Neighborhood MILF Hunter Pt. 03

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My first encounter with a mature woman.
8.6k words
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31.7k
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Part 3 of the 4 part series

Updated 06/10/2023
Created 06/13/2021
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I guess it's time to tell the story of how I wound up in this neighborhood, let alone how I came to concentrate on middle aged women rather than the young girls most of my co-workers chased. I grew up in the upper class part of a medium sized town. Our home was nestled amongst the other high priced homes, the ones that held the doctors, the bankers, and the lawyers. My father was in the last part, the lawyers. I was a typical teenager, without much direction in my life, and when I started my junior year of high school he said he wanted me to take over the law firm.

While being a lawyer didn't necessarily appeal to me, I didn't have any other ideas, and the money would be great, so I decided there was no reason not to try that out. I was in my freshmen year of pre-law and on my way to Florida (we always spent it at our beach house there) when I got the phone call.

My father's law partner was on the phone. I had known 'Uncle' Bob since I was a kid, and he had the sad duty of breaking the news that my parents were gone. They were planning on flying my father's plane down and meeting me there, but an accident on takeoff had resulted in both their deaths. To this day I still don't remember the trip home after that. The following days were a blur as well. A double funeral to plan, relatives flying in, the wake, the service and finally the burial. It was six months later when I finally woke up in my bedroom and was able to start thinking about what was next.

During this entire time I was alone. I had no female in my life. I had lost my virginity in high school to a classmate, and the less said about that fumbling encounter the better. I had dated in high school and college as well, but had grown tired of the young girls. Don't get me wrong, I had plenty of girls chasing me, but not for me, but my parent's money. I was smart enough to realize that. I stand about six feet, and I'm in fairly decent shape. Brown hair and brown eyes completed a rather non-descript package. So while I had my fair share of dates, the moment they started hinting about meeting my parents was the time I started ignoring their phone calls.

It was easy to pick out the gold diggers. They were either willing to give it up on the first date in hopes of sucking me in or became the 'good girl', kisses and light petting only, cock teasing me, hoping I would give them anything to get into their panties, including an engagement ring. I gave up on dating college women all together when I was in the bathroom at a party and I overheard two girls talking without knowing I was listening. They were discussing how Cindy, my date, had been the biggest slut on campus until she had set her eyes on me. One of them actually said how sorry she felt for me, knowing that as soon as Cindy got her MRS degree that she was sure to go back to her philandering ways. They were shocked when I walked out, but not as shocked as Cindy was when I dumped her in the middle of the family room and walked out on her and the party.

But this was the here and now, and when I woke up in my old bedroom that morning, I looked around the room at my stuff and suddenly felt out of place. This house was entirely too big for me, and everywhere I looked I had once happy memories turned to bitter loss. It just didn't feel like home anymore. I realized that it was time to sell it and move on. Bob Foster, my father's law partner, was the executor of the estate, and I called him that morning.

"Hello. Davidson and Peter. May I help you?"

"Good morning, Peggy." I had known the kindly elderly female that was their receptionist and head of the office staff for years.

"Good morning, William. It's good to hear from you. How are you holding up?"

"Making it day by day."

"I know. It's been just as hard on us here at the office. I guess I don't have to tell you how much all of us here loved your parents."

"I know. Thank you. Is Uncle Bob in?"

"Sure. Let me transfer you."

A few seconds later Bob Peter came on. "Hey, William. How are you doing today? Is there anything I can do?"

"As well as can be expected, and as a matter of fact there is. I'd like to talk to you about my parent's house. I'm thinking about putting it up for sale. There are too many memories here."

"I understand, and I don't blame you at all. Frankly, with the way the market is, I think it would be a good time to sell."

"Thanks, Bob. Look, I'll be honest, I don't have a clue about real estate. I could really use your help. Do you have a recommendation?"

"As a matter of fact, I do. Her name is Heather Carlton. I trust her implicitly, and if I was selling my house she'd be the one I'd call. We've handled her legal business for years. Why don't I call her and set up an appointment for you? What's your schedule today?"

"I'm going to the gym this morning, but I have no specific plans the rest of the day."

"I understand. I think this is a positive sign that you're ready to start moving on. Let me see when Heather can come out."

"Thanks, Uncle Bob."

"Hang in there, buddy. Call me if you need anything."

"Hey, I'd like to thank you one more time for keeping Dad's name on the firm, you didn't have to do that."

"Your father was the one who started this firm and he's the soul of it. It stays there as long as I have anything to say about it. Take care buddy, and I'll give Heather your contact information."

A few minutes later I got a text from her telling me she'd be there at 1PM. I acknowledged it and left for the gym.

I came home feeling as close to normal as I had for quite a while. A good workout had seemed to purge a lot of the stress out of me, and I was almost cheerful as I grabbed lunch and got dressed. Dress pants and a nice shirt, along with a pair of casual boat shoes seemed to be the best thing to wear. It was 1PM on the dot when the familiar chimes of the doorbell rang.

I opened the massive front door and immediately recognized the woman on the other side. My mom had been friends with Heather Carlton and when I saw her I immediately recognized her from when she had visited our home before. This woman was an absolute knockout, and I had to make sure to keep my mouth shut and avoid drooling in front of her!

She was a few inches shorter than me, barely weighing more than 120lbs, and she wore long, blonde curls, framing a face that was eager and cheerful, a professional smile gracing her face. Bright red lips matched her long red nails, above which on her left ring finger perched a massive engagement ring with a matching wedding ring. She wore a short black jacket under which her 38DD's strained against a white blouse that was almost sheer, clearly showing the outline of her bra underneath it. She had a black skirt that swirled knee length around two beautiful legs in nude pantyhose, ending in three inch black stiletto heels. I saw the light of recognition in her eyes and the smile became more real.

"William, what a pleasant surprise! It's so good to see you!" She immediately came inside and gave me a hug, which it was only polite to return, and her light, sexy perfume tinkled my nose and stimulated my cock to show the first signs of life in weeks. I was shocked when she gently kissed me, not on my mouth, but close enough!

"My, how you've grown up! Your Dad was so proud of you!" She released me, and stood there beaming.

"Hello, Mrs. Carlton."

"Oh please, William! Call me Heather! We're both adults, and you look like you've developed into a fine young man!" She ran her eyes over me, with evident approval, and continued, "And a very handsome one as well!"

I blushed and she giggled, resting one hand on my arm for a moment. The soft touch definitely stimulated parts I had not thought of for quite a while, and I looked at Heather again with a new eye. There was no doubt that this was a very mature, very sexy woman, and I was beginning to have some very impure thoughts about her.

She walked across the tile of the entrance, her heels clicking on the marble floor, and we went into the main room.

"Of course I used to come over here when your parents would entertain, but that was as a guest, and not as an agent. Naturally I've never been upstairs either. Could you show me around, please?"

"Certainly! It would be my pleasure."

She smiled, showing me all of those perfect white teeth, and I grinned back. I held out my arm in the old fashioned manner, and she quickly grabbed it with both hands, holding it tightly.

"You look to be in really good shape. Bob mentioned you went to the gym this morning." She ran one hand up and squeezed my bicep, and a look of approval came over her as she felt the firm muscle there.

"I try to stay in shape."

We walked into the kitchen, and she broke away to start looking around, complimenting me on the neat, clean appearance, and opening up various cabinets. Was it my imagination, or did she seem to be stretching up to look in the top cabinets just a bit more than necessary, showing off that fabulous bust of hers? A couple of times she knelt over to look in the bottom cabinets, once showing off that still tight ass and seeming to inadvertently lift her skirt in the process, showing me a tantalizing glimpse of the top of her pantyhose and those beautiful tanned thighs.

We made our way through the rest of the house, and there was no doubt she was swinging her ass just a bit more than normal. The curve of her hips seemed to invite me to spread my hands across them and draw her close, but I manfully resisted the temptation. We went upstairs, and I thoroughly enjoyed watching that tight ass sway up the stairs ahead of me, and catching a glimpse up her skirt. She got to the top and looked back at me, and I could almost swear she gave me a tantalizing wink when she caught me staring at her lovely body.

I must have been mistaken though, because there was no way such a beautiful, delectable, mature married woman such as her was going to go for a young guy like me. I swallowed a lump in my throat and we walked down the hallway. We went through all the rooms, and I listened to her compliment the master bedroom and bathroom. There was no doubt she was fully confident of her ability to sell it when I was ready to put it up for sale.

We went back downstairs and sat down together on the sofa in the family room. My eyes were irresistibly drawn to the sight of those long, beautiful, toned legs, encased in pantyhose, with her stiletto heels. I quickly looked back up to see her gazing at me with an inquisitive look on her face. She quickly became all professional, but I could see a spark in the back of her eyes.

"So, what are you thinking?"

I was flustered for a second. "About what?"

She smiled, and her smile was more personal then the professional one she'd greeted me with, with a glint of mischief.

"The house, silly." She touched me lightly on the arm, and my arm tingled where her hand had been. "What kind of price are you looking for?"

"Frankly, Mrs. Carlton..." I stopped as she flashed me a warning grin, and I continued, "Heather," she smiled, "I don't know anything about real estate. I've never bought or sold property before. What do you think I ought to be asking for?"

She promptly said, "Whatever you can get!" and giggled. She continued in a more serious tone. "Listen, William, this is a great property in a great neighborhood. I don't think you should ask for less than $650,000 dollars."

I sat back weakly. "I had no idea it was worth that much."

Heather smiled at me and again patted my arm, her hand lingering just a touch longer than it should. "I might be able to get you even more than that. Let me do some research and get back to you. Is this your correct email address?" She showed me a piece of paper with my contact information on it and I nodded. "Good. Now, where are you planning on living?"

I shook my head. "Frankly, I hadn't even considered that far ahead!"

She smiled. "I'm not surprised. You're focused on selling, while most buyers are focused on buying. I'll tell you what. Why don't we meet this weekend? You don't have anything planned, do you?"

"No." I continued bashfully, "I don't have much of a social life."

"Why not? I'd think the girls would be lined up asking you out!"

I blushed and ducked my head, then looked over at her. Her soft blue eyes were warm and inviting, and her small smile invited confidences. I shrugged my shoulders. "Most of the girls my age want my Dad's money, not me." The thought of my Dad sent a wave of pain through me, and as I closed my eyes I could feel Heather's arm go around me, her hand on my back, as she pulled me close and softly hugged me. "I don't know if they like me for me, or the money," I finished.

She let go of me, and we both sat up. "I understand. Most girls your age are shallow, only looking out for themselves. You need someone more mature."

I smiled at her. "Most mature women that I would be interested in are married and off the market."

She smiled at me, laughing gently, and lightly popped my arm. "Why William Davidson! Are you making a pass at me?"

I blushed. "No," I said unconvincingly. The truth is that I had been making a gentle pass at her, despite her being married.

It was obvious that she wasn't upset, and was actually flattered by the thought.

"Well, since you have no social agenda, why don't you come out to this address on Saturday. I'm holding an open house in a new neighborhood that's just been built. You could have your pick of the houses." She gave me a sly wink as she handed me a card. "I think you'd really like the neighborhood."

I looked at her inquisitively but she would say nothing more. Within a few minutes she had left and I was looking forward to Saturday a bit more than I thought I should be!

After my work out and run, I showered and changed and drove over to the address on the card. It was a pleasant subdivision with about a hundred houses scattered about tree covered roads with sidewalks. I must admit I was impressed, and the prices were reasonable. I admired how the builders had built around the mature hardwoods, leaving plenty of trees in yards and along the streets.

What really caught my attention though were the women! It seemed good looking women were everywhere I looked, working on lawns, walking down the sidewalks in groups, and especially sunbathing and playing in the very large community pool next to the clubhouse. That was where Heather had set up her open house, and I swung into an empty parking spot and walked inside.

I went inside, saw Heather and my mouth went dry. It was a good thing she was engaged in conversation with another couple right then, because I would have sounded like a babbling idiot! She looked incredibly hot just standing there. She was wearing three inch heeled black stilettos with nude pantyhose, that showed off those perfect legs of hers. The yellow dress she was wearing came down to just above her knees, and it was tight enough that I could catch a glimpse of her panty line. It also did an excellent job showcasing that tight ass of hers. It accented her hips, and then showcased her beautiful bust. She had to be at least a Double D, if not larger! Her makeup was expertly applied, highlighting her best features. Her fingernails were dark red, the same color as her lipstick, and I had a sudden image of her small hand wrapped around my cock as she jacked me off. I could only put it down to a long dry spell!

She saw me and called out, "William!" She walked over and gave me a quick, tight hug, enough to enjoy the momentary sensation of those magnificent breasts pressing into my chest. She again kissed me just off my mouth. She held onto me and held me at arm's length for a moment. "Don't you look nice today!"

"Thank you, Mrs. " I stopped at the warning smile, "Heather! If I may say so, you look absolutely gorgeous today!"

I got a wide smile and blush for that rather forward compliment, and she said back, "You can always say so when you say sweet things like that!"

"I'm just telling the truth."

She smiled again. "Aren't you the sweet talker!"

"Glad I'm telling the truth then, because I can say it with a clear conscience!"

She smiled again, and that sparkle was back in her eye. "Did you look around the neighborhood?"

"Yes, I did. I like it a lot."

"I imagine you liked the women around the swimming pool as well?" she said with a devilish grin!

I blushed and she grinned. "What? I may be married, but I can still remember what it was like to be young and have guys like you chase me."

I don't know what came over me, but I shot back, "As far as I'm concerned, I'll chase you right now all you want!"

Her eyebrows rose, and I felt my stomach drop at the thought I'd offended her. I felt a wave of relief come over me when she blushed and mumbled, almost under her breath, "I may just let you catch me!" The only thing that stopped me from taking that thought a bit further was a young couple walking into the room and Heather quickly breaking away from me, seeming almost flustered.

While she greeted and talked to them, I browsed the various home plan brochures laid out on the table. One of them stood out to me, a three bedroom, two bath on a full basement. It was a two story house with a bit more living space then I really needed, but it had a nice set of porches, front and back. I also liked the downstairs office that would be easy for me to convert to a library. I always have been a reader.

When Heather made her way back over to me, she casually placed her hand on my shoulder, almost squeezing it in what appeared to be a casual way. I was well aware of it, along with her running it down my arm and gently squeezed my bicep. My nether regions were starting to react very strongly to this very attractive MILF! But still, she was married, and I didn't dare take it any further. Otherwise she was standing perfectly for me to slip my arm around her waist and pull her close.

"So, did you find a house you like?"

"I like this floor plan, here."

She leaned forward and looked at it. "Ah, yes. We have several of those. I'd suggest the one in the cul-de-sac. It's roughly in the center of the subdivision. Do you want to take a look at it?"

"Love to."

She found the keys on a key board and just as we were walking out to her SUV several cars pulled up. She looked visibly upset. "Here I was looking forward to taking you on a private tour and it never fails!"

I smiled at her. "It's okay. I'll run over and take a look and come right back."

She pouted for a moment, then smiled. "Well, okay. I hope you like it!" The professional smile was back as she turned to greet the new arrivals, and I got in my car and drove over. The house was at the rear of the cul-de-sac, with a green strip behind it and trees to either side, granting me a measure of privacy. I did a walk through and quickly decided that I liked the place a lot. Standing on the terrace out back, I could imagine myself relaxing here with an adult beverage and a willing female in the seat next to me. It must have been coincidence that I imagined Heather sitting there dressed in a way that left little to the imagination!

I was driving back and passed the pool, naturally thinking of Heather in a bikini (damn I was seriously in lust for this woman!), when I remembered the lake house. We, or my parents actually and now mine, owned property on a lake in middle Georgia. It was an unusual cabin, in that it was on an island in the middle of the lake. Most islands in the reservoirs were undeveloped, and I didn't remember how Dad had gotten his hands on this one, but he had, and he had built a nice cabin. We used to go out there every summer.

When I got back to the clubhouse and walked into the meeting room, Heather was talking to another older couple. She broke away and came over me, but was obviously in a hurry. "Well?"