Caught Wearing Stories

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Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

Bikini Bottomed

by CrossdresserCaitlyn on Jun 25, 2019
Transgender & Crossdressers

Since I can remember I loved wearing panties but my ex hated the thought of it. It almost ended our relationship early on. I decided that I loved her more than wearing panties so I quit for the first few years of our relationship. The urge to wear panties came and went often but I was able to avoid them. That all changed one day I was home alone and horny....

A Fateful Trip Pt. 02

by TTM86 on Mar 13, 2018
Transsexuals & Crossdressers

My wife was waiting for me to pick her up and I was stuck wearing pink heels. I could run home quickly to pick up regular shoes, but our house was a 'smart' house with alarm. If I opened the garage door, front or back doors a notification would hit her phone, which would require a lot of explanation. Even if I managed to find a way inside the house, I would...

The Panty Club Ch. 01

by nikki_2021 on Sep 18, 2017
Fetish

Amber watched as Teri and Abby walked off together. How completely childish, she thought to herself, pondering the exchange. "It's a club sorry Ams and we're not in charge so we can't bring you in," Abby had said. "What sort of club?" she'd asked. "We're not allowed to say," Teri had told her. At least they had looked genuinely apologetic about it as the...

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...

The Revenge

by hotice0090 on Sep 17, 2017
Loving Wives

As I reached near the swimming pool, I saw my wife, Tanya, 29, waving towards me. I waved back. She came out of the pool. She was quite fair and was wearing her pink colored bikini. As she paced towards the change room I saw her juicy melons juggling, desperate to come out. As she entered the change room water was still dripping from her round, tight and sha...

CD Internship Ch. 02 - Shopping Emergency

by cdtycoon on Mar 17, 2020
Transgender & Crossdressers

All the characters in this story are above 18. ------------------------------- SHOPPING The next day was Sunday, so I got up late at 7:30 took a nice bath by washing my hair, shaving my legs even though it was a holiday and also shaved my public hairs leaving only a landing strip. I also used hair remover to remove hair from the hands and upper body. Th...

Caught in Panties Ch. 02

by littlejoe10 on Aug 31, 2017
Exhibitionist & Voyeur

This is a follow up to my story "Caught in Panties" in which two middle aged women I work with discover I was wearing women's panties. The day after being caught the women said nothing and went about their daily routine. As for me I was a little self conscious and still embarrassed over being caught and having the women know my little secret. I avoided t...

Caught in Panties Ch. 01

by pantyperv on Sep 25, 2017
Fetish

I have a beautiful wife who I adore more than anything in this world. We’ve been married for about four years, but she is the only woman I have been with for the past ten years. She is six years my junior and I waited until I was in my thirties before I finally asked her to marry me. She is 5’8”, blonde hair, blue eyes, and has a smoking body. I catch other...

Sarah Wore a Bikini to the Hot Tub

by SarahCD on Feb 11, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...