Kasey Stories

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Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...

Kasey's Legs Ch. 09

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I went shoe shopping after work, feeling strangely comfortable walking into a shoe store and requesting to try on high heels. The woman working at the store paused for a moment, looked me up and down, and asked why kind of shoes I was looking for. My sneakers were incredibly loose on my feet, like I was a child wearing my father's shoes. When she measured m...

Kasey's Legs Ch. 08

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

For the rest of my day at work, after getting my face fucked by Ken, the president of Goodrich Logistics, in Mr. Jones' office, I kept to myself. The guys continued making remarks, gestures and references to the home movie I'd made. They'd all obviously seen the movie by that afternoon. I'd seen Steve in the break room with his laptop and other guys gather...

Kasey's Legs Ch. 07

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

Waking up the morning after making my movie, where I ended up getting fucked by seven men, I felt very groggy. I didn't remember getting into my bed, but there I was, completely naked and very sticky. I pulled off the blanket to see dried semen all over my chest, stomach and legs. "I need to take a shower," I told myself. My legs were stiff and hurt, so I...

Kasey's Legs Ch. 06

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

It was no more than fifteen minutes after I finished giving Steve head that Darcy came home. She looked happy to see me dressed and sent me to get her things out of the car. When I got back I told her about my time with Steve, including the plan to make a movie so Steve could get his money back from Bruce. "If you just want to make a movie, just make a movi...

Kasey's Legs Ch. 05

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I ended up feeling good after my big day of showing up for work in short shorts. I didn't really know what to expect when I left for work that morning, but I just didn't want to hide any longer. Guys had teased me and made jokes about me, but after I caught them wagering on whether or not I was a cocksucker I blew the biggest jerk working in the warehouse....

Kasey's Legs Ch. 04

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

It had been a very exciting weekend. I had gone down on three different men in one night. I had taken it up the ass for the very first time and achieved the most intense orgasm of my life in the process. I found out, and accepted, that my girlfriend was sleeping with other men because I was unable to satisfy her. I moved into my own bedroom in our apartmen...

Kasey's Legs Ch. 03

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I returned from my girls' night out with Darcy and Chrissy feeling completely exhausted. My mind was unable to focus on anything other than falling down and going to sleep. I didn't want to think about my experience, on my knees next to a dumpster behind a bar, giving head to two different men, both of whom I had just met. I just wanted to sleep. The part...

Kasey's Legs Ch. 02

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Darcy and I were having breakfast and talking about my first experience going down on a man. I had been dressed up in my sexiest girl clothes with my makeup and hair giving me an almost passable look. Darcy had brought me out to a club that hosted a "drag night" and I had been a hit. I kept explaining to men I was straight and I crossdressed f...

Kasey's Confession Ch. 05

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

My sleep that night was haunted by dreams of men in dark shadows hissing at me and jumping out with monstrous cocks as big as my arm. I woke up in a sweat, leaned over to see it was only four in the morning and tried to go back to sleep. When I finally got out of bed at eight o'clock my mouth was dry and filled with the taste of booze and salt water. I had...