3 comments/ 51988 views/ 13 favorites The Main Line: Doggie Style By: MainLiner1903 My story beings shortly after returning home to the Main Line after serving in the Army for three years. I was twenty-five years old, and not sure where life was taking me. My time in uniform had not been terribly dangerous, but it did change my perspective on the world. Life was short, and tomorrow was never guaranteed. For those who are interested in such information, I stand just above six feet, with brown hair that is still kept short. I was already fairly athletic before enlisting in the Army, but three years of intense physical training left me with a well-toned body. My shoulders are broad, my chest is firm and hairy, and I can run all day long. I also must wear Magnum sized condoms. I am a Main Line native. Growing up I was a spoiled kid who just assumed that everything would be given to me. I entered a prestigious college, but was kicked out during my junior year for reasons that I will get into later. The experience left me shaken, and led me to enlist as a private in the infantry. I was discharged in the early spring of 2008. Since I had nowhere else to go, I headed back home to live with my parents. It was not such a bad deal since they spent time at their other homes in Florida and Maine. Often I had the place to myself, which made entertaining dates quite easy. The problem was that I had no job. My pay as a lower enlisted man in the Army had not been much, and while I had a small trust to my name, it did not provide enough to live off. I needed to find some positive cash flow, but had no clue what I wanted to do. One day a friend of my parents, who owned a dog walking service, suggested that I come work for her. Thus began my strange odyssey of walking dogs for the women of the Main Line, and slipping into some of their beds. The Interview I had never met Carolyn Bradford before leaving home for the Army. She and her husband had moved to Malvern from Atlanta while I was in basic training. He worked in the financial world, and apparently was quite good at what he did. Carolyn had befriended my parents at their country club, and now the two couples were quite friendly. It was at the club where my mother told Carolyn about my situation. Since her children were all grown up, and her husband was busy with work, Carolyn had gotten quite bored with life. She loved dogs, and started a small dog walking company, that quickly grew into one of the most popular on the Main Line. She had several employees, and according to my mother she did quite well on her own. After hearing that I was in need of work, Carolyn suggested to my mother that I meet with her to see if I would like to do a little part time dog walking. She said that it would pay about seventeen dollars an hour. At first I thought it seemed like a stupid idea, but since I didn't have much else on the table I figured I could hear her out. So one Monday morning I gave Mrs. Bradford a call. On the second ring I heard a woman with a sweet Southern drawl pick up. Her accent was not strong, but quite evident. I had been stationed in Georgia during part of my time in the Army, and was immediately reminded of the Southern Belles that I had the fortune of bedding. "Hello?" she asked sweetly. "Mrs. Bradford, it is Will Thompson" I replied. "Of course, Jill and Robert's son. How are you?" she cooed. "Doing well, thank you. My mom said you might have a job opportunity for me?" The sound of her voice flooded my memory with those hot nights in Georgia. "Yes, honey. But I think we should talk about it in person..." So we arranged to meet for lunch that afternoon at the White Dog Café, a rather swanky place in downtown Wayne. It was a beautiful April day, with clear skies, and temperatures in the low seventies. I threw on a dark blue Lacoste shirt, khaki slacks, and black dress shoes. I do know how to blend into the scenery of the Main Line Society when I want to. As I pulled into the parking lot I received a text from Carolyn that said she had a table outside, and to just give her name to the hostess. I followed her instructions, and the hostess led me to the outside seating area. It was on the early side, so most of the tables were empty. As such, it was easy to pick out Carolyn, as she was sitting alone and browsing through the menu. "Mrs. Bradford?" I asked as I walked into her line of vision. She smiled and stood up, allowing me to take her in. Allow me to provide the details. At five feet, six inches or so, she was neither too tall, or short. Her thick, blonde hair (the coloring was in the hands of a professional) came to just above her shoulders. Her eyes were covered with an expensive pair of Chanel sunglasses, but underneath I would later discover blue eyes that seemed to cut right through you. She also had one of those disarming smiles that immediately made you feel at ease around her. She was in good shape for a woman who had already celebrated her fiftieth birthday. While not ripped by any means, she had curves in all the right places. She wore a conservative, dark blue wrap style dress with a sash around the waist, which made it hard to gauge her chest size. I would later learn she was a full thirty-four D, natural of course. Her dress came down to just above the knees, exposing her shapely legs, and what appeared to be an expensive pair of black and white heels. Her engagement ring was huge, and her wedding band just was equally impressive. "So nice to meet you Will." She beamed while shaking my hand. "Likewise Mrs. Bradford." As I took her hand and shook it firmly. "Oh honey, please call me Carolyn". My cock was already stirring. So we had an enjoyable lunch out in the warm spring air. We talked about my time in the Army, our mutual connection to Georgia, and then finally her dog walking company. I kept checking her out throughout the meal, which her company of course paid for. I have no doubt that she caught me admiring her on more than one occasion, but frankly I did not care. She was a beautiful woman, and she knew it. As we finished dessert, she laid out the details of the job. It would be part time at first, probably around twenty hours a week. I would meet with clients, get to know them, and their pets, then come back three times a day while they were out of town. It seemed easy enough, and I expressed my interest in the position. Hell, I would have expressed interest in the position even if she ran a septic tank cleaning business. "So Will, I think you would be ideal for the job, and your mom told me that you are great with dogs, but I need to do a trial with your first." She told me as picked up the check. "Ok." I replied, not sure where she was going. "I have two golden retrievers at home who are my unofficial recruiters. I know this sounds silly, but I would like you to meet them so that I can see how they react to you. I have no doubt that they will like you, but they are my litmus test for new applicants". She told me as we walked out to the parking lot. I told her that was no problem. She asked me to follow her back to her place, and that she would only need about twenty minutes of my time once we got there. Eager to get the job, and stay in this sexy woman's company, I of course agreed. I got behind the wheel of my truck, and followed her BMW X5 through the back roads of the Main Line, and out to her home in Malvern. The house was large, but not grand, and sat on a nice lot in a very quiet corner of Malvern. I parked my truck and walked up to her, admiring her backside as she bent down to pick up her purse from the front seat of her car. "Nice place." I said as I looked around. "Thanks. We got it for a song in the depths of the recession." She said with a tone that showed no remorse. I followed her inside, and was immediately greeted by two large Golden Retrievers, who barked, and carried on as we entered the foyer. They greeted Carolyn warmly, but approached me with caution at first. I put my hand out to let them sniff me, and within seconds they were licking and jumping up on me. "Well, I think they like you!" Carolyn said as she watched her dogs greet me. I followed her to the back of the house, where she let them out to the fenced in yard. We stood on the patio, watching them run around, and have a good time. A few minutes later one of them came running back and jumped up on me, his muddy paws making my shirt rather dirty. "Oh Terrence, bad dog!" Carolyn yelled as I examined the mess on my shirt. "Oh Will, I am so sorry honey, they just get carried away is all." I smiled at her, "Please Carolyn, no need to apologize" She looked genuinely upset as she examined the marks on my shirt, "And such a nice shirt too. Please, let me treat it for you real quick so that it doesn't leave a permanent stain." I began to object, but she would have none of it as she gestured for me to follow her inside. Her heels clicked loudly as she led me through the kitchen, and down into the basement, where they had a large laundry area. The rest of the basement was finished off with a game room, and a small suite. I stood in the doorway to the laundry room as Carolyn rummaged around the cabinets, looking for a spot treatment. "Honestly, I never come down here, our cleaning lady does the laundry for us." She announced as she stood on her tiptoes looking through a high cabinet. "A ha!" She yelped as she found what she wanted. She turned and looked at me, "Ok Will, give me that shirt. I will treat it and throw it in the wash for you" I was a bit taken aback, and before I could reply she smiled, "Oh honey, I raised three boys, no need to be shy. That is an expensive shirt, and I don't want to see it ruined." I couldn't argue with that logic, so I peeled the shirt off, and handed it to her. She applied the spot treatment, and then threw it in the washing machine, setting a new cycle. As the machine began to fill she turned and looked at me again, pausing as she took in my chest. "Well, they certainly worked you out in the Army, didn't they?" As she smiled coyly at me, her eyes looking up and down my body. I could already feel the blood flowing to my cock. Did she just come on to me? I told myself to take it easy. She walked closer to me, her mesmerizing blue eyes fixed on mine. "Was it tough, being in the Army?" She asked. Not sure what to say I cleared my throat, "Let's put it this way, I am glad I am out". Without a word Carolyn reached out, and traced her fingers down my defined abdomen. "You are quite a specimen". She said while smiling at me rather mischievously. "You aren't too bad yourself". I found myself saying. She beamed at me and said, "You are a trustworthy guy, aren't you Will?" "What do you mean?" I asked. "Well, I mean, are you good at keeping things, shall we say, discrete, when necessary?" She said as her fingers rotated in circles around my navel. My cock was growing by the second at her touch. I played coy. "I don't think I follow." The scent of her perfume was intoxicating as it filled the laundry room. She laughed, "I love my husband. I truly do. But he is gone a lot, and well we have been together a long time. So, when a handsome young man such as yourself falls into my lap, well, I like to take advantage of the situation." "Take advantage?" I asked with a smile. She smacked my arm playfully, "You know damned well what I mean. But I need to know that I can trust you, and that you won't jeopardize my marriage, family, or business if we fall into bed together". Her face became very serious as she said this last part. I reached out, tugging gently at the sash that was tied around her waist, "You have nothing to worry about Carolyn." I leaned in and kissed her softly on the lips, which led her to release a soft moan. My fingers untied the sash of her dress as we kissed as new lovers, gently exploring each other. I slipped my tongue into her mouth, which she began to suck on gently as I parted her sexy, wrap style dress. Her large breasts were encased with a dark blue mesh style bra that had roses inlaid over the bra cups, and panties. It was a beautiful set, and it made her already amazing chest look even bigger. I let out a deep breath, "Damn, this is pretty." I traced my fingers over the bra cups, feeling her nipples harden underneath. "Thank you." She said as her fingers undid by belt, and unbuttoned my pants. I kicked my shoes and socks off while she lowered my pants and boxers, letting my hard cock sway free. "Wow, look at that!" She cooed as her fingers gently traced over my rigid member. I slid the dress off her shoulders, and picked it up, placing it gently on the dryer. She grinned at me, "Look at you being all polite. I guess you picked up some manners in Georgia!" I chuckled as she took my hand, and led me out of the laundry room, and to the guest suite on the other side of the basement. Her Hera-like body was amazing to follow. Her ass had a lovely heart shape, and she knew just how to sway it as we crossed the basement. The guest room had a queen-sized bed, which had a navy blue duvet on top of it. She stood at the foot of the bed, bending down to slip her heels off. At the same time I unhooked her bra, letting it slip off her body. I kneeled down as she stood back up, sliding her panties down to her ankles, and letting her step out of them. I stood behind her, looking at our reflection in the mirrored panel over the bed. My hands reached around to knead her amazing breasts. I slid my hard cock between her legs, pushing the top of the shaft up against her. I slowly pushed my hips back and forth, letting my thick, hard cock rub against her while I kneaded her chest. She let out a louder moan this time, "Oh baby, you know just what you're doing, don't you?" I kissed the back of her neck and whispered in her ear, "You're about to find out." With that we crawled onto the bed together, embracing as lovers. We kissed deeply as our hands explored each other. My fingers kept returning to her chest, as I rubbed her erect nipples between them. I leaned down and took her right nipple in my mouth, licking and sucking on it, then blowing gently before taking it between my teeth. I would lift the breast up a little by my teeth, which received a positive response from Carolyn. "Oh baby, that is nice!" She mashed her breasts together as I suckled them for a good ten minutes. Moving back and forth over her nipples, making her areoles slick with my saliva. Soon Carolyn became inpatient, and grinned at me as she kissed down my body. She began with my chest, and slowly moved her way further down my body. Each kiss barely glanced my skin, but it felt incredible. When she reached my cock she took it in her right hand and kissed up one side, and down the other, before swirling her tongue around the head. I was in heaven as I watched this beautiful woman begin to give me an epic blowjob. She licked up the bottom side of my shaft, and then back down again, and then sucked on each one of my balls. This later action caused me to moan loudly, which she seemed to enjoy hearing. She kissed back up my cock, then took it in her mouth, slowly. She eased it in her mouth with an expert's touch so that she almost took the whole thing in before bobbing her head up and down on it. What I couldn't see, but could certainly feel, was how she rolled her tongue up against my shaft as she sucked me off. To this day it is still one of the most amazing blowjobs I have ever received. I could tell that sucking my cock was really turning her on, and I offered words of encouragement, which seemed to further arouse her. She played with her breasts with her free hand as she sucked me. I held her hair from her face as her sexy, red lips were wrapped firmly around my shaft. It truly was a sight to behold. She finally came up for air and gasped, "I want your fucking cock inside me right now!" Who was I to deny my new boss? I lay fully on my back as Carolyn straddled me, lower her dripping pussy lips to the tip of my cock. I reached around to squeeze her heart shaped ass while she slowly lowered herself down on me. The sensation of her pussy gripping me was amazing. Soon I was all the way in, and my cockhead was hitting up against something inside her. "Oh Jesus!" She moaned as she slowly began to bounce on my hard shaft. I reached around to spank her ass while she did, which only caused her to go faster. "Oh fuck you are big!" She sighed as she leaned forward, which allowed me to suck on her amazing nipples again while she moved up and down on my cock. The sensation of having my cock slide all the way inside her, then back out again was incredible. I was in absolute heaven as this sexy blonde rode my cock, shoving her big, natural tits in my face. Next, I had her lean back on her arms, letting me rub her clit as she ground down on my cock. This put her over the edge, and she moaned, "Oh God I am going to cum!" Soon she was gyrating around my cock as she came in waves. It was amazing to see her facial expressions as she climaxed. I am a big doggie style fan, so as soon as she came down from her orgasm, we repositioned. I stood at the foot of the bed as she got on all fours. I slid my cock back inside her, and began to let loose. First my strokes were slow and steady, but the sight of her big tits swaying in front of made me go harder and faster. I would occasionally reach around and squeeze each breast before gripping her hips again. My hips smacking loudly into her as we fucked like two animals in heat. The bed creaked loudly as I let loose, fucking her as hard as I could. Her moans of encouragement only caused me to go harder. Soon our bodies were soaked with sweat as I felt the cum rising up my cock. Carolyn came again, gripping the duvet so hard that he knuckles went white. "Ayeiieeehhhhh!" She screamed in her Southern drawl as she came again. "Fuck I am close!" I moaned. "Where do you want to cum?" She gasped. I pulled out and grinned at her, "In your mouth." She looked at me with a twinkle in her eye and kneeled before me, taking my slick cock in her mouth. The sight of this married woman sucking away on me like that did the trick. Soon I was exploding down her throat. At the first touch of my cum she wrapped her lips around my cock tightly. She swallowed every drop, which provided a sensation that was so incredibly pleasurable that I do not know how my legs held up. Full spent, we collapsed on the bed together, breathing hard. Carolyn looked at me and smiled, "You are so hired." Thus began my employment at Carolyn's dog walking company. We would continue to fall into bed together in the months ahead, but nothing compared to that first encounter. And thus my odyssey began. The Main Line: Doggie Style Ch. 01 Please read my introduction to this series, The Main Line: Doggy Style, to get the full background of the series. For those of you who are unaware, the Main Line is a wealthy suburban area just west of Philadelphia. The name derives from the passenger rail line that runs out of the city, and west towards Pittsburgh. Chapter 1 -- Learning the Ropes It was the morning after my "interview" with Carolyn Bradford, and I awoke in my childhood bedroom with a raging hard on. Did that really happen yesterday afternoon? I rolled over, and looked at the clock on my nightstand. Next to it was Carolyn's business card, which had the contact information for the person who would be training me on how the company operated. I sat up, and looked at the card. Just seeing Carolyn's name brought back images of her large breasts in my face. Her full lips wrapped around my cock. Fuck, I thought to myself, I need a cold shower. Ten minutes later, as I walked back into my room, my phone started to ring. I looked at the number, but didn't recognize it. "Hello?" I said, while drying my self off. "Will?" It was a girl's voice, and she sounded rather hot. "This is Kayla Martin. I work for Carolyn. Did I wake you?" "Um, no, actually I just got out of the shower. Thanks for calling". I said, while throwing my towel on a chair. "Yeah, no problem. Anyway, I am heading over to one of my client's homes this morning, and Carolyn said I should walk you through the whole process. The house is in Paoli. Is that far from you?" "No, not at all. Do you want to meet at the house?" I said while pulling out some clean boxers. "Actually, why don't we meet at the Starbucks on Lancaster Avenue, and we can just go in my car. Say around ten?" "Yeah, sure, see you then. But how will I know who you are?" I felt like we were meeting for a date. "I will have a Villanova shirt on, and be carrying a leash". She said after giggling. So I walked into the Starbucks a few minutes before ten, and looked around. The place was empty, so I ordered a drink, and waited for it off to the side. A few minutes later she walked in, and I was instantly drawn to her. For those of you keeping score at home, Kayla was twenty-one years old, and played field hockey at Villanova. She kept in great shape, but still had very soft feminine features. She stood about five feet, seven inches or so, with amber colored hair that fell just below her shoulders. She had pretty green eyes, and a fair complexion. Her body was well toned, but I could tell by the way that her Villanova shirt pressed out that she had a nice rack. I would later learn she was a full 36C. Her shirt was dark blue, with white lettering, and her gray shorts gave an ample view of her sexy legs. She looked around, and our eyes met. Walking over confidently, she extended her hand, "Will Collett I presume?" I grinned and shook her hand firmly, "Should I have brought flowers? This feels like a blind date." She laughed, and rolled her eyes, "God, I hope not. They are always so painfully awkward." I liked her instantly. She ordered a drink, and we made small talk while waiting. I learned that she was a rising senior at Villanova, majoring in pre law. She was from Ohio originally, and loved playing field hockey, but knew that this upcoming season would be her last chance to play on a serious level. I told her a little about my time in the Army, but not too much. I kept admiring her while we talked, trying not to be too obvious. I think she noticed my wandering eyes, but she never said anything. She was just a really cool girl, the kind that you can hang out with at a ballgame, but also take out to a fancy event. I was bummed to hear she had a boyfriend, but he was off in New York for the summer, interning at some Wall Street firm. She went over some of the procedures for walking the dogs with me in the Starbucks. Carolyn's plan was for me to shadow Kayla this week, and then head out on my own the week after. Kayla had been working for Carolyn part-time for about a year, so she knew the ropes quite well. I rode shotgun in her old Pathfinder as we drove out into a rather nice part of Paoli. The house was nestled on a quiet, shady cul-de-sac. It had a large, fenced in back yard, with an amazing pool, and pool house. The client's dog was a nice German Sheppard named Hans. We let him out back, and threw a ball around, letting him get his exercise. I kept admiring Kayla's body as she picked up the ball, and threw it to the other side of the yard for Hans. There is no doubt that she caught me checking her out, and she became a bit more flirtatious as time went on. I walked over to the edge of the pool, admiring it, as Kayla rounded up Hans. She walked up behind me, and said, "Isn't this place amazing?" Grinning, I looked at her, "This would be a hell of a place for a party." She smiled back and said, "Hell yes, but since I like my job, I don't think that would be such a hot idea." Being a bit of a smartass I replied, "And I thought you Villanova girls knew how to party." With that she stuck her tongue out at me, and headed back inside. She showed me how to complete the company's form, which showed the time we arrived, and left, and what we did with the dog. It also let you mark when you fed him, and gave more water. Overall, the process wasn't hard, and after shadowing Kayla for a few days, I got the gist of it. I decided that she was a very cool girl, and that it was a shame that she had a boyfriend. Under different circumstance I probably would have made a move, but I figured that with my luck she would slap my face, and tell Carolyn, thus ending my young career as a dog walker. But just hanging out with her was a lot of fun. After the fourth day she told me that she would show me how to complete the final paperwork when the job was done. The clients would be home Saturday morning, so out last visit would be on Friday night. Feeling a bit bold I said, "Why don't we meet for a drink before hand, my treat of course." She paused for a moment, and said, "Yeah, why not?" I suggested that we meet at a bar in downtown Wayne, have a drink or two, and then head over to the house for the final appointment with Hans. Kayla agreed, and as we walked out to our cars, in front of the Paoli house, she smiled at me, "I do think Carolyn will be pleased with how quickly you picked things up." "Does that mean I get your seal of approval?" I asked coyly. She grinned back at me and said, "Without question". And suddenly I could not wait to meet her on Friday night. With that I got in my car, and headed back home. My parents were out of town, yet again, which meant the house was all mine. I went out for a run, jerked off in the shower, and crashed around midnight. The next morning, I woke up early, and went out for a run. It was a hot, steamy day, and I was soaked by the time I got back home. There is a pool in our backyard, so upon returning home I went straight to it, peeling my shirt and shoes off, and jumping in with my running shorts still on. The water was refreshing, and after a few minutes I got out, and sat on one of the chaises to dry off. I could hear some commotion on the other side of the fence that separated our house from the Thompsons, who lived next door. I looked over, and could see the brim of a tan sun hat bobbing along the fence. I grinned, and thought to myself, it must be Mrs. Thompson. Here is the backstory on Mrs. Helen Thompson. She, and her husband, David, had been our next-door neighbors since before I was born. They had two sons, a little older than me, who no longer lived in the area. David was some executive at a pharmaceutical company in Philly, and Helen had always been a stay at home mom. As far as moms in there fifties go, Helen still held it together quite well. I always had a little crush on her growing up, but as time went on I sort of lost interest. That is not to say that she isn't sexy, far from it. Standing just about five feet, six inches, she has dark brown hair that falls just below her shoulders. Her complexion has a nice olive tint to it that goes well with her brown eyes. Her breasts are large, and natural, and always caught my eye. She has curves, but holds them well. I had spoken with Helen a few times since being home, but nothing more than simple pleasantries if we saw each other outside. I wasn't really in the mood to be social, so I quietly got up, and headed toward the house. I got just to the back door, when I heard her voice, "Will?" I looked back at smiled, "Mrs. Thompson, how are you?" She shook her head and smiled back, "When are going to start calling me Helen?" I stood there, still a bit wet, in my shorts, and grinned, "Probably never". She was wearing a simple, white, V-neck t-shirt, and khaki shorts. Blue gardening gloves covered her hands, and sunglasses covered her eyes. I couldn't tell if she was checking me out, but it seemed like her gaze was focused right on me. "Where are your parents?" She asked. "Oh, they are out town for a few weeks, up at the place in New Hampshire". "Ah, how nice for them! They've got you holding the fort down, huh?" I grinned, "Yeah, I guess they trust me not to throw any wild parties". She laughed throatily at that and waved her hand at me, "Well, I will keep quiet if you do, just keep it down after midnight". I smiled, and tried to head back inside, as the small talk was getting boring, when she said, "I was wondering if you could do me a favor?" "Um, sure, what is it?" I asked, not really wanting to do any chores for her. "Well, normally I wouldn't ask, but David is in Houston all week for work, and I have this big, heavy pot that I was hoping to move from the garage to the back patio. Would you move it for me? I will throw in a free lunch if you do". She asked so nicely that of course I said yes. I told her I needed to change, and that I would be over in a few minutes. So I went inside, put on an old Army t-shirt, and blue lacrosse shorts, and walked over to her garage. She had the door up, and was standing near a large, gray concrete pot. It was huge, to say the least, and fucking heavy. I managed to lift it, and carry it to the patio, although I needed to stop and let it down a few times. Finally I got it to her desired spot, and am not ashamed to say that I was breathing hard afterwards. "Oh, thank you so much Will!" Helen cooed as I stepped away from that behemoth. "I usually have one of my sons do it, but they haven't been home in months." "Oh, no worries." I said, although my arms and back were burning from lifting it. I am not kidding, that thing was really fucking heavy. She motioned for me to come in, and made me a nice sandwich for lunch. We made more small talk as we sat at the island in the center of their big kitchen. I couldn't help but check her out from time to time, thinking that I would certainly not kick her out of bed. Her breasts were pressed nicely against the white V-neck. It was a very flattering shirt on her. After we finished I thanked her for the meal, and headed back home. About thirty minutes later I realized that I left my cell phone in her kitchen. Cursing to myself I went back up her driveway, hoping that she was still home. Her BMW was still in the garage, which was open, so I let myself back in. The downstairs area was quiet, and I found my phone, right where I left it. I turned around to head back out, when I noticed the sound of water running through plumbing. I walked out to the foyer, and could hear a shower running upstairs. I instantly had a vision of Helen, naked in the shower, and my cock started to stir. I started to head back out again, when suddenly I became very bold. I am not sure where it came from, because trying to make a move on Helen was a bad idea. She was a close friend of my parents, and lived next door, so if things went badly there would be no escaping her. That being said, I found myself walking up the stairs, past all of the Thompson family pictures. I paused at one of Helen, with her husband, taken at some formal event. She looked radiant in a blue evening gown, and he looked dapper in his tuxedo. Mr. Thompson had always been nice to me. His company had great Phillies seats, and he would often take me, and his sons, to games when we were younger. I paused for a moment as I thought of his generosity, but continued upstairs anyway. All is fair in love and war after all. My heart raced as I walked down the hall to the master bedroom. The door was open, allowing me to see the large king size bed inside. I peeked in to see if Helen was visible, but the room was empty. Draped on the bed was a pretty blue dress, which she had obviously laid out to wear after her shower. I entered the room, my heart still racing, and began to undress. Again, let me say that I am not normally so bold when it comes to women, and to this day I am not sure what came over me. Perhaps it had been my recent romp with Carolyn, which had led me to believe that I was irresistible. Any sane person would have said that my actions were stupid, and I would agree with them. Yet at that point in time it seemed like a perfectly good idea to strip naked in Helen Thompson's bedroom, and open the door to the master bathroom. Upon doing so I found myself in a large room, with a big shower stall in the far corner. Helen's white t-shirt, and shorts, were in a pile on the floor. Beside them was a simple, yet very sexy, white bra and panty set. I caught a reflection of myself in the mirror, my hard cock swaying as I made my way towards the shower. Helen's back was to me, and she was humming a song quietly as she bathed herself. I paused for a moment before pulling on the shower door, and then went for it. "Mind if I hop in?" I said, as I stood naked at the door. Helen literally jumped, and turned around to look at me, her eyes widening at the sight of me standing there, totally naked. "Will!" she gasped, "What, what the hell are you doing?" She tried to cover her breasts and pussy as best she could, but her hands were too small. She looked magnificent, and her breasts were even bigger than I imagined. Her eyes were wide, but I couldn't help but notice that they were glancing down at my erection. I grinned as I walked in, "Making my move, obviously". I closed the door behind me, moving towards her. Helen backed against the wall, her eyes still taking me in, her hands still feebly trying to cover her body. "You need to get out of here, now!" She said. At first I thought, oh fuck, what have I done? She is about to scream rape, and call the police on me. But as I moved closer, her eyes became fixed on my cock. Standing just inches apart I smiled at her, and rubbed the back of my hand over her cheek. "Helen, I think that you are incredibly sexy, and have always fantasized about being with you. My time in the Army taught me that life is short, and tomorrow is never guaranteed, so here I am." It was a cheesy line, but it seemed to do the trick, as she lowered her hands, revealing her big, natural tits. She looked back up at my eyes and said, "Will, I am married, and your parents, I mean this is wrong on so many levels." I smiled and leaned in, kissing her softly on the lips. At first she did not react, but then she moaned quietly and kissed me back. My hands gently ran up and down her sides, as my cock brushed up against her right leg. After a few seconds I broke the kiss, "If you want me to go, I understand". She looked at me for a long moment, and I could see the wheels turning in her head. Finally she broke out in a small smile as her hand went down to my cock, rubbing it gently. Game. On. "Well, its like you said Will, life is short, and God knows David doesn't touch me much anymore". As her delicate fingers gently rubbed up and down my hard shaft. "That is a fucking crime", I said as my hands went to her breasts. Let me say that for a woman of her age, her tits were lovely. They were a natural 38DD, with a little bit of sag, but nothing to sneeze at. Her areoles were a dark brown, with nipples that were the size of pencil erasers. Those nipples got progressively harder as my fingers began to play with them. I leaned down, kissing the tops of her breasts as she continued to stroke my cock. I swirled my tongue around each nipple, which earned a louder moan from Helen, "Oh God, yes, suck my tits! Mmmmmmmm". She placed her other hand on the back of my neck as I moved my mouth back onto her right nipple. I sucked on it loudly, which she loved, then sank my teeth into it. "Oh Jesus! Yes, I love to have my nipples bitten!" as her hand stroked my cock faster. The hot water of the shower sprayed against us as I went to town on her massive breasts. This woman had tits that did not quit, and I gave them the attention that they so sorely missed. I pressed her back against the tile wall, and mashed her breasts together, kneading them with my hands as I kissed her again. This time she kissed me with greater urgency, and allowed me to slide my tongue into her mouth. As we made out against the wall, I dropped one of my hands down between her legs, finding her clit. I began to rub it in small, gentle, clockwise circles, which led to her moaning yet again. I kept this motion up as I resumed suckling her big tits. We embraced like that for a few minutes when finally she pushed me back, and slid down to her knees. Her sexy brown eyes looked up at me as she stroked my cock, which was just inches from her face. "Will, I had no idea you were so big" she said while winking at me. "Well, I did drink my milk growing up". I said as she rubbed her hand up and down my shaft. "I can see that. Mmmmmmmm. Mind if I have a taste?" She said in a very sexy tone. "I insist!" I said. With that she slowly kissed down one side of my shaft, and back up the other, before slowly sucking on my swollen head. The sight of her lips stretched over my mushroom head was a sight to behold, and one that I will not soon forget. She slowly began moving her lips further, and further down my shaft. Going down a little farther each time. I noticed that her free hand slid down to rub her pussy while she stroked my cock with the other, moving her lips in time with it. It was an incredible blowjob that only got better as she took me all the way in her mouth. "Fuck!" I moaned as my cock hit the back of her throat. Her eyes just beamed up at me as she sucked my cock like a porn star. Who knew that this proper, conservative woman gave such great head? She picked up the pace with her mouth, sucking and slurping loudly as she went to town. I rolled my eyes back, loving the sensation as she polished my cock properly. I could feel my cum building as she took my cock all the way in her throat again, but I did not want to cum in her mouth. Not yet, anyway. She must have read my mind, because she pulled off and stood back up, kissing me deeply as I wrapped my arms around her. Without saying a word I turned her around so that she faced the wall, her hands planted against it. I bent her over so that her big tits swayed over the shower floor, and her big, heart shaped ass was placed right in front of me. I stroked my cock as I spanked her ass playfully with my other hand. She looked back and grinned at me as I did so. Spreading her ass cheeks wide, I rubbed my swollen cockhead over her pussy lips. I rubbed it up and down quickly, pressing just the tip inside her to tease her a bit. She looked back and grunted at me, "Stop teasing me, and put that big dick inside me!" I am not one to deny a woman, so without hesitation I gave her what she wanted by thrusting my cock deep inside her hot, wet pussy. She jumped at the sensation, her pussy gripping me as it took me all in. "Oh God! Damn, that is sooooo good!" She moaned. The Main Line: Doggie Style Ch. 01 With my hands on her hips I began to slide my cock in and out of her, fucking her with a slow steady pace at first. I would let my cock go about half way out of her dripping pussy, then thrust it back in. Every so often I would spank her ass, which soon had bright red spots on it. The sound of my wet hips smacking into her was quite audible in the tiled shower stall. The sight of Helen Thompson bent over in front of me was absolutely surreal. This was a woman who used to carpool with my mom to take me, and her sons, to soccer practice. Somehow that made fucking her even hotter. I picked up my pace, slamming into her harder, and faster. Her large tits swayed back and forth as my cock plunged in and out of her. I put my hands on her shoulders, pressing her harder up against the tiled wall. This allowed me to fuck her from a new deeper angle, which she seemed to greatly appreciate. "Oh God, that is so good!" She moaned as I plowed into her. I could feel the cum starting to rise up my shaft, and I knew it would not be long before I erupted. I was fucking Helen like an animal now, ramming into her as hard as I could. "Oh Will, oh yes, ohhhhhh!" with that Helen began to cum hard, the waves of her orgasm washing over her body. The sensation of her climaxing put me over the top. I buried my cock deep inside her, and exploded, filling her with my hot seed. It was an intense orgasm, and my body quivered in absolute pleasure. As we came down from our orgasms, I pulled out of her, stepping back. The sound of the water spraying down suddenly seemed very loud. Helen looked at me sheepishly, and walked out of the stall, grabbing her towel to dry off. I rinsed off quickly, admiring her body as she dried off. She wrapped her white towel around her body, and threw me another one as I stepped out. She watched as I dried off. I was not sure how to read her. Was she glad that just happened, or did it just dawn on her that she cheated on her husband? The question was answered as she walked out of the bathroom, and into the bedroom. Turning around she motioned for me to follow her with her finger. "I have a party to attend at seven, but until then my schedule is wide open." With that she dropped her towel, once again exposing her sexy body, as she crawled into her marital bed. I smiled as I finished drying off, tossing my towel on the floor. I crawled on top of her, kissing her deeply. Needless to say we made the best of our time.