Gifted Grifter Ch. 03

"Um, no one has ever asked me to stay before; I'm used to leaving hotel rooms at 3 in the morning..." she said.

"Yeah, I know, but I've been sleeping alone for a long time now, and this way I'll have you there first thing in the morning...AND I won't have to eat breakfast by myself. That is, you will let me buy you breakfast at Paris, the best breakfast in the world? It's not like there isn't enough room for four in that friggin' King bed." I could tell she wasn't quite comfortable with the thought. "Tell you what, I'll give you an extra grand to cover your time." I had an ulterior motive of course; after I fucked her brains out, I planned to pick them (her brains) for what she knew about the best places to find big money poker games. At her going rate, she would know where the money was to be found.

She said she had to make arrangements first. She called someone—not a pimp, at her price she worked for herself, but rather a lawyer she retained to make sure she didn't suddenly disappear and to bail her out when she got busted. My glasses told me she was telling him that she was staying at Planet Hollywood for the night and to start looking for her if she didn't call him by 10AM. Then she hung up and said, OK, she'd give it a try.

That was good enough for me. I grabbed a cab to take us to Planet Hollywood.

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Up in the room, she put down her purse, ran fingers and their long, red fingernails through her hair, and took a seat on the sofa.

I called room service for a couple of outrageously overpriced Martinis. "I promised you a drink," I said, "and a drink you shall have." While we sipped them, she asked me what I liked. Good thing she didn't have mindreading glasses on, I generated quite a lengthy list of ideas. I did have my mindreading glasses on, and they told me what she wouldn't do: no bondage or anything kinky that might make her feel unsafe, anal sex an extra two grand. Her thoughts gave me an idea.

"Oh, I'm pretty boring I guess," I said, "certainly nothing involving pain. But I do kind of like to be in control; I have an idea, if you can do a little playacting..." I had finished my drink and was walking towards the room safe. Screening her with my back so she couldn't see the combination I picked, I pulled out 3K and put the rest in the safe. I also took off the thick rubber band the cashier at Luxor had used to hold my wad of bills together.

When I turned back to her, she was finished her drink, thinking "that's what they always say before they ask for the really weird shit." She was already a little nervous about being asked to stay the night.

"OK, here's the scoop. I'd love to handcuff you to the furniture and make you do whatever I want. But that would be asking you to take an awful big chance to trust me like that, and it seems I'm already asking for things that are quite unusual. Not to mention, I don't carry handcuffs with me everywhere I go. So here's my idea: see this rubber band? Do you think you could PRETEND they were handcuffs? If you get uncomfortable with the way its going, just pull your hand free and I'll understand."

She was thinking this was pretty silly, but then again she'd seen a lot of strange requests. Besides, it was a novel way to play out a domination fantasy without her having to actually be physically restrained and risk getting beaten up. What was concerning her most, actually, was that I was going to get emotional on her, that I was confusing paying for sex with having a girlfriend. She certainly wasn't used to a john giving any thought whatsoever to what she might be thinking or feeling during the transaction.

Nevertheless, she decided to play along. She put down her glass and offered me her hands. She put on a pouty expression, and said, "Have I been bad, master?"

"Yes, you have," I smiled, then took off my glasses. I took her hands in mine, pulled her to her feet and walked her to the middle of the room. Then I gently helped her hands gather behind her back, and "cuffed" them together with the rubber band.

She stood there with downcast eyes, playing the part of the repentant servant. Excellent.

"I am displeased," I began, slowly walking in a circle around her, touching her here, there and everywhere. "that you have forgotten your training."

I stopped right in front of her and pulled her top up over her breasts. It was tight enough that it stayed there, fortunately. I took one of her nipples between each thumb and forefinger and squeezed them until they were erect, but not so hard as to cause pain—I was only interested in control.

"Now you know that when I come home, you're supposed to be kneeling on the floor, waiting for me," I said.

"Like this?" she asked, kneeling down on the floor.

I grabbed a pillow off the couch and threw it on the floor in front of her. "It is acceptable to kneel on a pillow," I said, nodding that she should kneel on it rather than on the hard floor, "but otherwise yes." She scooted forward so her knees were on the pillow.

"Like this master?" she asked, acting like a slave eager to learn her duties.

"And what are you to do while you are kneeling?" I asked. I figured she could probably guess, but just to be sure I rubbed the side of her cheek with my first knuckle.

"Open my mouth, sir?" she asked, forming her mouth into an O-shape.

"Yes, open your mouth," I answered, unzipping and unbuckling my pants and letting them fall around my ankles, then pulling my shorts down too. She looked up at me while holding her mouth open for my penis; I slipped it in between her lips. She sucked it like a pro (of course she did, she was a pro). She used her tongue to entice my dick while it was in her mouth, and was able to take almost all of it in at once. I held her head lightly and pushed my penis deeper, fucking her face—but not to the point of forcing it down her throat. Who the hell decided that making a girl gag is sexy anyway—it isn't! As far as I'm concerned a penis is a guest in a girl's mouth; it should be mindful not to wear out its welcome. It doesn't matter that I was paying good money for this, hooker or not she was still a person and people don't like to have things forced down their throats until they gag.

She didn't know how I feel about gagging, of course, so she tested me a little by pushing back against my hand to see if I would let her take her take my dick out of her mouth. I think I surprised her that I immediately let go, letting her disengage from my cock and letting her breathe. She then put it back in her mouth, deeper this time, apparently willing to suck it deeper with the knowledge that I wasn't going to force it in farther than she could take it without triggering her vomiting reflex.

Man it felt good. She was taking it as far as she comfortably could, so I let go of her head, reached down and grabbed her nipples with my fingers. I let her suck for quite a while, playing with her tits the whole time.

Finally, I pulled my dick out of her mouth and indicated she should rise. I stepped out of my pants, took of my shirt, and walked her over to the bed. I undid the rubber band, reached under her skirt and pulled off her thong, then motioned for her to lie down. When she was lying on her back in bed, I took her hands in mine gently guided them up over her head, on one either side of the post of the headboard, and then "handcuffed" her to the headboard with the rubber band.

I straddled her hips and ran my hands up and down her torso and her breasts. Then I slid beside her and pushed her skirt up to her hips. She was completely shaved. She let her legs fall slightly apart and I put my finger in between them. I realized she wasn't wet; not surprising, this was my fantasy not hers. I supposed she would normally masturbate to get herself ready while doing whatever her customer asked for, but with her hands "tied" she hadn't been able to do that. Easily fixed, I thought.

She started to pull her hand out in order to manually prepare herself, but I instead moved forward, straddled her shoulders, and thrust my penis towards her face. She reached for it as best she could; she could lick it and put its tip just into her mouth, but she couldn't take it deep at the angle I was at—because I was arching over backwards, reaching back with one hand and rubbing her pussy.

"You must be prepared before you can receive the master's special gift," I declared with false pomposity.

"As you wish, sir," she mumbled between slurps of my junk, spreading her legs wider to allow to me to better reach her. She closed her eyes, but rather than closing her eyes to enjoy the sensation like a lover might, she closed her eyes to fantasize about something that got her hot, helping her get wet faster. It must have worked, because I started to feel the dampness growing.

I stood up next to the bed, laying my penis lengthways across the length of her lips. She kissed and licked it; I rubbed her clit a bit more. At that point she did slip her hand out of the rubber band, reached for the nightstand, and took a condom out of her purse. She sat up, stroked me a few time for maximum erection, then slipped the condom on my dick. Then she lay back down and put her hands back where I had put them. I slipped the rubber band back onto her wrists, then announced "Make ready to receive the Master's special gift." She spread her legs far apart for me.

I knelt between her legs, put one arm on either side of her, and slipped my penis into her. The condom took away a little of the feeling, although it would have been worse had they not been ultra-sheer. But she didn't get to charge 3G a night for nothing; she contracted her muscles so as to squeeze my penis while it was in her, making her vagina feel much tighter than it actually was. A nice trick, I thought, wish I could teach that to other girls I've laid. Her breasts bounced just the right amount with every thrust her body absorbed. She kept her eyes closed now; I supposed it helped her concentrate on maintaining excitement while a stranger was lying on top of her. Nevertheless, she was beautiful, and I enjoyed just watching her body under mine while I screwed her. Eventually I exploded inside the condom.

I collapsed on the bed next to her for a second, then pulled off the rubber and rolled over. She had pulled her hands back and was lying on her side next to me, just kind of looking at me.

"Are you sure you still want me to stay?" she asked.

"Yes," I said, "and I had bigger plans for tonight than that, but you're so good I'm spent after just one."

She laughed at me and ran her finger down my nose. Then she got up and went to the bathroom to wash up. After a time, she came back to bed. She had ditched the tank top, skirt, and shoes, but had put her thong back on to sleep. I smiled at her as she slid under the covers. Then I turned out the light on my side and went to sleep.

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I woke up before her, but my stirring awakened her almost immediately after. The bed was so big, neither of us had affected the other's sleep in the slightest. She turned towards me now and reached for my penis—I had slept naked—under the sheets.

"Ooh," I cooed, "that feels good."

"Does it?" she teased. She kept stroking it until it was fully erect, then whipped the covers off the bed. She knelt on the bed, made a show of playing with her own nipples until they were hard, then bent over and took my penis into her mouth. I let her do her thing this time rather than dictating. I put my hands under my head at first, then realized my right hand could reach one of her tits so I played with that, letting her blow me all the while. She sucked me to orgasm with great efficiency.

Satisfied, I grabbed a quick shower and dressed. She passed on the shower—I was sure she preferred to save that for when she got home. I realized she only had her clothes from last night, which were not normally the kind of thing someone would wear first thing in the morning, plus they were now somewhat wrinkled from my having scrunched them up while I was screwing her the night before. I offered to take her to Lucky at the Desert Passage and buy her some casual clothes for breakfast, but we would have had to wait until they opened at 10. She preferred to go right to breakfast. I gave her $3200 and we headed to breakfast. She checked in with her lawyer/protector on the way.

As I promised, I took her to the breakfast buffet at Paris. I wasn't surprised to see that she didn't eat very much—if you livelihood depends on your body, you can't afford to get fat. She did seem to like the fresh crepes, though. She was worried that I would ask her stuff about her personal life during breakfast; she was all too happy to tell me about where to find the guys with the biggest money and the best high-stakes poker tables instead.

After breakfast we parted ways in the walkway that connect Paris to Ballys. Inspired by my surroundings, I bid her adieu with a kiss on each cheek, like the French do. She asked if I wanted to exchange phone numbers in case I was lonely again sometime; I had hesitations, but I knew that I would be keeping a phone number for no more than three months at a time so there didn't seem to be much harm. After we exchanged numbers, she headed one way and I the other.

As I strolled back to the main casino floor, I had no idea what I was going to do with myself all day. When I went to Vegas for fun, I would hit the tables as soon as possible and work on tying on the biggest buzz I could. But I needed to be sober now that I was basically playing professionally, and I wasn't willing to blow the money I had just earned on a game where the house held the edge—I'd already blown almost half my winnings on Heather. It wasn't worth playing yet, there wouldn't be big money at the tables until the evening, and the less time I spent at the tables, the less time that someone might start to eye me with suspicion.

As I walked by the base of the "Eiffel Tower," I heard a commotion erupt from the race and sports book area. With time on my hands, I idled over to see what the fuss was about. A couple of bettors were very happy; apparently a 25:1 shot had come in, and one of the guys even had the trifecta—paying out about $800 on a $2 bet.

"I told ya so!" the guy was crowing. "I'm telling ya, Idle Passage is a horse to watch!" That's when it struck me that maybe I could find a productive use for the daytime hours too.

I turned on my glasses and idled over to the crowd. There was a lot of talking—and a lot of jealous thoughts. A couple of guys started turning their attention to a race that was starting soon at Santa Anita. About three of them were thinking of betting the same horse, so I put five dollars on him too.

He came in sixth.

"Well, not off to a good start," I said randomly to the guy next to me. "I wish I had a good tip on some of the horses."

When I had said "good tip," the guy suddenly thought "Mirage Cloak in the fifth at Pimlico."

"Yeah, don't we all," he said noncommittally.

I figured it wouldn't hurt to put something down on Mirage Cloak, who was showing at 13:1. I lost a couple of small bets waiting for the fifth race at Pimlico, but put $20 on Mirage Cloak. Sure enough, he came in, so I was up over $200.

I spent the next couple of hours doing the same thing. Some of these guys knew their stuff; they had contacts, did research; some of these guys were here every day because they were able to make living betting the ponies. I would just pay attention to their thoughts as they chatted or chat with them myself; their minds couldn't help but give away their best inside information. I still lost more often than I won, of course, but I later hit a nice trifecta and a few smaller wins too. I also ran into a guy who had inside information on a key unannounced injury on one of the nights games; I bet against that team. I was up two grand before I even entered the poker room.

I knew the big money would be at Caesar's, but I expected to rely on that facility in the coming months, I didn't want to ruin it while I was still learning the ropes. I chose Bellagio instead: just as much money, not as much skill. Being Saturday night, of course, the place was jammed with guys eager to give me their money. I sat at a table at 6:00, and I was up 15K when my phone rang at 10:00.

I had to fold my hand to answer my phone, which was fine because I had just been dealt 9-5 unsuited. But I couldn't imagine who would even have my number to call me, so I looked inquisitively at the display. It said "Heather." Now why would she call me?

"Hello?" I asked, not knowing what to expect.

"Hello, Tom, this is Heather," said the voice on the other hand, trying to sound as breathy as possible. "You'll never guess where I am."

"Please tell me it's not District Police HQ," I said.

"No, thanks to you. I was sitting in the bar at Caesar's when that same guy from yesterday came in," she explained. "So now I'm walking down the strip, but I don't have any destination in mind. So I was thinking—are you going to want a companion for breakfast tomorrow? No extra charge for the morning."

I now had plenty of money to rent Heather again, and the thought of having a nice warm pussy to stick my dick into was sounding real good right about then. So I did some quick thinking, and came up with a plan.

"OK, meet me outside of Jet at the Mirage at midnight. We'll talk." I said.

"That gives me a couple of hours—do you have any special requests?" she asked.

"Yeah...actually, I do...I think I'm in the mood for a sexy schoolgirl tonight." I said.

"All right then," she said, "I've got a little outfit that I think you're gonna like. See you then," she said, then hung up the phone.

I figured that gave me 90 minutes to make as much more money as I could before I went to meet Heather. Luck was with me; I ended up cashing out at 11:15 with 25K more than I started. Good thing that Bellagio, Mirage and Planet Hollywood were all easy walking distance from each other. I stopped by guest services at PH and for a fee arranged for them to transfer 20K into a debit card account for me, then I changed into better clothes and headed to the Mirage.

I got there about five minutes early. Heather wasn't there. I went and got a CC and soda—at least now I could drink too—and sat down to wait for her. When she wasn't there at midnight, I got a little annoyed—but girls sometimes take time to get prettied up, and often the ones that take the longest are well worth the extra time. It was almost quarter-after when she arrived, and as soon as she did I knew that she had been late on purpose: she hadn't wanted to stand around waiting outside the club wearing the outfit she had put on for me, and I didn't blame her.

Heather's sexy schoolgirl outfit was right out of strip club fantasy. She had on a plain white shirt, but it was tied up together right below her breasts to expose all of her flat tummy. None of its buttons were buttoned; she had on a fancy, meant-for-external-viewing black bra underneath in order to avoid arrest for indecent exposure. With is, she wore a red plaid, pleated skirt that was maybe 8 inches from top to bottom; her butt cheeks poked out the bottom when she walked, and you could catch glimpses of her thong too. The best part was the white thigh-highs she wore, ending a good six inches below the bottom of her skirt. Black, clunky shoes with high heels completed the look. My erection went from zero to sixty in 0.2 seconds.

She spotted me and headed my way. Every man within 100 yards of her turned to stare.

"So what's the plan?" she asked, exaggerating the huskiness of her voice.

"How about a dance?" I asked. "I'd like to take you to with me to Jet over there...if that's all right with you. I don't know if that's somewhere where your friends might hang out, and I wouldn't want to embarrass you by being seen in there with me if they were."