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.”