A Really Stupid Bet

"This is a really good bet," I thought to myself. Over and over and over, I kept repeating to myself, "This is a really good bet. This is a really good bet. This is..."

Of course I was trying to convince myself I hadn't made a serious mistake in judgment. Here I was sitting next to a man I barely knew, dressed like a slut -- or more correctly, barely dressed at all. For the hundredth time I tugged at the hem of the scant skirt, sliding it ever so slightly down, hoping it would provide some modicum of covering. Useless I knew -- in seconds the hem rode back up where it was; nevertheless I felt compelled to keep trying.

I had to keep my legs tightly together; otherwise the crotch of my panties would be in plain sight. I felt the smooth material of my shirt rubbing against my nipples, unprotected by a bra and plainly visible beneath the thin covering. Hard, almost painfully hard. From the cold and friction of the shirt, I told myself -- although I knew this wasn't entirely true. The dampness between my legs certainly wasn't due to cold!

I was excited in spite of myself! Dang, I thought, what kind of slut am I, to be excited by this humiliation? Dressed like some kind of teenage hooker, sitting next to a man I barely knew, being driven to the park in the middle of the night.

At least it was a really good bet. Again and again I kept reminding myself it was a really good bet. A REALLY good bet.

It all started a couple of weeks ago...

.....

"You should try this, Staci," Maria told me. I stared at her over the rim of my martini then took a sip before replying. She'd been telling me all about something she'd heard from a "friend of a friend," some kind of betting club for rich guys. Where they made bets with girls, then paid off with lots of cash when they lost.

Of course the girls paid off in other ways when THEY lost.

"Yeah, right," I responded. "Like it's even for real! Who'd do such a thing anyway?"

"Rich horny guys," she replied. We both laughed; it was like a joke now. We were in a local singles bar, it was Friday night, we were there together, drinking and dancing and having fun.

Maria had been pestering me about the betting club for the last couple of weeks. She kept telling me she'd do it herself, but her hubby just wouldn't understand. She knew I was short of cash (temporarily, I hoped!) and could therefore really use the money.

I couldn't argue with that! The "prize" was $1000.00 or even more, in cash, all mine if I fulfilled the terms of the bet. There were several different bets; they were sexual in nature, or "adult oriented" as Maria put it. That part made me nervous. I had no desire to become some kind of hooker, regardless of how strapped for cash I was.

But the bills were piling up and unemployment was running out and that next job looked further and further away. Finally I knew I needed to do whatever was required in order to get my hands on some money. I thought about working at a topless bar, but if somebody I knew saw me there I'd just die! I called Maria, got more details about the bet club. She gave me a phone number.

The phone rang once, twice, three times. My heart felt like it would jump out of my chest, I was so nervous. What was I getting myself into? I kept thinking. What was in store for me?

To my surprise a woman answered. She sounded like a secretary, a crisp "Miller and Associates, how may I direct your call?"

I thought I must have dialed the wrong number; I hung up immediately. I double checked the number Maria had given me; nope, right one. I called Maria back; she assured me that was the number she'd been given. With shaking hands I hung up and again dialed the number.

This time the receptionist -- if that's what she was -- picked up on the first ring. "Miller and Associates, how may I direct your call?"

"I-I was calling about a bet..." I stammered.

"Of course, one moment please."

What the heck? I wondered as my heart continued to pound. After a minute or so I heard a man's voice. "Yes, I understand you're interested in our challenge."

So that's what they called it -- a challenge! I suppose if they called it a bet they'd get in trouble with the police.

The man -- he introduced himself as "Bill Smith" -- told me he couldn't go into the details of the challenge on the phone; he asked me to make an appointment. His voice was deep and soothing; I gradually began to relax. I made an appointment for the next afternoon.

I was surprised to find myself in a lawyer's office the next afternoon. Whoever was behind this had money, I thought to myself as I waited in the reception area. A nice receptionist offered me coffee which I accepted and cookies which I passed on. She brought me a clipboard with a questionnaire, which she asked me to fill out. "Don't worry," she reassured me. "All information is strictly confidential and is shared with no one."

The form had the usual personal information, name, address, age, sex, etc. I filled that all out; no problem. The last section was a little weird, kind of like a form I'd expect to see at a doctor's office. Stuff about diseases and when my last period was and had I ever had an abortion. I was a little nervous but I'd come this far so I filled it all out, then gave it back to the receptionist. She asked to see my driver's license; she made a copy on the small machine on her desk then handed it back.

After a few minutes an attractive secretary came out and escorted me to Bill Smith's office. The room was large, with a big walnut desk in front of a picture window, showing a nice view of the river. Bill was a grey haired man in his early sixties, with the trim body of a former athlete. I could imagine him running track or playing for his high school football team. Except for the grey hair and a few wrinkles I doubted he'd changed much since he was eighteen.

I heard a knock on the office door; the receptionist I'd met earlier came in carrying a file folder which she handed to Bill then left, closing the door behind her. Bill opened the folder and studied the document inside. Apparently satisfied he closed the folder and put it on his desk.

"Please excuse me," he said. "We have to make certain we're not dealing with the authorities or someone with a criminal record. We ran a quick background check."

"No prostitutes, eh?" I smiled at him.

"Exactly. Our clients are very," he paused for effect. "Discriminating."

As I listened to the handsome grey haired man explain the bet (or "challenge" as he insisted on calling it) I became more and more relaxed. His voice had a deep, hypnotic quality to it. I didn't see a wedding ring or picture of wife and kids; with that voice and personality I imagined he could talk just about any woman into the sack in five minutes or less.

With me it would have been less.

"We actually have several challenges," Bill explained. "Some pay more than others. All have some things in common.

"First and foremost, your safety and the safety of our clients will be assured at all times. No harm will come to you as a result of your acceptance of a challenge.

"This firm will represent you should there be legal problems or an arrest as a result of anything that transpires during the challenge. We don't anticipate such problems; nobody's ever been arrested, but just in case, I'll be there for you.

"At no time will you be physically harmed in any manner which would require hospitalization or the services of a doctor, nor will you be subjected to anything which would cause scarring, marking, broken bones, or any permanent disfiguration."

Permanent disfiguration? I fidgeted a bit in my chair when he said this. What was I getting myself into?

Seeing my discomfort, Bill smiled. "Don't worry, Staci," he said in a reassuring tone. "I just have to go through the legalities. We'll take real good care of you."

I smiled back at him. He went on to explain that there would be several challenges I could choose from, and several men I could choose who would participate. Not all men participated in all challenges. He talked on for a while; again I became hypnotized by the smooth tone and reassuring quality of his voice. After a bit the words lost meaning; there was only that soothing voice, telling me it was going to be all right, he was going to take care of me...

"Now, if you're still interested I'll show you a book which will describe the challenges and another with pictures and descriptions of our clients." I shook myself out of my stupor -- where was I? I wondered.

I nodded. He pushed a button on his phone, said, "Carrie, would you escort Ms. Livingston into the viewing room, please?" In a moment the secretary returned. I followed her down the hall to a smaller office with no windows. It had a desk, couch, and several comfortable chairs. On the desk was a large scrapbook.

"Please look through the book on the desk," she instructed me. "The first part describes the various challenges. The last section contains pictures of our clients. Select any challenge that appeals to you and as many men as you'd like. After you're done press the red button on the telephone; I'll return."

Just like a dating service! I thought. I sat behind the desk; she left, closing the door quietly behind her.

I began to read the descriptions of the challenges. All were sexual in nature, some more than others. All of them made me blush.

"Challenge one," I read, "Two females will compete against one another. Six males will participate. The winner will be the first female who successfully causes all six males to climax."

Well, that was embarrassing! I thought. I read on, "All parties will submit to venereal disease testing before the challenge. No party having any venereal disease will be allowed to participate. Challenge prize : $1000.00 guaranteed, $10,000.00 for the winner."

Interesting...Possible, I thought. A thousand bucks for having sex six times, and ten thousand dollars if I got them all off first. I knew I was attractive -- small, only five feet tall if I stretched just a bit, nice hair, ass and boobs. Pretty brown eyes, trim figure -- I only weighed a bit over a hundred pounds soaking wet. I worked out regularly; finding men at the singles bar was never a problem in spite of being a little over thirty. Nice hair and teeth.

Yep, I was a package all right. Too bad I was flat broke with nobody to take care of me.

I read on. "Challenge number two: Male will chase female. Female will dress as specified (see supplement). Female will be given a twenty minute head start over a two mile course. If caught female agrees to become the property of the male for the next weekend. Prize : $1000.00"

Property? Geez, what would THAT mean! But a twenty minute head start over a two mile course -- I did five miles almost every day on the treadmill; that only took twenty minutes. I could cover two miles in less than TEN minutes if I just walked.

Sounded like a sure bet. There was a pad and pencil on the desk; I wrote "Number 2" on it.

No sense reading on, I thought. I've got a sure bet; now to pick the man. I flipped to the picture section of the album.

Some of the pictures were Polaroid's; none were particularly good. There was an explanation on the first page; they had videos of most of the guys I could look at if I wanted.

The men looked pretty ordinary. All wore suits and ties; they looked distinguished, successful. I supposed they would have to be successful in order to be able to fork over ten thousand dollars, or a thousand dollars, or whatever a "challenge" cost them.

On the third page I saw a familiar face -- Bill Smith, the lawyer I'd just spoken with. Just like the Hair Club, I thought -- he was a client too!

I looked through the rest of the pictures. Most any of the men would do, I thought. Flipping back to Bill's picture I saw handwritten next to it the challenges he would do: "1, 2, 4, 5."

I closed the book, pressed the phone button. The secretary returned. "Do you want more information on the challenges, or to look at any of the videos?" she asked.

"Yes, and no," I said. "I want to learn more about number two. As for the man" I flipped the book open to Bill's picture, put my index finger right on his nose, "I choose this one."

...........

So here I was, in Bill's Mercedes. It was almost three AM; a full moon illuminated the streets. He was silent as we drove through the cool early morning. The city was asleep, quiet.

Bill had explained that I would be required to wear clothing he'd selected. He showed me a picture of another girl modeling the outfit -- short skirt, sheer white shirt, thong panties, no bra. White thigh high stockings, sandals with six inch heels. Bare midriff of course. I'd blushed, knowing I'd look like some kind of teenage slut.

But the lure of an easy $1000.00 was too strong. He told me he'd buy another outfit in my size; he'd bring it with him to my apartment.

"The chase will be in River park," he'd explained. "Dressed the way you'll be it'll be best if we do it after hours so to speak -- you won't want to be seen. We'll start around 3 Am this Friday if you're agreeable."

Unable to speak, I just nodded.

.....

Sure enough, that Saturday morning at 1 AM I heard my doorbell ring. Shaking a bit from nervousness I opened the door; Bill was standing there dressed in blue jeans and black short sleeved shirt. His heels clicked a bit as he stepped in; looking down I saw he wore black boots, which made him look even taller, more imposing.

He handed me a plastic sack and a hanger covered in a plastic sheet, like from the cleaners. "Change into your outfit, Staci," he told me. I nodded, nervous again.

I went into my bedroom, pulled the door shut behind me. Quickly undressing I removed a cream colored thong from the sack and pulled it on. It was snug but fit acceptably.

Next I searched for a bra; then I remembered his earlier explanation -- no bra. Shrugging, tore the covering off the hanger. Sure enough, the white shirt and black skirt were neatly hung on separate hangers. I removed the shirt, pulled it on, buttoned it.

The shirt felt soft against my skin. Expensive! I thought. A silky material, sheer but not transparent, white. Looking down I could clearly see my nipples, hardening with excitement, dark against my cream colored skin through the semi-sheer material. Not appropriate to wear out, the kind of outfit I might wear in my apartment to tease some man I knew I wanted.

I shivered. Next the skirt -- I pulled it on; it zipped in back. It was made of stretchy crepe material. It was just too damn short, barely covering my ass. No amount of tugging and pulling would make long enough without pulling it down off my stomach which was bare anyway; the shirt was short too. The skirt would ride right back up anyway, it was form fitting around my hips. Again, not appropriate. I shrugged -- wouldn't have it on that long, I thought.

Next I pulled on the stockings. Standard white thigh highs, no big surprise there. The sandals were another matter.

Standing up, I looked in the full length closet mirror. The sandal heels were too high, a full six inches. The effect was stunning, I had to admit -- my ass looked fabulous and I was short enough that they didn't look silly. But I could barely walk in them! Running would be out of the question.

Oh, well, I thought. Two miles, twenty minute head start, should be no problem even walking. And Bill was in his sixties after all; I was thirty years younger and in excellent shape physically. Still a good bet; I'd certainly win the thousand dollars.

I flipped the closet light off and hobbled into the living room. Bill looked me over a little too intently; I looked down blushing. "You look lovely, my dear!" he told me.

I smiled up at him shyly, then looked back down when my eyes met his. Damn, the guy was over sixty but as sexy as he was he could have just rolled me right onto my back and had his way with me right here on the living room floor. I felt my nipples tighten and felt a slow burning deep inside me as this thought crossed my mind.

Glancing up again I saw his steady gaze, knew he knew he could have me whenever he wanted, I was his for the taking. Looking back down I felt a hot wetness in my crotch. Dang, I thought, these panties will be soaked in no time!

Bill took my arm, gently guided me out the door. He opened the door to his car, helped me inside. This was all good as I could barely walk in the high heels; also my legs felt strangely weak and rubbery.

I felt myself trembling.

....

Finally we arrived at River park. The park ran down both sides of the river, fifteen miles on each side. The city had built benches, swings, and jungle jims on both sides. A couple of refreshment stands -- now closed -- provided sodas and snacks.

A wide sidewalk, ten feet wide, ran down both sides of the river, about a hundred feet from the water's edge. On the east side the sidewalk more or less paralleled the road, dipping into the park in a few places. I'd rollerbladed down it a million times, but never at night.

The road was deserted this early in the morning. Bill stopped the car next to a pavilion.

"See this?" Bill asked. He held up what looked like a riding crop, about a foot long. "This is your token. I'm going to leave it on that table over there, under the pavilion. If you retrieve it before I catch you then you'll win the challenge."

He stepped out of the car, walked over to the concrete table fifty feet away. I saw him lay the "token" as he called it on the table top. He returned without a word; we drove on.

Bill pulled into a parking lot. "This is two miles exactly from where your token is. Do you understand the challenge, Staci?"

I nodded. "Y-yes," I stammered.

"Good," he said, "One last chance -- do you want to back out? If so I'll take you straight home."

And screw me until my eyeballs popped out, I hoped. Or maybe not. My voice seemed to come from far away. "No," I whispered, "I don't want to back out."

Bill came around the car, opened my door. Looking at his watch he said, "In that case, your twenty minutes begins...Now! Good luck, Staci!"

I pulled myself out of the car as gracefully as I could considering I was wearing the too-short mini skirt, too-high heels, and semi-transparent shirt. I hobbled over to the walkway and began to walk toward the pavilion.

I should say, I TRIED to walk. I could barely manage to hobble along in the heels. Not only were they too tall the bottom of the shoe was a bit rounded, which would look really good when dancing in a club but prevented me from taking a full step. The skirt compounded the problem. It was just long and tight enough that it had a binding effect on my thighs.

This outfit wasn't designed for walking!

I considered removing my shoes, going barefoot, but I knew there was broken glass on the walkway. Not a lot of glass but enough -- my feet would be cut to ribbons in no time without shoes.

River park was fairly well lit; there was a street light every quarter mile or so. They made bright pools of light in the darkness; however, this made the rest of the park seem darker, more foreboding. I imagined all manner of evil animals, snakes and spiders and lizards, lurking in the shadows, ready to pounce on me.

It was cool but not really cold. This was fortunate as my costume afforded no protection from the elements. My nipples were tight from the wet coolness and my obvious excitement. My hair, braided, hung down almost to my waist and slapped against my back as I walked.

I'd always been proud of my breasts. I've heard most women don't like their boobs, think they're too small or too large. Not me! Mine were just right, 34C, high and firm. They looked much larger on my small frame. Most people guessed me to be a D cup.

Now they jiggled and swayed as I hobbled along. The silky material rubbed against them. It felt soft, like a lover's gentle caress.