When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....

Added 15 Aug 2009 | Category Crossdressing | Votes 61 | Avg Score 4.87 | Views 14,099 | 15 Comments

   I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.    At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At...

Added 10 Aug 2009 | Category Crossdressing | Votes 45 | Avg Score 4.73 | Views 18,031 | 9 Comments

It’s been some time since I wrote about my crazy life as a slutty crossdresser so with some free time right now I thought I might tell you about Ricky, one of my early boyfriends when I was a teenager….   Ricky moved into our neighborhood when I was 17 and he was 18 and I had a crush on him right away. He was so damn good looking with dark brown hair, brown eyes and strong...

Added 24 Jul 2009 | Category Crossdressing | Votes 35 | Avg Score 4.48 | Views 13,157 | 9 Comments

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident.   I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt...

Added 18 May 2009 | Category Crossdressing | Votes 97 | Avg Score 4.71 | Views 15,195 | 13 Comments

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I...

Added 22 Apr 2009 | Category Crossdressing | Votes 23 | Avg Score 4.90 | Views 20,023 | 8 Comments

    I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it!   I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I...

Added 20 Apr 2009 | Category Crossdressing | Votes 14 | Avg Score 4.71 | Views 10,095 | 11 Comments