Chapter 14

Now, I know what you’re thinking—you’re thinking there’s a path clearly laid out for me. For the first time, I could engineer sexual contact with my sister ... without having to break both my arms.

All I’d need to do would be have her catch me crying, convince her I’d never been kissed, and get her to make out with me. I could plant fleas in my room and sleep in her bed, hope she had an erotic dream about me, and make out with her in the morning.

And you’re not wrong. I could have done all of that. But I didn’t know where it would go. If I wanted to make out with her, I could do it while she was under, with the added bonus of getting to use her huge tits as cum target practice a few minutes later.

No, when stuff started in real life, I wanted it to be more than kissing, more than sleeping in the same bed.

I wanted it all.

Session A33:

“Okay Mom. Hypothetical—you’re seventeen years old. You’re hanging out with a bunch of your girl friends, and they’re all talking about the part of the body that they hate the most. It gets around to you. What do you say?”

There was a pause. A long, long pause. A pause so long that I was worried Mom was going to wake up ... but finally, she answered.

“Probably my elbows.”

I grinned. The baby steps had added up: I was getting somewhere.

Session 26:

It was tricky, working out my sister’s limits. And not just stuff she definitely wouldn’t do—that bit was easy.

Stuff that she would almost do, that was the trick. Because once you’re right at the edge of someone’s limits, you can nudge it. A kiss becomes a french kiss ... helping someone masturbate becomes watching them masturbate.

I wanted to fuck my sister. I mean, ideally I wanted to fuck her while she was awake, while she knew exactly what was happening. But I didn’t know if that day would ever come, and so until then, I’d settle with fucking her while she was under.

The trouble was, I had no idea how to get to that stage. Last time, I’d managed to convince her to dry-hump me ... while she was hypothetically asleep. I could kiss her, I could even get her to make out, but anything beyond that...

So until a path presented itself, I decided to focus on what I had.

“Would you tell me if you like to tease people?”

“Yes.”

“Do you like to tease people?”

“Yes.”

Interesting. It seemed my sister had a bit of an exhibitionist streak. That put the nude beach hypothetical in a whole new light...

I wondered how far she’d gone with it.

“Would you tell me if you’ve ever flashed anyone?”

“Yes.”

“Have you ever flashed anyone?”

“Yes.”

“Who?”

“Marcie’s Dad.”

“Go on...”

“He was in the kitchen when I was in the pool with Marcie once. I pretended that I didn’t know he was there, and took my top off.”

“Have you ever flashed anyone your ... you know, your pussy?”

“No.”

“Why not?”

“I don’t like it.”

Women. I genuinely don’t understand them. I’ve not once encountered a vagina that wasn’t supremely attractive, but just like Mom and her legs, it turned out that Lucy had a thing about her pussy.

That at least explained why it had been so (relatively) easy to get her top off.

Session A36:

“Okay Mom, hypothetical: you’re 20 years old. How do you feel about your legs?”

“I like them.”

“Why do you like them?”

“Because they’re sexy.”

“Have you ever worn stockings?”

“No.”

“You buy your first pair of stockings.”

Nod.

“You put them on. How do they feel?”

“Good. Smooth.”

“How do they look?”

“Good.”

“No they don’t. They look great. You thought your legs were sexy before, didn’t you?”

“Yes.”

“Well now they’re even sexier.”

Nod.

I paused, wondering how far Mom would let this hypothetical go. Whenever I’d so far as mentioned sex in the past, it had woken her up. As a hypothetical twenty-year old, however, she might be a bit more open-minded...

“Just looking at your sexy, stockinged legs starts to turn you on...”

“You really are good at this! Thanks so much for that...”

Ah well. Nothing ventured, nothing gained.

Session 26:

“So teasing turns you on?”

“Yes.”

“And hypothetically, you’d tease your brother?”

“Yes.”

It felt like saying “your brother” instead of “me” added a tiny bit of distance, made her more likely to say yes. I had no evidence of that, of course, but I figured it couldn’t hurt.

“Okay Lucy, tell me: when would you tease your brother?”

“If I knew he wouldn’t notice.”

“But how could you know that he wouldn’t notice?”

There was a pause as she considered the question. I had to admit, it was a tricky one. After ten seconds had passed, I decided to give her a hand, if only to ensure that she wouldn’t wake up.

“What if you were to tease just a little. Just enough that if I did notice, it looked like an accident. Is that something you might do?”

“Yes.”

“Okay: hypothetical. You start to tease me— ... your brother a little. Just a tiny bit, nothing too obvious.”

Nod.

“I don’t notice.”

Nod. It was almost sweet, how innocent my sister thought I was.

I guess it’s a credit to how well I hid my true intentions, considering the dirty things I’d gotten her to do ... and the even dirtier things I was planning.

“After a week or so, you begin to step it up a bit.”

Nod. “Step it up” was a bit of a vague term, but I was going to circle back later and get the details. Right now, I wanted to see how far I could push this.

“I still don’t notice.”

Nod.

“Would you tell me how it feels to tease someone?”

“Yes,” she replied, quietly but monotonously.

“How does it feel?”

“It turns me on.”

“How does it feel to expose your skin to someone who doesn’t even notice what you’re doing?”

“It turns me on.”

My sister almost seemed to have an ... innocence fetish? Is that even a thing?

“How does it feel to expose more than you should to your brother?”

I continued before the pause could get too long. I didn’t want to wake her up—not yet.

“Would you tell me how it feels to tease your brother?”

“Yes.”

Even quieter than before.

“How does it feel to tease your brother?”

“It turns me on.”

I was so hard, and my sister’s boobs were just one command away ... but I had to keep going. I needed to know how far she’d go.

“You keep on teasing me.”

Nod.

“Do you own any short skirts?”

“Yes.”

“You start wearing them around the house.”

Nod.

“You stop wearing a bra when it’s just us at home.”

Nod.

“When you’re wearing a short skirt, you’ll find excuses to bend over in front of me.”

Nod.

“No matter what you do, I don’t seem to notice.”

Nod.

“That just turns you on more and more, doesn’t it?”

Nod.

“You make sure that Mom doesn’t catch you.”

Nod.

“You make sure she doesn’t suspect a thing.”

Nod.

“But a few times a day, just for kicks, you’ll tease me around the house.”

Nod.

“Confident I’ll never even notice.”

Nod.

Amazing.

Session A37:

So obviously going sexual wasn’t going to work—it would wake Mom up. But just like Lucy could find Mom sexy without being attracted to her, Mom was okay to talk about things being sexy...

“Okay Mom, hypothetical. You’re twenty, you’ve just bought your first pair of stockings, they make your legs look sexy.”

Nod.

“Your legs look sexy by themselves, don’t they?”

“Yes.”

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

“Yes.”

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

“Yes.”

“And so it must be even sexier when you’re wearing stockings, because even more men look at your legs. Right?”

“ ... yes.”

There was hesitation there, but she did agree.

“You like feeling sexy, don’t you?”

“Yes.”

“You like how sexy your legs are, don’t you?”

“Yes.”

“And so you must really like it when you’re wearing stockings.”

Nod.

“You decide to wear stockings more often.”

Nod.

“You decide to wear stockings whenever you can.”

Nod.

“Any chance you get, you wear stockings, and they make you look and feel sexy.”

Nod.

“You’re almost always wearing stockings.”

Nod.

I slowly woke her up, and after a few confused blinks, she smiled and thanked me for the session.

At breakfast the next morning, she was wearing a long dress—nothing new or unusual, it was something she’d had for years.

But underneath, she was wearing stockings.

Session B34:

In the meantime, I’d been increasing Marcie’s obsession with me more and more. I’d also made sure to emphasize how important it was that she appear normal to everyone else—if Lucy found out that her best friend was suddenly sexually obsessed with me, she was likely to be at least a tiny bit suspicious.

At the risk of sounded big-headed, I was genuinely impressed by how far I was able to push Marcie. Maybe she just has a naturally pliable mind, but considering how quickly I’d managed to turn her slight crush into the equivalent of Beatle-mania, combined with the forward steps I was managing to take with my family ... well, I felt like I was really starting to get the hang of this.

“Who owns your pussy, Marcie?”

“You do.”

“Who owns your mouth?”

“You do.”

“Who owns your body, Marcie?”

“Y— ... you do.”

There was a bit of hesitation there, but I wasn’t too worried. It wouldn’t take too much effort to eliminate that.

“Who owns you?”

There was a longer pause this time, but when the answer came back, it was firm and steady.

“You do.”

It hadn’t taken much to turn Marcie’s obsession with me into a slave obsession. Now when she masturbated, she didn’t just think about my pleasure—she thought about me owning her pleasure.

“Who decides when you cum, Marcie?”

“You do.”

“Who decides who you fuck?”

“You do.”