His breezy pre-sex conversing, combined with his sudden rugged manner with me during sex, made me see Mr Santos in a different light. He was a handsome man, I decided, as I watched him zip up his trousers and go off in search of the toilet. I still had my panties around my knees when he came back into the room. I was lingering in my little swoon.
“What’s with you?” he asked.
Snapping out of it and feeling embarrassed, I moved to pull up my panties.
“No, wait.” He stopped me. “Not yet. You feel like making a little extra money today?”
I was caught off guard. He fished out his wallet and surveyed its contents. “Well, I have ten whole dollars.” He found this amusing. “What do you feel like doing for ten dollars?”
“What did you have in mind?”
“I want to try something and see if I can make you come.”
I never, under any circumstances, came with a trick. But Mr Santos intrigued me. “You think you can make me come for ten dollars?”
“Ten bucks, and a nice dinner. What do you say to that? My wife’s out of town and I’ve got all the time in the world. I’ll make it up to you next time about the money. You know I’m good for it.”
I was feeling game. I liked Mr Santos. I wasn’t worried about the money.
He told me to step out of my panties completely, then to squat down on the parquet floor. He told me that under no circumstances should I touch myself; he wanted to do all the work. He lubed two of his fingers, squatted down next to me, held me around my shoulders to sort of brace me, and then he stuck the two lubed fingers up my ass. He wiggled them vigorously in there, pushing hard against my perineum, rubbing the wall of muscle with all his strength.
“Oh god,” I squealed in sheer ecstasy, clutching him tight, a stream of piss suddenly squirting out of me and forming a puddle on the nice wood floor.
“Go for it, baby. Let everything go. We can clean this up later. Bear down on me.”
I did as he suggested, pushing my asshole down around his hardworking fingers, never dreaming that I could be launched into orgasm like a rocket without direct pressure applied to my clit. But it happened. My thighs shook as I squatted and bore down, more fluids gushing out of my open pisshole. My body was overwhelmed by waves of pleasure as his fingers rubbed more vigorously against the pressure of my now frantically contracting sphincter.
When I was through hyperventilating and convulsing like a lunatic, Mr Santos was still holding me, smiling. “Did you come?” he asked, very pleased with himself.
I didn’t take the extra ten dollars that day, but I took him up on his offer to buy me dinner and that was the beginning of a new chapter in our “business relationship.”
He continued to pay me whenever we got together, but we talked more, he took more time with me, he felt challenged to give me orgasms in unexpected ways. Soon, he was paying for rooms in five-star hotels, where we’d disappear for entire days together, relying on room service for sustenance. He introduced blindfolds, light bondage, and spanking to the list of things we were now doing with each other regularly in a lavish king-sized bed.
“Do you ever eat pussy?” he asked me one afternoon. “I mean, do you ever get asked to do that when you’re out on a calls?”
I looked at him uneasily, not at all pleased that the world of my other tricks was even remotely entering into our time together.
“Do you even know how to eat pussy?”
“Of course I do.”
“You get paid to do that?”
“Sometimes.” I didn’t feel much like discussing it.
“I’d like to see you eat pussy, you know that?”
You and every other trick on earth, I told myself. The last thing I wanted was to bring another girl into our scene, a girl who might prove to be more novel than me, a girl who might walk off with his number in her purse and then I would lose my favorite trick. Mr Santos was now the man I fantasized about when I was home alone in bed. I didn’t think he would leave his wife for me, or anything like that, but I naively considered us lovers. I’d begun to hate the fact that he still paid me.
“What’s that face for?” he said. “You aren’t into pussy?”
“Girls are all right.”
“I was thinking more along the lines of a woman – not a girl.”
He immediately piqued my interest. “You mean you have someone in mind?”
“To be honest, there’s a woman I’ve been seeing off and on for years, since before I was married. Occasinally, we get together when our spouses are otherwise detained and we have sex. I told her about you. How much fun you are. How amenable you can be.”
And whose idea was it to make it a threesome, I wondered suspiciously, hers, or his?
“She’ll pay you the same amount I do; you’ll get double your usual fee. It wouldn’t be a question of taking advantage. I would really like to see you eat her pussy. And I think she has an idea of a scene of her own. She’s very willing to pay you,” he repeated. “I don’t think she’s ever paid anyone to do a scene with her. Or to have any kind of sex with her, for that matter. She’s just a regular married woman, but a good friend of mine.”
She sounded harmless enough. But you’d think after my years of turning tricks. I would have known beyond a doubt that people who sound harmless can be the most difficult customers when it’s all said and done.
Still, I agreed to do the three-way. We made an appointment for an afternoon the following week. For some reason, we were meeting in a tacky hotel in midtown – gone was the luxury of the king-sized bed, the crisp white sheets and room service. Everything about the hotel they’d chosen was dingy, seedy, and low class.
Mr Santos had asked me to bring along an outfit that would be suitable for a naughty little girl routine. Even though I’d never gone to Catholic school myself, I had a vintage Catholic schoolgirl uniform that fit me perfectly. I figured Mr Santos would get off on the religion thing so that’s what I packed for my change of clothes.
I’d been getting steadily more into the idea of the three-way as the day approached. Anything that involved the unpredictability of Mr Santos’s lusty libido aroused my own sexual appetites. He was nothing like an average trick. So when I knocked on the hotel room door that afternoon, I was already horny, already sopping wet between my legs. Until Mr Santos let me into the room and introduced me to his woman friend.
Oh my god, I realized in sick horror, it’s Mrs Hamilton.
She’d been my tenth grade sociology teacher. A woman who’d made my life a living hell for an entire year. I was certain it was her. To this day, I don’t know if she recognized me, too. If she did, she never once let on. But I knew it was her. She was simply using a fake name, like a lot of tricks do.
“Call me either ‘Daddy’ or ‘Sir’ today,” Mr Santos was instructing me. “And this is your new stepmother, Louise.”
Louise? They couldn’t come up with anything less corny than Louise?
I had that feeling of panic in my gut that I used to get in my early days of hustling; I wanted to bolt. But then I focused on the money: one thousand dollars cash for a single afternoon’s work. It would be worth it. But I saw immediately that it was going to be just that – work.
Mrs Hamilton had never been an unattractive woman; it was just that she’d always been a mean bitch of a teacher. In my years since high school, she’d managed to stay attractive; she’d taken good care of herself. I figured that if she knew Mr Santos, she must have money, too, and that always helps women stay good-looking. Yet it made me wonder why she’d chosen to teach at all. Perhaps for the sick thrill of tormenting teenagers?
“Louise wants to help you change clothes,” Mr Santos told me. “It’ll give you two a chance to get comfortable with each other. I’m going to run across the street to the liquor store. This trashy hotel doesn’t even supply booze.”
Shit. He was leaving me alone with her. The dreaded moment was starting to look even worse. Not only would I have to get naked for Mr
s Hamilton, I would have to be completely alone with her while it happened. No horny Mr Santos around to use as a buffer zone.
When he was gone, she went right into “efficient teacher” mode. “Come here,” she said flatly. “Let’s get you out of those clothes and into something more appropriate.”
She didn’t act like it made her at all nervous to be around a prostitute, to be doing a scene. I wondered if she was anybody’s horny lesbo stepmother in real life. The implications of that thought creeped me out. I had to force myself to keep my mind a blank.
Mrs Hamilton was going through my bag, pulling out my change of clothes. She seemed to recognize the uniform for what it was – something real girls wore in real high schools. “Are you Catholic?” she asked. “Not that it’s any of my business.”
“Yes,” I said. “But I went to public schools.” The sudden rudeness in my tone surprised even me.
She eyed me coolly, taking in that last remark. “Come over here,” she said.
Shit. She was actually making me nervous. But I went over to her. Without hesitating, she began undressing me. “Let me tell you something,” she explained carefully, unbuttoning my shirt with manicured fingers. “While we’re in the confines of this room, while we’re on the clock, so to speak, I have no qualms whatsoever about making it very clear which one of us is on top.” The sound of her words alone felt like a slap. She had my shirt off. She was moving to unfasten my bra then, her fingers were touching the skin on my back, her face was close to mine. I didn’t like it. “If you want to keep talking to me in that rude tone,” she continued, “go right ahead. But consider yourself warned. I’m not afraid of girls like you. I deal with your kind every day.”
My bra was off. My tits were right there in front of her, my nipples shivering to stiff points from the sudden change in temperature. How many times had I bared my tits for strange clients? But this took the cake for strangeness. I felt exposed.
She didn’t touch me, though. She barely even paused to look at my nakedness. She was already on to my tight jeans, unzipping them, tugging them down to my ankles.
I was in that state of half-undressed nervousness when Mr Santos came back to the room, carrying a fifth of gin and a large carton of Tropicana OJ.
Jesus, I wondered, how trashy are we going to get? Where was the top-shelf bourbon, or at the very least, some cheap champagne?
“Well,” he said, regarding us with satisfaction, “we’re certainly progressing here. Anyone want a drink?”
We all did. Mr Santos played bartender while keeping a keen eye on us.
Mrs Hamilton had me completely undressed, except for my panties. Those she seemed to want to take more time with. She lowered them slowly, anticipating the unveiling of my neatly trimmed snatch. She was actually squatting down in front of me, apparently wanting an up close and personal view. It made me even more uncomfortable – not so much that Mrs Hamilton was squatting down in front of me, so obviously aroused by the imminent sight of another woman’s pussy, but the fact that I was getting off on it, too. I was suddenly wet again.
“Good lord,” she said quickly under her breath. She’d peeled my panties past my mound, rolled them partially down my thighs and seen the strand of gooey wetness connecting my soaking hole to the cotton crotch of my underwear. She looked up at Mr Santos, who was now standing next to us, offers of drinks in his hands. “She’s so wet,” Mrs Hamilton explained in quiet earnestness, as if the sight of a twat swollen in arousal pained her deliciously.
I took my drink from Mr Santos and gulped it down. I needed fortification. Mrs Hamilton was fucking hot. And now she was licking me, her mouth was actually on me down there, and I was getting off on it.
Jesus, I wondered; what was going to happen here? Alone, unsupervised with two horny tricks who could get me this worked up; two people apparently intent on doing a pseudo-incest scene, with me playing the part of the helpless bottom, two tops wanting to have their way with me, and all of us downing cheap gin?
I was light-headed. I parted my legs as much as I could for Mrs Hamilton, but it wasn’t easy with my panties around my thighs. She held tight to my ass cheeks, her mouth flush with my mound. She moaned as her hot tongue slid eagerly around in the folds of my pussy lips, occasionally landing directly on the tip of my clit. I was soon so aroused by the lusty sounds she made, that I actually held on to her head to keep myself steady. I had a handful of Mrs Hamilton’s hair in one hand, and a plastic cup of gin and OJ in the other. It all seemed so decadently tawdry. The cheap thrill of it made me press Mrs Hamilton’s face even closer to my snatch, rubbing her face in the slippery folds of it. The horny bitch moaned even more.
Mr Santos lit a cigarette. He stood close to us, watching it all unfold, feeling up my titties while he watched – taking firm handfuls of titty flesh and squeezing, kneading, then tugging roughly on my stiff, aching nipples. He took a drag off his cigarette and then put his mouth on mine, forcing exhaled smoke into my open mouth along with his tongue.
The feel of his tongue filling my mouth, and Mrs Hamilton’s tongue deep between my sopping lips, while Mr Santos kept up his avid mauling of my breasts – I thought I’d come right on the spot.
But Mr Santos had his thoughts elsewhere. He pulled away from me the second before I had a chance to come. “This is going to be good,” he announced.
The sound of his voice seemed to bring Mrs Hamilton back to earth. She got up from between my legs abruptly, her mouth a slick mess. She went straight for the drink awaiting her on the dresser. I could see her mentally pulling herself together; reminding herself which one of us girls was on top.
Within moments, she was in stepmother mode. “I want you to go into the bathroom and put on your clothes. Your father and I want to be alone. We’ll tell you when to come out.”
I did as I was told, stopping first to refresh my drink. I closed myself up in the small, ugly bathroom and got into my uniform. Outside, I could hear the lusty sounds of them going at each other. I didn’t know in what way. Had they managed to strip out of their clothes in record time and begin fucking? Were they only partially undressed and sucking each other, or – just what were they doing? I was not only keenly curious, I was also jealous. I didn’t want Mr Santos to enjoy Mrs Hamilton that much; after all, he was my lover.
Of course, I’d been instructed to stay put in the bathroom until I was given permission to come out. But that was all part of the scene. Naughty girls went wide-eyed into every opportunity to misbehave. Otherwise, you’d deprive your scene-mates of the chance to spank you bare-assed – or worse, depending on the infraction.
I quietly cracked open the bathroom door and peeked out at them.
I’ll be damned, I thought.
They were fucking, all right. But they were, for the most part, still dressed. Mrs Hamilton was bent over the foot of the bed with her pants tugged down to her knees, while Mr Santos, cock out of his unzipped trousers, rode her hard from behind.
I was transfixed – they were in such a frenzy of lust. Plus the cheap booze had gone to my head. I couldn’t believe I was watching Mrs Hamilton get nailed, and in such an unflattering posture. Her white ass looked huge, sticking out like that.
I worked my hand up under my skirt and inside my white panties. I wiggled my clit furiously as I watched them fuck like dogs.
As if on cue, Mrs Hamilton glanced over at the bathroom door and caught me spying on them. It seemed to make her ass jut out even more, if that was possible. But she got a queer look on her face, too, like she couldn’t wait to get down and nasty on my own ass. I quickly closed the bathroom door and tried to mind my own business.
Naturally it was too late, and the incest-punishment scene was in full swing. There was soon a knock on the bathroom door. When I opened it, it was “Daddy.” He said, “Your stepmother wishes to speak to you.”
I came out of the bathroom to find my “stepmother” stark naked, sitting on the bed. She looked good naked, but she looked angry. “Come over her
e,” she said.
I expected to get thoroughly spanked by her and I wasn’t sure whether or not I would get off on it; she was still Mrs Hamilton after all, a woman I had once despised. As I went to her, there was a fear in my belly reminiscent of what I had once felt facing actual punishment as a child. Of course, this wasn’t a scene remotely close to anything that would have gone on in my own house. I hadn’t lost sight of the fact that we were all here for sex.
Daddy, still fully clothed, only his cock jutting out from his pants, sat down on the bed next to the naked “Louise.” He had a stern expression on his face that made him look even more handsome. I was hoping he would force me to make it up to him somehow – all his disappointment in how I had misbehaved. But for now, the emphasis was on Louise. This was decidedly her scene, the part she was paying for.
“Come closer,” she said.
I stood directly in front of her, cowering in my schoolgirl uniform.
“What were you doing in there?” she demanded.
“Nothing.”
“It was more than nothing, young lady. You were spying on us, weren’t you?”
“Yes,” I meekly confessed.
“Weren’t you told to stay in there until someone came for you?”
“Yes.”
“And why did you disobey me?”
“I don’t know.”
“I’ll tell you why, because you’re a dirty little girl, aren’t you? What do you suppose happens to a dirty little girl who disobeys and sticks her nose where it doesn’t belong?”
I gave it some serious thought. The look in Mrs Hamilton’s eyes was dark and unpleasant. Mr Santos, however, was in the throes of lust. He was watching it all while avidly stroking himself.
The Mammoth Book of International Erotica Page 7