Deep Talks (With Anal)

"Who's to say when you 'should be'?"

"It's good though. The sex has been way better since we did the whole 'engaged' thing."

"Thanks for sharing?"

"Beth's happy."

"Xan, listen, you don't have to get married. And even if you do, it doesn't have to be yet. Stay engaged a while. See how it goes."

"That's the plan. I'm already worried for when she gets impatient though."

"Have you told her any of this?"

"How can I do that? She'd be crushed."

"Seems like you dug yourself quite a hole then, didn't ya?"

Xander sighed. "Yeah. I think I did. This is supposed to be fun. It's so stressful."

"Even with the good sex?"

"That helps. Lots of other stuff's good. I don't mean to imply it isn't. I'm happy with her."

"Uh huh."

"I'd be happier if... if we could just be together, you know? Why we gotta be making it a whole thing?"

"Don't ask me. She's your girlfriend. Sorry, your betrothed."

"Ugh."

I grinned. "And just think. You coulda had me instead. Never woulda been any issue about marriage."

"You mean 'cause it's mildly illegal?"

"That too, I guess. I just meant I wouldn't really care."

"At all?"

"Nah. Well, maybe I shouldn't say at all. It'd feel kinda nice everyone knowing we were together, I guess. Even if that's the impossible cherry on the already-nearly-impossible sundae."

"You still think about stuff like that?"

"Sure. Less than I used to. It helps not always having you around. It sucks too. But at least I think about other stuff. I still basically only get off to brother and sister stuff online."

"You know I don't need details like that."

"You asked."

"I did. Not that specific, but I did."

I hesitated while Xander took another drink. "There's this guy Brendan..."

"Your roommate? Or another one?"

"No. Him. He's kinda interesting."

"Oh?"

"Yeah."

"Like for real?"

"I think so. Maybe. I don't know that I could really be into him. Not like in a normal way. But he's been watching porn with me and Lily. He's kinda into that stuff too."

"... you watch porn together?"

"Yeah. Have I never said?"

"Maybe. You'd think I'd remember that, though."

"Mmm. 'Cause you do so enjoy the thought of me and Lily messing around, don't ya?"

"You continue to misinterpret things. Deliberately, I assume."

"Enh."

Xander shrugged. "Well if Brendan already knows what you're into, could be a good thing."

"Yeah. I think so."

"Makes it easier when you want to explore your kink some more. Since he already knows about it."

"Does make it easier. Never dared bring it up before." I shivered slightly even though it wasn't that cold out. "You think he'd be ok with, like, calling me his sister or something?"

"Don't know. Don't really want to know."

"Oh come on. You're curious too."

"Do you even know if he's interested in the first place?"

"Well... no. But he probably is. Boys like girls who will play with their dicks. If I offer, I'm probably in."

"I... shit. I wanted to say it's not that simple, but it definitely can be."

"Mmhm."

"That's not a solid basis for a relationship, let's put it that way."

"Who said anything about a relationship? I just wanna see if I feel anything for a guy who can... push my buttons."

"You want him to pretend to be me or what?"

I felt my face warm. "Not... not exactly. Just pretend to be a brother, maybe. That's all. He couldn't be you."

"That's a relief."

I looked at Xander, feeling self-conscious. "But you know my interest in this stuff comes from you," I said softly. "Not the other way around."

"... I guess I probably did know that, yeah."

"You made me the mess I am."

"Don't blame me for you being a little weirdo."

"I blame you."

"Fair enough." Xander finished his beer. "Ready to head back in?"

"Are Mom and Dad and Beth all still raving over her ring?"

"Probably."

"Ugh."

"Come on. It'll be fine. We'll be together."

I eyed Xander sidelong as we went back in. It was unfortunate getting excited over him saying we'd be together, when in fact the whole problem was him being together with a different girl. And yet, despite all my progress, something small like that was all it took to make me all fluttery inside.

How, after all this time, could he still do that to me?

****

It was weird to realize I'd gotten used to Brendan and having him join Lily and me in our little perv parties. I saw an awful lot of him without pants on. Mostly in the context of jerking off.

I would even go so far as to say that I kind of liked having him around. Lily had been huge for me. Having a friend who understood and empathized with my unfortunate attraction. Brendan became something similar. Not quite as important, but meaningful to me in a different way from either Xander or Lily.

Brendan was a boy who I was fairly close to, but wasn't related and wasn't trying to get in my pants. That confused me at first, but I got to really cherish it after a time. Despite us masturbating together to incest porn, we probably had the healthiest and most normal relationship I'd ever had with a boy.

It was either that comfort or some sort of self-sabotage that led me to push things, and I really couldn't tell which.

I waited until a night where Brendan and I were doing a porn night but Lily wasn't with us. Those nights were pretty rare, her being the most likely of the three of us to initiate such events.

"So hey," I said, eyes locked firmly on the screen. "Can I ask something?"

Brendan nodded, which I only caught because my attention was firmly on him in my peripherals. He was slowly stroking himself while we watched a pretend brother and sister do the initial awkward dance that would inevitably lead to sexy times.

"Go ahead," Brendan said.

"Just, like, hypothetically... how would you feel about me sucking you off?"

Brendan couldn't decide between gaping in astonishment, or smiling like a goof. Even staring more directly at him didn't sort out which emotion he was going to land on.

"How hypothetical?"

"I'd like to try it."

"Oh! Well-"

"But I don't want it to be a whole thing. Like... is it ok if we do something like that and then maybe that's it? Maybe nothing else?"

"Maybe nothing else, or definitely nothing else?"

"Maybe. Just maybe."

"Ah." Brendan wrestled briefly with the decision. "I can't pretend like I haven't thought about you a bit," he admitted.

"Really?"

"Is that surprising?"

"Maybe not. You've seen... you've seen bits of me. My pussy, particularly."

"Not often. You keep it pretty covered even when you're half naked."

I grinned shyly. "Frustrating?"

"A little. But I don't know. I like this whole... getting off together thing. I didn't want to ruin it."

"I appreciate that." I let my legs fall apart somewhat, keeping my hand well away, letting Brendan get a peek at me if he wanted. "You seem cool. Pretty chill. There's some stuff I'd like to try when there's no pressure. And I might still not really like any of it. But... I'll definitely make you cum, at least."

"That's a hell of an offer."

"Good enough for you?"

"I'll try very hard not to get my hopes up for anything more."

"Probably wise."

I wasn't convinced Brendan could stick to his promise. He already looked so awed even as I first knelt in front of him. So thrilled by what was happening. Maybe I'd misjudged and he had a serious thing for me already. But if that was the case, he'd behaved himself really well so far. That counted for a lot.

Right off the bat I enjoyed playing with Brendan's cock more than any of my previous experiences, few as they were. It was my decision. Not coerced. And I was pretty sure if I backed out, he'd be chill about it. Disappointed, sure, but not angry or annoyed.

"You're dripping some."

Brendan flushed rather cutely. "Yeah, that happens."

"'Cause of porn?"

"Sometimes. Some of these vids are pretty hot."

"What about on your own? When you pick what you watch?"

"Yeah. Sometimes then too."

"Huh. So it's nothing to do with me?"

"No, it's, uh, it's definitely about you right now."

"Yeah?"

"Yeah. Shit, I don't know if you want to hear this, but you look pretty fucking fantastic like that."

"On my knees?"

"Partly? Like, I don't know, bottomless. On your knees, yeah. And, like, looking at me all fascinated like that. And touching me."

I gripped Brendan's cock tighter, getting an adorable little exhaled sigh from him. "That's what does it for you?"

"Those are all pretty good things, sure. Plus... plus it's you. You're very easy to crush on."

I tilted my head. "Are you crushing on me?"

"Kinda? Maybe? I've never masturbated with girls like I have with you and Lily. It's... it's hard not to look. To be interested."

"In me? Or in both of us?"

"... is it bad if it's both of you?"

"No. It's better that way. This isn't about hooking up or anything, right?"

"Uh... sure?"

"So it's better if it's not just me anyway."

I started sucking Brendan before I chickened out. I didn't know what I was doing, really, except for what I'd learned watching porn, and my experience coaxing out cum with handjobs.

I didn't hate it. It wasn't directly stimulating, but there was an appeal to it. It was a fairly intimate feeling. Taking a boy in my mouth.

He loved it. I could tell that easily enough. Guys were easy enough to please by just paying any attention at all to their penises. Until they wanted more. But initially, yeah, that tended to do the trick. It was working for me, at any rate.

At least I was getting more out of it than I usually did. I felt far more in control. I'd initiated, and not through any sort of pressure I was feeling to perform or conform. It was my own choice. I could take my time, find out how I felt, and have that knowledge and experience all safely tucked away.

Brendan felt kind of weird in my mouth, but not in an unpleasant way. Just... weird. New. Different.

The more I sucked, the deeper and longer I bobbed my head up and down and caressed his shaft with my lips, the more I got into it too. I could almost say for certain that I was enjoying myself.

There was a power to it. To being in control. To making him feel good on my terms. And, of course, I was learning. I was getting a taste, so to speak.

There was an actual flavour, I found. A very subtle one to his cock itself, and a somewhat more prominent taste to his precum. I was familiar with precum, having had it over my fingers. But to taste it on my tongue was something else entirely. And I could play with it if I wanted. I'd never felt comfortable enough before to just stop and run it through my fingers, or give little licks and contemplate it in my mouth.

So much of the moment was really very nice. I didn't feel vaguely horrible about myself, which I realized I probably always had before, even if I'd tried to fight it.

"Kase?"

I looked up, startled. Brendan had been quiet for a while, other than the little moans and sighs I teased out of him. It made no sense, but I'd somehow almost forgotten he was there.

"Yeah?"

"You're gonna make me cum."

"Oh. Right."

"Is that ok?"

"That's largely the idea."

"Oh. Sure. Ok."

"How close are you?"

"Pretty close."

"Where..." I blushed. "Where do you want to do it?"

"Oh, uh, I just thought... is in your mouth ok?"

I nodded, feeling a warmth in me that really hadn't been present the whole time. Maybe it had been there in some small form, never really making itself properly know. Something about the way Brendan was looking at me now, and the way I was forced to acknowledge what we were doing, it kind of worked for me. Got me excited.

"That's fine," I said.

"And... and could you look at me?"

"Look at you?"

"Sorry. I mean, whatever you want. I just... I like when you do."

More warmth. More tingles.

"Ok," I said quietly.

I sucked Brendan harder, keeping my hand low on his shaft and squeezing some. I flicked my eyes up at him in semi-regular intervals. Had I been doing that? At first maybe I had. Then I'd gotten so focused on just his dick.

He liked it though? Why did that do things to me? I liked it, whatever it was. I liked that he liked it.

Brendan's cumshot was hot in my mouth. The flavour stronger than his precum. Way stronger. Not one that I immediately loved, but I didn't hate it. And it was so weirdly hot taking it all in while doing my best to stare up at him. He was staring right back so damn intently, until finally he shut his eyes and rolled his head back with a satisfied groan.

I took my cue to pull off his cock. I still had a good mouthful of cum. I debated what to do with it at first. Any other time, it would have been a rush to the sink to spit it out. With Brendan, in the moment, I went for it and just swallowed.

He gave an extra groan like I'd done something hot. Maybe I had. My hand was, admittedly, sneaking down to my pussy even while I sat back on my heels right in front of him.

It was easily the clearest view of me masturbating Brendan had yet received. I didn't mind. He looked, but it wasn't even a pervy kind of look. It was a look of appreciation. He liked what he saw, but didn't need to make anything of it. He was sated for the moment. And, probably, he would have been respectful enough not to ruin it for me even if he'd still been horny.

Whatever the case, I came on my knees in front of a boy while his cum still lingering on my lips, tongue, and throat. It was hot, embarrassing, mildly slutty, and just so damn good.

****

"I sucked Brendan off."

Lily looked at me, shocked just for a second or two, then grinning wickedly. "Oh yeah?"

"Yeah."

"Good for you."

"Thanks."

"How'd that happen?"

"I... I wanted to try it. And I did. He was accommodating."

Lily snorted. "Bet he was. How was it?"

"I think I kinda liked it. I'm still not quite sure why, but I've got some thoughts. I think I gotta do it some more."

"You should."

"You support me, huh?"

"Well duh. This is probably the healthiest sexual thing I've ever heard about from you."

"Sucking some dude off?"

"No, Kase. Not some dude. A dude you and I both know pretty well. Well enough, anyway. Someone you're comfortable with. Someone who presumably isn't going to be a total shit about it."

"He's been pretty good. He's hinted he'd be up for it again. I think he's really hoping it's gonna happen more. But he's been good."

"Good. If he ever isn't... I'll set him right."

I giggled. "I bet you would too."

"I got your back, you know."

"Mmhm. And I definitely appreciate it."

"Do you think you're gonna... be a thing?"

I shook my head, feeling heat rise to my cheeks. "No, I don't think so. Nothing like that. I mean... probably not."

"Ooh, but not definitely not?"

"It... it wouldn't be fair. Even if I wanted to. I couldn't promise that it'd be anything real. Not with me. You know how I am."

"Babe, no one can ever promise that a relationship is gonna work out. I know how you are. Brendan's got an idea too, remember, and he still likes you."

"He does?"

"As a friend, I mean. He'd probably go for more. I could see it. I'm just saying. He comes to our little incest nights. He's as bad as we are."

"Maybe not quite as bad."

"No. Maybe not quite."

"We'll see how it goes."

"All anyone can do."

****

Brendan was pretty dang accommodating, really. He seemed to be good with the level I wanted. It probably helped tremendously that what I wanted was to make him cum a couple times a week. It was a pretty alright deal for him.

It got better when I finally worked up the nerve to ask if he could pretend I was his sister. I'd already started pretending he was my brother while I sucked him off. Not Xander, but just some nebulous bonus brother. I didn't mention that, but he might have been able to guess.

Brendan wasn't sure what to do with the request at first, but it didn't bother him. It just took some time to figure out how comfortable he was with the pretense, and how to make it work. Once we got into a bit of a flow, it made things so much better.

"What are you doing?"

I grinned up at Brendan as I knelt in front of him. I was getting so comfortable doing it. It wasn't even something I second guessed anymore.

"You're hard."

"We can't do it out here. We'll get caught."

I almost exclusively sucked Brendan off while having porn nights, out on the couch. I'd tried in his room, but I just didn't like it quite as much in there. I wasn't sure why. Privacy should have been more important to me. But, too, it was a somewhat more intimate and personal setting, and I maybe didn't want that.

"Mom and Dad are out," I said, getting into the pretense while scooting Brendan's boxers down. His pants were already off.

Brendan took a moment, then shrugged and decided to play along. "They could come home."

"Nah."

"And Lily's still here."

I started stroking his cock, rubbing my thumb over the head to pick up any initial precum. I wasn't sure if Lily was meant to be our sister in the scenario. In my head, she definitely was.

"She won't mind."

"She might tell."

"She won't." I licked Brendan's cock, just a bare flick of my tongue, but I knew what he liked and it made him so weak and compliant for such very little effort. "Don't you want your blowjob, bruh-ther?"

"Unf."

Lily padded in, spoiling the buildup slightly as we weren't quite far enough in for my taste. She'd witnessed our blowjob sessions a couple times already, so that wasn't an issue, but I hadn't yet told her about the incest fantasy. Not that it could possibly surprise her.

"Again?" Lily asked. "You're really starting to make me doubt previous claims regarding your libido."

I tried to ignore her and took Brendan deeper in my mouth. He was blushing cutely, but still liked when I looked up at him while taking his cock. He wasn't fully used to Lily watching, but clearly was willing to make a lot of little sacrifices for the sake of semi-regular blowjobs.

"You're gonna make me want to get in on that if you keep it up," Lily grumbled settling down for some bottomless self-love, as was her wont.

I kept my eyes fully on Brendan as I pulled my lips back, leaving a soft trail of spit halfway down his cock. "Ooh, you kinda twitched at that," I said.

Brendan frantically waved like he wanted me to shut up, but it was too late.

Lily snorted. "Of course he did."

"It's like he wants both his sis-ters sucking on him."

Brendan groaned and covered his face. Lily looked at me.

"Oh really? Is that the game you're playing?"

"What did you expect from me?"

"How'd I get roped in?"

"You just said-"

"I wasn't serious."

"So just watch then."

"Yeah. Already am, thanks, since you two literally won't get a room."

I squirmed a little, partly for the game, and partly for actual arousal. It was still a novelty for me, getting wet while messing around with a boy.

"You won't tell, will you?" I said shyly.

"... what?"

"Mom and Dad. You won't-"

Lily groaned and lashed out with her foot, just barely catching my shoulder hard enough to be a rebuke. "Stop!"

"I'm sorry I'm a bad sister. I can't help-"

Lily giggled and kicked me again. "Stop. Seriously."

"She won't," Brendan mumbled.

"And you put up with it?"

"Well... yeah."

"Oh. Right. The sucking you off thing. Fair enough, I guess."

My cheeks burned. They weren't playing along, but it was still kind of ok. It wasn't quite what I wanted from my games, but it was good in its own way.

Behind the teasing and exasperation was a tacit acceptance of my kink. Neither was bothered by it. Possibly my insistence on doing stuff less privately than it could be was a very slight issue, and dragging them both into said kink, but I wasn't being rejected for any of it. Just teased some.