Dear Sweet Dee

by Thesandman

Caution: This Sex Story contains strong sexual content, including Consensual, Reluctant, True Story, First, Oral Sex, Anal Sex, Masturbation, Petting, Sex Toys, Squirting, .

Desc: Sex Story: Memories of another time, another place finally revealed

Her name was Darlene Dimpledale, which is perhaps why she'd gone by the name Dee Dee, or simply Dee, for about as long as I'd known her. Which by now had been a very, very long time indeed.

My parents and I had lived next door to Dee and her husband Frank for years. I was an only child, and as I came to find out early on, Frank and Dee Dee never had any either. Though the reason for that was something I never found out as to why. But as such, Dee had taken to me as a second mother of sorts, always inviting me over for milk and cookies, and then later on when school was out for the summer, watching out and taking care of me. Something my mother was very appreciative of, as she and dad both had to work back then.

I didn't mind it at all either. Even as young as I was back then, I had a secret crush on Dee Dee, though the feelings I had back then weren't any I could really put my finger on as to why. I just liked her for some reason. Though perhaps it was because she was such a great cook, better than mom was, though I'd certainly never once told her that. But she was a great baker too. Always making pies, cookies ... cakes. I found myself preferring to hang around with her during the day, more so than running off to play with friends. At times, she actually shooed me outside in order to force me into doing so, rather than hanging around with her all day.

And then Frank died. It was for a time one of the saddest times I'd ever been through. I had come to think of them as a surrogate Aunt and Uncle, even going so far as to call them that. It was a period of several long lonely months that Dee just seemed to withdraw into herself, and perhaps even age a little bit faster in the process. At most, she was only a few years older than my own mother, but I saw her begin to take on the look of a run down, lonely woman in a very short period of time.

I had just turned sixteen when Frank passed away.

It was now time to give back after all those years she had looked after, and taken care of me. With mom and dad's full approval of course, I continued to spend as much time as I could helping her out around the house. Doing odd jobs, mowing the lawn, raking up leaves, taking the trash out, whatever she needed doing, I was always Johnny on the spot. Never once did I feel obligated, put out, or put off in having to do things for her, no matter what they were.

Gradually, she slowly started to act like her old self once again. She'd even began putting on makeup again, something I hadn't seen her do in a very long time. She had even dyed her hair, taking out the few strands of grey she'd allowed to remain up until then. The moment she did that, looking ten, if not fifteen years younger again. Now even looking younger than my own mother was.

By the time I had turned seventeen, only one year away from graduation now, we'd gotten into such a place of comfortable familiarity with one another, that I had found myself being able to talk to her about things, subjects I could never discuss with either mom or dad. Sometimes they were personal things, and later as I'd actually started dating girls, they became even more intimate in nature. It happened so gradually, so smoothly that never not once did I think either one of us was uncomfortable or really embarrassed because of it. Dee became a sounding board for me, offering advice, and even at times, a few related personal experiences of her own time growing up as a teenager. It was nice, not to mention interesting, getting a perspective on things from a woman's point of view. I think it helped me understand girls a hell of a lot more than most, though even in understanding, it didn't always help me cope with the difficulties of raging hormones, or the adolescent silliness of growing up. For myself, or the girls. Dee just sat acting amused, remembering perhaps, and then would sit down and talk to me about it.

Like I said. I almost preferred spending time with her as opposed to spending it with any of my friends. Such was our relationship. And then one day, something profound changed things, and set things on a whole new course quite unexpectedly.

I had recently turned eighteen, graduation was only a couple of months away, and though it was my intention to further my education, I was also seriously considering entering into the service. I had a lot on my mind at the time. Decisions to make, and another one that I hadn't as yet told anyone about. Her name was Marjorie. My girlfriend. We'd been dating of course for well over a year now. Things had quite naturally progressed in the 'curiosity' department for both of us. Though Marjorie had told me early on, that she was saving it for when she got married, or baring that ... only for sure if she felt like she had found the man she loved would she consider taking it that far even before marriage. Marjorie and I had spent the last weekend in the front seat of my car going far beyond anything we had ever done up until then, just short of actually having intercourse, "going all the way" as we called it. It had been the most exciting time of my entire life up until then. But it had also left me wondering as well. Marjorie had hinted at the fact that she might..."might" she had said it twice, have a big surprise to give me on my birthday. Well, not quite on my birthday as that was in the middle of the week. But very possibly on the weekend after that. A weekend in which her parents were going to be away. The implications of that, without coming right out and saying it ... were obvious.

I was nervous, excited, apprehensive, curious ... and scared to death. And when I went over to mow the lawn on Saturday morning, Dee could see that something was bothering me and invited me inside. It had actually been a long time now since we'd just sat down and talked the way we used to do. Busy life, schedules ... trying to grow up had naturally put some distance between us. But even with all that, we still had a smile to share, or a friendly word or two to give one another every time we saw one another. But again, it had been a long time since we'd just sat down together and had a nice long comfortable chat.

Unfortunately, I knew going in, as did she ... this wasn't going to be one of those. Even though we both sat smiling at one another just like old times.

"Ok Jimmy," she began..."Spit it out, what's going on?"

By now of course I went by Jim. No one, and I mean no one called me Jimmy any more. Even mom had quit calling me by that name the day I turned sixteen and informed everyone ... mom and dad especially, I wasn't a little boy any more, and that Jim, not Jimmy was the name I would answer to. The only one who did ... still did, and who could honestly get away with it was Dee. To her, I'd be Jimmy no matter how old I was.

It was as though Dee knew my thoughts before I did. Just like the time I'd gone into my father's workshop looking for some nails for a clubhouse the other guys and I were building. For years there'd been this one cabinet that dad had kept locked, and his one and only warning to me back then had been to "Stay the fuck out!" I knew he was serious, because dad never said 'fuck' unless he meant it. So I had ... until that very moment. Reason being, I noticed the lock wasn't actually locked. It had been left hanging open. I stood there staring at it, wondering what secrets existed behind that "fuck-lock" as I called it. But being the curious teenager that I was, I opened the cabinet, and then just stood there staring at it.

"Why on earth would dad feel it necessary to lock up a bunch of old dirty rags and service and maintenance manuals?" Standing there peeking in, that's initially all I could see at first. Until I raffled through a few of the books on the stack. Suddenly I knew why. It was a stash of dirty magazines. I certainly knew mom would come unglued if she knew dad had these, which is partially why he kept them out here in the shed of course. But the fact he even had them to begin with was an eye-opening moment for me. Dad wasn't the prude I'd always thought him to be. I quickly rummaged through the stack, glad that mom and dad were at work so I didn't fear anyone coming up on me while I was flipping through a few. Selecting two that I found quite interesting, I hurried back outside to where my friends stood waiting for me.

"Hey Jim, where's the nails?" Bob Petersen, my best friend and buddy asked me curiously as I shielded the books against myself, running towards them. His eyes suddenly opening wide when he saw me doing that. "Hey man ... wha'd ya find?"

"Inside!" I said blowing past everyone. Though we still had some finishing work to do yet, the clubhouse for the most part was nearly finished. We'd even dragged in an old worn out couch and a chair as part of the d├ęcor, which I immediately plopped down in, holding the books out for everyone there to see. There were five of us in total, now sitting around passing the books around as we took turns quickly leafing through them.

"Fuck!" Bob said actually slipping his hand down inside his pants. "I'm getting horny!"

Don't laugh ... it was the first time I'd ever heard the word. "Horny? What the hell's that?" I asked, though delighted to find out, I wasn't the only one that didn't know what it meant.

"This!" He exclaimed taking his hard swollen cock out, and immediately began jacking himself off. I too had been masturbating for a while now, as had we all ... but never together, and certainly never in front of one another, or even admitting to one another that we ever did. But Bob being Bob, and basically the leader amongst us continued to do so, all the while looking at the magazines.

.... There is more of this story ...

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