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My Friend's Hot Mom, Chapter 1

"Tommy was asked to look after his best friend's Mom... and he took the job seriously!"

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Famous Story

Brian had been my best friend for several years. We had gone to school together since we were in sixth grade together. 

Brian and his mother lived a couple of houses down at the end of our dead-end street. We were inseparable since the day we first met and our folks used to call us "Pete and Repeat" because where one was, you could be sure the other wasn't far away. 

We went to school together and took a lot of the same classes. It made for a reliable study partner and we helped each other make it through school all the way until we graduated. 

We helped each other through our individual girlfriend crises–Amy and I broke up and Paula broke Brian's heart. 

There were a lot of good times, and some bad times along the way. Brian's folks split up one year and it took a toll on him. But he knew he could count on me to help him through it and we both leaned on each other over the years.

However, the fall after we graduated high school, "Pete and Repeat" had to take separate paths. You see, he was going off to college while I was unable to. He got a grant to study biology, his favorite subject in school, and I was going to head into the job market and see what I could do to make a living.

The day before he was due to leave for college, Brian and I were at his place, lounging around the pool. "Tommy, I have a favor to ask of you. It's a pretty big favor too, so be prepared," he said, looking right at me.

Since he didn't usually ask for favors like this I knew he was serious. "What is it, Brian?" I asked, sitting up.

"Well ever since Dad took off on us, it's been just Mom and me here. And now I'm going off to college. I don't know if I'll be able to come home next summer or not, I'll just have to play that by ear and see. 

But I'm worried about Mom being here all by herself. I know you aren't going off to college and you'll be around–would you look after her while I'm gone? You know, stop over from time to time and see how she's doing and if she needs any work done around the house? 

I know you are pretty handy with home repairs and fixin' stuff. She might need someone to do some things around here," he said.

"Sure Brian, you don't even need to ask. I'd be happy to stop in and check on your mom. And you can give her my phone number in case she needs anything in between times. Don't worry about it buddy," I said.

The thing is that Diane, Brian's mom, is hot–I mean smoking hot, and she knows it, too. She always wears provocative clothes, you know tight t-shirts with no bra, short shorts, barely-there bikinis, and dresses so short they would have to stretch to be mini-dresses! 

All the clothes that show off her long legs, tight ass and big tits. She is a tease and a flirt and she loved to make men drool over her.

About a week after Brian left, Diane called me and asked me to come over. I wasn't doing anything that day and I went right over, eager to see this hottie and what she was wearing that day. 

She didn't disappoint either, she was wearing a sleeveless tie front crop top and her short shorts (cut so high she almost couldn't wear any underwear!).

"Hi Tommy, come on in. Want a glass of tea or something honey?" she asked. She made us both a glass of iced tea and we sat down at the kitchen breakfast bar.

"Tommy, I wanted to ask you if you would like to make some extra money this summer. I know Brian has asked you to check up on me and I like that you come over and help me out. But I'm talking about something more than that. 

"You see, I've been wanting to put up a storage shed... one of the pre-cut, build it yourself from a kit kind, and I was wondering if you'd like to do it for me. 

"I was going to hire a company to do it, but if I can give you a little business and save some money at the same time then I'd rather do that. 

"I know you are pretty handy with tools and I'd feel better having someone I know around the house than a bunch of strange construction men," she said.

Of course, I said yes to the job for a few good reasons. She offered me good money. Money I could use since I hadn't found a job yet. Plus, she said she would get whatever tools I needed and I could keep them afterward. 

Also, and more importantly to me, it would give me an excuse to be around her house for three or four weeks, which to a horny eighteen-year-old was a very big perk! I'd had a pretty big crush on Brian's mom for several years and I wasn't about to pass up any chance I could get to be around her.

Diane suggested I start working on the first of July and I agreed. She ordered the kit and I made a list of the tools and supplies I would need to do the job. I had most of them already but I did need a few painting supplies and a few other things.

About a week before the kit was scheduled to arrive, I started going over every day. I had to layout the concrete footings and plan out how the shed would sit on the property. 

Diane wanted the shed to be able to hold the yard tools, the pool cleaning equipment and some other things that never seemed to find a home. 

There was also going to be a small carport type affair on one side that she could store the riding lawnmower in so it would be out of the elements.

Every day I showed up at her house, Diane was wearing something scandalous–either an oversized t-shirt or man's white shirt with nothing else, or her ridiculously tiny bikini, or some hot lingerie that would make a Victoria Secrets model blush. 

Diane did love to flirt and tease; she loved wearing clothes that no adult should wear, except her. I could almost swear she was taunting me to take her, even though she had always dressed like this. 

It was something I believe irritated her jealous ex-husband to no end, but only made me want her all the more!

Anyway, as I left she said, "I'm really looking forward to having you here helping with this project, Tommy. I think we could have a lot of fun with it."

"Me too," I nodded, not realizing the subtle innuendo her words carried.

She smiled her dazzling, knee-buckling smile, and added, "But be careful, it's supposed to be pretty hot out all next week."

"I will dress properly," I said.

She winked and smiled coyly, "I'm not sure I will."

That night as with most nights, I dreamed about my best friend's mother and all the things I would do to her if I ever worked up the nerve. Being young and still quite naive in the complexities of seduction, I wasn't entirely sure of Diane's motives. 

Was she simply toying with me and teasing a horny young man just for the thrill of being able to, or was she actually trying to tell me something? I knew I had to be careful, Brian was my best friend and I didn't want to come on to his mother unless I was positive that was what she wanted. 

It was a dangerous situation and I had to be sure before I made any kind of move. I didn't want to be too forward and act out of line, but I also didn't want to pass up a once in a lifetime opportunity either!

I arrived as scheduled at eight the following morning. Because I was over at her house so much these days, she had given me permission to just come in without knocking.

"Ms. Baker?" I announced myself as I slowly opened the door.

"Come on in Tommy," Diane said. She was sitting at the breakfast bar dressed in her short silk robe, her long lean legs exposed and crossed. I walked up to her and got a good view of her ample cleavage. 

I thought for a second about just tugging that robe open and devouring this woman–the object of my greatest dreams–right then and there. But again, I had to be sure I had read the many signs of her interest in me right; it would be humiliating and potentially friendship ending if I was wrong.

"Do you want some breakfast, honey?" she asked.

"Oh, no thanks, ma'am, I already ate before I came over," I said.

"Okay then, and it's Diane," she said. "There's no need to be so formal, sweetheart. How about a cup of coffee then?"

"Okay, Diane, a cup of coffee would be nice, thank you," I said.

We sat and talked a bit about the project and she told me she would be here all morning but that she may have to leave for a bit that afternoon. She asked me what I would be doing that morning.

"Well, I have most of the foundation work done and there are just a few more things there. Then I guess I will start laying out the floor joists and subfloor. Once I get that done, I guess I will start working on building the walls," I said.

"It all sounds too complicated for me, but I guess you know what you are doing. I'll leave you to it then," she said.

I went out back where the supplies had all arrived the day before, and I began working. I was a couple of hours into it when she came out to check on me. Dressed in her miniscule two-piece bikini that showcased every curve of her perfect body, my cock instantly woke up in my shorts.

"How's it coming, Tommy?" she asked.

I ignored her play on the word 'coming', even though my natural smart-ass had a hard time leaving an opening like that alone. 

"It's coming slow and steady," I said.

"I was going to go for a swim. You can take a break and join me if you like," she said.

"Not at the moment, maybe later though," I said. I knew if I did get in that water with her, I would be done for the day.

"Okay, but if you change your mind…" she said. I nodded, watching her turn around and dive fluidly into the pool.

I spent the next half hour constantly distracted, while nearby the most beautiful MILF in the world made like a mermaid, swimming tantalizingly close to me. 

A couple of times she came over to the edge of the pool closest to where I was working and propped herself up on her arms on the side watching me. 

The way she watched me and seeing her wet hot body, it's a wonder I didn't smash my fingers with the hammer! Damn that woman knew how to work it!

Finally (and mercifully) she decided to get out of the pool and she grabbed a towel. "You look hot, Tommy… would you like a lemonade?" she asked, smiling flirtatiously.

"Sure," I agreed. I actually was quite thirsty, but more importantly, I wanted her to come back outside with me. While she was making our lemonade, I took off my shirt to show off my very toned upper body.

I worked for a couple more minutes until she returned with our lemonade. "Looking good," she said. Diane was still in her bikini although it had dried almost completely now.

"How can you tell, it's just a few pieces of wood scattered about?" I joked.

"I wasn't talking about the shed," she said, handing me my glass and holding onto it a little longer than necessary. She smiled that beautiful, perfect smile then turned and went back over to the pool, and sat on a lounge chair.

Reluctantly, I went back to work. I had been working for about twenty minutes, when Diane called, "Tommy, could you be a dear and come give me a hand for a moment?"

"Sure, be right there," I called back, wiping my hands on my shorts and going over to her.

She was applying suntan lotion to her legs and arms when I reached her. She asked, "I'm trying to work on my tan. Would you mind putting some lotion on my neck and back?"

Would I mind? I thought, Hell this was every teen boy's fantasy! Putting lotion on a hot, sexy, half-naked MILF like Diane–I've masturbated to less!

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She handed me the lotion, rolled onto her stomach and I sat down beside her. "Could you also undo my bikini top? I don't want any tan lines to show when I wear my dresses."

I wondered what kind of dress she would wear that such a tan line could be seen but then I remembered this was Diane Baker, a woman who dresses the least amount of clothes she can get away with! 

"S-sure," I said like any horny young boy would. And with shaky hands, I pulled the strings of her skimpy bikini top.

The bikini top easily fell aside revealing the sides of her very full and voluptuous breasts. Ms. Baker had been blessed with a very bewitching pair of 36DD breasts which I had always found very hard to ignore! 

And now these beauties were nearly naked in front of me! Half of me wanted to just go for broke right then and there and see if all her flirting and sexual double-speak was just that–talk–or if she was actually willing to back up her taunting and teasing with actions.

The other half was still playing it safe and cautious; these people were good friends and I didn't want to cross some unseen border just because I misread some perceived signal. 

So I decided that I would play along for a little while longer and see where this took us. I figured I could adjust my reactions according to her lead. 

I did have a sense that the inevitable was close, and that we were definitely headed towards something more than a "working" relationship.

I took the bottle of lotion from her and squirted a good glob onto one hand. I split the glob into both hands and put them on her back.

"Oooh! That's cold!" she said, startled.

"Sorry! It'll warm up in a second," I said.

"Well, rub me down and warm me up then," she said, again with her sexual undertones. I thoroughly covered her neck, shoulders and back with lotion, massaging gently while I did. 

She let out a soft moan as I moved lower, to just above her ass. Her moan made me feel like maybe I should press this seduction thing we had going a little further.

"Aren't you worried about tan lines down here too?" I said, plucking the bottoms of her bikini up a bit.

"Should I be?" she asked back, playfully.

"I dunno, I was just asking," I countered, in a feeble attempt to play her game, "I'm not really sure what the proper bikini tan line rules are, to be honest."

"Well it's better safe than sorry–tan lines can be pretty serious social breaches!" she said giggling. 

She lifted up her hips, surprising even me. I watched in awe as she tugged the strings and uncovered her tight, firm ass.

"Agreed," I barely got out. My fantasy MILF was now naked in front of me!

My already hard cock was straining against my boxers and jeans, begging to be released and put into play. 

And although I was ordinarily a fairly confident guy and never had any trouble talking to or being around the girls I had known, I felt my hands trembling as I poured lotion on her ass and began rubbing it in. 

This was my every fantasy come true, and I made sure to lotion her whole ass and down her thighs a bit. I wanted this to last and to burn into my memory... it would make excellent dream material!

As I was about to finish she said, "Be sure to get my ass crack too, Tommy–I'd hate to have a tan line there."

"Yes, that would be awful," I replied, as I coated my fingers and put some lotion between her ass cheeks. I was so tempted to slide my fingers further between her ass cheeks and explore her all the way to her back door. 

Or attempt to "accidentally" slide my fingers to brush against her pussy in the small window that existed between her legs just to gauge her reaction… I could always claim that the lotion made my hand slip. 

Even though I couldn't really see her pussy, I did have access to it if I could just get up the nerve to take the risk.

As I thought about all the things I wanted to do to my best friend's mother, she ended the brief moment of teenage fantasy.

"Thanks, honey," she said, snapping me back to reality.

"N-n-no problem," I stammered.

I stood up, stared at her naked beauty briefly, and returned to work, adjusting my cock as I walked.

For the whole next hour, I worked and tried not to spend too much time staring at the naked perfection, lying there shining like an angel as the sun reflected off her magnificent oiled body nearby.

Around noontime, she put her bikini top and bottom back on, and wordlessly went back in the house. I kicked myself for never getting a good look at her rack or her pussy. 

I figured a woman like her probably kept it shaved or at least trimmed in some sexy fashion, but I really wanted to see it for myself.

The sexual tension between us was already at a fever pitch and this was just the first morning. It seemed obvious (at least to me, that is) that we both wanted the same thing. It was just a matter of who would take the first step. 

And so I worked the next hour relentlessly, trying hard to concentrate on what I was doing instead of what waited just inside that sliding glass door… 

I was just getting ready to go and pick something up for lunch when she came back out, now dressed in a stunning red stretch-knit dress that looked like it was painted on her! It was about mid-thigh length with a deep plunging V front that went down to the silver sequined belt and scooped out back that made me realize that tan line issue was a real problem for her! 

She wore five-inch metallic-silver heels and, shocking in that day's heat, nylon thigh-top stockings… a particular favorite of mine.

Although she was always a beautiful woman, I loved how she often wore nylons while in the house, even under her jeans.

"I'm heading out for a little while," she said as she came by to check on my progress.

"Okay," I nodded, asking, "But isn't it a little hot for stockings?"

"Isn't a little too hot to be wearing a shirt?" she countered.

I laughed, "Well, I just put it on a couple of minutes ago. I was about to go and get a bite to eat and most restaurants have that whole no shirt, no service rule."

"Such a pity, having to cover all this," she said, playfully running her red painted fingertips across my chest, "Oh well, enjoy your lunch. I'll be back in a couple of hours. I left my cell number on the kitchen table in case you need anything."

I stood there speechless.

"And I do mean anything Tommy," she repeated, stressing the word 'anything'.

"O-okay," I said when I remembered how to speak. The chess game of sexual seduction continues…

I watched her walk away, her hips swishing seductively. Damn that woman looked good even walking away! I left a couple of minutes later to go to lunch.

When I came back from lunch, Diane wasn't around. So I just went right back to work. I didn't see her again for the rest of the afternoon until I was finishing up at around five. 

I went inside and saw she was reclining on her couch, still in her stockings with her toenails painted red to match her hot fingernails, as she watched TV.

She turned around, hearing me, and asked, "Are you done for the day, Tommy?"

"Yeah, I think so," I answered, still focusing on her long legs and pretty feet.

"Why don't you take a seat, then, and visit with me for a bit?" She offered, moving those long legs off the sofa to make room for me next to her.

"I'm all hot and dirty and sweaty… I don't want to ruin your white sofa," I said.

"I bet you are," she quipped, the words dripping with sexual implication.

"I need to take a shower," I admitted.

"I think I have one of those upstairs if you like. Then we can visit," she smiled playfully.

"The one upstairs in my room has better water pressure. You go shower," she ordered, "and I will order some food. I hate eating alone and with Brian gone now… it gets awful lonely around here."

Her offer was too good to reject, and the likelihood of something happening later was growing greater by the moment, so I agreed.

"Sure, although I don't have any clean clothes."

"I'll get you some," she said, You and Brian are about the same size, his stuff should fit you well enough."

"Okay, I won't be long," I agreed.

I went to her room, and into the bathroom. I got undressed and jumped in the shower. I wasn't in there more than a minute or two minutes when I heard the door open and close and her voice. "Like the water pressure?" she asked.

I froze, ironically I was lathering my cock at the moment. I finally said, "Um… Y-yes, it's very powerful."

"It's all steamy in here, you must like it hot," she quipped, her every word dripping with flirtation.

"Yes, I do, the hotter and wetter the better," I responded, not being able to see her making it easier to flirt back.

"So do I, honey," she said, as she shocked me by joining me in the shower.

My hand still wrapped around my cock, I again froze… I was now starring at my very naked MILF fantasy! Diane Baker, the girl of my dreams, was standing in the shower before me, completely shaven and even more perfect than I had fantasized!

"Is that for me?" she asked, looking down at my fully erect and still sudsy eight-inch cock. "It's even bigger than I thought it would be."

I couldn't talk. I was frozen stiff like I was made of stone. I wanted to say something witty like I would to any of the teen sluts I fucked and often dominated, but I was completely speechless.

"Since I didn't hear a no, I'll just take it as a yes then," she smiled, dropping to her knees and taking my cock in her hand.

I gasped… my long-held fantasy was finally coming true!

As if reading my mind, she looked up at me and asked, "I bet you have fantasized about this moment for a long time, haven't you Tommy?"

I stammered, "Y-y-yes."

Well, to be honest, I have too, Tommy," she said.

"You have?" I couldn't believe what she was telling me! I was her fantasy as well?

"Mmmhmm… Now let's see if I can make both our fantasies come true," she said, as she leaned forward and took my cock in her mouth.

I groaned, "Ohhh fuck!"

I had never had sex in the shower before, but watching her bob up and down on my cock as water sprayed on us was incredible.

Unfortunately, the surprise of my fantasy finally coming true, and her mouth such pure perfection, I lasted just a couple of minutes before I warned her, "I'm going to come."

She popped me out of her mouth just long enough to say, "Yes, baby cum for me. Give me that sweet cum! I want to taste you!" and then she wolfed my cock back down resuming her exquisite sucking.

She bobbed up and down on my cock even faster and took all eight inches of my cock down her pretty throat. It was too much and I spewed my load into her eager, hungry mouth. 

She didn't slow down until every last drop was deposited. Once done, she stood up and licked her lips, saying, "Mmmm, young man cum! What a delicious appetizer!"

Before I could speak, she got out of the shower and added, "I left some clothes on the bed for you to put on."

"Uh, thanks," I said, bewildered by what had just transpired and by the fact that just as quickly as she had joined me, she had left.

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Written by Master_Jonathan
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