7 comments/ 284745 views/ 43 favorites Jen & Me: Sis-In-Law Rewards By: Tx Tall Tales Why am I standing here in the rain, soggy paper bags in hand, and afraid to knock on the door? I wonder. My mind wanders back, reliving the events that led to my being here. It all started about 7 months ago... * * * * After a long and trying day, I had asked my sister, Jen, to surprise me with a drink out on the screened-in-porch. (Among the many jobs she had held, bartender was one of the most common.) She came out with a pitcher of some strange concoction, pouring two large glasses. "Thanks, Jen, after a fucked up day like today, this sure hit's the spot." "You think your day sucks? I spent the entire day waiting for those assholes to come by and finish the plumbing on my house. The guys never showed, finally calling to say they won't be there tomorrow either. And I can't be there Friday to let them in. Shit I may never have water again. I way as well move in here for good." She was stuck at our place, ever since her plumbing had exploded. The damn discount plumber her father had found had torn up her kitchen, and left it a shambles, saying he needed some parts. She'd be here at least until the weekend. She'd lived with us for spells before, since we were close to her work and school, and we certainly had the room to spare. "I'm sure Cheryl will let the guys in on Friday." I tried to reassure her. "Sure, whatever," she mumbled, downing half of her drink. "Well this is my last drink for a while. The doctor today gave me a lot of grief. I've been putting on five to ten pounds a years for the last seven years, and now it's causing me knee trouble, and my cholesterol is up. This damn management desk job is going to be the end of me. I've got no willpower for these diets." "I don't know, you lost a lot of weight last year," she reminded me, encouragingly. "Yeah, nearly forty-five pounds on that Atkins diet, but I've gained nearly all of it back. I couldn't eat that no-carb thing for another six months. I was dying for pizza almost every day." I had ballooned back up to nearly three hundred pounds. I was a big guy, but should never be carrying more than about two-twenty. Cheryl had done as poorly, going from one-thirty-five to two-oh-five. "Well you guys are always eating out, and going on vacations. You need to discipline yourselves." "Easy for you to say, you still have a twenty-year-old's metabolism. Wait until you're my age, and life starts playing its little tricks on you. I notice you can eat anything you want," I added defensively. "That's because I work out every day. If you and Cheryl would, it might be easier to lose weight." Being overweight wasn't the only problem I was facing. Lack of fitness was causing a serious problem in my sex life; my wife and I were so out of shape, that sex had become an effort. We only made love about once every few weeks, and then I just laid back, she climbed aboard, and 3 minutes later it was time to clean up and sleep. "Well, I will say that it's keeping you looking pretty good. I'm kind of looking forward to hitting the beach house in a couple of weeks to see how you look in a bikini this year." Oops. Better ease up on the hard-stuff! "You wish, dirty old man!" She was giggling. She lifted up her shirt to show me her abs, which she'd been working hard on. "I am finally getting some definition here. It's about time – I swear I've done a million crunches and leg-lifts." Some inappropriate thoughts raced through my head, as I ogled her 24 year old hard-body. Jesus, I thought, she's not a little girl anymore. "Looks nice! Bet the boys can't keep their hands off of that," I teased. "I wish. I haven't had a serious date in ages. My sex life is the shits. What with school, and work, I have no time for anything. I can't go on vacations all the time like some people." "Try being eighty pounds over-weight, with a partner who's fifty pounds over-weight. Then we'll see how great your sex life is." Shit, I hope I didn't sound as bitter as I felt. "At least you don't have to sweat every weekend wondering if your tips are going to cover your rent, insurance and car payments. I still don't know how I'm going to pay for that damn software my computer graphics class wants me to buy." "Believe me, money is always tight. In my case, you just get to keep adding on the debt. You're going to pay $300 to fix your plumbing; I'm already out almost $10,000 this year on repairs to this old house." "At least you're getting laid regularly." "If you can call monthly, regularly." Ouch. I probably shouldn't have let that slip out. What the hell was she putting in these drinks anyway? "What are you complaining about anyway. You look better at three hundred pounds than I do working out every day. Sometimes I hate my dad. It's his fault I look like this!" We had finished one pitcher of her specialty, and were halfway through our second, deep in the throes of self-pity. The grass is always greener... "How can you hate your body?" I asked, incredulous. "You are so pretty, and you are in such great shape." "I have to work out two hours every day to stay in shape, it's a job in itself. My nose is too big, my hair is too thick, I have a flat ass, and I have no tits at all. How can I have no tits when mom and Cheryl have such big ones? It's not fair." "Come on, they're not that bad." I had seen her in tight shirts and she was small but nice. "Oh, please. Without the push-up padded bras, I might as well be a boy." "Jenny, you're very pretty. And they are not that bad," I answered, perhaps incautiously. "Oh yeah, look at these! Tell me any guy would want to play with these tits!" She pulled her tank and bra up, off her breasts, and I could see the story was partly true. She was almost totally flat. I stared for a moment, stunned, wondering how it ever came to be that my hot little sister was showing me her tits! Not very large, but I would love to gobble them up. "See, nothing to say - 'cause you know it's true. I'll never have a boy friend." She was crying now. Jenny shouldn't cry, it's not pretty, just splotchy. Nose and mascara running, she was successfully countering the effect her bare breasts were having; I pulled her to my shoulder, to give her a place to cry, and tried to pull her bra and shirt back down to cover her breasts. "It's ok, things will get better." "Better for you maybe. You can hit the gym and look great in six months. My tits are so small you don't even get excited; you just want to cover them up because you're embarrassed. God, I hate my life." "Jenny, you are sexy as hell. Sure your tits are small; I would still love to play with them, but I'm married to your sister, so of course, I hold back." It looked like the excess booze and self-loathing was making for a day of true confessions. "Plus," I added, "it's easy to say hit the gym but you've known me for 10 years and I just get worse every year." "You just have to make it a priority. You can do it. You just don't want to. Your life is too easy." "So easy it's made my sex life miserable," I replied bitterly. "So miserable, you have to hide my tits when I'm offering 'em to you for inspection. You've just lost the desire I think, although I can understand you're not wanting mine." Accepting the implied dare, I reached under her shirt, and grabbed her breast. I rubbed my thumb over her nipple. "Can I kiss them?" I asked. "Stop teasing me you bastard. You can't be getting excited over these puny little things." She swatted me on the arm. I took her hand and placed it on my lap, so she could feel how hard I'd gotten. "I guess you're right. I can't get excited over you." She pulled her hand back. "Oh! I'm…I'm sorry." I leaned her back on the couch, and lifted her shirt above her breasts. She just watched me. Her bra was off her tits, and I pushed it up the rest of the way. I then kissed each nipple; stopping on the left one to give her breast some much needed attention. Once her nipple was hard in my mouth, I went back to the other. After a few minutes I stopped, and pulled her shirt down. "You don't have any idea how hard it was for me to stop just now," I confessed. "Things will work out for you, I'll help you if I can. I can help with the computer work. I want you to be happy. How can I help?" "Well..." she hesitated a moment, then caught me totally by surprise when she blurted, "Can you loan me some money for breast implants?" "Oh, Jenny, do you really want to do that?" She looked crestfallen. "Listen, money's pretty tight at the moment, with the holidays just past. I do, however, have some options that vest in June. I can probably help then." "Really?" she enthused. "Sure, our secret. Cheryl doesn't even know about these options – and it's an awful lot of money. I'm planning to pay off all our credit cards and car loans. I can swing enough for implants too." "God that would be great! I'll tell you what. I'll take you to the gym every day, and be your personal trainer," she offered. "I'll make sure you get back in shape, and we'll both be happy this summer. Deal?" "Deal," I answered, shaking her proffered hand. "You know I'm gonna work you hard." "I can't get much harder," I quipped. She blushed. "I'm sorry." "Nothing to be sorry about. Nothing really happened -- just friends working out their problems. Right?" "Right." She didn't sound any surer than I did. The silence stretched out, into one of the very few times I felt awkward around my young sister. She finally broke the silence. "We better get to bed, early morning workout at the Y tomorrow." She stood up and headed for the door. She turned back after a couple of steps, leaned over and gave me a kiss on the lips -- my first. "Thanks." I brushed her breast with my hand, and answered, "My pleasure." * * * * By Monday, Jen was back in her place, and I was in pain all over. After two weeks of investigation, I moved us to a real gym, leaving the Y behind. The Powerhouse Gym was my idea of a gym. Ample cardio equipment, but none of the spandex meat market. Most of the gym was dedicated to free weights, and advanced weight machines. There were still eight each of the gliders and recumbent bikes, and ten each of the treadmills, regular bikes, and Stairmasters. People who came in here came to work and sweat, and not to see and be seen. For four long months, I hit the gym religiously -- three, then four, then five mornings a week. We did some lifting, but the meat of the workout was cardio, specifically extended periods on the stationary bikes. Jenny was queen of the bikes; she could out-pedal anyone, and keep it up for an hour easy. I had done a lot of road biking in my youth, including numerous centuries, up through about age twenty-seven. All those hundreds of miles of riding certainly were no help to me now; when it came to keeping up with her. I was starting to see some pay-off from an improved diet and all that time spent in the gym. I'd gone to six smaller high-protein meals a day, and a variety of nutritional and metabolic supplements. Cut out all soda (at least 5 cokes a day less) and drinking almost two gallons of water a day. I had reduced my body fat from 30% to less than 15%, and had lost forty-four pounds. I was still heavy, but no longer obese. I was putting on some muscle, and was hoping to lose another twenty pounds, and get my body fat below 12%. Cheryl loved the new me. She was inspired to diet by my early success, and Weight Watchers helped her to drop thirty pounds. She joked about Jenny and I going overboard with this exercise stuff, but she was encouraging me, and supported my dieting. Our diets were drastically different, as were our exercise regimens, but we were both making a concerted effort. Our sex life was steadily improving - not stellar yet, but better. Each morning session at the gym, 5 days a week, I watched Jenny on the bikes. She looked so hot, sweaty and sexy in her tight shorts. Too often, I had a hard-on that interfered with pedaling. Since that first evening when we'd made our pact, there had been a little sexual tension, and occasional innuendo in our conversations, but nothing physical had occurred. One morning I had to broach a subject that had me curious. "Jen, how come you always bike in chase mode, don't you ever want to try intervals, or any of the other dozens of profiles available?" "Well, it's kind of embarrassing, but I like to play a little motivational game with myself," she confessed. "And that would be…?" "It's like a race, and I just can't let the chase rider catch me. Ever." "And why is that?" "Then I would be at their mercy," she laughed, a bit too hesitantly. "And you never get caught?" "Never." She was adamant. "So that's why you compare your speeds to the other bikes people are riding, isn't it? I've noticed no one can have a higher setting than you, and no one can finish with a higher distance." "That's right. No one beats me," she replied with easy confidence. "But if they do, they get you?" I hinted. "They never will." "Ah, but it gives us a goal to work towards." I smiled enigmatically. She giggled, and hit me jokingly, but that morning she was really spinning hard, checking my speed, and smiling. After 30 minutes, she had done almost a full mile more than I had. * * * * Five weeks later, I met her in the parking lot in front of the gym with a big grin. "And what has you so happy?" she inquired, while pulling her gear from the trunk. "Three things," I told her. "First, I'm at two-forty for the first time in over ten years." "That's great!" "Second, I'm down to under 12%. New goal is 10%." "Even better!" she laughed, dropping her gym-bag and high-fiving me. "Finally, I have a surprise. I've worked out a barter deal. I'm doing some database work for a web-design firm, they're doing a web site for Dr. Neil Bardon, plastic surgeon, and you have an appointment for Friday morning to select your new breasts, top-of-the-line." She looked at me, stunned. "Really?" "Yep. No workout on Friday; you have to be there by 8:30. But there is a condition." "What?" she asked. "When I hit 10%, I get to see the good doctors handiwork. That should give you at least six weeks." "Of course! You can see them anytime, I mean, are you for real? Really? This Friday?" she was babbling. "For real." I picked up her bag, "Let's hit the weights." She jumped up and gave me a big hug. "This is the nicest thing. How can I say thanks enough? Thank you, thank you, thank you." "Look at me, I'm almost back to college shape. I should be thanking you." * * * * Jenny was driving me mad. It was over six weeks since I had surprised her. She wore sweatshirts constantly now, and I couldn't tell anything about the operation. I asked her how it went and she just said I'd see. For the last few months, I'd been gravitating away from the exclusive cardio and circuit training, and to the weights. My bike time was stable at forty-five minutes, six days a week first thing in the morning before breakfast. I'd added an evening weight-lifting session four nights a week, working about an hour on the free weights, and finishing with another 30 minutes on the bikes. I wasn't working out with Jen much, often doing my lifting in the evening. Although we usually still met for our morning bike sessions. For almost two weeks I had hit a plateau and ceased all progress. The amount of weight I was lifting was not going up, and my body fat, at least according to my Tanita scale, was not going down. I took a couple of days off from the gym, moved my biking outdoors, and went on a juice diet to shock my system into change. I had been riding bike machines so long, I found I had almost forgotten how to ride a real bike, particularly along some of the hilly terrain along the W&OD trail. I had to relearn shifting, and the difference in using toe-clips and generating power on both the up and down stroke, left my legs burning. I embraced the pain as progress, and lengthened my rides on the weekends to several hours. * * * * On Monday morning, after my first century ride in almost 15 years, I was feeling confident. I'd finished the 100 miles in just over 5 hours, along some pretty varied terrain. I was hoping to tell Jen of my progress but she didn't show that morning. I worked out hard that evening, and bumped my bench-press five pounds to six reps at two-seventy-five. I was stoked. I weighed myself in the gym and almost danced. It looked like I had dropped two more pounds, but their scale was notoriously inconsistent. I was eager to share the news with Jen, and with the possible results I barely slept that night. Tuesday morning arrived, and I hit the gym for the morning cardio, barely able to contain myself. "I might be there," I told Jen. "If you've got time, let's hit your place after so I can use your scale and check the body fat level." "I can't, how about tonight, after work? It's Tuesday. Cheryl will be at Weight-Watchers tonight, doing her weigh-in. How much has she lost?" "Thirty-eight pounds; she's hoping to hit forty tonight. She was really strict on her diet this week. Ok, how about around 6:00?" "Sounds good." * * * * At 6:15, I was at her place. "Two-thirty-two and 9.9%," I crowed, "Finally!" "Congratulations! You look great you know; let me see your abs." I opened my shirt. My abs were actually just starting to show a little definition. Ten more pounds and I would be sporting a six pack. "Nice." She ran her hand across my belly. "That's a big improvement. You really are looking hot. I notice some of the chicks in that gym eyeing you. I tell 'em you're taken. They think I'm so lucky." She was laughing, and rubbing my stomach, sides and chest, as she walked around me. From behind, hands wrapped around my midriff, she leaned forward and whispered into my ear, "Do you want to see the other rewards of your hard work?" "Absolutely!" I answered. "Then wait here." She disappeared into the bedroom, and I plopped down on her couch to wait. It wasn't long. Five minutes later she reappeared, in a sexy little red bikini. Her breasts were full, but not huge, not even as big as Cheryl's. "God, you look great! Turn around." She twirled slowly for me, sweeping her long brown hair out of the way with a toss of her head. "Great choice. They fit you perfectly." "Do they look real?" She held them out, examining them for any fault. "I think so, come closer." I sat up for a better inspection. She stopped just in front of where I was sitting on the couch. She bent over to show me some cleavage, then turned again. "Looks pretty good to me." I tried to sound nonchalant, but an adolescent quiver in my voice may have given me away. "Steve, do me a favor?" she asked, embarrassed, "Tell me if they seem real. You know, feel them, try them." "Jenny, I don't know if that's a great idea." "Nothing serious. Like last time -- just friends, please? I have to know. They look good, but will the guys like them? Well, you know..." She was almost begging. "Ok. Come sit here." I made room on the couch. She reached behind her and in seconds, the top was gone. Jesus! I hoped she wouldn't look down; my cock was about to burst free from its inadequate confines. She looked damn good. I could feel my mouth going dry. She leaned back, and I held one breast, then the other, cupping them, weighing them. "Are they still sensitive?" "No, that feels nice." A hint of a smile played across her lips. Perhaps she was testing these in more ways than one. I slipped off the couch and knelt beside her; I slowly bent over and kissed the near nipple. Jen & Me: Sis-In-Law Rewards "Nice," I said. "I can't even notice a scar." "Good." Eyes closed, she had her hand on the back of my neck. I wondered if she could feel the fever in me - I felt like I was burning up. I started kissing and licking her nipples, then the rest of her breast. I let my kisses wander over her belly and up to her neck, while I continued caressing her breasts. Eventually my kisses reached her lips. She responded hesitantly to my gentle kisses. I pulled back. "Jenny, you hit the jackpot. With these, you're irresistible. They are perfect." "Wow, I thought they felt good, but it's hard for me to know." She stood up. "Jenny, can I see the rest? Take off those bottoms so I can see the whole picture. It's killing me." I hoped I didn't sound as desperate as I was feeling. She laughed, and slipped off her bottoms. "Well?" She did another pirouette, finishing with her back to me peeking back over her shoulder. "Irresistible," I asserted, my gaze locked on her tight little ass. "Oh, sure. I notice you're resisting nicely." She taunted. As she turned around, I was struck by a realization. She shaved her pussy. I had never seen a shaved one up close. It was too much; I reached forward and pulled her to me, turning her sideways. I kissed that sweet ass, before kissing the top of her pussy, and massaging her butt cheeks. "Whoa, slow down cowboy. You haven't caught me yet." She laughed, good-naturedly. I let go. "Sorry I got carried away, you just look so damn good." She stood there; so close her aroma was maddening me. "No 'sorries', remember? Just friends. And I guess it's partially my fault for leading you on like that; no wonder you're worked up." She was pulling me to my feet. "Tell you what. In my bedroom; I'll cure your little problem. You can't have sex with me, but at least you won't leave with blue balls." I followed that delicious rear-end back to her room. I figured a hand job from her was better than a self-inflicted one. Jen's room was messy, clothes strewn all around. Her bed was a mattress on the floor, with the bottom sheet twisted and the mattress half exposed. She cleared a pile of dubious clothing off the bed with the expedient and well-practiced use of a foot, and pulled me down. Once I hit the bed, she pushed me into a reclining position, and rubbed her hands over my upper body. "God, you feel nice." Then she took hold of my belt, and started to undo my pants. I was soon naked from the waist down, my only concession to modesty my open shirt. She reached down and started stroking my cock. It was great. I was fondling her ass where I could reach it. Then she surprised me by bending over and kissing the head of my cock. "Mmmmm," she moaned as she took it in her mouth, and starting sucking me off. She turned, lifted a leg, and was soon straddling my head. I couldn't believe this sweet young pussy was so close, so accessible, and so ready. I could see the moistness at the edge of her pink slit. No hair anywhere to distract or hide the incredibly sexy view. I waited in eager anticipation for the taste of her sweet honey-pot as she lowered her smooth pussy to my mouth. Tentatively, I reached out and let my tongue gently part her lips, eliciting an encouraging 'mmmm' around my cock. I moved the tip of my tongue up and down, penetrating a little further, and sampling her from clit to just below her tiny puckered butt-hole. Soon, I was more aggressive, really applying myself, matching her intensity as she worked on me. I held a cheek in each hand, as I licked and rubbed her clit and pussy, and she swallowed my cock like an old pro. After a few minutes, she stopped. "Would you fuck my new tits?" For an answer, I flipped her over on her back. She lay back holding her new breasts apart; my hands were against the wall behind her head, as she squeezed her tits together around my cock. She was trying to press her nipples together against my hard-on. On each forward stroke, she would reach out with her tongue to lick what she could reach. "You're a hot little bitch, aren't you?" I told her. "I'm gonna have to catch you on those bikes to see if you are as hot as I think you are." "You can try," she laughed. "And if I do...?" I insisted. "Anything and everything, I'm yours for a day." She said between licks, awarding me with a very direct look, that promised wonders. I mulled that over as I kept up the stroking. She would occasionally rub the precum leaking from my cock over her nipples. "Oh, baby, I'm gonna come any second. God! You are so hot!" I was really pumping away. "Good, try to hit my mouth." She held her mouth wide open, a smirk dancing across her face, her tongue teasingly darting around the perimeter of those full lips. The wanton sluttiness was too much - I finally exploded and let loose a geyser. The first shot went all over her face reaching to her hairline. The next was mostly in her open mouth. Then, I had my dick in her mouth, and she sucked me off to finish. Long after the last stream had escaped my cock, I was still stroking in and out of her mouth. I had briefly gone a little soft but the view combined with the sucking action brought me to full attention again. Seeing her beautiful young face impaled by my dick was a fantasy that had played its way through my head a number of times -- often when her sister was performing the action in question. The reality was so much better. She looked into my eyes, sucking voraciously, lips tightly clamped to the wide shaft stretching her sweet lips. A puzzled look crossed her features. She removed her mouth slowly, with one last tongue lashing of the crest. "What's the deal? Don't you get soft after coming like that?" she asked petulantly. "Not always. Given hot enough circumstances, I can definitely double up." I grinned, "Believe me, this qualifies as hot enough circumstances." "Cheryl never mentioned this." "Cheryl doesn't necessarily know." I held my cock back out to her lips softly stroking it, not wanting to lose my erection and an excuse to fuck her mouth. I was still straddling her chest, a little higher for better access to the desired opening. Jenny thoughtfully leaned forward and engulfed my cock again. Once I was really hard, I climbed off, and lay back. She dutifully resumed her duties, now using one hand to stroke me as she sucked away. She had a far away look on her face, but even distracted, she performed a better than adequate blowjob. Somewhere inside her head, two plus two equaled four, and she resumed her oral assault with a renewed vigor. She amazed me by arching her back, tilting her head, and with a slow steady thrust, pressing her nose into the hair above my cock. She paused there, seven full, thick inches crammed down her mouth and throat. Then she slowly backed off and proceeded to deep throat me. Each stroke starting with her tongue swirling around my angry red cockhead, and ending with her nose against my belly. "Fuck, Jenny, what asshole ever let you get away? You are an incredible little cocksucker. Amazing!" I emphasized the last word with a firm stroke of my own, into her accommodating throat. She must have felt my impending release. She picked up the pace, now bobbing up and down like a jackhammer. She was standing now; legs spread wide apart offering yet another engrossing view. She was bent over from the waist, gripping my hips; nails dug into the side of my ass, and forcefully fucking her face on my cock. It was too much. "Fuck, Jen, fuck, I'm gonna fill your mouth. Suck me, yeah. Yeah, ooooohh fuck. Fuck. Fuck!" The last was an uncontrolled shout, as I grabbed her head and pulled her face all the way down my cock. I experienced a mind numbing release, buried in her throat. She pulled off the full length, all but the head, and milked every drop out with her hand. She was wearing a wicked smile. "Congratulations, you were my first." "Impossible, no one can do that naturally; who are you kidding?" Laughing, she jumped up, actually skipped to the closet, bent over, shook her ass saucily at me, and then tossed me an open gym bag. A huge 9-inch rubber cock, along with an extensive collection of toys, some of which I didn't even recognize, were there, by way of explanation. While I was looking in the bag, the TV came on, showing a pretty blonde slowly pushing a large ball on a string into her pussy; she was saying something but there was no sound. Wielding the remote, Jenny fast-forwarded the video. "Before I got my new tits, I spent many a night trying to improve the odds that any guy who was with me wouldn't ever want to leave." "God, I've created a monster!" I howled, collapsing back on the bed. Her evil laugh only served to start my cock twitching again. "Oh no, you don't," she cried, noticing the start of my resurgence. "You just came here for a view. The rest was a thank you and an early birthday present. But, that's it! You know what you need to do if you want this." She stuck her ass in my face, fingering her own sopping pussy. I stood, pulled her up and gave her a kiss. "Thank you very much, I had a delightful evening. I believe I have to go train now." I recovered my clothing and started to dress. The evil girl parked her butt on the edge of the mattress, and gave me a show with a foot-long, double-headed, neon dildo as I finished dressing. Then escorted me to the door by my hard cock, and sent me on my way. I think Cheryl was surprised (and delighted) to be the recipient of a protracted bout of amorous gymnastics that evening. * * * * My fortieth birthday finally arrived. I was at two hundred thirty pounds, and Cheryl was at one-fifty-five and had started walking five days a week, at the park after dropping our daughter off at Montessori school. In just over seven months, we had made great progress towards fitness and happiness. For my birthday, we went to Ruth's Chris Steakhouse. She surprised me with some restraints, inviting me to tie her down and have my way with her. We had never even broached the subject before. The restraints were exciting and fun. It was a complete package that included sheets, some Velcro restraint tie-downs you could position anywhere on the sheet, and of course, ankle and wrist cuffs. We had a great evening of sex, some of the hottest since we'd been married. I would be less than truthful, however, if I denied occasionally thinking of her hot little sister when my cock was buried in her mouth or pussy. I wondered if she fantasized about anyone. * * * * I had a plan. I had continued with my road biking, returning to old trails and familiarizing myself with them. I'd upgraded to a new Cannondale Multisport 800, and was amazed at how much easier the newer lightweight bikes, and advanced gears could make riding. I'd taken Jen down to the store when I got mine, but she wanted a mountain bike. She settled for a Trek 8000, enamored by the fancy shocks in front, and the easier to access gearshift levers. We had biked outdoors together a few times, but I had hidden from her the fact that I had put in probably more than a hundred hours on the roads. I decided to challenge her to a race. I had charged the bikes when we bought them, and she was to pay me back. "Tell you what," I told her when she met me at the beginning of the W&OD trail, just outside of Vienna in Virginia, "let's make this a race." "You know you don't stand a chance, loser," she teased me. In our last few outings, she had beaten me to the finish each time. "Then you shouldn't be worried. If you win, the bike is yours, you don't have to pay me back, it's a gift." "That's awfully generous. And what if you win?" "Then I will have caught you. You know the penalty." We hit the paved trail, on a stretch where there was a nine-mile run where we didn't have to cross any streets. It was ideal for racing. "You know I'm going to catch you." I warned her. "Right. Not in this lifetime." She retorted. "First one to the Reston overpass?" "Sure." Jenny is a beautiful girl, and in great shape, but not always the sharpest tool in the shed. I had a huge advantage here, and was so smitten with her, I was going to take every chance I could to improve my odds. She didn't know the trail; there were twists and turns and some long hills. About twelve years back I had ridden this trail nearly every day for an entire summer. Recently, I had ridden the path, refreshing my memory during lunch and on weekends, at least twice a week. The nine miles took just about half an hour. I had practiced racing the path at lunch three times last week, unbeknownst to her. If knowledge and familiarity alone weren't enough, my bike was much better under these circumstances than hers. Her mountain bike might be ok at starts and climbing the hills, but on long straight-aways and particularly on the long downhill segments, my gearing could be a huge factor. Then there was the biggest, most telling advantage of all. These bikes had gears. The gym ones didn't. Where we had been biking, down by the river, Jenny never had to change gears. Her knowledge in this area was almost non-existent. The race started out with a series of twists and turns through a park. She got a little ahead out of the blocks, and stretched her lead when I got caught behind a couple of joggers, who didn't understand that the shout of 'on your left' was an indicator to make some room on the trail. I caught her struggling up the first steep hill, getting the hang of the gears. We reached the peak almost together, and I was able to stretch out a lead on the downhill portion. Jen was already breathing hard after the first hill, and I kept looking back to check her progress. Not smart for a race of any kind, but I may have been a little over-confident. She was pedaling hard as the trail straightened out, for a very long slight uphill run, ending in another steep hill and an overpass. She made up most of the ground she'd lost on the straight portion, and was on my heels up the hill. I missed the gearing, and lost some momentum, and she shot past me up the incline, showing a much-improved grasp of the shifting. When I hit the top, she was a good twenty yards ahead of me. Again, I shifted to my lowest gear, and was soon on her ass. I slipped in behind her, willing to slipstream a while, and let her burn up the energy cutting the wind for both of us. The view from behind was delicious. She had on a sports bra, which exposed most of her back, and the sheen of sweat from the exertion glistened in the sun. Her ass looked scrumptious in her tight pink biking shorts. For almost two miles I enjoyed the view. The last of the major hills were just ahead of us. There were two hills back to back, but there was a trick here. After the first hill, there was a pretty tight turn at the bottom. If you slowed down too much, you'd lose your momentum for the second hill. There was a section where the trail separated to go to a parking lot. If you took the parking lot portion you could maintain a lot more speed. I pulled around Jen at the base of the hill and pushed real hard up the hill. She stayed glued to my side, refusing to give any ground, and the steepness of the hill gave her a slight advantage, carrying less weight and having the improved gear ratios. She edged me out to the top, and started down the hill. Again I pushed her, pedaling hard, not quite all out. She was turning the pedals faster to keep up, and breathing really hard now, but again staying a half-bike length ahead. About twenty yards from the divide I dropped behind her again, and split off to the parking lot side of the trail, as she stayed on the main portion. The squeal of her brakes as she entered the tight part of the turn let me know I had this race won. I hit the second hill with virtually all my speed intact and pedaled hard, not looking back. At the top I finally ventured a glance and saw I had gained a huge lead, over 20 yards. From the top of the hill to the end was a little over a mile. I topped the hill, stood on the pedals, and dropped to my lowest gear. I pedaled all out for that last mile. My lungs were aching and legs were burning when I reached the start of the Reston overpass. Looking back, I found Jen only about 30 yards behind me. How she had managed to stay even that close, I have no idea. I was sitting beside the trail, just regaining my breath, when she dropped beside me, chest heaving, legs shaking. I passed her a water bottle, full of Gatorade. When she finally spoke a minute later, she was still very red in the face, a mixture of effort, anger and embarrassment. "How'd you do that?" she demanded. Yes, definitely anger. "Jenny, you are a gym biker. I've been a road and trail biker most of my life. It's a different critter. We can work on it, teach you the gearing, the trail, and how to ride in the real world. Then we'll race again." "NO," she snapped, "you won, fair and square. When will you have your prize?" "How about this weekend? Cheryl is going to that baby shower in Pennsylvania. She'll be gone from Friday until Sunday morning. Grandma has the kid. How about Friday night until Saturday noon?" "Well, I guess we can include an overnighter, but only if you bring the dinner." * * * * Enough reminiscing. I'm getting soaked in the rain, a bag with, among other things, two freshly steamed lobsters in my hand. I knock on her door, sporting a hard-on I expect I'll have most of this weekend. "It's open." I open the door, and she's standing there, wrapped in cellophane, with a big bow around her breasts. "Come open your prize." She says. I put down the food, and walk over to her. I give her a big kiss on the lips, then undo the bow. I pull at the cellophane and she starts spinning as I unroll her. At the end she's dizzy, and leans against me. "You know, I'm glad you won," she whispers. "I'm glad you're glad, and hope to make you gladder." I tell her. I scoop her up and carry her to the bedroom. She's actually cleaned the place, and I lower her to the bed. She watches me undress, leaning back, and talking dirty to me. She's rubbing her breasts. "So, Steve, are you gonna fuck me good? Are you going to make me beg for it? You want these breasts, they're yours, my mouth is yours, my pussy's yours, and I'm yours. You may never get me again, so make it good." I am so hard I know I won't last long this first time. I kneel between her legs, and without another word, I'm sticking my cock in her wet pussy. I figure seven months of foreplay is more than enough. She's ready for me, clearly. I lean over, kiss her mouth, and then start fucking her with long firm strokes. She is instantly moaning passionately. After a couple of minutes I pull out and roll over, my cock standing at the ready. Taking the hint, she squats down, lowers her pussy onto my hard cock, and starts raising and lowering herself onto my prick. Ahhh, the advantages of getting fucked by a girl in shape. Her eyes are closed and she is lifting up about half way, then easing her self down onto me. I reach up and start playing with her breasts. She drops to her knees, and leans forward. Her breasts are in front of my face and I alternate which I suck on as she rocks back and forth on me. She's talking again. "You like those big boobs don't you. I can tell by how hard you are. Fuck! You feel good inside me. Don't come yet. Oh fuck, you feel good!" "Don't worry if I come. I'll be doing that a lot for the next twenty-four hours. Just enjoy it; I know I will." "Oh, I'm enjoying it; I am." She assures me. She's impatient, and sitting up she spins around so she's facing my feet, and starts fucking herself on my cock again, harder now, slamming herself up and down. I grab each delicious cheek, and lift her on each up stroke, letting her lower herself back down. Her ass looks so good; I have to play with her little butt-hole. Jen & Me: Sis-In-Law Rewards "Oooohh," she moans, speeding up again. I'm getting close now. I push her forward, so she's on her hands and knees. I kneel behind her, and enter her again. I've got a hand full of tight, tanned ass, a hot young moaning college girl pushing back on each full stroke, and I'm slipping my thumb in her sexy little asshole. She's talking dirty again. "Fuck! Fuck me! Fuck me! Yes! Yes! Fill me with your big hard cock. Make me come, Steve, make me come." I try to oblige. Fucking her hard and furious now, my thumb solidly lodged in her ass, giving me added leverage. I reach forward and push her head down to the mattress, adjusting the angle of attack. I spread her legs, and kneel a little higher, now fucking down into her bald, steaming pussy. I must have found the spot; she's shouting "Fuck! Fuck! Yes! Yes!" alternately with loud moans, squeals and finally a scream as she comes as hard as anyone I've ever seen. I'm grabbing her hips tightly in each hand and pounding her tight cunt with all seven inches of hardened steel as hard as I can. The sweat is dripping off me, landing in small splashes on her beautiful tight ass cheeks. I can feel the cum rising up, and know it's time. "Ohhhh, fuck! Take it! Take it! Yessssssss!" I'm releasing shot after shot of cum deep inside her pussy, and still slamming my cock into her hard, until the last spasm is finished. She's breathing like a hard ridden horse, which I guess is appropriate. "Oh, I can feel it. I felt each shot. I could feel every hot jolt of your cum deep in me," She tells me, breathlessly. "I biked at least five thousand miles in the last few months just to get in that pussy. It was worth every inch." I pull out and lay next to her, holding her in my arms and nibbling her neck. "You are gonna get more cock this weekend than a two-dollar whore." "Good, I'm due. Let's have dinner." She says, bouncing up. God, the energy of the young. "Dinner and a movie?" "What did you have in mind," she asks coyly. "Your training videos, and any self-portraits. I want to know what resources I have available to me." "You set the dinner out on the coffee table, and I'll get my favorite - "Secrets of the Pornstars " - I think you'll like it too. I'm pretty sure I got it back from Marisa." "Marisa?" I ask, puzzled. "Isn't she married?" "Married for money, prowling for fun. Or so she tells herself. She keeps telling me she's going to get even with that bastard, but she's a coward." "That's too bad, she's a nice girl, I thought her marriage was going well." I have known Marisa exactly as long as I've known Jenny. She's been married about three years if I recalled correctly. "It was, until she found out he's sleeping with a girl that works for him, a real skank, and that he hits on me all the time, and Julie. The dick claims he has needs that Marisa can't fulfill. What a load of crap. He was even pushing for a threesome. Like that's going to happen. What a prick. She should dump him, but she likes being spoiled, and he is rolling in it." The video is in the VCR rewinding, and I set out the wine. The dishes are set and dinner is ready. I've melted a pound of butter, and pre-cracked the tail and claws. For accompaniment, we have quartered new potatoes with parsley, and a small shrimp salad. We sit at her coffee table and she's teasing me, eating her lobster as sexily as possible, licking her lips and fingers. Occasionally feeding me morsels. She reaches for the remote and starts the video. "This is my number one self-training tape. They show incredible techniques for blow jobs, foreplay, delaying ejaculations, various sex positions and the advantages of them - all interspersed with some of the hottest sex from actual movies." She's fast-forwarding through some couples on a bench, apparently talking to an interviewer. Together we watch an incredibly detailed explanation of a blowjob, with a variety of techniques. Then they're showing a scene with this hot blond swallowing a monstrous cock. We finish our meal, and I sidle over next to her, as we continue to watch the film. We're not talking much now; occasionally she mentions a favorite action, or asks me what I think. Her hand is in my lap, as she idly strokes my hardening cock. "There! I want to try that!" she says excitedly. We're watching a segment on toys, and a man is screwing a girl doggy style. She has a string of six balls, at least half an inch across pushed into her ass, one at a time, as he is slowly screwing her. He is picking up the speed of his fucking, and massaging her ass cheeks. Only a string remains of the line of balls. Now she is telling him she's close, she's gonna come, don't slow down, now - now, and as she's coming he pulls the string of balls from her ass one at a time - and she's screaming and shaking all over as she comes and comes. "I think we can manage that," I tell her, "if you have the accessories." A few minutes later we're positioning ourselves on the bed. I've got some mystery lubricant from her bag, and the balls on a string lay out next to me. These are pretty big, about three-quarters of an inch across. She's sucking me again, preparing me for our play. I guess she feels I'm stiff enough; she turns about, ass held way up, clutching a pillow to her chest as she places her head on the bed. I slowly enter her hot juicy pussy, and rhythmically start the action. After a minute, I take some lubricant and squirt it right on her asshole. She moans loudly and shakes a bit. Using one finger, I start working it in and around her tight little opening, maintaining a steady stroke with my finger. "You have such a cute ass. Your tight little hole is a nice light brown and looks good enough to eat. Are you ready?" "MmmHmmm," she responds. "Good." I take the strand, place the first ball against her hole, and gently push it in. It goes slowly until it pops in. "Oh, God, that feels wild." Jen is moving her ass cheeks in some kind of wave motion, almost dancing under my assault. I, in turn, press in the remaining five balls. I have a little trouble when number four tries to pop back out, but finally get them all in. I use my finger to ensure they are in deep enough, to avoid them trying to pop out on their own, then massage her cheeks, pushing them together as I rub her butt. "Yessssss. Steve, it feels sooo good. Now, fuck the shit out of me - fuck me, fuck me hard." I need no further encouragement. This scene has really gotten me excited. I only hope I can last long enough for her to reach her own sweet release. There is a loud slapping as her ass cheeks meet my hips with each long, deliberate, hard stroke. I'm now picking up the pace, screwing her hard and fast. I can feel one of her hands playing around where my cock is entering her. She is thrusting back hard at me. I'm going like mad, pounding her as hard as I can. The force of my thrusts inches her body up the bed. Her head bends sideways where it meets the wall, and she has nowhere else to go. The hard fucking is shaking the pictures on the wall, and she is crying out- I only just remember to pull the balls from her ass. I know it's time, and on the very first one, she lets out a scream that astounds me. She is shaking all over, her hands clenched into tight fists. One fist is hitting the wall. I slow down and give her long strokes, the full length of my cock driving in and out, and I pull out the second ball. She raises her body on her arms and her legs are twitching. "Ohhhhhhhhhhhhhhh," her voice is quivering. The third ball comes out, followed by the fourth. Her whole body is bouncing now, one hand against the wall as she pushes back against me. On the fifth one, she cries out again, loudly. "God you are hot," I tell her, "I'm almost there, the last one comes out when I come." "Yes, yes, fuck me, hurry," she gasps. She appears to be coming in waves. Grabbing both cheeks tightly I speed up the long strokes, and feel the cum welling up in me. "Yes baby, now, I'm coming now." With the first spurt I cram my dick in her to the root, dumping my seed in her, and pull out the last ball. She collapses to the bed, shaking, curling up into a ball. I fall with her, sliding my leg around, and still fucking her as she lies on her side, knees pulled up to her chest. "Please, enough, oh, stop, oh," she moans, as she pushes a hand against me. I stop pumping, and lay down next to her, gently stroking her and hushing her, trying to calm her down. Just as I think she's calming, a spasm shakes her body, and I can feel her pussy clenching at my shrinking cock. Another wave, ten seconds later, appears to be the last. She's breathing very hard, and talking softly, I can just make out her words. "Oh my god, that was incredible." She is totally spent. "I must have come a dozen times. No-- more." "You came continuously for the last five minutes. It was the most amazing thing I ever saw." I get up to get us something to drink, and return to find her sleeping. I decide to clean up our dinner mess, and let her sleep. I still have the morning. I finish the cleaning and place two large glasses of ice water beside the bed before I go through the bag of toys. I finally settle on some leather restraints, a large vibrator, and a butt-plug for the morning. I turn out the lights, curl up behind her, and reach around to hold one of her sweet new tits. I fall asleep with visions of her cumming under my ministrations dancing through my head.