"Would you like to have sex with Brittney Spears?" a man furtively asked me, as I passed a non descript doorway on Valencia street.
"You'd have better luck trying to sell me a piece of the true cross," I said. I mean who would believe it, Brittney Spears inside of a grimy building in San Fransisco, selling herself as a whore.
"Come inside, take a look. I promise you won't be dissapointed. And if you aren't, perhaps we can come to an accomidation."
I tried to stare him down. I have a fairly strong bullshit detector, but there was something authentic about this man, even if he was telling the truth he was nothing more than a pimp with an attractive proposition.
I nodded and went into the door he indicated, wary of someone waiting in a dark corner with tire iron. I could not tell who would be more foolish: the guy who dreamed up a mugging scam that promised sex with the most desirable woman in the world, or the idiot taken in by such a scam.
But there was no 800 pound gorilla waiting for me, just a beautiful woman bent over the arm of a couch, her ass facing me, along with a wet cunt, topped by a clitoris which was obscured by her hand as she masturbated intently. I could not tell if it was, in fact, Brittney Spears, but she had the right body. Truth be told, I hadn't owned a TV in years and wasn't sure if I would recognize her anymore. With that ass stuck in the air the way it was, and the wonderful smell of wet pussy filling the dank room, it didn't matter if I was fucking Brittney or some skank who bore a faint resemblance.
"A piece of the truth cross, eh?" said the man, whose presence I had forgotten about. "Only $500."
"Can we go to an ATM afterwards?" I asked him, my eyes never leaving her hands as they sped up massaging her clit, bringing her closer and closer to orgasm. From six feet away I could tell she was close.
"I trust you," the man said.
"What are the rules?" I asked.
"Whatever you desire," the man said. "As long as you don't hurt her, and do what she asks. She enjoys anal, just go slow. Like I said outside, you won't be dissapointed."
"You have someone for me, Max?" she rasped, her breath heavy from excitement.
"I think so," Max said. "Brittney, I'd like you to meet..."
"Jeff," I said, providing my real name. Now, I would never see a prostitute, but if I did, I think I'd be savvy enough to use a false name. With her presence, suddenly my dick was doing my thinking and I had blurted out my real name.
"Come here, Jeff. I haven't had any cock today, and I miss it so badly. Come over here so I can get you hard." Since she was leaning over the arm of a couch, I assumed she meant for me to sit down, so I did.
"Let's see what we have here, Jeff," she whispered conspriatorially - I felt like, for whatever reason she didn't want Max to hear what she was saying as she removed her hand from her clit for the first time since I entered the room and fished my modest cock out of my trousers. "You've got a nice one here. Not the biggest I've ever seen, but nice. And it's clean, it only smells like man and cum, which is the way a cock should smell, not of sweat and cologne." She took me into her mouth, just the head of my dick, swirling her tongue around, as if she were waiting or me to get really hard so she could do her job in earnest.
"I like the way your dick tastes," she said, and giggled. I still could not tell if it was actually her, but something about that giggle was familiar - perhaps I saw an interview with her years ago, and that laugh was back.
She went to work on my cock. Normally I don't really get into blowjobs. Don't get me wrong, I enjoy them, but they rarely make me cum.
This one was different. It is impossible to describe what made it so much better. I think it was the affection she showed for my cock that made it so much better. She seemed to enjoy it, not like the way it was with my girlfriends who went down on my in exchange for lengthy cunnilingus. She - Brittney - seemed to love going down on me. She seemed to enjoy it so much that when I told her that I was about to come, she sucked even more earnestly. She grabbed my ass and pulled me closer to her, so that the head of my cock was inside of her throat, and I could feel it constrict as she swallowed rope after rope of my cum. She would not let me go even as I softened in her mouth, pulling me out momentarily to say, "I need to get you hard again so we can fuck." She began to stroke me as she took a testicle into my mouth and massaging me with her tongue. I wasn't expecting more than one orgasm from a prostitute, but she was ready to go. So was I, as it happens, she had done such a good job in getting me erect again.
She sat down on me, straddling me, taking me up all the way inside of her in one motion, a velvet glove grabbing me cock tightly. She pistoned up and down on my cock, doing all the work, which was good since I had no energy left after that draining blowjob. Twice she shuddered and a jet of cum squirted out of her, wetting the pants that were still bunched around my ankles. After her second orgasm, she collasped against me, unable to move, my cock still buried deep inside of her. But I was just getting started, my energy returning. I hoisted her up and set her back in the position she was in when I first entered the room, leaning over the arm of the couch. Her cunt was right at groin height, and with no preliminaries, I thrust myself in to the hilt, my balls slapping against her ass. It seemed like hours I spent pounding her with no finesse, just taking her from behind. It became impossible for me to keep track of her orgasms, it seemed like she was machine gunning them unto my cock; her cum was everywhere.
Finally she cried out, "No more, I'm just too sensitive," but I was still hard, and was not going to be dissapointed. She hung over the couch limply, and I slowly pressed the head of my cock into her pink rosebud of an ass. Pretty much everyone in the media admits that, for most men, the ultimate fantasy is to fuck Britney Spears. Jack Nicholson said it would be life changing. But I think the secret fantasy, the one i was living out, was to fuck her in the ass. I eased my way in, her copius cum providing all the lubrication we needed. She gave a low moan, different than the sounds she made when I was in her cunt, baser, more primitive. She becamse an animal with my cock in her ass. She brought her hand back down to her clit and began to strum herself again. I forged my way, deeper and deeper into her ass, until I was all the way in - her perfect bubble butt prevented me from getting me in to the hilt, but hwere I was felt pretty damn good. I slowly pulled out most of the way, leaving just the head of my dick inside of her, and I could hear her exhale, waiting for more.
Slowly, I filled her up again.
"Harder, dammit," she groaned, and tried to push against me.
I pushed a little harder.
I slammed into her all the way, and she shrieked with pleasure, and gave that telltale shudder. All of her holes constricted - I could see her cunt clench, and feel her asshole begin to milk the cum out of my cock.
Four more strokes and I was done. I shot my cum deep into her rectum. I collapsed on top of her, both of us panting. When I finally rolled off of her, and pulled up my pants, which were stained with her cum, she told me to forget about payment.
"That was too good to accept money for. This one's on me, Max," she said to her pimp. He looked slightly disgusted, but I'm guessing she could afford it.
"You won't tell anyone about this," she said to me, "right?"
"Who would believe it?" I asked. "Can I see you again?"
She gave me a sad smile, and I knew the answer. On the way out, Max gave me a toothpick.
"A piece of the True Cross," he said.