Gifted Grifter Ch. 06

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Julie Pays The Bills (Part 1).
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Part 6 of the 15 part series

Updated 10/30/2022
Created 07/05/2007
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DrSqueaky
DrSqueaky
537 Followers

Chapter 6: Julie Pays the Bills, Part I

For nearly a year I had been living as the Gifted Grifter, and I was getting into an established routine. I would travel to Vegas or Atlantic City under an assumed name, betting horses and sports during the day, using my mindreading glasses to pick up tips from knowledgeable bettors. At night I would hit the poker rooms, using my glasses to know what everyone else at the table had in their hands when the table stakes got big; with those advantages, I could usually net 20-40K in about three days of play. I would then retire that identity for a while and assume a new one, swap out one prepaid cell phone for another, and for the next three months or so I would live off my winnings. I would travel a little, especially up to lake country, but mostly I would cruise for girls, using my glasses to custom-tailor my outward presentation so as to maximize my chances of getting them into bed. I was successfully seducing 5-10 girls a month, but almost all of them were one-night stands; that meant I slept alone two-thirds of the time, and even when I didn't, I wasn't really getting to know anyone. When I started as the GG, I was all pumped about the variety offered by having sex with many different partners. I didn't realize I would still be so lonely.

I was just back from Vegas, so it was time to change identities again. I figured that "Tom," the identity I had used when I first started living as the Gifted Grifter, had probably been dormant long enough that I could re-use it. Just to be sure, I checked Tom's MySpace page. I should explain; when I changed identities, the old one would disappear, right down to the phone number no longer being in service. But I realized I might meet some people along the way that I may wish to reconnect with later, so I had decided that I would create a separate MySpace page for every identity. If someone really wanted to contact one of my old identities, MySpace should be one place where they would look for me. They could send a friends request, and I could decide whether I wanted to be contacted or not.

I had no reason to think that anyone would want to contact "Tom"—but I was wrong. As "Tom," I had spent a few nights with a high-price call girl named Julie who worked under the name of Heather; she later texted me to tell me she had quit the business. She had moved back to her hometown of Oklahoma City last I heard; although I knew she credited me with helping her decide to leave the sex industry, really I was just a former customer to her. I had no reason to think she would want to contact me—but I discovered that in fact she had been trying to reach me for three months, with increasing urgency. She had even left me her direct cell phone number in several messages; I figured it didn't hurt to call.

The first time I called her, she was relieved that I was finally calling her, but she couldn't talk at the time. She said she would call back later that night. I told her to make note of the number I was calling from, it was my new one. I had no idea what to expect.

Finally she called me back. She filled me in that she was going to school, taking classes at the local community college. She had bought a condo with the money she had saved up as an escort in Vegas, and she was sharing it with a new boyfriend, who was also a student. Even after buying the condo she had some money left, so they had been in decent financial shape—until her boyfriend got sick. They found a lump on one of his testicles, which they removed and he had gone through additional chemotherapy. He seemed to be completely remitted, but as a student he didn't have any health insurance. She had spent all of her remaining savings on his medical bills, and they had taken out all the student loans they qualified for, but they were still $15,000 short—and the medical collectors were becoming aggressive. If she didn't pay them soon, she was going to have to sell their condo; selling quickly in a soft market, she would be lucky to get half of its market value back. She started to sob briefly when she said she had worked hard to get the life she now had; she really didn't want to start over again. She needed to find a way to make $15,000 quickly.

"I'm guessing this is the part where I come in," I said, mildly annoyed. I felt bad for her, but I was not about to become a charity for retired hookers.

She picked up my annoyance right away. "Look, I think you would have the money, but I would never just ask you to give me $15,000. If anything, I already owe you—you were so nice to me in Vegas that you gave me the courage to try to reclaim a life for myself again. I didn't call to beg...I called to propose an....arrangement...where I might be able to work to earn the money."

I had no idea where she was going with this. "What sort of arrangement did you have in mind?"

"I can't go back to Vegas. I really don't want to have sex with complete strangers anymore, let alone having to worry about how my boyfriend would react if it came out what I was doing," she said, "but I don't think of you as a stranger. I feel I can trust you; truth is, I kind of like you, and I think I would like you even more if I got to know you better."

"Well, thanks I guess," I said, still perplexed, "but what does that have to do with your needing $15,000?"

"How would you like to be my sugar daddy?" she replied, turning up the sultriness in her voice. "I can be a real, real good little girl..."

I wasn't sure I was understanding her right. "Sugar daddy? Excuse me if I'm being slow, but what exactly do you mean by that?" I asked.

"It means that you take care of me like you were my rich daddy, and I show you my appreciation by giving you some of that special sugar only I can give." she purred. "I kept a lot of my old tools of the trade from when I was working, I could dig them out again..."

"Wait, I'm confused. Are you offering me sex for money?" I asked. It sure sounded like it. "How is that different from going back to hooking?"

"One, rather than having sex with a complete stranger every night, it would be having sex with someone I know—you" she explained. "Two, I wouldn't have to go out looking for johns, so there's no risk of getting arrested. And three—what makes this a good deal for you—there's no fixed rate of exchange. You pay a prostitute a set fee, but as a sugar daddy, everything is voluntary. I've told you how much I need, but it's up to you what if anything you want to give me. And since I'm dependent on your good will for what I want, it's in my interest to make you as happy as possible so that you'll want to give me what I need." "So you'd basically be trying to earn $15,000 worth of good will from me by satisfying me as much a possible," I paraphrased.

"Whatever you want, whenever you want, however you want it, as often as you want" she purred.

Hmm. By the sound of it, this was an open invitation to a weekend of wall-to-wall fucking. And one thing I knew from my prior experiences with Julie, she was pretty damn good at giving a man EXACTLY what he liked. I couldn't deny being at least a little interested. I told her I'd think about it.

It was a little after 11 when I hung up the phone. I got in my car and drove down to one of the local watering holes, wearing my mindreading hat. There were a number of girls there that I would have taken home with me, but I was unable to talk any of them into it. That's the thing about the mindreading hat: you can read people thoughts, but you can't influence them. Same thing in poker: it's a huge advantage to know what someone else has in their hand, but you still have to have a better hand to win.

Having returned alone, I lay in bed thinking about Julie's offer. 15 grand was a lot of scratch; in fact, I didn't have it to spare, I would have to go and make some money first. But it also meant that I would have a weekend of high-quality sex whenever and however I wanted it. I was up for that. In truth, I was having a mental block around the boyfriend. Funny, when I picked up chicks in other places I usually didn't care that they had a boyfriend—course, I usually only talked to them if I could tell that they were unhappy (and thus potentially seducible). She hadn't really said much about her relationship with her boyfriend other than she had spent her saving on his bills, but no matter what she would have to cheat on him to keep her part of the bargain. I envisioned her fighting guilt about cheating on her boyfriend the whole time she was trying to satisfy me, and that as a result she wouldn't be the same expert man-satisfier I had known in Vegas. I didn't think this was going to work.

I called her the next day and told her so; I didn't think I could be her sugar daddy knowing that she had a steady boyfriend back home.

"Once again, you are being the nice guy," she said, "not wanting to be with a girl cheating on her boyfriend. But I wouldn't have made this proposition if I wasn't desperate, and I fully intend to keep my part of the bargain. I know this sounds weird, but it's because I have a boyfriend that I am making this proposition. Like I said yesterday, I couldn't go out picking up johns again. But you...I think of you as a nice guy, someone who I can trust—someone I could easily imagine choosing to have sex with in the right circumstances. Yes, I do have boyfriend and no, I wouldn't cheat on him for no good reason, but its not like we are not married or engaged or anything. As far as I'm concerned, I'm single, and who I sleep with is my decision. You're the only person I know that might be able to help me out of this bind and is also on the list of people I would be interested in sleeping with."

That was kind of flattering, in a way. "I think you may be underestimating your attachment," I countered. "Your feelings about your boyfriend may feel like something you can put aside when you're a thousand miles away, but I imagine that when the moment of truth came, you'd feel guilty—which would make me feel guilty—and it wouldn't work for either of us."

"I thought about that a lot before I called you," she answered. "That's why I couldn't do this with anyone else but you. I think of it like spending time with an old flame, and I am still single enough to have a right to do that. And," she continued, "I think you underestimate the degree to which a working girl has to put aside her feelings in order to be sexy, especially when you're asked to do something that deep down you hate to do. So you needn't worry about that; I can and will be every bit as available to you as when you knew me before. I am making this offer to YOU after all, not the other way around. You should not feel any guilt about accepting what I am freely offering."

That last line made a lot sense. She might have lingering guilt issues once she went back to him, but I needn't concern myself with that. She was making an unsolicited offer to me; on my end, the only question should be whether I wanted to accept it or not.

"Well..." I said.

"Don't forget, for you there's no risk. If you don't feel that you got what you wanted out of the arrangement, you don't have to give me a dime," she said. "I'm the one taking the risk—its up to me to prove to you that I'm worthy of the money I'm asking you for. If I can't deliver to your satisfaction, well then you'll have gotten a whole lot of free sex."

That convinced me. I didn't have to give her the money just because I knew she needed it—I probably would, but if she came up and just started bawling, well, I wouldn't be out much. No, she was going to be working her hardest to satisfy me for a whole weekend. It really did seem like I couldn't lose.

"All right, I'll give it a go," I said. There was a long weekend coming up; I asked if she could fly in on Thursday and stay until Sunday. She said she would find a way to be there. I asked her for her last name and email so I could buy her tickets and she would get the confirmations. I told her I would pick her up at the airport and I would take care of everything from there. She agreed. Then in a purposefully naughty tone, she ended our conversation with "Thank you, daddy. You're so nice to me. I want to be nice to you, too."

This could be fun, I thought as I hung up the phone.

I went online; now that I knew her real name, I looked her up in a number of legal databases. Julie had no arrests in Oklahoma. She had two arrests in Nevada, one all charges dropped, one conviction for solicitation. It seemed she was on the level, so I went ahead and booked airline tickets for her.

First thing the next morning I called Erin, my real estate agent, and arranged for a rental for the long holiday weekend. Being a popular weekend, there wasn't as much available as usual, but she found a small, older lake cottage for us. I told her I'd have to mail her a check this time; I usually paid cash up front for my rentals. I sent Julie a quick message telling her to pack a swimsuit she could actually swim in.

That settled, I rented a car—not just any car, but one with style. I looked at a number of exotics that I figured were a little too fragile for lake country; I finally settled on a brand-new Mustang convertible, red with retro-style black rally stripes to match the roof. I put the top down and started driving. My destination: Chicago. For three days I spent my days in the OTBs of Chicago betting horses. I then would drive to the casinos in northwest Indiana and play the highest stakes poker game I could find. I wasn't the stakes I was playing in Vegas, so it took a lot more time to make much money. Fortunately, I had good luck at the track, and cleared almost 20 grand in the three days.

I stopped at three banks on the way back; at the first two, I had $7500 cashier's checks made out to Julie (I had to split them up or the feds would start tracking me as potential drug dealer). The third I sent to my real estate broker. The major arrangements now complete, I drove back home. I had a couple of days before she arrived; I spent much of them deciding what I was going to have Julie do to earn her money.

-----------------------

Julie's flight got in at 1:30. With modern airport security, I had to wait in the main terminal area; I couldn't greet her at the gate. I smiled when I saw her coming through the gate; she was wearing tan shorts and flip-flops with a tight, light blue tank top; she had knotted the tank top in the back so that it now rode above her belly button, displaying a new belly button ring. I was starting to understand Julie; I had no trouble imagining her wearing her tank top normally for the entire trip, then just before landing going to the bathroom and tying it up short so as to make a better show when she deplaned. And quite a show she made; as with almost every other time I had been with her, every man I could see was stopping to stare at the gorgeous blonde showing bountiful amounts of skin. She probably knew they were looking, but as always her concentration was fixed on me as if I was the only person there. In many ways, that oneness of purpose was as sexy as her outfits. She had been growing her hair out and was more tan than she was when she was working nights in Vegas, but her flat stomach and defined abs remained.

She waved and came right up to me and threw both her arms around me in a big hug. I hugged her back, my hands touching the bare strip of skin at her midsection. Then she gave me a kiss on the cheek—not the quick continental hello-goodbye kisses we had shared before, but rather a kiss of affection. I wasn't expecting that. I guess she had meant it when she said she could imagine freely choosing to sleep with me.

I went with her to get her luggage. She had a decent-sized carry-on and not one but two suitcases. At first I thought what can she have in there, she's only here for four days. Then I remembered her telling me she still had a lot of tools from her working days, and I realized she had probably brought along extra goodies for me. Wow. She was serious about this.

I carried her bags to the Mustang like a gentleman, then got in, pulled the top down, and started driving.

"Nice car," she said.

"A rental," I admitted, "I told you I move around from place to place a lot, that's why you couldn't reach me for so long. Renting is much easier when you're always traveling. I've rented us a cottage on a lake for the weekend."

"Wow, really?" Julie asked. "That was nice of you. Sounds like fun."

"I go up there a lot," I explained, "so I thought it would be nice. I'm sorry, though, because after your flight and all it means we still have a three-hour drive ahead of us."

"Well, with the top down I can work on my tan," she replied.

We made mostly small talk in the car. She ran her fingers through my hair a few times, but not much else happened. About halfway to the lake there was a rest stop and Julie needed to use the bathroom. When she came back she asked if we could close the roof, she had had enough wind for a while. I was actually thinking the same thing. But since I wasn't wearing my glasses or hat, I couldn't tell that it was actually a ruse.

I put the top up and started driving. She now turned around in her seat to face me while I drove. She ran her fingers through my hair a little, but then changed hands and started running her fingers up and down my thigh. My little Tom received the wakeup call. When she saw the bulge start to from, she started to rub it with her hand. I had been racing through the traffic, but now I slowed down so that I wouldn't crash into anyone while driving in half-distracted state.

She reached over with both of her hands and unzipped my shorts. It took a little finagling to free my hard-on from under my t-shirt and boxer-briefs while I was sitting and seat-belted, but she accomplished the task. She took my penis in her hand and gently, expertly stroked it. In the meantime, she leaned over and put her tongue into my ear (good thing I'm not very ticklish). Then, with a devilish look, she slipped under the top seat belt and bent over so as to take my penis into her mouth.

I was a captive; I couldn't move much and still drive. Not that I would have wanted to, mind you. She knew I could do little but sit there and take what she was giving. And what she was giving was a first-rate blow job. She was in no hurry; we still had over an hour to go. She seemed to like the feeling of control she had, slowly sliding my dick into and out her mouth, sensing its responding to her administrations. For almost 20 minutes she just played, her mouth and my dick. Then she started to speed up and suck harder, knowing this would bring me to orgasm. In short order, it did. Again she surprised me; she held my penis in her mouth while it was ejaculating, then swallowed my entire load. She then used her tongue to clean my penis off entirely before slipping it back into my shorts.

"Did you like that, Daddy?" she teased.

"I think we're gonna have fun this weekend," I replied.

I took my mindreading sunglasses out of my pocket for a moment and looked at her to see what she was thinking.

"Okay, that's a start," she thought. "Now maybe he won't be so afraid that I won't keep my end of the bargain. What's next...I know, when he shows me be bedroom I'll strip for him and jump into bed naked right away. We'll have to see what happens after that."

"Eh, I don't like these sunglasses as much as my other ones," I pronounced to explain why I would be taking off one pair and replacing them with another (my non-mindreading ones). It was clear that this weekend Julie was bound and determined to have sex with me every time I showed the slightest interest. I was going to be much happier, for a change, just letting her surprise me.

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When we got to the cottage, Julie was good to her word. The cottage was old and small, but had been kept clean. It had a high arched ceiling with a loft, a small open room by the front door, a small bathroom, a galley kitchen, and a single master bedroom. I carried my bag and one of Julie's, she carried the other. We took them to the back bedroom.

DrSqueaky
DrSqueaky
537 Followers
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