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 least that’s what I thought at the time.) One of my best friends was a good looking guy named Ray. Ray lived next door to us since we were kids and is the same age as me so we grew up together. Ray was big and strong and cute as hell and I had a secret crush on him since 9 th grade. Ray was often the object of my fantasies when I dressed, but I as straight as an arrow and I was always afraid he would freak if he knew about Lisa. As much as I wanted to be with him I didn’t want to risk our friendship.
Entering my senior year of high school and dressing for several years already I was beginning to get a little more daring in my crossdressing. I hoped I could live full time or mostly so after graduation, and I went out to the mall a few times dressed as Lisa and I met maybe 10 or 12 guys on line that I hooked up with and blew so I was pretty confident about how great I looked as a slutty chick as well as my oral talents, judging by the compliments I always got. Ray had always jokingly called me his little fairy friend so he knew I was probably bi or gay or something but he always made sure I knew he wasn’t by telling me about all the girls he supposedly fucked and how horny he was for pussy all the time. I tried to think of how I might tell Ray about my little secret but just couldn’t get the nerve to say anything to him when one day the opportunity fell from the sky! A mutual friend of ours, Sandra, the rich bitch slut in town, invited us both to a Halloween party she was having, and right away I knew this was my chance. Ray gave me a ride home from school that day and we talked about what to wear to the party. He decided on dressing as a doctor, since he was starting pre med in the fall. I held my breath and I said that was perfect, and blurted out that I would go as a nurse. Ray gave me a funny look and said “Male or female nurse?” “Female of course, silly boy” I replied. “So you’re dressing as a girl? “Yeah, is that OK with you?” “I guess.” He said, than added “That, I have to see.” That night I went online and found a sexy nurses outfit at a costume shop and bought it along with a pair of white high heel platform peep toe pumps, white seamed stockings and a white lace garter belt. I already had a sexy white bra and panties! Those next few weeks I was a little nervous but excited to be dressed as a slutty nurse in public and in front of Ray and the other people at the party! I almost chickened out when the day finally arrived but I stuck to the plan and started getting dressed around 5. Ray was picking me up at 7:30 and I wanted to be sure and look extra special for my coming out to the world. Mom was aware of my crossdressing for some time and she was resigned to the fact that I was transgendered, so I told her all about my outfit for the party and she was only concerned for my safety. I assured her I would be with Ray and she was OK with it all. (She is so cool!) I took a hot bubble bath and shaved what little hair I had on my legs, underarms, and pubes….just in case, you know. I painted my toenails a pretty red then I dried my hair and set it in rollers as I applied my make up as perfectly as I could. I was going for almost a drag queen look since this was Halloween and so I lined my eyes with a black pencil and put on false lashes and followed with about twenty coats of black mascara and a silver and blue eye shadow. I lined my full lips with a dark red pencil then filled them in with a creamy red lipstick, then finished with a reddish brown blush on my cheeks. So far so good! I put on my panties, tucking under my throbbing little ‘clitty’ and put on my bra and felled the cups with my silicone breasts. (36D by the way!). I put on the garter belt and stockings getting the seams straight up the back of my legs. The nurses’ outfit was tight and short with a slit up one side that showed my lace stocking tops, and some naught cleavage in the front.
I was looking and feeling pretty fucking hot by now and couldn’t wait to see Ray’s reaction! I took out my rollers from my hair and teased it up nice and full and attached the little nurses cap with bobbi pins, put on my sexy heels and headed downstairs, sure to freak out my poor mom! “Oh my gawd Lenny!” she shrieked. “Relax mom, it’s a Halloween party” I said. “I don’t know what I am going to do with you sometimes.” “Relax mom, it’s just for fun” “Whatever” she replied, shaking her head. Just then I heard Ray honk his horn, signaling he was in the driveway so I said don’t wait up, grabbed my purse, and took one last look in the hall mirror. “Fuck me, do I look hot! I thought as I opened the door and went out to meet Ray. I did my best sexy walk down the drive and Ray got out and stared at me! “Holy shit Lenny!” “It’s Lisa tonight, and close your mouth Ray”, I laughed and said. “I sat down in the car and Ray did too, then he just stared at me. “What? I asked. “Fuck Lenny, I mean um Lisa, you look amazing!” “You look amazing too in your little doctors’ outfit too” “No, ummm Lisa, you look like a real girl, and a real sexy girl!” I reached over and rubbed his thigh, and cooed…”I am a real girl… just for tonight, Ray.” “You are going to blow everyone away looking like that!” Feeling naughty I replied, “I just want to blow you…….. away, Ray….” “Fucccck” he muttered Ray managed to back out of the driveway and I kept my hand planted on his thigh as we drove. At every chance he looked over at me and just shook his head. Then Ray reached over to the glove box and opened it, revealing a pint bottle of Jose Cuervo. “Help yourself if you want…Lisa” I reached in and twisted off the cap and took a swig, and handed it to Ray and he did the same, transferring some of my red lipstick to his lips. We passed it back and fourth a few times and I was soon feeling a warm tequila buzz. Poor Ray seemed mesmerized by me and kept glancing at me, as I moved my hand slowly over to his crotch area. “Pay attention to your driving big boy. I wouldn’t want to get in an accident dressed like this.” I said. We sat there in silence for a few long minutes then Ray finally spoke. “I’ve never asked you this Len…Lisa, but I always assumed you were gay or something. “Did you really? I replied. “Yes, and um, are you?” Ray said sheepishly. Now brazen by the nice tequila buzz…“Well, if you mean do I like to dress up like a slutty whore and suck on a great big hard dick, then the answer is fuck yes!” I said, even surprising myself. “Ohhh fucccck.” Ray murmured. Another long silence then Ray spoke again, “So this is not the first time you dressed up as a girl is it?” he asked. “No it’s not hon, I do it all the time” I replied with confidence. Another long silence…. “Well I like you like this Lisa, you are so different this way.” I laughed and moved my hand over his crotch and felt what I was hoping to feel…his cock was hard. Hard as a rock. “I can tell.” I said smiling as he turned and smiled back at me. About that time we pulled into the long circular drive at Sharon ’s place and Ray pulled over and parked on the gravel lot. I reached in my purse and reapplied my creamy red lipstick as Ray watched intently. “Um, I can’t go in just yet Lisa” he said. “Why not hon?” “Cause I have a huge boner in these scrubs is why!” “Well you have two choices honey, either settle down, or take it out and let me suck you.” “Oh gawd Lisa, I am a little confused right now.” “Well then settle down Ray.” I said. OK, just give me a few minutes.” I turned the mirror my way and put on another coat of mascara and powdered my nose as Ray watched. “That’s not helping Lisa.” “Come on, big boy, let’s go in and blow everyone away.” I said. OK, he said. Ray held me steady as I maneuvered over the uneven gravel in high heels and tipsy from the tequila. As we got to the door his hand slid down and caressed my ass just as the door opened…… (I will tell you all about the Halloween party in my next installment…..)
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