It was the beginning of the summer vacation.. we all guys headed for the beach to party and get wasted!! I had my friend Jimmy sharing the room with me. I knew him from school days so we used to get along very well. Until one night we were getting ready for a party I just saw a stockings and a female inners in his package.And I was wondering if he had a missed it for his sister's. Then I casually asked him about it then he said he liked wearing female inners and other stuff. In the beginning I thought Jimmy was kidding as I was unaware of his other side.Then due to cops problem we were unable to party long and returned to our room. Then Jimmy just sat in front of the mirror and started to do makeup as I gazed at him from the bed half naked. He literally looked like a woman in his red panties n see through bra. I was a straight guy and had no such experience before but without my knowledge I had hard on and was excited. He just walked towards me and removed my pants and started to blow me and I just loved it. It was new and exciting. He was literally gaging on my cock and I wanted more. Then he said it was my turn.... So I went down and started to lick his balls and suck his black cock. Then he just spread his legs and started to finger his tight asshole. I just leaned back stroking my cock and watching him tease me. Then with out any hesitation I slid my cock into his lubed ass. I was hard as rock and I fucked him as hard as possible till I filled his ass with my cum. His cock was dripping with pre cum and was craving for more. Then he rolled me over and penetrated his hard black cock inside my virgin ass I moaned with pleasure and pain. Initially he went slow and easy but later we were in the depths of pleasure and lust and craving for more. I got my ass stretched to the possible extent. He came on my face and I was forced to swallow his cum... Which I did and loved it. Then I knew I was into something more exciting than just straight sex. Ever since then I have been having sex with a lot of crossdressers and enjoying my sex life.