tagMatureThe Main Line: Doggie Style Ch. 01

The Main Line: Doggie Style Ch. 01

byMainLiner1903©

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.

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