Chapter Text
To say Gary’s romantic life was non-existent was the understatement of the year.
Becoming a henchman at the age of 15 and his only social interactions being hanging out with 24 around the cocoon, it made sense why. There were little to no opportunities to meet someone outside of the Guild world since being a henchman was a 24/7 job. Gary hadn’t even told his mom that he was a henchman - how was he supposed to break that news to a potential girlfriend. The only romance Gary experienced nowadays was a one-sided pining crush on his boss’ now-wife, Sheila.
Somehow during one of his and 24’s hangouts, 24 had mentioned a particular cam model website that he perused every so often when the two had gotten into a discussion about what material they use to “relieve themselves.” Out of sheer curiosity, Gary looked into the site the following evening, clicking through cam model after model. About to call it quits and fall back on his classic spank bank material, his eyes widen at the sight of you, quickly clicking on your photo to tune into your live.
He can already feel the material of his pajama pants tighten despite it looking like he arrived at the very end of your stream, your skin glistening with a light sheen of sweat as you were wrapped up in a fuzzy robe. Gary’s hand drifts lower, palming his thick bulge through his pants, your voice a bit raspy after what he assumed was an intense cam session, adding to the allure. Unlike the other models who seemed like they had a rehearsed script of moans and dirty talk, you spoke casually to your chat, answering questions casually.
“No, guys, no matter how much you tip, I’m not going another round. Are you trying to kill me?” You chuckle, watching as the comments stream in. Your eyes scan over the sea of comments, playfully responding to a few of your regular viewers who often tipped generously. Gary watched in want, almost longing for your attention as your soft laughter sent shivers down his spine, continuing to stroke himself through his pajama pants. You let out a yawn, the fatigue slowly hitting you. “Alright, I’m about to knock out, guys. Any last words before I end the live?”
Gary’s not sure if it was pure horniness or a longing to get a sliver of your attention that drove his hands to reach up, pausing their ministrations as his fingers type out a response.
‘Dude, I came in just 3 minutes ago but you’re actually stunning.’ - guest account
Your eyebrows raise at the guest comment since most guest accounts just pop in quietly, and then dip. Your lips curl into a tired grin, realizing whoever this commenter is came in late, but still stuck around just to hear you ramble for the last 3 minutes.
“Why thank you, mysterious guest commenter! Sorry to hear you missed the fun. I promise you I look better without the robe but you’ll just have to tune in next time to see, won’t you?” You reply with a wink. Gary stares at his screen in awe, shocked that you noticed his comment amidst the sea of responses spamming you for a response. “Oh fuck…” He whines, stroking his cock with renewed vigor through the fabric as his mind drifts to the thought of your soft skin underneath the robe.
“Good night everyone! Thanks for tuning in!” You say, blowing one final kiss to the camera which Gary groans at, cumming prematurely right as the screen cuts to black. Staring back at his reflection, he curses, glancing down at his now ruined pajama pants, “Oh dude, I just washed these!”
After quickly changing his pants and boxers, Gary finds himself snooping through your profile. He figures out through your bio that you typically are live two times a week - once on Wednesday nights and once on Saturdays. Despite just cumming, he feels his erection begin to grow again as he clicks through your gallery, seeing photos of you in different states of undress from lingerie to topless but no full nudity.
In a matter of seconds, Gary finds himself creating a profile with the username Viceroy and follows your profile, eager for your next live.
–
Over the span of the last few months, Gary had become a regular on your stream, joining right on time and usually being one of the first people to leave a comment with a small tip. He had set a reminder on his phone so he knew when you were going live, dropping whatever task he was doing as long as he wasn’t on an arch with the Monarch to go watch.
His new found obsession with you was no secret as it became a common topic of conversation with his best friend.
“Dude, you should totally ask for a private show. I mean you’ve tipped on every single live and you’re a moderator for her chat! She’s totally into you.” 24 said excitedly as they both exited the lunchroom after enjoying Wednesday’s buffalo wings.
“Oh god no! I’m totally fine watching them through a screen, thank you very much. Besides, if she took one look at me, she’d run for the hills.” Gary sighed, reaching down to cup his stomach.
“Aw, come on, dude, don’t get all self-deprecating on me. Total mood killer.” 24 nudges his friend’s side, hoping to lighten the mood, “You never know, some girls love chubby guys, they say they’re better to cuddle with.”
“She did say during a live that she prefers guys with a little more weight to them.. Maybe I might have a shot.” Gary perks up, the pair making their way down the long purple hallway back to their rooms. He feels his cell phone vibrating in the pocket of his henchman uniform, fishing it out. A notification flashes on his screen, indicating that you’re about to go live.
“Oh dude, she’s live. I gotta go!”
Just as they round the corner, they run into the Monarch who stops them in their tracks, “21, 24, I need you both bright and early tomorrow to do some reconnaissance at Venture’s gay little summer camp he’s hosting.”
“Didn’t your wife say you weren’t allowed to arch Venture anymore?” 24 questioned with Gary chiming in while checking his phone, antsy to get back to his room, “Yeah, she’ll probably notice 24 and I are missing and she’ll know right away where we are.”
“Hmm, you’re right. Maybe I get those lousy moppets of hers to do it for me. Though even speaking to those two gives me the creeps.” Malcolm shudders with his henchman nodding in agreement.
“Honestly, I don’t know why you ask us to do these things all the time, I mean you have 100 other henchmen right?” 24 comments to which Malcolm shakes his head, “No way, most of the henchmen that are ranked above you haven’t even been here for a year. You and 21 are my most loyal men, considering you two stuck around and didn’t ditch me for Monstroso. You know how this whole operation works.”
Seeing the time continue to tick away, Gary interrupts their conversation, “Sorry boss, I really gotta go! See ya later! ” He scurries off, leaving the two behind.
“Where the hell is he running off to?” The Monarch says in confusion.
“Oh, he got super into this camstar website I told him about and he watches this one model on there religiously.” 24 replies casually.
“Dude! Why did you tell him that?” Gary’s voice echoes down the hallway, picking up what 24 said right before he ran out of ear shot.
“What the hell was I supposed to say? Your mom was calling? That’s even more embarrassing, might as well tell him the truth.” 24 yelled to which Malcolm pinched the bridge of his nose with a sigh.
“I can’t believe you two are my most capable men.”
-
You had just started your live stream, making sure your ring lights surrounding your bed were properly set up before sitting back on the edge of the bed.
You look over the comments, greeting each person as they came into the room and left a tip. Though in reality, you were anxiously waiting for a particular someone - Viceroy.
He started popping into your lives in the last few months, leaving small but consistent tips and attending every single live with a few exceptions here and there. What made him stand out from the rest of the crowd was his sweet yet dorky nature. Most people, even your top tippers, would keep the conversation purely sexual or casual. At some point in the live show, Viceroy always left a sweet message, either wishing you a good night, or asking you if you’ve watched any of the shows he recommended.
The dynamic that you had with him did not go unnoticed by your other viewers who either got green-eyed with envy and tried to catch your attention with more generous tips or encouraged the banter between you two.
After a few instances of some viewers getting a bit too jealous and becoming aggressive in their comments, you had decided it would be best to get a chat moderator and you found yourself naturally gravitating towards his profile, sending him a private message and asking if he would mind managing the chat moving forward.
Outside of that, you two only interacted during lives which had your curiosity peaking each time you went live.
What was he like behind the screen?
What were his interests and hobbies?
What did he do for a living?
What did he look like?
You admittedly did some stalking on his profile which resulted in no answer to your many questions, his profile blank outside of his age and a profile picture of a yellow butterfly.
‘Guess he’s running late, I’ll get started then.’ You think to yourself as it has been a good 3 minutes of waiting and your audience was getting antsy, wondering when you were going to start.
“Alright guys, which toy should I use today?” You ask with a smile, reaching behind you to grab two objects - a vibrant yellow dildo in your right hand and a pink vibrator in your left.
“I know the vibrator’s a classic on my streams but I figured I’d throw in another option.” You say as you watch the comments flood in, requesting their choice while also throwing in other suggestions for other toys.
‘Let’s go with the classic!’
‘How about that rose toy you used a few weeks ago?’
‘Yellow dildo!’
“Looks like the yellow dildo has won!” You try to say enthusiastically though there’s a hint of disappointment as Viceroy has yet to log in. You let out a deep breath, trying to push down the feeling to get through the rest of the stream.
“Let’s get started, shall we?” You say with a smile, slowly dragging up the material of your oversized shirt to reveal your bare chest to the camera.
-
“Oh, please don’t end early today!” Gary groans, pulling down the hood of his henchman costume as he scrambles to grab his old laptop. His fingers immediately fly to click on the bookmarked page he had for your profile and his jaw almost hits the floor at the sight that greets him, scrambling to grab his wired headphones as your sighs and moans begin to play from the speaker.
Your legs are spread, back against the headboard with a few pillows propped up against your lower back and head for extra comfort. Sweat begins to bead at your forehead, your head thrown back in pleasure as the tip of your dildo presses deeper. In between your trembling thighs, your juices cause the yellow toy to glisten each time it glides out of you. You’re completely exposed to the camera, the audience seeing how the toy stretches you out.
Your toes curl as your free hand that was cupping your breast slides down to rub your sensitive clit. Your eyes flutter open to scan over your chat, your lips breaking out into a lazy grin at the sight of the familiar username popping up on screen.
‘So sorry I’m late! New toy?’ - Viceroy
You immediately perked up at the sight of his comment. You let out a shaky chuckle, continuing to pleasure yourself, replying to Gary’s comment immediately. “Yeah, it’s new. Hope you like it though you could have voted on it if you came in earlier.” You tease before shifting your attention to the other comments in the chat.
To say that Gary liked it was an understatement as he whipped off the utility belt of his henchman costume, pushing the pants down. His cock was already erect at the sight. Something about seeing the yellow dildo - a color that he donned daily - gliding in and out of you turning him on even more. His fingers wrap around the base of the shaft, beginning to slowly stroke as he tries to keep in tempo with you.
‘I was here on time!’
‘Dude, you always get her attention.’
‘Potential collab in the future between Viceroy and you? That’d be pretty hot.’
Your lips curl in amusement at the comments, “Now, now, behave everyone. You’ve all got my attention.” You assure your viewers though you can’t deny in your head that the thought of having Viceroy in the same room as you - despite not knowing anything about his appearance - caused you to clench tighter around the toy that is stretching you out. “Mm, collab with Viceroy, huh?” You say breathlessly, your voice hitching as you feel your first orgasm of the night slowly building. “Well, what do you think, Viceroy? Would you be up for it?”
Meanwhile, on his side of the screen, Gary's eyes roam over your body, wishing he could replace the toy between your thighs with his fingers, tongue, cock - anything to just get a taste of you. “Fuck, fuck, fuck…” Gary groans, his hand picking up the pace. He feels his length throb as you call out his username, eyes widening at your proposal that he has only ever imagined in his wildest fantasies. His free hand fumbles across the keyboard, typing out an eager yet short response, sending a small tip attached to it.
‘With you? Absolutely.’ - Viceroy
After seeing Viceroy’s comment, you bite down on your lower lip. Typically, your cam sessions were strictly business for you - strip, seduce your audience, pleasure yourself, banter and then log off. However, you can’t ignore the skip of your heartbeat at this stranger’s comment and your mind begins to drift, imagining the dildo that is filling you up is Viceroy’s cock. Your toes curl as you suddenly pick up the pace and you shakily reply, “Well, maybe we can make that happen.”
“Oh god yes, please, please..” Gary pleads, having a vice grip around the base of his shaft as he attempts to hold off his fast approaching orgasm. He tried his best to pace himself during your cam sessions, having one too many instances where he got too eager and ended up cumming only a few minutes into your stream. His free hand clumsily reaches over to his nightstand, fumbling to grab a few tissues as he tries to time his orgasm with yours, the fantasy of filling you to the brim with his seed usually running through his head.
Your sighs, whimpers and moans were a symphony to his ears as his hand began to move again, sensing that your own orgasm was approaching. Gary hated to admit it but over the course of these last few months, he had memorized every little movement, twitch, shift in pitch of your voice that indicated when you were getting close. To put it bluntly, he was obsessed.
“Oh fuck…’ Your breath hitched, the tip of your dildo brushing against a particular spot that made your eyes roll back in ecstasy. Your body felt like mush, melting into the sheets, as you continued to imagine Viceroy’s body on top of yours, the thought of large hands digging into your skin as he thrusts mercilessly into you. “I’m close..” You whimper out, your vision getting blurry that you can barely make out the flurry of comments and tips that flood the chat.
However, you’re able to make out one simple command out of all of them.
‘Please cum for me.’ - Viceroy
The knot in your stomach suddenly releases as the white hot sensation of your orgasm hits you, practically causing you to gasp and cry out in ecstasy. Your free hand grips the sheets tightly, riding out the intensity of it. Your chest heaves up and down, catching your breath. You slowly pull the dildo out of you, revealing the sticky mess you had created. Sitting up, you give the audience a playful grin, deciding to rile them up - particularly Viceroy - one last time. Your lips part, your tongue laying flat against the plastic as you taste your own juices. Your tongue glides up and down slowly, eyes gazing seductively at the camera while you lap up the remnants of your cum.
Watching you give your dildo a blowjob was driving Gary crazy, trying to envision his fingers focusing in on his swollen tip were your lips suctioned tightly around him. He can’t hold back any longer, gasping out your name as his sticky, white load splashes onto the keyboard, the tissues he had tried to prepare long forgotten by his thick thigh. “Oh gross, now the keys are all sticky...” He whines, grabbing the tissues and trying to wipe off the cum. Realizing the tissues weren’t going to cut it, he reluctantly steps away to retrieve some wipes that he kept in his bedside drawer.
Preoccupied with cleaning his mess as he meticulously runs the wipe over each key, hoping he wasn’t accidentally typing out some random strings of characters into chat, Gary’s gaze looks up to see you, having slid your shirt back on, signing off for the evening. “Huh, she usually sticks around for a bit longer to chat… must be tired.” He comments to himself, tossing the wipes into the waste bin. With ‘Stream Ended’ flashing on his screen, Gary is about to close out of the tab but he pauses at the sight of a notification in his inbox.
“What could that be?” He wonders, clicking on the notification in curiosity. Gary’s eyes widen as he sees your username, quickly opening the message. He nearly faints on the spot. He thought you were joking, simply bantering with him through the screen like you do with everyone else. Never in his wildest dreams could he have predicted the message that was on the screen:
‘So I wasn’t joking about that collaboration… but I figured, since you’ve been so loyal to me these past few months, how about a private session first? I’d love to put a face to your username, Viceroy.’