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 athletic body and fantasizing about his cock between my lips made me dizzy every time I saw him.
It was summertime and Ricky spent his time playing baseball at the park and I spent my time indoors dressing up in make-up and sexy skirts and high heels, only dreaming of my new loverboy. When we first met I was dressed in boy clothes and he was nice and friendly but I was so flustered I almost couldn’t think of a thing to say. Then the next time we saw each other I was in a skirt and tank top with a bra and make-up on. He was pretty cool about it and I didn’t seem surprised and I guessed he pegged me as gay or bi from the start. With that ice broken I started going to the park to watch him play his baseball games and cheer him on. At first he ignored me but one day we walked home together. I remember that I wore a red t shirt and white miniskirt and kitten heels. My hair was teased a bit and I had on several coats of mascara and red lipstick and looked a little trampy that day, just for Ricky. And he noticed. When we got to my house I invited him in and to my delight he accepted my invitation! We had a cold beer or two and he pulled out a joint that we passed between us and we had a nice long talk. He was curious about my orientation so I explained I was transgendered and he seemed pretty cool about it all and he asked a lot of questions. Ricky eventually asked if I ever had sex and when I told him yes and as a matter of fact I once blew Mr. Phillips, the science teacher at our school he was really surprised and got a big kick out of that. I asked him if he ever had sex and at first he said yes, then hesitated and said no, that he never has. I told him I couldn’t believe a good looking and sexy guy like him has never had sex! He looked embarrassed by so and I put my hand on his crotch and squeezed his half hard cock thru his flannel baseball pants and said we can fix that if he wanted to…..Ricky leaned forward and kissed me, tenderly and softly at first, then he pulled me close and kissed me hard, shoving his tongue down my throat. I had to push him away and ask him to slow down a little but it was useless. He was panting heavily and his cock was rock hard in his pants, so I quickly unbuckled him and out popped his cock ready for action! I went down on him and he pushed my head down and almost immediately shot a big load of his musky cum down my throat. Poor Ricky seemed dazed and confused but managed to say how awesome that felt before he quickly pulled up his pants and left. I know that guys often have that reaction after they cum so I understood although that does make a girl feel a bit used. I fixed my lipstick after Ricky left and had another beer and watched some TV since it was still several hours before Mom came home from work. (Mom knew I dressed as a girl of course but I usually keep it to a minimum when she is around.) About an hour later I heard the doorbell ring and looking thru the peephole I saw it was Ricky again. He apologized for his hasty exit, making up some silly excuse as to why he had to leave so quickly, and asked if I wanted to hang out together. I said sure and within just a few minutes we were making out again. This time he was more patient and I spent a good 20 minutes sucking his cock and licking his balls before he came in my mouth again. This time he stayed longer afterward and just before Mom came home I blew him for the third time. That night he called me on my cell phone and we talked for a hour or so with plans to hook up again tomorrow. The next day I awoke with my clitty-cock standing straight up in anticipation of Ricky’s visit and after a fine orgasm in the shower I dressed extra sexy for my new loverboy. I put on a vinyl miniskirt, white blouse, black stockings and high heel pumps for him along with eyeshadow, mascara and the red lipstick Ricky seems to like so much. I even painted my toes and nails a matching red then took a Xanax and a shot of tequila and had a beer as I waited patiently for his arrival at 11AM. I was super horny and buzzed when he arrived a little before 11 and by 11:15 that morning I was on my hands and knees as Ricky drilled my sweet ass. We spent the entire day doing all kinds of naughty things to each other, and within a week, Ricky went from a virgin to an experienced and kinky sex maniac! All summer we fucked but in the fall he went off to college and I had to find myself a new man to party with……but that’s another story!