I was sixteen at the time. My sister was fourteen. We had talked about masturbation a bit. We were quite open, and as I understand now, very good friends and confidants as brothers and sisters go.
We both knew we masturbated, but had never seen each other do it. I hadn’t even seen her naked in years. I kind of wanted to. She did show up in my masturbation fantasies rather often.
One day when our parents went out to a movie, Sis and I were watching something on HBO. I don’t remember the details, but at one point, it was insinuated that a woman was masturbating. Nothing explicit was shown.
I casually asked my sis, “Is that what you look like when you masturbate?”
She smiled and said, “What a question! I’m not going to answer that!”
I left it alone.
A moment later, she said, “Well, yes, I think I do look like that….”
“Except, what?” I asked.
“Come on, you can’t leave me with a mystery like that!”
“Yes I can.”
“Fuck you,” I said half jokingly, trying to let the idea of her masturbating leave my mind. I had suddenly become quite horny, even though it was my own little sister.
We turned back to the movie. She had evidently let the situation drop. But my mind was stuck in high gear.
After a pause, I sheepishly said, “I’ll tell you what I like, if you tell me what you like.”
“OK, but you first.”
After probably turning red in the face, and trying to figure out whether I should say it or not, I finally said, “I like pulling my scrotum. Stretching it tight.”
I was expecting her to laugh. Instead, she said, “Interesting.”
Then, silence for a while – until I couldn’t stand it any more.
“Oh, OK. So what I like is inner labia pulling. That’s why I said interesting. We both seem to like some sort of pulling. Genes, I suppose. We’re in the same family, so I guess we should like the same thing. It’s not so strange.”
I kind of figured that was that, so I turned back to the movie, which had become rather boring.
Speaking again so suddenly I almost jumped, she said, “Well if you must know…”
I hadn’t asked to know anything more, but whatever, right?
“Well, um, I keep dreaming of someone else pulling my labia. I mean, if I could get someone to do that to me, I think I’d be in heaven.”
I didn’t even know how to answer that, so I said nothing. But I was thinking crazy things at a hundred miles an hour. Like, wow, I wonder if I could ever somehow arrange to pull her labia for her? Wouldn’t that be something? Maybe she’d even pull my scrotum…
I turned back to the movie, knowing I had to either cool my jets, or go into my room and jerk off. I was just about decided to excuse myself and do the latter, when she said something quick, and a little too loud again, almost causing me to jump once more. I could tell by the way she was speaking that she was nervous or something. Horny, maybe?
“I was wondering…”
“What?” I asked with excitement building. I assumed she have some sort of very fun question for me. Something terribly sexual I hoped.
“I was wondering, well… I mean, well, would you be willing to pull my labia?”
“Boy would I!”
Thinking quickly, I added, “But you’d have to pull my scrotum.”
Damn, I went too far by asking that. Or she thought better of the whole idea. Or something.
In a small voice she said, “Yes, let’s do it.”
I don’t know why, but as she started laying plans out loud – that we’d turn up the furnace, go to her room, and take off all our clothes and ‘do it,’ I started shaking. I was shivering as if it was 30 degrees in the house. And, I was terribly horny. And something else. My heart was racing. I was scared! I didn’t want her to notice.
“Yes, I guess I am,” I answered.
“Cool. Way cool! I read somewhere that’s a sign of very good sex, or something.”
It was my turn to say “Interesting.”
We got to her room, which was already warming up nicely. Then we just stood staring at each other.
“Come on, silly,” she said, and with that, she pulled off her T-shirt, then her bra. My sister had the first real tits I had ever seen in my life, and they were brilliant. Beautiful. In retrospect, they weren’t very big, not even close to average, but they were real. Her nipples were just little things, but hard and pink.
Before I could even take that in, she was stepping out of her shorts. By gosh, she had been wearing nothing underneath! Now, I was seeing a real live vagina for the first time ever. Well, not entirely, I was just seeing her crotch hair.
I kept thinking this whole thing would go south at any moment. She’d probably chicken out. Or maybe I would. Then it occurred to me I was still wearing my shirt and shorts.
“Well?” she inquired impatiently.
There was a part of me that wanted to run out of her room, retreat to my own room, and try to think about the whole situation. To understand the reality of what was happening.
Perhaps it was the notion that I didn’t want to disappoint her that spurred me on. In a moment, I was out of my clothing, sporting a huge erection right in front of her.
“Cool!” she said. “Can I touch it?”
“Frankly Sis, I’d love that!”
She reached out, and placed her fingertips lightly on the end of my penis. I felt something like a most enjoyable electric shock. My penis became even more erect if that was possible.
Soon, we got down to the business at hand. I was touching a real live pussy for the first time in my life. Soon, she laid on the bed, spread her legs, her outer lips parted, allowing me to touch the pink inside. She showed me her clit, and explained how rubbing that is what women like.
Poor, poor me. I couldn’t hold it together. She had let go of my penis as she laid down, and it had been a minute or more since she had touched it. But, it started jumping in those automatic twitches us guys know so well, and sperm started pumping out. It spilled on her legs, on her bedspread, on my thighs, and some got on the floor. I was deadly embarrassed.
“Cool!” is all she said. She then grabbed some Kleenex from a box and started wiping up the mess. Then she reached out with some fresh Kleenex to wipe the cum off the end of my dick. I jumped in sensitivity. She laughed, and cleaned me up very gently.
I had lost my interest a little bit, but not as much as you’d expect. I was still very, very interested to pull her labia as my penis was softening.
She laid back down, and I started gently pinching and pulling her inner labia. The thing was, I couldn’t get a grip on them. They were slippery with her fantastically good, but mild smelling girl juice.
She instructed me to keep trying to pull them, that the action, even if it wasn’t really pulling, felt really nice.
So I did, and within a minute, she was convulsing so hard she nearly threw herself off the bed.
That was our first time. In the weeks that followed, she and I played several more times. I did learn to hold my cum longer, at least sometimes, so she could actually pull on my scrotum, which was at least ten times better than I thought it would be. I mean, when I stretch out my own scrotum, it’s nice, but when she did it, it was amazing! Sometimes, at first, she’d kind of pinch a testicle in the process, which hurt a little bit, but in general added to the joy.
We learned that I should attack her inner labia before she gets wet, in other words the minute her pants are off, so that they’d be dry enough that I could get a proper grip. That didn’t really work very well, because she was already wet most of the time. We then figured out that all we need to do is dry her with some Kleenex. Then I could get a good grip.
I learned that she didn’t want gentle pulling. I was pulling surprisingly firmly, and squeezing them hard too, and that sent her into long spams of thrashing around in fantastic orgasms.
Later we both learned how wonderful a finger in the ass can be. When she simply placed her index finger against the outer surface of my anus the first time, I squirted sperm immediately.
We figured out that I’m a bit of a premature cummer, and we worked long and hard for a year on that, and she finally got me to where I could keep it together for a while.
I ended up with a girlfriend a year later. She turned out to be wild in bed, so my activities with my sister came to an end. A year after that, she got a boyfriend. I thought the guy was a jerk. Then I figured out I was a bit jealous, which was weird, since I had a good, steady, lively girlfriend. Turns out her guy wasn’t so bad after all. She had planned to become an artist, and he, while going to college to become a psychologist, encouraged her all the way, almost forcing her to enroll in art school. Now, she’s a successful graphic artist and freelance painter, and her husband is a professor of psychology.