Chapter 15

Session 27

“Would you tell me how often you masturbate?”

“No.”

“What about if it wasn’t specific numbers?”

“Maybe.”

“Would you tell me if you masturbate more than once a day?”

“Yes.”

“ ... why?”

I know I should have just asked, but I was curious.

“I don’t want you to think I’m a slut.”

Okay. Apparently my sister’s idea of a slut was a girl who masturbated more than once a day. And she’d already kind of answered the question, but I decided to confirm anyway.

“Do you masturbate more than once a day?”

“No.”

Session 35:

“How often do you masturbate?”

“All the time.”

“How often specifically?”

“Two or three times a day.”

“And what do you think about while you’re masturbating?”

“You.”

“And what does that make you?”

“A slut.”

“Whose slut?”

“Your slut. I’m your slut.”

“You’re a slut for your brother, aren’t you?”

“Yes.”

“Say it.”

“I’m a slut for my brother.”

Session 27:

I hadn’t put my sister under for around two weeks. The last time we’d had a session, I’d changed things so that she would watch me masturbate in the bathroom, each and every morning ... and get off while she did.

It had been a total accident. But, after freaking out and working out exactly what I’d changed, I saw the perks and decided to run with it.

It was not a hard decision.

And so, for the last two weeks, I’d been masturbating in the bathroom. Every day at 8am, I’d go in and jerk off, leaving the door open—just enough for her to see what I was doing. And every morning as I came, I’d hear the muffled groans through the door of my sister getting off as well.

It. Was. Awesome.

“Spread your legs,” I said, grinning as Lucy obediently did. She was wearing a pleated short skirt—she’d been wearing a lot of them around the house lately. Almost every time I looked at her, she’d be positioned to show off her braless tits, or bending over to show me her amazing ass.

If she ever caught me looking directly at her, I knew the show would be over. I had gotten very good at checking her out from the corner of my eye.

Even while she was under, I couldn’t risk looking directly at her panties ... but while she was under, I could tell her exactly how to pose, what to do.

“Lean forward.”

She did.

“Subtly lift your boobs up so I can see as much cleavage as possible.”

You’d think that would be a risky one, but I’d caught her doing that in real life the other day. She sort of folds her arms underneath them, and suddenly there’s a whole lot of boob in my face.

I know, I know: while she’s under, I can see my sister topless. But there’s something weirdly sexy about my sister, fully-clothed, contorting her body however I want her to. Especially since I can’t look directly at her—I have no idea why that’s hot. It just is.

“Stand up and do a twirl.”

Her skirt flew up, exposing her colorful panties. I wanted to reach out and grab her ass, feel it in my hands, reach one finger around and see how wet her pussy was...

But not yet.

Not yet.

“Sit down,” I said, needing a moment to compose myself. My sister was getting off each day, watching me jerk off, and running around the house in very little clothing. Life was pretty great ... especially since Mom wasn’t objecting.

Especially since Mom had started to join in.

Session A50:

“Hypothetical. You’re twenty.”

Nod.

“You’ve just bought a dress.”

Nod.

“It shows a lot of cleavage, doesn’t it?”

“Yes.”

“It shows more cleavage than your other dresses, doesn’t it?”

“Yes.”

“Tell me how much cleavage it shows.”

“It shows a lot of cleavage.”

“Tell me where it ends.”

“Slightly above my nipples.”

“Your bust is sexy, isn’t it?”

I’d gotten to “bust” through some trial and error. Boobs, tits, breasts, even bosom—no go. But for some reason, bust was fine.

She’d say nipple, but me saying “bosom” woke her up. I didn’t understand my Mom at all.

“Yes.”

“So in this dress, they must look even more sexy, right?”

“Yes.”

“It’s sexy when men look at your bust, isn’t it?”

“Yes.”

“And so it must be even sexier when you’re wearing a dress with a lot of cleavage, because even more men look at your bust. Right?”

“ ... yes.”

Again, the hesitation. Again, she agreed. It had been quite a slog, getting to this point—I’d taken her up through the years once more. This time I’d even broken my rules, hypnotizing her twice some days. But it was totally worth it: it was working.

It was working.

“You like feeling sexy, don’t you?’

“Yes.”

“You like the sexy feeling that stockings give you, don’t you?”

“Yes.”

“Dresses that show a lot of cleavage are sexy too, aren’t they?”

“Yes.”

“It’s okay to wear sexy dresses around your family, isn’t it?”

“Yes.”

“You don’t find your family sexy, do you?”

“No.”

“So your family mustn’t find you sexy either, right?”

“No.”

That was a new one. Mom had noticed me checking out her stockings once—I’d managed to avoid leering as my sister basically showed me a tit, but I hadn’t been able to avoid checking out Mom’s stockinged legs.

And so, somewhat counterproductively, I’d brought her some science showing that people don’t find their own family members sexy. It’s called the Westermarck effect—it mostly applies to brothers and sisters (I guess I’m just broken) but I’d convinced Mom that it meant that I didn’t find her sexy, and so she had continued wearing stockings around the house.

“You like how sexy your bust is, don’t you?”

“Yes.”

“And so you must love how it looks in your new dress.”

Nod.

“You decide to wear your new dress whenever you can.”

Nod.

“You get more dresses that show lots of cleavage.”

Nod.

“Any chance you get, you wear dresses that show lots of cleavage.”

Nod.

“Except when you’re at work, you’re almost always wearing dresses that show lots of cleavage.”

Nod.

“You like showing a lot of cleavage, don’t you?”

Nod.

“Say it.”

“I like showing a lot of cleavage.”

“It’s okay to show a lot of cleavage around family, isn’t it?”

Nod.

Session 27:

I knew my sister was getting off once a day while watching me. And she’d just admitted that she didn’t get off any other time.

The only time Lucy came was while watching me do the same ... that was definitely something I could use.

“Okay,” I said. “Hypothetical: every morning at 8am, you stand outside the bathroom and watch me jerk off.”

Nod.

This obviously wasn’t a hypothetical: it was really happening. In real life. I sometimes still struggled to process it. It was really happening. It had been a total fluke, but man ... what a lucky thing to fluke upon.

But I knew she wouldn’t talk about it if I flat-out asked, so I had to play the hypothetical.

“Every time you watch me cum, you get off as well.”

Nod.

“One day...”

I paused. I’d worked out what I needed to do next just a few days after everything had started. But even though I knew it would get me closer to my goals, it felt like a step backwards, and so I’d held off. There was something so hot about knowing my sister was outside the bathroom, her hand down her pajama pants or up her nightgown, getting off in time with me, cumming at the site of my cock shooting off...

Part of me never wanted to stop. But sometimes the only way to go forward is to go back, and so I knew I had to do it.

“One day, you go to the door of the bathroom at 8am ... and I’m not in there.”

Nod.

“You go and find me—I’m in the lounge room, sitting in Mom’s armchair watching TV.”

Nod.

“What do you do?”

“I tease you.”

It came out in a monotone, as always, such a matter-of-fact statement. But her hand twitched as she said it, like she wanted to reach down and flash me the front of her panties (as she’d done a few times before, when she was feeling particularly cheeky.)

“How?”

“I sit on your lap,” she said, to my surprise. Up until now, her teasing had been mostly visual. There had been the occasional boobs pressed against my chest, or butt against my crotch as she squeezed past (it had been a hell of a challenge to avoid getting a boner, which I knew would stop the show immediately) but she’d never been this direct.

“I sit on your lap and ask what you’re watching.”

I could have gone down that train of thought a bit longer (last time I’d followed a whim, it had accidentally been quite rewarding) but I had a lot I wanted to get through in this session, so I pressed on.

“You don’t get off that day.”

Nod. I didn’t know her masturbation habits, but I figured “you don’t jerk off” was a pretty safe part of any hypothetical that didn’t include Johnny Depp.

“The next day, the bathroom is empty at 8am again.”

Nod.