I just turned 18 but have been masturbating since I was 13. Around that time, my friend and I would masturbate together and we even sucked each other's cock off a couple of times. After that, he moved away, but I always masturbated for years afterwards thinking about his cock in my mouth. But don't get me wrong, I just love to be with girls. My high school girlfriend used to jack me off and blow me like there was no tomorrow and now as a freshman in college, all of those college girls are looking pretty good.
Lately I've developed this habit of riding around in my mom's SUV and masturbating while I drive around checking out the hookers. Because it's high up, most people passing by in other cars wouldn't be able to see me playing with my cock, but if you were standing on the street you can get a pretty good look. I wear these lightweight black shorts with no inner lining and when I pull my shorts to one side and pull the other side up towards my waist, it almost looks like I'm not wearing anything except my t-shirt. Plus with the dark upholstery of the SUV, it's pretty easy to see my exposed cock and legs and me jacking off.
I used cruise around the part of town that has a number of hookers, but lately there are less and less of them out and many of them are dressing down so as to not be as conspicuous to the police. Once I drove over to another part of town where there's mostly transsexuals working the streets and I was shocked to see what was going on over there. They weren't afraid to dress in really short, short skirts and small halter tops that I was it was awesome! I'd drive around and around checking them out, jacking my cock faster and faster but would wait until I got home to come. I didn't feel comfortable to let anyone see me jacking off so I covered up when they got too close. Then one night I was driving around and I spotted a new 'girl' standing on the corner by herself. Really cute, petite and slim. Couldn't have been over 16 and maybe even younger. As I passed, I noticed she had on a jacket but it was opened slightly and you could actually see a little of her breasts. My cock which had turned soft earlier sprung straight up and my hands started working my cock up and down. I whipped around the block and by the time I got back around, she had opened her jacket full on to let me look at her absolutely beautiful b-cup breasts and pink nipples. They were the perfect size for her small frame.
The stoplight was red and nobody was around so I pulled over and she came up to me on the driver's side (it was a one-way street). When she saw my hard cock and my hand down there, she was surprised and then smiled and asked if she could be of any assistance. Without hesitation, she reached in and pulled at the head of my cock a couple of times lightly just to tease me, but that's all that took. She didn't realize how hot I had gotten myself as I had been masturbating for about 40 minutes or so before that. I blew my load and so I jacked myself off right in front of her and some of it landed on her hand, but most of it landed on my steering wheel, dashboard and myself. She just giggled and said, 'Well, I guess there's always tomorrow'
When tomorrow came, I was really excited about seeing if I could find this her again but OH SHIT! My mom had to go out with my dad so I had to take my car instead. That night, I went out dressed in my usual shorts and after driving around about 10 minutes or so, there she was! This time she was wearing a small mini halter top and a very short skirt. It showed off her beautiful slim legs with her high heels on. When I pulled up, she was happy to see me again. When she saw that I had my cock out, she asked if I wanted some help with that and I told her that YES, I made sure I didn't get myself too worked up for her.
Then she asked me if I knew she was a 'girl with something extra' and I nodded yes. Then she turned her head, looking to see if there was anyone around, and then lifted her short skirt to reveal her hard cock pointing me straight in my face. She was completely hairless, smooth skin and circumcised like myself. She moved herself closer to the car and I greedily engulfed her 6' rod. This time, she must have been playing with her cock before I got there and what was probably less than a minute or two, she shot her load into my mouth. I was so horny after that! She jumped into my car and then we parked nearby and she gave me one of the best blowjobs I've ever had from anyone. even better than my former girlfriend! By the time I had finished, her cock got hard again and she wanted me to masturbate her so she put some lube on her dick and I slowly stroked her, playing with her balls every so often and used my finger to rub the outside of her butt hole and I sucked on her small breasts. It didn't take long and she came again.
I saw her a few more times but then she was gone. I'm guessing she only worked a short time to make some money and perhaps she was still in high school. I keep going out regularly to see if I can find her again, but lately its back to me jacking off in the car or my mom's SUV, just cruising around.