Caught Wearing Frilly Pink Knickers Stories

266,857 results
Orientation
Length
Source
Infinite Scroll

A Sexual Secretary Introduction

by officeslut on Sep 14, 2017
Erotic Couplings

* The following story is from my real life experiences with as little embellishment as possible. * Since I was 15 I've known I'm an attractive woman, I have a curved and toned 5' 2" frame with 28 C breasts which are usually out on show with a vest top or low cut dress. I live and work in London, which is the perfect place for me, plenty of gorgeous shops t...

The Making of Davina Ch. 01

by Timewarp10 on Oct 31, 2018
Transgender & Crossdressers

It was 1966, England had won the World Cup! The swinging sixties were in full swing. David had started working in the sale's office of Telford Safety Engineering Ltd. He held the grand title of Assistant to the Sales Manager, which meant in reality he was the office boy; he ran errands and made the tea. At eighteen, it wasn't his first job. Since leaving sch...

Made to Obey Ch. 11

by madetoobey on Aug 21, 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...

Lost Luggage

by Tomsparty on Sep 18, 2017
Transsexuals & Crossdressers

As usual my mum took great delight in telling my new girlfriend the lost luggage story. I took Clare to her house for Sunday lunch and told mum specifically not to embarrass me with any of my childhood stories or old photographs. She was on her best behaviour during the meal but afterwards as we sat down in the lounge for coffee she was true to form. She qui...

An Avenger's Possession

by terminatrix92 on Sep 16, 2017
Celebrities & Fan Fiction

This is the 7th part of a Black Widow series starting with: An Avenger's Initiation. ***** "Mmmmmm..." Natasha Romanoff purred, her sultry distinctive drawl wavering as her enchanting young lover insistently pleasured the Avenger. Laid out on a huge double bed, her wavy red hair cascaded over plump white pillows, Natasha gazing adoringly up at the beauti...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...

Taxi Office

by wifwat on Sep 12, 2017
Loving Wives

It was the evening of my office Christmas party and my wife Trish who works for the same company had her own office party. I went up to her department as our party was closing down. There wasn’t many people left at their party either. I couldn’t see Trish at first and went looking for her. I found her in a side office asleep on a couch. She was sprawled out...

How I Learned to Watch

by KittyO on Sep 16, 2017
Exhibitionist & Voyeur

The first time it happened by accident, at least on my end. On the Friday, I had moved in with a new flat mate, a woman I know from work. She'd given me the keys and gone to off to Brighton. I didn't expect her to be at home when I walked in on Monday afternoon. In fact, I thought that the noise from her bedroom was the alarm on her radio which had gone off...

Teacher's Discipline Ch. 04

by tom6432 on Sep 26, 2017
Fetish

(This is a fantasy written for fun. All characters are age 18 and over. If you do not enjoy spanking, humiliation and some fetish please do not read, as you will not enjoy the story. Thank you.) The school bell rang ending the Mathematics class I was mentoring. The girls waited until I dismissed them, and began to file out of the room. The second group o...

James' Transformation Ch. 2

by Dragonia on Aug 30, 2017
Fetish

As Jenny drove the car felt strange, she pulled over to the curb. She moved the seat forward and adjusted the wing and rear-view mirrors; she couldn’t help but take a long look at her pretty face as she did. "That’s better," she said to herself as she sat back in the seat. Driving in her heels wasn’t as difficult as she first thought it was and now pulled ou...