Debbie's Gambling Debt (Closed)

[cliteatingman]

Hamilton At Last

You like the fact that my causual glances at other men's dates are clearly dismissive. I am not looking to trade up. I am clearly confident that you plus clothes I bestowed upon you make you the hottest date in the theater and I don't need to look twice at anyone else's date to reassure myself this is the case. The usher who leads us to our two seat theater box is quite the looker herself. Even as I tip her generously, you can tell I am quite dismissive of her charms. We exchange a few pleasant words about how great it is to be at the show. Then the lights go down and the curtain goes up.

Shortly thereafter, a hand wedges itself under your butt, then under your dress, and finally under your thong. You turn to me, but my eyes are riveted on the show. You doublecheck that the hand is attached to me. It is. The fingers are now separatinf your labia and exploring your entrance. They move with confidence, competence and a sense of entitlement. When I paid for the dress and the thong, I staked a claim to the body that wears them. It is not likely that questioning my absolute entitlement would be appreciated. As you begin to get wet, you realize that the dress has been moved out of the way of your wetness. The fingers evidence much knowledge and experience with the female anatomy. You're pleasure and arousal increase. Just as your breathing gets to the point at which others might notice, the fingers stop. When your breath becomes even again the fingers explore your folds. It occurs to you that I will spend the entire show edging you...

 

[debbiev]

Excitement and On Edge, But Not From the Play

Being with you just makes me feel so secure, like you know exactly what to do at all times. I mean just the way you carry yourself, it just makes me feel proud to be with you. I just hope I can live up to your standards cause I wanna live with you and have this elitist lifestyle. I just don't want you to find out my ghetto gambling past, I doubt you would ever want to be with someone who in your eyes is a lowlife. I'm gonna do everything possible to make sure you never find out.

The two seat theater box is amazing, I've never even been to a play. Well I was at a high school play once. This is pretty far removed from that.

I thank you again for taking me here and I tell you I'm excited to see this play because I love American History. You respond back and make me feel like what I say means something. That makes me like you even more.

The play begins and within the first few minutes I feel a hand under my dress and then tracing up to my thong. I'm totally surprised at you doing this. There goes my wannabe be classy self. I thought that would at least wait until we got home.
But hey it's kinda fun, totally unexpected, which makes it more exciting.

Feeling your hand over my thong as you rub it back and forth. I instantly get wet, knowing you can feel my wetness through my thong. Then feeling your fingers slip inside my thong as it probes my lips and then traces them, then moves up and down my cunt. You gently trace up to my clit and back down, knowing you feel my juices flowing as I begin to softly moan. You pull your hand back and I look at you in surprise, god I wanted to fucking cum. But loving you doing this to me in like the classiest place ever. The extremely itself are a turn on.

I begin to calm down and try to watch the play, but your fingers begin again. You are relentless as you're getting me to the edge. Thinking I may cum, my breathing intensifies as I squirm in my seat. Softly moaning again and feel like I'm seconds from releasing my cum and you stop. I groan in disappointment. But loving it. I look at you and hold your arm. Then lean towards you and whisper in your ear, "Dave, you are such a meanie, but I love it. You are driving me crazy"

 

[cliteatingman]

"I am, glad" I whisper, "That is my intention." I kiss you and push my fingers deeper inside of you while my thumb plays with your clit. As your breathing gets heavier. I back off again. This pattern continues throughout the play and I bring you close to the edge a dramatic high points, such as the Jefferson-Burr election, before letting you back down. When the play ends, you are soaking. Just before the lights come on, I withdraw my hand from you and lick my fingers clean as if it were the most normal thing in the world. When the lights come on, we join the rest of the audience in giving the cast a standing ovation. As we start to leave, the usher notices a small wet spot on the seat and gives you a conspiritorial wink.

We step outside and wait for the valet to bring us the car. He holds the door for you, not being able to keep his eyes from wandering your body. My dick grows a bit as I think that no matter how much I tip him, he will never be able to buy a girl a dress like yours. It grows a bit more when I tip him twice what I had originally planned.

I get in the car and wordlessly turn on the ignition, disengage the e-break, and push a button raising the adjustable steering wheel. Equally wordlessly, I unzip my fly, pull my cock out and pull your head into my lap. As your mouth opens to receive my cock, I readjust the steering wheel to bring it down on top of your head. You realize that the underside of the steering wheel is contoured precisely to the shape of the human head and that it has been upholstered with something soft and comfortable that feels great against your head. In case you had any doubts that this was a design feature, I push a button and you receive a gentle scalp massage. I step on the gas and thrust my pelvis. We're on our way home...

 

[cliteatingman]

Bump...

 

[debbiev]

The Most Unique Blow Job Ever, WTF?

Looking at you as you continue to finger me and drive me to the edge, only to stop when I'm about to cum. I sigh in frustration as I feel my thong is absolutely soaked. You continue again, this time I tell you, "Oh god Dave, you have to stop or let me cum, please" But you remain silent and just continue to finger me until I'm at the edge and then you stop again. I quietly let out a frustrated "Oh fuck no". But it doesn't matter, you start up and I squirm but your fingers are relentless. Over and over, you driving me crazy, but deep down loving the attention, despite this being totally classless in a very classy place. Hoping you don't think I'm trashy, but if you like doing this I'm fine with it for sure.

The play ends and you pull your fingers away and lick them. I smile, feeling embarrassed as the lights go on. I stand up, wanting to reach down and straighten my soaked thong, but unable to do that without anyone seeing. Instead I just clap like nothing happened. Don't ask me about the play, I have no idea what it was about.

The usher walks over and I see him look at my wet seat as he winks at me. I'm embarrassed and quickly leave so I don't have to face him.

I get in your car as the Valet stares at me up and down. Just hoping I don't have a wet spot on the back of my dress, feeling self conscious that is what he was staring at.

Back in the car, I see you raise your adjustable the automatic steering wheel and then you unzip your pants. You pull your cock out, I'm pretty surprised to see you doing this but I don't say anything. You then pull my head over it. We didn't even leave the valet parking area yet. But I'm not about to fight you, I mean first I'm horny as fuck and second I want this life of luxury, so yes I have to be willing to do things sexually if they are what you want. Within reason of course. I open my mouth and I slowly ride your cock down.

I feel the steering wheel adjust onto the back of my head, locking my head in place over your cock. The steering wheel is cushioned so it doesn't hurt and it's obviously designed to lock my head, or other women's heads unto your cock. It gently begins massaging the back of my head, it actually feels good.

I feel the car moving as you thrust your hips so you fuck my mouth. It's clever, but this isn't how I wanted our first time to go. I mean I'm locked here and forced to have your cock moving in my mouth. Feeling like I'm less than worthy, kind of like you totally disrespecting me. I mean if you asked me to try it I would have, but you kinda forced me.

But still, this will all be worth it when I become wealthy living with you. So it's okay, I can do this. It's my ticket out of my shitty life. Feeling your hard cock going back and forth in my mouth, then tasting your precum, knowing you may cum in my mouth. Your cock begins to throb in my mouth as the car and your hips move. Unable to do anything but be forced to ride your cock as it bobs up and down in my mouth. The ride seems long as your cock bounces in my mouth, I begin drooling over it and I know some of my saliva is coating your cock as well as seeping out of my mouth and onto the base of your cock and balls. Hoping you don't think I'm slobbering all over and it turning you off. Trying to maintain some dignity, as much as one can maintain dignity with a cock stuck in their mouth. But I don't complain or grunt or scream into your cock. I try to do my best despite this lasting a long time. Knowing that at any moment you are probably going to be cumming in my mouth.

 

[cliteatingman]

As we drive, you recognize the rhythm of my thrusts into your mouth as very similar to what I did in the theater. I am using your mouth to edge myself.

Even from beneath the steering wheel, you can tell my body is bifurcated. The lower half is absolutely focused on fucking your mouth, bringing myself to the brink and then backing off. The upper half ia absolutely focused on driving, two hands on the wheel, eyes on the road, near normal breath with very occasional response to the vigorous thrusting of my hips. As we approach my driveway, I bring myself to the edge again. As I put my foot on the break to bring the car to a final stop, I give my hardest thrust yet, force my cock deep into your throat and gift you with a spurt of warm sticky cum.

As I take the key out of the ignition, the steering wheel rises automatically. I kiss you with all the passion of a man who has just received a fantastic blowjob. My tongue explores your lips and the inside of your mouth for any traces of cum. Finding none, I break the kiss, look you in the eye ans say "Good girl!" Then I say "Every time we get into my car you will assume this position without my having to ask or offer physical encouragement! Understood?"

We go into the house. I say "Hang your nice new dress in the closet and remove your soaking wet thong. Meet me in my bedroom in just the bra I bought you. I will pour two glasses sparkling wine from France's Champagne region, the only real Champagne...

 

[debbiev]

Future Blow Job Instructions In Your Car

Your hips move and then slow down or stop. Knowing you are edging yourself using my mouth as I'm locked under your steering wheel. I taste your precum and gulp it down as you continue your slow thrusts into my mouth. Still feeling this is so wrong, I mean you should have told me and I would have agreed to this. But to trap me like this and lock me here is just weird. But I have no choice and I just have to get through this until you cum in my mouth.

I feel the car turn and stop and you thrust hard into my mouth. Your thick cum shoots into my throat, not thrilled with anyone cumming in my throat I gag on your cock but recover and begin to gulp your cum down as more shoots into my mouth. I cough and gulp again, then swallow as I manage to get all your cum down. Hoping that my gagging and coughing didn't ruin it for you, but I tried and I did get it down. Later, I will have to tell you to not cum in my throat next time, hopefully you listen.

The steering wheel rises and I sit up and look at you, kinda in shock but I manage a smile, the last thing I wanna show you is that I'm pissed off. I mean you are my ticket to wealth.

You kiss me and our tongues meet, but I know you are checking my mouth to make sure I swallowed all your cum. When you call me a 'good girl' and then instruct me that I assume that position every time we drive anywhere. I'm surprised that you are treating me that way, but I know what I need to do so I compose myself and say, "Yes of course Dave, you will never have to remind me, I'm here for you. I mean I really like you and I will gladly do what you ask. I think you are such an amazing man."

As I say that I'm thinking, what the fuck was that? You're such a weirdo. Although I guess it's called eccentric being you're so rich. I suppose you think I'm your stupid whore. How fucking disrespectful. But it's still my chance for wealth and I suppose sexually performing for you is worth it. Although it makes me feel like shit.

As we walk into the house I feel a bit frustrated, you edged me over and over and I had to give you a forced blow job, but you never let me cum. But when you give me orders to hang up my dress and remove my soaked thong and meet you in your bedroom with just my bra on I smile, thinking, okay, maybe I can cum now, I seriously want to after being worked up the entire night.

I go to my room and remove my dress and my soaked thong. I take off my pumps and just walk to your room wearing my black bra. I feel totally awkward and also realize I should have taken better care of my pubes. Well it's been awhile since I had sex so I kind of let them go a bit. I hope you don't mind.

I walk into your room, feeling self conscious and a bit silly just wearing a bra. Hoping you don't do anything weird like the steering wheel contraption. But I suppose I'll soon see.

 

[cliteatingman]

When you get into the bedroom, I am wearing a burgundy-colored silk bathrobe, open enough to show off my chest hair. I hand you a glass of bubbly and offer a toast "To your new life!" We sip. It is certainly the best Champagne you have ever tasted. After sipping, you realize that yours is slightly cloudy, while mine is crystal clear. I remove my bathrobe revealing a bidy that is in good shape for my age and a semi-erect and growing cock. I kiss you passionately again, and this time my tongue explores your mouth with no apparent motive other than intense lust. I unhook yiur bra and throw it on a chair. I begin to play with yiur breasts without separating my mouth from yours...

 

[debbiev]

Debbie's Hesitation Wait and See Attitude

Yes to my new life. I smile as we toast, but am totally unsure as to what I have gotten myself into. I mean you are quite eccentric and I kinda feel like I'm your live in whore. But in exchange for wealth, maybe it's worth it. Although I am having second thoughts.

I look down as you remove your bathrobe and I see your semi hard cock. You step towards me and we kiss deeply and our tongues meet. I would think you want to fuck, but with you I'm not sure, I mean lets face it, that was the oddest blow job ever and you totally caught me off guard. So I'm not sure what to expect.

I feel you unclasp my bra as you take it and put it on the chair. Your hands on my breasts as we continue to kiss. I wrap my hands around your waist. You feel strong and it's obvious you work out. We continue kissing as I don't wanna take the lead here, it seems you like doing that and I don't want you to think I'm taking over. So I lay back a bit and just hold you as we kiss.

 

[cliteatingman]

I take one hand off a breast and skillfully trace your labia without breaking the kiss. Then I slide two fingers into you and feel how moist you are. I break the kiss and lick my fingers in a smooth motion. "You are so ready for me! Welcome to the exclusive club of women I care to fuck!" I throw you on the bed. Before you know it, my lips are again pressed against yours and my cock pounds your cervix with every stroke. I look you straight in the eyesnas we fuck, with the most intense lust you habe ever experienced...

 

[debbiev]

Orgasms and Then a Barrage of Questions.

As we kiss I feel your hand tracing my cunt lips and then your fingers entering me. You pull back and lick your fingers of my juices as you tell me how ready I am for you and that I have joined an exclusive club of women you care to fuck.

Yes I'm wet but I don't wanna hear about being in your exclusive club or about other women you fucked. I want you to want me and only me, I don't wanna be part of a club, another number or as they say, another notch in your belt. It makes me realize that maybe I'm not the one for you, that you just pick women up, fuck them and toss them when you get tired of them. I thought this was more permanent, that I would be living in luxury for many years to come, but maybe it's not that, maybe it's fuck me for a while and then kick me the fuck out when you want new blood.

As we fuck you stare straight into my eyes. Feeling your cock thrusting deep inside my cunt as I stare back at you. You are intense and I like that. You continue to fuck me hard and I begin cumming, the whole time looking in your eyes. Feeling you cumming too as you continue to stare into my eyes.

When we begin to come down from our orgasms I decide I have to say something. You lay next to me and I turn to you, "Dave, that was seriously good, but I think we need to talk. You mentioned an exclusive line of women and how I have joined them, well that didn't make me feel special. I only want you to have one woman, me. So I need to know where I stand here, like I have lots of questions. I know you have been generous with letting me live here, but how long do you want me here? Do I need to move on soon? I need to know what our relationship is. I want direction. This is all very different from what I am used to, so I feel confused."

I take a deep breath, and add, "I really like you Dave, I wanna be with you. But I want to be yours, I want you to respect me too and I don't think you do. I think sexually you wanna treat me like your slave. I understand I have to give back to you, but I just need to know how you feel about me as a person"

Knowing this suddenly got real and intense, hoping you tell me what I wanna hear and not just say I'm here for the sex and to be your trophy to go out with, although I'm thinking that is more the truth.

 

[cliteatingman]

I get up out of bed. I pull two documents out of the drawer and hand them to you. "These are copies. The originals are safely far away from you so it would do you no good to rip them up. The first one is your gamling IOU. I bought it for 3 cents on the dollar because no one believed you were good for it. But you owe me the whole $100 K. I had no idea you were the same chick whose gambling debt I owned until I saw the identical signature on your credit card with the illegible last name. When I pointed out to the credit card company that you had a $100 K gambling debt, they despaired of collecting your $200 K credit card debt. They sold it to me for 10 cents on the dollar. Your car is non-functional and I had to pay my mechanic to dispose of it. You owe me $500 for that. You have the following choice: stay here and perform any sex act any time I want. You will cum often, eat and drink well and have fun dates out like tonight. Or you can leave on foot and I will have your wages garnished any job you get. Don't talk to me about love or exclusivity. I don't do either." (BtW, you only have about an hour until the drug knocks you out...)

 

[debbiev]

Trying To Negotiate a Sex Slave Business Deal

I read over the documents and I feel myself tensing up, now knowing that you know who I am, that you knew before we even went on our date. Yet you didn't say anything until I called you out. Fuck I can't believe this happened, what are the chances of crossing paths with the man who bought my debt? Shit! But I suppose that doesn't matter now, what matters is what the fuck do I do now?

I look at you and I try to establish ground rules. Thinking that if the ground rules aren't to my liking I'll cut and run. Wouldn't matter on garnishing my wages as I haven't had a job on the books for years. The last few years I gambled mostly at poker and hustled at pool. So that isn't something I paid taxes on. Besides I ended up losing $100,000 in gambling and charging up a bunch of credit cards to $200,000 in order to live.

My decision is whether I wanna stay here and be your sex slave in exchange for living a wealthy lifestyle. I mean that was my original goal here. I never fell for you, I thought you were totally eccentric and maybe too classy for me.

I don't have a car, so how do I get out of here anyway? I obviously don't have any money either. But do I even wanna leave? Maybe I should stay, I suppose I need to find out the rules first. But first I need to try to bullshit my way out of this or at least try to make it easier on me.

"Dave, first off I was falling in love with you. You are such an amazing man. I wanted you to just be with me and for us to live together for a long time. I thought you wanted that too." I look into your eyes and hope you buy my total lie.

I continue on, "I know my past sucks and I know I owe a lot of money, but I don't think $300,000 is a lot to you and so I'm hoping I can stay here and you will forget the debt. Or maybe stay here for a few months and then the debt is cleared. But I think I would like staying here much longer if you didn't mind. But if this is just about me clearing me debt then I need you to decide on a timeline, like a certain amount of debt is paid off every month. Then at that time I'm cleared of my debt and can leave."

Of course if your rules don't conform to what I want I plan on getting the fuck out of here in the morning. Even if I have to walk miles to a house or farm to do it. I could also be homeless for a few days as it's summer. So I have other options, in case you dig your heels in.

 

[cliteatingman]

"I know I am amazing and maybe you are falling in love with me. Unfortunately, I have learned the hard way (pun intended) that neither amazingness nor love is as effective as leverage at getting my cock the kind of access it wants and needs. Put a ring on a woman's finger and all of a sudden your cock can't go anywhere other than her pussy and the frequency of that declines rapidly... On the other hand, a woman will a man put his cock anywhere he wants if the cost of not letting him do so is too high. On the other hand, I am interested in hearing the terms you are offering for clearing your debt." (You begin to feel drowsy)

 

[debbiev]

The Offer and Escape Plan

You confirm to me that you are totally full of yourself as you actually believe that I'm in love with you. I suppose being super wealthy does that to a man. You might be smart but I have the street smarts that can outsmart your smart. At least I think so.

But all that doesn't matter, what does matter is I have to get the fuck out of here and in the morning I intend to do just that. I'll have an entire day to find someone and get help. If I have to walk through corn fields so you don't find me I'll do that. Or at worse I'll find a place to sleep outside. But I'm not staying here and agree to be your sex slave with you using all my mouth, cunt or ass any time you want. No way.

So I make a fake offer, this way you won't suspect me getting up at 5 AM and sneaking out of the house and getting a good start on you. "Yeah, I'll offer to stay here one full year and after that time my debts are....well...are...yeah....my debts are clear.....totally....um....clear. I don't feel so well." I lay on the bed, turn on my side and doze off.

 

[cliteatingman]

The next Day

You wake up alone in my bed. You look at the clock it is 11 AM and you feel like you were hit by a truck. You roll slowly out of bed and you go into the master bedroom bathroom. It is even more elegsnt than the guest bedroom bathroom, with a bigger hot tub. You go to take a shower. Then you notice. There is a ring in each of your nipples. You try to remove one. You begin to feel a gentle electric shock. Against your will, you feel a bit turned on. The more you try to remove it, the stronger the shock gets until you are forced to stop trying because it is painful. (Little do you know I am watching all this on my cell phone.) As you begin to wash yourself, you realize there is one more ring. Your clit hood is pierced too. Just at that moment (I push a button on my cell phone and) your clit starts to tingle with pleasure. You start getting wetter and wetter and more aroused. (I push another button and) your nipples are being gently stimulated as well. Your brain wants to plan your escape but your entire body says "NEED TO CUM!" At that moment, you hear me walk into the bedroom. Your brain says "MUST ESCAPE." Your body says "NEED TO CUM" You realize that your new jewelry might make escape an electrifying experience...

 

[Actiescape]

Not a big fan of gambling and any other illegal ways of making money, and consider them immoral and without respect. If you don't trust me, and want gambling to exist, just check this , and look with your own eyes how bad it is Hope there are people that also have negative opinions about gambling, if not hope my message showed you the contrary. I wish everybody a good day, and thank you for letting me share.

 

[debbiev]

Not a big fan of gambling and any other illegal ways of making money, and consider them immoral and without respect. If you don't trust me, and want gambling to exist, just check this , and look with your own eyes how bad it is Hope there are people that also have negative opinions about gambling, if not hope my message showed you the contrary. I wish everybody a good day, and thank you for letting me share.

WTF are you talking about? This is a roleplay story from like 6 months ago. It has nothing to do about promoting gambling. Why don't you take your do-gooder ass and boot it out of my thread. Go find somewhere else to preach...moron.