It was three week later, and I'd just about finished painting the entire house, which is no mean feat when you're working all by yourself. The actual painting I did in just a couple of days, only a fraction of the time it took to prep. Mary had been gone all morning, and when she came out after she got back she asked if I could take a break and come inside for a few minutes.
"Coke?" Mary asked, indicating for me to pull up a chair at the kitchen table, "Or Iced Tea?" I indicated a coke would be good and she'd turned to get it for me. Now that I was into painting and not just prepping, all I had to do was shuck my painter's overalls as the door and I didn't need to worry about getting paint or dirt inside her house. I sat.
"Danny, are you interested in making a little more money?" Mary asked when she also pulled up a seat at the table. Of course I was, I'd told her that before, so why was she asking this again? And then it dawned on me.
"Sure..." I paused, my mind immediately latching onto and racing to conclusions that, since she was asking, this was something out of the ordinary. "Doing what?" I cautiously added. Although her previous "out of the ordinary" had resulted in me getting laid regularly and sometimes getting paid for doing it, I really didn't want to just outright say "yes" before I knew what it was.
"I uhm, sort of let the cat out of the bag with my friend Helen, uhm..." she paused, "about... our arrangement." I swallowed, hard, and nodded that I understood what she was indicating. "I didn't intend to, but no sooner had we sat down at the restaurant than she looked at me and said, "You're getting laid!"
I immediately thought about our morning. Today had been unusual - for the first time we'd played
before
my other work. She'd called me earlier in the week to tell me she was going to be gone all afternoon and evening and asked if I'd like to collect my "high-priced time" first thing in the morning. I'd agreed and came over an hour early that morning at 7. We'd spent three hours in her bed before she sent me out to paint. Of course, since I was charging her by the hour for the painting, I didn't exactly make $250 more than I would have, but I wasn't complaining. She rode me the first time, we'd gotten out one of the naughty story magazines where she then snuggled in and sucked my cock while I read something called "Call Me Madam" by someone named Xaviera Hollander, until I couldn't take it anymore. She sucked me dry, and then we'd switched, and I'd tongued her to orgasm twice while she read, and by that time I was hard, and we fucked again.
I don't think we ever did it for
only
an hour, and despite not paying for it, we'd been finishing every Tuesday in bed also. I'd work for an hour or two, I'd come in and she'd climb in the shower with me, and then we'd fuck each other silly. But every Saturday, until now, we'd finished the day in bed, and taking her lesson to heart, I wouldn't touch her until she paid.
For the most part, I always concentrated on pleasuring her first. She was right, I'd never gone wanting, and it had constantly just gotten better. I learned what she really liked, and learned what she liked me to take charge on, and what she liked to take charge on. I don't think we ever settled with just two orgasms for her on Saturdays, which over multiple hours wasn't all that hard, but with less time on Tuesdays I always had to concentrate to get her off at least twice.
"You told someone... about you... having sex with me?" I asked, confirming what she was saying. We'd said this arrangement was going to be private, we'd never tell anyone, and we'd act like we were "just" acquaintances if we ever met in public.
"I didn't tell
who
you were, just that... well, that I was paying for sex."
"I thought we weren't going to talk about it."
She cocked her head sheepishly. "We weren't. I wasn't. But it just sort of came out. I couldn't deny that I was getting sex, and she wanted to know who I was dating. I tried to avoid the question, but she kept coming back to it, wanting to know who was getting into my pants. She kept asking who my boyfriend was, if he was a co-worker, if she knew him, how old he was, how long we'd been dating. I tried to give evasive answers, but it just wasn't working. Finally, I just told her I had "an acquaintance" and that I wasn't dating him, I wasn't "seeing" him, I was paying him for sex."
I just sat and looked at her; she took a sip of her iced tea and continued. "Of course, then she wanted to know who it was, how I'd found him, how old he was, was he any good in bed." She giggled. "I told her you were phenomenal in bed, that you couldn't be a better lover if I'd taught you myself. I told her I had met you through a mutual friend, and that you were going to an expensive university, and this was how you were paying your way through college. She said 'Wow! College age, and experienced? So, what is he, 21... 22?'" I just shook my head and said I thought you were 19."
"18," I corrected.
"I know, but I didn't want to tell her your real age. And then she asked how much you charged."
I nodded, evaluating what she was saying. "And?"
"I told her you were $500. $250 an hour with a two-hour minimum."
My mind was racing, contemplating everything she'd said. Basically, she'd told her friend that she was paying me twice as much as she actually was, but so far had only hinted that her friend was interested in a similar arrangement. "What did she say?"
"She didn't bat an eye, she just asked if she could get your contact information. I told her I didn't know, but I could always ask. She just nodded and said, 'If he's available, I know three of us who would gladly use him just to avoid dating some loser."
"Three
"? I repeated, shocked, but immediately multiplying numbers in my head. With a $500 minimum, if I was seeing them even once a month that was $1500, and on top of Mary seeing me once a week, that was another grand.
"Or four," she corrected, "I'm not sure if that was three
others
, or three including herself. The way she said it, I think it was three other women."
"I don't know," I said, shaking my head. "This is Helen? I don't know anything about her, do I?"
"Probably not. She's pretty good-looking, and I think she's 44. She was a trophy wife 20 some years ago to a husband that traded her in two years ago for his 21-year-old secretary. He got the secretary and she got everything else as long as she let go any claim to his future income. She said she'd dated a few men over the past two years, but every last one of them is after her money. She said she'd gladly just pay for sex rather than having to vet every last dildo who thought she would set them up for life."
I don't know why I was hesitant. Why was this any different than getting paid $250 once a week by Mary? Sure, I was doing it with her for free on Tuesdays, but my painting job was practically finished, and then it was probably just back to mowing her yard -- as if that was going to pay my way through college. It wasn't until I asked her opinion, and she admitted that if I really needed college money, I'd be a fool not to at least try it out. When I asked her if she wanted to give out my phone number, I was surprised when she said no.
"No?" I questioned.
"No. You need to go get a new phone, one that you pay in cash for, and isn't connected directly with your name. You can give out that number."
"What? Why?"
She looked at me and raised an eyebrow. "Paying for sex, even if it's a woman paying a male, isn't exactly legal in this state. You also need to answer with a business name. I told her that, when we talked, I asked for "Yard Maintenance and Special Services." If you really do this, you're going to start collecting more than just pocket money, then you're going to need to put it in the bank, and for that you'll need a reason why all this cash money is coming in if you don't want to be answering questions to the IRS. And believe me, you don't."
And that's how I agreed to meet Helen.
