More Limits

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.

"You come and find me—this time, I'm in the kitchen, making breakfast. What do you do?"

"I come up behind you and give you a hug from behind."

Interesting. Maybe watching me jerk off made my sister feel some kind of connection to me, and when that connection was missing, she used physical affection to duplicate it.

Or hell, maybe she was just horny. I made a mental note to check if she got touchy-feely when she was horny.

"You don't jerk off that day."

This time there was a slight pause before the nod. I think after getting off every day for two weeks, you get kind of used to it. I know that before I started playing with her, Marcie used to only get off every couple of days, and now—based on her texts—she cums once a day thinking about me, if not more.

(Marcie was away with her family for a month, which was both a curse and a blessing. On one hand, I missed using her to get off. On the other, it meant I was so built up that cumming each morning in the bathroom was easy and fast—I didn't want to take too long, in case Mom caught us, or Lucy got self-conscious and stopped her peeping.)

"The next morning, you're super horny."

Nod. Instant, very emphatic nod.

"You go to the bathroom door at 8am, but I'm not in there."

Nod.

"You can't find me in any of the public rooms of the house."

Nod.

"You walk to my door, and you notice that I'm laying on my bed."

Nod.

At this point, I was again torn. A part of me wanted to keep on keeping on, just move the voyeuristic activities to my bedroom. But that wasn't the path that would lead me where I wanted to end up.

And so instead I followed the plan that I'd spent the last week coming up with.

"I'm having a nap."

Nod.

"You go to your room."

Nod.

"You're really turned on and you want to cum."

Nod.

"You start to play with yourself..."

Another nod. I hadn't even finished the sentence: that's how keen she was for a hypothetical orgasm.

"...but no matter what you do, you can't cum."

Pause. Long pause. And then, after the pause was so long I was worried she was going to wake up, my sister shook her head.

"Why not?"

"I've never had any trouble reaching climax when I play with myself," she said. "Especially when I'm turned on."

Damn.

"Okay, but..."

I trailed off. I hadn't thought about this—I can tell my sister whatever I like about my own sexual habits, but when it comes to her own, she's indisputably the master.

"Okay," I said, after a few moments of thought. "Ummm...new hypothetical. We're on vacation at the caravan park, your iPod breaks, and there's a blizzard outside..."

Over the next minute, I summarized the hypothetical from one of our earlier sessions. Lucy nodded: suddenly, we were in the world of knowingly, deliberately getting off in front of each other.

"Would you tell me if you like getting off in front of me?"

"Yes."

"Do you like getting off in front of me?"

"Yes."

"Would you tell me why?"

"No."

"Would you tell me if you find it harder to get off when I'm not around?"

"Yes."

"Do you find it harder to get off when I'm not around?"

"No."

"Would you tell me why you like to get off with me, then?"

"No."

Another dead end.

Damn it.

Session A51:

"Okay Mom, hypothetical. You're eighteen."

Nod.

"You see a nice woman's shirt in a catalogue."

Nod.

"It shows off her midriff, and it looks really pretty."

Nod.

"You look at your midriff. It's quite pretty, isn't it?"

Nod.

"In the same catalogue, there's a sexy nightgown. There's a nightgown that's lacy and see through, and it shows most of the woman's body. Do you understand?"

"Even her privates?"

"Yes, even her privates. Do you understand?"

"Yes."

"You think it's really pretty."

Nod.

"You want to get one just like that when you grow up."

Nod.

"It's fine for family to see your privates, because they're family."

Nod.

"It's such a nice nightgown. You can't wait until you grow up, so you can get one of your own."

Nod.

Session 27:

I was totally stumped. My plans had been thwarted by, of all things, how good my sister was at getting off.

Unless...unless that was something I could use.

"New hypothetical!" I said, suddenly inspired. I glanced at the clock—this might take us over the half-hour, but I hadn't put her under for two weeks. I was pretty sure she wouldn't noticed if I stretched the limit a bit.

"Every morning at 8am, you stand outside the bathroom and watch me jerk off."

Nod.

"One day, you go to the bathroom, and I'm not there. You find me in my room—I'm just laying on my bed."

Nod.

"You still want to get off, so you go to your bedroom."

Nod.

"When you start playing with yourself, your mind turns to what you've been looking at as you get off for the last few weeks."

Nod.

"As you cum, you imagine me getting off."

Nod.

Wow. No resistance at all. Maybe I'd still be able to make it in under half an hour...

"The next morning, when you come to the bathroom, I'm not there."

Nod.

"You realize I didn't come and thank you at all the day before."

Nod.

"What does that mean?"

"It means you haven't jerked off."

"That's right. You go to your room and get off again."

Nod.

"As you do, you think of me."

Nod.

"You think I'm very sexy, don't you?"

"Yes."

"You like thinking of me cumming when you cum, don't you?"

"Yes."

"I don't come and thank you again all day."

Nod.

"The next morning, I'm not in the bathroom at 8am."

Nod.

"You go to your room and get off, thinking of me."

Nod.

"Every time you get off, you think of me."

Nod.

"What do you think about when you get off?"

"You."

"What specifically?"

"Your cock. Your cock, cumming."

I smiled. I felt like I'd pushed through another limit, somehow.

"The fact that I'm not masturbating—how does that make you feel?"

"Bad. Worried."

"Does it make you want to help?"

"Yes."

"How?"

There was a long pause as my sister thought. I decided to help her out a bit.

"Does it make you want to tease me more?"

"No."

That was a surprise.

"Why not?"

"Because you don't really notice when I tease you."

Ah, of course. My sister's teasing, as far as she's concerned, is for her, not me. If she thought it would be helpful, she certainly wouldn't do it.

"Does it make you want to help me get off?"

"Yes."

"Does it make you want to...jerk me off?"

"No."

"What, then?"

"It makes me want to find out why you're not getting off and help you with that."

Interesting. Not quite what I was going for, but I'm not one to look a Trojan horse in the mouth.

It was time to wake my sister up. The session was about to run over, and I wanted to wake her up slowly and implant the memory of her getting off every day, thinking about me.

Yes, it meant the end of our real-life mutual masturbation sessions, but they were technically one-sided anyway. She was watching me—I didn't get to watch her.

I was trying not to think of it as a step backwards, but a leap forward in a more useful direction. I'd replaced it with something almost as good: the knowledge that every day, my sister was in her room, playing with herself, thinking of me as she came.

I hadn't gotten as far as I'd hoped, but I could hardly complain.

Session A58:

"Any time you're at home and you're not wearing a low-cut dress, you wear skirts and tops that show midriff."

Nod.

"Every night, you wear transparent, lacy nightgowns."

Nod.

"It's okay for family to see you in them, isn't it?"

"Yes."

"It's okay for family to look at each other's bodies, isn't it?"

"Yes."

"It's okay for your son and daughter to look at each other's bodies, isn't it?"

"Yes."

"There's nothing wrong with that, is there?"

"No."

"Is it okay for Lucy to start wearing short skirts around the house?"

"Yes."

"Is it okay for her to look sexy?"

"Yes."

"Is it okay for her to wear transparent, lacy nightgowns?"

"Yes."

"Is it okay for her brother to look at her body?"

"Of course."

Session B112:

Marcie's father was out when we dropped by. She'd only been institutionalized briefly—the doctors had quickly determined that she wasn't a threat to herself or to others, and though she needed a carer, she didn't require constant supervision.

Her mother was long gone, but her father was still around. He seemed like he was really struggling—the few times I briefly ran into him, he just thanked me for coming to visit his daughter.

"At least we know who her true friends are," he'd said once, as if I needed to feel any worse.

"Hey Marcie," I said, eliciting no response until I stepped forward and cupped her breasts. She moaned at my touch, as I knew she would. "Your master is here."

Session 28:

"Hypothetical: when you masturbate, you think about my cock."

Nod.

I'd expected her to accept that, but it was good to know that we hadn't gone backwards since last week.

"You think about how frustrated I must feel..."

Nod.

"And how awful it must be, not being able to cum every day like you do."

Nod.

"You think I'm very sexy, don't you?"

"Yes."

"You think your brother is sexy."

Nod.

"How does it make you feel, knowing that he isn't cumming as often as he should?"

"Sad."

"Does it make you feel frustrated?"

"Yes."

"It's frustrating not being able to cum, isn't it?"

"Yes."

"When you're masturbating, you think about how frustrated I must feel, and you start to feel it as well."

Nod.

"You can't cum, because you know I can't cum."

Shake.

Not even a pause. Just an instant rejection of the hypothetical. I paused—that wasn't what I'd been expecting.

"You have no trouble cumming, even though you know I can't?"

"Yes."

"It doesn't affect it at all?"

"No."

"Why not?"

I swear I saw a proud smile appear on my sister's otherwise-neutral face as she replied.

"I never have any trouble cumming."

Damn it.

I mean, on one hand, that was super hot to hear—and think about. Apparently my sister came easy...good to know.

But it did make my job a bit harder.

As far as my sister was concerned, I'd abruptly stopped masturbating. No longer could she spy on me from outside the bathroom door, secretly getting herself off as she did.

I was hoping to leverage the fact into stopping her orgasms as well, leaving her horny, desperate to make me cum so that she could as well. No such luck.

We sat there in silence for a few seconds, as I hastily constructed a backup plan.

"Okay," I said eventually. I had a new path to go down; hopefully this one wouldn't be stymied by my sister's easy orgasms.

"When you masturbate, you think about me."

Nod.

"You think about me wrapping my hand around my cock and stroking it until I get off."

Nod.

"When you cum, you imagine me cumming."

Nod.

"But even while you're having an orgasm, you know that it's been a week since I got off."

Nod.

"That makes you sad, doesn't it?"

"Yes."

"Your orgasms aren't as good when you're sad, are they?"

There was a slight pause, and for a second I thought my sister was going to admit to being some kind of sex robot, always able to cum powerfully, no matter what else was happening in her life.

Which would be, y'know, fun. But distinctly unhelpful. My sister the sex robot.

"No," she finally answered, and I smiled.

"When you're sad, your orgasms aren't quite as satisfying, are they?"

"No."

"So once you've cum, you're still a little bit horny, aren't you?"

"Yes," she answered—again, there was a slight pause, but I think what I was saying made too much sense for her to deny it.

"When something is unsatisfying, it means you want more, doesn't it?"

"Yes."

I was going to be the first person to fuck his sister through use of dictionary definitions.

"So after you've had something that's unsatisfying, you want another one."

Nod.

"And if that one is unsatisfying, you want another one after that, right?"

"Yes."

"So if you have an unsatisfying orgasm, you want to have another one straight after, don't you?"

"Yes."

"Would you tell me the most number of times you've orgasmed in a day?"

"No."

"Would you tell me if it's more than five?"

"Yes."

"Have you ever had more than five orgasms in a day?"

"No."

"Would you tell me if it's more than three?"

"No."

I had a ball-park figure, at least. Time to bring it all together.

"So when you know I'm not masturbating, it makes you sad."

Nod.

"And when you play with yourself, you think about my cock."

Nod.

"So whenever you masturbate, you get sad because I'm not, and it give you unsatisfying orgasms."

Nod.

"After you cum, you have to cum again."

Nod.

"And after that, you need to cum again and again and again."

Nod. I had hoped that by leaving the number vague, it wouldn't trigger my sister's reluctance to share exact numbers...but "again and again and again" sounds like it's at least three times to me.

"Every day, you cum a number of times, but you're never satisfied."

Nod.

"You're still horny after you cum."

Nod.

"That means you're horny all the time, doesn't it?"

"Yes," my sister said in her soft monotone.

I could have woken her up here—the idea of my sister walking around all day, horny and unsatisfied, even as she flashed her little brother...it was tempting.

But I wanted to push it further than that. She was squirming slightly in her seat at the scenario I was putting in her head, of her wandering around all day turned-on and unable to do anything about it.

I was pushing her limits further than I'd ever pushed them before. I could feel it.

Session A60:

"Mom?"

Nothing.

"Mom, can you hear me?"

Silence.

"Mom, answer me. Can you hear what I'm saying?"

No response.

I had absolutely no idea how to deal with what had just happened—I'd come home to find my mother flipping through a photo album, tears running down her face, struggling to breathe.

I'd panicked, and put her under. She hadn't resisted as I went through the usual routine, and now she was sitting in front of me, staring blankly, not saying a word.

"Okay Mom. What's your daughter's name?"

Nothing.

Shit.

Shit shit shit.

"Mom?"

Session 28:

I ran the situation from a few different angles before I continued, making sure I really let it sink in.

"It's frustrating, walking around horny all the time, isn't it?"

"Yes," Lucy replied, and even though her voice was completely expressionless, I could see the desperation in her eyes.

"Okay. One day, you're walking past my room and you see me inside, crying."

Nod. Her facial expression immediately softened. For whatever reason, my sister is an absolute sucker for her little brother's tears. If I could fake-cry in real life, I bet I'd have her in bed within a week.

"What do you do?"

"I walk inside," she said, "sit on your bed, and put one arm around you."

"I'm still crying. What do you say?"

"What's wrong, bro?"

Session A60:

"What's wrong, Mom?"

She just sat there as she had for so many sessions before now, staring blankly. She was dressed in what was becoming one of my mother's standard around-the-house outfits—a white button-up vest that showed off her plentiful cleavage, and a black skirt that ended just above her knees.

It was sexy as hell, but in that moment, I barely even noticed. I was wracking my brain, trying to get my mother to talk.

"Would you tell me what's wrong?"

Nod.

She nodded! That was something. I picked up the photo album, still sitting open on her lap. As I looked through it, my heart sank.