Gifted Grifter Ch. 08

Gifted Grifter #8: The Return of Jessie

My "sugar daddy" weekend with Julie changed me. I missed her terribly after seeing her off at the airport. Since the time I had invented the mindreader until that weekend, I my primary objective had been to use my device to seduce as many hot women as possible. But now, when I thought of having sex with a hot woman, I always pictured Julie. Simple fact was, everything I liked to do—which was pretty much everything—she did better than any other woman I had ever been with.

Some research suggests that feelings of love grow out of positive sexual feelings. I no longer questioned it, because love was the only word I could come up with to describe how I felt towards Julie. Sure, I had always liked her, even when I had first met her as a prostitute in Las Vegas. But after spending a long weekend with—much of it inside—her on a voluntary, "sugar baby" basis I found myself loving everything about her: the sex of course, but also the way she thought, the things she did—see, just listen to how sappy I sound! What else could it be but love?

At least to some degree, I knew Julie felt something too. Our weekend was probably supposed to have been a one-shot deal, but by the end neither of us could bear to think of not seeing each other again. We ended up planning a follow-up rendezvous—but that wouldn't be until a convention that was coming up in seven weeks. Suddenly that seemed like an eternity.

For more than a week after Julie went back to Oklahoma, I moped around my apartment feeling lonely and sorry for myself. What stuck in my mind was Julie crying at the thought of leaving me, and her vague comments about her problems back home. She said that being with me seemed to much more...is carefree the word? I really wanted to bring Julie back home to live with me, permanently. At the same time, I kept reminding myself that Julie had a boyfriend, which is why she was in the financial mess that led to our weekend in the first place. A different part of me was convinced that spending time with her boyfriend again would lead to a change of heart and she'd cancel out on me entirely.

I was driving myself insane with all these internal conflicts. I decided I needed to do something to pass the time until the conference, so I put my Gifted Grifter sunglasses back on and headed out to find a new playmate. This would normally be the kind of thing I might do up in lake country, but since that's where I'd been with Julie, I wanted to stay closer to home. Thus, silly as it sounds, I rented an extended stay room for a week in my own hometown. I also decided I wanted to drive something nice for a week, so I went to a car rental and asked about their premium rentals. I was thinking nice...maybe a Ferrari or something. They didn't have any of those, but because they had an agreement with Ford, they could get me a Ford GT (they would have to bring it up from another city). That sounded like fun, so I arranged to pick it up the next day.

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Early the following afternoon, I was cruising up and down the roads in the largest park in my home city. A nice jogging track wound in and out of the trees off to one side of the road, and it was the most popular venue for runners in town. I was driving around, looking at a number of very fit young ladies working their up and down the trail. Then ahead in the distance I saw one very tall, very fit young woman, running at a good clip. Most girls put their hair in a ponytail to exercise, and the ponytail bobs back and forth as they run. This girl's blonde hair was so long that the ponytail was too heavy to bob but a tiny bit. As I cruised the GT by at 25mph (park speed limit,) I turned to catch a glimpse of the hot blonde jogger.

As I passed her face, it took a second to register that I knew her. The hot jogger was Jessie, my former graduate assistant. I knew she was hot (I had even fucked her once), but running in dark blue jogging shorts and a matching sports bra/half-top, both with white stripes on the side for accents, she was quite the sight for sore eyes.

Just a few hundred yards ahead of where Jessie was, there was a spot where the jogging track arched outwards and came very close to the road. I stopped the GT at the apex of the bend, opened the window, and waited for her to come into range.

Jessie saw that a racy sports car had stopped on the road just by the part of the trail she had to go past next; she steeled herself for fending off (yet another?) likely pickup attempt. With her mind in full defense mode, she kept running towards the car. With the little windows on the GT and her mind set on rejecting an anticipated advance, she didn't really see who was in the driver's seat.

She was expecting something like a "Hey baby." It caught her quite off-guard to hear "Hey Jessie, how have you been?"

She stopped running and started walking slowly towards the car. Having not seen me for several months and not expecting to hear my voice coming out of this wonderful piece of Detroit muscle, it took her a second to figure out who was talking to her.

"Dr. 'Grifter'?" she asked hesitantly.

I called out, "I'm not your boss anymore, so please use my first name." Jessie was a good fuck; I wouldn't think twice about re-bedding her should the opportunity arise. Fostering familiarity was a step in the right direction.

Jessie came up to the car, put her arms on the window opening, and poked her head inside.

"I certainly didn't expect to see you running around in a car like this," she marveled, "especially since you've basically disappeared for the last six months."

It dawned on me that all of Jessie's contact information for me would have been my official, Department of Defense email and phone, which would have been removed the day I turned in my resignation. That, and a cell phone number I had given up long ago. And while I created MySpace pages for my false identities, I had intentionally not created one for my real self.

"I'm sorry. What I'm doing now is a lot more secret than DoD ever was—I'm not easy to find anymore." That was half-true—what I was doing now was secret, but not in the sense of being classified—only in the sense that there was no way I was going to tell her what I was doing these days.

"I've been trying hard to get a hold of you," she continued. "You know all that dissertation data I collected...I can't use it," she replied.

I had delayed beginning my life as the Gifted Grifter for three weeks just so she could finish collecting her dissertation data. I was not happy to hear this.

"You can't use it? Why not?" I asked.

"All those MRI's—they're like encoded or something. I can't pull them up to analyze them," she said.

Duh. Files copied from DoD computers are automatically encrypted, since they usually contain top secret information. But usually... "Do you get a prompt for a password when you first access the disk?" I asked.

"Yeah," she replied, "but I plugged in my DoD passwords and they didn't work."

No, they wouldn't—they would require a supervisor's password, namely mine.

"OK...did you burn those files to CD while I was still working at DoD?" I asked.

"Yes," she replied.

"Get in," I told her, "it needs your supervisor's password to unlock the encryption—and if you haven't plugged it in to a DoD computer since I worked there, it should still be looking for my last password. Take me to your computer, and let's see if I can't unlock those files with my old password."

Jessie's apartment was in a neighborhood favored by graduate students. She was telling me how she had given up on her original dissertation and was working on a new angle, but would have to spend at least another year in data collection again. She would be ecstatic if I could resurrect her original dissertation—but she had by now been frustrated too many times to get her hopes up. I had expected her to be finished by now; I felt bad that she was delayed in spite of the favors I had done for her.

Her apartment was small but meticulously kept up. On one shelf of the unit that held her books were medals and mementos of her undergraduate Division I volleyball career. There was a small entertainment center; the rest of the room was set up for studying. Jessie was a very goal-oriented girl.

She disappeared down a hall way and came back with a laptop which was already starting up. She put it down in front of me, fetched a CD which she put in the drive, and logged in.

"OK," I said, "let's see what happens." I opened up the CD-R for browsing and double-clicked on what should have been an image file. It immediately popped up looking for a password. I entered the last password I had used at DoD. The file opened up in a special, high-resolution graphics program used for interpreting MRI data.

"Oh my god," Jessie squealed like an eighth grader, "you opened it."

"Yes, but now let's save them all to new files on your hard drive," I said, "because it will do the same thing every time you try to read this CD." I handed the laptop back to Jessie and waited while she quickly opened every file, renamed and resaved it. Her long blonde hair was tied back in a ponytail; her slender belly as it showed between her jogging bra and shorts gave me something pleasant to contemplate.

Finally she was done. She was so happy she jumped up and hugged me as I sat in her armchair; "You just saved me a year of work! Now I might be able to graduate next semester after all. How can I ever repay you?"

Almost as soon as she said it, I could tell she regretted it even without my glasses. In her excitement, she had forgotten about the fact that our sex moratorium had ended, opening the door to our possibly fucking once again. I knew she had decided that I wasn't a long term-solution for her, and she was right. Being Jessie, she didn't want to invest time in me if I wasn't going to lead to anything permanent. But now she had said it, and we both knew that there was something she could do that, while it may not repay the favor, would at least be appreciated.

"I supposed there is something I can do, isn't there?" she said. I hadn't said anything. Her face wore an expression of resignation as much as anything; it wasn't going to kill her to at least blow me, even if it wasn't in her plans. She slid down to her knees, with my feet between her legs, and started to free my cock from its restraints.

Jessie gave outstanding blowjobs—probably the best I had known before I met Julie. She was very active with her mouth, used her tongue to stimulate the penis while it was in her mouth, and could take quite a lot of it at once—I suppose her neck was long like the rest of her, so her gag reflex might be further back or something.

My dick now free, she stroked it in her hands a few times to get it started. She glanced up at me briefly, as if to say "I hope you enjoy this," then started to suck. It jumped to full hardness once I felt the soft, moist tissues of her tongue stroking the underside of my dick. She didn't take it all the way in at first, perhaps building up to it in some way, but eventually almost all of my dick disappeared when she bobbed her head down.

I didn't have anything to do with my hands, so I pulled up her jogging bra so that her breasts were free and held them in my hands while she sucked me. She might not have been completely gung-ho about blowing me, but her nipples showed no such hesitation in reacting to my touch.

She peered up at me, watching my reaction to her work. She stopped sucking to lick my dick, then kissed my balls while stroking me with a gentle hand. Then she pushed my dick as far down her throat as it could go, holding for a moment, before sliding it back out and continuing to suck, faster than before. Her sucking would have brought me to orgasm eventually anyway, but with my hands full of her wonderful, toned yet naturally soft breasts I climaxed soon after I started to touch them. But unlike Julie who swallowed every drop, Jessie pulled her face away once she felt me achieve that extra-hardness and stroked the orgasm out of me with her hand. Fortunately there was a Kleenex box on the coffee table behind her or she would have made me get cum stains all over my own shirt. But it was a darn good blowjob nonetheless.

Jessie hugged me again after I came, but it was a hug of gratitude, not a hug of affection. I found myself having little interest in kissing Jessie even though she just made me cum.

She stood up and pulled her shirt back down.

"Mmm, that was nice," I said, feeling the need to break the silence somehow. "And now you're now well on your way to being Dr. Jessie. Since I won't be around to see you defend, I'd like to take you to dinner tonight to celebrate your accomplishment."

"You won't be around?" Jessie asked. Again, no glasses to confirm her thoughts, but I had sensed that she was hoping I'd be around in case she needed help with any part of the dissertation process.

"Well, I suppose you might luck into me like you did today, but most likely I'll be working underground somewhere and you won't be able to find me." I said. "I wouldn't count on it."

She was torn now. Having me around meant that she might have to put out a little, but it also made her feel more confident in her ability to finish.

"Oh, don't worry, you'll do fine. You know what you're doing." I really did want her to finish, "So, what's the in-place to be in town these days?"

"Well, the buzz is about a new place called Nick's Martini Time," she said. "Its supposed to have first-rate martinis as well as great food. But I can't afford it, so..."

"So it's the perfect place for me to take you then," I interrupted. I pulled the wad of Franklins that was my current living money out of my pocket and flashed them to her, saying "Money shouldn't be a problem."

If she had had reservations about going to dinner with me, the chance to check out Nick's overwhelmed it. "But I don't suppose I can go there dressed like this. I'll run home and change, then come back—what, around six?" That should also give her a chance to shower and change.

"Okay, six," she said. "I'll call for reservations, otherwise we might be waiting a long time."

"Great, I'll see you then," I said.

"Oh, you should know that they also have dancing," she said.

"In that case, better make it 7," I said. She smiled at the insinuation that she would have a chance to dance there too. I showed myself out.

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I had never seen Jessie the way that she was when I picked her up. Usually wearing minimal makeup, that night she was completely done up. Usually she would show skin only unwittingly, a side effect of clothes not being tailored for women of her height; that night she showed skin by intent. She was wearing a halter-necked white dress with a plunging neckline and almost no back. She wore a red belt over it with red pumps to match. Her long straight hair was down and radiant. She was dressed for a night on the town, that was for sure.

As I would have expected from Jessie, however, she was all business first. The restaurant was very nice and certainly hopping; we had a quaint little table for two. Jessie was feeling out whether I was serious when I suggested that price didn't matter; I told her to have whatever she wanted. She ordered an expensive entrée and some blue martini-like drink. Then she peppered me with questions about her dissertation for at least a half-hour; our food had been served and mine was half-eaten by the time she finished her inquisition. But it was obvious when she was done, because she sighed heavily and looked as though a giant weight had been lifted from her shoulders. I guess she had decided right then that she could and would get this done after all, so now it was only a matter of getting it done—and Jessie was very good at getting things done.

I had thought that part of Jessie's strategy may have been to monopolize the conversation so that it didn't get too personal and possibly sexual. Thus I was surprised that, once the sense of relief set in, she was actually quite open to discussing herself and her personal life—I guess with all the professional mentoring I had done with her, she trusted my opinions generally, although some would argue that the fact that I had slept with her made me unworthy of such trust. I ordered her a second drink—I didn't ask if she wanted it—and eventually a third. She told me she had been spending a lot of time at school, trying to figure out what to do with her dissertation. She laughed for a second, saying "Actually, one of the newer students in the program is very interested in your area; I know he's read most of your old papers and after he learned I did an externship with you he asked me all sorts of questions about you. I told him that as far as I could tell, you had disappeared off the face of the earth."

"Yeah, its probably better that way," I replied.

She continued about having dated a few guys since I had encouraged her to dump her loser ex; for some reason she felt it important that I know that she hadn't slept with most of them. I wasn't wearing my glasses; Jessie didn't have any secrets I cared to know. I did remember, however, that Jessie was extremely sensitive in the back of her neck, and you could get her quite aroused if you could get your hands on it. I didn't specifically intend to try to bed her, after all she had just given me a nice blow. But if the opportunity arose, I knew how to take advantage of it.

Whatever she was drinking must have been pretty strong. By the third drink, her tongue loosened up considerably and she started to tell me her opinions on all kinds of things. She may have been my student once, but I had a lot more in common with Julie than I did with Jessie. She wasn't slurring or anything, but it was a good thing she wasn't driving home.

I suggested we check out the dancing.

I paid our check and we went to a downstairs dance floor. I was surprised to see the dance floor already quite active at that hour. I ordered us each another drink, then after watching for a little I asked her to join me on the floor.

Jessie liked to dance. But she was a serious-to-a-fault, busy graduate student, and she just didn't do it very often—and so she really wasn't very good. She was also so tall, it was probably hard to be graceful. Good thing she was hot, because none of the men watching her cared whether she could dance or not. I did a few steps that Julie had taught me, and once she picked up her jaw from the floor at the fact that I knew the latest dance moves and she didn't, she started to copy them from me. Dancing also made her thirsty; she was now drinking way too many blue things. But since she didn't get out much, she didn't want to waste a minute of it by slowing down.

By midnight it was time to take her home. She was completely inebriated; I had caught her a couple of times having to take a quick extra step to avoid falling over on the dance floor. Then they played a song that was a good one for a girl to grind her ass into her guy to; Julie had done so to me with that same song back in Vegas. Jessie saw a few girls do it, so she turned her back to me and started to lean towards me—but rather than push out with her ass, she pushed back with her shoulders, leaning on me. She tilted her head back, which caused a sudden rush; she now needed to lean or me or she would fall over. I held her up, shifting from side to side in my best attempt to keep with the rhythm while holding her up. Her bare back felt good leaning against me. It was right there, I had to take it: I ran my hand slowly up her bare back and up to her neck. I could tell right away when I hit the sensitive zone; she closed her eyes, made a breathy noise and tilted her head upwards, as if to embrace my hand as it touched her neck. I brushed the hair away from her left ear and gently gave it a nibble while I touched her neck in a way that was half stroking, half massaging. She looked as if I was already inside her; I needed to get her home fast, for more reasons than one.