First Time Prostitute

One Thursday evening, I was watching the movie "Risky Business" with my husband Jim. That is one of my favorite movies. Of course I love the scene with a young Tom Cruise dancing around in his underwear; what heterosexual woman doesn't? But I have to admit, the part of the movie that really gets me hot is Rebecca De Mornay's Character Lana. I am not talking about her physical beauty; although I do appreciate that. I am talking about her character; a high class call girl. Something about that concept gets me all wet and horny. The thought of having sex with a complete stranger turns me on fiercely.

I have had my share of one night stands; but the fantasy about being a call girl sounds much hotter than just having a one night stand with a man I just met at a bar. The thought of getting paid for it is what makes the fantasy so hot. I would never even consider doing that as a career; I just wanted to try doing it once or twice. Something about the idea of money changing hands gets me so hot; the fact that I would have to do a great job of pleasing a complete stranger gets me even hotter. I would want the man to get his money's worth out of me!

"Jim, that is so hot!" I said to my husband as we watched the DVD. I was sitting on the love seat, and my husband was on the big black leather sofa.

"What is so hot, Jennifer?"

"Rebecca De Mornay!"

"Yes, she is rather attractive." Jim replied. He appreciated her classic blonde beauty.

"No, not that. She is a high class call girl!"

"Um...yes, I suppose her character is a high class call girl. She certainly isn't your average looking street hooker!"

"I could do that!"

"Do what?"

"Be a call girl."

"What the hell are you talking about, Jennifer?" He answered. We have an open marriage, so he wasn't as shocked as most husbands would be to hear their wives say they wanted to be a call girl, but he was still a bit surprised.

"Just one time, Jim. You could help me plan it out. Hey, you could be Guido, the pimp!"

"You can't be serious, Jennifer."

"Jim, when it comes to sexual fantasies, have you ever known me to joke around?"

"Well...no. Wow! You have a fantasy about being a call girl? How long have you fantasized about this, Jennifer?"

"For ages, but I never imagined really doing it until just now. That scene at the Drake hotel downtown, where Lana is dressed to kill, and picking up men at the hotel bar got me really hot this time. Something clicked in my head, Jim, and I thought to myself, 'why not?'"

"Wow. When do you want to do this? It would take a lot of thinking and planning."

"Tomorrow sounds nice!"

"Tomorrow! That is very soon. How can we plan this by tomorrow?"

"You are thinking too much, Jim. It can be spontaneous, you know. How hard can it be? You drive me down to the Drake hotel. I am dressed in a slutty yet expensive dress. You will hang out at the bar pretending having a drink and watch over me. I'll strike up a conversation with a well dressed gentleman, and ask him if he is interested in a night of pleasure. Somehow I will have to convey to him that I am doing it for money, not just because I like him. That will be the hardest part; I am not sure how to approach the subject of money. Maybe you can help me scope out a man who looks like he has dealt with high class call girls before."

"O.K., tell me more!"

"When we agree to a price, I will walk up to his hotel room, and...well, you know."

"Be specific, Jennifer. You will do what, exactly?"

"You really want me to spell it out Jim?" I asked, embarrassed suddenly.

"Yes. In graphic detail."

"O.K., he will pay me the money, and I will give him the fucking of his life! I will make sure he more than gets what he paid for."

"O.K. What if he isn't staying at the hotel?"

"Then I will tell him he has to pay for the cab rides both to where he is staying and then back to the Drake."

I should tell you a little bit about myself. I live in Winnetka, which is a wealthy suburb on north of Chicago on Lake Michigan The suburb to the north of Winnetka is called Glencoe, which happens to be where the movie "Risky Business" takes place. It is about a half an hour north of Chicago. The Drake hotel is just north of the downtown area of Chicago, on Lake Shore Drive.

I am about 5'8" tall, 38 years old, and in good physical shape. I have bigger than average breasts, and long legs that I am very proud of. I have long wavy blonde hair and blue eyes. My husband Jim runs an adult web-site. He is also in very good physical shape. He is 43, 6 feet tall, and has short white hair.

I could barely sleep that night; I was so excited to act out such a sluttish fantasy. The next morning, Jim picked out an outfit for me to wear. It was an expensive short black lacy dress. The hem was far above my knees, and the top was sleeveless. It was very low cut in the front, exposing a lot of cleavage. He decided on a red push up bra for me to wear underneath the dress to help accentuate my tits, and a matching red lacy thong as well. I picked out my highest pair of black high heel shoes. I debated wearing stockings, but I decided that bare legs would look better with the dress.

We spent the rest of the day rehearsing for the pickup scene. He played the customer, and I played the prostitute. I knew the subject of money would come up in the conversation, and we agreed that I should demand $300. I had no idea if this was a good figure or not, but it sounded right. We agreed that I had to make sure that the gentleman understood that I was a paid escort, not a woman looking for fun who happened to be hitting on him. I sat next to Jim at our mini-bar to simulate the scene at the hotel bar. I sat really close to him on the next stool, and struck up a simulated conversation, asking him if he was from Chicago, and trying to find out what kind of business he was in. We agreed that I should make some small talk first before asking if the customer was interested in more.

I hung out the rest of the day with Jim at our house plotting and planning the night's activities. We decided that Jim would be sitting at a table in the bar keeping an eye on me, but not letting the customer know that we knew each other. He suggested that I put on more make-up than I usually wear. He also suggested a good line for me to say to the customer: "Would you care to buy me a drink?" Jim's theory was that this would set the stage for the idea that the customer was going to be paying money for time spent with me.

At about 9:00 P.M., we got into our black Lexus, and we drove to the Drake Hotel downtown. I got really excited once we turned onto Lake Shore Drive from Hollywood Blvd. on the North side of Chicago. At night this road is spectacular; on the left, you have Lake Michigan, and on the right you have huge well lit high-rise luxury condos. As you look straight ahead, you see the towering buildings of downtown Chicago; The Sears tower, The Amoco building, and right in the center of your view is the magnificent John Hancock building. As you approach downtown, right in front of the John Hancock building is a building that used to house the headquarters of Playboy magazine. And right in front of the old Playboy building is a wonderful luxury hotel: The Drake.

We got off at Michigan Avenue and drove into the front driveway. We had the valet take our car into the parking garage, and we walked into the lobby. Jim told me to hang around the lobby for ten minutes so he could go to the bar first. He didn't want my potential customers to see us together.

I sat on a comfortable leather chair and observed the luxurious lobby. There was a huge Oriental rug, an immense chandelier, expensive vases and paintings, old oak paneling, and a big table in the middle of the room with a plant on it. There was quiet classical music being played from hidden speakers, and the whole place screamed "Old Money." It looked like the place hadn't changed since it opened over 80 years ago. I knew that there would be some wealthy single men looking for company.

About ten minutes later, I wandered around until I found the bar. It was a small dimly lit bar, but it was the most fancy watering hole I had ever seen. It was called the Coq D'or, and it had beautiful dark wood tables and chairs, and a dark wood bar with a well dressed bartender. This was not the type of place you would order a pitcher of Coors light in. Jim was sitting at a table in the corner, sipping on a martini. I scoped out the prospects.

There were five men at the bar. Two of them looked like they were together talking, so I ruled them out. The other three looked like they were alone. I had a hard time deciding which one to approach; they were all very well dressed and handsome. I chose the one at the end; not because he seemed like a better prospect, but because the end of the bar offered more privacy.

He was tall with short grayish black hair. He looked like he was in his early fifties. He was wearing a nice navy suit with a striking solid red neck tie. I walked up to the stool next to him, and said "Is this seat taken?"

He turned his head and looked at me. I was pleased to notice that he hesitated in answering because he was staring at my figure.

"Uh...no, no! It is not taken. Go ahead!"

"Thanks! I need to sit down."

"The chair is all yours, ma'am!"

He even got up to move the stool, making it easier for me to seat myself. We had a moment of awkward silence, and then he broke the ice.

"How do you do? My name is Anthony." He offered his hand to me.

"I'm Jennifer." I said with a sexy smile on my face as I shook his hand. I was tempted to give his hand a seductive squeeze, but I decided that was pushing things too quickly.

At this point, the bartender asked me if I needed a drink.

"Hmm...I'm not sure yet, I need a minute to decide." I answered.

Anthony was drinking a small cocktail of some kind.

"What's good here, Anthony?"

"I highly recommend the Executive cocktail."

"What is that?"

"It is their signature drink. It is basically a martini, but they spruce it up a bit. It is poured from a brandy snifter into your glass. They use top shelf liquors, it is quite tasty if you like martinis."

"I do like martinis. But I'm not an executive, are you sure I can have one?"

He laughed at my lame joke. "Hah! Yeah, I'm sure Gary will serve you one if you ask nicely."

"Anthony, would you like to buy me an Executive cocktail?" I asked quietly in my sexiest voice."

"Ah...of course! Gary, an executive cocktail for my friend Jennifer, please!"

"Coming right up, Anthony!" The bartender replied.

"So, Anthony. I take it you are an executive yourself?"

"Well, I guess you could say that, but it sounds rather snobby to call oneself an executive. I am a vice president of a bank in the Loop."

"Vice president! Wow, that sounds huge."

"It's not as exciting as it sounds. When people here the word 'Vice president,' they always imagine that there is just one. Actually, most banks have tons of vice presidents; I'm just one of seven."

"It still sounds pretty powerful! So why are you staying at the Drake when you live in Chicago?"

"Oh, I am actually flying to London tomorrow; I just wanted to stay in the city so I didn't have to drive to O'Hare in the morning from my house."

"Where is your house?"

"I live in Lake Forest."

Lake Forest is perhaps the wealthiest suburb in the Chicago area. It is far north of the city, right on Lake Michigan. It is a couple suburbs north of the village I live in, Winnetka.

"Lake Forest! Wow. I live in the city myself!" I lied. I didn't want him to have any clue that I was a fellow wealthy suburbanite like himself.

We continued to chit-chat for about an hour. Before I had arrived in the hotel, I had imagined that the gentleman I picked up would be a total bore, but he actually had a nice personality and was interesting to talk to. He didn't like to talk about work at all; mostly he talked about his interests; boating, horseback riding, and archery of all things.

I put my hand on his leg and whispered "Anthony, do you want to have some fun tonight?"

He actually blushed and answered "Fun? Uh...sure, fun. That sounds...fun."

For the first time he wasn't confidant.

"Maybe we should go up to your room soon, Anthony." I suggested.

"Sure, sure, let's take the elevator. Uh...this is a stupid question, I'm sure. You are a...I mean..."

"A call girl?"

"Oh God, I didn't mean to insult you. I figured you charged money; I just didn't want to say something stupid."

'It's O.K., Anthony! Yes, I am a call girl. A hooker, if you want to be blunt about the fact."

"O.K."

"Trust me, Anthony, you won't regret this. You will have the most incredible night of passion. I will take you places you have never been before." I squeezed his thigh and bumped my hips against his.

I stood up and took his hand. I let him lead me to the elevators, and I whispered into his ear as we walked side by side.

"Anthony, I hate to be blunt, but maybe we should discuss payment now so we don't have to worry about it later." I whispered, making sure to touch his earlobe with my lips.

He turned his head and said "Sure, how much do you charge, Jennifer?" as we walked down the corridor towards the elevator door.

I whispered again,"$300 upfront. Of course you can feel free to tip me afterwards if you think I did a good job; remember, I have to share my commission with my pimp." I blushed after blurting that out; I didn't mean to say the word pimp. I was getting too wrapped up into the fantasy of being a prostitute, and I doubted if a real hooker would have mentioned having a pimp to her customer. I'm sure the customers realized that most hookers have a manager; but it probably wasn't something often discussed on a 'date' with a hooker.

We reached the elevator doors, and once we were inside the elevator with the doors closed, Anthony pushed the button for the 9th floor. I felt the elevator begin to rise, and he answered my request for payment upfront by opening up a shiny black leather wallet and pulling out three one hundred dollar bills. He neatly folded each one in half and handed them to me. I slipped the money into my purse. Anthony had done his part in this sales transaction between two adults, and I was faced with living up to my end of the deal. He had just spent his money on a service, and I felt a little bit of anxiety. I hoped that I would be able to live up to his expectations. I wondered how many times he had been with an expensive call girl before.

As the elevator ascended, I put my arm around his shoulder and kissed him. I wasn't sure what the protocol was for a hooker about kissing her customers on the lips, but in my head this felt more like a hot first date than an illegal transaction. I quickly realized that I hadn't even considered the fact that this was illegal before turning this fantasy into reality. I wasn't afraid of getting into trouble; on the contrary, the extra thrill of breaking the law made me get even hornier.

I hoped that my attempt to act like a professional call girl was fooling him. In my fantasy, the customer is completely fooled, and has no idea that I am just pretending. I wanted to turn this fantasy into a reality for myself, and I concentrated on playing my role. I had no acting experience beyond a 2 credit course in acting my sophomore year at the University of Illinois.

Anthony squeezed my hand as we arrived at the door of his room. He opened the door with his room key. I was surprised that the key was really a metal key, and not a keycard. The room took my breath away. It was just as luxurious as I had expected it to be.

I sat down on the brown leather chair and slowly removed my heels. I wiggled my bare feet to focus his attention on my legs. I put my hands on my feet and seductively rubbed my way up from my legs to my thighs. I considered how to ask him what he wanted to do. I wanted to sound like a real hooker.

"So what do you want to do, babe?" I asked Anthony in what I hoped was a sluttish voice. Before he could answer, I blurted out "I can suck your cock, or you can just fuck me. Or you can do both if you can recover in less than an hour! Anything beyond that is going to cost you more."

I regretted what I had just offered. I hadn't planned on doing any more than just straight sex, and I didn't know how I would answer if he said "I'll give you double if you let me pee on you!" or something really kinky like that. Fortunately, Anthony appeared to be more of a gentleman than that.

"You look so beautiful, Jennifer. I just want to make love to you. I can't wait to touch your body!"

I was relieved that he seemed to be normal, and not a total pervert. Then I realized that I shouldn't be calling other people perverts for their sexual kinks; after all, I was pretending to be a prostitute, and I was about to fuck a total stranger for money in a hotel room.

"Well you can come over here and touch my body right now, Anthony! This dress isn't going to take itself off, you know!" I said, laughing at my own lame joke.

He calmly walked over to me and kissed my bare shoulder. I melted with his kiss; this was feeling more and more like a hot date to me than a role playing scene. I temporarily forgot that Anthony believed I was a paid professional, and I wrapped my arms around his back, feeling his body against mine. His hug warmed me up, and as he pressed his body even closer to mine, I felt his erection against my stomach. He reached around my back and unzipped my dress slowly. I started to kiss his lips eagerly. He kissed me back, which felt really wonderful. His lips were soft, and he was a great kisser. He didn't put his tongue into my mouth right away; I had to break the ice and do that first. I probed his tongue with my own, and my pussy got really wet as I enjoyed the ecstatic sensations of our first deep kiss.

I felt the straps of my dress start to slide down my arms as Anthony finished unzipping the back of the dress. I let him pull the dress gently down my body and then down my legs. I stood there next to him in my bra and panties, and twirled around to give him a good look at the body he had paid for. I always feel a thrill inside me as I expose my flesh to a new lover for the first time, and this was no exception. I got really turned on knowing that he was looking at my body. I love showing off my body, and I savored the feeling of his stares on my exposed skin. I hoped that he was looking at my red lacy bra and trying to visualize how my tits looked underneath. He would be finding out soon enough!

I kissed him some more, and felt his hands reach around to find the clasp on my bra. He knew what he was doing, and he quickly had the hook undone. I let the bra fall to the floor. I stepped back again, giving him a chance to look at me topless. I am very proud of my 36C breasts, and hoped that he was trying to figure out if they were real or fake. They are all mine, and he would know that soon enough when he felt how soft they were. My nipples hardened as he stared at them. I felt a wonderful nervous rush as I realized I was almost naked. For me, nothing compares to the thrill of being completely naked and having my body looked at.

I decided that Anthony was over dressed, and I loosened his tie and then removed it. His tie felt like pure silk, and it was a darker red than the shade on my panties. I took off his blazer, and started to unbutton his light blue dress shirt, kissing his slightly hairy chest as my fingers worked their way down towards his waist. He gasped when I lightly kissed his nipples one by one. I opened up the shirt, but didn't remove it. I love the way a guy looks with an unbuttoned shirt on. Anthony had a nice chest; no very muscular, but not overweight at all either. I caressed his shoulders while I kissed his chest. I helped ease him into the comfortable white sofa across from the king size bed.