Virgin Gigolo Ch. 03

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, 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. We'd then 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.

~

"Are you Mary's... friend?" the woman answered when I knocked on the door.

"Helen?" I asked after nodding affirmatively to her question. "I'm... Brent," I said, sticking out my hand. I hadn't put any thought into a phony name, it just popped into my mind that sex workers used stage names, so I'd listed the phone as "Brent's Tree, Yard and Maintenance Services." Sure, Mary knew I was Danny, but Helen didn't need to know that. Before the phone had rung the first time, I'd taped that name to the phone so I wouldn't get it wrong.

I had double checked the address as I'd driven up to the house. Mary hadn't been wrong, the McMansion that I drove up to, if she really owned it outright as Mary had said, indicated that Helen was indeed loaded.

Surprisingly, Helen really wasn't bad looking, was actually quite good looking, just that she was not 21 anymore. If she'd been a "trophy wife" at one time, she wasn't far off now. I hadn't been expecting that Helen would have no experience at paying someone for sex thinking that someone, who would hire a gigolo over the phone, had probably done this before. "So, uhm... how does this work?" she asked as I stepped inside. "Shoes off," she said, motioning to the side and I slipped them off, pushing them to the wall beside the door.

I began to evaluate her as soon as she opened the door. She had tight-fitting exercise shorts with a color coordinated sports bra top. The front of her breasts were smooth, no tight little buttons of nipples poking through. I assumed this meant the top was a padded bra. Somehow, I realized these were high end clothes.

"Well, there's a two-hour minimum, and I collect that up front, and then we deal with the... special services. If we reach two hours and you want to continue, we'll deal with that afterward."

"Oh yes, of course," she said, and turning to the adjacent hallway she opened a drawer and withdrew an envelope. I thought she was going to hand me the envelope, but instead she opened it, pulled out five bills and handed them to me. I smiled and said thank you, folded the bills and put them into my pocket. She turned and put the envelope back into the drawer, and then turned back towards me. I'd moved up to the hall entrance, but didn't yet intrude upon her. She stopped and turned, pushing her bottom back against the cupboards. "I, um... gotta admit I'm a little nervous."

"No need to be nervous, we're just getting to know each other," I said, reaching my hand out to hers again. She raised her hand and took mine. "All you need to do is tell me what you want to do. Have you got someplace special you want to go? The bedroom, or..." I glanced down at her body and her workout clothes, "the gym? You do have a gym, don't you?"

She nodded toward the living room and said, "Let's go to the living room," as she stepped around me pulling me by the hand. Now behind her, I let my hand slide up her arm to her elbow, and when she stopped with my other hand reached her other elbow. I immediately sensed tension in her body, and slid my hands up her upper arms to her shoulders. "You're really tense," I said, sliding my hands towards her neck and squeezing. "We can take this as fast or slow as you like."

"It's been awhile," she said, her head now rolling back and forth as I massaged her shoulders lightly.

"I understand." I gave it a minute or two, began to feel her relax. I relinquished her shoulders, running my hands back down her arms and onto her sides. I slipped them down her waist to her hips, caressing her sides, and then when I reached the center of her back slipped them under her arms, onto her breasts, and pulled her back against me. I immediately sensed I'd guessed right, she wanted me to direct where this was going. "Is there anything in particular that you want?" I asked. I had originally thought I might slide my hands in underneath her sports bra, but could tell it was too tight. I'd have to pull it off completely. Slipping my fingers to the bottom edge I began to work it up.

"I..." she began, and then changed her mind, "I'm not used to just saying these things."

"I know," I said, my fingers lifting, her bra easily pulling up and over her breasts. She lifted her arms and the bra slid up and off. This time, when I filled my hands with her naked breasts, I could readily feel her nipples hardening to my touch. "But I'm not going to know what you want until you tell me."

"I... I want you to eat me. I want your tongue on me." I could tell she was at first hesitant to say it, but once she started talking, her words tumbled from her mouth.

"Always a favorite," I said, feeling like a fraud as I said this, implying that I'd had lots of women requesting the same, while slipping my hands from her now naked breasts to the top of her workout shorts. I couldn't help but wonder if she could tell I wasn't all that experienced, that I'd only had one lover before, or rather that I'd only had sex with one other woman before.

Just as with her top, her shorts were form-fitting, with very little room to do anything other than to push them down and off. I pushed, and once they were down past her bottom she reached down and slipped them off her legs. As she did that, I pulled my shirt up and off and retrieving condoms from my pocket, slipped my pants and socks off so we ended up naked at virtually the same time, with just a single pile of mixed clothes in the middle of the floor with the condoms beside them. I reached for her arm again, taking it and turning her to face me. Her eyes were on mine, and I could sense the bashfulness from her. "It's ok to look," I said, "I'm all yours for the next two hours." Her eyes still on mine, she sucked her lower lip between her teeth and slowly lowered her eyes to my cock. Her hand moved between us, wrapping around my erection, her eyes wide as they again rose to mine.

I was rock hard and ready to fuck from the beginning, but all of Mary's lessons drove my responses. I listened to Helen's body, to her clues, to her hesitancies and let her think she was leading. Just weeks before, if I'd been in this position, I would have totally blown it, letting my cock lead my brain, but not this time. I did as she said she desired and licked her to orgasm before we fucked. She was ready for a bit of a rest after that, but didn't fend me off when I went down on her again a bit later. By the time I filled her with my cock and filled a condom a second time, she was sated.

"Oh my God, Brent. Where did you learn to treat a woman like that?"

"I had a good teacher."

"Can we do it again?"

"Now?" I responded, misunderstanding her query as saying she wanted to do it again immediately.

"No," she giggled, "Oh My God, I don't think I could take it again now. I was thinking next week."

"When were you thinking?" I asked.

"Same day? Same time?"

"I'll have to check my calendar," I answered evasively, not wanting to seem too eager, "but I think this afternoon is normally free."

"What about other days?"

"I can't say outright, like I said, I'll need to check my calendar, but I've got openings all the time. If you want, give me a call when I can double check and I'll let you know." I didn't really need to, I knew exactly what my schedule was, but figured she didn't need to know that.

"I want to suck your cock next time; I really do like doing that. I take it that's ok?"

"If that's what you want," I said, nodding. "I'm here for you, so it's whatever you like."

"I'm sorry I didn't do that for you this time."

"I wasn't here for me; I was here for you."

"Thank you. You were exactly what I needed." I saw her raise up and glance over at the clock. "About out of time?" I just cocked my head and then straightened it up again. She sighed. "You'll let me know about next week?" She sat up and swung her legs over the bed.

"I'll check my schedule as soon as I leave, and I'll put you in."

~

"I heard back from Helen," Mary said on Saturday a few weeks later when she was riding me cowgirl. After I'd finished the painting, we'd gotten to where we were spending all morning in her bed. Mary would only pay me her regular $250, but we'd fuck and suck and read and pleasure each other all morning. I never asked her for more. "She said you were really good. How many times have you seen her now?"

"Five." I didn't have to count, I knew.

"Really? What's it been, three weeks?"

"Four, but I went to see her twice the second week."

"You're becoming quite the stud aren't you? Servicing Helen during the week and me on Saturdays?" I didn't answer immediately.

"Actually, there's another one, too."

"What? Who?"

"I haven't seen her yet, but I've got an appointment with her on Wednesday."

"Who is she? Do I know her?"

"I don't know if you know her or not. Her name is Mitzi, she's a friend of Helen's."

"I don't know the name. Where does she live?"

"I don't know, we're going to meet at Helen's. Apparently, she's got some kids, so Helen agreed to let her use her place.

"Oh my god, that's so hot!"

"Hey, Mary?" I said a minute or so later as I was getting dressed to leave, "Can I ask you a question?"

"Sure..." she answered with puzzlement as we'd certainly not be hesitant on talking about things.

"I'm just curious. You told me to be sure to collect money before we had sex, to get a cell phone, to keep track of what I was collecting as the IRS would certainly be questioning if I had lots of money but didn't report any income... Where did you learn all that?"

She stood there looking at me momentarily, her head nodding as she thought about it. "Good question," she finally answered. "I guess it doesn't hurt to tell you, but it's not something I normally talk about. My Robby knew of course." She sighed, "I learned all that from my older sister. She was an... uhm, what do I say, a high-class call girl? A kept woman? A paid mistress? She was for years."

"Really?" I said, knowing she wasn't making this up, but it was a bit surprising. She nodded.

"She got picked up by a businessman in a bar one night when she was in college. He was older, but when he propositioned her, he just whispered that he'd give her a thousand dollars to spend the night with him, no questions asked. Of course, that was years ago, when a thousand dollars was really big money... and she became his mistress. A hot young body, and she was a hottie, she found that older gentlemen often had more money than guys her own age and could support her in the fashion that she had always wanted. She graduated with a Business Degree, and, well, started her own business." She shrugged her shoulders. "She asked me if I wanted to do it too, she said it was really good money, and even to this day... well, I guess she's no longer just a "kept" woman as when the wife of one of her clients died, she moved in with him."

"Wow," was all I could say, "she married him?"

"No, he never asked, although she said she would if he did. She just moved in with him. She's actually still got three other clients, but at their age she's only seeing the others about once a month."

"How old is she?"

"She's 64. She'll be 65 in another three months."

"Wow, so she's living with one man, and she's got three others that she's... seeing regularly?" I started to say fucking, but thought it would come across too negatively. After all, I was now fucking for money, too. "And he doesn't mind?"

"I guess not. He's known what she did for a living as long as she's known him, and apparently, he has no problems with her work. As she said, she makes love with him, but only has sex with the others." My mind immediately flashed back to Mary telling me the difference between making love and having sex. I couldn't help but wonder if she'd learned that from her husband, or from her sister.