Penny's Worth Ch. 01

A Harder Night

Penny texted Dave on a Friday night. He hadn't heard a thing from her in weeks, and Stella continued to claim no knowledge of her existence. I could tell Dave misses his sluttish plaything.

The message was direct, "Date at 8 usual motel. Penny."

He made a lame excuse to go out at 7, which gave Stella plenty of time to drive to the room and ready herself as Penny.

I greeted him at the door in a red satin skirt, a top that barely encased by boobs and a pair of black stripper heels. I had done my eye shadow in that cheap bimbo look he seemed to favor.

My trick pulled me in close and kissed me with vigor. I allowed him to caress my firm breasts through the thin suede material.

"Do you want me to work as a real-life prostitute?"

"I wouldn't object if you decide to."

That wasn't good enough. I had to have total uncompromising buy in from him. I wanted his finger prints on the deal, so he wouldn't blame me if he changed his mine.

"It's yes or no. Do you want me to sell my ass to other men for money?"

His face said yes. The growing bulge in his pants said a definitive yes. I wanted his mouth to provide his ultimate response.

He thought as if worried that I'd judge him for his decision. We'd both been playing this game for months. We both wanted to see if we'd go to the next step, only held back by what the other might think. He had to make his choice now. "OK - it is yes."

I breathed a sigh of relief. I wanted him to say yes. Now there was one more test of his commitment. "All right. I'm willing to turn out. I want you to procure my first real trick."

Dave's shit-eating grin began to fade. He knew I was challenging him. He'd hinted at my turning Pro for months. I wanted to make sure this wasn't some male based psyche-erotic game for him. "You want me turning tricks, you start me off; that's the deal. You can even watch me fucking my first real John, but you have to bring the guy in."

I stooped onto my knees, drew his zipper down, pulled out his erection and began my specialty blowjob. I looked up to see his face. The gears were turning. He was obviously working out logistics.

I unbuckled his belt and pulled his pants to the floor along with his shorts. My hands began to toy with his balls. In a few minutes I could taste his precum on the tip of my tongue. He seemed distracted. "I'm thinking. I may have an idea."

I took his cock out of my mouth and continued to play with his testicles. "He'd better be good looking."

"He will be. He's very good looking, in fact." Dave began a wicked laugh.

"You have a specific candidate in mind?"

"Maybe. You'll just have to wait and see."

That eliminated an online hookup. That could be dangerous on many levels anyway. It would be better to go through Quinn, but I needed Dave to be the ultimate instigator.

He polished himself off in my mouth. His cum dribbled down my chin and dribbled onto my neck.

If Dave was at all apprehensive about my new vocation, he wasn't showing it. His cock got hard again in near record time, and I ended the evening straddling the bed and being taken doggy style while I babbled how much I'd have loved to have gotten my cherry popped by that quarterback for the WHORE-PAC benefit a few weeks back. I was not so secretly hoping Dave might take the hint.

"You really are a total slut, aren't you Penny?"

"Yes, I am, sir. Would you want me to be any other way?"

~ ~ ~

I came close to figuring out where he came up with my first client. It wasn't the footballer, but Dave had managed to have met a number of other interested men that night at the auction. Since I'd become the star of the show, a lot of them would have loved to have had me. However, at two to three thousand for a half hour session that was a bit rich for even those well-heeled punters.

He arranged the session for the next night and planned to have the gentleman met us at the motel. I wondered if it was be a civic leader, business tycoon or athletic star. It might be exhilarating to fuck someone famous; I thought. As we waited, Dave refused to tell me. The anticipation was making my cooch drip like a cheap faucet.

We saw the headlight of a car pull in front of the room through the curtains. I glanced outside, expecting a Mercedes or limo. Instead, the car was an economy model with a dented front fender.

"It's one of the waiter's from the event. He's going to pay you five hundred. It's a lot for a guy like him. He probably had to work a few nights to get up that kind of money."

I was stunned. I'd arrogantly thought of myself a doing better than a waiter. "Why him?"

"You should have seen the look on his face when you got up on the stage. I could tell he wanted you more than anything. But, you were not available to him, and he couldn't afford you anyway."

I began to feel like a total haughty bitch. Three years ago, I'd worked as a waitress for a few months before they fired me.

"He even congratulated me when I won you. He's a nice honest kid."

"How much of a kid?" I started to worry.

"He's twenty-two. I checked his ID. He was so excited when I said I could hook him up with you."

I looked out the window. The waiter looked nervous, even more nervous that I was. He was also very cute. Not as well built as Dave, but he had a boyish charm with a mop of dark hair and deep soulful eyes.

My heart skipped a beat when he tapped on the door.

As I opened the door his face lit up when he recognized me. "Hi, Jason, I'm Penny." He blushed slightly at his blunder and tried to correct himself, "You're Penny; I'm Jason. Hello."

It was near instant lust for me. I laughed and said, "I'm a little bit nervous, too. It's OK. I'm glad to meet you." He was a slender, but tall. I let myself go and did something I've never done with a person I've only exchanged a handful of words with. I hugged him tightly and began to kiss him. It was a strong and zealous kiss. My shameless tongue found its way into his mouth. I pressed my tits against his chest and ran my hand down to feel the curvature of his ass.

If my husband was in the room with us, I didn't care. I was oblivious to anything other than this complete stranger that I was throwing myself at.

At some point we pulled ourselves apart. His only words was, "Wow." That seemed to say it all for me, too.

After recovering my senses, I turned to look at Dave. He wore a huge grin that said he approved of Penny's flagrant behavior.

I turned around a few times to show Jason the goods. I'd dressed in the same outfit I'd worn to the parking garage a few months before. The young man was nearly drooling with lust. "So, Jason, are you interested?"

He stammered, "I can't wait," before pulling out his wallet. He produced a pile of tens, twenties and a couple of fifties onto the table. He looked slightly embarrassed at the small denomination bills. "Sorry, tip money."

"As long as it's legal tender, it's all good." This made it official. I was doing this for cash. I motioned him to sit in the chair. I sat on his lap and began to kiss him again. He wasn't an experienced kisser, but it didn't matter. It was one of the most exciting make out sessions I've ever had. I periodically opened my eyes. His were closed, but Dave was watching intently, with his cock pressing up through his pants.

Once more, coming up for air. "What would you like me to do for you?"

Jason as so anxious. I hoped I wasn't deflowering him. "We can have sex, right?"

"There are all kinds of sex we can have. Is there anything you'd especially like?"

Jason admitted he wasn't that well versed in advance techniques. Imagine a twenty-two-year-old male, who hadn't been patrolling the internet for every weird act known to man. I suspected he was being shy.

Taking his hand, I helped him stand. "Let me be your guide. I promise, you'll have a great time."

I pulled his sweatshirt over his head and unbuttoned his shirt. Then his jeans were removed. He hadn't bothered with underwear. He was heavily manscsaped, which I liked and had a black tribal tattoo around his bicep.

Presenting myself to him, I had him untie the laces of my leather vest. My breast fell out to greet his curious fingers. I began to moan from his gentle touch. I looked at Dave as he licked his lips with quivering enthusiasm. He's never witnessed another man handle my hooters before, although he had seen them handled by Quinn. It was different seeing another male caress them and begin to suckle their firm nipples. I checked to see that he was nodding with both pride and approval.

"Do you mind if I get naked, too?"

Although outwardly barely cognizant of the other male, he managed to said, "Sure, it's cool." Dave had told me later that the deal he'd struck with Jason was that we'd split the cost of me, and I'd take them both on. But, Jason would get first crack at my pussy.

Jason's hand moved down to remove my short skirt and then rubbed my hot box through the silky fabric of my panties.

"Man, you're so wet."

So I was. This encounter had me so excited, I was ready to do nearly anything. "Put your fingers in me. As many as you can fit."

He ran all four into my gash, and I came quickly. It was like throwing a thimble of water onto a textile warehouse inferno. I wanted more stimulation, way more.

I lay on the bed and spread my legs. Jason mounted me and became to pump. He may have been slender, he was wiry and strong. I came again, as Dave looked down on me. He was stoking his cock and finally came on my face. I swallowed as much of his spunk as I could and wiped the rest away with my hands.

It wasn't that much longer before Jason came inside me. I could feel his jizz shooting into me. He remained in place as his cock began to relax. Then in a few short minutes, he began to grow hard again - the abilities of a young man. Even my more experienced husband couldn't match that kind of exuberance.

Once more, he began humping away at me. I suggested changing positions and as he lay on his back, I insert his cock into my vagina with my ass facing his legs. Dave managed to jam his cock into my asshole and the two men rocked me back and forth. Waves of sensation washed over me and I came yet again.

I was fucked that night by two men in positions I've never seen expressed in Cosmo. All I know was that my first experience as a whore lasted for hours.

Dave was the first to leave, having dropped his money on the table. I sucked off Jason for another half-hour and, he managed to leave a decent deposit in my mouth.

When he finally departed, I attempted to recover on the mattress with the sheets more off the bed than on. I looked at the money on the table. I was now a "sex worker" as Quinn liked to describe it. To me, the term "whore" seemed deliciously appropriate.

I only wished I'd had the energy to find another trick for the evening, but I was exhausted. That would have to wait until another time.

~ ~ ~ End of Chapter 1 of 12 ~ ~ ~