A man with a proposition

I held my eyes closed for what seemed like an eternity. I could taste old man cum and cheap liquor on my tongue. I could feel it coating my mouth and throat, It tasted as disgusting as it sounded. And yet … the feeling was thrilling. I was as horny as I had ever been. I hadn’t really had any release of my own during the encounter, and I could feel the dampness between my legs growing and the sensations associated with it becoming harder and harder to ignore.

When I finally did open my eyes I found the bartender standing directly in front of me. Grinning stupidly, he said, “I knew you were a whore the second I laid eyes on you.” I smiled, thinking of all the nasty things I wanted to do. The bartender took it as an invitation as he reached his hand toward my breasts. Unfortunately for both of us, another hand took a grip on his wrist before he made it.

“Sorry, kid, that was her last freebie,” a new figure had taken the newly vacated seat beside me. I adjusted my dress to cover up a bit more and took stock of him. He was much more attractive than the previous occupant, dignified, even, in comparison. He was probably in his late 30s, and was dressed like a businessman. From his appearance, it seemed that he would be as out of place here as I was, but from his demeanor, he was clearly comfortable.

“Fuck, I should have known she was one of yours, Ray,” the bartender was despondent as he pulled his hand back, out of the new man’s grip. He continued to leer at me as he considered, “How much?” I couldn’t tell if he was asking me or Ray. I opened my mouth to respond, not really knowing what I was going to say.

“I think that’s enough for tonight, don’t you?” Ray pre-empted me. This time I knew the question was directed at me. I nodded, meekly. The bartender, clearly frustrated, walked away in a huff. I watched him go, and felt a bit of regret. I was still horny, and he looked like he was ready to help me find release. “Quite a show, miss …”

“Irene,” I responded, instinctively. I felt for a moment like I shouldn’t have revealed that, but it passed.

“That’s a very pretty name for a very pretty girl,” he smiled. It was infectious; I smiled back. “My name’s Ray, and I think you may have been looking for me without even realizing it.” Everything Ray said seemed to have an air of mystery to it. After only an introduction, I felt as though he was about to take me on some grand adventure. He was lucky; I had never felt so adventurous.

“I’m looking for a lot of things tonight,” I said, quietly, trying to match his mysteriousness with some of my own. He cocked an eyebrow and chuckled.

“From that display you put on, I’d say you’re looking for a lot of one thing tonight,” he said. I blushed, finally fully picturing what I must have looked like just a few minutes earlier. “Don’t be embarrassed; it really was impressive. Hell, it brought me here to you, didn’t it?” I wasn’t sure if he was trying to humiliate me or not, but when I caught his gaze and saw his smile again, I felt reassured he was being sincere.

“Thank you,” I mumbled, sincerely. Still, I was getting impatient. “What exactly is it you want?”

“We’ll get to that. But, first, what is it that you want?” It was like he was playing a game with me, trying not to reveal too much too soon. I played along. I contemplated the question. I looked over at the bartender, now as far away from us as possible, still sulking. I felt the familiar sensation below my waist. I thought about Paul and what I thought had been our future and felt a pang of guilt surge through me. I looked up at Ray; he was still wearing the same smile, but for the first time, I felt his eyes devouring me; the guilt faded. I didn’t owe anything to Paul. Not tonight, anyhow, not after the way he left me. The only reason I was sitting here, the only reason I had done the things I had done was because of his cruelty.

I put on a seductive smile and put my hand on Ray’s crotch. “I know what I want …” Ray, unexpectedly, brushed my hand away. But, the smile didn’t leave his face.

“We’ll get to that, too.” he whispered. “Answer the question.” I sighed, frustrated. I thought again for a moment.

“I want a new life,” I told him, truthfully. He nodded, as if he had known how I was going to answer.

“Well, then, I was right,” he stated, matter-of-factly. “You were looking for me.” I was going to ask what he meant, but before I could, he stood and motioned to the door, “Come with me, Irene; I can give you exactly what you want.” I was too intrigued to decline. I followed him outside. He led me to his car, a luxury sedan, and held the passenger side door open for me. I sat and inhaled deeply. I loved the smell of leather seats. I looked idly out the window as he got in and started the car. I did my best not to think about what I was doing, or where we were going.

The ride was long, back into the “good” part of town. We spent some of it in silence, before he spoke, “That was the first time you ever did anything like that, isn’t it?” I nodded.

“How could you tell?” I wondered if it was so obvious.

“Most women don’t wear their wedding rings when they do things like that.” He looked over at me as he said it. I looked down at my ring; I didn’t want to see the judgment on his face. “Relax, Irene, I don’t want to know what happened in your marriage to lead you to me. I told you, I’m here to give you a new life; your old one doesn’t matter anymore.” I smiled; it was what I wanted to hear. We rode the rest of the way in silence. Finally, we pulled up to a big house in a much nicer neighborhood than mine.

“This is yours?” I asked, clearly impressed. “Does my new life include a house like this?”

Ray laughed. “It might. The best of my girls live right here with me,” he got out and came around to open my door. I finally realized what he meant by “a new life.” He opened my door and helped me out. “Some of them make up to a hundred fifty a year on their own.”

I was shocked, “I didn’t know hookers could make that much.”

Ray laughed again. “They started out as hookers. But, they worked their way up. Now some of them make movies for me. That’s where the real money is, Irene.” He led me to the front door. I wasn’t sure I wanted to go in, and Ray could tell. He looked at me, “Yeah, you’d have to prove yourself first, just like all the girls. There aren’t any shortcuts in my organization, but if you’re willing to do the work, I’ll give you everything you’ve ever imagined.”

I was still hesitating, “So … girls start out working for you as whores and work their way up to porn stars?” I hadn’t meant it to sound so condescending. Ray’s smile went away for a split second, and I saw him getting irritated, but the smile came back just as quickly.

“Well, it’s more complicated than that,” he explained, “there are a lot of steps between the bottom and the top, and who’s to say what the top is for you? My point is, there are opportunities to do just about anything if you stick with me.” He could tell that I wasn’t sold. “But we’ll get to that,” his expression changed. His eyes were devouring me again, and he put his hand on my waist as he pushed the front door open. “For now, let’s just take care of that other thing you wanted.” I smiled and let him lead me through the door. Even if I didn’t want to become a whore, I definitely was ready to give in to Ray’s charm at least for tonight.

He leaned down and kissed me. My mouth had been invaded earlier in the night, but this wasn’t like that at all. It was strong and deep, but sensual. When we broke, I let out a satisfied sigh. Ray took my hand and led me up the stairs. I took the time to notice the ornate decorations and tasteful style in the house. Ray led me into the master bedroom. The bed was a plush California King with what looked like silk sheets. I couldn’t wait to feel them wrapped around me as he fucked me. His hand moved from mine and he began fondling my ass as I gawked at the luxury that surrounded me. I turned to face him and kissed him again. “Get on the bed,” he said. It sounded more like an offer than a command. I accepted and fell blissfully onto the incredibly comfortable mattress, kicking off my shoes in the process.

I was on my back with my eyes closed, sprawled across the covers when I felt him hovering over me. He was above me, his face inches from mine, hands, working their way under my dress to the elastic of my panties. As his fingers hooked into the waistband, I leaned up and stuck my tongue into his mouth once more. He slid my panties down my legs, and I lifted myself to help. We made out for what seemed like ages, with one of his hands snaking up my body under the dress to reach my breasts. The other stayed at my pussy, gently teasing me, driving me mad.

“Oh, God, baby, no more, I need you now,” I whispered, my lips breaking our kiss and touching his ear as I spoke, desperately. He pushed himself backward and took his hands from under my dress. A feeling of emptiness washed over me abruptly; I opened my eyes and saw him unbuckling his belt. I saw him smiling down at me. I loved his smile. I took the opportunity to pull my dress off and tossed it aside. When I was done, Ray was back on top of me.

He used one hand to gently place the tip of his cock inside my pussy. He moved the other hand underneath me for support. Slowly, he pushed himself into me, taking care not to make me uncomfortable. Eventually, he was fully inside my pussy, his ten inches reaching parts of me I had never felt touched before. He held himself there for a moment before pulling back and thrusting back in. He repeated this action a few more times and picked up speed, until I could feel my tits jiggle with each thrust. In only a few minutes, I came for the first time, letting him know by whimpering and moaning loudly underneath him.

Unfazed, he kept pounding away at me. I tightened my thighs around his waist and began to rake at the smooth skin on his back. I couldn’t believe it, but after only a few more minutes, I felt myself losing my breath again, feeling goose bumps over my entire body. My pussy tightened around him as I came for the second time. This time I screamed. He kissed me again to muffle the noise. Still, he kept fucking me. He was amazing, finding new spots inside me with seemingly every thrust. Beads of sweat formed on my body as I writhed delightfully in his grasp. I came twice more before I finally felt him tense up on top of me. He released what seemed like an impossible amount of cum inside my thoroughly used cunt and fell forward onto me.

We laid there, panting, occasionally leaning in to kiss each other. Eventually, we found our way under the covers, and he fell asleep. I, on the other hand, had a decision to make.