I got out of the meeting and walked through the door to the outside world. The heat was heavy as the warmth rose off the concrete and tarmac of the busy city streets. I loosened my tie. Squinting up at the sun, I took a deep breath, stepped out onto the street and thought back on the events of the last hour.
My business partner and I had a presentation with some potential investors, and even though it had been a success, I simply wasn't cut out for this type of endeavor. I was the artistic, creative side of this relationship, so felt stifled by talk of numbers and profit, and started to drift. From now on, I would leave that boring stuff up to Jimmy and just be fully absorbed in being an artist.
It felt good to be outside and I closed my eyes as a cool breeze swept across me. The city was alive and I felt free, so I walked around a little before heading back to my car. I had nowhere to be, no one waiting for me, so I just wandered. I walked past restaurants, a park and a strip mall then headed down a side street that I'd never been down before.
The vibe changed. I was in a seedy part of town all of a sudden and noticed I was walking past porno theaters, strip clubs and strange little hole-in-the-wall places selling sexual paraphernalia. I didn't think places like this still existed, but here they were.
Then, there were a few streetwalkers out and while I looked them up and down, I didn't partake. I started feeling a little twitchy, however, and a pretty girl to fuck sounded pretty good right about then. I hadn't ever been to a prostitute before, but had thought about it on occasion. It was a fantasy I'd often had but the right opportunity had never arisen. Fuck it, if the right girl came along now, I would see where it went. I deserved a celebratory treat.
I took a detour, not wanting to go home just yet. This part of the city was too interesting to just rush through, anyway. A few blocks up, I noticed a guy leaning against a wall. He looked at me, nodded, then said "Hey." He was wearing a shirt and shorts and didn't look like a drug dealer or a Scientologist. He didn't look like a pimp either, but I slowed down and looked at him quizzically. He gestured with his head for me to go over to him and for some reason I did.
"You looking for a girl, man?" he said to me. Maybe I was. He must have read my mind, or maybe everyone in this part of town was looking for something.
"Why, what's up?" I asked him.
"She's young and hot. You wanna come meet her?"
Was he for real? Was this a trap? Was he gonna take me in the alley and try to rob me? I was a pretty tough guy and bigger than him so I figured I could stay out of trouble. Plus, I was feeling weirdly dangerous, like a beast liberated after being held captive. I'd had a drink and was feeling loose. I kinda wanted to see where this was going.
"Yeah, maybe. What's the deal?" I was actually thinking about this.
"She's really cute. She can suck your dick or you can fuck her."
"Well, I..." I started to feel uncomfortable now, out of my zone, so I just shrugged.
"Whatever, man. You wanna fuck a teenage girl or what?"
I stood there with the sun beating down on my head, weighing up the pros and cons of the situation. I wasn't particularly worried about my personal safety, but more the moral implications of paying a young woman for sex, and then her paying a pimp. It felt dirty, but then I realized that was what I was looking for, something dirty, something extreme. I was bored and needed inspiration.
He walked down the alley and then turned to me. "Come on," he said and I followed him, keeping alert. I found myself in this little courtyard area between a couple of buildings and this dude was standing by a young blonde girl. She was super cute and not looking like she'd been doing this long. She didn't have the jaded, hardened appearance normally associated with the profession and I immediately felt for her.
"Well, what do you think, man? You wanna fuck her?"
I was now faced with a dilemma. She was hot as hell and I could afford it, so it wasn't a matter of money or desire. If she had been some older chick, or someone who looked like they might be a seasoned professional, I probably would have gone for it. But this girl looked sweet and innocent, like some of the younger girls I saw in my neighborhood. I felt bad for her and wondered what was going on.
I shook my head and turned to leave. I heard her voice calling to me, "Please Sir," she said pathetically and I turned around. Her voice chilled my heart and I wondered why she had asked me back. I looked at her and saw pain in her eyes. What the fuck was going on? Now I felt like I couldn't leave her, so I walked over.
"OK, how much?" I asked her, trying to be gentle.
"Hey dude," her pimp said. "You negotiate with me."
"OK."
"She'll suck you off right here in this alley for eighty bucks. Or there's a room through that door with a bed and you can fuck her for two hundred."
I didn't exactly know what I was going to do once I got in that room, if I was going to fuck her or just ask her what was going on, but I wasn't going to leave. I looked in my wallet. "I have a hundred and fifty. But I want it all," I told the guy. I wanted to get her alone now.
The girl just stood there, trying to smile and look pretty. He scowled. "Fine. Just gimme the fucking money. It's through there. You have thirty minutes," he said and pointed to a door. I gave the guy the cash. The girl took me by the hand and walked me over, then opened the door and I looked inside. It was a small, dimly lit room with a mattress on the floor; pretty grim. There was a sheet on the mattress, but I assumed it wasn't clean.
I don't know how many times this poor little thing had been fucked in this horrible room, but I couldn't imagine she'd been doing it very long. "What's your name, sweetie?" I asked her, trying to be kind. I still didn't know what I was going to do, but I closed the door behind me.
"Tiffany," she said, moving towards me. She stood on her tiptoes and kissed me, then started stroking my tie. I touched her waist and was transported by her presence. She reached down and unzipped my fly. She got on her knees, took out my cock and started toying with it with her tongue. She looked up at me and took it in her mouth. She had been instructed well. I stroked her hair and all the ideas I had about not fucking her vanished completely. I justified in my mind by telling myself I was being gentle with her.
She took my cock out of her mouth, and she was out of breath. "Come on," she said and led me to the mattress. She sat me down and slipped her dress over her head. She had deliciously budding little apples and I couldn't resist touching her. She lay down and opened her legs for me and morally, I was a lost cause. I kissed her blooming rose and she reacted a little to my kiss. She arched her back as I worked on her clit with my tongue, and I don't suppose any guy had ever really done this to her, at least in this room.
She let out some sighs and moans and I could tell she wasn't faking it. I wanted to make her come so I kept going, lapping at her rosebud as her pulse quickened and juices flowed. "Oh! Oh....wow...you...uh..." is all she could say as her climax hit. She lifted her legs in the air and let out some lovely squeaks and squeals of pleasure. "Damn..." she said and looked at me. "No guy ever...um..."
"Made you come?" I said. I felt a little better about taking advantage of her bad situation. She nodded sweetly, looked embarrassed and then I felt really sorry for her. She was a real sweetheart and shouldn't have been doing this job.
"You wanna fuck me now?" she said, then looked down by the side of the mattress.
She handed me a rubber and I slipped my trousers and boxers off. She stroked my cock a little to get me ready and I put the condom on. I lay down. She sat astride me and pressed herself down on my cock.
"Oh!" she said again, involuntarily. I was a big guy and she was tight and tiny. I held her around the waist and eased her down on my cock, slowly. She made a face that told me it hurt a little, so I asked if she was OK. She smiled and then started grinding on me. "I'm fine, thank you, Sweetie," she said and although I was too far into this to change my mind, I felt horribly guilty again.
I sat up and kissed her. She put her legs around me and it actually felt like we were making love, not fucking. I caressed her tiny titties as her ass moved up and down on my shaft. "That feels good, baby," she said. I didn't think she was lying, although obviously she'd been instructed by her pimp to call her clients "Baby" and "Sweetie."
"You are beautiful," I said, and she cuddled up to me. I held her close as I felt my orgasm rise. I told her I was gonna come and she sped up, and started really grinding on me, though I didn't thrust into her. I didn't want to hurt her. We were both moaning, groaning and sweating and she giggled as I nibbled on her ear. I played with her titties some more as I exploded into the rubber. I would have liked to have filled her with my cum, and to have really given it to her hard, but it was better this way. She kissed me again, and smiled sweetly.
I carefully pulled out and she lay down, stretched out. She was out of breath and looked at me, appearing a little less vulnerable than before. "What's your name, Sir?" she asked me.
"Richard."
"Thank you, Richard. You were much nicer to me than the others." I felt bad for her again and I could see her mind was racing. "Richard, You...wanna...um...see me again?" she asked shyly, but with wide eyes.
"What do you mean?" I replied.
"Well, I...um..." She was afraid, I could tell. She was trembling a little bit and her face was white. "You were nice and kind to me but those other men, they..." It looked like she was going to cry and I felt horrible.
"They what?" I asked her as gently as I could.
"They hurt me," she said softly and looked away. I noticed a bruise on her side. I was speechless. She looked at me again, "Will you come and see me again?" she said with desperation in her voice. What was she really asking me here? She was obviously miserable, with good reason, and wanted out of this. Now that I'd had my disgusting way with her, my moral indignation returned.
