Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Shopping Can be Fun!

by Wetfemme on Sep 1, 2017
Group Sex

I actually talked my boyfriend into going shopping with me, because I told him that I needed to find a skimpy sundress, and that I would "model" it for him before making the purchase. I'm about 5'8", with long blonde hair, light blue eyes, and my chest is a 36C. I found a cute, cotton light blue dress with little flowers on it. It had thin spaghetti straps...

Dancing the Night Away

by erzherzog on Sep 13, 2017
Exhibitionist & Voyeur

Erika and Maggie sat in the vast lounge area of the Las Vegas hotel they were staying at for the conference. It was a splendid setting, filled with sun and lots of people tracking about. Both women were enjoying a Cosmopolitan and some snacks. The night before had been great, especially the visit to that huge club with the all male review. Both women talked...

My Skin

by Brandie69 on Aug 19, 2017
Exhibitionist & Voyeur

Fair warning: this is a very slow story exploring the feelings of a woman discovering that she is an exhibitionist. There is nudity but no sex. It was written primarily as an exercise. Read on, if you care. Let's get this out there. Confess it, like I used to do on second dates with the boys I met back then. It's like this: when I was in college, I strip...

One Hour to Close

by averykinkybunny on Sep 3, 2017
Exhibitionist & Voyeur

Heather watched the clock tick away the last few seconds to 10'oclock, the final hour of the shift. "Okay it's time are you ready?" It was Shawn her co-worker. She let out a deep breath. I'm ready I don't know how you talked me into this. "Hey, a bet's a bet." he said It was Sunday night, closing shift the deadest night of the week and it was only the two...

A Helping Hand

by Isabella_1978_UK on Sep 2, 2017
Exhibitionist & Voyeur

It was 'that' time of the year again, annual inspection of our rented property, I had been through hundreds of these inspections, no, you've got me all wrong; I've not lived in the rented house for hundreds of years. My husband's family own a shitload of properties, ours included, I had been out with James on holiday many times and had been around properties...

Le Expo

by Orangecounty932 on Aug 19, 2017
Exhibitionist & Voyeur

Laura walked briskly through the mall, her brown oxford pumps pounding the tile, frowning. She had just wasted the better part of the morning in an unsuccessful search for a new dress. Normally, shopping offered a pleasant departure from the pressures of work and "grad" school, but this time, that wasn't the case. Her cousin's wedding was Saturday and she ne...

Secret Boutique

by Trubbycat on Sep 25, 2017
Fetish

My hands trembled slightly as I gripped the Camry's steering wheel. Today I was finally going to do it. I had arranged for a day off from work. There would be no time constraints, no lunch hour pressure. The boredom I had felt with Mark, and the fear that it might be bad news for the relationship, was compelling me to try something new. It took nerve to call...

Lines Are Crossed at the Beach Ch. 02

by ManOSafety on Sep 13, 2017
Group Sex

Special thanks to Redhairedandfriendly for the editing help. * The following morning, I wake up while it is still dark outside. I pull on a bathing suit, t-shirt and flip-flops, step into the kitchen and eat a Pop-Tart and have a glass of juice. While I eat my breakfast, Brad comes into the kitchen and fixes himself something to eat. After a few minutes w...

The Meeting Ch. 02

by Jack1107 on Jul 10, 2018
Mature

Jack replied, "I would love a coffee, but I also would like some lunch. There's an excellent Greek restaurant that serves the best moussaka that you have ever tasted. Would you like to join me for lunch?" Margit smiled and said, "I love moussaka, I cook it often with ten good portions which I freeze then I can eat it when I want to. I would love to join you...

The Trap Ch. 02: Paula is Prepared

by Paulateevee on Mar 23, 2020
Transgender & Crossdressers

Thank you for the positive feedback on Part one of the story. This part has a lot more sexual content as Louise meets with Paula and is still 90% actually what happened.. The usual disclaimer applied. Everyone is (well!) above the age of consent. This story is about crossdressing. If that's not what you like how did you get to this page 😊 I hope you enjoy...