Dear Sweet Dee


Author’s note: In the telling of this story, for obvious reasons, all names, places except for the time frames as noted have been changed/disguised to protect the confidentiality of everyone involved in this story. And please note for content of the story, all persons are 18 or older.

* * * * *

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 canlı bahis şirketleri 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 décor, 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 canlı kaçak iddaa magazines.

It was after when I’d gone over to Dee’s to finish moving some things out of the house she was donating to charity that we had our first real serious discussion. I was abnormally quiet perhaps, a little withdrawn in a way, still struggling with what had happened earlier in the day inside our clubhouse.

“Sit down Jimmy…talk to me. What is it that’s troubling you anyway?”

Like I said in the beginning. Dee might have been older than mom by a few years, but I didn’t really look at her that way. We were friends more than anything else. Close friends, the kind of friend you could say anything too. At least that’s the way Dee had taught me to believe with her. She’d kept secrets, confidences in the past. Maybe it hadn’t been over anything quite this intimate, or “naughty-bad” as I now thought of it…but I still felt like I could trust her, not even being embarrassed about telling her what I’d found, and then what the guys and I had done while looking at the magazines together.

In a way…it was almost a relief to see the small knowing smile on her face as she sat there until I had told her everything. Every single detail without interrupting me even once.

“So what’s the problem?” She asked. “You feeling guilty? Bad you did that?”

“Well yeah…sorta,” I answered back.

“Good! You should feel guilty! For disobeying your father and getting into his cabinet, whether it was locked or not! But not for doing what you did with your friends afterwards,” she said a bit more softly. “It’s perfectly natural Jimmy,” she told me. “Everyone does it…including me,” she’d added, though the workings of that escaped me for the moment. But she continued before I could ask her a much more personal question, sidetracking me perhaps…wisely. “If you’re feeling guilty about masturbating in front of your friends, or them doing the same in front of you…don’t be. It’s a perfectly normal, natural curiosity that all young men go through, even if most of them never admit to it. So don’t go beating yourself up for it. If anything, enjoy this time of self-exploration, learn about yourself. And don’t rush things either…you’ll learn all about girls soon enough.”

That however had been the conversation that had opened the door. After that, we talked openly, candidly about anything and everything. Whenever I had a question, or had heard something…I came to Dee and asked her. And I honestly have to say, I came away each and every time with an honest and complete answer. Dee never once held back, told me what it was I wanted to know, didn’t go overboard, never gave me more than I’d asked, nor more than she felt I needed to know at the time to satisfy my curiosity or question.

Such then became the nature of our relationship. Dee became the best friend I ever had.

It was like going back in time. Dee sat waiting for me to do just that. Spit it out. Normally, or rather in the past I’d found it easy to do so. But it had after all been a while. Would she still be as receptive as she once was? Would I shock her by what I was considering, dealing with? I realized even as I asked myself that question, the answer was no. Not Dee.

“I think Marjorie wants to have sex…you know, intercourse, this weekend…tonight,” I said running everything together…spitting it all out so to speak.

“I see. And what do you want?” She asked me point blank. “Do you want to have sex with her? And if I may ask Jimmy…are we talking about losing our virginity here if you do?”

Oh she was indeed the wise one. She had always asked things in such a way that it forced you to honestly think about them before answering. Giving her an honest answer in return, especially as she’d always given me one.

“Yeah, I do. I mean…well, we’ve sort of done everything else but that,” I freely admitted to her, doing so without reservation, though I did notice she raised her eyebrows just a little upon hearing that. “And yeah…we both are,” I added then, though hearing the reluctance in my own tone of voice upon hearing myself say that.

“You’re not ready. Not even now,” she said equally as soft, but yet a bit more firmly. “If you were Jimmy…you wouldn’t be hesitating right now. If Marjorie is the right girl for you, and I’m not speaking about waiting until you get married before you decide to do that. Heaven’s knows…Frank and I certainly didn’t. And I didn’t lose mine to Frank in the first place. I lost my virginity to a man older than I was, who knew what he was doing, and to whom I will forever be grateful.”

“No shit? Really?” I asked, forgetting my manners for a moment as I had hardly ever sworn in front of Dee before. Luckily, she laughed it off though, not even chastising me for the obscenity.

“Yeah, but I was ready. I knew it was what I really wanted, even though I knew there was no future in it for he and I. That’s not what it was about for me. And it shouldn’t be canlı kaçak bahis for you either. If Marjorie’s the one…she’ll wait. Just as you should. If she isn’t…well, then you won’t be looking back on this moment years from now and wishing that you really had waited. You want my advice Jimmy?” She asked. Which she always did. Just like that. And then she waited, never offering, never giving it, unless I honestly and truly wanted to hear it. And for sure…this time I did.

“Yeah, I would Dee. I really, really would.”

“You said you’ve done everything else. Can I assume from that, you’ve pleasured her orally?”

Ok, don’t laugh. I obviously still had a lot to learn here. “Her?”

Though she did. “Yes Jimmy…her,” she chuckled a bit. “I take it, she’s pleasured you that way, taken your cock into her mouth, sucking it.”

I had seriously forgotten how candid she could be with me. I guess most would have thought she’d have used the more clinical term, “penis” when describing that particular male appendage. But…she’d said cock in front of me before, and pussy too. So hearing her say that didn’t exactly set me back on my haunches. Now…hearing her say, “sucking it” did. That was indeed a sex thing, a describing what you do…or wanted to do, or did sort of sex thing…sex act. But I sat there asking myself the question, suddenly everything else no longer important to me. “Had she?” Obviously she must have, but it wasn’t exactly something you normally sat there and pondered over. Until now.

“Ah yeah…she has. And ah no…I ah…I ah, haven’t,” I stammered just a bit, finally admitting to her I hadn’t reciprocated in that way. Though to be perfectly honest about it, the subject of my doing that to her…for her, hadn’t exactly come up either. Obviously…we hadn’t done just about everything. There were still a few things. Well…a whole bunch of things actually, we hadn’t done.

“I see,” She said again sitting back in her chair, rocking a little, that same knowing bemused smile on her face. “So tell me Jimmy…have you?”

“No.” I said easily, honestly…and sincerely. I never had. Never even thought about it until that very moment. And perhaps to some, when that moment came, they’d think about it, wonder about it, hesitate, and maybe even, find it disgusting or a revolting thought. But not me. I sat there, not realizing I was actually becoming aroused, not just yet anyway, though I was. But my mind was lost in the thought…actually licking pussy, not just fingering the way I had done. Which had been pleasurable and exciting enough in its own way. At least I wasn’t so naive that I didn’t know what a clit was, or that it felt good to a girl when you touched it, played with it. But I’d never actually considered licking it…until now. But not only that. As the image suddenly filled my head, as I sat there imagining myself actually doing that, it suddenly dawned on me. It wasn’t Marjorie’s pussy I was considering or thinking about doing that to. It was Dee’s! It was the image once again of her standing there in her backyard, naked…taking the sheets down off the line. Only in my mind, I was kneeling there in front of her, also naked…rigidly hard, my fingers pulling her pussy lips apart, that sweet delicious looking clit of hers (I could only imagine it being so of course) as I knelt there licking it.

“Jimmy? Jimmy? Earth to Jimmy!” She said shaking me back to the present.

“Oh sorry…” I said feeling my face reddening; though I am sure Dee took it for embarrassment on my part as she shook her head positively at me.

“My advice,” she then said sitting up again in her rocking chair. “Tell her you’d rather wait, not rush into it for one thing. I’m willing to bet, she’s not really ready either Jimmy, and I’m willing to bet you one of my home-made pies, that she’ll thank you for it afterwards, if you don’t. But…maybe what you should do, is surprise her.”


“By doing what she’s already done for you, by going down on her…or rather, licking her pussy if you will.”

God I was hard, sitting there hearing her say that. Once again the image however, not of Marjorie, my girlfriend…but of Dee. And I knew at that very moment, I wasn’t ready. Not with Marjorie anyway…I liked her. I liked her a lot. But I knew at that very moment. I wasn’t in love with her. And doing something, like taking advantage of that, taking her virginity when I wasn’t, or giving mine to her either for that matter, wasn’t something either one of us should be doing under the circumstances. And to be perfectly honest about it, I now had to wonder about the rest of it too.

“But…I’ve never done it, not even sure how to do it for one thing. And what if…she doesn’t like it? Or doesn’t want me to?”

Once again she laughed. “Oh honey…one thing you’re going to soon learn about women. We all love having our cunts licked.”

OK…THAT was a new one. Cunt was a thing guys spoke about to one another, cunt…pussy…split, snatch, twat…hell, we had a bunch of names (never vagina though…isn’t that funny?) But hearing a woman use a guys word (back then it was anyway) or…maybe not. Regardless, hearing Dee use it. Well…that damn near pulled the trigger on the gun in my holster.

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