Debbie's Gambling Debt (Closed)

[debbiev]

About me...
33 years old, single, never married, 5'5", 128 lbs, long curly brown hair and brown eyes. Curvy 36d and a bubble butt. Tan complexion.

A couple of years ago I had a bit of a gambling problem. But I'm over that now, well going broke kinda helped with my problem. Hard to gamble with no money. I loved playing poker, I even won sometimes and actually supported myself for awhile. I knew most of the men and when things got tough, they were always quick to lend me money, I guess they felt sorrow for me or wanted to get in my pants, which they never did. It wasn't a charity thing because I always signed IOU's and sometimes made very small payments on the IOU's. Enough to keep them all at bay.

On one particular bad losing streak that lasted two weeks, my debts piled up into the tens of thousands. Owing most to one man, but there were smaller amounts owed to a few other men too. No way could I ever pay them off. I only had one option left, run.

At 3:00 AM, I get out of bed and get dressed, wearing: navy blue tank top, beige shorts that fit me tight, light blue bra and light blue bikini panties. Beige sandals.

Packing up my shit and I get in my car and just drive south. Having no idea where I'm going, but far enough so no one knows me. Maybe I'll live in the country and work on a farm or something. Who knows. All I know is I intend to start over, debt free and no one on my ass bothering me, well more like threatening me for payments.

Not making a lot of money gambling I don't drive the best car, my 2006 White Honda Accord usually gets me from point A to B. It's 1:30 PM and I pull off the interstate as my car just isn't sounding right. Driving about 15 miles looking for a gas station, nothing. All I see is farms. Smoke begins to pour out of the hood, "Fuck, here? Fuck."

I pull over as my car dies. Nothing around but huge farms. Seeing a silo maybe 2 miles away, figuring I'll stay here for about an hour or so and if no one comes by I'll walk towards the silo, has to be life there. I lift up the hood and stand outside my car. It's sweltering out, has to be over 100 degrees, not a shade tree in sight, makes sense as this is the south.

Standing there and looking both ways for a car or truck. Nothing. I check my phone, no signal. Oh my god, you have to be kidding. About 50 minutes passes and I begin looking at the silo, figuring I'll have to begin my walk to it, better then standing here drenched in sweat.

 

[cliteatingman]

About me...
David, 55 years old, divorced. No kids
5'8" 175 lbs. Curly brown hair. Touch of gray.

I used to have a corporate desk job. It paid decently, let me put my wife in a nice house, let me dress expensively enough to convince some women I was rich and it had some national and international travel. The travel was what eventually ended my marriage. If you are halfway attractive, dress well and willing to splurge a bit on a night out, women will offer themselves to you despite the obvious ring on your finger. I took advantage of too many of those offers for my wife's taste and let's just say that she is still living in that house I bought, but I am not.

A few years before the divorce I got into the business of buying up hard to collect debt for cents on the dollar and collecting it. It started out as a way to make a little money on the side. Eventually, I made enough that I was able to retire. Around the time of the divorce I started getting into less well documented debt. The advantage of this was, it was easier to obtain the money in ways the divorce court and the IRS couldn't track. I didn't have to share with either my ex or the government. The downside was that courts would not enforce these debts, so I had to rely solely on my ability to scare the debtors into paying me. Six months ago, I discovered a whole new angle on the business. I was trying to collect the gambling debt of a drop dead gorgeous southern belle. (There are quite a few of them in my part of Virginia.) She had no money and little prospect of getting any. I was about to write it off as a bad investment, when she started begging me to accept her as my sex slave until I considered the debt paid. Over the next month, she had more orgasms than I did, but I was always in control. Since then, I have pursued mostly women's debts, with an occasional male debtor with a relatively large and easier to collect debt.

Recently, I had acquired a $100,000 IOU from a chick named Deborah for $3000. The last name was illegible on the IOU She had apparently racked up a huge gambling debt and disappeared without a trace. It was rumored she was in Virginia but no one had any evidence. As I pulled my black Mustang over the next hill, I saw the cruvy silouette of an attractive young woman standing next to a car. I slowed down...

 

[debbiev]

My Ride, Thank God

Standing there sweating in the ridiculously hot sun, waiting for someone to come by. Feeling sweat rolling down my back to the waist of my beige shorts. Below my waist you don't wanna know the places I'm sweating. Now getting seriously thirsty.

Just as I'm about to give up on a car coming by and begin my two mile walk I see a black Mustang heading in my direction. I smile and blurt out to myself, "thank you god, thank you".

I see an older gentleman which is perfect, I mean it's better than a bunch of rowdy country boys puling up. He looks kind of distinguished and I get a good feeling from him. I wave my arms and he begins to slow down. He pulls up behind my car and I walk to the drivers side of his car. I smile, "I'm so glad to see you, I'm Debbie. My car broke down and I'm hoping you can help me out"

 

[cliteatingman]

Standing there sweating in the ridiculously hot sun, waiting for someone to come by. Feeling sweat rolling down my back to the waist of my beige shorts. Below my waist you don't wanna know the places I'm sweating. Now getting seriously thirsty.

Just as I'm about to give up on a car coming by and begin my two mile walk I see a black Mustang heading in my direction. I smile and blurt out to myself, "thank you god, thank you".

I see an older gentleman which is perfect, I mean it's better than a bunch of rowdy country boys puling up. He looks kind of distinguished and I get a good feeling from him. I wave my arms and he begins to slow down. He pulls up behind my car and I walk to the drivers side of his car. I smile, "I'm so glad to see you, I'm Debbie. My car broke down and I'm hoping you can help me out"

Sure I say. Nearest gas station is two miles. I could take you there. Tow truck service is 5 miles away, I could drop you there. My house us ten miles away. I live alone and have a guest bedroom. Your welcome to come to my place. We can call a tow truck from there. You can shower and change and I'll get you some food. What's your pleasure Debbie? I am David Smith. You can call me Dave.

 

[debbiev]

The Ride To...

You are super nice to me, I mean even offering me to stay at your house. Of course the old beware of strangers does cross my mind. But you are older, distinguished and so polite. And this is the countryside, people are all pleasant here, unlike the city. At least that's what seems to be true.

"Hi Dave, um, yes, thank you for the invitation to go to your house. I can call the gas station from there and if they can't tow and fix my car before the end of the day I suppose I can stay overnight. I seriously appreciate the offer" I give you a wide smile and feel relieved that you have kind of rescued me from being in the middle of nowhere.

I get my suitcases out of the trunk of my car and with your help put them in your cars trunk and we drive off. Feeling comfortable with you, as I ask you questions, "It's so far from anywhere out here, how long have you lived here?"

 

[cliteatingman]

Before we drive away. I get out my GPS and not the exact location so we can send it to the tow truck, since there are no obvious landmarks. Answering your question, I say, "I used to have a corporate job and live in Richmond with my wife. She got the house in the divorce. I went into a business that I can do from anywhere and moved out here where I could get a nice tract of land and build a house without spending an arm and a leg. If you're hungry, I can make some food while you shower and change. What do you like to eat?

 

[debbiev]

The Conversation While Driving to Your Place

Your answers to my question just confirm that you are established and confident in what you do. Although building a house out here in the boonies is a bit odd, being you live by yourself. But maybe you're a loner.

"Well that's cool that you can live our here and have your own business. I lived in the city for years and just had to get away from it all. So I'm starting anew out in the country, figuring why not give it a try" I smile at you, hoping you don't think I'm some kind of ditzy nomad, or worse yet on the run from something or someone.

"Sure I would love something to eat and get cleaned up, it was hot out there standing by my car for almost an hour. You were the first car to come by. Thanks again for helping me out"

 

[cliteatingman]

"My pleasure!" I say, with just a hint of a wink. It is nice out here, not much light pollution. Beautiful stars at night. Richmond is a little over an hour away so I can always catch a show or get a good meal. That reminds me. Hamilton finally hits Richmond this weekend and I have an extra ticket. If you care to stay around that long or if your car doesn't give yiu a choice..."

 

[debbiev]

A Date Or A Possible Opportunity For Me?

As you offer to take me to see the play Hamilton in Richmond this weekend, I hesitate. My mind races though thoughts, like, it's weird you happen to have an extra ticket, I suppose even if you don't and you probably plan to buy one. So it will be kind of like a date.

You are quite a bit older than me, but well, why not give it a try for a few reasons. Some being: You seem really nice and pleasant. You are established and seem to have money so that's always a good thing, I can get free room and board at your place, plus maybe you have connections out here and I can get a job to support myself. Then again if I stay at your place, maybe I don't need to look for a job. That decides it, what do I have to lose?

"Sure I would love to go see the play Hamilton with you. I've heard so much about it. Thank you" I give you a big smile.

 

[cliteatingman]

"Great!" I say, "It's a plan. I'll get us reservations at a nice restaurant beforehand and I'll make sure there is a nightcap waiting for us here. What would you like for lunch? I keep a well-stocked fridge. I have everything from leftover pizza to lunch meat for sandwiches to salmon mousse. All gourmet and delivered overnight in dry ice from the best specialty stores in the country. Your wish is my command."

 

[debbiev]

Now Dinner, a Play and a Nightcap? Hmm.

You quickly add dinner out and a nightcap at your house to the plans. It's obviously a date now. But I suppose why not.

"Salmon mousse? Never had it so if you don't mind I'll be daring and try it." I laugh a bit.

"You know Dave, you have a way of making me feel comfortable. Thank you for that. You are kind of my hero rescuing me from being stuck in the middle of nowhere in the blazing sun, so thanks for everything so far."

 

[cliteatingman]

"It's my pleasure!" I say again. The wink becoming more niticeable. "I'll get the salmon mousse out for you. Have a nice long bath or shower. Your bedroom has a private bathroom. Take as long as you want." As you disappear into your bedroom and close the door. I pull out my phone and tap the "hidden bathcam" icon. You enter the bathroom, which has a luxurious bathtub with jacuzi jets, and a massaging showerhead. You have no idea that I am watching you.

 

[debbiev]

Debbie Gets Settled In, Maybe Too Settled?

I notice your obvious wink and just give you a half smile back. It's almost like you are flirting with me. Well I suppose you are and you have sexual thoughts on your mind, I mean you are taking me out to dinner and a play soon.

Your house is beautiful, it seems to have everything. I could definitely get used to living here and just kinda enjoying the luxuries of it all. Plus I don't even have to gamble for money, not that I have any money left. But I'm certainly not paying any of my debts back, even if I did get some money. Those guys can all screw themselves.

I head up to my bedroom, it's seriously perfect, it even has a private bathroom with a massaging shower head and a Jacuzzi. Also a view of the huge backyard with a pool, a manicured lawn and landscape and then acres of woods behind it. Wow.

I remove my clothes, glad to get out of them all. Leaving them all on my bedroom floor. Then I head into the bathroom and in the shower. Figuring I'll shower this time since you are preparing food for me, I don't wanna take too long. Looking at the massaging shower head and getting ideas of using that on myself when I have more time, yes my mind does tend to be in the gutter. Well I have a vibrator and my magic wand in my suitcase. You should only know huh? Anyway, now I'll just shower and get dressed. I wash my hair and soap myself up and rinse off.

I step out of the shower and dry myself and head back to my bedroom, letting my hair air dry. I look in my suitcase and pull out some clothes to wear back downstairs...White stretchy tee shirt, jean shorts, white bra and white low cut bikini panties. I slip my beige sandals back on and head back downstairs. Figuring I'll unpack everything later.

I walk into the kitchen and see you standing by the counter. My hair is still wet and curling. I smile at you, "Hey Dave, I just wanna thank you again for all you've done for me"

 

[cliteatingman]

I was hoping you would take more time in the shower, but the camera in the drain did get me a nice view from below and the camera in the massaging showerhead got me some great closeups... And it is all recorded.

You come back down. You are not used to seeing china and silver on the dining table for lunch. The salmon mousse is in an exquisite serving dish. There is a basket, with white, wheat and rye bread, all delivered fresh from the bakery and a garden salad with vegetables picked this morning.

"Have a seat, please." I say. "Can I get you some wine, water or both?"

 

[debbiev]

Lunch in Luxury

I sit down, "I'll just have a glass of water". Not wanting to cloud my head with wine so I can learn everything about you. This all seems too good to be true. I mean I was just driving, basically on the run from my debts, I have no where to live, almost no money, and you meet me on the side of the road by my broken down car and then take me to your beautiful house, well, actually a mansion.

I look at the table settings, fine china and silver utensils. I look at you and smile, "Wow Dave, the salmon mousse looks delicious, I've never had that before" Hoping you don't judge me for saying that. It has to be obvious I'm not even close to the upper class level as you as. I mean I gambled for a living. So basically I lived winnings to winnings, until my luck went seriously bad. But hey I can get into living here in these riches. A woman of luxury, yep I can get into that.

I dig into the food, hoping I don't look too lower class. Eating the salmon mousse, having rye bread and the fresh salad. I smile at you, "Dave this is so perfect, thank you so much, I totally appreciate everything you have done for me"

As I finish up my lunch, "I guess I'll call the garage and ask them if they can tow my car and fix it, I just hope the repair and towing bill isn't too high, do you know a garage around?" Hoping you offer to pay for it. Knowing it's not right to do that, but screw it, you like me.

 

[cliteatingman]

"I have a personal mechanic. I will call him and you won't have to think about the car until it is fixed. I will text him your car's location, which I recorded on my GPS. In the meantime, enjoy lunch. I told you a bit about myself. Please tell me about you..."

 

[debbiev]

Debbie's Long String of Lies

I hide it well, but inside I'm like yes!!, as I see you fall for my plan of making you arrange and most likely pay for my car to be towed and repaired. Loving that you took the bait. Imagine what else I can get from you.

"Oh about me? Such an open question, where shall I start?" Knowing if you knew I gambled for a living and got off on winning money from other people, well you would probably hate me. Plus that I never paid any of my debts back, screw them. Add to that my ghetto upbringing, it would make you hate me even more. God you and I are so fucking different. But I hide all that shit well and can come off as the normal leveled headed middle class girl next door.

My lies start, "Um...okay Dave, well I kinda come from a middle class family, you know the house, picket fence, my Dad working and my Mom having a part time job as she raised me. Yeah...nothing exciting at all. I graduated college and I worked in an office for years, an advertising firm in the city. I got my own apartment. But it wasn't enough, I wasn't happy with my life. I mean I liked my job but I knew I wanted something different, so I decided to just start over and live in the country. And so here I am." I give you a big smile, hoping you bought my pack of lies.

Absolutely zero of what I just told you is true, except that I want to start over and live in the country. But looking at you it appears you believe every word I said. It's kinda fun fooling you, knowing it will only lead to me living a life of luxury. I think I hit the fucking jackpot with you.

 

[cliteatingman]

I thought to myself, "No details about the family. Nothing about what college. I wonder what she is hiding. Well, I'll give her a little of my background." To you, "I was born into a family that had money, but in Virgina, we weren't the right kind of family. My dad had worked in a textile mill as a young man and eventually got himself a management job and made money in the business. The right kind of family is descended from slaveholders... Or plantation owners, as they say. Well, I did what I was supposed to do. I went to UVA, where I met and got engaged to a woman from the right kind of family. Every generation in her family had gone to UVA since Jefferson founded the place. My parents helped me buy an ring that was both expensive and tasteful enough to convince her family that I wasthe right guy. When she took me to meet them, she warned me that her father would quiz me on the history of UVA. Studying for that exam was harder than anything else I had done in college. I figured after I got the engagement ring on her, she would go to bed with me, but apparently women from the best Virginia families still save themselves for after marriage, so I had to... But I am droning on a bit. Let me just say that only one of us married a virgin onour wedding day and she never wanted to go beyond strict vanilla. That was not the only reason we eventually got divorced, but it didn't help..."

 

[debbiev]

Soon To Be An Elitist, Me?

I listen as you tell me about your rich family history and that you married into a rich family too. It doesn't just sound rich, it sounds way beyond that, more privileged for generations. You obviously following a long line of elitists and of course wanting to continue that, despite your divorce.

I'm surprised when you go on to tell me about your ex wife wanting to be a virgin up to your marriage and that your sex life was vanilla. I mean you just met me and you are referencing your sex life. Just hoping that isn't a tell that you want sex with me and it being more than vanilla. But hey, I'll do what I have to get what I want. But it will be under my terms, not yours. I mean this is such an opportunity for me, I know you are crazy about me and I basically have you wrapped around my finger. Oh god I'm gonna be so fucking rich soon. Fuck gambling and fuck my past trashy life, I'm gonna be rich and an elitist soon.

"Oh wow Dave, you have such an interesting life. As for your divorce, I suppose things sometimes work out for the best, right?" I smile, then add, "I mean you never know who's path you will cross. Hey you just met me and I already consider us good friends, so who knows where anything leads."

Knowing I'm playing into your desire for me, well I'm pretty sure you desire me. Oh wow, this is a chance in a lifetime for me. I'm so lucky.

"Hey Dave, do you mind giving me a tour of the house. Then I can give you my credit card and you can arrange to have my car towed and repaired. I really appreciate that." Knowing my credit card is totally maxed out, but then I also know you will offer to pay. But I did want to make the offer like I wanted to pay.

 

[cliteatingman]

I give you a tour of the house, showing off a lot of art and artifacts, some of it by artists whose names you have heard of. I make sure to state the price of each piece, but beyond that, it is unclear that I know much about it. The things that seem to be truly of interest to me are the wine cellar, the full bar, the pool table, the sauna the swimming pool, and the mini theater with the largest TV you have seen, surround sound and virtual reality. There is an easy chair in front of the TV and something you don't recognize in front of the TV, which it gradually occurs to you must be knee pads. As the tour begins to wrap up, I ask for your credit card. An expression of surprise crosses my face , followed by a brief smirk. Then my resting face returns. I excuse myself to call my mechanic from my home office...

 

[debbiev]

Debbie is Sold On Staying in the Mansion

I'm not an artsy person, but some of the paintings you have are obviously worth a huge amount of money as you don't hesitate to tell me that.

I love the wine cellar, it's just so cool to have that. Of course the full bar, pool table, swimming pool and amazing theater. A big smile crosses my face as I look at you, "Dave, your place is just perfect, I mean you have everything here. You know I love playing pool. I'm seriously good at it too. So we'll have to play some."

I played lots in pool halls and dive bars, I liked beating most guys at it. Hustling some of them. All part of my trashy lifestyle I guess. But I won't tell you that.

Thinking I can seriously get into this, a life of luxury, not working, being an elitist and well oh god this is just ideal. It's what I always wanted. I have definitely made up my mind, I'm gonna be your girlfriend, maybe wife and this is gonna be mine"

I look around a bit more and see knee pads in front of the TV, assuming they are for exercising while watching TV. I guess they are anyway. Kinda weird though.

"Oh yes, here's my credit card." I hand it to you and just hope you don't try to pay with it cause it's maxed out. I think you just wanted to see if I was going to pay for the towing and repairs, kinda like testing me. But you will probably pay for them, I hope anyway. But if you don't and decide to use my card I'll have to make some kind of excuse as to why it declined. Hopefully, if you want me to be your girlfriend you will offer to pay for the towing and repairs. I mean you are rich and you do want me, so it only makes sense.

You smile and tell me you will call your mechanic. "Okay, cool, I'll just wait around. I hope he can tow it today and fix it by tomorrow. But either way we do have a date to see the play Hamilton right?" I give you a wide smile as I stare into your eyes and move my hand up to my hair and subtlety brush a few strands back. I mean if you don't get that I am interested in you then you have to be blind.

 

[cliteatingman]

A few days pass and you hear nothing about your car... It is time for us to go to Hamilton. I take you to buy a new outfit before dinner. As we go theough the store and I make recommendations, you notice I like the most expensive fabrics, the shortest hemlines and the most revealing tops. I also insist on buying you aeveral thongs and push-up bras. After you try on several outfits, we agree on one . I pay more than you have ever considered paying for clothing and we go to dinner. We get chateaubriand steak for two accompanied by chateauneuf du pape red wine. I look you in the eye and say "With just a little help from me you are one HOT BABE!"

 

[debbiev]

Wow, Our Upscale Shopping Spree, Dinner and Play

Despite not hearing anything about my car repairs, I don't ask. Figuring I might as well enjoy my time here. Hopefully it's my home now, despite you probably not realizing I intend to stay here and live the life of luxury.

As you take me shopping and buy top of the line clothing for me I just can't thank you enough. When you insist on even buying bras and thongs, I smile, "Well I see where your thoughts are going, huh?" I giggle a bit, knowing where I intend to end up with you tonight after dinner. But only after and if everything goes perfectly.

We agree on the black form fitting spaghetti strap mini dress, it was definitely my favorite as it hugs my curves. Plus it shows off my 36d's with the U neck. We add a choker collar and that seriously finishes my look off.

The prices are outrageous, but it seems you don't flinch. The material just feels so good against my body. God I'm going to love being wealthy. I pick out a bunch of different color bras, low cut bikini panties and thongs. I smile at you as I pick out a silk thong for tonight.

"Thank you so much Dave, you treat me so well. I like being hot for you." I lean in and give you a quick kiss on the lips.

We finish our amazing dinner and are off to see Hamilton, I heard good things about it and I'm kind of a history buff, so I'm really looking forward to it. This is all going so well, I think I have my ticket to joining the elitists. Who would have thought ghetto me would end up here? I'm so fucking lucky.

 

[cliteatingman]

As we leave the clothing store, I am very pleased with myself. I am going to enter my favorite restaurant with a young, hot, expensively dressed companion. Men will look at you and be jealous of me. Women will look at you and wish their own men took care of them as well as I take care of you. We enter the restaurant. I am in a blue blazer and khaki pants, expensive fabric, silk cotton blend shirt, open neck, a hint of chest hair. You are in the stunning outfit we have just picked out for you. The maitre d' addresses me by name and takes us to our table. Heads of both sexes turn and watch us...

When you lean in to kiss me on the lips, you are a bit startled that my hands seemlessly take up a postion behind your head and hold your lips against mine. You note the sense of comfort, ease and entitlement with which I hold your head firmly in place as I trace yiur lips with my tongue. You also note the skill with which I so ao, sending tingles throughout your body. The food arrives, the wine flows. The hormones course through or veins. I leave the waitstaff a generous tip, the valet brings us the Mustang and we are off to the show...

 

[debbiev]

Our Date Continues, So Far So Good

With you taking control and kissing me deeply I know this is going perfectly. I'm proud to be with such a distinguished man, so well dressed and looking hot. Despite you being a lot older than me I actually feel comfortable with you.

I can say that I am not used to so many people staring at us. I kinda feel like a celebrity. We are treated like royalty as throughout the dinner waiters scurry around to make sure everything is perfect. Wow have I moved up quickly. I mean from playing poker and hustling at pool, ending up tens of thousands in debt, if not more, I lost count, to becoming Ms Dignified along side a very wealthy man. You are obviously well know here and I'm sure at all the elite places. Oh I can definitely get into this for the rest of my life. God you should only know the real me.

After dinner we head to the play in your Mustang, everything is just so perfect.
"Thank you for that amazing dinner Dave, I'm so looking forward to seeing Hamilton with you." Thinking, I can actually talk about American History intelligently. It was one of the few subject in high school I was interested in. So at least I won't appear ignorant. One of my fears is you will see me as shallow compared to your refined tastes. But maybe you are so crazy about me you won't notice. I can only hope.

We get out of your Mustang and the Valet takes your car and we walk in. Again people staring at us. God I love this.