My First Crush Ch. 01

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A favor for my best friends Mom turns into something special.
4.9k words
4.53
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Part 1 of the 2 part series

Updated 11/01/2022
Created 06/26/2009
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After that amazing afternoon with my mom I honestly believed I couldn't top how I was feeling at that point. That was until I read the note mom had left for me on the counter in the kitchen.

Dear Son,

You know I love you, and that I REALLY LOVE our special affair we've been having together. But now, I would like to you do me a really big favor...

Do you remember your friend Mike from school a few years back? Well I ran into his mom about two weeks ago at the store and we decided to catch up on old times together over lunch.

She seemed like her old self except for that old spark she always used to have. It took a little persuasion on my part, but I was able to find out from her that she and her husband have been having problems since their son had gone off to school. He didn't seem to be interested in her anymore and it was like they were two strangers living in the same house.

When she mentioned she was planning on going through her house and getting rid of some of her old stuff while her husband was away for the weekend, I thought of you, and what you might be able to do for her. I'm not asking you to do this unless you really want to. But if you can show her half as much, as you've shown me, in that the passion is still alive inside her, then maybe we can give her back something she thinks is lost forever. Love Always, Mom.

After reading her note, I began to recall the great times I used to have over at Mikes place when we were kids. I never really thought much about his mom Judy until I saw her come in from the office one day wearing a soft summer sweater that hugged her body showing her small waist and generous breast held tight by her clothes. She had the most amazing hourglass figure, with her hips being just a bit wider than her shoulders. To finish it off she wore a white pleated summer skirt with smoky brown hose and white peep-toe heels. She always had the darkest collar length hair I had ever seen, not too short, with soft waves that framed her delicate face.

Being just an early teenager at the time I couldn't help but notice her as she moved about the kitchen, her heels clicking on the floor getting dinner ready as Mike and I sat at the table working on model cars. Needless to say, I found more reasons to head over to Mike's house after that day until they decided to send Mike off to a private school about a year later.

Still remembering her phone number I decided to give her a call to make arrangements for this weekend. She seemed genuinely surprised to hear from me after all this time and we made arrangements to get together on Saturday morning to do a little attic cleaning.

Saturday morning started out cool, but with lots of humidity with the temperature climbing into the 90's. Arriving at Judy's place I didn't know what to expect as I knocked on her door. The place seemed the same, just like it had looked years before, even the same smells. I felt myself feeling a little nervous as the door opened and I found myself looking into the eyes of the woman I had had my first crush on years before.

She looked great and the years had been pretty kind to her. Wearing only a loose t-shirt and shorts I could still make out the outline of her body as she invited me inside. "Well Hey Ron! Boy it's been a while since I've seen you at my front door big guy! Come on in and we'll get started right after we eat some breakfast. I hope you're hungry."

The smells of coffee and breakfast hit my senses and I immediately found myself starving for some home cooked food. Following her upstairs to the kitchen I couldn't help but watch as her hips swayed as she literally bounced up the stairs in front of me. "I saw you pull up and I was just getting things ready for us to eat so we could get an early start before it got really hot," she added.

Sitting down at the table I was treated with a layout of eggs, bacon, hash browns, toast and coffee.

Conversation seemed to center around getting caught up from when we had seen each other last and how her son Mike was doing in school. Towards the end of breakfast I figured I'd let her know a little of what mom had relayed to me earlier.

"You know, I spoke to mom the other day and she told me about what you two had talked about at lunch a few weeks back," I mentioned. At this she just looked out the kitchen window and off into space as she sighed and began to try and stop the tears that were filling her eyes. "How much did she tell you?" She asked. "Enough to let me know that you needed a little help and maybe someone to talk to," I answered as I reached out and took her hand in mine.

"I just don't know what to do!" she whispered, "He seems so empty now after Mike left. It's just not the same anymore between us and I just don't know if it's my fault or something else. He just won't talk to me!" she added as she strongly squeezed my hand with hers. Looking up at me she just smiled softly as she began to get up from the table. "I'm sorry but you really don't want to hear the ravings of a lonely women now, do you? Maybe we should get started on the attic before it gets too hot to work up there," was all she said before she walked out of the kitchen leaving me alone at the table.

The rest of the morning went pretty quietly with us moving box after box out of the attic and down into the garage. By the time lunch rolled around we were both pretty much covered in sweat as we sat in the garage and surveyed our work. Judy had been going through boxes deciding on what she wanted to keep and what she wanted to give away. Most of it was old stuff that didn't mean much, so it all went into a pile in front of the garage to be taken out later. I was helping pull boxes open when I made the most amazing discovery.

One box had been labeled work stuff, but when I opened it, I found myself looking down at the most intimate collection of high heels I had ever seen, all neatly wrapped in small plastic bags to keep them from getting wet or damaged in storage. I never did recall ever seeing Judy wear any of these before when I used to hang out here, so my curiosity got the best of me.

"Hey Judy, what do you want me to do with this box?" I asked.

Coming over and seeing what I had discovered only caused her to smile from ear to ear as her face lit up with memories.

"Work Stuff?!" I asked, smiling... She just smiled back at me and reached into the box taking out a pair of white high heeled stiletto pumps. "Yea, work stuff" she giggled. "I don't know if I ever told you, but I used to do some modeling before I started having kids. But that all changed when Mike came along and I had to become the so called, responsible parent, as my husband used to say." I could feel her sorrow as she began to put them back into the box.

"Why don't you see if they still fit," I suggested, as she stopped and just looked at me. "Go on, try them on... I bet you look pretty hot wearing these!" I added.

"Yea, I'm hot, hot and sweating like crazy," she quietly spoke as she began to laugh. Looking up at me she could see that I was totally serious in my suggestion as I patiently waited for her to make a decision.

"Ok, why not!" she said as she began pushing her small tennis shoes off her feet. "They probably don't even fit me anymore anyway," she added as she slid her feet into the soft white leather.

Reaching out for my arm for support, she stood there in front of me with a look of surprise on her face as she discovered that they fit just as well as they had years before. Taking her first steps around the garage I watched as she quickly got used to the four inch heels again as her confidence began to build. "I can't believe I still remember how to walk in these!" she commented.

Looking back at me from across the garage she started smiling as she slowly walked back towards me, a gleam in her eye as she firmly planted each foot and gently swayed her hips.

"I can see that I still draw that same look and reaction from a man when I wear these, even if I am wearing shorts and a sweaty t-shirt," she commented quietly. I too could feel that same reaction as my arousal and desire began to grow.

Taking them off she quickly dropped them back into the box saying, "Well, it's getting pretty hot so maybe we should call it a day." Saying this she placed not only that box, but several others with the same markings near the door to the house. "Are you sure you don't want me to help you out with the rest of these?" I asked.

"No, I can take it from here and you've been plenty of help as it is, and I don't want to waste your whole Saturday."

"It's never a waste Judy," I answered as I headed for the door with her following. As I turned around she quickly reached up giving me a big hug and kiss on the cheek, lingering there as she whispered, "Thanks again for the help and the great company."

Heading back to my apartment I was still wondering what might happen next, if anything. It didn't take me long to find out.

Monday came and my boss and his assistant were busy showing the contractors what they wanted to have done on one of the buildings that needed some remodeling. So to help out, I was recruited to assist them with anything should they need a hand. It didn't take long when I got a call on the radio to come to the office.

Not knowing what to expect as I walked in to the secretary's office, I was confronted with an incredible sight. My boss was sitting at his desk talking to someone as his assistant quietly informed me that she was a possible new tenant. They were both really busy with the renovations and wanted to know if I could possibly show this lady around the complex to give her a chance to see if she liked any of the units. "No problem," is all I could say as they came out of my boss's office. My jaw just about hit the floor when I realized who the new tenant might be.

Here was Judy, all dressed up in a form fitting white business suit, a long white skirt with soft smoky brown hose, and her tall white stiletto heels. I just kept staring at her as the assistant handed me the keys. "Take as long as you want Miss," my boss added as we headed out the door. Walking across the parking lot to the first building I couldn't help but stare at her body as she walked next to me, her heels clicking on the pavement with the contrast between her hose and her white heels keeping my attention. She seemed to be enjoying the moment as she innocently asked me "So, do you like living here?"

"It's pretty cool, I like the arrangement I have with the manager for a free place to stay while I help with the maintenance work. I see you took my advice and decided to keep the heels," I added.

"How couldn't I...!" she exclaimed. "After seeing your reaction to me the other day in my garage. The look you had on your face made me curious to see if it was just my imagination playing tricks on me, or if you really did enjoy seeing me walk around in my heels."

"I can see from your reaction now, that I was right in my assessment," she whispered, as she wrapped her arm around mine. "You do look pretty sharp there Judy, I whispered as I leaned closer to her, smelling her perfume.

"In fact, I used to have this big crush on you when I used to come over to your place to hang out with Mike," is all I could say before she quietly interrupted me. "Could you show me something out of the way and a little more private if you don't mind?"

Taking her arm I guided us over to the far side of the complex where there were several furnished town home style units. As we walked inside Judy made it look as if she was really serious about renting the place, taking the full tour around the main floor before she slowly began walking towards the stairs that led up to the bedrooms. On her way she walked past the front door, locking it and securing the chains, as she turned to me and commented, "We really don't want any interruptions, now do we?"

"No, I guess we don't," is all I could say before she pressed her body into mine and began strongly kissing me and pulling my shirt open, running her hands across my chest. "So, you had a crush on me did you? Was it an infatuation kind of crush, or was it something more? Maybe even something a little naughty?" she asked as she continued to tear my shirt open.

"It was such a turn-on seeing you dressed up in heels," I breathed between her soft kisses.

"My, aren't you just tanned so nicely" she commented as she began to kiss and gently bite at my nipples on my chest causing me to jump back a little. Pulling her head up we began to really attack each other as I tried to unbutton and remove her blazer. As she ran her nylon covered leg up mine I reached down and began running my hands up her thighs and under her skirt saying, "I've always dreamed of doing this with you Judy, ever since I saw you that first time!"

"Then why don't you take me upstairs and show me what you've always wanted to do to me!" she softly spoke as she began sliding up the railing. Moving up behind her I wrapped my arms around her waist and pulled her to me, holding her there and smelling her soft hair as she struggled in my arms. "We'll get upstairs in a minute, I breathed, but right now I think we'll try out the couch first."

Lifting her off her feet I carried her over to the couch setting her down gently. As she stood with her back to me I began unbuttoning her blazer from behind, my hands shaking as she continued to run her hands over my arms.

Letting it drop to the floor my fingers found the zipper on the back of her skirt and it too found its way to the floor, sliding down off her body and falling around her ankles and heels.

Standing there in front of me in just her white satin body slip she looked striking with her jet black hair, her tall white heels, and creamy soft skin. I could see and feel her trembling as she began to question whether or not we should be doing this. "I don't know if this is such a good idea," she kept repeating.

"What does your body tell you?" I asked, standing behind her as I ran my hands over her hips and up her stomach coming to rest on the top of her generous breast gently rubbing and massaging them into arousal.

"I want this so bad!" she finally breathed as her hands joined mine forcing me to squeeze and gently pull her breast through the cool silky satin.

"Then let me please you Judy," is all I said as I started running my tongue around her ear and gently began sucking on her neck and the top of her shoulder. She responded by pushing herself back into me, grinding her hips against me and softly whispering, "take your clothes off, hurry, Please!"

Stepping back and literally ripping my pants and shirt off I came back up behind her, my shaft coming into contact with her satin slip as I pulled us together once more.

"Oh my, you have grown up haven't you!" she rasped as she continued to grind her ass back against me.

Reaching down I picked her up in my arms and placed her down on one end of the over-sized couch. Looking down I couldn't believe how hot she looked at that moment as I began running my hands up her legs.

Feeling the soft nylon under my fingertips and parting her legs as I moved up and over her body, I began moving my hands under her slip when I discovered that she had not worn pantyhose as I had hoped, but something more fitting, real stockings with white lace garters.

"All the better," I breathed as I began pushing her slip up over her thighs and around her waist.

As I leaned down to tease her soft pussy she tried to pull me up whispering, "No! nobody has ever done that to me before, not even my husband."

"So then it'll be an adventure for the both of us," I answered as I leaned back down and gently began running my tongue up her thigh. She stiffened at first as I neared her pussy, her body shaking and her hands firmly holding my head.

As I continued to slowly move up her thigh over the tops of her stockings she actually tried to stop my advance. "I don't know if I can do this!" she rasped.

"It's Ok Judy, just relax and go with it. Trust me." I whispered as I pulled her towards me and slowly slid my tongue all the way up her wet slit coming to rest at the very top. "OOOHHHH" she softly yelled out as her body tensed.

Making small circles with my tongue I began to feel her relax as her legs slowly parted for me.

"OH Yes!" she hissed, "I had NO IDEA it felt like this," she moaned as she slowly began moving her hips against my circling tongue. "We're just getting started," is all I said as I pushed my tongue gently inside her, tasting her arousal and causing her to jump in my arms. "Put your heels onto my back Judy, open yourself up to me," I whispered.

As her hips rotated up off the cushions I continued my expansion of circles around the lips of her pussy, using my tongue and fingers as I gently increased the speed and pressure on her. As my fingers began pushing inside I could feel her start to squeeze them as her orgasm began to build, her moans increasing as she let herself go to the sensations.

As I ran my fingers down and her anus, teasing her, as she began to really moan out loud. "Keep doing that!" she kept whispering, "It feels so good when you do that."

Digging her heels into my back she pushed herself up to meet my probing tongue. "Do you want me to stop?" I asked, pausing for a moment. Her answer was her hands pushing my head back down into her as her body took on a life of its own. "Push Harder on my ass, Harder!" she breathed.

"Don't stop, please, just don't stop!" she rasped as she moved faster and faster against my mouth and fingers. Placing my mouth over her clitoris I gently started sucking and massaging her with my tongue as my fingers slid down and made small circles over her anal opening. Her moaning became one long and ever increasing yell as her orgasm rocked through her body, her juices flowing around my fingers adding to ease my fingertips as they moved over and then into her now inflamed pussy.

Not wasting time I moved up over her, kissing her as I lowered myself down onto her body as I started pushing my shaft deep inside. Still reeling from her first orgasm she just laid there for a moment as I started moving in and out of her with long slow deep strokes, feeling the heat of her pussy around my shaft. Looking down into her face I softly whispered, "Do you want me to stop now?"

Reaching up and wrapping her arms around my neck she pulled me down into a powerful kiss as I continued to thrust into her, her breast still covered by the satin slip pressing into my chest between us, and her pussy squeezing and contracting around me as I moved in and out of her. "God, I just love your body Judy!" I moaned as I pushed in as far as I could, her legs moving against my sides and her heels gently digging into the backs of my thighs.

"Then take it!" she answered as she ground her hips into mine. Pushing her body down into the cushions I started powerfully thrusting into her, holding her tight in my arms as my body took control of my senses.

"That's it, That's it, I'm yours for the taking now!" she rasped as I began thrusting furiously into her, hearing her softly yelp each time our hips came together.

Wrapping her legs around my waist and pulling me into her she quietly whispered in my ear, "Please cum inside me!"

Pushing into her hard and deep I felt myself explode, pouring my seed deep inside her, feeling it burn as her pussy clamped down on my shaft with a force I had never felt before. "God I love what you do to me!" she whimpered as she clawed at my shoulders pulling me into her.

We just stayed that way for a while as our breathing settled down, my shaft slowly softening inside of her as she kept moving against me, gently squeezing me. "I had no idea it could be like this," she continued as she ran her fingers through my damp hair. "I hope you loved this as much as I did," I quietly whispered.

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