I took a deep breath before placing the hand-written note into my sister’s drawer.
Technically, it wasn’t necessary. Technically it was a big risk. But I’d been so cautious for so long, and I’d spent hours thinking about it, trying to think of possible negative outcomes, and the worst-case scenarios I could imagine weren’t that bad.
And so I’d done it.
Inside the “Trust in Jacob” folder, the fifth-highest priority in my sister’s life, was a new file. It simply read “Comfort with nudity around Jacob.”
Now, technically this didn’t cover me seeing her shows through the computer…but that was fine. I’d seen her shows. I’d been watching them almost since she’d started.
Now, I wanted something more. I wanted to be in the room while she performed.
Keep in mind, writing something on a piece of paper doesn’t magically make it happen. Writing “sex with Ashley” hadn’t meant that my sister’s legs were suddenly wrapped around me on a daily basis – it just meant that it was a priority for me, something I was going to put effort into turning into reality.
Similarly, my new addition to Ashley’s folder didn’t mean that she’d suddenly be cool with me seeing her topless – but it did mean that she’d prioritize it, that she’d work towards being more comfortable around me while naked.
I considered adding a second file – “Comfort with sexual acts around Jacob” – but I didn’t think it was necessary, and it added the risk that she’d start bringing guys home and blowing them in front of me or whatever.
For a few different reasons, this was firmly something that I didn’t want happening.
Plus, honestly…the idea of her being embarrassed to masturbate in front of me (but doing it anyway, as was my plan) was kind of hot. I didn’t know why, nor did I have the inclination to try to puzzle it out.
The first day, I didn’t see any changes. I guess part of increasing your comfort with something is simply thinking about it, and I’d bet that’s what Ashley spent the first day doing.
The second day, she walked past me in a towel. That might not seem like a big deal – it sort of wasn’t – but it was new, and I definitely noticed. And I think she noticed me noticing.
The third day, she walked into my room in a towel. This was much weirder – she just wanted to hang out; there was no reason why she couldn’t have gotten dressed and then hung out, but instead she deliberately came and hung out in my room for a towel for like, two hours.
The fourth day, she sat down (fully clothed) and asked me the question I’d been waiting to hear.
“Jacob,” she said, avoiding eye-contact. “Would it…would it be helpful if you were in the room while I performed?”
“Yes,” I said, trying not to sound desperate. “I mean, y’know. It’d be weird, of course.”
“Of course,” she said, as quickly as I’d said ‘Yes’.
“But yeah, it’d be super helpful. There’s some stuff with lighting, angles – I can’t really help much unless I see you all set up.”
“Right,” she said thoughtfully. “Yeah, that makes sense.”
It didn’t. Not really. But her trust in me was so high, and her desperation to be comfortable naked around me had meant that she hadn’t even questioned my bullshit excuse.
“When are you next streaming?”
“Tonight? I mean, if you think that’s a good idea.”
I hummed and haw’d for a second, before agreeing that yeah, that would probably be a good time.
I mean, honestly, it was all I could do to avoid suggesting that we stream right now immediately right now yes please.
That night, I was hanging out in my sister’s room when her alarm went off.
“Oh!” she said, as if she hadn’t been obsessively counting down the minutes until her show started. “Oh, that’s…it’s time.”
“Oh yeah,” I said, doing an equally poor job of sounding casual about the whole thing. “Yeah, it’s time for your show.”
“So do you wanna…”
Ashley trailed off, and I threw her a grin.
“Relax, sis,” I said, hoping to god that I sounded smooth. “I mean, it’s just work. It’s not like I’ve never seen your show before.”
“Yeah,” she said, after a deep breath. “Yeah. You’re totally right.”
“Just pretend I’m not here. Focus on your audience, yeah? That’s where the money is.”
“Of course,” she nodded.
I gotta admit, I could get used to my sister hanging onto my every word, obeying my every suggestion.
Soon enough, I told myself. Soon enough.
Ashley’s show that night was spectacular. I mean, obviously I was a little biased…but based on the tip jar, it truly was one of the best shows she’d ever done.
To my delight (and very minor disappointment), she actually did what I said, and focused on the audience. The only time she even glanced my way was when she was removing her bra…but as soon as she removed it and her glorious boobs dropped into view, she was basically making love to her webcam with a laser focus.
It was amazing to watch. I had my laptop open, so I could simultaneously see what she was doing in real life, and glance at my computer to see her attention wholly focused on “me”. Like I said, it was absolutely one of the hottest shows she’d ever done, and by far the hottest thing I’d ever, ever seen.
The entire experience was magnified by being there, by being in the room with her. The sounds that her computer didn’t pick up, the angle, the smells…oh god, the smells.
Not just pulling my dick out and jerking off was probably the hardest thing I’ve ever done. When she pushed her Hibachi up against her clit, and started shaking and moaning in orgasm…fuck, every instinct in my body was screaming “Do it! Do it now!”
But I couldn’t. Hell, I still think I had a pretty good job of getting away with it – after all, my sister was trying to get used to nudity with her brother. And in that moment, she’d be so turned on…and she was an exhibitionist.
But it wasn’t worth the risk. I had a plan, and I was going to stick to it. Nothing was worth the risk of screwing that up, no matter how tempting it was, no matter how likely I felt it was to succeed…
I had a timeline, and I was going to follow it. Anything else lowered my chances of turning my perfect, sexy, orgasmic sister into my own personal sex slave.
Nothing was worth that risk.
After the show was done, I was worried there would be some awkwardness. After all, there I was, fully-dressed, while my sister was totally nude, sweating, and dripping wet.
But after she said goodbye to her followers (exactly as I’d coached her), she turned to me with a huge smile.
Like I said, the show was pretty much perfect. But I didn’t want to risk being booted out, not when she was sitting there comfortably naked, hanging on my every word.
And so for the next forty minutes or so I proceeded to ramble about lighting, and resolution, and phrasing. I didn’t give her any objectively bad advice, but even if she took all of it, I doubted it would have much of an effect on her tips.
She nodded and smiled and jotted down occasional notes. Finally, when I was totally out of advice to give (or make up), I stopped.
“Thanks,” she said sincerely, and I nodded in response.
“What are brothers for?”
There was a brief silence, and we laughed at the absurdity of what I’d just said.
“Hey,” I said, jumping in before the laughter could end and cause an awkward pause. “You know, the best way to learn this kind of stuff is to check out some other channels. Have you watched many others?”
“Just the ones you recommended,” she said.
“Come up here and we’ll find some and watch them now.”
I tried not to act like I was holding my breath. I hoped that my suggestion had sounded as casual as I’d wanted it to. I froze as she tilted her head to the side and considered my suggestion…and silently breathed a huge sigh of relief as she clambered onto the bed next to me.
She was naked. My sister was buck naked, had just cum all over her sex toy, and was lying next to me on the bed…getting ready to watch girls strip.
If you’d told me this would have happened a year ago, I never would have believed you. But here it was, happening.
We ended up watching camgirls until about three in the morning. I was the one to call it a night – I saw my sister almost fall asleep once or twice. It wasn’t until later that I realized she was probably nervous about seeming “uncool”.
As you can imagine, I didn’t get to sleep until I’d spent several hours dirtying many tissues.
After that, my sister hanging out nude became a regular thing. I actually had to go in and mess with my parent’s files again – their curiosity was low, but I suspect they’d think something was up if they wandered in to find Ashley sitting naked on my bed. I made sure that the door was closed whenever I was in a room with my naked sister, and I modified my parents’ cabinets to make “Children’s privacy” a high, high priority.
Sometimes she’d wander in with a towel, and casually drop it as soon as the door was closed – if our parents were out, she’d just wander around the house naked generally.
As well as that, she’d always invite me to come and watch her shows live.
This might shock you, but sometimes I’d decline. I knew that if I went and watched her live, it would be hours before I got to jerk off – after the show, we’d hang out on the bed and watch camgirls (there’s always some on, and you can always learn something new – even from the bad ones. Especially from the bad ones.)
As much as I loved hanging out with my naked, flushed, only-just-came sister, it sometime caused…build-up. Frustration. Blue balls. Sometimes I just wanted to jerk off while watching her strip. I’d gotten used to timing my orgasms with hers, and watching her cum without being able to even show that I was aroused was…yeah, frustrating.
After the first week, to my surprise, she sometimes went back to hanging out with my fully-clothed. I guess that at that point, she’d proved to herself (or to me) that she was comfortable with it – her “comfort with nudity around her brother” was…not sated, exactly, but no longer something she had to prove.
I guess if you’re making a point of hanging out naked with someone, it’s not something you’re “comfortable” doing. Don’t get me wrong – she was still spending a bunch of time naked, but it was no longer constant.
At the end of the second week, I think she genuinely stopped even noticing if she was naked around me or not.
That’s when I started wearing less and less around her.
At first it was just a shirt unbuttoned, or – following her lead – wearing a towel. Then I spent half a day shirtless – for the first hour or so she seemed a little uncomfortable, but she quickly loosened up.
“Comfort with nudity around Jacob”, I figured, would work both ways.
One day, she was sitting naked on my bed when I did it. I got up and stripped.
“Jacob!” she said, and then immediately tried to sound chill. “Uh, what’re you…”
“Just getting changed,” I said, shooting her an odd look. Y’know, like she was the one being weird. True to my word, I got dressed again. Baby steps.
The next day, I came into my room wearing a towel. She was sitting on my bed fully-dressed, watching a camgirl that I’d recommended (she was doing this thing where she encouraged people to send ‘waves’ of tokens – we were trying to work out if it was worth clogging up the chatroom or not). I dropped the towel, and sat beside her.
Her eyes widened, and her body stiffened slightly, but she didn’t say anything – even when I leaned in and pointed at the custom emoticon that the camgirl had set up.
We ended up hanging out for another hour that night, and by the end of it, I really think she’d forgotten that I was nude. As far as she was concerned, I was just her brother – it really didn’t matter if I was clothed or not.
After she left (and I jerked off twice), I put on some pajamas and sneaked into the cabinet room, holding a piece of paper.
It was time for the next step.