Don’t You Dare

Most of the weekend passes without any sighting of Pen. The only time I managed to catch a glimpse of him before Sunday night was when I happened to get home from practice early Saturday afternoon before he retreated back to his room.

Now, if this were later in the semester, I wouldn’t be concerned. During Hell Week—what we call the week of finals—I can go days without seeing him. He’s either locked in his room studying or over in his studio at the Arts building across campus, finishing up whatever design project he’s been working on the entire semester.

But I know that’s not it.

He’s only giving me what he thinks I want. Space and time. Which I do…but I don’t at the same time, and it’s almost as confusing as this whole situation to begin with.

Maybe because by giving myself space, I have no way of knowing what he’s thinking or feeling. Sure, I’ve made exactly no effort to find out, since I’m still reeling from the entire situation, but the not knowing is still suffocating, nonetheless.

Fuck, I can’t really say I blame him for holing up, either. Not after the way I slammed the door in his face.

And let’s not forget, I was the one keeping a massive secret, only to drop it like an atomic bomb at what might be the worst possible moment. We’ve been best friends for two decades. Literally our entire lives…and that was how I decided to bring up my maybe attraction toward men.

Which is still only a maybe, because even with taking the step to download Toppr, I’m still clueless.

Chatting with the guys on the app was supposed to be a way for me to sort of play it safe. I kept my profile image anonymous, only using an abs shot, and you don’t have to make anything public but your user name. Keep my identity under wraps—especially since there are a lot of guys at this school on Toppr—until I figured out if I’m even into it. Then maybe even explore it if the stars aligned and the opportunity presented itself. See if any interest is sparked.

Only one guy really has as of late, which is a number far smaller than I would have figured.

He goes by the username balls4lyfe, and I’ll admit, I got a kick out of that play on words after I commented on it, only to find out he actually plays a sport with balls.

I think that’s part of the reason it’s been so easy to talk to him, since he’s in a situation sort of like mine. Another college athlete who wants to get his shit figured out privately without the gossip mill running amuck. It’s been hard, though, wondering if he’s my teammate. Or if maybe he’s a guy on the football or basketball team. Shit, maybe even soccer. I’m not really ruling anyone out at this point.

Or…maybe he’s lying and he’s not an athlete at all. It’s that last little theory which keeps me from revealing I’m also an athlete.

From his body, though? I’d say he’s probably being honest.

And I’ll admit, I have the urge to see more than what he’s shown me. I think I’d even be cool with getting nice and sweaty with him, because I definitely like what I see…but it’s still just off. Something I can’t quite put my finger on, but our interactions all feel weird to me. The flirting is too forced, maybe? And he’s kind of…clingy. He’s always wanting to talk. Blowing up my phone like crazy, especially when I was at the party. Of course, at one point when I gave into temptation and checked the DMs when I was pissing, I realized why.

He was there. Or, at least, I’m almost positive he was. His status said within .1 mile, so I’m sure it wasn’t a coincidence. But the slight panic I felt in my stomach that he might recognize me—even when I knew he couldn’t because my face and name aren’t public on Toppr—tells me I’m not ready for whatever we have to be anything more than virtual conversation.

I feel really shitty for keeping it all from Pen, though I had my reasons. Plenty of them, in fact, and all still feel valid and justifiable.

Would he look at me differently? Will he be mad that I didn’t tell him sooner? Is it going to change the friendship we’ve had for years if I really do like guys too?

Basically, I’ve been afraid to rock the boat because I didn’t want to fuck something great up in the process. Yet the boat’s still been rocked. And the fears and worries and doubts are more prevalent than ever, no matter how hard I try to shove them and him to the back of my mind.

Which is why, as I lie across my bed and stare up at the ceiling on Sunday night, I take the first step. I might be a coward to do it through a text, but it’s still a white flag. I just hope he sees it that way.

Me: Hey.

I hear the ping of the notification through the wall as I stare at the screen, waiting for it to show as read. When it does and he starts typing back, my heart crawls in my throat.

Pen: You ready to talk about it?

And just like that, I’m hit with another massive wave of guilt. I shouldn’t feel guilty, though. Not for trying to understand who I really am and certainly for not being ready to talk about it. That’s the biggest thing I’ve tried to tell myself for over a damn year now, and what countless blogs and Reddit feeds I’ve skimmed through have said too.

Being your most authentic self is the only way to ensure your happiness.

I never really thought of it that way, but it makes sense. I can’t see anyone being truly happy if they’re hiding who they are. Especially such a massive part, like their sexuality.

Even Pen, who hides the deeper pieces of himself from the entire world. It has to chip away at him, having his guard up all the time. Never letting people in. The only time I ever see him at his happiest is when he’s around me or his mom, the people who know what lies beneath the armor.

But I guess he’s not the only one doing it these days…and I think it’s finally time I let him in too.

Me: Yeah…I’m sorry. Dropping that on you how I did was fucked. It wasn’t fair, and I don’t want you to be pissed at me for it.

Pen: I’m good. Well, now I am. But are you?

Me: I feel a little better now that you know.

Pen: Can I ask why you kept it from me?

Me: I didn’t want to say anything until I knew for sure, ya know?

Pen: Makes sense. And now you do?

Me: Not even close.

I hear his deep chuckle through the wall, and I picture that damn dimple popping out below his mouth as he smiles at his phone. It does something stupid to my stomach. That mixture of butterflies and straight up desire.

Pen: Have you tried any gay porn?

Yes, and while I found some of it really hot…

Me: It’s too unrealistic at this point.

Pen: And hooking up isn’t helping?

Me: I haven’t exactly used the app to hook up.

Pen: Might be a good thing. If you can’t even kiss me, how can you hook up with someone you don’t even know?

Yep, and this is why he’s the smart one. Level-headed and always thinking big picture instead of me, who lives more in the moment.

Me: Maybe I’m just not ready yet.

Pen: Maybe not. You will be eventually.

I know he’s right. I’ve known that for a while as I’ve tried to navigate this on my own. But having someone to validate it makes it a little easier, for whatever reason.

Me: Thanks.

Pen: Always got your back.

Me: So it’s not weird?

Pen: That kissing me made you realize you were MAYBE into dudes? Not at all. It’s kind of a compliment, if you think about it.

A warm feeling fills my stomach, and I have no idea why I was so freaked out about telling him about this sexual awakening. Granted, he doesn’t know about me still wanting to maul him on the regular or about my attraction to him specifically. But this is a start, and I already feel like the weight of the world’s been lifted off my shoulders.

Another text pops up, making me laugh.

Pen: You think I’m hot.

Me: I can hear your ego inflating from here.

Pen: It was good to hear you laugh, though. And don’t worry, I think you’re hot too.

Me: *insert Ryan Reynolds rolling his eyes gif*

Pen: He’s definitely hot. No man can deny that. I’d say you have good taste.

Me: Why do I think you’re gonna want to help me match people on Toppr now?

Pen: Uh, that’s what best friends are for.

I have to laugh, knowing his friendship is so much more than just helping me pick out hot dudes from an app, though the fact that he’d even be willing to says a lot about who he is. And again, I wonder why the hell I was so afraid of opening up to him about this.

He’s the person I can count on to get me through the hard shit. The brutal moments, like the deaths of our fathers. Or even just the smaller shit, like having no energy to go get food after a long day, so he does it for me.

When school or baseball or life feels fucking impossible, he’s the one who makes it better.

Pen: Have you thought about trying sexting with a guy on the app to start? Sending dick pics and trying to get off to them? Maybe that would help you start to picture it happening IRL.

Pen: Is this weird for me to be asking that? It feels weird.

Yeah, it might be weird if we weren’t us.

But what’s also weird is the idea rolling around in my head. Or maybe it’s not weird as much as it is insane. And it probably crosses more lines than any best friends should, which is why I should keep this crazy idea to myself. It’s better—safer—that way.

Yet my stupid fingers, guided by my even stupider brain, still types out the message before I can back out of it.

Me: Don’t you dare?

Pen: I have a feeling I’m about to regret my inability to say no to that question.

I smirk, despite my anxiety ramping up. It’s true that he’s never been one to pass up a dare, though I don’t point out that he technically did say no when he passed on that dare to drink that nasty alcohol mixture at the party.

Rolling my tongue over my bottom lip, I lean back against the wall and…I hit send.

Me: I dare you to send me a dick pic.

I watch as the three little dots at the bottom of my screen pop up, type for a few seconds, then disappear. A minute passes, then the dots come again…only to disappear once more.

Fuck.

This was a really bad idea. Colossal mistake. I’m probably making things more awkward between us…and if he refuses, I swear I’ll probably jump off the damn roof rather than look my best friend in the eye after asking him to show me his cock.

Especially when we both are more than aware why I’m asking.

I’m about to send him another text, telling him to forget it or that I was joking when one from him pops through.

Pen: …hard, I’m assuming?

I chuckle, the panic that was rising in my chest subsiding ever so slightly.

Me: Isn’t that the point of a dick pic?

His response is immediate.

Pen: Good point. And I want you to know I’m smart enough to see what you’re doing here.

My heart plummets, but the dots keep moving.

Pen: If you need a picture of my hard dick to figure out if you’re into guys, that’s fine. I’m happy to be your sexual guinea pig. But this is leverage. You could do anything you want with it, like send it to everyone on your contact list. Or post it on Reddit.

A snort escapes me because he’s not entirely wrong, though I don’t think I’d ever do something like that to him on purpose. I’d never intentionally try to hurt or embarrass him. To that degree at least. But at least he’s being a good sport about all this shit.

Another text pops up before I can respond.

Pen: My proposition: I show you mine if you show me yours.

My eyebrows shoot to my hairline as I type out a response.

Me: Blackmailing me? I never asked to be part of a dare.

I can practically see the grin on his face as I read his next text.

Pen: We can rectify that. Don’t you dare?

I laugh, knowing full well I’d go through with it just because he asked. It’s just how this works between us, the banter and egging each other on to the point of idiocy. Because…that’s what this is. What most of our dares have always been.

Me: Okay, fine. Any additional terms?

Pen: I dare you to send me a NEW dick pic.

My brows furrow.

Me: As in one no one has ever seen?

Pen: As in one you take right now.

My heart starts pounding in my chest as I reread his text about thirty times, doing my best to process the request.

He wants a dick pic no one has seen. He wants me to get hard…right now…and send him a picture.

And now I’m circling back to my point from earlier about this being insane. Literal fucking insanity.

So…naturally, I text him back with a revision to my own dare.

Me: Same to you, then. Even the stakes.

Pen: Done. Five minutes.

I shake my head, not really believing where this is going right now. In all the years we’ve been friends, seeing each other’s penises has never entered the equation. Well, scratch that. I’m sure I’ve seen it, considering our mothers bathed us together as kids, but it’s not like I remember what it looks like. And well…I’m sure it’s a lot bigger now.

Guess I’m about to find out just how big it is.

And I’m astounded to realize the anticipation of him sending me the image is more than enough to make my cock thicken beneath the mesh of my athletic shorts. Obscenely quickly, I might add.

Not one to waste time, I quickly slip my shorts down to my knees and wrap a fist around my length. Barely two strokes have made me rock solid since I was nearly there before I even touched it, and I don’t think it takes more than ten for me to be ready to explode.

But not before I line up a shot for Pen, snap it, and send it off before I think better of it.

My eyes sink closed then, reality and my biggest fantasy mixing for the first time as I picture Pen in the room beside me, lying across his bed just like I am, fucking his fist.

Does he cradle his balls? Knead them in his palm while he jacks his length? Does he like fast, short strokes, or long and torturously slow ones?

My brain imagines it all, every possible scenario, and it only gets me hotter.

A groan of frustration slips from me, and I release my cock to roll to my side. Searching my bedside table, I find a bottle of lube and coat my shaft with it. Taking a few more long, steady strokes, I feel like I could blow at any second.

Then my phone pings with a text, and I peel my eyes open to look at the screen to find a two-word reply to the pic I sent that nearly makes me choke on my own damn spit.

Pen: Stroke it.

I type back one-handed, the other doing exactly what he said.

Me: I already am.

Pen: Prove it.

Proof? But how, unless…

I shake my head and laugh, letting the idea marinate for a second. Thinking about how weird this is and how many lines we’re crossing by sending dick pics alone. But for me to send him a video of me jacking off has to cross so many more. Ones I probably don’t even know exist.

It’s not like I let it stop me, though.

Nah, I hop, skip, and take a grand fucking leap over every one of those lines as I take my cock in my hand again, adjusting the camera so my full length is visible. It glistens from the lube, and it aches for release already.

I’m so hard for him. Only for him, and this incessant want I have for him is making me crazy. Irrational. That can be the only reason I hit record as I let my fist slide up and down the length, rolling it over the head on the upstroke.

“This what you want, Pen?” I whisper, my voice graveled as I continue to work my cock for him and the camera. “You want to see my hand wrapped around my cock? See how hard I get just thinking about the pic you’re about to send me?”

I swallow harshly as I stop the video after about ten strokes and hit send, not bothering to care that the lust in my voice as I spoke was far too obvious, or that the words I spoke were ones I should never speak to him. My only hope is by some miracle, things between us aren’t weird the next time I see him. Though I doubt I’ll be able to look him in the eye for a few days after this.

Only a minute passes before he texts back again.

Pen: You sound like you need to get off. Might as well make use of it.

I smirk, already way ahead of him this time.

Me: What’s that saying about great minds?

Pen: Glad to see we’re both thinking with our heads.

A bolt of lust zaps through me when I read the text, seeing the double meaning behind his words. And I grip myself harder. Tighter. The ache in my balls only intensifies.

My eyes roll back in my head as I start fucking my fist more furiously, those two words—stroke it—replaying in my mind on a loop. I hear it in his voice, complete with a lilt of unmistakable desire. See his lips forming the words before they collide with mine in a brutal kiss that has my toes curling. His tongue tastes like mint and smoke in my mind, as he takes over for me, jacking my cock until I’m panting and writhing for him. Begging. Pleading into his mouth for him to let me come.

The fantasy is so intense, it has my back arching off the bed slightly as my hand keeps shuttling over my shaft.

I hear my phone ping as I start getting close and I debate just checking it after. I’m so fucking close, and entranced by the scene behind my eyelids, breaking away from it now is sure to only leave me with blue balls. But I’m hopeful the sight of his cock is what’s waiting for me behind the dark screen, so I grab for it anyway.

There’s no photo waiting.

It’s a voice message.

Damn it.

Annoyance hits me for a split second as I go to press play, adjusting the volume and setting it beside my head. And the second it starts playing, I forget all about the non-existent photo.

This is so much better than any picture.

“I can hear you through the wall, you know that?” Pen’s voice spills from the speaker, floating over my skin in his smooth cadence. “Every pant and sigh while you’re getting off to thoughts of me, I can hear. And that’s what you’re doing, right? Jacking yourself while picturing me?”

Oh, my God.

My cock throbs in my palm, pre-cum dripping and leaking all over my stomach and hand as I stroke faster to the sound of his voice.

“What filthy things are we doing together in that head of yours? Am I sucking you? Swirling my tongue around your cock? Teasing you before taking you deep? Or are you the one with a cock down your throat while I fuck your face until you can’t breathe?”

He’s trying to kill me. And he might just succeed.

I’ve never been one for dirty talk before, but holy shit, do I ever want more of it from him. I want every dirty, wicked word he has to say right now.

I pound on the wall adjoining our rooms, and if I wasn’t so close or half the chicken I am, I’d go in there. Fuck the consequences, I’d walk in there and slam my mouth to his and rut myself against him until I came all over him.

Fuck the picture too; I’d settle for getting my mouth on him instead. Let him do whatever the hell he wants to me as long as I learn the taste of his cum and the sounds he makes when he loses control.

Like he knew what I needed, he’s there moments later. Right on the other side of the wall. Speaking low and seductive through the drywall barrier, just loud enough for me to hear.

“Fuck your fist, Kee. Fast and hard. Let me hear how much you want me.” His voice is raspier than normal, and far less composed. “Get there for me, baby.”

He almost sounds as needy as I feel, and that sends me straight over the edge, falling off a cliff into the sweet, sweet oblivion.

With a low moan, the sound rumbling from deep within my chest, I’m overcome by my release. Cum shoots from my dick in thick ropes, coating my abs and hand with the sticky liquid. I feel like I’ve been hit by a freight train of pleasure as I try to slow my heart before it pounds its way out of my chest.

My entire body feels high on endorphins and adrenaline, floating on a hazy cloud of ecstasy as I listen for him on the other side of the wall. But it’s silent, save for the sound of my own heavy breathing as I try to come down from my orgasm.

Then I hear a soft thud from beside me, something hitting the wall on the other side, before his voice comes through again.

“That’s it,” he breathes. “Fucking perfect, Kee.”

My eyes sink closed, a small, sated smile resting on my lips.

I’m so blissed out on a high from my orgasm—one brought on by the strangest exchange of nudes I’ve ever experienced—I might pass out without cleaning up first.

In fact, that’s exactly what happens.

Which is why it’s not until the next morning, when I wake up covered in dry cum and lube, that I realize something.

He never actually sent a pic back.