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. I glanced at the clock and it was 11:30 and I still had lots to do before Dane showed up. Fortunately my wig cooperated and fell into place without much work. My favorite wig is reddish brown with blond highlights and its full and long, down to my shoulders with sexy bangs. Even I was amazed at just how fuckin sexy I looked in the mirror, and I couldn’t wait to see Danes reaction. I had another vodka (my 3 rd or 4 th I think) and put on a white silky shirt that showed some nice cleavage and a tight black mini skirt and finished with my 5” patent leather high heels. At right around noon and 15 minutes from Danes arrival I put on silver heart earrings, silver necklace and bracelet and a cute silver ankle bracelet. A splash of perfume in all the right spots and I was ready for loverboy… Just as I walked out of the bathroom the doorbell rang! My heart was beating out of my chest as I walked through the foyer with that sexy sound of high heels on tile and I peeked through the peep hole. There was loverboy, all smiles with a bottle of champagne in his hands. I took one last look in the mirror and smiled at myself and opened the door just a crack and said “Sure your ready for this honey” “You bet I am baby.” Was his reply. I opened the door and hid behind it as Dane walked in then I held out my arms to my side and said “So, what do you think?” I love that look I get. He almost couldn’t say anything at first than managed a “Gawd damn Lisa, you look fantastic!” LOL We hugged and he kissed my neck and I felt a little rush when he did so, then he handed me the champagne. We chatted a few minutes and I could tell he was smitten with me and I had to fight the urge to suck his cock right there in the foyer! He followed me to the kitchen and he said he loved my ass in my skirt and I said I hoped he liked it out of my skirt too! He opened the champagne and poured us both a tall glass that we sucked down pretty quickly; poured another then I led him to the couch in the living room. We chit-chatted a little in between his compliments and it wasn’t long before Dane had his had on my thigh feeling my stocking tops. It felt so delicious so I just closed my eyes and softly moaned. “What do you want to do, baby? he asked. “I want you to take me anyway you want Dane honey” I whispered. “Suck my cock” he hissed. Dane stood up and dropped his pants and sat back down. I knelt between his legs and reached for my purse as he watched me apply a coat of lipstick. “Oh shiiitttt” he moaned as I leaned down and took his cock between my red lips. His uncircumcised cock felt so different than any cock I had before and I pulled the hood over the end of his cock and swirled my tongue underneath it. I sucked and played with it for a good 15 minutes as he squirmed. “Am I your little whore, baby? “Fuck baby you are the best fucking whore in the world.” “Will your little whores ass baby?” “Oh yes baby I want to fuck that sweet ass.” I stood up and dropped my skirt and led Dane to the floor. “Lay down baby” I said, and I grabbed my purse and squirted some baby oil all over his cock than put some on my ass hole, slipping my finger inside, the I straddled him and guided his cock to the little hole. Dane pushed up as I slid down all the way until his cock was all the way inside. “Gawd baby its so nice and tight.” I rocked back and forth and he felt so nice in me. We fucked like this for a while then he turned me over on my back, propped a pillow from the couch under my ass and entered me again and fucked me good! It was intense to say the least and my cock was hard and rubbing against his stomach with every thrust. Dane grunted and moaned and fucked me harder until he shot his load in my ass, causing me to cum too! He pulled out with an audible plop, followed by a stream of cum that ran down my crack. He got up and I laid there with my head spinning and feeling so fulfilled. I love making a guy cum like that! As is most always the case, the guy splits pretty quick after fucking and Dane was no exception, and that’s OK with me because I was already looking forward to my next conquest... Stay tuned for part two!
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