Disclaimer: fantasy, this is. For reality, mistake it not. Have sex you should not, with people you know do not. Have sex especially, you should not, with hookers.</yoda>
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Travelling though the Midwest late one night, I decided to stop in Kansas City and try and find myself a hooker. I had no idea where KC hookers hung out, but I knew they had to be somewhere.
Just after making my decision, I saw an exit sign for "Prospect Avenue". For no particular reason, I decided to take this exit and see what there was to see. Check out the "prospects" on Prospect, so to speak. I got off the interstate and turned north. About five blocks or so, the street teed east and west, and I turned east.
A block farther, at the next corner, I saw what I thought was a hooker. In my experience, if you see a black woman out after midnight in a seedy area, by herself, standing on a street corner, wearing cowboy boots, daisy-dukes and a halter top, odds are she's a hooker. She waved at me as I went by, so I went down two more blocks, then turned. I turned again, and headed back. There was a stop sign on the corner of the street she'd been on, and as I stopped, I looked around the corner and saw her walking my way. She waved at me, and I waved back. She trotted up to the van, asked if I could give her a ride, and hopped in when I said "OK".
I got a better look at her as she came up to the van and got in, and I liked what I saw. She was rather tall, probably about 5'6", with big tits, long hair pulled back into a ponytail, and a fairly pretty face. She was definitely better looking than your average street whore.
I asked her, "Which way?" and she directed me back out onto Prospect, then right, and right again at the light.
While we were waiting for the light to change, we had the following dialog:
"Are you a cop?" she asked me.
"No, are you?"
"Not me. So, are you looking for a date?"
"Yep. Are you?" This last bit was a piece of meaningless verbal fencing. She'd asked if I was a cop, and if I was looking for a date, so she was almost certainly a prostitute. That, or an undercover cop. In that case, however, she probably wouldn't ask if I was a cop, not wanting to scare me off. In any event, if she was a hooker, she'd just let me know, and the next step would be to negotiate services and pricing.
The light changed and off we went. The initial contact having been made, the negotiations began.
"Yeah, I'm out looking for a date. What are you looking for?"
"Oh, I don't know. What do you like to do?" Now me, personally, I'm a little bit adverse to just blurting out what I want and what I'm willing to pay. Just a little bit more defense in the event she was a cop. Not much of a defense, but hey, better than nothing. That, and I like the negotiating.
"For twenty, I'll suck you off, or you can fuck me. Twenty-five for a suck & a fuck," she replied. "Or for forty, I'll suck you off, then suck you hard again and then you can fuck me."
"Do you do Greek?"
"Greek? What's that?"
"Anal. Do you take it up the ass?"
"Ooh, that's extra. I'd have to charge fifty for that, and you'd better have some kind of lube, 'cause you ain't fuckin' my ass dry."
I assured her that I had lube handy, and we settled on sixty, for which she would suck me off, then suck me hard again and let me fuck her up the ass.
The question then became one of place: where to do the dirty deed. We settled on doing it in the back of my van, and found a good place to park. Just to be on the safe side, we actually found two good places to park-one for the blow-job, and one for the ass-fucking.
The first spot was in the parking lot of a large 24-hour grocery store. I parked, we crawled in back, I handed her the twenty dollars for the blow-job, and dropped my pants around my knees.
She knelt on the floor in front of me and started sucking my cock. She did it slow and slobbery, drooling lots of warm spit up and down the shaft as she went, just the way I like it. It felt great, I was anticipating fucking her ass, and didn't take long at all before I came. She swallowed it all, then sucked a little bit longer to make sure she got every drop.
We drove around for a while, then settled on a second location, the parking lot of a large church. They were celebrating midnight mass or some such, and there were plenty of cars in the parking lot. I pulled into a spot toward the back, out of the way and out of most of the lights.
This time, once we were in the back, I pulled the curtains over the windows and across behind the front seats. I pulled off my shorts and shirt, and she took of her top and pulled her shorts down around her ankles.
I started getting hard, watching her bend over in the cramped space. Sitting back, she knelt in front of me again, put her lips around the head of my cock and slowly slid down the shaft until she had the head in the back of her throat and her nose was nestled in my pubic hair. She then slowly drew back, until once again just the head was between her lips.
Needless to say, I was hard almost instantly. She sat back and I handed her the lube, then watched her squirt some into her hand, smear it up and down the crack of her ass, then start working it into her ass. Once she had herself lubed to her satisfaction, she squirted a bit more on her hands and rubbed it over my cock, making it nice and slippery.
Once she was satisfied that my cock was lubed up enough, she bent over the back seat and said, "Do me, babe. Shove that big ol' cock of yours right up my tight little black ass."
I knelt behind her and aimed at my target: her puckered asshole. I touched the tip to her hole and slowly started pressing against her. Her ass resisted my intrusion at first, then slowly eased open as I increased my pressure against her. I slowly kept sliding deeper and deeper into her tight ass until I was balls-deep.
I held that position for a few seconds, then slowly eased back out of her ass until only the tip and first inch or so were in, then repeated the process. Each time I pulled out and slid back into her ass, she got a little looser and I moved just a little bit faster. Finally, after almost five minutes, I was fucking her ass about as fast as I'd ever fucked anyone up the ass and she was talking dirty to me, "Oh, yeah, baby, I just love having a nice, big, rock-hard cock sliding between my cheeks and ramming in and out of my tight little ass. C'mon, baby, why don't you pump a nice big load of cum up my ass? I know you want to! Ram your big, white cock up my tight black ass!"
Since I'd just blown a load of cum into her mouth not that long before, I was able to hammer at her ass for a while before I felt the warning signs in my cock and balls. I told her I was about to come, and she said, "Oh, yeah, baby, I want you to pump my tight black ass full of your hot sticky cum! Do it to me, baby!"
Instead of replying, I grabbed her hips harder, made about six more hard, deep strokes into her slippery ass and gave her exactly what she was asking for: a big load of cum as deep inside her ass as I could get it.
Once we both caught our breath, I pulled my still-erect cock out of her clenching asshole and sat back for a bit. I handed her some paper towels to wipe her ass clean of the slippery gel and used more to clean myself up some. After that, we both got dressed and I dropped her off on the street corner where I'd picked her up.
Then I went on my way, drained and feeling much happier. I was definitely going to remember the prospects on Prospect Avenue.