Dear Sweet Dee

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Many Feathers
Many Feathers
10,503 Followers

She sighed then, her eyes closed as though remembering she once had. "Or at least I certainly used to," she added even more softly than anything she'd said before, which is also when I noticed a small tear run down the side of her face, which she hurriedly wiped away, turning as though hoping I hadn't seen it. Too late. I had.

"You're crying!" I said standing out of worry and concern for her, totally forgetting for the moment that in doing so, I had inadvertently displayed myself. Not something I would have normally done, and now painfully aware of the fact that I had as she was looking down, or rather at me...which then drew my own head down paying attention to myself. Had it been any other moment in history...I'd have probably been proud. I don't think I'd ever been that hard, that full...that erect, my jeans bulging out so much so, that a blind man (or woman) would have felt the change in the air surrounding it.

And then I said a word I'd never once said in front of her before. "Fuck! Dee! I'm sorry!"

**

Once again she had laughed, but put me immediately at ease. "It's ok Jimmy, I've said that one a few times myself," she continued chuckling, though her eyes remained glued to the very obvious, very pronounced erection sticking out of my pants. "I think though...it's probably time for you to return home and perhaps get ready for this evening. Just remember what I told you...if it feels right, then ok. If it doesn't...well then, you've still got plenty of time before you rush into anything."

She actually stood then, walking forward to hug me. (Yeah...picture this), so I'm bending (or bowing if you prefer) trying very delicately here not to poke her in the stomach with what is a very obvious, almost painful erection. She's still chuckling while we do this, giving me a soft little kiss on the cheek as she did. Now that's not abnormal either, but it did seem to linger for like a split second longer than usual, not to mention the fact, bowed/bent as I am, for some reason her fairly large full breasts seemed to press against me a bit more than normally as well. And of course, that did little if anything to squelch the predicament I now found myself in.

I finally backed away, or rather almost pushed away, just as she did, that damndable smile still on her face, and worse, another obvious glance downwards towards my crotch as we did that.

"Maybe...you should do something about that before tonight," she now laughed pleasantly, and even sighed when she said that. "Ah...to be young again," she finished, and then stood there at the doorway waving at me as I hurriedly (somewhat still stooped over mind you) towards my place.

Luckily for me, no one was home, so I managed to make it upstairs to my room without any further incidents. But, I had already made the decision to indeed "do something about it" as Dee had said, even if Marjorie and I ended up "doing it" or doing other things later on this evening.

What I now knew however...strange as it sounded. And what likewise bothered me to some extent, was the fact I knew with one hundred percent certainty, that I wasn't in love with Marjorie. The person I was in love with...was Dee.

**

Once inside my room, I literally tore my clothes off jumping onto my bed. I honestly believe this was the horniest I had ever been, which was odd in a way, as except for a little erotic banter between us, and the kiss...and the feel of Dee's soft full breasts pushing against me, well hell...there just wasn't much more than that. Certainly not enough that it should have made me this horny, this aroused. And yet...I was. I didn't have one of those monster cocks you're always hearing about. Average sized perhaps, though I was a bit thicker around than most I suppose. But what I was at the moment, was fucking harder than I ever remembered being before. Looking down at my own dick, the head of it seemed to have ballooned up to mushroom size, a dark deep purple color in fact, which was again something relatively new to me. I wrapped my fist around it, squeezing it...watched the emergence of not just one droplet, but a sudden runoff of pre-cum fuck batter, and then did so again, producing yet another pearly little silly string of juice that now clung to my fingers like a spider-web.

After I had spent several long minutes just teasing the shit out of myself, I began pumping it seriously up and down. Slowly at first, but with ever increasing rapidity as my mind suddenly went into overdrive. I now found myself accessing archives that I had long since locked away in memory, not a whole lot of them mind you, and not many that probably most guys would have held onto for their masturbatory fantasy material. But the truth of it was, each and every one of them had something to do with Dee for as far back as I could remember, and as far back as each and every incident qualified as "cock-throb" material.

I had even gone so far as to catalog them in order of priority. Like the day I'd gone over to help rake up leaves, needing another bag, walking over to ask her where she kept them. She was kneeling down of course, leaning over pulling out a few stubborn weeds with her hand. As she did, her blouse had opened considerably, giving me my first ever look at the smooth softness of those magnificent tits of hers. Unfortunately, she was wearing a bra, though even seeing that, most of it in fact, had sent me running off to my room a short time later.

My second filed away fantasy of hers had been when she'd tripped and fallen. Maybe it shouldn't have been one under the circumstances, and wasn't at the time as I'd been genuinely concerned for her. But she'd just retrieved a bag full of groceries out of her car, turned to head into the house just as I came out. Seeing me, she waved, but in doing so, forgot to look where she was going and tripped over the hose in her yard, suddenly she's falling, groceries spilling everywhere at once. Naturally I ran over to her to help her up, and then help collect the spilled contents now scattered everywhere. This was my second look down mammary lane, though this time, I got to see both boobs, sans bra, she hadn't worn one!

As I lay there in bed, pleasantly stroking myself up and down, I clicked off each and every little incident one by one, working my way up to number one as I did so, trying to time the orgasmic bliss I was rapidly approaching before reaching it. That day...that very special day, which was in fact only a few weeks ago now, had made it to the top of the list by leaps and by bounds.

Oddly enough, I had stayed home not feeling well. I wasn't dead-sick, just the sniffles, sneezes and typical cough that good old mom had used in her own concern, to convince me to stay home rather than go to school. (I owe you one mom) I later told myself. Outside, it had started to thunder and lightning, something that always fascinated me, and which I enjoyed watching. Walking over to my bedroom window to look out, it was then that it started to rain and rain pretty hard. Suddenly before I even realized what it was I was looking at, Dee came sprinting out of her back door into the back yard. I knew then what was happening. She'd put out several sets of sheets to dry out on the line as opposed to throwing them in the drier, something my mom very often did as well, preferring the smell of wind-dried sheets, just as Dee obviously did. In a hurry perhaps, or maybe (as I later wondered) having just gotten out of the shower, and then realizing it was about to rain, she'd coming running outside. I saw her turn, starting to undo the clothespins, which is when the robe she was wearing, came completely open. She made no effort to retie it either, the rain truly starting to come down now. But I stood there in my window, (though why I now did this I don't really know) stepping back a little, though still keeping a good eye down on where she was. Both breasts, both of those incredibly beautiful, full bouncy tits staring at me. Each one with humongous (ok, maybe they weren't THAT humongous) but when you're seeing them for the first time, they sure as hell looked like it...areolas. Dark brown, (something to do with her heritage perhaps, since Dee had once said she had Spanish blood in her) and then this small little dark patch between her legs. It wasn't this unruly looking triangle either, but it acted like a beacon to me as I stood there in the window looking down at her. I was seeing her for the first time ever...completely naked!

And then I remember her looking up towards my room. I had stood frozen, looking down at her, wondering if she could see me, had seen me. But she merely looked away, finished pulling down the rest of the sheets off the line, and never once made an effort to cover herself up as she finished doing that. She then turned and headed back inside the house.

It never failed...just before the turn, I erupted, as I was doing now. Needless to say, I'd cum a lot thinking about that moment, but I have to also say...laying there the way I was now, horny as I said I truly was, I began spurting unlike anytime I had ever spurted before in my entire life. It was almost impressive enough that I felt like telling someone. (I said almost). The first few spurts actually surprising me, going well up and over the top of my head, hitting the headboard, if not the wall behind me, (which I later ended up cleaning up after) but after those, readjusting my aim just a little, I was still surprised and in awe of myself as I emptied my nuts against myself, finally having to cup my hand over my dick because it was spurting so much. I even briefly wondered if there was some sort of a valve I'd somehow fucked up, thus allowing my cock to continue to pump out streamers of white sticky stuff as I'd never squirted this much of it in my entire life before. Finally, as it began to ebb, and now just ooze slightly out of the tip, I released my dick, still seeing stars, still trying to catch my breath...and the image of Dee standing there in her yard looking up at me forever frozen in time as I lay there.

And then my phone rang.

"Fucking A!" I jumped scaring myself to death when I did. "Now what?"

**

It was Marjorie, and she was balling her eyes out. "Oh Jim! Jim! My God damn, fucking little sister!" She wailed uncontrollably over the phone.

It was a day of firsts all the way around. Never once had I heard Marjorie cuss like that before. A few sprinkled damns, hells, and even a shit or two once, but never once had I heard her say God Damn, or EVER use the proverbial "F" word!

"Calm down Majiee" I said using the cutesy affectionate name I'd begun calling her, which usually did the trick...but not this time as she kept talking over me even then. "What happened?"

"She...she...she told mom and dad!"

"Told them what?" I asked as the hairs on the back of my neck suddenly stood up. I knew her dad, he'd as soon kill me as look at me, and he was twice the size of any man I knew, so I also knew he could do it too!

"Oh Jim, Jimmy...I'm sorry, I shouldn't have ever confided in the little shit, she...she told them about our plans for this weekend!"

I was stunned hearing that, Suzie, Marjorie's little sister could indeed be a pain in the royal ass, and usually was whenever I came over, always hanging around us as though hoping to catch us doing anything. So I wasn't too surprised at that. What I was surprised at, was Marjorie actually confiding something like that in her.

"Why did she do that?" I finally managed to ask her.

"Be...because she was jealous that's why! Jealous because mom and dad were forcing her to go with them over the weekend rather than letting her stay home with me. That's why! So she told them! Told them you were coming over after they left, so we could...'do it!'" She all but whispered into the phone. Which then made me wonder just how close her parents were to her as she stood there talking to me, though I'm sure she'd already had to sneak away just to make this phone call.

"So now what?"

Marjorie started bawling again, which took me another several minutes in which to calm her down enough to talk coherently to me. "They...they're, oh god Jimmy! They're making me go to my Aunts house for the entire summer!" She burst out once more. "And they're making me go with them tonight too!" She now added. "I'm...I'm upstairs here in my room packing now, which is the only way I could have a moment to call you...tell you what was happening! Oh Jimmy! Daddy said I wasn't ever to see or speak to you again...if I did, if I do...he's...he's threatened to ship me off to some sort of girls school instead of University in the fall!"

I was speechless...sad in a way too. And yet...strangely elated.

"I have to go Jimmy," she said crying once again. "But...I'll, I'll write. I promise! I'll write you every day, somehow...someway, we'll make this work Jimmy. I swear it! I promise! I'll write you!"

So much for Marjorie. Though as it worked out, she only wrote me one letter. A dear John, or in my case a dear Jim. Which was just as well, all things considered.

But that phone call, that moment in history, brought about the most amazing memory, most amazing experience I ever had. And I had no clue it was coming either. Not until two hours later.

**

I actually was a little bummed after we'd hung up. Especially when I went looking for my two, (maybe it was three) errant cum-shots that had splattered against the headboard of the bed and against the wall behind that. Whatever hopes, plans...or assignations that had been scheduled for later, had suddenly evaporated.

Though weirdly...my cock still hadn't. Sure...it had gone down some, but it was still pretty fucking firm as I stood there looking down at myself. Horny is as horny does. But in this case at least, twisting another well-known phrase just a bit. I had a boner, and no place to go.

But at least there was Dee. And I smiled. If nothing else, I could go over, tell her what had just happened, maybe even get a sympathetic hug out of it, a peek down her blouse if nothing else...and add a fantasy file to my memory banks. At least losing Marjorie (though I didn't know it at the time that I really had) wouldn't be a total waste.

I stood in the shower as though I was getting ready for a date anyway, whistling...actually happy, excited, looking forward to perhaps milking the evening now at Dee's place with my tales of woe's me and all that. I was even then imagining Dee holding my head against her breasts trying to comfort me...feeling my dick stiffening there in the shower...half tempted to work it again. Though I refrained from doing so, wanting the full-on "horniness" of the moment to encase me when I went over there.

Needless to say, Dee was surprised when I showed up on her door two hours later. "Dee? I need a friend," I said.

They were the best five words I'd ever spoken to her.

**

"What happened Jimmy? What's wrong?"

And so I told her, though I didn't say it with a smile on my face, or with any of the oddly felt joy I was keeping inside. Like I said, my heart was skipping beats at the moment with the sudden realization of the secret I now had, the secret I couldn't tell anyone...especially Dee, that I knew what love felt like...for the first time in my life, because I felt it for her. Something I also knew, was a total and complete impossibility. And so I told her everything that had happened, and Dee...just like always sat there listening, though this time sitting beside me, and yes...towards the end, she pulled me towards her, placing her hand on the back of my head, and guess what...(Joy oh joy!) pressing me against those soft pliant breasts as I actually began to blubber just a bit. Not an act either. I was sad, yet I was also happy as a clam, and a little scared...a little nervous, a little melancholy, and a whole lot aroused.

"You know, I shouldn't be doing this, but since you are eighteen now, and soon out on your own here...I've never felt like if a man's old enough to fight for his country, that he shouldn't be old enough to have a drink." Dee knew of course I was contemplating going into the service, something Uncle Frank had done in having fought during the second world war. And with that, she then stood, walked over to a small cabinet where I know she kept a few bottles of liquor, mostly for guests or special occasions. Apparently, this was one of those. She pulled out a bottle of brandy, and poured each of us a shot glass. Bringing one over to me, she sat down beside me once again. "To life...and all its ups and downs." She toasted, clinking my glass, and then began to drink just as I added my own toast to that...though why on earth I then said what I did...still escapes me.

"And to all its ins and outs!" I added. "Or lack thereof."

Dee spewed her brandy...all over me. My bad...my fault, but it really was funny. And we both sat laughing so hard because of it that our sides began to ache, and then she saw my fresh clean shirt all covered with spewed brandy.

"Oh Jimmy! I'm so sorry!" She said honestly aghast, embarrassed and ashamed that she's basically spit-up all over me. "Take off that shirt so I can throw it in some water before it stains and becomes ruined!"

It's not like she hadn't seen me with a shirt off before. Plenty of times. And even as I took it off now, it didn't seem weird or inappropriate in doing so. But she was helping me remove it too, the neck was a bit tight, and the gold chain I wore around my neck had gotten caught on the collar. She was reaching up trying to untangle that before I inadvertently broke it. Losing my balance, I quite naturally reached out to steady myself. And when I did that, my hands came into contact with her breasts, just as she yanked and now pulled the shirt off me over the top of my head. We were both standing there looking at one another, my hands had been on her tits for a split second at least until the shirt came off. And then I did something I never thought I would.

I kissed Dee.

And then Dee kissed me back.

**

It felt like a dream after that. We didn't even really talk about it. We just sort of moved as though knowing one day this would happen, that somehow, someway, this was meant to happen. After we kissed, I didn't even ask her if it was ok. I just reached out again, this time placing both hands on both of her breasts, and stood there touching, caressing them. Dee closed her eyes, her head tilted back just slightly. And then I reached up, and undid the first button on her blouse. I even paused waiting a moment, fearing the words, "Jimmy...don't, we can't."

They never came.

I undid another button, and then another and another. The whole time her eyes remained closed, her mouth partially open as though trying to find breath, praying internally, her mouth moving a little as she stood there. Maybe she actually was. I knew I was...praying she wouldn't suddenly wake up and realize what she was letting me do. Thank God she didn't. (Sorry God...but I mean seriously here ya know?)

She was wearing a bra. Which I was now staring at. Up until this very moment, this was the most erotic, exciting moment of my entire life. And she was wearing a bra! And I was about to reach around her, and undo it. And she was waiting for me to do just that. And so I did. And yeah...I fumbled with it, fumbled with it some more. She laughed, opened her eyes for the first time.

"Want me to get it?"

It was a guy thing. At least for me it was anyway. And a pride thing too. And it was also funny in another way. It was 1967, and the Graduate had just recently come out. So here we were...I was Dustin Hoffman, and she was Anne Bancroft, and I was fumbling with her bra still trying to get it off, and then I felt her hands come down, and begin undoing my zipper.

I think she had me out, before I finally had her tits out. I don't honestly remember. All I know is, suddenly we were kissing again, fiercely, hotly, passionately. My hands now once again firmly on her boobs...bare boobs this time, with hard nipples...really hard nipples. And her hand was on my cock...my dick, my prick...pick one. Her hand was on it. And I was in heaven. And soon to be inside my own Mrs. Robinson.

Many Feathers
Many Feathers
10,503 Followers