The first time I came 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 jerk off.
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, in my experience) 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 a big 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.
My life was the fucking
best
.
Lily quickly accrued enough tips to start the 'cum-show', and as she pulled out her Hitachi, I again tried to sound 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."
And so I did.
Like I said, it wasn't like the fantasies. 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.
Amazing.
But yeah, definitely weird.
I was nervous the whole time. 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 now my sister's reaction had amplified that nervousness. 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 suggested, and I agreed, heading straight into my bedroom, my mind pounding, desperately wondering what had gone wrong.
It's possible I misread the signals. Maybe she wanted to be alone that night so she could get off again, but...I don't think so. I think she just wanted some time to process.
You might be wondering why I didn't just go and check her folder. Here's the thing, though; it's a list of priorities. It's not a list of every thought that flits through her head. Maybe 'Stop Feeling Awkward While Jacob Jerks Off' would've made an appearance, a new folder full of a step-by-step guide of what she was thinking, but probably not.
Maybe my expectations had just been too high, and the first time would've been awkward no matter what. 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 my cock in front of her, instead of leaping straight to masturbation.
I didn't know, and I didn't know how to know.
I'd been watching her cum for so long, I truly 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, chatting and joking 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 her show. It also made her more cuddly, which I enjoyed even when she
wasn't
naked.
It was a full week before I gave it another go. 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.
This time, I made sure to choose someone who didn't look anything like my sister, in case that had been the problem. I'm not normally an anxious person, but I'd been mentally running through the last time we'd done this, desperately trying to find
anything
that explained Ashley's reaction.
There was a long pause after I asked. On some level, I guess I'd been hoping
she'd
ask
me
if I wanted to masturbate, just to show how comfortable she was with it.
No such luck.
A few hotties later, and 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.
