I enjoy dressing like a chick. Skirts and bikinis feel so nice against my skin, especially my cock. It feels so nice to have a hard cock in tight clothes; it just feels natural to me.
Anyway, there was this kid in my grade who I had always had a crush on. Timmy Kidrol was his name. He was skinny and not very muscular, but was very athletic. He always wore lacrosse jerseys, and underneath that was a 6-pack. He always wore gym shorts, the loose fitting kind. I always wanted to get into them. I had masturbated to what was underneath those shorts many times, cumming into my shorts, skirts, and bikini bottoms. I wanted him, but I was almost sure I wouldn't ever have him.
The summer after my senior year, I was 18. Barely legal, I decided to take a trip down to Provincetown. Since nobody I knew would be there, it was the perfect place to dress up and enjoy the sites (by that I mean guys).
The 2nd night I was there, I went out in a denim short skirt, a girls American Eagle shirt, high heels, and both parts of a bikini, instead of wearing underwear and a bra. I also had on makeup and a blonde wig to look more feminine.
I was walking down the street when I saw Timmy on the other side of the street, walking by himself. I thought that was strange and wanted to see what he was up to. He was wearing an Abercrombie lacrosse jersey and black gym shorts. I walked up to him. 'Timmy', I said, 'What are you doing here?' Timmy looked up and saw me, and kinda laughingly said, 'Why are you dressed like that?' Remembering that I was dressed like a girl, I stuttered to try and get a sentence out. 'Don't worry, I like it', Timmy said to me. I could see a bulge out of his shorts.
We went back to my hotel room, and as soon as the door closed, we both began to make out, our tongue being intertwined with each other, our cocks rubbing up against each other. I felt the 6-pack underneath his jersey, and it made my cock a little bit harder. I took off the lax jersey, and he took off my shirt. Our hairless chests rubbed up against each other, and our cocks rode the others, with our hands on the other's ass.
I pulled down his shorts and his boxers, got on the ground and began to suck the 7 inch uncut cock. I felt his ball sack, which I could tell made his cock so much harder. I licked his cock and sucked it some more. As I began to suck harder, he came right in my mouth, his yummy juices going down my throat. I stood up and kissed him on the lips, and we both lied down on my bed.
I pulled down my skirt and bikini bottom and stuck my hard 6 inches into his asshole. I thrusted my cock in and out of his ass. 'Oh yea babe, make me pregnant', he said. He came up and we both kissed with my dick in his ass. I felt his chest and 6-pack while we kissed and it made me cum right in his ass.
After that, we both lied down and spent the night together. We kept each other warm and we both stayed together for the rest of the trip, and even came back together and still meet up every once in a while. He's still wicked cute.