For a long time I’ve entertained sexual fantasies of being a prostitute. I get turned on by the idea of picking up rich guys in suits at hotel bars and getting paid to fuck them. I like the aura of sexual power that surrounds a woman who sells her body for a high price. While I could never actually be a whore—there’s just too many emotional and practical issues at stake—I wanted to feel like one. So this fantasy turned into reality the night my boyfriend agreed to be my trick.
Jeff and I have always had a very experimental sex life. We’ve taken turns fulfilling each other’s fantasies. They started out fairly simple. I gave him a blow-job while he was driving on the interstate. He whispered naughty stories in my ear about fucking me in church while I masturbated. I did a striptease for him. He gave me phone sex while I was at my office. Eventually these dream-cum-trues became more elaborate and more exciting and I finally sprung the prostitute idea on him.
"Have you ever been to a prostitute?" I asked. He said no, mainly because he wouldn't know what to do, or what to say.
“What if that prostitute was me?” I smiled coyly.
"Well, then I’d have all kinds of things to say and I'd know all the right buttons to push.” So I described my plan in detail.
I wanted him to meet me in a ritzy hotel bar after work for a drink, around the corner from his apartment. He had to wear his most expensive Italian suit. I would be wearing a very low-cut red mini-dress, heels, and perfect make-up. He would approach me, and pretend not to know me and the fact that I was a hooker. He'd have to buy me a drink and try to seduce me. Then he’d find out that he had to pay for me.
Once he took me back to his place, I wanted him to be cool and aloof, and say really hot and nasty things to me. Then he’d have to pay me, fuck me, and I would get dressed and leave. As I described the details of my fantasy, I could see his cock getting hard through his jeans. Just talking about it made us both so incredibly hot, we fucked right there on the spot.
The appointed day finally arrived. I took a long, hot bath and perfumed every inch of my body. I even shaved my pussy and then put bath oil all over it, inside and out, and rubbed my finger over my clit until I was very hot, but I did not let myself cum. I slipped into my most provocative lingerie, red dress, and spike heels. I applied my make-up carefully. I entered the bar, walked right past him and took a seat. I ordered a very dry martini. Out of the corner of my eye, I could see him staring at me. He looked absolutely gorgeous. Men in suits drive me wild! He waited until I had drained my glass, and then instructed the bartender to fix me another cocktail.
"This is from the gentleman over there,” said the bartender, pointing to Jeff. I raised my glass in appreciation, and Jeff slowly came over to join me. We made small talk. He asked me my name, complemented me on my good looks, told me what he did for a living.
"What do you do?” he asked.
“Oh, I work in the service industry," I replied.
"And what kind of services do you provide?"
"Anything you want," I said, "if the price is right."
He feigned surprise. He told me how desirable he found me, and that if he had to pay for me, he would.
“I’m one hundred dollars an hour. Can you afford me?" I asked.
He paid the bar tab and escorted me out of the hotel.
Once we were inside his apartment, he took my coat and led me to the center of the room.
"I just want you to stand there for a minute while I look at your body,” he said. He circled around me and made lecherous comments. "I like your mouth, your red lips. I’d like to see my cock going in and out of that precious mouth. I like your tits. I might want to fuck those tits with my cock. I like the shape of your ass, too. Maybe I’ll make you bend over and take my cock up your ass. You'll do anything for me, won’t you?"
"Yes," I replied, "but you've got to pay me first."
He took out his wallet, dropped a hundred dollar bill on the floor. “Pick it up," he ordered. I did, and put it in my purse. I walked back to the center of the room. He unzipped my dress and let it fall to the floor. I was wearing a red lace bra, garter belt and stockings, but no panties. From behind, he cupped my breasts in his hands and started squeezing them, softly at first, then hard, very hard. He rolled my rock-hard nipples back and forth between his fingers, while he pressed up against me and I could feel his hard cock. He spun me around and tried to kiss me, but I turned my head.
"The only thing I won’t do is kiss you.”
"Just like a whore,” he whispered. "Get down on your knees.”
I knelt down in front of him and followed his instructions.
“Take my cock out of my pants. Now suck it."
I took just the head of his cock into my mouth, sucking it slowly. I ran my tongue along his shaft and eventually swallowed his entire prick. I sucked his cock with wild enthusiasm, as I watched the look of ecstasy spread over his face. He stroked my hair and told me what a good whore I was.
“I’m going to fuck every hole you've got, because I paid for every hole. Now stand up."
He led me over to the dining room table and told me to bend over and spread my legs. With my hands on the table, I did what the customer wanted. I could feel his fingers playing with my soaking wet, oiled, shaved pussy, teasing me. Then he shoved two, then three fingers inside me and began jamming them in and out of me. He demanded that I tell him how much I wanted him to fuck me.
"I want your cock inside me so bad. I want your thick, beautiful cock inside my cunt. I want every fucking inch. I want to please you so bad."
"Why? Why do you want to so bad, Isabella?”
"Because I’m a whore. A slut," I said between breaths.
“That’s right. A dirty fucking whore, who spreads her legs for any man. And now you're going to spread your legs for me." With that, he slid his dick into my cunt and began fucking me with a fury that I've never experienced before. He was ramming me so hard, I thought the table would break. Then I felt his finger press against my asshole. I relaxed my anus by pushing out, just like a pro, and felt it part and open as his finger slid up my ass, moving in and out with the rhythm of his cock. He kept making me tell him how I liked getting fucked in both holes at once.
“I like a big cock in my pussy and one up my asshole. I like to get both holes filled with so much cock I can barely stand it. Fuck me, please fuck me,” I cried.
I could feel his grip on me get tighter and tighter. Then he pulled out of my cunt and I knew what was coming next. “Don't working girls get paid extra for this?” I thought to myself as I felt his cock press against my asshole and then it slid into me, filling me all the way to my throat. Then I knew he was going to cum. He pulled his cock out of my ass and came all over my butt. I felt his thick warm cum run down the crack of my ass, and down my legs. He began rubbing his cum over my butt, then took his sticky fingers and ran them over my lips.
"Eat it," he whispered. I licked every drop of cum off of his hand. I was still bent over the table when I heard him zip up his pants. "Get dressed," he commanded. I freshened up and got ready to leave. He walked me out to the door, and this time I let him give me a kiss on the cheek.
"Maybe I’ll need your services again," he said with a smile.
“Maybe you will.” He closed the door behind me. I went down to the lobby, waited a few minutes and called him on the house phone. He invited me up.
He opened the door and gave me a long, hard kiss. "You look suspiciously like a prostitute I once knew. Some day I’ll tell you all the wild things she did to me." We both laughed and fell into each other’s arms.
—Isabella B.
