I Guess You Always Wanted the Pretty Unattainable Mean Girl to Be Getting into Your Car for Sex

It's strange that I remember the first time, because it's been 15 years now and I really haven't thought about it in ages. Everyone in town knew where the main hooker drag was and my friends and I had driven by a few times and even hooted at the girls, but these girls seemed as unattainable as any others. These were beautiful girls, girls who looked like what I imagined strippers and dancers to look like, done up in the classic slutty boots, halter tops and other accoutrements of the classic hooker. We never stopped to ask how much they charged because we knew we couldn't afford it, and now that I think about it, I never saw someone pull over and pick a girl off, or drop one off. It was almost like they were advertising a service available elsewhere, and not really on offer themselves.

Once, years later when I was back in town visiting, I pulled over on a whim and asked how much. "$250 for a blow, $350 for a lay and $400 for a half and half." I naively asked what a half and half was and she curtly explained that it meant she started with a blow and then followed through with sex. Even the basics were out of my price range and I drove off. I never did pick up one of those goddesses, but in the long run it probably wasn't worth it.

I worked in a warehouse not more than a mile from the docks, and occasionally in the mornings I would notice used condoms in our parking lot or our loading dock. I asked my boss about it, and he said that at night there were lots of hookers in the area since it's all warehouses, no one really complains. He would just wash the condoms into the gutter, and said he really didn't care if they used the parking lot to turn tricks at night. Intrigued, I headed down there that night.

At first I couldn't find anyone, looking right around where I worked proved useless, but after driving around in circles for a while, I started noticing a couple of areas where girls would step out of shadows or alleyways as people drove by. They certainly didn't make too much of a show of themselves, but once you knew where to look, it seemed like there was a few dozen here and there. Some were old, fat, ugly or had that used up look that junkies get, but some just looked like normal girls. I think I cruised around there for a couple of nights before I finally got the nerve to stop for a girl.

Now, I was 19 at the time, and although I wasn't a virgin, I wasn't very experienced either, and I'd certainly never done anything like this. I wasn't ready in any sense of the word, I didn't have any cash on me, I was nervous and shaking a little and generally more committed to the voyeurism than I was to the act. Then I saw her.

She was not a goddess by any means, but she was really pretty. She had blonde hair, a nice figure with perky, medium sized breasts and was wearing a black cocktail dress. She actually looked a little out of place, a little less trampy than the other girls I'd seen that night.

I pulled over and asked how much. "$60 for a blow, $140 for sex." Get in, I told her. I had to go to the bank machine, but she didn't seem to mind. Up close she looked to me like a pretty girl from a small town, there was something fashionably dated about her hairstyle that made me think that. She didn't look like anyone I knew, but she had that look that a casting director would look for when casting a generic mean girl in high school. Pretty with just a hint of superiority seemed to be part of her natural look. There was something about that that I really liked, I guess you always wanted the pretty unattainable mean girl to be getting into your car for sex. I figured her to be maybe a couple of years older than me, but it could have just been her expression – jaded or a little hardened. I elected for blow job because it seemed like a better way to start and frankly, I really wanted a blow job.

She made me stop at a pay phone for a second, then we chit chatted as I looked for an ATM. She said she was from a small town not too far away and that she had a baby she was trying to support. She volunteered that she wasn't on drugs – I hadn't asked – and it occurred to me that I really didn't care if she was telling the truth. She was smiling when she told me these things, and I think it was obvious to her – by my age or by my demeanor – that I'd never done something like this before. I hit the bank machine, took out $80 and she directed me to a secluded spot where I pulled over. She wasn't rude, she had kind of a flirty way about her and she smiled a lot. I think she could tell I was nervous and she sort of took charge.

She told me to pull my pants down past my knees, I did. I was already hard and she started to put a condom on me. I realized suddenly that with a blow job, I wasn't going to get to see her naked, and suddenly that bothered me. "Wait, I want to play with your tits a little." She told me it would be an extra $40. I offered her the other $20 that I had and without a word she lowered the straps of her dress. I clearly remember her breasts, they were great. Perky, firm, not a hint of sag, big areolas with nipples the size of the tips of one of my fingers. I played with them a little, sucked on one, then the other and then let her get on with her work.

One note on the condom, when she took it out, and I realized that I was getting a blow job while wearing a condom, I didn't complain but I did feel a mix of relief and disappointment. I knew it wasn't going to be as nice as it would be without one, but at the same time, I knew it was as much for my protection as it was for hers.

I've always used condoms when with pros, with a few occasions where a girl surprised me taking my cock into her mouth. Even then, with what they call a bare back blow job, I've never been too comfortable with the idea. I don't want a disease, and if she takes care of herself, she's making it safer for me. Anyway…

She said one thing before going down on me. "Ya got a big dick. You should do porno movies." As she blew me I thought about that. Was that something that hookers were supposed to say? Was it true? I was pretty sure it wasn't. Anyway, in a couple of seconds it all became academic and I leaned back and let her do her work while I half heartedly fondled her breasts.

I didn't last long, she straightened herself out, took the condom off, wrapped it in a tissue and threw it out of the car. She offered me another tissue to wipe up, I did and drove her back to her spot. I cruised that area looking for her again, but never found her. Maybe she moved to a new area, maybe she quit or maybe something happened to her. I never even got a pretend name.