On Thursday evening, I watched 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 must admit, the part of the movie that gets me hot is Rebecca De Mornay’s Character Lana. I am not talking about her physical beauty; although I 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 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 stranger gets me even hotter. I 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.
I helped him to lie down on his back and then I got on top of him and kissed his lips eagerly. He used his tongue to explore my lips before sticking it inside my mouth. It felt like heaven when I felt his tongue intertwine with my own. I kissed his check and neck, getting my bright red lipstick on his skin. Anthony removed his shirt and tossed it to the floor. I pressed my body on top of his, loving the feeling of flesh on flesh as I felt his body heat. Our kisses were getting really hot and heavy by this point, and I felt his raging hard-on as he pushed his hips up on my legs. I knew that we would soon be fucking.
Anthony took the initiative and pulled down my red lacy panties as he lay under me. He grabbed my bare ass and started to knead it in his hands. I knew my pussy was getting wet on his nice navy slacks; I pulled his slacks down over his legs so he wouldn’t have to have his dry cleaner remove a wet spot the next day. I could feel his erection even more with only his silk white boxers between us now.
Without a word I stood up and took his hand. He stood up and I walked to the bed while still holding his hand. I appreciated his open staring at my nude body as we plopped ourselves down on the bed.
“You like what you see?” I asked him as I lay on my back spread eagled. I always get a special rush when someone admires my naked figure. I spread my legs wide to give him a good view of my bush. Sometimes I shave down there, but now I keep it shortly trimmed. My pubic hair is slightly darker than the blond hair on my head. I jiggled my tits to give him even more to look at. I got my first good view of his cock as I noticed the bulge in his boxers.
“Yes, I love what I see, Jennifer!” he said as he put his hands on my tits to feel me up. I reached into my black leather purse to pull out a condom while he explored my body with his fingers. I wondered if he had ever been with a call girl before. I was intensely curious, but I didn’t think it would be proper to ask. I let myself get lost in my fantasy. I wanted to remember every moment of this so I could masturbate to it and fuck my husband while remembering this night. It felt so dirty to actually be in a stranger’s hotel room, about to fuck him, and have him believe that I was a prostitute. I got so hot when I felt the $300 in my purse. I didn’t really need the money; it was the fact that I was about to earn it for having sex that made me feel super nasty and hot.
I unwrapped the red Trojan lubricated condom. While I had been getting the condom out, Anthony had removed his last item of clothing. He lay on the bed naked right next to me. I felt our bare legs brush up against each other. I slowly put the condom on his huge erection. I thought it would be proper to let him choose the position, since he was paying for this experience.
“How do you want it, Anthony?” I wondered what position he would choose. My bet was missionary, since he seemed pretty conservative.
“I want you on top, Jennifer. I just want to close my eyes and let you make love to me” was his response.
That sounded fine to me! Sometimes I love to take charge sexually and ride a man. I positioned my body on top of his and helped him guide his dick into my waiting pussy. I felt the head of it pop into my hole, and then I gently lowered my body down onto his as his dick sunk further and further into me. I relaxed for a minute after it was all the way inside to give me time to get used to the filled up feeling between my legs. I wrapped my legs around his and gave him a long slow kiss before starting to move my body. I could hear the wet sounds of our kiss as I lay still and enjoyed the feeling. I was very aroused and ready to give him the fucking of his life.
I started to grind my hips up and down slowly. Since Anthony had referred to the act as ‘making love,’ I figured that I should give it to him slow and easy for awhile before I got really wild on him. He didn’t talk, but he made soft sighing and moaning noises as I rode his cock with my slick pussy. I moaned a little myself. I was tempted to let out some loud exaggerated porn star moans, but I wanted this to be believable, and I didn’t want to turn him off with any fake theatrics. All of the quiet moaning and groaning I was doing was completely natural. I felt the first hint of sweat as our bodies got hotter. His chest started to feel slippery as my breasts pushed up against it during sex.
I suddenly felt his hands grab my ass, and he started to play with it again. I keep my ass well toned, and I hoped he liked feeling the firm round contours as he grabbed my ass. I tried to touch him as much as I could, but it was difficult because I was on top and needed some support from my other hand sometimes. He kissed my neck and the area between my breasts as I started to ride him a little harder and faster. I felt his chest bump up against my chest with each thrust. He started to move his hips as well to meet my thrusts. I focused on the wonderful feelings deep inside my pussy as he thrust harder into me from below. I wished that I could fuck him without the condom.
Our kisses became more and more eager as we thrust faster and faster. Anthony slowed down a few times, presumably to keep from coming too soon. I put a finger from my right hand on my clit and played with myself a little; not enough to come, but enough to really add to the sensation between my legs. I felt his cock fuck me really fast and deep all of a sudden, and I put my arms around his back so we could press our bodies closer together. I used every muscle in my body to give him a good time as he got closer to orgasm.
He started to moan louder as we went at it really hot and heavy. I ground me hips rapidly up and down, and rotated my hips around to give him a surprising sensation. I lifted my torso up and said “Play with my tits, Anthony.” He grabbed one breast in each hand and played with them while gently pinching my left nipple. If he looked up, he would have seen my long blonde hair flying around like crazy as sweat poured down my forehead. I yelled “Fuck me!” really loud to turn him on even more as he approached his climax.
He was thrusting his hips up so rapidly I could barely keep up with the pace, and I felt his cock slam deep inside my pussy a few times each second. We were both breathing and panting really hard with sexual exertion as we fucked each other like crazy. I quickly remembered my fantasy again, and I felt like a real call girl pleasing her customer to the best of her ability. I wondered how often real prostitutes felt actual sexual pleasure while working. I knew that to them it was just a job probably, but to me it felt damn good, and I enjoyed the awesome sex as he fucked me as hard as possible.
He let out one really intense moan and then I could tell that he had started to come. I saw his face wrinkle up as he started to come as he fucked me hard. I sat still, letting him control the pace as he let the orgasm course through his body. I felt a sudden rush as the first burst of come rushed out of him. Even with the condom on I could feel the heat of his come in my pussy walls. I gently played with his balls to intensify his orgasm. He thrust really fast for a few moments and then the pace started to settle down as his cock had some more contractions. I let him fuck me slower and slower as he finished his orgasm, and then I collapsed on top of him. When I felt his cock gently pull out of mine I discretely pulled off his condom and tossed it onto a towel on the floor.
I rolled off of him and caressed his body as we lay side by side. His cock was still big while semi erect, and I stroked his thighs to make him feel even more pleasure after his intense orgasm. Some residual come was still dripping out of the head of his cock.
We talked for a few minutes after sex. Normally I like talking to men after a one night stand, but I didn’t think a real call girl would stick around for too long after performing the service. I didn’t want to be rude, though, so I listened as he chatted about the Chicago Cubs and Bulls, and about a great Japanese restaurant on Clark Street. I smiled and stared at his naked body as he chatted, and I was glad that he didn’t ask me any personal questions. I didn’t want to lie if he asked me questions about my life, but I hadn’t prepared much of a background story to explain my situation either. All he knew about me so far was that I supposedly lived somewhere in the city.
He did ask me if I had a card, which I assumed was so he could call me for another ‘date’ or whatever you call the time between a call girl and her customer. I cursed myself as I realized I hadn’t planned for this question in my fantasy.
“Uh…I don’t have my card on me.”
“That’s all right, how about your phone number?”
“Well, I don’t usually give it out,” I lied.
“Then how do you get repeat business?” he asked.
I hesitated. I didn’t know what to say.
“People know me through word of mouth. People usually have my number through referrals.”
“Oh.” He said. I knew that I had hurt his feelings because he must have believed that many other people have my number but he didn’t.
“Uh…Anthony, I’ll give you my number, I had a really good time with you. Call me up sometime!” I answered, not sure what I would do if and when he did call me. “But please don’t give my number out to anyone, O.K.? I really don’t need any more business.”
“Your number is safe with me, Jennifer.” he answered.
“Well, it was fun partying with you, Anthony. I had a really good time, and by the grin on your face I can tell that you had a good time too!” I looked at him as he started to get dressed. Still naked, I walked over to the nightstand to get a pen and piece of paper out of my purse. I didn’t have a nice pen, just an old Bic ballpoint that could barely write. I scribbled down my phone number and name on the scratch paper and handed it to Anthony. He took one last good look at my nude body before I slipped back into my lingerie.
He surprised me as I finished hooking the bra back on. He was right behind me, and he started to rub my shoulders. This felt really good after the sexual exertion, and I melted in his touch as he gave me a short backrub. I closed my eyes and let him caress my back and shoulders. After this blissful massage, I turned around and gave him a long wet kiss. He looked very hot in just his pants and no shirt. The skin of his chest touched my flesh one last time as I let him kiss me passionately.
I eventually put on the rest of my clothing and said my final goodbye of the night to Anthony. I wasn’t sure if this would be the last time I ever visited him, or the start of an affair. I didn’t want him to know that I was just a bored housewife looking to fulfill a nasty sexual fantasy.
“How are you getting home, Jennifer?” he asked me on my way out the door.
“Oh, I call someone to pick me up. You know, my manager.”
“Oh.” He replied, realizing that I meant a pimp when I said manager. He handed me another crisp hundred dollar bill as I walked out the door. I slipped into my role playing again, feeling like a real call girl as I took my tip and put it in my pusrse with the rest of my earnings. I closed the door of the hotel suite behind me and took the elevator back to the lobby.
On the way down to the elevator to meet my husband, I reflected on the evening’s events. I was feeling mixed emotions about the experience. I did not regret it at all; it was hot to pretend I was a paid sexual escort; and I had just fucked a stranger for money. But for some reason I felt that part of the fantasy was not completely fulfilled. The whole experience just felt like a great one night stand with an attractive stranger in a fancy hotel. It didn’t feel dirty enough to really meet my expectations of being a total slut prostitute. I felt it was a good introduction to the world of prostitution, but I realized I needed a little something more to feel like my fantasy had been completed. I felt that I had lived like a high class call girl, but I wanted to live like a whore.
I arrived exited the elevator and walked to the hotel bar. Jim was pretty drunk as I sat down next to him at his table.
“Hey there big guy! Want to party?” I joked, pretending that I was still a call girl with my own husband.
“How much is it?” he joked back.
“$300.” I answered.
“$300? I don’t have that kind of money on me. Can I write you a check?”
“A check? Do you think I’d take a check from you?” I laughed, replaying a conversation between Tom Cruise and Rebecca De Mornay in Risky Business.
“Seriously, honey, how was your date with Mr. Businessman?” he asked after taking a big sip of his gin and tonic.
“His name was Anthony, and I fucked his brains out. Here, take this.” I said as I pulled one of the hundred dollar bills out of my purse and folded it in half.
“What? Why are you giving me money?” Jim asked.
“Because you’re the house!” I laughed. I told him all the details about my first experience as a prostitute, and he quietly listened. I didn’t spare him any detail; I was graphic in my physical description of Anthony’s cock, and I described how good it had felt when I straddled Anthony and covered his cock with my juicy cunt. I reached under the table and felt my husband’s growing erection as he listened to me describe what had happened upstairs.
“Wow, that’s smoking hot, Jennifer. Was it everything you imagined it would be?”
“Well, yes and no. I’m very glad I did this, Jim, it was wicked fun. But deep down inside, I think I need to do something much kinkier. I want to feel more like a street hooker to complete the fantasy. This felt too nice and clean; I didn’t feel like a total sluttish whore. I guess what I’m trying to say is that I want to do this again, but not in a fancy hotel. I want something really sleazy, Jim.” Jim and I are very open sexually, and he wasn’t shocked to hear me say this. “Let’s go home, Jim. I want to make love to you.”
“I booked a room while you were upstairs, Jennifer.” Jim said. I was very relieved, as I felt too tired to make the trip back to the suburbs. Jim paid his tab at the bar and we walked to the elevator. When the elevator door opened I noticed Anthony getting out of the elevator. The moment was awkward; neither of us said a word. I wondered if he thought that I was with another customer so soon after our encounter. This thought turned me on all over again, and I gave Anthony a wink as I entered the elevator.
Jim had booked us a nice room on the fifth floor. It wasn’t as luxurious as Anthony’s suite, but it was still incredible. I collapsed on the bed, too exhausted to take the initiative sexually. I let Jim pull up my dress above my waist and remove my thong. He rubbed my pussy to get me warmed up.
He stripped all of his clothing off and got on top of me as I lay on my back. I still had the dress partly on as he slipped inside my warm hole. He asked me to describe my fantasy while we fucked.
“Well, I would dress in a really skimpy outfit, of course. Something cheap and trashy, not at all like this expensive dress. Something that a real whore would wear.” I loved to talk dirty while we had sex.
“Yeah, you’re going to be a street whore next time, Jennifer?” my husband said as he pumped away. He was talking between pants and groan. I felt sweat drip down from his chest to my dress. My dress was getting soaked. It felt really naughty to fuck with my dress still on, like we were too horny to remove it all the way and just had to go at it before I could strip it off.
“Yes, I’m talking about cheap sex at a motel 6, Jim. Or giving some stranger a blowjob in an ally! Really down and dirty, honey.”
“You want to suck off some guy you just met, my whore?” Jim banged away harder and harder. My pussy felt really used. It had just been fucked by Anthony less than an hour before, and now my husband was roughly pounding my pussy with his cock. He wrapped his hands around my ass so he could thrust deeper. I nudged him a little to move his waist up just a few inches so I could finger my own clit. I started to masturbate while he continued to slide his dick in and out of me faster and faster.
I pictured myself standing on the street corner in a black mini skirt and a super tight red tank top. I imagined having no bra or panties underneath my clothes. I fantasized about a guy driving up to me and rolling down his window. “How much?” the guy asks in my fantasy. “$50 for a blowjob, $100 for a fuck!” I answer in my fantasy.
I could tell that Jim was getting close to coming. I couldn’t help comparing his sexual technique to Anthony’s. It was hard to compare, since I had been on top with Anthony and now I was on the bottom with my husband. My husband grabbed me tighter than Anthony had. It felt really slutty having sex with two men in such quick succession. I heard my husband let out a final moan before filling my pussy with his hot come. With no condom between me and my husband I felt his hot come rush into my pussy as he came.
After Jim finished coming, he stayed inside me for a minute, still semi erect. Eventually he withdrew his cock and lay down beside me. I continued to rub my clit, feeling my husbands sticky come on my fingers as I masturbated. His come was oozing out of my pussy and onto my hands.
“Did you like that fucking, Jennifer?” He asked.
“Oh yes. You were a great customer. I hope to service you again sometime!” I laughed.
“How did you like being a paid call girl, honey?”
“I liked it a lot. I just can’t wait to plan my next adventure. I hope you can help me plan something really sleazy for next time.” I stroked my clit faster, rubbing in furious circles, using firmer pressure.
“O.K., Jennifer. Tomorrow we will go shopping on Clark Street. There are a bunch of grungy clothes shops; I’m sure I can help you pick out something really slutty for tomorrow night.”
“Tomorrow, Jim? I was thinking more like next weekend.”
“Hey, I’m your manager, and you will do what I tell you to, whore! Just kidding, I’m trying to help you with a little role-playing to set the stage for your next paid sexual escapade, honey! Seriously, it doesn’t have to really be tomorrow. I must confess, I thought this would just be a fantasy for your enjoyment, but I got so turned on while I was down in the bar having some drinks. My dick was hard the whole time as I tried to picture you and your customer in his hotel room. God you turn me on, Jennifer!”
I continued to finger myself, spreading my legs apart so I could reach stick a finger inside my pussy. I closed my eyes. I imagined wearing something really trashy the next night. I pictured myself in a seedy motel, sucking off some stranger I had just picked up while standing on a street corner. The guy in my fantasy was a factory worker who had saved up his money for a month so he could party with a dirty slut for an hour. I prepared to be that dirty slut, catering to the customer’s every whim as he fucked me until his come was spent, and he received the fuck of his life.
I reached the point of no return, feeling the crashing waves of my orgasm hit my body. It started out with hard physical contractions inside my pussy, and then my whole body felt an incredible release of tension. I let out a load moan as I came hard. The aftershocks kept my pussy quivering for a minute after the initial waves of my orgasm subsided.
“Oh my God that felt good, Jim. I feel so utterly exhausted and sexually spent. I can’t wait to tell you all the juicy details of future sexual adventures. I love you, Jim.” I turned around to kiss him goodnight.
“I love you too Jennifer. Goodnight.”
I drifted off to sleep, with thoughts of hot adventures and cheap sex to come.