My girlfriend, Helen, and I have a great relationship. She s an actress, and so she brings a lot of inventiveness into the bedroom. One of our favorite things is role playing, which we do every chance we get. We ve played out several fantasies: teacher and student, master and slave, pretending to be shipwrecked on a desert island, etc. But there was one fantasy I hesitated bringing to her attention. I wanted her to play the part of a hooker.
I have long held a fascination for high class call girls. I guess it started way back with the film Klute. I frequently peruse prostitution ads in underground newspapers and get quite a thrill fantasizing about visiting a play for pay gal. When the Mayflower Madame business was big news I was beside myself with excitement. In reality, however, I knew I could never visit a house of prostitution. It just doesn t suit my personality, and I was convinced the actual experience could never match my fantasy.
When my birthday rolled around, Helen asked me if I had any special fantasy that I d like her to enact. I figured now was my chance to level with her.
What would you think of trying to play the part of a call girl? I asked. She looked at me quizzically. I would be your client. Our scene would be like a make believe trick. I ll be your john. Just like in the movies.
Helen was quiet for a moment and then said she d have to think about it. I didn t talk to her for a few days and I feared I d blown it. But one night I received a call from her, only it didn t sound like the Helen I knew. She greeted me very formally by calling me mister, and ignored my attempts to start a regular conversation.
I m sorry, sir, I haven t the time to chat. My agency tells me that you desire an appointment. Would tomorrow be agreeable?
Finally I was able to figure out what was going on. Yes, certainly. We agreed to meet at a fashionable restaurant in TriBeCa. I took it that I was to play the part of some hotshot Wall Street man. She would be my very expensive date.
The next evening I got out my most conservative pinstripe suit, put on suspenders, and splashed on some Drakkar Noir. As I rode the subway downtown I was practically trembling with nervousness. I had been intimate with this woman dozens of times, but tonight it would be like the first time, for we would be playing out a dark part of our sexuality.
I was a little early and took my seat at our table. When I saw Helen sashaying into the restaurant my heart skipped a beat. She looked like a different person. Helen is a beautiful woman, a blue eyed blonde, very petite, but with a country girl quality that looks out of place in an urban setting. But now she looked like a sophisticated city slicker. Her tawny hair was swept up on top of her head and her high heels made her almost as tall as me as she approached the table. She usually wears no makeup, but tonight she was sporting quite a bit, and she looked smashing with her dark red lipstick and fingernails polished to match.
She was wearing a sleek black dress slit up the sides, revealing a good deal of her slender legs, which were now encased in the finest stockings. The neckline of the dress was cut quite deep, and when she leaned forward it was easy to see her fancy lace bra.
She took my hand warmly but professionally. After I sat down, she took out a cigarette. I quickly whipped out my lighter and lit it for her. Some women look extremely sexy holding a cigarette Helen is one of these women. We ate an excellent Italian dinner holding a polite conversation. We pretended we had never met before. We talked about art, theater, a little politics, but nothing intimate.
After dinner we took a cab to her apartment. During the ride her hand surreptitiously crept into my lap and drew soft circles over the fabric on the insides of my thighs. My cock was as stiff as a board and very apparent. She looked in my eyes and licked her lips. My, my, do I excite you? Her thigh was exposed due to her dress riding high, so I slipped my hand over to caress it. She caught me and slowly pushed my hand away. Not now, she whispered.
Once in Helen s apartment she turned on a lamp with a soft light bulb, undid her hair and shook it out. She then turned to me, her lips moist and pouting, and said, There is now the matter of the fee.
I pulled out my wallet. How much do I owe you?
Two hundred dollars for an hour, one thousand for the entire evening.
I opened my wallet and pulled out ten one hundred dollar bills of Monopoly money. Helen nearly burst out laughing but quickly checked the impulse. Instead she took the money and spirited it away. Very good, sir. Would you like a drink?
We had a few snifters of brandy as she continued to tease me. She kicked off her shoes and ran her foot up and down my leg as we sat next to each other on the sofa. My wandering hands were not turned away, and after caressing her thighs a bit, they inched upward to her delicate panties. They were quite wet.
Perhaps we should retire to the bedroom, she said softly. We rose and she took me by the hand into her boudoir. Entering it was like seeing it for the first time. She had done a bit of redecorating and it now looked like the inner sanctum of a premiere courtesan. Please undress, she said, her voice quavering. I quickly removed my clothes, but laid them down carefully on a chair. There was plenty of time. She sat on the bed with a cigarette watching me. When I finished she stood and removed her clothing slowly, lingering over each article. I stood observing, my cock sticking straight in front of me, a divining rod that had found its treasure.
Helen turned down the covers and stretched out on the bed, beckoning me. I slipped in beside her and took her in my arms. We kissed, just a peck on the lips at first, then a fiercer, hungrier union of tongues. My hands explored her back and dropped down to her ass, which I squeezed and probed. She stuck her tongue in my ear, something she hadn t done with me before. We drew tighter together, attempting to occupy the same space. She whispered in my ear, Would you like me to suck your big, hard cock?
I nodded and she kissed a trail of lipstick prints down my sternum to my navel, and then in a circle around my dick. She took my balls in her mouth and sucked on them it felt as if she were trying to draw them through a straw. The effect was truly tantalizing. Then she popped my cock into her mouth and fellated me with infinite skill and tenderness. I would be at the brink of orgasm when she would stop and ever so lightly draw her fingernails up the shaft, leaving my whole body quivering like jelly.
Helen used this technique several times until I was mad with lust. I had to fuck her. I pulled myself up and told her so. And since this was a new experience, I was going to fuck her in a way I had never done before. I want your ass, I said devilishly.
Her eyes lit up with excitement. Well, that ll cost you extra, she said, her voice hardening.
I grabbed my wallet from the nightstand, pulled out a phony five hundred dollar bill and tossed it to her. Would this be enough money? I asked.
She put the money away and I laid her down on the bed. She lifted her legs, and I positioned them so they went far over her head, her toes touching the headboard. I sat back on my haunches, soaking in the awesome erotic sight. Her pussy and asshole were pointing straight up, as if they were being served on a platter. I lowered my face into the delicious canap and dined. Her cunt was creaming as it never had before. I rose and slipped my cock into her bubbling pussy. She was so slick that I had my organ lubricated after only a few strokes. I withdrew from her cunt and moved my cock to the doorway of her dark passage.
All right, Mister, fuck my ass! Helen hissed, her fingers busy pulling on her nipples. Slowly, I sank my rigid member into the musky entrance of her upturned bottom. Patiently, I surged forward, concerned that she might not be able to handle my action. Her moans of passion told me I needn t have worried. Yes, God, all the way! Shove your cock all the way up my asshole.
It was done. I was balls deep in her ass, and the sensations were indescribably phenomenal. I sawed my swollen manhood in and out of her with ever increasing speed. Helen exhaled on every thrust, emitting an animalistic grunt. She had completely lost control. She locked her ankles around my neck and hung on for the ride.
Minutes later, I fired off round after round of semen into her bottom. She tightened her legs around me and came with a scream. We collapsed and lay heavily on the bed, our limbs outstretched, our hearts pounding, breathing heavy like winded decathletes.
When we recovered our strength we bathed together and began our lovemaking anew. This time I fucked her sweet pussy. Before the evening was over I would come in every one of her orifices. She would have twice as many orgasms as me.
The evening was a triumph. Helen gave a masterful performance, playing a bewitching seductress who only comes out at night. And I had realized my most tantalizing fantasy.
Mr. Richard O., New York, New York