I, Arielle: My Sex Diary

I had my first orgasm at 13. I had learned about masturbation two years before, at sleepovers with friends. Three (or four?) times, conversations after lights off led to that topic and we all ended up masturbating, more or less at the same time. Well, not every one of us. Being the youngest, I didn’t have any prior experience. Besides, my genitals are quite sensitive and I can’t touch them directly (that is why I’ve come to love sex toys). I tried to masturbate with the others a bit, but every time I gave up after a minute or two. I would guess they were laughing of the baby who couldn’t even jill off behind my back. I didn’t care. Much.

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Oh well, I admit it. I was ashamed of it. I thought I wasn’t normal, or sexual, whatever. I was too shy to ask anyone for help either, although now I realize it could have saved myself some trouble. Now I know a woman can get herself off without her fingers but back then I didn’t have a clue.

Now back to when I was thirteen. I came to notice that many people slept on their side with a pillow between their legs, my older sister among others. Twice in the past I had overheard her moans during the night; was she humping her pillow? I’ll never know.

I wanted to try the pillow too, so I picked one in the closet one evening, put my pajama on and went to bed. It was truly more comfortable, although I wasn’t used to sleep on my side (I had always slept either on my back or on my stomach). Habits being what they are, I sort of fell back on my stomach, the pillow blocking my legs on the side. Twisting a little more brought the pillow straight on my pussy. I didn’t realize immediately how pleasurable it was. But after a while I noticed I was moving my pelvis, humping the pillow. I stopped. What was I doing? I didn’t yet realize I was actually masturbating either. I resumed moving my pelvis. It felt good, so I kept doing it. I started to feel a strange warmth in my stomach too.

According to my bedside clock, about half an hour passed. I couldn’t sleep. At this point all I could think of was to keep massaging my pussy. Only then did I get it. I had found a new way to masturbate (or so I thought), and one that worked for me! Perhaps I should try harder then. I would have my waist face the bed even more, pressing my pussy harder against the pillow. Now it was feeling really good. I tried harder, my breath quickened and it became even pleasurable enough to moan a bit. My parents were watching TV upstairs so I didn’t worry too much about them, but too much noise could alert my sister in the next room. I tried to contain my moans, first by controlling myself, then by putting my face in my other pillow when I had to.

This lasted quite a while, two hours maybe. At some point my parents turned off the lights and went to bed so I would have to be a bit more careful not to get caught. My sister didn’t show sign of going to bed though; quite the contrary, she turned up the volume of her CD player, meaning she would stay up for most of the night as usual. Several times I thought she had heard me, but I couldn’t freeze completely. I had to continue humping. Each time I was terrified of getting caught.

How about another hour hanging on the edge of orgasm? Or two? I think I kept doing this most of the night, slowing down the pace then resuming, trying not to make too much noise. But at some point I pressed hard enough to go beyond the threshold… and rock the bed slightly. I couldn’t help keeping it up, though, as I sensed something coming down there. I kept it up another minute until I could hardly contain my moans any longer even with my pillow as I shook the bed for real, grinding as fast as I could, grabbing both sides of my mattress, quivering from the sudden wave of pleasure that spread through my body. I had just had my first orgasm and it was the most fantastic feeling I had ever experienced.

Of course my sister had heard that last part, even through the wall and the music. She came to my door and opened it.

“You alright?” she asked.

“Yeah, I’m fine” I replied.

“Didn’t sound like it… Good night.”

Although it may have sounded like a nightmare, it was smelling something else through the room. She sure knew what I had been doing, but left me alone. Speaking of smell, I noticed my panties and the pillow were soaked with my juices (another thing I didn’t know). I had to change before going back to bed. If my sister still had doubts about what she heard a moment ago, they sure vanished when she heard the drawer.

At my birthday three weeks later, she met with me alone in my room and gave me a present. It was my first sex toy, a silver bullet vibrator. She told me it was small enough to hide so mom and dad wouldn’t find it. She also told me to be more quiet next time. I didn’t know what a vibrator was (none of my friends owned one and I was totally clueless by myself back then), but I knew what she was talking about and my face turned red. Before she left, I told her to wait, then searching for my words, I admitted I didn’t know what it was or how to use it. Now it was her face turning red, asking me if it was some sort of joke. I thought for a moment she would laugh but then, after freezing for a moment, she did the most unexpected thing.

“Mom and dad won’t come back anytime soon, so let’s give it a try,” she said. She tried to look confident but I knew she was a bit embarassed herself (and so was I; somehow I knew what would happen next). She taught me how to put the batteries in and turn it on. Then she told me to sit on the bed while she closed the door and pulled down the shades. “Now pull down your pants to your knees and lay down”, she told me, then “turn it on and put this on your clit. You can do it through your panties too. Yeah, like that. Do you feel anything?”

You bet I was. It took me a couple seconds to find the spot, but once I did, it instantly sent a chill through my spine. “Yeah,” I replied.

She laid down on the bed right next to me. She was three years older and her chest was fully developped. I couldn’t take my eyes away from it, envious; she was so sexy. But soon I would turn back to the ceiling as my feelings quickly intensified. That thing was much better than humping the pillow. Soon I started moaning, even though I was ashamed of doing it in front of my sister. I believe she didn’t want to watch, but didn’t want to leave either so she just laid there besides me, sort of witnessing the whole thing. She must have noticed it was taking long because just as I thought she would leave, she told me:

“Don’t you play with yourself while you do it?”

“What do you mean?” I managed to ask.

“Well, don’t you play with your boobs?”

I didn’t dare to answer because of the obvious fact that my breasts weren’t yet nearly big enough to deserve to be called boobs. Even compared to my friends’ they were ashamingly small. My bras were still AA cups at that time (to think my chest now wears 34C, I sure have grown up since). I was about to learn it didn’t matter though. She turned off the vibe. “Don’t worry,” she said, “it’ll only make it better once you resume it. Now remove your shirt,” that I relunctantly did, “then your bra,” that she did for me before laying back on the bed, her arms above her head. “I always play with myself before doing it. It’s called foreplay.” Then she told me to caress my breasts. I was getting so embarassed to do these things right next to my sister that I couldn’t bring myself to do it.

She sighted. “Don’t worry about it,” she said, but it didn’t make me feel better. “I hope you realize not too many girls your age have a big sister like me to teach them these things. Why not get it on while I’m still in the mood? I’m just trying to show you a couple tricks so that gift won’t go to waste.” Now that made me feel even worse, even though I knew she was just trying to help. Then she started to laugh. I was afraid she was laughing at me, but instead she removed her own shirt and bra and started to show me. “Won’t you do it with me, then?” she dared me. And so I did, but not before taking a good look at her generous chest and how she skillfully massaged her boobs with both full hands. She even pinced her nipples (that I don’t really like however). I started to imitate her. Soon her breath deepened, and so did mine. I had never realized before that touching my breasts could be pleasurable. Then I watched her slide her hands down to her stomach, then back up to her neck, down again to her ribs, her flanks, her waists, her tights, outside then inside, teasing her pussy, then crossing her arms, back up to her shoulders down to her arms, back to her chest, and so on, for a good fifteen minutes. It was very erotic. I enjoyed watching her pleasuring herself to the point that I would forget to accompany her (she reminded me twice to keep going). I did my best to explore my own body just like she did, even though it was obviously a bit awkward. I couldn’t believe we were doing this. But at the same time sharing my pleasure with a more experience person was very arousing and I learned a lot from watching her. Also, it was a lot less embarassing that way.

Then she pulled down her jeans and started to tease herself between the legs, slowly closing to her pussy, withdrawing, caressing her stomach, her breasts, then down to her tights and crotch. She removed her panties only once they were soaked, and threw them away with the jeans while removing her socks. Once in a while she would quickly explain me a thing or two between two moans. I enjoyed imitating her, teasing myself just like she was doing. Then she started to stroke herself, insisting it was the right time. First she went slowly, then suddenly quickened pace. She grabbed a breast with her free hand and moaned even more. Then I followed myself, turning the silver bullet back on and putting it on my clit. That amazing feeling returned, intensified once I, too, reached one of my breast. My sister was right about all this: it was intensely more pleasurable that way.

Then she released her breast, pulled her hair and stopped stroking. I knew she hadn’t come yet. “Stop right before you cum and wait,” she said.

I nonetheless continued for a couple more minutes before reaching that point. I stopped just in time like she had. Meanwhile, she had already resumed and stopped again. “You should do that for as long as you can stand it, ” she explained. “Then when you get yourself off, it’ll be fantastic.” We were both laying there side by side, motionless. Then we resumed and stopped again almost together. “I can keep this up for hours,” she admitted. “Sometimes I spend most of the night jilling. I put some music so no one will hear anything.” In other words, she had just confessed she had been masturbating quite often right next to me, including the very night she caught me humping my pillow. “Sometimes I do it on the phone with my boyfriend too,” she continued.

We kept doing this for another half hour, I believe. She taught me you can put the bullet inside your pussy and something about that pleasurable spot on the upper wall. I explored my vagina looking for it while she vigorously fingered herself. We moaned and groaned, grabbing the sheets, our eyes rolling backward. Finally, neither of us could take it anymore and we came together in unison, shaking the bed. It was just as fantastic as she told me it would. Both of us laid there afterward for at least five minutes, all sweaty, quivering, shivering, still moaning.

Afterward she told me how to clean the bullet and even suggested a place where I could hide it: behind my bedtable’s drawer (it was detachable and there was some room left). We became very close on that day and for as long as we stayed under one roof, we kept masturbating together about twice a month; she taught me everything she knew.