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 do have the opportunity I tend to get pretty wild, like I did a few weeks ago….
My wife went off to visit her family back east for a week and I couldn’t wait to spend the entire week dressed and cruising for cock. I made tentative plans with a few guys and other trannies on the net and planned to go out to a tranny club here in town a few nights. I replenished my wardrobe with some sexy outfits, two pair of killer high heels, and assorted lipsticks, false lashes, and other make-up in anticipation of my big week.
I dropped my wife off early Friday morning and secretly wore a pair of red lace panties under my jeans and on an impulse stopped at an adult video place on the way home, just for kicks. I don’t know why I stopped there, it was only 7AM and there was only one other guy there but I bought some tokens and headed to the private booths in the back. As I stood looking at the various titles available in the booths he followed me back there and stood next to me obviously pretending to select a video. I smiled and nodded to him and he smiled back so I went into a private booth and sat down and left the door open just a little. I put in my tokens and immediately saw a buxom blonde sucking a big black dick and the stranger opened the door and entered the booth. Without a word between us he stood in front of me and I unbuckled his belt and dropped his pants and took his already hard cock in my mouth and sucked him. He held my head with his hands as I gave him a blow job and I am not sure who was enjoying it more. I was dizzy with excitement and it didn’t take very long before he groaned and shot a big load in my mouth. I sucked him dry then he pulled up his pants, said thank you, and left. I glanced at my watch and realized that my wife’s flight was just now boarding and I already had my first mouthful of musky cum…..hopefully a sign of a very fun week! I finished watching the video then drove home so very excited to transform into Lisa Lee, my slutty alter ego! I took a swig of vodka to rinse out my mouth and took a long hot shower and shaved my face and underarms and put on a bra and panties. I opened up my computer and contacted some of the people I had lined up for the week. Dane hit me up first and he was at work but said he could get away for a long lunch so we made a date to come over my place around 12:15 or so. We already had exchanged photos and he said I looked “so fuckin hot” and he was pretty cute too. He was in his late 30’s and shorter than me, (I am 5-11 tall without my 5” heels!!), and has a nice body and a real nice looking cock. It looked to be about 6” long with a big head on the end and its uncircumcised. (Never had one on those!) I logged out, poured myself a vodka and headed to the bathroom to transform into Lisa. I was so damn excited and I love making myself into Lisa. I put on my foundation and powder then a pretty shade of blue/grey eyeshadow and drew in my eyebrows. Next came lining my eyes with a black pencil, and I put on some long false lashes and several coats of mascara. My eyes looked terrific! I took a little break and finished my vodka and cherished the moment…nice buzz and on my way to becoming Lisa, a cool guy coming over soon and it was only 10:30 on the first day of “vacation”! I lit a cigarette (120’s of course) then headed back to the bathroom to finish my transformation. I couldn’t resist a few more coats of mascara then I put some blush on my cheekbones then I outlined my full lips with a dark red pencil and filled them in with a creamy red Chanel lipstick. Most everyone, including me thinks I have the sexiest lips and today they looked extra special, and made for cock sucking! Next I took off my bra and put on a black corset and put in my silicone boobies that look and feel so real. I put on black seemed stockings and hooked them to the garters on the corset then tucked my “clitty” into a pair of black panties.