Jack's Adventures


In my head, I had these visions of stunning women with fantastic bodies doing all sorts of naughty things with me, but in real life, I had only a moderately good looking woman who wouldn’t even fuck me with the lights on. When the money finally started rolling in, I realized this was my chance to live out all my fantasies. Because, I soon came to realize, everybody has a price, and some people will do absolutely anything to make money. So I kicked my girlfriend out of the house and proceeded to begin my adventure. Chapter 1 I thought my first taste of what was to come was going to be courtesy of an extremely high priced prostitute named Sascha. As I said, I had very poor social skills at the time, and could not imagine ever approaching a woman as beautiful as she. But somehow, her job made her more human; knowing that she fucked for money gave her a sort of flaw, something that allowed me to look into her eyes without fear. Anyway, I wasn’t asking for anything outrageous, I just wanted to see what sex could be like with a little imagination. So I looked on the Internet (you’d be amazed what you can find there), on a website devoted to reviewing escorts. Sascha caught my eye, as she had never received less than 8 stars (out of 10). Her picture was beautiful. She had a dusky complexion, with intense green eyes, and full pouting lips that looked made to be wrapped around a nice cock. I kept browsing through her profile, and found her contact number. I figured what the hell, the worst she could say would be no. So I called her up. I was so nervous, and so excited at the same time.

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   I thought I might throw up and cum in my pants all at once. My dick was rock hard and throbbing when someone picked up the phone. “Hello?” said the sexiest, smokiest voice I had ever heard. The mere sound of her voice almost caused me to blow my load. “Is this Sascha?” I asked, my voice trembling. Not too much, I hoped. “Yes, who’s this?” she asked. “Uh, hi, my name is Jack. ” I said. “I was hoping to book a date with you. ” I had learned the proper terminology from the F. A. Q. on the website. “How long would you like my company?” she asked“All night.

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  ” I told her. Might as well get my moneys worth. “Well, Jack, I’m booked up tonight. Would tomorrow be alright?”“That would be fine” I responded. “How about dinner and a date, beginning at 6:00?”“That sounds just lovely. Since you’re a new client, I’m afraid we will have to meet in public first while we get to know each other, and any other activities after dinner will have to be in a hotel, not your house. And cash only for the first time. For all night it will be $3,000. ” she instructed. “No problem at all” I said. “Meet me at Le Cirque. ” That was the best restaurant in town. “Oooh, fancy. I’ll be sure to wear my best outfit. See you then, Jack.

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   Bye bye for now. ”“Bye” I told her, and hung up. I couldn’t believe it. I was going to have sex with a woman tomorrow night, and what looked to be a beautiful one at that. My cock was straining at the confines of my underwear, fully erect and excited just by her voice. I knew tonight would be almost sleepless in anticipation, so I decided to take a sleeping pill, jerk off, shower and go to bed. I don’t know a better way to be relaxed and go to sleep. I left my computer room, and went into my bedroom, where I stripped off my clothes and put them away. I then went into my T. V. room, where, in a special rack, I kept my porno DVD’s. I selected one that always excited me, and popped it in. I pulled a towel out the room’s closet, where I kept them just for this purpose, and laid it down on the couch. Grabbing a nearby bottle of lotion, I pressed play and sat back to ease some tension. My cock was so hard it hurt.

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   Pre-cum was almost pouring out of the tip, and I knew it wouldn’t take long before I shot off. On-screen, a buxom blonde was kneeling in front of a well-built stud, and swallowing his cock. One of her hands was playing with her pussy, and the other was fondling the guy’s balls, lightly tickling them. I don’t know how the guy kept from cumming, as his sizeable cock was all the way down her throat. Some people just have extraordinary control, I guess. I squeezed some lotion onto my hand, and wrapped it around my cock, slowly moving my hand up and down. Now, I don’t claim to have a huge dick. Its only about 6 inches long, and maybe 2 or 3 around. But it always seemed like a fine size to me. But as soon as I touched my dick, it jumped, like a bolt of electricity had passed through it, and I swear it grew another inch. When the lotion had had a little time to soak in, I started moving my hand faster and faster, squeezing a little. I began to stroke my nuts with my free hand, lightly rubbing them. I could see the guy on the screen was getting to the point where he couldn’t control himself for much longer, and he grabbed the blonde by the sides of the head and started fucking her face, really shoving his cock down her throat, then bringing it almost all the way out before plunging in again. Through my superb speaker system, which hooked into the T. V. 

  , I could hear the wet sloppiness of her throat being violated, her moans and his groans, all overlayed by the sound my lotion-slick hand rapidly stroking my cock, and my breathing quickening as I began to moan myself. In the movie, the guy pulled his cock out from her throat and started spewing jets of thick, creamy cum all over her face and into her open mouth. I couldn’t hold back any longer myself, and my semen started shooting into the air, falling back down onto my stomach and chest. On screen, the guy was still going, albeit less forcefully, really soaking the blonde. Cum dripped from her mouth and face, falling onto her oversized tits and rolling down them. Little droplets of sperm started coalescing at her nipples and dripping slowly off them, like a faucet that has been barely turned on. What a great sight it was. Some women are just born to be sluts and whores, and those girls looked their best when sucking on dick, or getting fucked hard. This blonde looked her absolute best when covered in cum, I thought. When my breathing slowed down to something approaching normal, I turned off the movie, and stood up. I quickly grabbed the towel and mopped off my chest and stomach, then headed for the bathroom. I dropped the towel into the clothes hamper, which was a chute that led to the basement, where a basket was waiting for any laundry that fell. I had the house custom-built as soon as the money started coming in, and the bathroom was one of the best features of a very impressive home. As big as most peoples bedrooms, in the center was a bathtub big enough in which four people could be totally comfortable, and it doubled as a whirlpool. In the corner was a shower the size of a king bed.

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   In the shower were five shower heads, all pointing to the center, and fastened to one side was a padded bench should I get tired of standing in the shower. I turned the spray on and stepped in, luxuriating in the hot water spraying over me. I sat on the bench for a while, feeling the steam roll over me, soothing and calming me. When I began to feel drowsy, I quickly cleaned up, and got out. I dried myself off, brushed my teeth, and padded into the bedroom, where I lay down in my king-sized bed, and went right to sleep. Chapter 2I awoke the next morning, refreshed and eager. I rolled out of bed, and threw on my robe and slippers, and shuffled downstairs. Along the way, I stopped to greet Damien, my German Shepherd. While I’m asleep at night, he roams the house, keeping everything safe and secure. I know if I were to come face to face with him after breaking into the house, I would run as far and as fast as I could. Weighing in at about 100 lbs. , he is the sweetest dog in the world, unless you don’t belong in the house; then he’s as mean and vicious as a cornered lion. Best home security system in the world. After getting to the kitchen, I started a pot of coffee brewing, and then made a call to an ultra-exclusive men’s store in the area. I made an appointment to get a new suit, shirt, and everything else.

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   After all, I had to look good for my big night tonight. After coffee and cereal, I got dressed and headed out. I love shopping in this store, it’s by appointment only, so there are no crowds to bother me. I hate large groups of people. A great thing about being ridiculously wealthy was being able to indulge your quirks. As my Jaguar sped through the streets, I let my mind drift, imagining tonight. Thinking about talking with Sascha, eating with her, seeing her naked body, having her on her knees, sucking my dick while I fucked her face and spewed my cum all over her body. Ooohhh, the images were delicious. When I arrived at the store, I parked in front and went in. When I walked through the door, one of those electronic sensors chimed, announcing my presence. Out from the back came a striking redhead, somebody I had never met before. I’m sort of a regular there, and I thought I knew everybody. “Um, hello” I said. “Is Jason here?” Jason was my regular assistant, and I had been expecting him when I made the appointment. “No” responded the lady.

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   “Jason quit a couple of days ago. Something about wanting to make it in showbiz, I think he said. I’m going to be taking over for Jason, and assuming all his clients. Are you one of his?” “Yes, I am. My name is Jack O’Connor. ” Every salesperson in the store was responsible for a certain number of clients, and the customers dealt only with that salesperson, thus establishing a good personal relationship. It was rather nice, as Jason had grown to know my likes and dislikes and made some excellent recommendations. As soon as I told her my name, her eyes got a little wide, and she inhaled a little sharply. I knew why. I didn’t buy many clothes, but what I lacked in quantity was made up for in quality. I only bought the best of everything, and it was almost all custom-made just for me. I didn’t keep an exact count, but I bet I had spent at least $20,000 there last year alone. “Well,” she said. “My name is Valerie, and I would love to help you. ”I cast an appraising eye over her.

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   Dressed in a short, but not quite mini, skirt, and a silk blouse, she was definitely a looker. Her firm tits were well accented by the clingy silk, and her tight ass looked delightful in the almost-immodest skirt. Her legs seemed to go all the way to her neck, and I’m sure they looked great in or out of the high heels she wore. Idly wondering if she was a natural redhead, I decided I might like shopping here even better now. “Valerie, I would be delighted to have you assist me. ” I told her, and smiled shyly, praying I wouldn’t get tongue tied. “I need a new outfit for a date tonight, and maybe you can help me decide what looks good. ”“I can certainly help with that. ” She said, smiling back, a bright smile that lit up the room. She turned to go over to the clothes racks, and as she did, I noticed her lick her lips a little, and smile in a totally different way. Not the smile of a salesperson, but that of a hunter who has caught the scent of prey. As she walked away, I couldn’t help but stare at her ass, shifting and wiggling in her skirt. So transfixed was I, that I neglected to follow her. She stopped suddenly, and turned towards me. My face turned bright red in an instant, and I started to sputter an apology.

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  “No apology necessary. It’s quite alright. ” She said, smiling that hunters smile again. “Now, if you’ll actually follow me this time…”And with that, she turned around again, and started walking. I followed this time, but was still amazed at her butt, which was wiggling even more this time, if that was possible. My head was flooded with nasty thoughts, now featuring Valerie instead of Sascha. But having little experience, I didn’t know if I had interpreted her smile correctly, and if she always walked this way, or was just trying to make a sale. I kept my mouth shut, for fear of embarrassing myself even further. “Now, then. ” She began, “You said you had a date with your girlfriend tonight?”“N-no,” I stammered, “She’s just a friend. I don’t have a girlfriend”“Oh, that’s too bad,” she said, not looking upset at all. She started pulling clothes off the rack, and handing them to me. I picked out some things I liked, and she took me back to the fitting room, which is really two rooms in one. There is the fitting room, and inside that is another little room, the changing room. I stepped inside the changing room and stripped completely.


   I tried on the new boxers first, but they were way too tight, so I handed them to her over the door, and she said she would go get a larger pair. “While I’m gone, try on the suit, and see if you like that. ” She said. I did, and it felt heavenly. It was made out of pure silk, and since I hadn’t put on my underwear, it soon gave me quite an erection from rubbing over my penis. I was reveling in the sensation when Valerie knocked on the door. “Come on out and let me see if the suit fits. ” She told me. “Uh, h-hold on just a minute. ” I stammered, intending to put on my boxers and then come out. “If you want us to have the tailoring done in time, we need to hurry. So come on out and let me see if it fits you. We have other things to look at too, remember. ” She reminded me. “Alright, I’m coming.

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  ” I gave in. My face flushed absolutely beet-red, I couldn’t meet her eyes as I stepped out of the changing room into the fitting room. I couldn’t meet her eyes, I was so flustered. Of course, walking around in the pants had excited me even more, and my dick felt like it was about to burst. She didn’t notice right off, I guess because the suit coat concealed my raging hard-on. I stepped up onto a little stool, facing a wall of mirrors. The suit actually fit quite well, but I barely noticed. Valerie started checking the fit of the shoulders, and around the chest. For a few brief seconds, I thought my excitement might go unnoticed, as I was sure the horrendous embarrassment would shrink my dick very soon. Then she knelt behind me and started feeling the fit around my butt, paying far more attention than Jason ever did. That settled that. I thought my cock was never going to die down. Then she reached around front, checking around the thighs and crotch. She passed her hand over my straining penis, and stopped there. My face burned, and I closed my eyes, waiting for the shouts of outrage.

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   I mean, no matter how cute she thought I was, this would still be insulting to her right?“Well” she said. “That certainly throws off the fit of the suit. We can’t have that. ”“I’m so sorry. ” I muttered, wishing I was dead right about then. “Nothing to be sorry about. ” Then I turned and looked down at her. She was staring up at me, smiling slightly. Looking straight into my eyes, she asked “Would you like me to take care of your problem for you?”Stunned, I couldn’t believe it. I muttered a barely audible “Yes”, and she stood up and went to lock the fitting room door, assuring us of total privacy. Then she walked back over to where I was. I hadn’t moved a muscle, for fear that I was dreaming, and would wake up. She stopped in front of me, and motioned me to step down off the fitting stool. I did, and she proceeded to unbutton my pants and pull them down, all the while staring into my eyes. When my pants were down around my ankles, she knelt in front of me, and, still staring up into my eyes, engulfed my cock with her mouth.

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   This was my first blowjob, and I never imagined anything could feel so good. “Oh, my God. ” I moaned, barely able to speak. It was an incredible sight. This fine looking redhead kneeling in front of me, staring up into my eyes, with my dick half into her mouth. I was in Heaven. Then she winked up at me, slowly and sexily. She then proceeded to try and suck my soul out through my dick. Wrapping her hands around me and grabbing my ass, she pulled my dick further and further down into her throat. When her nose was buried in my pubic hair, she moved one hand to my ballsack, and started fondling me. At the same time, she started doing something incredible with her throat muscles, almost like she was swallowing, but not quite. It’s very hard to describe, but the feeling was amazing. So far, the only reason I hadn’t cum yet was my jerk-off session the night before, but I knew that wasn’t going to help much longer. Soon, she pulled my dick out from her throat, and started bobbing her head, almost wrapping her tongue around my dick on each upstroke. Before she went back down, she would pause, and flick her tongue around the head of my penis.

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   Then she would dive back down, her tongue scraping along the underside of my cock. Shivers were running up and down my spine, and I was barely containing myself, the urge to cum almost making me pass out. Soon, she started using her hand in addition to her mouth. She wrapped her hand around the shaft of dick, and her lips around the head, and started going up and down, sucking my dick and jacking me off all at once. About 18 seconds later, I lost it. “I’m going to cum. ” I half moaned, half growled. Staring up into my eyes once again, she pulled her mouth back until only the head of my cock was in her mouth, and smiled a quick, eager smile that vanished almost as fast as it appeared. I threw my head back, moaning, as I felt the cum rush from my balls up through my penis and explode into her mouth. Holding onto my dick with one hand, she kept it steady as it tried to leap around in her mouth. I could see her throat working, swallowing my hot load. She was very talented, as all but a single drop, which I think she did on purpose, went down her throat. The one little drop she allowed to escape trickled out of the corner of her mouth, and ran down her chin, where most of it dripped off onto the floor. The rest left a barely visible trail from her mouth to her chin, which she didn’t bother to wipe off. Instead, she stood and adjusted her skirt. 

   “There now. I think the tailor will be able to fit it much better now. ” She said, smiling a satisfied little smile. “If you’ll wait here, I’ll call him in. ”And with that, she walked out. In a few minutes, the tailor walked in, and proceeded to make the necessary marks. When I told him I needed it in 5 hours, he didn’t say anything, but he did add a couple of zeros to the bill. I walked out into the main store area, where I saw Valerie waiting at a cash register. She handed me the bill, and I didn’t even look at it. I was too preoccupied with her face, smiling a little still, and that almost invisible cum trail at her mouth. I handed her my Amex, which se swiped through the little machine. All the time, she never said a word to me, and I was afraid that she was somehow angry with me now, or something like that. I signed the credit slip and handed it back to her. Instead of just tearing off my copy, she wrote something on the back of it, and then handed it to me. Imagine my relief when I looked at it, and it was a phone number.

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   I looked back up at her, and she was smiling her little smile again. “In case your date doesn’t work out tonight, give me a call. ” She whispered to me. I smiled back at her, and turned to leave. As I was walking out, I looked back. She was still staring at me, and when I looked at her, she slowly stuck her tongue out and licked at the cum trail still on her face. Then she laughed a little, and turned to go into the back room. I turned, and walked out of the store. I knew, regardless of how well my time with Sascha went, I would certainly be calling Valerie up. Maybe even introduce the two of them, if Sascha and I got along. This is my first story. What do you guys think? Should I keep going with it? Any constructive criticism would be very much appreciated. .