The Contest

"Let's go over the rules so they're crystal clear. OK for me to record this conversation?"

"Yeah, sure" I said. The man standing in front of me was efficient and proper, almost lawyerly. He seemed like a guy who was very used to rules and ensuring that people followed them precisely. He held a clipboard with a few pages clamped to it, and he appeared to be reading from a checklist.

"Very good. I am Mr. Ross. You are Mr. Franklin, correct?." I nodded. "You attest that you are here on your own volition, that you have not been coerced or compelled in any way to participate in this contest. Please answer verbally for the record."

"Yes, correct Mr. Ross." Of course I'm here voluntarily. This is going to be the easiest dough ever made.

"Good. Next, you agree that this is a winner take all contest?"

"Yes."

"And you agree to post $275,000 in trust to my firm. This money, and the $275,000 from your competitor, less fees, will be held in escrow until the game is over. The winner of the game will receive $500,000, with the remaining $50,000 going to my firm, as the fee for running this contest. Agree?"

"Yes, agreed."

"Excellent. Please sign here."

I read the document. It appeared to be in order. I signed it.

"All right. You've read the Rules, but I am contractually required to read them to you, then to get your written and verbal consent. If you agree to these Rules, you will immediately transfer the funds. I also inform you that your competitor has already agreed to her Rules, which due to her sex are somewhat modified from yours. She has already posted the funds into our account. Upon my receiving confirmation of your funds transfer, the game will begin immediately. OK?"

So official and legal. "Yes, agreed."

After months of planning and anticipation, it was finally happening. This is really exciting. The ad had been on Marketshop: Win a fortune the fun way. I clicked on it and up came a picture of a young man with a shit-eating grin on his face. In the background was a picture of a woman in lingerie, not a bad lookin' broad I guess, standing with her hands on her hips and a big scowl on her face. So I called 'em up. They wanted to know a lot about me. Where I lived. What was my net worth? How much money did I have access to? Stuff like that. I wasn't comfortable answering all those questions right away. No sir. So they asked me to come in.

I did it. Right off the bat they did a credit check. They found every penny I owned. I'm doing OK, I guess. If I sold my condo, my car, all my investments, I could probably come up with $500,000. I was able to borrow about half that using those assets for this.

When they explained the Rules to me, it sounded easy. Too easy. So I took the Rules to a lawyer friend of mine. He looked them over and told me that it looked pretty tight to him. All you have to do is hold out, he said, and you win.

I had to win of course. If I lost this kind of money, I'd be in big trouble. It would really set me back. But how could I possibly lose?

Mr. Ross began to read from his checklist:

"Contest Rules

1. The contest takes place in a hotel suite consisting of a living room, a bedroom with a king size bed, a small kitchen with fully-stocked pantry, and a luxury bathroom. The bathroom door has been removed to eliminate physical barriers between the participants. The room is equipped with microphones and cameras. It is monitored during the entire contest;

2. The hotel suite is # 1504. The windows are shatter proof and do not open;

3. The door to the suite has been specially fitted with a magnetic locking device controlled by the supervising representative of the contest. No-one will be allowed in or out of the suite until the termination of the contest;

4. Unless the contest is won sooner, this contest will run for exactly 48 hours. Upon the expiry of said 48-hour period, the man undersigned will be declared the winner;

5. The contest is terminated earlier than 48 hours under the following conditions.

a. The woman has won the contest;

b. Either party requests exit from the room for any reason whatsoever prior to the expiry of the 48 hours, thereby conceding victory to the other party. The request to exit is made by pressing the red mushroom button beside the door. This will instantly release the mag lock and open the door;

6. Inside the suite is a woman, who was borne a woman. She has willingly agreed to similar terms as per this document, has signed her full consent, and has posted her competition funds into our escrow account;

7. You may conduct no violence, physical harm, or non-voluntary physical restraint of the other party of any kind. My firm will be the sole arbitrator to evaluate whether such actions were enacted;

8. The female wins upon the male having sexual intercourse with the woman to "Completion". Completion is defined as the man ejaculating into the woman's vagina, mouth, or anus. Simple penetration without ejaculation does not end the contest;

9. Should the man enter the woman, she may hold him there if she is able. She may do this with her arms, legs, hands, feet, or any other body part, but she may not use any other physical restraints, including but not limited to ropes, clothes, or sheets, unless the man verbally consents;

10. Should the man withdraw and ejaculate outside the woman, the contest is not concluded;

11. The man agrees to take 100 mg of Viagra every 4 hours during the contest;

12. The man may not masturbate or rub his penis on the woman (or on anything else) to ejaculation;

13. The man will be allowed to wear only the bathrobe issued to him, without belt. The woman has no clothing restrictions and has stocked the suite with many clothing selections;

14. You hereby declare that you are not gay and that you have normal sexual interest in women;

15. Any violations in these Rules will result in your immediate disqualification and loss of all funds deposited.

"Mr. Franklin, do you understand each of the rules as I have explained them to you?"

Lots of rules. But it still sounded easy. I was sure that the woman was probably going to be reasonably attractive. Probably beautiful. Nobody would have trouble resisting someone repulsive. But hey, all I have to do is not fuck someone for two days. How hard could it be?

"I agree," I said.

"As previously agreed, did you swallow at least 100 mg. of Viagra approximately one hour ago?"

I wasn't hard, but boy, it sure wouldn't take much. "Yes, confirmed" I said.

"Very well. Your assent is recorded and on tape. Please sign here." Mr. Ross presented me with the form with the Rules. I signed it. "Excellent. Now here is the site for the funds transfer. Please transfer the funds into our Escrow account."

I navigated to my own escrow account which I had set up for this purpose, entered the account information of the transferee, and clicked SEND. There. It was done.

"Very good" said Mr. Ross. I can confirm that I now have $525,000 in the escrow account. I will now transfer your $25,000 share to my firm's account." And with a few clicks, he did that. I observed and noted it to be true.

So that's it. God knows I have to win. Losing would be horrible. But that's good, right? More motivation not to be stupid. Who's gonna fuck someone with that kind of money at stake?

"All right, shall we begin?" asked Mr. Ross.

"No time like the present," I responded.

"Excellent." And with a flourish, Mr. Ross opened the door and I stepped into the suite. The door closed behind me, and the mag locks clicked into place. Let the game begin.

I looked around and immediately realized that I was fucked. Big time.

Standing by the bed, one hand on her hip, looking squarely at me, was the sexiest, most beautiful woman I have ever seen in my entire life. I am not exaggerating. She oozed sex from every square millimeter of her face and body.

Her platinum blond hair cascaded in thick curls to her tiny waist. She wore a form-hugging tank top, no bra, deeply cut to the biggest, roundest, most beautiful set of breasts I have ever seen. She had the face of an angel, big round green eyes, thick, pouting bee stung lips. She wore teeny cutoff shorts. Her long, athletic, tanned legs were clad in hold up fishnet stockings. She wore studded, shiny-black Loubouton spikes that added five inches to her six-foot frame. She was the embodiment of pure sex. She was the kind of woman that men jack off thinking about. The kind of woman who can get any man to do anything for her. That men fight over. Wage wars over. Standing before me was an apex sexual predator of the first order.

How the hell was I going to resist this creature? This woman was made for fucking. And her sole mission over the next 48 hours was going to be to fuck me. Half a million bucks, I said to myself, half a million bucks, over and over and over.

"Hi" she said. "I'm Claire. What's your name?"

"I'm Jake." My mouth was so dry, the words hardly came out. My heart was pounding. My cock pushed out though the bathrobe, straight out parallel with the floor. Embarrassed, I pulled it back it, but there really wasn't any place to put it.

"That's OK Jake, you don't have to worry about that. I've seen one before."

"I bet she has," I thought.

She walked up to me, looked deeply into my eyes, and put her hand on my upper arm. "Hi Jake" she whispered. In heels, she was several inches taller than me. Her huge round breasts heaved with each breath. They were at the level of my neck. It took everything I had not to look down into her spectacular cleavage.

Claire put her arms around my neck, pulled those glorious tits under my chin, and began to gnaw on my ear. Just like that. I started to pull away, but she was strong. "No? This is OK, right? You're a very hot looking man. We can make out for a bit, can't we? Just get acquainted a little? A little kissing never hurt anyone did it? You won't lose the contest by making out a little."

As I was about to speak, she moved in and pressed her mouth onto mine. Her lips were soft and moist. Her tongue explored my lips a little, swishing around a bit before she gently pushed it into my mouth. My dick was so hard by now it was throbbing. Claire had long, long legs and my dick pointed straight out, just below her pussy.

As she was kissing me, she smiled, made a little "mmmm" sound, crossed one high heeled foot over the other, gripping my cock between her fishnet thighs. The feeling of this stunner, her tongue in my mouth, enormous tits pushed into my neck and chest, legs clamped on my dick. It was almost too much to bear. Already.

I had an idea. If I played it right and avoided the camera angles, maybe I could get away with it. I started to move my hips. Round and round, backward and forward. If she kept up the grip, maybe I could cum on her thighs and make it look like she did it.

Fat chance.

"Oh Jake, silly boy" Claire pulled her head back and looked at me. "Do you really think I'd let you do that?" She smiled and gave me a little kiss on the lips as she uncrossed her legs and released my manhood. "Very clever though."

Yeah, real clever.

"Come on over to the bed. I won't do anything bad, I promise" she said. "Let's talk about this."

"Do you think I'm dumb? Of course that's where you want me. I'll tap out in 2 minutes if I follow you there. You just want me to fuck you right now, don't you?"

Claire released me, pouting. She walked over to the fireplace and turned to face me. Slowly she released the clasp on her little cutoffs and let them fall to the floor. She then pulled the tank top up, over her head and tossed it on top of her little shorts. All she had left was her panties, her shoes, and her fishnets.

"Jake, you seem like a really nice guy. Believe it or not, I don't get a chance to have sex very often. No really. I know what guys want, but I'm not interested in easy sex. I want someone who's stable and dependable. I'm not just someone anyone can screw with.

"Look, I know what I look like. This's what the good lord gave me, after all. But it's a curse, don't you see that? It's so hard to find a man who can't see past all this", she said as she smoothed her hands down the sides of her glorious bare breasts and drew her fingers over her nipples.

"But that's all you want to do, right? Have fast sex with me to win the money?"

"Well, I'd love to have the money, sure. It's so important to me. My poor mother. She needs everything I can scrape up. I'm really, really worried about her."

"Really? Are you for real?" Kind of a weak story. Of course she'd say that.

"Yes! Of course! Do you think I could be that deceptive? Do you think I'd talk about my mother that way? Really?" She began to cry.

Crap. This wasn't going so well. She's crying. Oh god, she is something though. What I'd give for a woman like that. Would I give $250,000?

Forget it. Sure I could fuck her. Right now. But she'd never stick with me. It's just a story. She'd move on to the next one. I'm just a money ticket.

But Jesus, what if she really was a nice girl? Could there be something there? Was it worth a shot? I mean, she was worth it.

Or is that my dick talking?

"Look" I said. "I didn't mean to hurt your feelings. I'm sorry. Really I am. How can I make it up to you?"

"Well, you can be nicer to me. I'm not a bad person."

I said nothing.

"Look" she said. "I'll put some clothes on. Would that help?"

"Probably" I said. "You're kinda distracting me right now. I can't really have a good conversation with you when you look like that. I'd like to get to know you a little".

She brightened a little. "Ok, I'll go put on a dress. For now." She winked.

Claire went into the bathroom, humming a little tune. Meanwhile, I had to get my strategy down. Everything I had thought I was going to do was blown. I thought I'd just come into the suite, ignore the woman, let her do whatever it is that she does, but ultimately not with me.

But Claire. Oh my god, Claire.

In a few moments, out she came. Fuck. Definitely no better. Skimpy-short, pink baby doll dress, cut just below her pussy, super low cut, her huge breasts swelling out. Garters, seamed stockings, and high heels. She was all done up, hair brushed, makeup, nails, perfect. Perfect for fucking, that is.

"Is this OK, honey?" Claire asked.

"Yeah, sure" I said. My dick just popped out again.

"Jake, you are a frisky boy. That looks really tasty."

Claire quickly closed the gap between us and grabbed my dick in her left hand. Electric! I couldn't touch my dick at all, for fear of losing the game. But she could. She brought her other hand over to my cock and began to hold it like a golf club. This squeezed her massive breasts up and into my neck and chest. She looked down into my eyes as she squeezed and massaged my cock ever so masterfully, working me up, getting me ready. Oh, I was ready. Just a little more, Claire. Just a little more and I'll get off.

Precum was coming out of my cock, beginning to lubricate it a little. She got a little on her hand. She slowly licked it off, one finger at a time, as if savoring every drop. When she was done, her tongue curled back into her mouth like a roller blind. Her eyes never left mine. I nearly came right there.

"Mmmm, that's really nice. You taste wonderful. Like honey. Oh my god, that's wonderful."

Claire released my cock and licked her other hand, faster this time. "Oh, this is so sweet. I love the taste of you." She then lowered herself on her knees in front of me.

"Stop!" I said. "You can't do that."

"Just a little taste. I won't make you cum," she giggled. "I promise."

Oh man. Weakening already. "OK, just a little" I said. My plan was to pull back and cum on her face. Just like the Rules said I could.

She held my dick at its base pointed straight at her face. True to her word, she gently licked the head with her soft, wet tongue, swirling it around and around, getting all the precum off of it.

"Ooooo," she said. "I might just cum myself. The taste of you turns me on like nothing I've ever experienced."

She pulled the dress down around her waist and showed me those stupendous tits. Her face screwed up in ecstasy, eyes closed, her breathing quickening as she moaned.

By this time I was beyond horny. Jesus this woman is killing me. How can I resist this for two freaking days?

She knelt there, moaning, her mouth open. Damn it if I didn't take her head in my hands and gently insert my dick right between those full, juicy lips and into her hot, wet mouth.

Looking up at me with a mix of surprise and delight, she began to suck. She put a firm grip on the base of my shaft, holding my cock and deeply inhaling it. Her tongue massaged the soft underside, working it. The tip of her tongue was very firm and pointed. She used it expertly to swirl and massage my orgasm muscle. She knew exactly where to apply pressure. Then she pulled my dick out of her mouth, held it in one hand, and went onto it sideways, running her tongue along the soft underside of my shaft, bringing me closer and closer. She got her teeth into it, gently working her jaw back and forth. Then in one motion, she moved back and deep throated me, working my shaft with a swallowing action, over and over, like she was drinking down my cock. I was close. Almost there. Oh to explode in that mouth! Oh to cum into this stunning creature!

"No!" I cried, pulling away. "This is no good! I can't go down like this. What's it been, 20 minutes? No, I won't go down that easy."

I backed away several steps. She had been on her knees; now she leapt up at me, right off the floor. The sheer athleticism alone was amazing. She jumped onto me, clamping her legs around my waist, and crossing her ankles behind me. She wrapped her arms around my head and drew my face right between those magnificent breasts of hers, pulling me in with unexpected strength. I was locked in, fully in the grip of this stunning creature. She alternately pumped the pressure around my waist, squeezing and releasing, squeezing and releasing. Her chest was a heaving mass of flesh, up and down, embedding my face deeper into her cleavage. I tried to pull away, but I couldn't. She was too strong. And I couldn't hurt her. That was against the Rules. I was trapped. My cock was still throbbing from her suckling. It was still dripping with her saliva.

I could feel myself weakening. Quickly, she released my face and grabbed my head, pushing her mouth onto my face, covering it with a hundred kisses, my neck, my cheeks, my eyes, my ears. Working her way to my mouth, she drove her lips hard onto mine, her mouth hot and wet, roiling, working, her tongue slipping between my lips, invading, overwhelming my mouth, then withdrawing, then back in, out and in, out, in, out, in, fucking my mouth with her tongue, beginning to slobber on me. I could feel my stomach getting wet, getting soaked by her dripping, hot cunt, her legs squeezing around me, squeeze and release, squeeze and release. She pulled away and thrust her tongue into my ear, whispering to me.

"Fuck me, fuck me, fuck me, fuck me, fuck me," came her deep, throaty whisper as she gnawed and sucked on my earlobe. "Fuck me now, I'll be yours, fuck me, fuck me now, I need you inside me, please, fill me up, let me cum, I need it so bad. Fuck me Jake, fuck me." She pulled my face deeper between her tits. "I want you. I need you. I'll fuck you forever. Fuck me now, fuck me. NOW! I have to have your cock inside me. I'll fuck you so hard, I'll squeeze every drop out of you. I'll milk you dry. You've never been fucked like I'll fuck you. Let me fuck your brains out. Fuck you to oblivion. Let me! Come on!! Fuck me darling, fuck me, fuck me, fuck me. Your cum drove me crazy. It's never been like this. I have to have you. Pussy needs you. She's hungry for you, Jake. She wants to swallow you up whole, suck on you, pump you dry and keep coming and coming and coming for more."