So, this is it, I thought to myself. I had not told my wife of this plan, of course. It was not something that I cared to share with her. Then again, I didn't share much at all with her anymore, except for our last names. She had made it clear that she wanted nothing to do with my "kinky stuff". That included spanking her, tying her up, and generally having my way with her. She was much more conservative than I turned out to be. This wasn't my first time being unfaithful to her. I simply couldn't handle the kind of mundane sex life that we had. I was seriously thinking of leaving her.
All I knew was that I had to get this urge out of me. I had to act on it. The great thing about a prostitute was that it would be a straight-up deal. I would not have to go on a date or pretend to feel love that I didn't have; it would just be about lust and pleasure. I was tired of making promises to people that I couldn't or shouldn't keep. I didn't feel like more commitments. I just wanted more pleasure.
I didn't want to constantly have this need at work, for instance. Oh, sure, there were women at work, but they were married. Married women would be after replacing their husbands with new husbands. They would want a ring and a new marriage, which would be presumably happy enough to make leaving their husbands worth it. Besides, even if it was just a fling, an angry husband would be an enemy I didn't need. I had enough problems with my own spouse without adding someone else's.
That didn't change the fact that I had a strong impulse every time I saw my female colleagues to take them and bend them over their desks. I wanted to pull down their pants or hike up their skirts and spank them with my belt. I wanted to fuck them doggie-style in front of everyone. I wanted to fuck them in the ass. I wanted them to wait in a line to get screwed openly in the office. I wanted to make them all my slaves and sluts. I wanted to take them as roughly and forcefully as I wanted to plunder my own wife.
That wasn't all. I wanted to call their husbands up and fuck them in the ass in front of their wives. Yes, I was into guys, too. This night would presumably help with the women. The other side of my bisexuality would have to wait. The ravenous lust inside me demanded that I take some whore and use her as I pleased.
I looked around for the right girl at the corner. I had a specific type in mind for tonight. The other flavors could wait. I wanted a woman who had short brown hair, blue-grey eyes, and a little too much makeup. She had to be a little slender, but also a bit whiny. In other words, she had to remind me of my wife. That bitch deserved a good spanking and ass-fucking, and I was going to give it to her, even if only through a hooker who resembled her.
"Hello, there, Mister," the brunette that I had noticed before spoke to me. We had flirted before, without either of us acknowledging it. It was just a wink here or there, lips puckered out, and so forth, as I drove by with my wife. This time, however, I was not going to drive by.
"Hello, there. I think I've seen you here before. Guess I am safe to assume that you're not a vice cop, right?" I probed a bit.
"Me, a cop? I wish! Then I'd get to hang around big, buff men all day long, instead of uptight store clerks! Hell, even you are a nice break, though you're not that tall," she grinned at me with a look of poorly disguised desire.
"How much for 'the works'?" I asked her abruptly, a bit irked at her comment on my relative shortness. I would remind her later that height wasn't the measurement that counted.
"You mean 'nothing off limits'? No holes barred?" she teased, making it more apparent that this was a rare case of mixing business with pleasure.
"Exactly, missy," I confirmed it.
"That would be a full hundred. The complete package doesn't come cheap, sweetie. I charge top dollar. Believe me, however, when I say that I am worth it. I'd be worth it even if I gave you an STD, which I don't have. I get tested often for HIV and other diseases. Only select customers get it 'bareback', so I am not likely to catch anything. You'd be such a client, since you're clean and want the 'whole package'. Not even the hundred bucks get you 'bareback' by themselves. I have to trust that you won't infect me. I may be a street hooker, but you're not slumming when you fuck me," she made her pitch for the price that she wanted.
Clearly, she either saw her chance for the Benjamin and was determined to seize it, or she just really found me attractive and my interest flattering. Maybe it was both. Being a cynic, of course, I was betting on the first one.
As we were in my truck by now, I wasn't worried about people overhearing us. I also didn't give a damn about anyone finding out. My wife's word about it would be hearsay, nothing more. The only way that I could get in trouble now was a sting. I didn't care if my wife left me over it. I was already on the verge of filing for divorce for irreconcilable differences. After only 6 years of marriage, I was fed up with her attitude. So, let the bitch complain! My best friend from college was a lawyer with plenty of cash. He'd defend me pro bono, if necessary. Since Nancy always avoided sex during her fertile days, to push her career forward, we had no kids.
I decided that I deserved a chance for some wild sex with someone who appeared to actually enjoy it. I was going to go for it. Yes, the girl in question might be a bit shocked by the kinky side to me, but she was charging major bucks for a street whore. That being the case, she shouldn't have a problem with something that she had probably seen before. If she hadn't, she was about to experience it. I wanted a good, nasty "grudge fuck", with a side of handcuffs and a paddle. With any luck, we should both have fun. She seemed like a pro who was into the job for more than just cold cash. That in itself was refreshing. If she didn't bolt when I brought out my toys, everything would be fantastic.
"It's a deal. Now, my wife is out of town on a business trip for her company. I couldn't go with her, as my job precludes it. What do you say we come back to my place? It would be nicer than a cheap motel," I suggested.
"Works for me," she agreed, not a bit perturbed at my marital status. I was hardly the first married man to patronize her business.
We finished driving and arrived at my house. It was late enough that I had already given my wife her "goodnight" call from our home phone and she was probably sleeping like the dead. Few if any people would be up, so the chance of any witnesses was decreased. I had planned this well ahead, and with plenty of attention to detail. Being a private detective, I knew how to avoid being caught by one.
When we got inside the house, I told the girl to close her eyes. She did as I instructed. I then put a blindfold on her and led her into the bedroom. Once she was relaxed, I told her to lie back on the bed. When she complied, I handcuffed her, and I could tell that she was panicking for a second. She might well have thought that I was a cop, or a serial killer, at this point. When I hiked up her miniskirt and removed her panties, I could hear her breathing normalize, as if reassured that I was truly interested in sex. Since she was on her back, and I wanted to paddle her, I simply turned her over onto her stomach.
She tensed up and flinched for a second when I gave her the first swat, but she didn't ask me to stop. Evidently, she accepted this as part of the bargain. It was a shock to her, but not one so unpleasant as to warrant breaking our deal. I struck her again with the paddle. She jumped once more, but this time less dramatically. She was now more prepared for the blow, after all. She anticipated being paddled, and had begun to adjust to the pain.
While I gave her the next 18 swats, she seemed to squirm and wince a bit, but she didn't cry or complain about it. She made no verbal protest at all. Her bottom was a little red, but she wasn't bruised or anything. She lay there on her belly, waiting for the next swat. When it didn't come, she took some initiative and altered her position slightly, lifting her ass up into the air. It faced me, as if she was inviting me to do something else to her butt and get my money's worth. She obviously still wanted to continue the transaction.
When I spread her cheeks, I realized that her butt-crack was shaved, just like her cunt. It was also very clean, far more than one expected from a streetwalker's asshole. She clearly made a point of good hygiene and safety. It was part of the unusual pride that she took in her profession. I began licking her sphincter and pussy, moving across the taint back and forth. I wanted to see her reaction. My instincts were right: she loved this act, and almost certainly kept her tush clean with the idea of encouraging men to rim her ass.
I started to nibble on her lips and clit, just long enough to tantalize her with the idea of a climax. I moved my tongue between her holes repeatedly for the next few minutes, which caused a wetness that I could smell if I lived halfway across the world. It wasn't a bad scent, unlike what some men consider it. To me, the aroma was a delectable one. It was the smell of arousal, after all. It reminded me of sex, pleasure, and orgasm, including hers. Yes, I wanted her to cum too, but I definitely wanted to play rough before making her do so. I wanted the realization of one of my fantasies that Nancy had rejected: a wild, kinky night where I would reward a good slut or slave for servicing me well.
I replaced my mouth and teeth with my fingers on the hooker's clit, and then I guided my cock into her now damp pussy. I wasn't gentle, of course. I slammed my dick deep into that girl's sex, making her gasp at how forceful I had become after being tender for a moment. My hard cock rammed her cunt, which was now dripping her juices onto my marriage bed. That in itself excited both of us more. While I knew that I would have to wash the bed sheets afterward, the fact that I was fucking a girl and making her drip her fluids onto that bed was a thrill for me, and apparently for the whore as well.
As my wife had rarely climaxed and never squirted during our marriage (not my fault, since I definitely made an effort), it aroused me a great deal to succeed with a presumably jaded hooker where I had failed with my own spouse. This wasn't an act. She was drenched! She had enjoyed everything from the bondage (which was still technically happening, since I hadn't removed the cuffs) to the paddling, from the rimming to the grudge fucking. As I pounded her soaking twat, I began to finger the outside of her sphincter and kept playing with her clit. I then switched to swatting her again, which caused her to jerk and flinch for a second, although this time in response to my hand.
My hand felt the completion of her climax, as she tensed up and dripped onto it. She wasn't gushing, at least not yet, but she was very wet. She began to milk me with her cunt, and I felt her gush on me as she moaned her orgasm. Since she was a whore, it had probably happened to her now and then, but she acted as if were a truly rare event. She seemed stunned that my hand, still stinging her bottom with a spanking, would help get her off like that. I got the impression that she had realized something about herself that had never occurred to her, despite all of her sexual experience. She was a masochist, and quite possibly a sub or switch.
Before she could make me cum in her sex, I pulled my cock from her now relaxed pussy and applied some lube that I had put out for my next act. I removed my other hand from her clit and stroked myself to keep hard in between penetrations. After lubing up her asshole, I then put some of the warming liquid on my cock. It was extremely sensual, but it hadn't been used much, since Nancy refused to do anal and didn't like anything but standard lubricants.
When I entered the whore's ass, she flinched very slightly, and then started thrusting back at me. She apparently wanted me to cum inside her soon, for one reason or another. I resumed spanking her butt and masturbating her clit, which caused her to drip some more. Even though we hadn't said much, she understood what I was doing now. I wanted to cum in her asshole and possibly get her off that way as well. I showed her zero mercy at this point, going for the final release with gusto. As I shoved my dick in and out of her bowels, she grunted a little, but she relaxed again when I started spanking her left cheek softly. As I didn't stop swatting her right cheek, her entire bottom was now some shade of pink or red.
I had taken a calculated risk that ending my manipulation of her clit to swat her derriere would distract her from the pain in her ass. It worked very well, as the hooker seemed to completely surrender to the invasion of her backdoor and my apparent dominance over her. I had achieved an unexpected level of mastery of this young woman, without planning for more than a vent of my frustrated kinks. She wasn't just doing this for the money anymore. She was also doing it for pleasure.
When she began gushing and thrashing from my cock in her sphincter, I couldn't resist cumming at last. I was frankly pleased with myself for lasting a full half hour under these circumstances. Then again, it was probably the act of pulling out from her cunt for a bit there that helped me do that. Otherwise, I would have cum already. Well, it was that and her relaxing right after she climaxed. Any more milking, and I would have expended my seed in her pussy.
As I removed my softening dick from the whore's ass and went to the bathroom to clean up, I saw her in the mirror next to me. She had a very satisfied smile on her face, confirming my earlier suspicion. She was still wearing the cuffs, as I had not removed them. The blindfold was gone, however, since I had taken it off her face right after I came in her.
"The keys to the cuffs are on the nightstand, missy, if that's what you're wanting. I'll pay you in a second too," I informed her as I followed up my cleaning of my cock by pissing. That was a precaution I always took after unprotected sex, especially anal.
"Thank you, but I was actually wondering just how long your wife's business trip is, sweetie," she grinned.
"2 more days, but I can't spare that much cash! I wish I could. It would be a great weekend otherwise. I'll just have to settle for beer and cold showers until Monday. Hell, unless I can get a friend with benefits or two on the side, I might well have to settle for that after Monday too! Too bad, because you really seem to be as kinky as me," I reacted to her question.
"Your wife doesn't fuck you very well or often, does she? Yeah, you seem more the disgruntled hubby type than the sort who would cheat just because he could. To be honest, though, that's just a convenient fact for me. I would find any excuse to fuck you, whether or not you were justified for stepping out on the missus. I want you, at least sexually. I want to fuck you for the sake of the kind of sex that we just had. Screw the money. You're a frustrated, but basically aggressive man. I'm apparently more repressed than I thought, since I like having a man spank me. The 'grudge fuck' was great too.
"What really surprised me was how much I liked obeying you and letting you handcuff me. You were in charge, and that was a welcome change from my usual clients. Like I said, most of them are nerds and losers. Few of them have any balls. They just let me dictate the whole routine. That gets old. Now I know why. I wanted a real man, and I haven't had that pleasure in months. So, sweetie, what do you say about making this a weekend fling, after all? I'll do whatever you like," she declared, indicating that she was even more into me than I thought.
"Very well, if you'll agree to follow my rules and not charge me for this weekend, you can stay until late Sunday night. That's when it will be safest for me to drop you off at your place, assuming that you want to return home for the night," I accepted her offer.
"Sure. I will need the break, from the sound of it. I expect to be worn out from our little experience, if tonight is you at full potential. What sort of rules?" she winked at me, making it clear that she particularly wanted to do this.
"Well, to begin with, you have to call me 'Sir'," I announced.
"Yes, Sir," she answered seductively.
"For another, I want to know your name," I demanded.
"Valerie, Sir. Please don't call me that, though. I much prefer what you have called me," she pleaded.
"Missy, you mean?" I asked.
"Yes, I like the way that you say it, Sir," she explained.
I chuckled and gave her a very intense French kiss, as I realized just how lucky I had gotten tonight. It might be a fling, but it was one that would change both of us for life, and it was a change that I would embrace with enthusiasm.