This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women with hard cocks got me every time. When I was a few years older I had a rather adventurous girlfriend. One time as she was sucking my cock, she slipped her finger up my ass and I absolutely loved it. From then on, every time I jerked off, there was a finger in my ass. As the years went on I acquired dildos and shemale porn. I loved looking at beautiful and hung girls, dildoing my ass and jerking off.
Many years later, tired of dealing with “real” girls, I found myself going online to a tranny chat room, hoping to meet up with a beautiful chick with a dick. I quickly realized that the men outnumbered the girls and lavished them with attention. Thinking that it would not matter who was “dirty” typing to me I set up an account as a tranny and added some pics of my ass and legs, freshly shaved and wearing an old girlfriends thong panties. I instantly started receiving compliments and flirts. It did not take long until I painted my toenails and acquired a pair of high heels. The second that I put on the high heels I was turned on. This led to me getting an entire sexy outfit, wig and wearing makeup when I chatted.
Eventually I was contacted by a guy who only lived about fifty miles away and I enjoyed chatting with him. One day he suggested that we meet. I thought in the worst - case scenario I would just leave. After describing the way that I would suck dick to so many men I had started fantasizing about giving a blow job and this might be my chance. I agreed to meet him at a motel halfway between our towns on the weekend.
I got there early to get ready. I had on a very tight black blouse that showed off my padded bra, a black mini skirt, five inch open toed heels and a long blonde wig.