Please accept this artful, hand-crafted disclaimer: Sex with streetwalkers is an iffy proposition at any time, and unprotected sex with one (or more) is not a wise choice. Furthermore, a work of fiction, such as this one, is not necessarily the best guide to a fulfilling, upright and moral life.</straightface>
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One night, while stationed in Florida, I got horny and decided to go out, find a hooker and get my rocks off. Maybe two or three times, depending on circumstances. The closest place I'd found to pick up hookers was in Pensacola, about forty-five miles away. It was about an hour each way, but well worth the trip, as far as I was concerned.
Cruising down Cervantes Avenue in Pensacola, I saw a short black girl wearing spandex shorts and a tube-top standing on a street corner. I pulled up next to her with the window down, and she asked for a ride. I said OK, and she hopped in. I watched her as she walked around the front of the van, and I really liked what I saw. She was about 5'4" or so, slender, with big tits, a nice ass and an attractive face.
Once she was in the van and we were heading down the street, she introduced herself, "Hi, I'm Sharlee. You looking for a date tonight?"
"Yeah, could be. How about you?"
"Yeah, I'm looking for a date. You willing?"
"Okay, sounds good."
"What exactly you lookin' for?"
"I don't know, why don't you tell me what you like to do."
"It's $25 for head, a fuck for $30, or both for $40."
"Do you do Greek?"
"What's that?"
"Do you take it up the ass?"
"No, I don't do that, but my friend does. I could introduce you to her later."
"OK, how about some head?" She agreed, so I parked in an out-of-the-way spot. We crawled into the back, I gave her the money, then dropped my shorts and sat back. She knelt before me and proceeded to give me an excellent blowjob, drawing forth a gusher of hot, steaming cum in short order.
After I pulled up my shorts we drove around for a bit, looking for her friend. We finally found her as she was being dropped off at another corner. I got a good look at her as I pulled up next to her. She was also a black girl, taller then Sharlee, about 5'5" or 5'6", smaller tits, and looked older, maybe mid to late twenties.
Sharlee yelled out the window, "Hey, Honey, get your ass over here." The other black hooker sashayed her way over to the van, and Sharlee told her to hop in. We took off, and Sharlee said, "Honey, m'man here wants a real piece of ass, so I though of you," with a giggle. We hit another red light about then, Sharlee got out and Honey moved up front.
"So, you lookin' for a date, guy?" Honey asked as soon as she was in the front seat.
"Yeah, how about you?"
"Yeah, lookin' to date. Whatta you wanna do?"
"Well, why don't you tell me what you like to do, and we'll see what we can come up with."
"Okay, for twenty, I'll suck you off, or you can fuck me. Twenty-five for a suck and a fuck, and for thirty I'll suck you off, then I'll suck you hard again and you can fuck me. Forty bucks and I'll let you do me in the ass. Make it fifty, and you can do whatever you want for, oh, an hour."
"Sounds good. I'll go for the hour, for fifty. You got a place?"
"Yeah, but you probably don't wanna go there. How about over there?" she asked, pointing at a small, seedy hotel that advertised hourly rates. It was ten bucks for an hour, fifteen for two hours, and twenty bucks for three hours. I decided ten bucks was enough, since I'd only contracted for an hour with Honey.
When we got there, I led her to the bed, where we both undressed. She took my stiffening prick in her hand and asked me what I wanted to do first. I told her I wanted her to suck me till I was good and hard, then I wanted to fuck her up the ass. She agreed, so I sat down on the edge of the bed.
She knelt down before me and started sucking my cock. In less than a minute I was fully hard. She stopped sucking and asked, "How do you want me?"
I dug around in my pocket and pulled out the bottle of lube I'd taken out of the glove box a few minutes earlier and told her, "Rub some of this on your ass." While she was doing that, I put two pillows in the middle of the bed and told her that I wanted her belly down and ass up over the pillows.
After a couple of minutes, she said she was ready, so I took the bottle of lube from her and told her to go ahead and lay down. While she was getting into position, I squirted some of the gel into my hand and quickly rubbed it up and down the shaft of my cock.
Once she was lying down, ass up, I knelt between her legs and leaned forward, touching the head of my cock against her ass. I slid it up and down a little, smearing it around in the slippery gel around her asshole, then lining it up with her tight little pucker and pressing against her.
Her asshole resisted briefly, then eased open as my cock-head wedged its way in. I stopped there for a moment, looking down at my rigid shaft wedged between her dusky ass-cheeks, then slowly worked myself into her ass until I was stroking in and out full length.
While I was reaming her asshole, Honey was reaching underneath herself and rubbing her clit and talking dirty to me, saying things like, "Oh, yeah, baby, fuck my tight black ass with your big, hard white cock," and "Come on, baby, pump your hot, sticky cum into my ass." All this, and she was humping back at me as hard and fast as I was humping into her.
Even though I'd just been sucked off less than a half-hour earlier, it wasn't long until I was shuddering, grinding myself against Honey's ass and pumping a load of cum into her, just as she'd asked.
I didn't pull out of her ass when I finished, but just sort of laid there, her clutching sphincter keeping my cock hard. After a few minutes of catching my breath, I started to slowly hump her ass again. After a minute or so, I was slamming in and out of her ass again.
I'd just cum for the second time in less than a half-hour, so I was able to keep fucking Honey's ass for quite a while, at least ten or fifteen minutes before I came again. Once I came for the third time, I just collapsed on top of Honey and lay there, panting.
Finally, I pulled myself out of her tight ass with a pop and rolled over onto my back. Honey went into the bathroom. I heard running water for a few minutes, then she came back into the room with a warm, wet washcloth, which she used to wash my dick clean.
Once she had me clean, she sprawled out across my legs and started to slowly, gently suck my cock again. It took her a while, but she eventually had me hard. She kept sucking until I came again, clutching her head and fucking her mouth. Didn't cum much, not after already cumming three times earlier that night, but she swallowed what little bit dribbled out.
After that, my time was about up, so we got dressed, I took Honey back to the street corner I'd picked her up from and I went to get myself some coffee before heading home, mission accomplished.