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Sam’s laptop dinged and he scurried to the bed, falling onto his belly and adjusting it in-front of himself.
In the corner, a little dialog box appeared: new message.
wayward67: Hey! You up?
Sam smiled, crossing his ankles behind himself as he clicked the box and typed a reply.
dimplesss: yep, sure am. Whats up?
Within seconds, the three little typing dots appeared before another message came in.
wayward67: whole lotta nuthin, bored!!
Sam huffed out a little giggle. Biting at his lower lip before typing another response.
dimplesss: that’s not very fun.
wayward67: entertain me then? ;)
Sam fondly rolled his eyes, typing another response.
dimplesss: how would you like me to do that?
wayward67: send pics ??
dimplesss: not a chance, big guy. nice try though.
wayward67: worth a shot lol
dimplesss: if you say so.
wayward67: video chat?
Sam shook his head, rolling onto his back on the bed. Within minutes, another ding.
wayward67: I didn’t mean to scare u away we can just talk insteadddd!
Sam laughed, typing a response.
dimplesss: no it’s cool, I’d rather just talk though.
wayward67: yea that’s cool with me
The two of them talked off and on throughout the day and night for the next few months. Any chance Sam got, breaks between classes, first thing in the morning, late at night into the early morning hours- wayward67.
Wayward67 was the last thought he had before bed, and his first thought in the morning. Sam began to look forward to hearing that ding, to seeing that username pop up.
One evening, Sam had been pestered enough by his friend group to go out for drinks.
By the time he finally stumbled back to his dorm, it was just after midnight. He was originally going to lay down when he heard the ding from his laptop.
When he logged in, he watched the spam of messages flood in.
wayward67: u done with class ?
wayward67: ??
wayward67: hellloooooo
wayward67: where’d u go ? :(
wayward67: I’m a lil worried about u.
wayward67: u there ?
Sam blinked a few times trying to stop his head from spinning as he attempted to type a reply.
dimplesss: iM here now ate toy okay?
wayward67: what
dimplesss: yes I home
wayward67: are you having a stroke?
dimplesss: no???!? jsyt a little too mucin to drunke
wayward67: you’re drunk? Hahahaha
dimplesss: yeapppp
wayward67: try & sleep it off. i’ll be here when you wake up. (:
The following morning, Sam woke up with an awful headache. His breath tasted bad, the light hurt his eyes and he felt like he was seconds from hurling when he forced himself to sit up.
that familiar ding made him crack his weary eyes open once more.
wayward67: how ya doing sleeping beauty?
Sam groaned, typing out a short reply before disappearing into the bathroom to shower and take some Tylenol.
dimplesss: awful
wayward67: poor baby guess you can’t handle your alch
After about twenty minutes, Sam emerged from the bathroom and went straight back for the laptop.
dimplesss: sorry, had to shower. still feel like crap, just cleaner now.
wayward67: without me ?
dimplesss: such a fuckboy thing to say haha, also no one calls it “alch” grandpa.
wayward67: ouch my heart
dimplesss: hahaha
wayward67: wyd ?
dimplesss: laying on my bed, got a killer headache & don’t even feel like getting dressed.
wayward67: hmmm, just a towel ?
dimplesss: yes horndog, just a towel.
wayward67: mhm, I’m gonna need a pic. Just for confirmation.
dimplesss: not a chance. I can give you a description?
wayward67: that could work ;)
dimplesss: well I’m tall, brown hair..
wayward67: a little more descriptive wouldn’t hurt
dimplesss: yeah yeah, green eyes..
wayward67: short or long hair ?
dimplesss: uh like below my ears but not quite shoulders, curls at the bottom.
wayward67: nice nice, judging by the user name I’m assuming dimples ?
dimplesss: how’d you know ? Haha yeah.
wayward67: I bet you’re hot.
dimplesss: I wouldn’t say all that. But I’ll let you think what you want to.
wayward67: I plan to (;
Within the week to follow, Sam’s communication got less and less frequent with wayward67. Sam was having some issues with schooling & his scholarships- the online chatroom becoming the least of his worries.
Dean was starting to grow restless. He had barely heard from his little online fling in days. Usually she wasn’t like this, she always answered, she was always there.
He was always waiting by his phone, every little notification making him practically dive for it. No dimplesss to be found.
After a particularly hard few weeks of hunting, a new scar across his chest from a fuck up, and a damn near fist fight with his father, Dean got the notification from the chat site.
your friend ‘dimplesss’ is live now, show them some love.
Dean slipped off to the motel bathroom and turned on the shower to hide the sound. He clicked on the live stream and his breath caught in his throat.
The username read dimplesss, but the screen depicted a male body. A set of broad shoulders, a worn purple t-shirt stretching across toned pecs, a v-neck showing off the slightest hint of collarbones and a bobbing adams apple with every swallow, long folded denim clad legs with a tear in the knee.
Dean was dumbfounded. This entire time he had been picturing a female. 5’7, 5’8 in stature, a wavy chestnut bob, big green eyes, plump lips, dimples, tits.. and that was apparently not the case.
He knocked the lid of the toilet closed and plopped down on it, watching the screen carefully.
dimplesss head was just out of camera view, but he was reading comments and responding to them- taking requests.
Within a matter of minutes, the boy was shirtless and up on his knees with his hand down the front of his jeans.
Dean wanted to be disgusted with himself, he’d been talking to this kid for months under the impression he was a she, now he was watching him play with himself on camera.
“If you guys wanna see more, give me suggestions. The more you tip, the more I’m likely to do it.” The boy spoke, chuckling when the coin notification sound played signifying another tip coming in.
He unbuckled and unzipped his jeans, and teasingly gave a little wiggle of his hips letting the jeans slide down to expose the waistband of his boxers.
The coin sound played again. “Ooh, Big tipper! Wants the bottoms off. I can do that.” The boy spoke out again, shuffling to get off the bed to wiggle the jeans down his long legs.
Just as he was beginning to slide his boxers down and expose the v of his hips, John’s heavy fist hit the back of the bathroom door.
Dean jumped hard enough to drop his phone on the floor, eyes wide with panic as he looked toward the door.
“Been in there long enough, I need to piss.” John called out.
“Yes sir! Be out in a second.” Dean answered, shoving his phone in his pocket and shutting off the shower water.
He emerged from the bathroom, avoiding his father’s gaze as he slipped past him.
Oddly enough, he was a little bummed out about missing the rest of the cam show, but he couldn’t risk it with John being around.
Dean waited until the following day after his hunt to reach out.
Sam just finished his dinner and was sitting down to wrap up an essay when his laptop dinged.
wayward67: could’ve told me you were a dude…
Sam furrowed his brow, leaning back against the pillows and settling the laptop in his lap.
dimplesss: what?
wayward67: ur a guy.
dimplesss: yeah? what ever made you think I was a girl? I never said I was.
wayward67: u never said u weren’t either. what guy picks the username dimplesss? That’s girly.
dimplesss: guys can have dimples too. I literally have dimples.
wayward67: why have you been ignoring me?
dimplesss: I haven’t been ?
wayward67: u have. We used to talk daily, now I’m lucky to get a response once a week.
dimplesss: what is with you?? I don’t owe you anything, man. You can’t come at me mad because you assumed I was a female & that I don’t spend every waking second talking to you.
wayward67: whatever
Sam rolled his eyes, exiting out of the tab and closing the laptop. He still had to make enough money to cover the next few payments on his tuition until the problem with his scholarship was resolved, so he knew he’d have to pull the tab back up later- he just planned to ignore wayward67 for a while.
Sam’s evening cam shows started to grow in popularity. He attracted more viewers with each one, and got a little dirtier each time. He did still manage to keep his head out of the shot though, that was his one rule.
Dean let his frustration with the situation simmer, even occasionally tuning in to the live streams. He always had to leave them before the finale though, thanks to John.
Weeks went by before Sam decided to finally even open wayward67’s chat log.
wayward67: u still mad at me ?
wayward67: I’m sorry :(
wayward67: I was an asshole
wayward67: I shouldn’t have assumed, & I know u got a life that doesn’t revolve around me
wayward67: although I’d like it if it did
wayward67: that was supposed to be funny ^
wayward67: but also truthful
wayward67: I still do like u alot, boy or not.
wayward67: pls don’t ignore me forever :(
wayward67: I miss hearing from u
wayward67: I really am sorry
wayward67: what made you start camming to begin with ?
wayward67: r u ever coming back ? :(
Sam read over the logs, frowning to himself. He’d missed talking to him too, he felt pretty bad for ignoring him.
dimplesss: I’m here, hi.
Just like clockwork, those three dots soon appeared.
wayward67: hey !
wayward67: how’ve u been ?
dimplesss: doing alright I guess. You?
wayward67: better now that you’re speaking to me again. (:
dimplesss: that’s sweet.
wayward67: how’s school?
dimplesss: wrapping up finals for the semester. Been stressful.
dimplesss: also, about why I started camming.. had to make some extra cash.
wayward67: ? U get into trouble or something?
dimplesss: no, well sort of ? financial aid office screwed up & I had to make a few tuition payments.
wayward67: oh shit that’s not good.. everything straight now ?
dimplesss: yeah, scholarship is back in full effect so I should be alright.
wayward67: does that mean no more cam shows?
dimplesss: I don’t know it was kinda fun..
wayward67: maybe you could just put them on for me ? I can pay.
Dean knew good and well he’d have to hustle pool or darts every night to afford to pay this guy what he was making by putting on the shows, but to keep his attention and not have to share- he’d do his damndest to make it happen.
dimplesss: idk about that, I was making decent money to just play with myself on camera.
wayward67: uggghhh
dimplesss: besides, I don’t even know if I forgive you
wayward67: Cmon don’t be like that u punished me enough, it’s been like a month since u talked to me :(((((
dimplesss: okay, okay. I do forgive you, you miss me ?
wayward67: I did! thought about u a lot
dimplesss: is that so ? did you catch any of my shows ?
wayward67: a couple, never got to watch all the way through bc of my dad though.
dimplesss: maybe I can fix that for you ?
wayward67: don’t tease me
dimplesss: teasing is the fun part ;)
wayward67: I’m already hard just thinking about u tbh teasing is just torture now
dimplesss: pretty excited for someone who was mad I wasn’t a chick
wayward67: shhh we don’t talk about that
dimplesss: wanna show me how excited I make you ?
wayward67: fuck yes
wayward67: wait does this mean I get to see your face ??
dimplesss: long as you promise to keep it a secret ;)
wayward67: I’m drooling over here
dimplesss: down boy, let me get situated & then you can call.
wayward67: yesssss
Sam giggled, stripping out of his shirt and unbuttoning his jeans before placing the laptop in his lap. He adjusted the screen so he was only visible from his neck down to his hips.
He opened the webcam to check his own appearance in the dim bedroom lighting, purposefully adjusting his jeans so the band of his boxers showed off the v of his hips.
He then closed the camera and opened back up the chat tab.
dimplesss: okay ready (:
Within seconds the call tone sounded through the speakers. Sam took an excited little breath before pressing accept.
He was met with another dimly lit room and the view of a male from chest down. Some shuffling of the camera and then static could be heard.
Then the chat tab popped up.
wayward67: sorry my mic on the laptop is acting stupid.
dimplesss: that’s okay, we can type here and still be on the camera.
The camera was adjusted while the other male typed on the keys each time he responded.
wayward67: so about that finale ?
dimplesss: show me what you’re working with big guy.
the other male shifted the camera down further to reveal his lap and his hand came into view, fumbling with his jeans and boxers. He revealed himself to Sam, wrapping his calloused hand around his stiff cock once it was freed from the confinement of his bottoms.
Sam bit his lower lip, watching the slow drag of his hand. The free hand came up to the keyboard, showing just barely in the camera.
wayward67: show me ?
Sam gave a little nod, although his head wasn’t in frame and he palmed himself through his boxers before pulling himself free from them. He then leaned out of frame to retrieve the lube bottle from his nightstand, squeezing a generous amount in his palm once back in frame.
dimplesss: got lube ?
wayward67: not currently
dimplesss: spit in your hand
Sam smeared the lube over his member, shuddering a little as his palm brushed the flushed head.
He carefully watched the screen as the laptop was settled a little further from the other boy’s body revealing his chin & lips.
Sam’s eyes were glued to the screen as the other boy raised his hand and spat into in, trailing a string of saliva from his flushed pink lips to his hand.
Dean smeared the saliva over his aching cock, his lips parting with a satisfied little moan at the cool sensation settling over his flushed erection.
dimplesss: I wish I could hear you, I bet you sound hot as fuck.
wayward67: sorry, I’ll try and get my mic to work next time.
dimplesss: next time? testing your luck there, big guy. ;)
Sam could see the other boy’s lips spread into an amused grin.
The two of them chatted back and forth, making a show of jerking off for one another for a solid fifteen minutes.
By the time either of them got close, it was getting harder to type and keep the rhythm at the same time.
wayward67: I’m gonna cum
dimplesss: do it, cum for me
Dean’s free hand came into view and forced his shirt up to his chest, fingers flexing into the material as he shot ropes of thick white cum onto his own belly.
Sam watched the other male stroke until his body shuddered, his own lip trapped between his teeth to silence himself as he too finally came onto his own abdomen.
The both sat their looking at each other, covered in their own cum and panting for a minute or two, until Sam finally rolled out of view to grab his discarded shirt to wipe himself off.
wayward67: let’s see that face now ?? I’ll show you mine if you show me yours ?
Sam crawled back onto the bed, settling the laptop back in his lap
dimplesss: okay okay, fine. but remember you can’t show anyone. I’m anonymous for a reason.
wayward67: promise!
Sam nodded a little, nervously biting at his lower lip. He had a gut feeling this was a bad idea, but couldn’t quite place why.
dimplesss: we will both close our eyes and open them on three deal?
wayward67: deal.
Sam unmuted his mic and closed his eyes. He waited a few seconds for the other boy to do the same.
“1..”
Man that voice sounded really familiar. Different from the cam shows, maybe it was just because it wasn’t being broadcasted, it was just a video call- yeah let’s go with that.
“2…”
Dean was nervous himself, but also excited. He finally got to put a face on the person he’d been chatting with, and more recently.. jerking off to, and with.
“3.. open them.” Sam announced, opening his own eyes as he adjusted the camera to show his face.
He was met with an all too familiar face. Big green eyes, freckled cheeks (with a subtle flush of after orgasm bliss) plush pink lips, and shock- yep, this was officially the most horrific day of his life.
“Dean ??” Sam gawked, nearly choking on his words.
“Sammy??” Dean gasped. “What the fuck-“
Sam didn’t even give Dean time to finish talking. He slammed the laptop screen down, ultimately ending the call from disconnection, before shoving the entire thing off the bed. His entire face felt as if it would combust from the heat of embarrassment.
Not only had he been chatting it up with his brother for months, he done all sorts of disgusting things in front of him on those cam shows. He wasn’t even sure what all Dean had seen, however, he did know that they’d just jerked off together & that thought alone made Sam feel sick to his stomach.
He was certain Dean would either rat him out and John would kill him, or Dean would murder him himself.
However, neither of those things happened. In all actuality, there was a knock at his door exactly three days later and he opened it to find Dean who immediately locked lips with him before he could even stammer out a poor excuse.
Sam definitely wouldn’t be putting on anymore cam shows for strangers now. Dean had a new guilty pleasure.