Archive of Our Own

Chapter Text

Jackrobbit: You’re beautiful

Dennis whines, high in his throat, twitching his hips as he grinds on the toy stuffed inside his cunt. “Th-thank you, Sirs,” he answers, breathless, like he always does when they talk in his chat.

User Jackrobbit has been watching Dennis for months now, one of his first and certainly most generous viewers. Over the months, he’s learned a few things, most importantly that there is more than one person behind the account. J and M have been together for a long, long time and have been married for a decade, but they keep it to themselves, deciding not to share that part of them with many others. J used the account alone a lot in the beginning, but now, when they announce their arrival, it’s both of them more often than not.

Other chats come in, too, other regulars begging for him to make himself come, or show off his holes, the usual stuff. Dennis pays less attention to those, like he always does, when his favorite viewers are in the chat.

“Feels s-so good,” he murmurs as he plants his hands on the bed, lifting his hips and dropping them back down, the soft vibrations of the toy rattling against his sticky, slick-coated walls. With every drop down, he rolls his hips forward, grinding his swollen dick against the sheets.

Jackrobbit: Are you going to come for us?

DaddyDerek83: yeah do it, cum for us

“Yeah, y-yeah, I’m gonna,” Dennis pants, sticking to grinding on the toy, feeling the stretch deep inside him along with the scratch of the sheets against his sensitive tdick. Sweat shines on nearly every inch of his skin, he feels sticky and hot and like his limbs are made of lead. He’s so close. He can’t. He needs. “Can I touch my dick? Pleasepleaseplease I-I need it,” he begs, watery eyes looking directly into the webcam, pleading with his viewers, with J and M. If only they could really see it. Dennis keeps his anonymity by keeping his face out of the camera’s view, a mask on just in case he slips up. The last thing he wants is for Dean, or deanboy99, to be revealed as Dennis Whitaker.

DaddyDerek83: yeah baby cum

RocknRules: ya lets see you cum all over that toy

Jackrobbit: No. Stop.

Dennis stops. His hips still, his grinding ceases. All he does is let out a low, pitiful whine.

Jackrobbit: Good boy.

His arms shake as he holds himself up, his breath coming in slow, quivering pants. “Please,” he begs once more, desperate for release. He’d had such a long day at the hospital, all he wanted was to come home and do a quick show where he gets his release and makes a little money. He can’t find it in him to disobey, though, his body coming to a halt before his brain had even recognized it.

Jackrobbit has tipped $50.

Jackrobbit: Can you lie on your back with your legs up? M wants to see all of you when you come.

Jackrobbit has tipped $50.

Jackrobbit: He also says I’m cheap. Sorry, sweetheart.

Dennis laughs, honestly laughs, even as exhausted and pent up as he is. And he agrees easily, “Yeah, okay.”

After tilting the camera down and lying back, he checks the stream to see the angle and feels himself blush from cheek to neck. It’s obscene, both holes on display, his cunt puffy and swollen from the last half-hour, hole slightly gaping, proof of the toy he’d been riding moments ago. There’s slick everywhere, his thighs and cunt gleaming with it.

He reads through the slew of messages that had come in while he was repositioning, but he focuses on just one.

Jackrobbit: That’s it. Touch your dick, jerk yourself off til you come. You’ve earned it.

And he does. He shoves a hand between his legs, gets a finger on either side of his dick, pinching it between his knuckles, and he goes to town. “Thank you, thank you, thank you,” he babbles as he rockets towards his orgasm. It’s noisy, not just his talking, but the wet sound his cunt makes, his hole clenching on nothing, slick leaking down his crack, soaking into the sheets. Fuck, he’s going to have to wash those.

It doesn’t take long for the orgasm to crash into him, overwhelming him in the moment between one minute and another. His back arches sharply, abandoning the strokes to rub at his growth, messy and uncoordinated, chasing ecstasy.

“I’m coming, I’m coming, oh my fucking god, I’m coming,” Dennis wails, thankful that Trinity is out with Garcia for the night. His free hand teases at his left nipple, the only one that retained feeling after his top surgery. His empty cunt pulses with each wave of pleasure that overtakes him, weak spurts of slick coming from his hole with every movement.

All at once, he collapses back, legs squeezed shut and turned to the side. With his knees tucked up, his puffy lips could be seen between his thighs, everything else tucked behind plush flesh. After a moment of catching his breath, he sits up, sitting cross-legged with a pillow on his lap as he reads back through the chat.

He’d missed a few tips.

“Thank you, RocknRules, MistressVi, and Cowboyfan69.” He blushes. “I guess I was a little distracted.”

There were quite a few messages, but no more from his favorites. They tended to do this, go quiet after he gets to the final act of the show. Dennis likes to imagine that they’re watching him with their hands around each other’s cocks, maybe J on his knees for M. J talks about sucking Dennis’ cock a lot when he pays for private messages. He thinks J probably likes to do that for his husband, too. He doesn’t know what they look like, only that they’re older than him by “quite a bit”, but honestly, that’s enough to do it for Dennis. He’s gotten worked up over the thought of them more than once.

“Well, thanks for spending time with me tonight,” Dennis says, his usual sign that he’s wrapping up his stream. “I hope you had a good time.”

JackRobbit has tipped $150

And that, too, is typical. Sometimes it comes with a message, other times not, but there’s nearly always a final tip.

“Oh, I meant to say this earlier, but uh, I guess I was a little eager to get started.” More like he’d been eager to follow someone’s suggestions. “But I’ve added a few things to my page. Uh, a wishlist, and you can request custom videos now. I-if you want. Obviously, I’m happy when you guys just watch, you know that.”

He’s never been very good at selling himself.

He really thought he’d have a request for a video from Jackrobbit. The disappointment he feels when he wakes up the next morning makes him feel a little nauseous, but he packs that away. He does not have time to be getting hung up on customers. That website was simply meant to make him some extra money so he can start paying rent to Trinity and still send money home.

The next week is normal. He goes to work, furiously masturbates as soon as he gets home remember how often his attending, Dr. Robby, touched him that day. He uploads a video, a short one where he fucks himself while he has a jeweled plug in his ass.

That is what gets JackRobbit’s attention.

JackRobbit has requested a private chat! $150 pending.

That’s more than his going rate for chats, but he’s long since stopped trying to explain that to the couple, who always insist on paying more.

He doesn’t accept it right away, instead he shuts his bedroom door, turning the lock so Trin doesn’t accidentally waltz right in after her shift and see something she shouldn’t. It’s not like Dennis always jerks off when he talks to clients. Actually, he usually doesn’t, but this client is different. Something about the couple really worked him up. So, he gets himself comfortable on the bed, vibrator near by, just in case.

Deanboy99:
Hi :)

Jackrobbit:
Hi sweetheart. Saw your video. Top notch, as always.

Deanboy99:
Thank you! You’re sweet. You can always comment on the videos, you know.

Deanboy99:
Instead of paying to message me.

JackRobbit:
Right, but we like paying you, Dean. And we have, well, I have, a bit of a request.

 

Dennis sits up a little, curiousity piqued.

Deanboy99:
Oh? And who is “I” today?

JackRobbit:
It’s J, sweetheart. This might be a little crazy, and please, feel free to tell me no. Just because I’m paying doesn’t mean you have to do anything you’re uncomfortable with.

Deanboy99:
Yeah, dad, I know that :p

JackRobbit:
Fuck.

Deanboy99:
Oh, someone likes daddy :p

JackRobbit:
Ugh, don’t distract me, kid.

Deanboy99: Sorry daddy :P

Deanboy99:
Ok sorry, i’m done for real now. What was this crazy request?

JackRobbit:
Well, the other night M and I were fucking, talking about you

Deanboy99:
Details pleaseee!

Dennis is already slipping a hand into his briefs, toying with himself. He's pretty easy to set off these days. It's been a little while since he's actually hooked up with anyone. He just doesn't have the time, not with his work shifts and doing the cam stuff. The money is more important right now, even if he'd give anything for someone else to be inside him right now.

JackRobbit:
I had him bent over, fucking him hard. He was losing it, babbling away when I brought you up. Told him to think about how good it would be to be fucking into you while getting fucked by me.

Deanboy99:
Holy fuck yeah?

JackRobbit:
He came so quick, fuck. But I was perusing your wishlist and saw some things..

Deanboy99:
Which things? Something catch your eye?

JackRobbit:
The fucking machine

Deanboy99:
Oh.

JackRobbit:
Was wondering if I bought that and a toy that looks about M’s size, I could buy a custom video where you use it? Maybe…play along with the fantasy?

Dennis whimpers, slipping his fingers over his dick, his hips twitching. He catches the fat nub between his knuckles, jerking himself off to the thought. He lets himself get lost in it for a moment before scrambling to pick his phone back up, tapping away a response.

Deanboy99:
Yeah! For sure!

Deanboy99:
I mean, sure, I can do that. :)

JackRobbit:
Do you like the idea of me fucking him in to you? Of knowing how big his cock is? Everytime he chats with you it’ll be all you think about.

JackRobbit:
The guy’s not small.

JackRobbit:
All that dick, but it’s pretty useless with just the two of us. He just wants his needy fucking hole filled.

Deanboy99:
Holy shit that’s so hot

JackRobbit:
You wet for me? For him?

Fuck, yeah he was. He was spreading it over his dick, his middle finger dipping down to his leaking hole, gathering slick and dragging it up over his swollen dick.

Deanboy99:
Yes sir so wet omg

Jackrobbit:
Fuck

JackRobbit has tipped $50

Deanboy99:
You’re supposed to be sending me toys

JackRobbit:
Can’t a guy do both?

Deanboy99:
Could I ever see you guys?

JackRobbit:
Could we see your face?

Deanboy99:
Maybe

He shouldn’t. He really fucking shouldn’t. That was the one thing that kept him from panicking about all of this. Even if someone did find out, they’d have no way of proving it was Dennis.

Deanboy99:
If I showed you my face would you consider showing me yours?

JackRobbit:
This is dangerous, kid. You should keep your anonymity.

Deanboy99:
Is that a no?

JackRobbit:
We’d have to think about it. If you do, I’ll talk with him.

Deanboy99:
That’s fair

JackRobbit:
Gotta head into work, sweetheart. Think of me while you get off.

Deanboy99:
Who said I was getting off?

JackRobbit:
Are you touching yourself?

Deanboy99:
….yes.

Deanboy99:
That is besides the point

JackRobbit:
Just like I thought

JackRobbit:
Have fun Dean. Make yourself feel good.

 

And he did. He jerked his dick until he was crying out, imagining being stuffed full of M, J fucking him deeper into him with every thrust. Luckily, Trinity was still out, so he’d been able to get his sheets in the wash and clean ones put on his bed without being obvious.

“You’re going to be gone how long?” Dennis asks while Trinity throws clothes into a bag.

“Like a week, Huckleberry. You’ll still see me at the hospital,” she says, walking into the bathroom, and coming back out with an arm full of toiletries. “I picked up some extra shifts, and Garcia lives closer, so she offered that I could crash at her place.”

Dennis nods. “Call me if you need me?”

“I’ll be fiiiine, but yeah, if I need you, I’ll call,” she agrees, knowing better than to put up a fight.

Flopping down onto the couch, he looks up at her. “When are you leaving?”

Trinity pulls her phone out, checking the time. “Uh, like two hours. She’s gonna pick me up.”

“You wanna watch something?”

“Sure!”

He lets Trinity pick, but in all honesty, he’d kind of zoned out after about ten minutes, the realization that he would have the house to himself for a whole week truly settling in. He could prerecord a bunch of videos, maybe do a special livestream where he doesn’t have to worry about going too long.

If the stuff J ordered gets here on time, he’d be able to do his custom video, too. He’s excited to do that one; the idea is incredibly enticing. It’s so enticing that he’s actually considering showing a little bit of his face in the video. Even if he knows he shouldn't.

He really, really shouldn't.