It starts, as many things do these days, with a text message.
Any other Friday night Dean would probably have slept right through it. He’s been woken up at ungodly hours frequently enough by Benny trying valiantly to convince him that it’s the perfect time to join him for a drink that it’s pretty much habit to silence his phone before going to bed now. Sometimes it really is just a drink that Benny is looking for, but sometimes it’s a little bit more, and Dean is weak so he’ll inevitably cave and end up hauling himself out of bed for an ill-advised booty call. And as much as he loves sex, what Dean really wants these days is sleep, hence the silenced phone.
On this particular night however, Dean had dinner with Sam and Jess, ignoring his better judgement to stay late and drink probably several more beers than was technically advisable, and was so tired by the time he made it home that he barely had the foresight to remove his jeans. So when the text comes in at 2:27, it pulls him right out of a dream about having a beer with Harrison Ford. He reaches blindly for the phone, squinting at the screen as he opens it to see the offending message.
That’s all it says. Dean checks the sender and finds it’s not a number stored in his contacts. From the area code he can tell that it’s local but he doesn’t recognize it. He’s still scratching his head in that haze that results from being pulled abruptly out of a very deep sleep when the phone chimes again.
I am now.
Dean sends back. It’s hard to convey annoyance in a text message so he just has to hope the person on the other end picks up on it.
In retrospect, Dean has no idea why he replied at all. The easiest thing to do would be to silence his phone and go back to sleep and pretend it never happened. He might wake up to more messages in the morning but who cares, right? But he’s alert now, and he’s morbidly curious, so when his phone says he’s got a new picture message, he doesn’t hesitate to open it..
Dean has no regrets.
The picture message, sent with no caption or commentary, is a clear and vivid shot of the most perfect cock he’s ever laid eyes on, and Dean has seen his fair share of cocks in his day. It’s hard and fully erect, the tip shiny with precome, held loosely in one hand. He assumes the owner’s other hand is holding the camera. Tattoos snake up the forearm that he can see, the fingernails of that hand painted shiny black, and Dean groans quietly. The fact that a picture like this can stir such lust in him so quickly is a frustrating reminder of how long it’s been since he got well and truly dicked.
It’s the dry spell that makes him stare at the picture for so much longer than is reasonable. Common decency says that if a stranger accidentally sends you nudes, you delete them and inform the sender that there’s been a mistake. It’s the nice thing to do. But fuck, it’s just such a perfect dick. Dean would love to wrap his lips around the head and lick up every drop of precome, feel the thickness of it filling him up. He’s hard just looking at it. He stares for a ridiculously long time, thinking about how heavy it would feel on his tongue. For so long, in fact, that apparently the sender gets impatient.
Like what you see?
Dean hesitates. It’s past the point where he can let this mistake stand, but again, he’s weak. He goes to take one more good look at the picture before doing the right thing and deleting it. The fingers wrapping around that gorgeous cock are long and slender, strong fingers attached to a wrist bearing a tattoo that Dean might have recognized immediately if it weren’t for what else was in the picture. Now that he’s looking, though, it’s achingly familiar. He’d know those tattoos anywhere. They snake up the forearm, actual snakes with their heads on the back of his hand, entwining up his arm in some sort of biblical thing. There’s an apple in there somewhere, the forbidden fruit, and the bicep is covered in curling vines and leaves. The fact that the subject’s face isn’t visible in the photo doesn’t hinder Dean at in identifying him now that he’s picked up on this very important detail.
Very nice. I was feeling pretty guilty there for a minute seeing as this is a wrong number and I’m not the person you meant to be sending that to. Until I realized that you basically just sent me a still off a porn site. If you’re gonna send unsolicited dick pics, you should at least make sure it’s your own dick.
Dean scoffs and drops his phone on the bed. Those tattoos should have been a dead giveaway. The man who wears them, the one with that perfect cock, also has shiny black plugs in his ears and a ring through his lip, though he doesn’t always wear it. His dark hair is perpetually messy, whether he’s just been fucked or is just about to fuck.
He’s a fucking gorgeous man. He’s also gorgeous when he’s fucking.
Dean knows this for a fact because he’s spent many a lonely night watching the owner of the dick in the picture do incredibly filthy things while Dean wraps his fist around his own dick. That dick doesn’t belong to some rando sending a booty call to the wrong person in the middle of the night, it belongs to Emmanuel Milton, who is quite possibly Dean’s favourite porn star in all the world.
What do you mean? Of course it’s my own dick. Why would I send someone else’s dick?
I don’t know. But I’m pretty sure Emmanuel Milton isn’t actually sending me nudes right now.
Oh so you recognized me
I recognized the tattoos. Not convinced they’re attached to the person sending the texts.
Well, stranger, I’ll make you a deal. You tell me whose number I got, I’ll send you a pic that proves I’m me
How you gonna manage that?
Dealer’s choice. Whatever you say, that’s what I’ll send. Pick something you know can’t be a fake
Dude. I don’t even know why you care if I believe you. It’s just a wrong number.
Same reason I tried to booty call my friend at 230. I’m awake and I’m bored. It’ll amuse me. Enough stalling. Name. Photo parameters
Dean is entirely unconvinced. There’s just no way. Emmanuel Milton is prolific. He’s fucked all the big names (or been fucked by them). He’s hot as hell, cocky and aggressive regardless of whether he’s the bottom or the top. He even managed to be bossy the one time Dean watched him as the middle of a really fantastic threesome. There is just no way in hell that the guy texting him is the same one that winks while he’s deepthroating. It’s not possible.
But he’ll play along. He’s awake now anyway.
Ok, I’ll bite. Send me a picture with a cowboy hat, a Popsicle, and your whole face has to be visible.
Is that all? You’re not even making this difficult. And you still haven’t even told me your name.
Dean, and since you’re being a cocky little asshole about it, I want a blue necktie around your dick.
Since Dean has committed himself to being awake, he flips the lamp on his nightstand on and sits up in bed. This is either going to be the most comical farce of his adult life or something well worth waking up for.
Dean’s bet is on farce. He’s expecting a grainy picture of someone who looks nothing at all like Emmanuel Milton with a dollar store hat and an unimpressive dick. And then he’ll laugh and turn off his ringer and go back to sleep, and in the morning he’ll probably laugh some more.
Dean doesn’t get a response for several long minutes. It goes past the point where he thinks the guy is taking multiple selfies and picking the best and into the realm where he starts to think he’s successfully called the bluff. He’s not going to get a response, he thinks. The guy has given up fucking with him. Then his phone chimes again, flashing an alert that says he’s got a new picture message.
He doesn’t get a grainy picture. What he gets is clear and sharp. It’s not taken with a cell phone; much more likely it’s been taken with a higher quality digital camera, uploaded to a computer, emailed to his phone, and then texted to Dean. And it’s the furthest thing from disappointing. There in all the glory afforded in a screen the size of his palm is none other than the actual Emmanuel Milton with a cowboy had perched on his head, lips wrapped around a cherry Popsicle. His eyebrow is raised in a challenge, blue eyes sparkling. The tattoos on his chest are fully visible now, bold black lines swooping and curving across his body, licking over the hip bones that jut out sharply. There’s a dark blue tie around his cock, still erect in Emmanuel’s other hand.
Dean is no longer upset about being woken up in the middle of the night.
So, Dean, believe me now?
I stand corrected. That is definitely your own dick.
I told you. Now, fair is fair. You’ve got two naked pictures of me but I’ve got none of you.
I thought the trade was picture for my name.
Well yeah. But we’re quite unbalanced. You’ve seen my cock and, I assume, at least several of my films if you recognize the tattoos. I don’t even know what you look like. Come on. Make this interesting.
Dean snaps a handful of quick selfies with the camera on his phone and spends several minutes deciding which one is the least unflattering. He ponders putting a shirt on and then decides he’s too lazy to bother, so he’s naked from the waist up in every shot. All the while he’s wondering how the fuck this is happening. What in the world did Dean do to deserve this incredible gift of fortune? A man he’s never dared to think of meeting even in his lustiest dreams just happens to have a friend whose phone number is close enough to Dean’s own that he can accidentally send Dean nudes, and then he decides to roll with it? Dean has clearly won the unsolicited dick pic lottery.
Dean thinks he looks appealingly dishevelled in the picture he sends. His hair is sleep mussed and his skin is flushed and pink, both from the warmth of his bed and the filthy thoughts presently running through his head. There’s absolutely no pretence of disinterest in this conversation. Dean would love to be able to say that he’s playing it cool, but he’s not. He’s totally focused on his phone while waiting for a reply, although he does spare enough attention to grab a beer out of the fridge. He’s got a feeling he’s gonna be awake for a while. Might as well have a drink.
He’s just barely sat back down on his bed when Emmanuel replies.
Shit you’re hot.
Dean laughs to himself when he reads the message. He’s heard that before, or at least similar, but never from someone as desirable as the person he’s currently talking to.
Yeah? Glad I don’t disappoint.
I wouldn’t say that. I AM kinda disappointed you didn’t see fit to show a bit more. I’d love to see your cock.
And now Dean’s internal monologue has just been replaced with disembodied screaming. He shouldn’t be considering this, like, at all, but he is, and furthermore, he’s out of bed and flipping to the camera app on his phone like, instantly. It’s amazing what kind of stupid decisions Dean is capable of making when his dick is doing the thinking, but then, if it’s his dick that’s going to be in the picture, he supposes it should at least get a say in the decision.
The mirror is probably the best way to do this thing. He spares a quick glance for the room behind him to make sure there’s nothing he’s gonna be embarrassed about, then slides his boxer shorts to the floor. He’s already pretty hard from the thrill of the whole scenario, so all it takes is a few firm strokes to bring him to full attention. He takes the picture with his hand still wrapped around it, the swollen head poking out the top of his fist, and sends it to Emmanuel before he can talk himself out of it. It’s grainer than Emmanuel’s pics, less steady, but his cock is clear enough in the image.
That’s what I like to see.
Emmanuel sends, and Dean blushes.
You hard for me?
He asks, and Dean nearly chokes on his tongue.
Good. I don’t think I’m getting my booty call tonight, so it’s up to you to keep me entertained
If you’re up for it ;)
I think I can play along
Dean replies, his mouth going dry. He’s suddenly very glad he doesn’t have a roommate and runs no risk of having anyone walk into the room at any point, because yup, he’s definitely sexting with a porn star when he should be sleeping, and he’s 100% going to see where this goes.
Are you touching yourself Dean?
Tell me what you’re thinking about
Dean is so fucking turned on by all this. It’s hard to type replies with one hand, but he strokes himself slowly and relies on auto-correct to make his messages make sense. Deciding what to say is a different matter. Dirty talk in person is one thing. You can whisper filthy things in a person’s ear, growl out desires and murmur praise, and it just comes naturally. Sexting is different, and it’s not something Dean has ever had occasion to do.
I’m thinking about sucking your cock
Is what Dean settles on, because honestly, he is. He’s thinking about how well he might manage something that big, thinking about how sensitive Emmanuel’s balls might be, thinking about how amazing it would be to hear all the little noises he makes in his films but in person, just for Dean.
He can already tell this isn’t going to be a marathon endeavour. Even the distraction of having to focus on texting isn’t going to slow the simmer enough to really prolong anything.
I bet you’d look so good on your knees for me. Do you like to bottom, or top?
Bottom. Definitely bottom
Dean replies quickly. The little fantasy he’s living out right now has him on the edge, so close to coming already. The man on the other end of this text conversation could do things that would make him scream with pleasure. Dean can’t begin to imagine this going anywhere further, but what’s happening right now is already enough to blow his mind.
So you’d want me to fuck you then? Everyone always wants to fuck me. Unlocks some kind of achievement, getting their dick in someone with my resume.
I don’t mind topping but I’d much rather get fucked. Not gonna lie though I’d do pretty much whatever you wanted me to do.
Dean’s fist flies over his cock while he waits for a reply. He rocks his hips up into the friction, revelling in the sparks of pleasure that course through his body when his wrist twists just so at the tip. A part of his brain still can’t believe this is even happening, but the rest of him is stuck on the part where it’s just way too fucking hot for words, and he really doesn’t feel like analysing it any further.
That’s an incredibly appealing offer. I might have to take you up on it some time. I bet you look fucking gorgeous when you come.
He’s still trying to figure out what to even say in response when the next message comes through, another picture. Emmanuel has taken the picture lying back on his bed. The tie is long gone and he’s probably eaten the popsicle by now, but he’s still wearing the cowboy had pulled low over his eyes. His cock is still clutched in one hand, leaking come onto a stomach which is already covered with the evidence of his orgasm. The sight of it is enough to drive Dean over the edge, spurting over his fist as he groans into the night. He’s still breathing heavily, coming down from his orgasm when Emmanuel messages again.
Not what I was aiming for when I sent that text, but not altogether an unpleasant surprise. Don’t lose my number, Dean. Never know what kind of trouble we could get into together.
Sure thing, Emmanuel.
Dude, you know that’s not my real name right? Call me Cas. You’ll be hearing from me.
Sure thing, Cas.
Dean turns his phone to silent for real this time, drains the rest of his beer and, after cleaning himself up, crawls back into bed. Sleep comes easily, surprisingly, but his dreams are excessively dirty and that’s no surprise at all.
They’re so dirty, in fact, that when he wakes up in the morning on Saturday he’s got himself almost convinced that he dreamed the entire thing. It’s certainly in keeping with the wildly inappropriate nature of the other things his mind spun out overnight. He remembers the dream about having a beer with Harrison Ford, although that one ended rather abruptly, and he has distinct recollections of dreaming about getting on his knees and letting Emmanuel Milton come all over his face. Faced with those memories, it’s only reasonable to believe the whole nude pictures/sexting thing was a dream as well.
Based on this certainty, he doesn’t even bother looking at his phone until after coffee is brewed and he’s sitting at his kitchen table with a steaming mug. Even then he only unlocks the thing to check his email and see if there’s anything interesting on Facebook (spoiler alert: there’s not). It is therefore entirely unexpected when he sees he’s got a new text message from a number not saved to his phone.
Good night, Dean,
So yes, he did have a text conversation with a porn star last night, and yes, the pictures are all still on his phone. He nearly does a spit take of his coffee when he’s forced to acknowledge it actually happened, but it only takes a couple taps of the screen to save the pictures to his device for posterity.
He also stores Emmanuel’s—or rather, Cas’ number to his contact list, knowing full well he’s not going to have the fortitude to start anything but sending silent messages out to the universe in hopes that Cas will.