("`-''-/").___..--''"`-._ `6_ 6 ) `-. ( ).`-.__.`) (_Y_.)' ._ ) `._ `. ``-..-' _..`--'_..-_/ /--'_.' ,' (((' (((-((('' (((( K R I S T E N' S C O L L E C T I O N _________________________________________ WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are under age, PLEASE DELETE THIS FILE NOW!!!! _________________________________________ Scroll down to view text ------------------------------------------------------- This work is copyrighted to the author © 2015. Please do not remove the author information nor make any changes to this story. All rights reserved. Thank you for your consideration. ------------------------------------------------------- My Wager with Vanessa by Harry Ogre (oagre7@hotmail.com) *** An older guy wagers his gorgeous sugar baby that she can't get a certain handsome stud to fuck her three times. The results are quite interesting. (MF, mast, oral, voy, cuck, huml) *** Part One I'm a guy in his 50's. I'm still in reasonably good shape and like to have sex once or twice a week. Since I'm a bachelor and live in a fairly tolerant city, I have been seeing escorts for the last few years. And that's where I met Vanessa. Vanessa works at one of the city's most upscale escort agencies. She's in her mid-30's and still has a tight body with a delicious ass and firm little tits topped with eraser nipples. She models professionally in fashion shows once in a while and still draws stares and appreciative smiles from any guy lucky enough to catch the runway display. She's about 5'9" with legs for days, sultry good looks and thick dark hair that falls to her shoulders. She also has expensive tastes and that's where I come in, I guess. She and I hit it off from the first time I booked her. Her photos on the escort website were mouth-watering. I expected to be disappointed when I saw her in person. But in fact, she looked even hotter than her gallery. Couple that with a charming laugh and one of the most flirtatious smiles I had ever seen and I was smitten big time. Even better, she seemed to like me back. We found it easy to make each other chuckle. Shared many of the same opinions. And we seemed to be made for each other in the bedroom. After I saw her a couple of times through the agency, she wrote out her cell number and email address on a slip of paper and told me that she would like to see me outside the business. Of course, there was a catch. She made it clear that if I wanted to take her out on the town, I would have to cover the bills and our destinations would be only the city's priciest and toniest clubs, bars and restaurants. "After all," she purred, "quality costs money and I'm a lot better than any of those other girls." And she was clear that I would still pay her regular charge every time I wanted to see her undressed or have sex with her. "Does this mean that you'll be giving up sleeping with all those other clients?" I naively asked. "Don't be silly." she giggled. "You don't have enough money to afford me full time. And besides, I'm too much of a slut to stay with one guy. Unless he was very, very rich and a total stud, that is." I guess a prouder man would have turned down her offer. But I was hooked. Deep down, I believed that I could make her care for me so much that she would quit the escort business and end up in a relationship with me. And to tell the truth, a part of me actually dug the fact that she was so sexual and such a firebrand in the bedroom. It was difficult to ignore what she did for a living. She often discussed her services explicitly over the phone with her regular clients. She once explained in exquisite detail how she was going to suck one rich doctor's cock and swallow every drop of his semen – for an extra hundred bucks of course. When she ended the call, she smiled over at me and told me I was going to have to cancel our luncheon date and drive her right over to her client's apartment. "But I made reservations at the restaurant two days ago!" I objected. "Well, I'm going to make four hundred dollars sucking this guy's cock and swallowing his load," she replied. "Those reservations are going to have to wait. But I'll make it up to you. You know how you usually have to pay twenty dollars for me to flash you? This time, I'll let you watch me change and get ready to see my client and I won't charge you a cent." I hesitated for a few seconds, then accepted the inevitable. Four hundred bucks was four hundred bucks after all. "Okay," I shrugged. "It's a deal." "Good." she smiled. "But no touching. You just get to look this time. Otherwise, I'll have to charge you." I winced and she laughed a little. "Start running my bath, honey. Then I'll let you see me in it getting all wet and soapy." Vanessa was as good as her word. She slipped out of her jeans and top and shed her bra and thong and stepped into the bath I had run her. Then we selected a new set of scanty lace underwear for her and I watched as she put on a dress and heels and did her face and hair. It took us about twenty minutes to drive to her client's house. She kissed me briefly on the cheek and opened the car door. "I'll be back in an hour or so." she said. "See you then." Funny thing, as I watched her walk in her expensive heels into the doctor's hi rise lobby and imagined what they were about to do together, I had a raging boner in my pants. I parked in a side street a few blocks away and fought down the urge to take out my dick and get myself off. I turned the radio on and off a few times and went over some work assignments I needed to do. After almost an hour, I drove back around to the doctor's condo. A minute or so later, Vanessa walked out of the lobby and got into my car. She had a Cheshire Cat smile on her face and ruffled four bills in my face. "See what your bad little girl just got paid?" she asked. "I had to suck Doctor Goldman off twice and both times he shot quite a large amount of semen into my pretty mouth and down into my tight little tummy. He also wanted to fuck me, you know. But I told him that would cost extra and he settled for getting oral." I was a little at a loss as to how to carry on this conversation and fumbled. "Did you have an okay time?" I asked finally. "Mm-hmm," she replied. "Actually I quite liked his cock. It was nice and thick with a big purple head. And I didn't even mind taking his load. I washed it down with some expensive Beaujolais." I realized that she was looking down at my crotch as I drove. "Harry, did I just give you a boner?" she smiled. There wasn't too much I could say to deny her allegation. I had another massive woody. I decided to throw my pride away. "Do you think you can take care of it, honey?" I asked. "Oh my God, no!" Vanessa replied. I need you to take me out and buy me a nice bottle of wine. I still have the taste of Dr Goldman's cum in my mouth! You're going to have to wait for me to get in the mood some other time." I nodded and drove her downtown. My dick didn't subside. If anything, it got bigger and harder. We parked opposite an upscale bar. I was wearing dress pants and a shirt and my wood was all too visible. "If you think I'm going to march into a respectable bar next to a pervert with a hard-on, you're quite mistaken." scolded Vanessa. "Take your dick out and jerk it for me right now. I'm going to sit here and watch. No charge. Just don't expect me to help you out." It was a helpless feeling. There was no way in hell my dick was going to go down by itself. So I unzipped my fly and took my stiff prick out and started to jerk it. I glanced over at Vanessa. She had a smug, little grin on her face. "Are you sure you aren't going to help me?" I begged. "Dr Goldman gave me all the dick I feel like handling tonight." Vanessa said. "Your cock is your job, not mine." I kept on stroking my dick. It was starting to throb and I knew it wouldn't be long till I shot my load. Vanessa glanced at her watch. "You almost there, baby?" she asked. "I'm starting to get a little bored. Can you jerk faster?" She handed me a box of Kleenex as I quickly creamed in a massive sticky wad. I gasped and relaxed and mopped at my sopping dong as it became flaccid. Vanessa clutched her purse and swung her gorgeous legs out of the passenger side door. I stuffed my dick and a sheet of Kleenex back into my shorts and zipped up my pants and joined Vanessa walking into the bar. As I put my arm around her waist, she commented, "I guess you really like thinking about how I get it on with other guys, don't you?" *** Vanessa and I hung out a few more times over the next couple of weeks. Her favorite way of spending an afternoon was to tour the pricier, snootier shops in the center of the city and try her luck at getting me to open my wallet. It was Friday afternoon and I had bought her a $100.00 oyster lunch at a patio place. We headed over to an expensive woman's clothing store and browsed through the departments. Finally Vanessa led me into an alcove of fur coats. "Now for instance, I don't expect you to buy me this," she purred. She stroked her pretty nails over a mink price-tagged at over $30,000.00. "I know that you don't have it in you to gift a lady something of this value. But this... now?" A little fur jacket was price tagged at just one thousand dollars. Vanessa tried it on and looked cute and fuckable. I fantasized about seeing her just dressed in the little jacket and nothing else and shagging her and almost weakened. "But Honey," I recovered "I just bought you oysters in the most expensive patio place in town." "I guess..." she sighed. "Well, I'll just have to fuck some more johns, I suppose. That way, I'll be able to afford that little jacket for sure." She smiled at the cute sales attendant. "Maybe next time." *** The following Wednesday, Vanessa and I made a date to go chill at an upscale penthouse bar downtown – at my expense of course. It was the new "in" place for the stockbroker set and was notorious for its high prices and spoiled yuppie clientele. So Vanessa had made a point of asking to be taken there. I picked her up first at a sushi place where she had gone for a meal with a couple of her escort stablemates. By the time I arrived, she was already buzzed and giggly and the leering maître d' and waiters were comping her generously with cocktails. She waved and grinned as I came in. "Do you like what I'm wearing?" she asked standing up. Her outfit consisted of a pair of thousand dollar designer shoes and a stretchy, skin tight red mini-dress that barely covered her pussy and perfect ass. As she turned around, I looked for panty lines and saw none. "Are you wearing underwear?" I queried discreetly. "Uh-uh." She smiled. Panty lines are for losers. I just have to sit carefully and keep my legs close together and I'll be fine." Every guy in the restaurant must have been eyeing her ass as we walked out together. We caught a cab and hit the pricey penthouse bar. It was pretty much as I expected - full of overpriced suits and ties and testosterone. There seemed to be 4 or 5 guys for each of the women executives there. Vanessa drew glances from almost every guy as we parked ourselves at the standup bar. She ordered an expensive cocktail while I bought a domestic beer. After some sipping and chatting, she excused herself and headed off to the ladies' room. It took her about ten minutes for her to arrive back. "Get lost on the way to the john?" I asked. "No, I found the ladies room just fine," she responded. "I got lost on the way back. But a very good looking guy was kind enough to stop and help me find my way into the bar room again." She glanced across the room to a window table where 4 guys were sitting. Three of them were nondescript junior exec types. The fourth however was clearly very tall – about 6'4" – and athletically built. He was about 30 years old and had a strikingly handsome face. I gulped and looked away. Even across the bar room, he exuded an arrogant male sexuality. "He even told me his name," Vanessa narrated. "Tony Collins." "How long did you two chat?" I asked. "Only a few seconds," she pouted. "Unfortunately." I stole another look over at Collins's table and couldn't help thinking of him naked and powerful, mounting Vanessa's naked cunt and fucking it hard and deep with what was almost certainly a huge, thick cock. I was surprised to feel my own dick getting slightly erect at the thought. I couldn't believe what crossed my mind next. "Honey," I said to Vanessa "I have a little wager for you." "Wager?" she asked. "You know that little fur jacket you wanted a few days back?" I said. Vanessa frowned a little and pursed her lips as she recalled the jacket and my refusal to purchase it for her. "Do you think that this Tony Collins guy would want to fuck you?" "Oh my god!" she laughed. "He could barely keep his eyes off my ass while we chatted. I was afraid he'd try and grope me right there!" "Care to put some money on it?" I asked. "Like how?" she said cautiously. I took a deep breath. She was going to think I was a total pervert when she heard what I had in mind. I hesitated. In my pants, my dick was now rock hard and I decided to take the plunge. "If you can get Tony Collins into bed with you three times, I'll spring for the fur jacket. I promise." Vanessa giggled. "And if I can't? Not that that would ever happen. What then?" "I fuck you three times for free," I said. Vanessa arched her eyebrows thoughtfully. After all, it wasn't as if she would be losing any real money if she lost. And she appeared confident that she would easily win in any event. "But I have to have proof that he actually bedded you," I continued. "IPhone photos and video recordings. And whatever else." "Okay," she finally answered. "Game on. I'll give you all the proof you need and then some." "And if Tony Collins just walks out of the bar, you lose. Those are the rules," I said. "That's not going to happen." Vanessa said. She glanced over at Collins' table and smiled slightly for a few seconds. Then she looked at me. "Looks like you've already lost," she said. I caught a glance of Collins' group through the mirror behind the bar. Collins' three bar buddies were getting up and heading out. But Collins didn't join them. He just stretched himself out a little and sipped his drink. Vanessa took my hand. "Grab your beer." She told me. I picked up my drink and followed as she led me across the bar towards Collins' table. He looked up at us. "Hi, Tony," Vanessa said. "This is Harry my friend. I told him you wouldn't mind if we sat here and checked out the view of the city skyline. You can't see it from the bar worth shit." Tony shrugged and grinned. "Make yourself at home," he said. Vanessa scrunched in beside him and I sat across the table. She leaned closely against Collins and pretended to look out through the window past him. "Wow! What an amazing view!" she said. I nodded. "Tony must have the best seat in the house!" Her hand disappeared under the table. I pretended not to notice and stared rigidly at the buildings outside the window. I was breathing heavily and my dick had suddenly gotten hard again. Collins was looking out the window too, avoiding any interaction with me. "Harry," purred Vanessa "Don't you have to make a phone call? The reception's pretty lousy in here," I'm told. "You should call from the elevator foyer." I hesitated. I was getting involved in the whole drama of guessing what Vanessa was doing with her hand. It took me a second to get up and head away. Once out of the bar room, I stood around wondering what Vanessa had in mind. After about 30 seconds, I felt my phone vibrate and picked it up. There was a text from Vanessa on the screen. "Tony's feeling my thigh." She wrote. "What should I do about it? Should I let him put his hand on my bare, shaved, little pink pussy?" I gasped with shock and sexual excitement. "Yes." I texted back. "Does Collins know who you're texting?" After another 30 seconds, I got the response. "Of course he doesn't." Vanessa wrote. "Tony thinks you're too much of a loser for me to contact right now. He doesn't know about our little bet... He's getting so horny, Harry. He's getting quite frantic," she added. I figured Collins must have had as much wood as I had. "What do you want me to do next?" Vanessa texted. I bit my lip. I was tempted to head into the gent's to take care of my raging erection, but there was an even better idea in my mind. I drew a deep breath and texted, "Can you jerk him off?" She replied, "Would that count as one of my three fucks with him?" "No," I texted "I'll pay you an extra $100 if you can get him off in the bar. I have to have proof though." There was a pause of several seconds and then Vanessa responded. "You're a disgusting sick pervert," she wrote. "I need you to pay me $200 to do what you want." "Okay, whatever," I wrote. My hand was shaking. "You better come into the bar then, asshole," Vanessa replied "or you'll miss the show." I put the phone away and walked back into the bar and over to Collins' window table. Vanessa was leaning even more closely against him, still pretending to study the outside scenery. Collins was staring intently outside as well. He didn't even look over when I came in. I slid back into my spot right opposite him. Vanessa smiled. Her right hand was under the table and seemed to be moving subtly and repeatedly. "Have a nice time with your phone?" she teased. "Yes, fine," I answered. I noticed that Collins' face was flushed and he was trying to keep his breathing under control. He squirmed a little in his seat. All at once, he gasped and lurched slightly. I felt something hit my shirt with a wet splat and run down my belly. A piece of food from the table, I wondered. After a second, it occurred to me that Vanessa had shot Tony Collins' load all over my chest and stomach. Vanessa put her hand back on the table and wiped it with a napkin. "I guess we should be going," she said. "Harry and I are so glad we met you, Tony." Collins was no longer breathing heavily. He smiled at Vanessa and pretty much ignored me. "Nice making your acquaintance, Vanessa," he said. As I got up, I realized that Collins had ejaculated perhaps the biggest, thickest load I had ever seen in my life. It had soiled almost my entire shirt front and trickled down onto my pants. I folded my arms over my chest and walked quickly away. "Harry," Vanessa remarked. "For god's sake, you're an even bigger cum bucket than I am! And your dick is still hard." I dropped one hand in front of my pants. Luckily no one else was in the elevator with us. I rushed out and hustled Vanessa across the building lobby and out and down the street to my car. As soon as we got in, Vanessa reached over and squeezed my dick through my pants. I groaned and gasped and shot my load into my underwear. "I guess you're going to need a trip to the laundry tomorrow, Pervert," Vanessa scolded. "You're pretty disgusting when all's said and done. And don't forget about that $200. We're going to stop at a bank machine on the way so you don't try and wriggle out of your little promise," she added. My dick was still trailing cum down my pants as we drove away. I was starting to feel embarrassed about the whole thing and wishing that I had never laid eyes on Collins or that bar. As we turned into the next street, I heard Vanessa's phone ring. She took it out of her purse and smiled at me as she answered it. "Oh my god, Tony!" she smiled. "Oh no. Harry's such a loser, he didn't even notice what we got up to. Tomorrow? ... Sure, I'd love to." END * * * * * * * * * * * * * * * * * * * * * * * * * * * * It's okay to *READ* stories about unprotected sex with others outside a monogamous relationship. But it isn't okay to *HAVE* unprotected sex with people other than a trusted partner. 4-million people around the world contract HIV every year. You only have one body per lifetime, so take good care of it! * * * * * * * * * * * * * * * * * * * * * * * * * * * * Kristen's collection - Directory 82