Caught Dressed As A Girl Stories

361,457 results
Orientation
Length
Source
Infinite Scroll

The Mentor

by yarnspinnerr on Mar 17, 2020
Group Sex

All characters are fictional. Don't forget to vote and comment! Thanks, yarnspinnerr ;-> *** Ruth and Carli made their way to the front door of the elegant house that Ruth and her husband Roger called home. They were giggling like schoolgirls at the suggestive comments Ruth had made to the taxi driver. The young man was thoroughly scandalized by Ruth'...

Ice Cream Girl

by SlickNick2412 on Sep 13, 2017
First Time

She spent the summer working at the ice cream shop down the road from my house, and was the most adorable creature I had seen since moving there. At 22, I had taken a position as a night DJ at a local radio station about two hours drive from the college I had finished my broadcasting degree at. It was a small time gig, but the pay was decent, and a single gu...

My Adventures in CFNM Ch. 02

by sweetlucky12 on Sep 12, 2017
Loving Wives

"So, what are you ladies doing this weekend," Cathy asked in a hushed tone. It had been about 3 weeks since our ski trip turned naughty, and there hadn't really been any mention of it between my three friends and I. Maybe we were still in shock from the CFNM expereince or maybe the awkwardness of seeing each other's husbands in the nude caught up with us, b...

Stacey's Brother

by WhiskeyIsGood on Dec 2, 2019
Transgender & Crossdressers

A little one-shot that I came up with a couple weeks ago. Hope you all enjoy. Whiskey *** "Stace, please...pick up your phone!" I hung up, after leaving the third voicemail that night, and sighed in frustration as I threw my phone onto my mattress and flopped down alongside it. It had been a whole day since we last spoke when she told me that she did n...

Rose

by StrawberryDreams on Sep 14, 2017
Erotic Couplings

This was crazy, she thought as she contemplated turning right the hell around and going home, what the hell have I gotten myself into? She really hadn't gotten into anything yet. She could still turn back as she hadn't quite gotten the courage to knock on the door, but the fact that she was even here right now was blowing her mind. Here, at a stranger's hou...

A Black Stud & My Future Wife

by English Bob on Sep 11, 2017
Interracial Love

I guess at one time or other, some of you guys out there will have been with a prostitute. Perhaps your wife knew, perhaps she didn't. Perhaps you weren't married and just looking for sex without any attachments. Maybe you went by yourself, maybe in a pair or even a group. Perhaps you cared who she was, more probably you didn't. Did you look at her face whil...

The Reunion

by the_shires on Sep 12, 2017
Erotic Couplings

Dee Sanders walked into her old high school and looked around. Since she'd graduated a new wing had been added for athletics, and the school had been repainted. Pretty much everything else was the same as she remembered. She was greeted by lots of smiling faces, but if she was being honest with herself, not even the name tags rang a bell. It had been 10 ye...

Our Hedonistic Vacation

by swingerjoe on Sep 19, 2017
Group Sex

I collapsed backward into the bubbling water and expelled a heavy sigh. Finally, we had made it. It had taken nearly a full day to get to Hedonism II resort in Jamaica, but after two long plane rides, an interminable amount of time at two different airports, and a very long bus ride (with full bladders, mind you), my wife and I had finally reached our destin...

Academy of Sexual Studies Ch. 01

by daveball500 on Sep 13, 2017
Group Sex

As I took off my clothes behind the screens I wondered if it had been a good idea to turn up for the medical after all, I knew from the job application and the interview process that this post at the Academy would involve sexual situations, but there I was, not ten minutes after arriving being told to undress by my new boss who was barely half my age. AND M...

The Minister Ch. 02

by TheStarryEyedDreamer on Sep 14, 2017
Romance

Hi guys, this is the second chapter to The Minister. It probably won't make sense if you don't read the first one. It is slow moving and based more on the romantics. Sex won't come until a later chapter, for those of you looking for quick fixes. I am writing Chapter 3 now so hopefully it will be out soon! Please post comments and vote, let me know if you thi...