Penny's Worth - Chapter 1 - Sex Stories

Penny's Worth - Chapter 1

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. “Okay – 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 ...