This story really starts a long time ago.
I grew up in the Midwest, the son of very religious parents who had a small farm where they raised my sister and me.
My sister is older, two years older, and our farm was pretty much in the middle of nowhere so I never had many friends and neither did Olivia, my sister.
While this all begins back when we were children, the most significant development happened to us separately, I lost my wife to a heart attack when I was fifty-two, and my sister's husband deserted her for a twenty-six year old when she was forty-one.
It was about three years after my wife died that Olivia had a job interview with a company that was located in the city where I lived. Of course, rather than having her stay at a hotel, I had plenty of room in my four-bedroom home, so she stayed with me.
Well, it turned out that she was offered the job and when she told me, I offered her my place to stay, even permanently, if she wished. After all, we had always gotten along well and it would be nice to share some of the cooking and cleaning chores along with the company of someone I'd known so long.
She agreed and two weeks later her household things arrived and we spent the day getting her settled in.
That weekend, we decided to take it easy after getting her settled in and on Saturday evening, I did us a couple of steaks on the grill which we had with baked potatoes and some Cabernet Sauvignon I'd bought from a winery I'd visited in Sonoma Valley.
After we'd eaten, I was pouring from the second bottle as Olivia said, "Remember when we were kids and you asked me about masturbating?"
Honestly, I had pretty much forgotten all about it, but it did begin to come back.
"Oh, yeah, I remember playing with it in the bathtub one night and I'd soaped it all up because rubbing it like that felt so good."
"Yeah, and the next morning, when we were feeding the horses, you asked me about it."
"Well, I didn't really know what'd happened. Of course now I do, I'd had my first orgasm, my first cum. But I didn't know what it was, only that it felt damned good."
"So, you asked your older sister, your source for all things sexual, and I told you it was natural and fun and, I think I got you that book a day or two later, the one Mom and Dad kept hidden away. I got it out because they were away all day at auction."
"Oh, yeah, it had drawings in it, how well I remember. You showed me the chapter to read."
"Right, and I told you to take it to your bedroom and read it before you got dressed. Well, I figured the best way to learn is to try it, right?" she said as she slid her empty glass across the table toward me.
"Well, of course, it was full of medical terms not the words I was used to like 'wee-wee' and stuff. We were just never told very much, it's kind of lame to look back on all that now."
"I remember giving you about a half hour, maybe more, then knocking on your door to see how it had gone."
"Oh, I still remember that, Sis, you came in and locked the door then asked how it had gone. So, I told you the truth, that I didn't understand half the words, so, well, my developing sister just pulled off your nighty and stood there naked. I just couldn't believe it. I remember I didn't dare say a word for fear that you'd leave."
"Oh, I didn't leave, did I? No, I got into bed with you. I remember pulling the sheet off you, seeing your hard dick sticking straight up, it was so cute. Is it still cute?"
"Not sure it's been called 'cute' since then but, well, I suppose it's pretty average."
"No such thing, little brother, no such thing. Remember what I did after I got in bed with you?"
"Oh, how could I ever forget. You just reached over like it was something you did every day, took it in your hand, told me to lay back and relax and you gave me about a dozen strokes and I cummed all over my stomach and chest."
"Boy, you sure did, you were so cute, laying there just covered with your cum, I took your briefs, remember, and wiped you all clean and told you that's what boys do to make themselves feel good and got up and left you a wiser man," my sister said laughing.
"Yeah, but you never did it again, Sis. I've been waiting all these years," I kidded her.
"You and half of mankind, James, how about pouring the rest of that wine?" she asked sliding her glass over. I split the rest between us and our talk went to other things.
It was fun reminiscing about that one time when Olivia and I were together in a sexual sense and, later in bed, I put a few drops of lube on my hand and began recalling how it felt to lay there as a young, inexperienced boy as my older sister masturbated me.
It was really coming back when I heard a soft rap on my door.
"Jame's are you asleep? Can I come in?"
I quickly wiped my hand off and told my sister to come on in as I snapped on the bedside lamp, raising my knee to disguise the erection that would have otherwise been obvious even from outer space.
She came in wearing a short nighty and said, "I've been thinking about what we talked about after dinner, over the wine," as she sat down on my bed next to me.
"Oh, about the time you got me the book and all?"
"Yes, well, the book, but more about my masturbating you way back then."
She was smiling so I didn't think I was going to hear any regret over what had happened so many years ago when we were young.
"So, what is it you're thinking?"
"Well, it's been over forty years now and, well, I think my brother deserves a hand job at least every forty years, don't you?"
I told you that I had my knee raised so she couldn't see the erection she'd walked in on so I simply dropped my knee down causing her to say, with a big grin, "Well, looks like after forty years you're really in need."
I pulled the sheet away as she stood there. I could see the dark outline of her nipples and, below, a faint outline of dark pubic hair that looked trimmed, maybe a landing strip from the look of it.
She sat down on my bed and curled her fingers around my cock moving her hand up and down slowly.
"It's sure bigger now, this is a proper cock, little brother, it more than fills my hand these days."
"Yeah, well, back then I was just a kid, things do change, look at you."
"Yeah, well, they're bigger than the A-cups I had back then, wanna see?" she asked not waiting for my answer as she pulled off the nighty. "You got any hand lotion? I don't want to make this sore," she asked nodding at my cock.
My sister was an attractive woman, about five-five, still nice and slender, her breasts were large, probably C-cups, and, not surprisingly, did have a bit of downward curve, but were still very nice. Her nipples were large and pink and, yes, there was a small 'landing strip' right above the pillowy lips I could see as she sat next to me cross-legged holding my cock.
I reached over into the bed stand drawer and brought out a small bottle and handed it to her.
"Oh, it's the stuff I use, works good," she said as one hand held my cock steady as her other hand let a few drops fall on the head.
Then she began moving her hand up and down on me, each stroke ending in a twist at the top.
"You can feel me up if it helps, James," she said softly as her hand sent wave after wave of pleasure across my body.
I reached over and petted her breast as she smiled, saying, "This seems nicer even than last time, don't you think?"
"Sure feels better than I remember, though, at the time, when I was just a kid, it sure felt good. This is nice, Sis, really nice. Glad you had this idea."
"Thought you might feel that way," she said saucily as I lowered my hand down from her nice, warm breast to between her legs.
I didn't touch her pussy for a minute to see if she might object but she just kept on masturbating me so I slid my pointer finger along the wet gap between her legs.
Moving my finger up and down along the cleft, I began pressing in just a bit, again, just making sure she didn't object, after all, she hadn't really said I could finger-fuck her, but she just kept doing me so I just kept doing her.
"Remembering it now, James? All those years ago?"
"Oh, not really, this is so much nicer. And I'm getting to make you feel nice, too."
"That you are. I've sometimes wondered why I never went any further than that one time I jacked you off. Well, maybe I should try to make up for it. What do you think?" she asked as she bent down and kissed me, sliding her tongue in my mouth and sweeping it around while her hand slipped up and down my shaft.
"I think I'd like that. I'd like that a lot," I said as she jacked me up and down.
She was good at what she was doing to me, that was for sure. I didn't really remember much about the first time she masturbated me but this time, oh, this was so good.
She began using both hands and then I knew it wouldn't take long.
I was now fingering her with my middle two fingers as I felt my cum begin to rise. Suddenly, my whole body froze and cum began fountaining up from my cock.
"Oh, wow, look at you. That's sure gotta be more than the last time I did this," she laughed as she continued stroking my cum-covered cock. "Feel nice?"
"Mmm, just great, Olivia, I'd like to get you off now, okay?"
.... There is more of this story ...