Caught Wearing Lingerie Stories

246,216 results
Orientation
Length
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Infinite Scroll

The Gift

by japkin on Sep 13, 2017
Erotic Couplings

"Hello. Welcome to the Bedside Boutique. May I help you?" "No, thank you," Daphne said. She had been there before, but this time she was not looking for something for herself. She was going to a bridal lingerie party for one of her friends and wanted to get her something embarrassingly racy. Fortunately, her friend was the same size, so shopping was easy....

The Agency Ch. 11 (M. Trainor Pt. 02)

by tnhardon on Sep 25, 2017
Celebrities & Fan Fiction

The morning following my first night with Meghan, we both agreed that it would be best to have an off day after a night of pleasuring her. Meghan's body was sore and tired from the powerful orgasms, and my tongue was sore from our long session. On off days, when Meghan got done with her concert, we would hang out in the living area and talk. I learned abou...

The Party

by Teddybearsubmissive on Sep 15, 2017
Toys & Masturbation

Thanks to bear2read for editing this story. Veronica entered the store with excitement and fear. She tried her best to stay away from the lingerie department, but this time she had no choice. She had to pick out a piece of lingerie for the party, and the party was tonight. Her dislike of the lingerie department had caused her to wait until the last minute....

Whispers

by lovinlife0828 on Sep 15, 2017
Illustrated

Note: This is a story that another reader asked me to write. They gave me a brief outline and I went from there. I have added a few drawings that I did. If you are a reader who gets offended when the wife has sex with someone else, please stop now. This story is not for you. I hope that you enjoy this little sexcapade. * Allow me to introduce myself. My n...

Chris' Adventures Ch. 04

by curiousone43 on Apr 17, 2018
Fetish

Sunlight streamed through windows and played across Christy and Patty's bodies as they lay there in bed. Christy's arm was draped over Patty, cupping one of her large breasts and Patty was curled up in a fetal position next to Christy. Christy stirred and rolled over stretching out and trying not to wake up Patty. She rolled over to see what time it was, 9:0...

Closet Sissy Son Made Into Daughter

by JD2100 on Nov 18, 2019
Transgender & Crossdressers

Why was I on all fours with my dad's cock in my ass and my sister's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my sister's lingerie. It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had...

Modelling Ch. 01

by HeatherMaureen on Oct 15, 2017
Transsexuals & Crossdressers

I'd woken up wearing a babydoll nitie before, but not in the bed of a strange man in a strange room. I was horrified at my actions the night before. Not only agreeing to go to his place and model his wife's lingerie for him but sucking his cock till it exploded in my face and then agreeing to stay the night and model more for him today. What was I thinking?...

Sexual Awakening

by Charles36 on Sep 17, 2017
Mature

I drove to, Arizona on Saturday the 26th of October 1996. On the way I spun a sexual fantasy. During my five-day stay in Scottsdale I wrote a longhand draft. The story is about a couple who have been married for several years. They have no children. The husband is sterile—the result of a childhood disease. Her mother was quite prudish and she had adopted m...

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...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...