Ok dear reader time to here my life story, well at least the good parts anyway. As a child I had a sleight build and a tad shorter my fellow male classmates, so as you may guess I got picked on.A lot, and just like that boy named Sue, I learned to protect myself. My Mother use to make cloths for my girl cousin and used me for the Modeling Dummy. I would tell her how much I hated that; the truth was I loved it. All my life I loved feminine things and the way they felt, but no one every caught me.
By the time I was 21 I was a very successful computer graphics designer during the day, however, there would be times that I would go to an upscale hotel and my alter ego Nikki would come out. By now Nikki could be more than just passable, she was Gorgeous, as Nikki I never went out dressed trashy. I loved walking down the street in summer in a silk dress and heals, all the time turning heads, in fact my biggest problems on those days were guys trying to pick me up. Don't get me wrong, I was curious, but I was also a coward, I had had sex with women, but it wasn't that good, or I wasn't that good.
Then one day I did the unthinkable. I had just bought Nikki a new outfit, wig makeup the whole enchilada and after transforming into her I didn't want to waste all the time to redress, go to a hotel, redress then go out on the town. So I went out from my condo as Nikki, my heart was racing a mile a minute as I headed for my car. I started to breathe again once I was safely on the road headed downtown. All went well that night, Nikki met some friends in a gay friendly restaurant and went to some local clubs and kicked up her heals. It was 1:00 am when I reached home just as I reached my door the jig was up. My neighbor Roger was taking out his garbage of all things. When he look at me my heart stopped I was busted six ways from Sunday. Roger smiled and said Hi, want maybe he didn't know it was me, maybe I was my twin Sister from Cucamonga. I said Hi back, trying not to panic, just then my world turned upside down. Still smiling he said, "You know I always wanted to meet someone like you. Would you like to go out sometime." OK hold steady girl, your knees are buckling, "Ah sure how about next Saturday night." My God, I just accepted a date from my neighbor, Roger, a man, and he knew I wasn't all that I appeared to be. He agreed that Saturday would be great and he would meet me at my favorite hotel at 7:00.
My head reeling I made it inside. My first though was.Damn, I need a new dress he has seen this one, well thank the Lord for on-line shopping with express delivery. I ordered a cute little back silk dress and some new lingerie, then I ordered a very sexy red silk dress and some more lingerie, oh and Nikki needed some new shoes too. Saturday rolled around and I headed for the hotel, wondering why I gave up drugs, right now I could use a joint or three. After settling in I took a nap, you see under stress I sleep, and just then I was very stressed. At 4:30 it was time for Nikki to get her act together. I set up my portable CD player and out on Nikki's favorite music. First a bubble bath and total shave, then new lingerie with forms to fill out what I didn't have, and some tucking of things I did have. It was a red dress night, but first the right makeup was necessary, not too much, and not too little. Makeup was an art and I was an artist, and Nikki was my canvas. Next came that eye popping red dress, and lastly a freshly styled black wig. Looking in the mirror I saw Nikki looking better then ever, and none too soon.
It was almost 7:00 so I picked up my purse and headed to the hotel bar. Jack was tending bar and knew my alter ego. When he walked over to me he asked me if I wanted my usual white wine, and I said yes. When I went to pay for my drink he said it was on him, that the way I was dressed made his day. I thanked him for the drink and the compliment, if he only knew, but then again maybe he did. As I was contemplating this Roger came in. As they say Out of the Frying Pan.Roger slid into the seat next to me and ordered a martini. Roger told me that I looked very beautiful tonight, I thanked him, trying my best not to tremble. Roger then told me he had made reservations at a near by restaurant, to my surprise it was one of my favorites. Then he told me that if I wanted to we could go to this very exclusive nightclub, I said I would love too but it was next to impossible to get in. He then took my hand and said that he could get us in. My God he is holding my hand, good thing you're sitting right now girl. We finished our drinks and went outside to the limo he had rented for the night that is correct dear reader he rented a limo.
We ate dinner and I must say I didn't eat like a pig for once, way too nervous for that and it is very unladylike to barf on the first date. We then went to the nightclub and went through the Velvet Rope, it seems that Dear Roger went to school with the owner and got him through several business classes. We were sat at our private table with champagne and lackeys running to and fro. It was all a bit much but I loved every minute of it. We danced and drank our Dom, met the owner who asked Roger how he got so lucky, I told him that I was the lucky one for meeting such a sweet guy. By the time we left I had got use to Roger touching me, no not in anyway a grope, he was a perfect gentlemen. When we got back to the limo and started back to the hotel Roger kissed me. My heart melted, my heart stopped, my blood pressure went through the roof. Nikki had never been kissed, but that was made up for in spades. When we got back to the hotel Roger walked me to my room, and kissed me again with the same result. He asked if he could come in, trembling I admitted that I have never been with a man. Sweet Roger admitted he had never been with anyone like me either. Oh God we are both First Timers, Whelp, In for a penny.. As I opened the door there were flowers and another bottle of Dom. Damn this boy goes all out, if he was out to impress me he did a Mother Beautiful job. He opened the champagne while I checked out the flowers. We kissed some more, and my head was spinning, and not just from the champagne. Before I knew it I was stroking his cock through his pants, now I was about to find out if I was or if I weren't, if you know what I mean. I clumsily unzipped his pants, Damn nails, after a little help I had IT in my hot little hand. Now at the time I wasn't much on the subject of the sizes of different males manhood, but it was impressive to this girl. I bent over and kissed his cock, it was like being hit with a bolt of lightening. I was really going to do it for real this time. I had tried dildos both orally and anally, and had fantasies, but this was the real thing. I began to lick his cock like some flesh ice cream cone, and then I put the head on my mouth and suck. I began to get into this more and more, I mean it was really turning me on. The kids who had called me a cocksucker at PS 438 were right after all, and to Hell with them all. Roger was now fucking my face as I sucked like a creature possessed by a demon. He came in my mouth and I swallowed every wonderful drop. He then lifted my face gently by the chin and kissed me. He then stood he up and announced it was my turn, I undid my red dress and let it fall to the floor before I knew it my meager (compared to Roger's) cock was being given the same treatment, that his has just been subjected to. Across the room I glanced into the mirror and could see the whole thing, and thought, Damn Slut, you should have brought a video camera. I came quickly, than announced that although a little late I should slip into something more comfortable and sauntered into the bathroom. I fixed my makeup, and put on a black floor-length see-through nightgown, and stepped back into the room. And yes my heart was still pounding a mile a minute. By the "Oh Wow" look in his eyes I knew that I had achieved my attended goal.
Now it was Roger's turn to be nervous, as he said, "I don't know if you want to, but I would like to go all the way with you." Well.This was just our first date, and what kind of a girl did he think I was anyway. I took wrapped my arms around him kissed him deeply as said, "yes but be gentle, I'm still a virgin." "I will try, but I have never don't this either."
We went over to the bed and now my nightgown joined that red dress on the floor, as well as a very expensive tailored suit. Gee there happened to be some lubricant in the nightstand just in case, well to be honest I had planned to fuck my self silly with a dildo that night never planning on go this far. The next thing I knew his cock was probing my ass. Then he began to penetrate me; the pain was almost unbearable at first, but so was the pleasure. Slowly at first, but very surely began to fuck me, the pain was replaced by a pleasure I had never known before. I began to moan and writhe like a madwoman in heat. I was being screwed, by a real man, and Nikki and I where not two people who lived in the same body we were one. And right now I was having the best sex of my life. I moaned things like "Oh, baby deeper" "Fuck me more" Oh yes.yes oh, God yes". Well I think I did, the world was spinning so fast it is hard to remember. My life was forever changed. This was more than any fantasy I had ever had, and when my Roger came inside me, Nikki became a Woman, and I no longer wished to be a full time man.
Roger and I became an "Item" after that fateful night. Roger lavished me with fantasy dates and I fulfilled his every fantasy. My spare bedroom became Nikki's Boudoir, and I didn't give a damn if anyone found out. Oh, I didn't flaunt it and become a "Flaming Queen". I was the same me I had always been but I didn't cringe with fear about being "Outted". Roger now picked me up at my front door, and I took the money I saved from paying for expensive hotel rooms and spent it on dresses, lingerie, and even some rather outrageous outfits for nights in Nikki's Boudoir, but my friend, that is a tale for another day.