(Author's note: This is one of those stories that pretty much wrote itself. I began with a basic premise, a fantasy, but as the characters developed, it turned into something more. Admittedly, it has a bit of a Deus ex Machina ending, but I hope you enjoy it.)
***
"Prostitutes are like a box of chocolates. You never know what you're gonna get."
Okay, so maybe that's paraphrasing Forrest Gump a little. But the adage works just as well.
By the age of thirty-five, I had pretty much given up on relationships. Engaged four times, and not one of them had worked out. I was out a good ten grand, all told, on engagement rings. Not that I was particularly materialistic, mind you; I mention the fiscal fact merely as an interesting sidenote.
Following my last breakup, I moved to a new city in the Southwest, taking a teaching position at a research one institute while earning my PhD in Anthropology. I wasn't being paid much, but I did not have to worry about tuition, and student loans gave me an extra three grand a semester to cover my bills and incidental costs. I rented a small apartment not far from campus, a cheap, one-bedroom efficiency. It wasn't much, barely enough room for me, but I did not seriously entertain the idea of bringing anyone over.
Truthfully, I was pretty disgusted with the whole prospect of relationships. I had tried and tried again, and was still nowhere. I remember thinking back to when I was seventeen and just starting college. I had dreams that, by the age of twenty-five, I would be well into a career in advertising, with a wonderful, loving, and sexually kinky wife, a kid or two . . . .
Now I was ten years past that mark, still single, no kids, making a grand a month while still in school. Advertising had lost its appeal; I was more interested in people. Not that I regretted my life or the choices I had made; I had spent years living in Europe and South America; I spoke half a dozen languages, seen sights and been places most people only read about in text books. I'd had an intellectually rich and adventurous life.
But as regards the Great American Dream . . . I was sorely lacking.
Anyway, this is an erotic story, and not a diatribe about my life. So let's get on with it.
My first experience with a prostitute had occurred while I was still with my fourth fiancé, Kim. She had been a busty, compact little redhead who had some intimacy issues, and while I had been willing to give her patience and time to crawl out of her shell, after a few years, I was getting pretty frustrated with having sex only once or twice a month.
One night, heading home from work (I had been a bartender at the time, while Kim, a few years younger, was getting her master's), I stopped at a light near the edge of downtown. I wasn't really paying much attention to my surroundings, but I had enough wit about me to notice a slim little brunette, wearing red stretch pants and a dark pink top, standing in the shadows of a closed-down store.
And she was looking right at me.
I guess I stared a little too long. She must have thought I had given her an invitation. Hell, maybe I had. She was skinny and lithe, her skin heavily freckled, the opposite of my cherubic, big-breasted, pale-skinned fiancé. Perhaps my subconscious found the contrast stimulating.
Next thing I knew, she was stepping out of the shadows, walking up to my car, and opening the passenger door. She got in, closed the door just as the light turned green. There was a strong, spicy aroma about her, some cheap but enticing perfume I had smelled often enough on undergraduate girls when I was in school.
She told me her name – I can't remember it now – and asked if I was a cop. When I said I wasn't, she slid her hand to my lap and groped me.
Boing
! It surprised me how hard I got, and how quickly. I had no illusions that this girl was anything other than a prostitute, and that, for the right price, she would do anything I wanted. And that fact seriously got my blood running.
She pulled down her top, invited me to touch her little tits to further prove I was not a cop. I remember that her nipples were really thick and stiff. Satisfied that she was not in danger of being arrested, she got down to business. She asked me what I liked.
"Well, I like getting my cock sucked," I said as I followed the girl's directions through a twisting maze of a low-income residential area. I saw no reason not to be direct with my words.
"I bet," she said, giving me a look and licking her lips.
"And I like eating pussy," I added.
Her eyes flashed. They were dark, maybe brown or a dark blue, I could not tell in the dim light. "Yeah?"
I smiled back. "Yeah."
She thought a moment. "Forty bucks," she said. "Is that cool? You do me, I do you."
I was feeling excited, aroused. This was
guaranteed
sex, I realized. No dinner, flowers, a movie, or little gifts. I didn't have to
try
to get her into bed. Just shell out a couple Jacksons, and she was my sexual plaything. Now I understood the appeal of prostitution.
I agreed, and we found a little place to park behind a low-rent apartment building. I gave the girl the money, and she immediately lifted her hips and shoved her stretch pants down to her ankles. She had a shaved pussy, I remember, a little dark stubble, but it was not unpleasant. She lifted her legs, let me get between them, and sighed and moaned as I ate her out. She tasted fairly sweet, a little too tangy and bitter; I figured she might have gotten fucked a couple times before I picked her up.
I wasn't sure if she really came or not, but after about ten or fifteen minutes, she pushed my head back and we switched positions. She pulled out my dick and started bobbing on it. She really wasn't all that good a cocksucker, but the eroticism of the situation – paying a hot little thing to suck my dick in my car in a public environment – soon had my balls boiling and pulling up. I jacked off into her mouth, and she dutifully sucked out every drop of semen I had to give. I reveled in the relatively novel sensation. Not even Kim let me ejaculate in her mouth.
The streetwalker turned to the passenger window, rolled it down, and spat out my cum. I heard it splatter wetly on the ground as I recovered. I remember seeing a little drop of sperm on her chin, and didn't tell her about it. She gave me a few minutes to recover, and we smoked casually before I started the car and took her back. She gave me a little kiss on the cheek and promised she would be at the same corner the following night.
I never saw her again, of course.
But I did see a cute little thing about two weeks later, smoking a cigarette in front of her motel room door. She was talking to some guy on a bicycle, who gave me a dirty look. I circled the block, came back. The bicycle dude was gone and the cutie eagerly hopped in my car. She told me she had two kids she had to feed and that was why she was a hooker. She barely looked old enough to have kids, but she assured me she was nineteen.
She let me lick and finger her – she tasted a lot sweeter and more fresh than the first girl – and sucked my dick with gusto. But she warned me not to unload in her mouth, or else she would throw up. She did, however, let me cum all over her face, and it was kind of hot to watch her wipe up my sperm with her fingers and flick it out the window.
I never saw her again, either.
I started feeling guilty about my little escapades. I liked to think I was devoted to my fiancé. For a while, I didn't even think about picking up a streetwalker, even though I saw them every night on my way home.
But after Kim hit me with the bombshell 'I think we should get separate apartments for a while,' I knew the end was nigh. Kim and I tried to 'date' for a few months, but it did not work out. Finally, I picked up a skinny little dyed blonde named Michelle and fucked the hell out of her in the front seat of my '69 Impala before unloading all over her little saggy tits. She kissed and licked my dick clean, something none of the other hookers did, and gave me her phone number.
And of course, I never saw her again. The number was to a Pizza Hut.
***
So, there I was, in a new town, starting over, and focusing on my life rather than pleasing someone else. Between my studies, the classes I taught, and other work I did for the university, I spent more than half my day in servitude to academia. I didn't have time for a woman even if I wanted to start dating again.
Still, a man's libido is a difficult thing to ignore . . . .
I discovered, quite by accident, that the same avenue upon which the university lay was the man boulevard for streetwalkers. Most were to be found about five miles to the east, but a few were bold enough to stalk the streets close to the university. I saw them now and then whenever I left my office in the Anthro building late at night, but I really didn't think anything of it.
Then came the night I met Gabi.
Some of the parking lots for the university lay really close to Central Avenue, the dividing line between the northern and southern parts of the city, and also the street along which hookers strutted their stuff. On one particular day, I had been forced to take a parking spot close to the street, which was a real pain in the ass. My first class was in a building a good five minutes away.
Following the classes I taught, and those I took, and my own research, it was almost midnight by the time I got out. Crickets and cicadas chirped and rattled noisily in the grass and trees as I headed to my car. Just as I reached it, I spied a slender form standing on the sidewalk. She had pale skin, dark hair slicked and tied back, and a round, sexy, Hispanic-featured face. She wore a tight, dark blue sweat suit top with a zipper down the front and the tightest, tiniest of shorts that let half her firm little ass cheeks hang out. Her little feet were encased in dirty white sneakers. She had nice legs, I noticed.
For a long moment, I stared at her over the hood of my car, admiring that perfect, round little ass. She was obviously young, but as for how young, I could not be sure.
"Hey!" I called.
She stiffened, looked around, then turned my way as I called to her again. Her face was shrouded in shadow, yet I could still make out wide, round eyes made bold by dark eye liner. She had a narrow mouth and a round button nose.
"Need a ride?" I asked, hoping she was what I thought she was.
The girl hesitated, looked around, then started up the short grassy slope toward me. She stopped about ten feet away, hands in her little pockets. She had tiny breasts, barely a handful, but her nipples were clearly stiff and poking through her top.
"Maybe," she said, shifting back and forth. "Where you going?"
I smiled warmly. "Wherever you need to go."
