The first time I jerked off in front of my sister, it was weird for both of us.
And the weirdest part, to me, was how weird it was.
It had been a fantasy of mine for literally years. Admittedly, in my fantasies I was typically jerking off onto my sister, but the base ingredients were the same.
Turns out, and this genuinely surprised me, I’m a little self-conscious about the way I masturbate.
I had been pretty happy with the prep work I’d done. After slipping the hand-written note into her folder, I’d given it some time, just like I had with nudity.
I hadn’t honestly noticed any difference in the way that she got off on camera while I was in the room. Like I said, we’d been doing that for weeks, so I sort of knew she didn’t have an issue with it.
Afterwards, we were lying on her bed, watching camgirls, shooting the shit. The well of good ideas was truly dry at this point, and so the shows had almost become background noise – something to have on while we hung out, y’know?
Eight months earlier, that would have been Friends reruns in the den, and we would have both been fully clothed. Now, it was half-naked British girls (a lot of the best camgirls are British, I’ve found) moaning into their webcam, while my sister and I lay naked on her bed.
I loved my life.
“Oh hey,” I said casually, hoping that Ashley didn’t notice the slight break in my voice. “This girl’s great.”
Her name was Pink Lily; I’d checked her out a few times. Blonde, huge tits – the similarities to my sister were pretty much the whole reason I liked her so much.
Ashley fell silent, and the two of us watched Lily as she slowly accrued enough tokens to take off her panties, then her bra, then finally her shirt. Her huge, pink-nippled boobs fell into view, and I deliberately shifted my weight a little.
My sister glanced down, noticed that I was hard, and returned her attention to the screen.
I was laying beside her naked, watching a live cam show, sporting a huge boner…and she didn’t even care.
Lily quickly accrued enough tips to start the ‘cum-show’, and as she pulled out her Hitachi, I again aimed for extraordinarily casual.
“Oh, great,” I said. “Do you mind if I jerk off?”
My sister went very still for a second, and when she spoke, it was my turn to notice how forced-casual she sounded.
“No problem,” she said, her voice strained. She pulled away, slightly, so that no part of our bodies were touching. “Go, uh…go right ahead.”
The entire time, I found myself thinking “ah god is this the way that everyone does it”, or “I hope she doesn’t get bored” or “okay as soon as I’m done, I’m moving ’self-consciousness’ way, way down in my folder.”
It was still a dream come true, don’t get me wrong. My sister’s wide blue eyes, staring as I wrapped my hand around my cock, the way she tried to keep focus on the computer, her eyes occasionally darting over to my hand.
But definitely weird.
Like I said, I was nervous. I was nervous about what it looked like, what it felt like, how long I was taking (is it better to be fast or slow?) and my sister’s awkwardness had sort of freaked me out. But she didn’t say anything as I stroked myself, keeping my eyes firmly on Lily. Before too long, I came, three strong spurts, shooting my cum onto my chest.
I cleaned up, kept on talking, kept the conversation light. My sister joined in, but that weird tension never left her voice.
And I knew my sister was a little wigged out because – for the first time since she started letting me watch her cam – she was the one who suggested we crash.
“We should get some sleep,” she said, and I agreed, heading straight into my bedroom, wondering what had gone wrong.
Now, maybe I misread the signals. Hell, maybe she just wanted to be alone so she could get off again…but I strongly suspect that wasn’t the case. Maybe she just wanted some time to process what had just happened?
Maybe my expectations had just been too high; of course the first time was going to be awkward. Maybe I’d rushed things, and should have given her more time to get comfortable with the idea. Maybe I should have taken smaller steps – casually playing with myself in front of her, before leaping straight to masturbation.
I didn’t know, and I didn’t know how to know.
Here’s the thing, though: I’d been watching her cum for so long, I really hadn’t expected it to be an issue. When I’d added the note to her folder, I’d actually wondered if it was even necessary. We’d been doing it for weeks, after all.
I guess there’s just a difference between professional masturbation and masturbation for funsies.
The next day, I messed with my folder again, reducing my need to feel less self-consciousness. That immediately helped, but I still decided to wait a little while before trying again. No sense in pushing too fast, after all.
In the meantime, I was just really enjoying the time spent with my sister. She’s smart, funny, and now that I’d run out of advice to offer, we’d fallen back into our old banter – we’d chat and joke about TV shows, music, stuff from our childhood. Ashley’s trust manifested in weird ways – it meant she really appreciated my opinions, for example. Even outside of shows. It also made her more cuddly, which I enjoyed even when she wasn’t naked.
It was a full week before I tried it again – we had some camgirls on in the background (Russians, this time, just in case the country was doing something different that we could use) and I casually mentioned how hot one of them was.
There was a long pause after I asked; I guess on some level, I was hoping she’d ask me to jerk off, just to show how comfortable she was with it.
No such luck.
A few hotties later, I bit the bullet. (My reduced self-consciousness helped a lot there.)
“You mind if I jerk off?”
Again, that weird silence. Again, she shifted on the bed, ensuring that no part of us was touching.
But again, she answered in the affirmative.
After that, I decided that the only way to make it less weird was to do it more often. I mixed up the routine a little – it wasn’t always after one of her shows (I didn’t want her drawing any connections, not yet). It wasn’t always while we were both naked, and it wasn’t always while we were touching. I’d be on the computer, she’d be in my bed, I’d casually ask.
Always that weird pause, followed by that hesitant approval.
After almost two months, I could feel her starting to relax about the whole situation. She still never initiated it, but her hesitation started to fade.
And so I stopped asking.
We’d be sitting around, shooting the shit, I’d be on my phone, and I’d just pull out my cock and start jerking it. Her body would go stiff, but she wouldn’t object. Then I started doing it when we were laying next to each other on the bed – again, she was a little weird about it, but made no comment.
I’d had a plan. My next step was going to be start jerking off during one of her shows, see what I could do with that…but her reactions had scared me. She’d been so fine with everything else, every other step had been so easy…but as soon as I’d been overtly sexual, she’d been…weird.
It was too risky.
The change hadn’t stuck, for some reason – at least, not as strongly as everything else. I wanted to know why before I took things any further.
And then Ashley said something that took me completely by surprise.
We were laying on my bed, watching porn.
Normally we watched camgirls together, but I’d been browsing reddit while Ashley cuddled up to me and I’d seen a super hot preview.
The porn wasn’t anything special, but it was kind of hot. Two girls making out, a guy interrupts, they end up fucking him.
Lately I’d still just been pulling it out without asking, but for whatever reason, I went off-script.
“You mind if I jerk off?” I said, and Ashley shook her head without hesitation.
She still pulled back, but not as much as normal – her hand was on my side, her head was still partially on my shoulder.
And that’s when it happened.
“Do you mind if I do?”
If I’d been holding anything, I would have dropped it.
“Of course not,” I said, trying to sound as casual as I possibly could.
I was fully clothed; Ashley was topless, wearing a pair of those cloth short shorts. As I pulled my dick out, Ashley reached into her shorts.
I’d seen her get off literally hundreds of times by now, but this…this wasn’t a show. This wasn’t for money. This wasn’t for an audience.
This was for pleasure.
The girls on-screen alternated licking the dude’s cock as I stared at my laptop, trying desperately to get a good look at my sister’s reflection.
That was the first thing I noticed: when it wasn’t for a show, she was quieter.
It made sense. If nothing else, she wasn’t competing with her industrial vibrator for sound.
Her hand was underneath the shorts, another difference – normally I could see everything, but when it wasn’t for the pleasure of others, when it was just for her own pleasure, she apparently didn’t need to be naked.
God it was hot.
The best part, aside from ‘everything’, was the timing – Ashley came about twenty seconds after watching me shoot off.
Was it the sight of her own brother’s orgasm that finished her off? I don’t honestly know. But even though I hadn’t made any specific alterations in that regard, just seeing someone get off is hot, right?
I like to think that it was seeing me cum that pushed her over the edge.
This time, I was surprised in the opposite way – afterwards, things weren’t weird. I cleaned up, she licked her fingers clean (which: oh my god, oh my god) and we closed the porn and went back to hanging out.
Like nothing had ever happened.
After that, she started to get off in front of me regularly
Considering how often she was performing, I was amazed that she had any energy left for non-performative orgasms…but, of course, my sister has always been an over-achiever. Sometimes she’d get off while I did, more often it was just when we were hanging out – just whenever she felt turned on, I guess.
I tried to watch out for signs that she was checking me out while she came, but I was disappointed. Unless I was jerking off, her attention seemed to be fully consumed by whatever she was watching, or reading, or even just thinking about.
And even when I was jerking off, it wasn’t like she was staring at my cock the whole time. The only silver lining was that my climax would more often than not trigger her own. It was frequent enough that I didn’t think it could be a coincidence.
My cock was getting my sister off.
Ah. Maze. Ing.
After a few weeks, I was ready for the next step of my plan. I’d abandoned the idea of jerking off while watching her perform; the more a girl I was jerking off to looked like her, the less comfortable she seemed about me masturbating in front of her (and when they were big-titted blondes with blue eyes, she never ever ever joined in). Maybe it would work, maybe it wouldn’t; it wasn’t worth the risk.
It was an hour or two after one of Ashley’s shows. I just couldn’t wait any longer; I wanted to fuck my sister, and these slow, steady steps were starting to get to me.
It had to be slow; I knew it had to be slow. I didn’t have a mind ray I could use to erase her memory – if I didn’t make changes gradually, I had no idea how she’d react. If we suddenly started fucking out of nowhere, she’d be suspicious, and who knew what could happen. She could refuse to talk to me again, she could tell our parents…she could tell the cops.
She could find the filing cabinets.
I couldn’t have that. And so I knew I had to move slowly. It was just…excruciating.
As soon as I saw her drifting off to sleep that night, I slipped down the hallway, into the room, and started messing with her folders, getting everything ready for the next few days.
For the next part of the new plan.
Opening the ‘Trust in Jacob’ folder, I saw it.
“Comfort masturbating in front of my brother”.
I stared at it for a long time, processing exactly what I’d written.
I’d meant to write “Comfort with masturbation around Jacob.” You know – both ways.
I’d made one of my sister’s priorities comfort masturbating around me, and totally neglected to say anything about me masturbating around her.
No wonder she’d been weird. No wonder it had been months and months before she’d started joining in.
I was just lucky that it hadn’t been a bigger mistake. I’d never considered the potential consequences of writing the wrong thing.
She’d gone along with it.
I’d asked if I could jerk off in front of her, and she’d said yes.
Not because I’d compelled her. Not because I’d made that specifically a priority in her life.
Well, just because. Because she trusted me, I suppose. Because she loved me.
A smile of triumph formed on my face, and I continued shifting folders around.
She had no idea what was coming next.
She had no idea what was coming next.