Thirty Days Down Day 01

Cindy shifted the gearshift up to first, so the stick wouldn't poke her belly and then she smiled that shy super smile that women do when they know you about to totally go under their power. Then she leaned down and across and unzipped me and started in to sucking my dick. The tops of her breasts rubbed against my thigh. I reached across while she bobbed up and down and undid her bra strap, then reached my hand in to cup her breast. It was soft and heavy, the nipple hardening into the palm of my hand. I hefted it and then stroked it.

With my other hand I moved her dark hair away from her cheek, picking away strands that were stuck by spit to her face, and then I leaned over to watch. It is endlessly delightful and fascinating to watch your own penis go in then out of another person's face. The veiny shaft covered and revealed, covered then revealed, the way her lips pull down, almost fighting to stay in place, pulled away from the face with suction.

I could feel her tongue pushing hard circles around the head of my penis. One hand cupped my balls.

I relaxed into it and let go from holding back and let the motion of her mouth carry me, move me until my whole body was rocking in response to every suck every entry every motion, all in rhythm with the music from the bar we'd just stepped outside from. She felt the change and responded to it and went with it. She picked up the pace. I was ready.

I leaned down and kissed her ear, and my chest pushed against her head, forced it down onto my penis. Cindy opened her throat and took me all the way in until her lips brushed pubic hair and her nose pushed into my abdomen and when it did, I exploded. I cried out and leaned back against the headrest and Cindy pulled back until her mouth only covered just the head. She stayed right there and sucked and swallowed until I was dry.

There is always a moment after a stranger gives you a blowjob that is extremely awkward. Its like, "okay, now what?" only not just that but also wrapped up in judgment and consequence. After anonymous sex, rules for polite society having already been banished, we are left with only each other, floating. In order to stop it, and it must be stopped because that kind of naked vulnerability cannot be borne without love, you either got to fuck or make small talk.

I rolled down my window. I closed my eyes and found then lit a cigarette in the darkness I'd made. I breathed out the smoke. "That was nice," I said to the night sky.

"You liked it?" She said.

"Yeah, A lot."

"Later then, you got to fuck me." That was a question, too.

I made a face like when a favorite aunt gives you a sweater for Christmas. "That is a deal," I said.

She patted my thigh three pats and then walked back into the bar ahead of me so her boyfriend, maybe ex, maybe not, sort of thing, wouldn't see us together.

I finished my smoke and then went back to the bar.

I sat alongside the rail at a small two person table far enough away from the dance floor and the music so that a conversation might actually be possible. I sat alone. The waitress brought me a scotch. I thanked her and tipped her and she let her breast brush against my shoulder on her way past me toward the next customer. I leaned over and followed the motion away from me.

When I looked back up there was an old man sitting at my table. He was maybe five feet tall. Bald, wrinkled all over with white wire eyebrows that shot straight out about an inch over eyes in an ugly tangled mess. His ears were too small for his head.

"Hello," I said.

"Something of a Casanova, are you?" He asked. His voice was high-pitched with an obscene wheedling quality to it. I didn't like him, or trust him one little bit.

"Who are you?"

He chuckled, "Call me Tiny," he said, as if it were the funniest of jokes, like maybe you'd call a big fat guy Tiny for a nickname.

"Who are you, Tiny?" I said, trying to put scorn into my voice.

The music, the mindless monotonous drumbeat of the dance music seemed to somehow work its way under us, like an underline, as if significant somehow. I wondered if my drink had been spiked.

Tiny said, "I will bet you one million dollars, cash, that you cannot have sex with one-hundred different partners in thirty days or less."

"You're fucking high," I said.

"I will let you hold the cash. You can even spend some." This he said with great satisfaction. He knew, obviously, that it was a deal clincher. That anyone would have to say yes if the money was actually in their hands.

I tried to call his bluff. "Let's see the money."

He reached under the table and pulled out a large bright red duffel bag. It was heavy duty nylon with large reinforced zippers. It thunked onto the table top, solid. He unzipped it partway. It was full of hundred-dollar bills. "Inside this bag, are ten thousand hundred dollar bills. All real. All new. All legal. And all tax free." His voice was wheedling double time now. He almost was panting.

I looked all around for maybe the hidden camera or something. "This is a joke, right? You can't be serious."

He leaned over the bag until he was in my face, too close. I didn't pull away even though I wanted to. He said, "I am very serious."

"But what's to stop me from just taking the money and running?"

He laughed. "You let me worry about that," he said. This time I believed him. I believed him all the way, about everything. In that second I understood three things. I knew that I could never trust Tiny. I knew that Tiny never lied. And I knew that I should just walk away and not take the bet. That the bet was bad, bad as in deep seated terrible.

"Okay, I said. I'll do it."

Tiny stuck out his hand. I reached over and took it. When I did, I shivered involuntarily like sometimes after you piss.

Tiny said, "I'll even count that blowjob in the parking lot. Ninety nine to go."

I knew I could do it if I tried hard enough. I did the math in my head. One hundred divided by thirty was three point three, three, like that forever. So I had to have sex three times per day with three different women and one day with four, and maybe another day with five in order to make up for tonight. Tonight I was all of a sudden exhausted. Tonight I was going home. I motioned to the waitress.

"Can I buy you coffee after work?" I asked.

She smiled. "How about you make me coffee?" One-thirty, pick me up, okay?"

Okay, I said, but she was already moving past, dealing with customers. I turned to smirk at the old man. I wanted to say, see how easy this will be. He wasn't there.