Real imaginative title, this one. What can I say?
Disclaimer: This is a work of fiction. In real life, I, of course, would never break the law, by, say, utilizing the services of a prostitute. And while we're in real life, bare-back riding may be great at the rodeo, it's not such a great idea when riding a streetwalker.
* * *
I was driving through downtown Oklahoma City. In theory, I was heading home from visiting my brother, who was stationed at Tinker AFB, but actually, I was cruising for hookers. Fifteen years ago, visiting some friends of mine stationed there at that time, I'd been told this area of town was the best place to find hookers and I wanted to see if it was still true.
At the moment, I was slowly cruising down a street a block off the main drag. I'd found in several other cities that the action was often better a block or two back than right on the main drag.
Case in point: as I passed an alley, I saw a girl leaning against the side of a dumpster. She was short with big tits for her size, wearing black knee-length boots, a very short black skirt and a tight white halter-top. As best I could tell in the dim lighting in the alley, she had a fairly attractive face and a nice figure.
I saw that she was looking at me as intently as I was looking at her, and that she started to turn and walk toward the mouth of the alley, then I was past. I quickly made a left turn at the corner, then three more left turns around the block. When I got back around, she was standing next to the stop sign.
When I stopped, she waved at me and, when I waved back, asked if she could get a ride. I agreed, of course, and she hopped in. As she was getting in the van, her skirt rode high up her thighs, and I could tell that she shaved her pussy and wasn't wearing panties. She saw me looking at her crotch and smirked. "Like what you see, dude?" she asked.
I grinned back at her and said, "Yeah, looks pretty damned good to me." She got the rest of the way into the van and settled into the seat, but made no effort to pull her skirt down. "Hi, I'm Annie," she introduced herself.
I introduced myself in turn, and I'm sure the name I gave her was no more false than the name she'd given me.
"So, Tim, what are you up to tonight," she asked me.
"Well, I'm supposed to be heading home right now," I told her, "but I'm bored and now I'm just driving around, looking for something to do."
"You looking for some action?" she asked.
"What kind of action did you have in mind?" Sometimes, I enjoy the opening negotiations as much as the eventual sex.
She didn't say anything, just reached down and slid two fingers into her smooth-shaven pussy. Then she pulled them out and waved them under my nose. "This kind of action, silly. Wanna fuck?"
"OK, sounds good to me."
"One question, though," she said.
"What's that?"
"You're not a cop, are you?"
"No, I'm not. Are you?"
"No, and I'll prove it, too. Here, put your fingers here," she said, pointing to her pussy. We were at a stop light, so I was able to lean over and slide two fingers into her pussy. She was hot, wet and slippery, and pretty tight. She sighed, then said, "Now prove to me that you're not a cop."
I thought a second, then reached down and unzipped my pants. "Go ahead and reach inside and pull my cock out. That proof enough?"
She said, "Yeah, that'll do," then reached inside my open fly and fished my now-erect cock out into the open.
"What do you want to do?" she then asked.
"I don't know, why don't you tell me what you'll do?" I countered.
She laughed and said, "Hell, I'll do anything. I'll suck you off for twenty, or you can fuck me. For twenty-five, I'll suck you hard, then you can fuck me, and for thirty, I'll suck you off, then suck you hard again and then you can fuck me. Sound good? Anything else you'd like?"
"Do you do Greek?" I asked her.
"Greek? You mean up the ass? That's forty. Since it's a slow night, make it fifty and I'll suck you off, then you can fuck my ass. Sound good?" she replied.
"Sounds good to me. Do you have some place to park?"
"No, I got a hotel room not far from here. Wanna go there?"
I agreed, and a few minutes later she was locking the door behind us. I quickly looked around. It was a smallish room, but had two beds, both of which were mussed up, with a small bathroom on the side.
Annie saw me looking around and said, "I share the rent with three other girls, but they're all out working right now. If you wanted to, you might could share two or three of us later."
I told her that sounded like something I'd think about, then we got down to business. I gave Annie her fifty, then dropped my pants and sat down on the edge of one of the beds. Annie knelt in front of me, cupped my balls with one hand while gently stroking my cock with the other and said, "Damn, you've got a big fucking cock. You're going to have to slow and gentle or you're going to rip my ass apart." I knew that was pretty much standard hooker rap, intended to make the john more excited and come sooner, but it still worked. I liked hearing women say things like that. After all, what guy is going to object when a woman tells him he's got a big dick?
Then she bent her head forward, parted her lips and slowly took my cock into her mouth, lashing her tongue against the underside as she went. Annie didn't quite get the whole thing into her mouth, but only missed by an inch at most. She held that position for a few seconds, then began to bob her head, sliding her lips up and down my shaft. After every ten strokes or so, she'd pull back and swirl her tongue around the head and try and force the tip into the slit at the end before resuming her cock-sucking.
She started sucking faster and faster, and was soon burying her nose in my pubes. I couldn't hold back, and took her head in my hands and started to mouth-fuck her. She didn't resist, but quickly matched my rhythm. In no time, I hit my limit and came, erupting into her mouth. As soon as the first spurt hit, she pushed her mouth all the way down to the base of my cock and held it there, moving her head back and forth while I fired bolt after bolt of cum into her throat.
I could feel her swallowing it as fast as she could, and finally fell back onto the bed, temporarily exhausted from the strength of the orgasm she'd sucked from me.
Annie sat on the bed next to me, wiping a few dribbles of cum from her chin and lips, then licking her fingers clean. "Damn, guy, you almost drowned me with that load. Why didn't you tell me you were going to cum that much?" Without waiting for an answer, she got up, went to the tiny fridge in the corner of the room and got herself a Coke. A quick swig to rinse out her mouth, then she came back over and sat down next to me again.
My cock was sagging, and Annie said, "How about a little dildo show while you're waiting to get into my ass?" Without waiting for my answer, she dug into the nightstand drawer and pulled out a large, pink vibrator.
She deep-throated the vibrator, lavishing the same passion on it that she'd used on my cock moments before. Once she'd decided that it was wet and slippery enough, she leaned back, spread her legs wide and had the vibrator worked into her pussy in just three or four strokes.
After a minute or two of that, she reached back into the drawer and pulled out a small wand-style massage vibrator. She handed it to me and said, "You want to hold this on my clit?" Of course, I agreed, and Annie was grunting and moaning her way through a loud orgasm a minute or so later.
All this had my cock fairly stiff again, and once Annie put the vibrators away she handed me a bottle of lubricant and told me to pour some of it over her ass and finger it into her asshole.
The stuff was a thick gel, but incredibly slippery, whatever it was, and I was fucking two fingers into Annie's tight ass in no time. Of course, this had my cock rock-hard again.
Once Annie was satisfied with the lubricated state of her ass, she stood up, squirted some of the gel into her hand and gave me a quick handjob before getting on her hands and knees before me. She was still wearing her halter-top and had her skirt thrown up around her waist.
She said, "OK, get that monster cock of yours up my ass, but be slow about it. I don't want you ripping my asshole wide open." More hooker jive, but I took her at her word.
I knelt behind her, placed the tip of my cock against her puckered asshole and slowly pressed against her. Her ass resisted for a bit, bowing my cock a little, then it suddenly popped open and the first inch or so slid in, accompanied with a loud grunt from Annie. I held my position, pressing against her hard enough that her taut asshole couldn't squeeze me back out, but not advancing any.
After ten seconds or so, Annie said, "OK, keep going, but don't push too hard. I forgot what it felt like to have my asshole stretched this wide." Since that was just what I wanted to do, I started pressing against Annie again, until I was balls deep in her tight ass. I knew I wasn't the first guy to have my cock between her cheeks, but she was still good and tight and was putting out a good line of hooker jive.
"Oh, yeah, babe, that's it! Stuff my tight little ass full with your big, hard cock! I fucking love having a cock slamming in and out between my cheeks! Come on, pump my ass full of your hot, sticky cum!" And so on and so forth. I knew it was mostly just an act, meant to get me so turned on I'd cum sooner, but it still sounded good and I liked it.
I'd usually cum pretty soon in a tight ass like Annie's, but she'd just sucked me off, and I think her lube had some kind of desensitizer in it. Whatever the reason, I was able to keep fucking Annie's ass for over twenty minutes. In fact, before I came, I heard the door open and a black girl walked into the room.
When she saw us, she smirked and shut the door behind her. She asked, "Mind if I join in? Twenty bucks and I'll lick your balls while you're fucking her." I agreed and she slid under Annie, positioning herself in a 69. As promised, she started licking my balls and Annie's cunt while I slammed into Annie's ass with even more vigor than before. One of my fonder unfulfilled fantasies was to fuck one girl in the ass while she was 69ing another, and now it was happening.
I kept fucking Annie's tight, upturned ass for another five minutes or so, but the sound of the two hookers' moans, added to the feeling of Annie's asshole working around my intruding cock was enough to push me to the point I couldn't take it any more and I ground myself hard into Annie, mashing her pussy into the other hooker's face while I did just what she'd been urging me to do and pumped her tight ass full of my hot, sticky cum.
Once her clenching asshole had wrung the last drop of cum from my throbbing cock and I finally went soft enough for it to push me out, the two hookers led me into the bathroom where they took turns washing my cock clean with a wet, warm washcloth. They were trying to talk me into another go-around, but I was done for the night. I promised them that I'd look them up the next night, after I'd had a chance to catch my breath. I was lying, of course, because I'd be over three hundred miles away by then.
As I pulled out of the hotel parking lot and hit the street, I saw the door to Annie's hotel room fly open and the black hooker came running out. I kept going, but I knew what she wanted: I hadn't given her the twenty I'd promised, and I laughed all the way to the interstate.