Disclaimer: This is a work of fiction. In real life, I do not recommend sex with streetwalkers.
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I always used to keep an eye out for hookers, not because I had some odd quirk about them, but because there was no beating around the bush, if you'll pardon the expression, about sex. Negotiate, pay, and fuck. No complications, no hassles.
Anyway, there was a hooker I used to see on a semi-regular basis who went by the name of Rose. Rose was about 5'2" tall, probably weighed about 95 pounds. She had black hair and dark eyes, small, well-shaped tits, and a small, round, gorgeous ass that was made to be fucked.
Anyway, I liked to see Rose because she was willing to take it up the ass (something most hookers wouldn't go for), and seemed to like it. (She sure made a lot of noise when I was pounding her ass, anyway.) I'd fucked a lot of hookers up the ass, and they usually charged $40 or more. With Rose, it was $30. I usually gave her $50, and she'd blow me till I came in her mouth, then I'd do her in the ass. Here's a sample encounter:
I decided one Saturday night about 7 pm that I needed to get laid, so I took a quick shower, got dressed, and hopped on my bike. It's about 12-13 miles from my apartment to the part of town where most of the hookers hung out, and it gave me time to plan what I wanted to do. There were three main areas to cruise for hookers, all in the same general region. It was just after pay-day, and I decided to pick up a hooker, fuck her, then find another and do it again.
Rose hung out on Buckeye, usually between 31st and 35th. She always wore a shirt tied up under her tits and a pair of tight shorts that really showed off her ass. I saw her on a corner, pulled up next to her and she hopped on behind. We went to the same place we usually did, a dirt road behind a junkyard. After I parked, we talked a bit, then she asked me, "What are you looking for tonight?"
I said, "I've got $20, how about a blowjob?" She said "OK," and I gave her the money.
Then I dropped my pants and leaned back against the bike. She knelt in front of me, took my dick into her mouth, and stared giving me some real good head. It was a bit chilly out, and her hot mouth sliding up and down my cock felt great.
A few minutes later, I said something like "I can come up with another $30, if I can fuck you up the ass." She stopped sucking my dick for a minute and said "OK," then went back to bobbing her head up and down my dick. Like I said, it was real good head, and I blew my wad in a few minutes later.
We sat and talked for a few minutes, and she drank some Coke to get the taste of cum out of her mouth. After a few minutes, she asked if I was ready to go again, and I said sure, and got a tube of lube off the bike, which I carry for just this reason.
She knelt down in front of me again and sucked me until I got hard again. This didn't take long, because I was looking forward to fucking Rose's tight little ass hard and heavy. As soon as I was hard, she put a rubber on me, squeezed a good amount of lube into her hand, stroked it over my rubber-covered cock, then spread some over her asshole. There was enough light coming from the junkyard that I could see her working her fingers in and out of her ass, getting it ready for my meat. Then she leaned over the bike, reached back and spread her asscheeks, and said, "Let's go, babe." I came up behind her and started rubbing the head of my dick up and down her ass, looking for that hole. She grabbed my dick and placed the head right at her rear entrance and said, "Slide that thing in, right now. I want to feel your big, hard cock in my tight little asshole!" Can't argue with orders like that!
I slowly started pressing my dick into her asshole, but she had other ideas. She reared back under me, and rammed her ass all the way onto my cock in one motion. I grabbed her hips and started sliding my dick in and out of her rear passage, savoring how tight and hot it was. I looked down and I could see my cock disappearing into her ass. (I really liked what I was seeing, too!)
I reached underneath her and started rubbing her clit, and she really started to shimmy and shake and pant. She started to talk dirty to me, to tell me what her roomie does to her when they were alone. Probably just to get me excited enough to come sooner, but it sure did turn me on.
"My room mate likes to tie me face-down on the bed and shove a big vibrator up my cunt, one with a clit-tickler. While that's warming me up, she licks my asshole, then slowly eases a butt-plug into my ass. Then she makes me eat her pussy while the "toys" drive me out of my mind. When she thinks I'm hot enough, she straps on a big, soft dildo, and makes me suck her 'cock.' Then she pulls the butt-plug out of my ass and fucks me hard until we both come so much we can't move."
This sexual monologue turned me on so much that I couldn't hold back any longer, and shot my wad deep into Rose's tight ass. I came so hard my knees almost buckled.
As we were cleaning up, I asked Rose if she and her room mate ever 'dated' together. She said yes. I asked if her roommate liked to be fucked up the ass as much as she did, and she said "Jade, she's my room mate, she's the one who taught me to take it up the ass in the first place. She loves it."
"Rose, I'd like to 'date' you and Jade at the same time. Would the two of you stay the night for $150?"
"Yeah, for $150, we'd both stay the night."
"OK, I'll pick the two of you up tomorrow night at the same place at about 8. Tell Jade to bring her 'toys'."
We got together, and had one hell of a time. However, that's another story, for another time.