Stepbrother With Benefits 17 (Third Season) (18 page)

C
aleb and I watch a movie
. We sit on his bed at first, but then it's kind of cold so we get under his blankets. We lay like that, side by side, his laptop between us.

I wiggle my toes and poke them against Caleb's. He turns and gives me a funny look. I stick my tongue out at him and wiggle my toes more. He wiggles them back this time. We start to have a foot war, our feet fighting for dominance beneath the covers. I'm not sure what's going on with the movie, but we're kind of ignoring it now. The laptop bounces as our feet shift back and forth.

I start to play dirty and use my hands, trying to tickle him. Caleb bursts out laughing, but then he catches on and grabs my hands. I wish his hands weren't so big, or maybe I wish mine weren't so small, because he can easily hold both of mine in one of his, which really isn't fair.

He holds them both and grins at me, wicked and devilish. Then he stops for a second, going back to normal.

"Hey, hold on, time out for a second, alright?" he says.

"Sure," I say, pausing our foot fighting.

Caleb grabs his laptop and sets it on his desk near the bed.

"Oh, good idea," I say, nodding my approval.

"Time in," Caleb says quick before I can react.

He grabs my hands again and holds them tight, then flips on top of me, pinning me to the bed. He laughs as I squirm beneath him, struggling to get free. I kick my legs, but I have nothing to kick at now. He's straddling my hips, keeping me trapped, both of my arms held above my head in one of his hands while his other hand...

Oh, fuck, he's going to tickle me. I'm too fucking ticklish, too. Why did I start this? I hate being tickled! The worst part is I know Caleb knows I hate being tickled, and now he's going to do it to get back at me. And, you know what? I don't blame him. It's probably what I would do, too. I'm the one who tickled him in the first place, so it's kind of already what I did.

I need to fight back. I need to think of a way to stop him. He looms closer, grinning at me like a madman, his free hand slowly inching its way towards my side. I can feel his fingertips pressing against the thin fabric of my shirt, creeping lower towards the bottom, reaching for my bare skin. I...

I do the only thing I can think of. I move up, pucker my lips, and I kiss him.

Time stops. Or we stop. A lot of things stop. Maybe everything stops?

Which is kind of what I was hoping for, because it means Caleb isn't going to tickle me anymore, but, um... I guess I didn't expect the severity of it all? Did I break something? I'm not sure.

I kiss him on the lips, just straight on, but when he stops moving to try and tickle me, I kiss him again. It's soft, but a little more this time. More...
active
. More like a real kiss, and not just a simple peck.

He kisses me back, but it's slow, almost guarded. I'm not sure if this is a part of my plan for this game or what. We were wrestling and play fighting, and I still kind of want to win, except I'm not sure what I want anymore.

Caleb's hand touches my side, but he's not trying to tickle me this time. He moves his hand under my shirt and presses his palm against my bare skin, teasing up my side. My skin prickles under his touch, electric and excited. My hips move up, grinding against him a little. He still holds both my hands in his, keeping them pinned above my head.

I struggle to free my arms and he lets me go. When my hands are my own again, I move quickly and grab his cheeks. I pull him towards me, kissing him harder, faster, with more passion. He kisses me back, his fingers pressing hard into my bare skin under my shirt, squeezing my side. It tickles a little, but not too much. I squirm under his touch, a laughing smile curling across my lips.

He smiles, too. We open our eyes and look at each other, both of us a little unsure, slightly confused, but...

While he's caught off guard, I push him off of me. He tumbles onto his side, but I keep up the momentum and shove him onto his back. I straddle him now, gaining the upper hand. He looks up at me and shakes his head, laughing.

"You think you're good, huh?" he asks. "I'm not sure if you realize this, but there's no way you're strong enough to pin me to the bed, so..."

He starts to pick me up and off of him. No! I... I went all this way, and I plan on winning, so I need to think of a new plan.

Which I do. I don't know why I think of this specific plan, but it's just the first thing that comes to me. I can't say it's good. I don't know if it's bad, either. It's a plan, alright? I'll figure it out later.

I'm on top of Caleb while he's laying on the bed. I'm straddling his hips, and he's moving his hands to grab me and pull me off of him. I have no real chance against him, unless I...

I grind and rock my hips against him, pressing my core into his crotch. Like I suspected, our kiss was a good beginning, but this is a whole lot more. I rock and grind against Caleb's ever-hardening cock. He forgets what he's doing and drops his hands to his sides, closing his eyes and pushing his hips up. He grunts, then falls back, letting me grind against him.

I mean, we both have our clothes on this time, so there's no chance for any accidents like before. I think that's a good thing, but I'm not so sure. I...

This actually feels really good, too.
Oh, wow.
Um...

I can feel him growing harder and harder beneath me until I'm pretty sure he's as hard as he can get, at least with pants on. There's only so much room to grow, right? I think that's how this works.

I don't really have any growing going on. It just feels good, and good, then more. It's kind of rough, our pants grinding against our bodies, the fabric pressing tight against my pussy and my clit. Yeah, um...

"Caleb, I need to stop," I say, throwing myself off of him.

I roll off the bed and tumble to the floor. Oh my God, I don't even know what's going on. I crawl and scramble across the room to my new bed, then I flip back the blanket and jump in. I pull the blanket over me and all the way up to my chin.

Caleb blinks hard, staring at me from across the room. I look at him, too, all while hiding beneath my blanket.

"Sorry," I say. "I know you got upset before, and I didn't mean to...
you know
. I don't know what happened. I was just trying to win at wrestling with you."

"It's--" He starts to say something, but I don't know what. He stops as soon as he starts, and then he just lays there, conflict glimmering in his eyes.

"It's cool," he says after a few seconds. "Uh... maybe we need to figure this out. Figure out what we're doing. Uh... with your school thing, I mean."

"I think it's fine," I say, fast.

"You do?" he asks.

"I think it's fine if we try some things out because it'll help with my art project," I add, clarifying.

"Oh, yeah, right," he says. There's something weird about the way he says it, though.

"Just... maybe we need to figure out how we're going to do this?" I say. "I mean, so... in the video, we're going to have sex. Real sex."

"Yeah, of course," he says, nodding.

"It's just... people don't jump right into having sex most of the time, you know?"

"Right," he says. "There's build up."

"Exactly!" I say, nodding fast. "There's kissing, so it's fine that we kissed. It's good practice for the movie. There's also touching, so it's alright for us to do that. I think it'll be great for the movie if we have chemistry, so being playful together is good. It's just... since it's for the movie and everything, maybe we need to work our way up to more? Maybe we should go slow or something?"

"Uh... sure?" Caleb says. "I don't know what you mean by that."

"We're friends and I feel really comfortable with you, Caleb."

"I know," he says. "Me too."

"Maybe that's what's getting in the way? We're worried that we're going to make each other feel uncomfortable?"

"Yeah, actually, I do kind of feel like... like maybe that could be happening."

"I know, right?" I say, because it's totally true. I'm glad we feel the same way. "So... what if, instead of just... you know, um... letting ourselves get, um... away with ourselves. Instead of that, what if we just do something that's uncomfortable but we talk it out ahead of time. Then we'll know what's going on and we'll know that we don't have to worry about making each other feel uncomfortable."

"You mean, like... if I kiss you, then I'll tell you I'm going to kiss you first?" he asks.

"Yup! Just like that!"

"Alright. When should we try that?"

"Right now?" I offer. When he looks a little surprised, I add, "Or later! We can wait. There's no rush."

"We can try right now," he says, quickly. I think he's trying to reassure me, which is nice, because I have to admit I'm a little nervous about this. "I don't mind."

"Alright," I say. "I have an idea. I think it'll help. Want to try it?"

J
ust in case
you didn't know, Scarlet's ideas are always bad. I'm not saying that to be an asshole, either. I like Scarlet a lot. I've known her for forever now, and I've been a part of more of her bad ideas than I care to admit.

They're bad. Nothing good ever comes from them. Sometimes everything works out in the end, so I guess you could say they aren't the worst ideas ever. There's nothing terrifying about them, either. She's very subtle and nuanced in how she explains her ideas. If you heard one, you may even think it sounds like a pretty good idea.

No. Trust me. It's probably a bad idea. You might end up having a lot of fun while you're doing it, but by the end you're going to question why you ever agreed to do any of this in the first place. That's just how it is.

I even made up a rule about it. It's just my rule, and I haven't shared it with anyone else, but...

Scarlet's Law - Any plans Scarlet has will inevitably end with something bad happening. It is probably exactly what you'd expect, even when she claims that this could never possibly happen. It will happen. Trust me.

Which begs the question... why do I still go along with them?

I don't know. It's a little more complicated than that. I think I've put too much time into our friendship already that I can't back out now. I mean, really, what are the alternatives? Scarlet's still my best friend, even if her ideas are kind of terrible...

"Where should we sit?" she asks me.

"Uh... I don't even know what we're doing yet," I say.

"How about your bed?" she asks, getting out from under her blanket and scurrying across the room.

She joins me on my bed, just hops right onto it, sitting crosslegged and staring at me. Then she says the one thing that can completely melt any reluctance or resistance I have about her and her bad ideas.

"Thanks for helping me with this, Caleb." And she smiles at me, looks at me like I'm the only person in the entire world that she can rely on. "I... I don't think I could do this with anyone else. Not like this. Um..."

"Sure," I say. Yes, my resistance is melted, but I'm not going to let her know that. If I do, that's exactly when the plan will become even worse. Let's try to mitigate how much bad stuff can happen, alright? "I still don't know what we're doing, though."

"Right," she says, nodding fast. "So, the thing is, we need to figure out how to pretend to be boyfriend and girlfriend for my art project."

"Yes," I say, nodding. Just one nod.

"How do boyfriends and girlfriends act with each other, though? We need to work on that part."

"Uh... they hold hands?" I say.

Scarlet pushes her way across my bed until she's closer to me. We're facing each other. She puts out her hand, and I give her mine. We wrap our fingers together and hold hands like that, except, uh... it's kind of weird? I mean, we're facing each other. This kind of feels more like a children's game you play when you're younger, you know? Like patty cake or something?

"Come here," I tell her, tugging on her hand and motioning for her to sit next to me.

She smiles and scoots closer. Now we're side by side, sitting close, holding hands.

"This is cute," she says. "You know what I've always thought is really cute? When you see a couple, right? You see them walking and holding hands but they're just kind of swaying them back and forth. It's cute and carefree and I think it's nice. Maybe we should do that sometime?"

"Uh... so you want to hold hands in public?" I ask her. "People are going to get the wrong idea."

Why did I say that? I have no idea why I said that. Wow.

"Yeah, true. Maybe we could try it sometime on the weekends, though? We can go somewhere else where no one will see us. No one we know, at least. That way we can practice holding hands in public but it won't be weird."

Seriously, why did I say that? I could have been holding hands with Scarlet all the time at school, and now I can't. I guess we have the weekends still, but I don't even know where we could go for that.

"Couples kiss, too," she says. "Like we did before, but..."

She turns and looks at me, expectant. I look over at her. She bats her eyelashes at me, but doesn't do anything else. I keep looking. She keeps batting her eyelashes.

"You should kiss me now," she says. "Caleb, you aren't even taking this seriously! How are we going to pretend to be boyfriend and girlfriend for my art project video if you don't take this seriously?"

Alright, fine! If that's what you really want, Scarlet...

She's about to say something else, but I stop her with my lips. I kiss her, firm. There's nothing extreme about it, not yet. It's not as passionate as before, but it's definitely a kiss and it definitely shuts her up. I wasn't even trying to do that last one, but I guess it's a nice added bonus.

Her lips part and she kisses me back. Oh. Uh... yeah... that's nice...

I squeeze her hand in mine and kiss her. Our lips go so well together. I tease her bottom lip with the tip of my tongue, and she grins. Our eyes lock for a second, but then she closes hers. I close mine, too.

This is definitely kissing. I'm not quite sure where we're going with this, but I'm kind of liking it. Maybe this is Scarlet's one plan that won't end badly. Kissing is pretty simple and straightforward, right?

She breaks away from me after a couple of minutes. I blink open my eyes and look at her. She's smiling, manic, like a woman who has just been struck by creative inspiration. I've seen this look in her eyes before, and usually it's right before she runs off to lock herself away somewhere so she can draw something.

Aw yeah! That means I'm inspiring, right? I've inspired her. I'm so good at this.

"What else do couples do, though?" she asks. The way she asks it, I'm pretty sure she already knows the answer.

"Obviously they go on dates," I say. "They talk and text each other, and probably go to the movies or something."

"Caleb, we do all of that stuff already," she says. "We don't need to figure out how to do it for my art project. That part will be easy."

"Sure, I guess. I don't know what else, then."

"I know it's going to be awkward, but I think we should get naked," she says.

I'm not sure if I should rip my clothes off in two seconds flat or pretend to be a little less enthusiastic. Actually, you know what? I don't even think I'm enthusiastic. It's like... alright, so, I'd definitely like to have sex with Scarlet. This isn't a question of whether I'm interested or not.

It's about that whole Scarlet's Law thing. What happens when two friends have sex? Nothing good can come of this. Even if I think it'll be fine, and nothing bad will happen, I'm pretty sure something bad will happen.

The obvious answers are...

• a) It'll ruin our friendship forever.
  
• b) Scarlet will be disappointed, and she'll want to find another co-star for this insane movie idea of hers.
  
• c) I'm not sure what, but something else equally terrible will happen.
  

I actually have reason to believe most of b) won't happen. I can't tell you why right now. I'm not supposed to talk about it. Some of b) could happen, though. She could decide she wants another person to be in the movie with her instead of me. Maybe for artistic reasons. That'd make the most sense.

That's also the thing that would hurt the most. It's not even that I might not be good enough, but I can't even imagine Scarlet having sex with someone else, pretending to be his girlfriend, holding his hand, kissing him...

Well, fuck.
I don't like to swear much, but this is definitely a "fuck" kind of situation. I really need to make sure I do a good job with this.

Oh, uh... Scarlet's naked now, by the way. I'm mostly naked, too. She pulls my shirt up over my head, then works at unbuttoning my pants and unzipping them, then tugging them down my legs. I lift up my hips and help her out while lost in thought about how this idea of hers is going to go horribly wrong.

Alright, so we're not entirely naked. She's got her bra and panties on. I have my underwear on. We're still mostly naked and sitting in my bed, though. I'm pretty sure this is a recipe for disaster.

"I know it's, um... it's kind of weird, huh?" she says to me.

"Nah, of course not," I say, lying.

"Really?"

My cock has decided to take over, along with my false bravado. "It's something we have to work on, right?" I say. "If we're not comfortable like this, then--"

"I'm comfortable, though," she says, interrupting me. "Oh no, are you uncomfortable being naked around me, Caleb? I... I didn't really think about that."

"No, no!" I say, quick. This isn't going at all how I had planned. "I'm comfortable. I'm fine."

"Can I ask you something?" she asks.

"Sure?"

"Do you think I'm attractive? Like... do you think I'm pretty? I know this art project idea is kind of out there, and I... I'm wondering if maybe it's a bad idea."

My mind is saying that, yes, it's a bad idea. I also know I'd never tell Scarlet that.

"Why do you think it's a bad idea?" I ask her.

She shrugs. "I don't know. It's obvious, isn't it? I'm not really the most attractive girl. I know I'm not ugly or anything, but... I mean, look at you compared to me. I'm kind of weird, right? I've got these tattoos." She lifts up her arm to show all of the tattoos going from her wrist, to her shoulder, and down her side, then lower towards her hip. "My breasts aren't too big. I'm just not what you'd think of as stereotypically attractive, and I'm worried it's going to ruin the movie."

I open my mouth to say something, but she stops me quick.

"You're a really good fit for the movie, though," she adds. "You're kind of weird, too, but I like it. You're fun, Caleb. You look like you belong in a movie about relationships. Do you think this is a romance movie? I never really thought about it like that. I guess it can't be one if we break up at the end. You just... you're in shape. You've got some abs, and I like your arms and legs. You've got nice muscles. You're exactly who I want to play in my movie, but I don't know if
I'm
who I want in my movie with you."

"I don't want to do it with anyone else," I say without thinking. "I think you're wrong, too. I think you're the best choice. Do you know why? It doesn't matter if you're stereotypically beautiful, Scarlet. You're still beautiful. I think that will make your project even more powerful and provocative, also. It's a creative choice, and I think that, uh... by portraying beauty as being more than skin deep, you can make the entire production even more emotionally powerful. That's what you want, right? You want to evoke strong emotions and create something classic, yet controversial? I think this is the best way to do it."

"Are you sure?" she asks. "I can find someone else to do it with you if you want. I don't really want to, but... I will if you want. I bet there's lots of girls who would be interested."

"No," I say. "I'm sure. I want to do it with you. I think we'll be the perfect couple for your movie."

"Except we can't even have sex," she points out. "It's... it's awkward. We're being too awkward with each other."

"It's our first day of research. You've got the entire year to do this project, right?"

"I know, but..."

She looks at me and smiles shyly. I don't really think it's shy, so much as she's unsure and uncertain. To be completely honest, it's cute. I love when Scarlet just gives up trying to hide and shows me exactly how she feels. It's honest and raw and emotionally powerful.

I'm trying to be polite right now, but it's kind of emotionally powerful for my cock, too. By that, I mean my cock is straining against my underwear and, uh...

Do you really need to know all the details there? Seriously, do you?

"Let's keep going," she says. "I want to try something, alright?"

"Alright," I say. I have no idea what she wants to try, but I'd probably agree to anything right about now.

"Sex is kind of awkward, because I think we're skipping some things," she says. "Obviously it doesn't just happen with people who date. I know it sort of does, but it's always awkward at first, you know? It's hard to explore when you aren't very comfortable with someone, except we've both known each other for a long time so I think we can be comfortable with each other, right?"

"Right," I say. "I agree."

"I think the most confusing part about sex for the first time with someone you're dating is that you don't know what they like. It's a little awkward to just ask, too. Or to tell someone what you like. But let's try it."

"Uh... I think I agree with that, but I'm not sure."

"Let's masturbate for each other and talk it through so we know what we both like and we can see it in action."

"Uh..."

"For touching, of course, but also what we like to see. You said you think I'm attractive, right? What do you find attractive about me?"

Is this the most baited question in the entire world or what?

Scarlet obviously notices my reticence, because she rolls her eyes at me and sighs.

"Come on, just tell me. I'm not going to get mad. This isn't like if I ask you if my butt looks too big in a dress or something."

"Your butt doesn't look too big in anything," I say without thinking.

She looks at me, surprised at first, then she laughs. I laugh, too. This is more like our regular conversations. This is good.

"I like how you're smaller than me," I say. "It's... alright, don't take this the wrong way, but I like it because it's sort of like, uh... I can just pick you up, you know? I like how you could just jump into my arms and I could easily pick you up and grab your butt, then walk to a bed, and toss you down onto it, and... yeah."

"
Oooh
, I like that," she says. "We should add something like that to the movie. Maybe with rain, too? We both come in from the rain so we're wet and we're scrambling to take our clothes off to get dry, and we're about to go to the shower but then I playfully jump into your arms, and you pick me up, squeeze my butt, and drag me off to your bedroom."