"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.