or don't want sex with them. It's just tha...

Made to Obey Ch. 02

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Reprise: I had been watching shemale porn when alone in my Sister-in-law's house. Tempted into wearing some of her underwear whilst masturbating, my wife (Ruth), sister-in-law (Esther) and their mother (Donna) came home much earlier than expected and caught me in the act. * I scampered up the stairs, still dressed in the suspender-belt, stockings and panti...

Made to Obey Ch. 12

by madetoobey on Aug 26, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being uncovered. I'...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...

Made to Obey Ch. 10

by madetoobey on Aug 6, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Made to Obey Ch. 13

by madetoobey on Sep 9, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to start wearing panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being unco...

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...

Addiction to Lingerie

by grgy56 on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Lora was the most perfect girlfriend. Her pretty face and rocking hot body were the envy of other women. When we were dating, Lora would do almost anything for me. Sex anywhere; any time; in public or private. But one of the hottest things was seeing her dressed in sexy lingerie. Lora wore it under her business suits to work, out to dinner and...