Disable your Ad Blocker! Thanks :)
Chapter 9
by
Lossleader2
What's next?
Rest of the week
Max spent the rest of Thursday marinating in a mixture of both Denver’s and his own cum. It was a weird experience, he smelled like sex the rest of the day. Everyone in the office knew that Max had just debased himself for Denver and probably assumed he did worse. They talked to him normally but he could feel what little barrier between professional behavior and lewd desire falling away as they stared at the cum stains on his bunny outfit. He could feel them undressing him in their heads and imagined that they wished to use him in the same way.
Max still couldn’t comprehend what had happened and what he had done. Did he like men? He’d been here a week and was already eating cum like it was candy. His face flushed thinking about humping Denver’s knee. He couldn’t think about this anymore. Whatever that was he was determined not to let it happen again. He couldn’t get Denver’s words out of his head calling him a pig and telling him to oink while he humped his leg like a rabid animal. Dylan slamming a box down on his desk jerked him from his thoughts.
“Your upgrade madam.” Dylan said in a teasing tone. Max took the box and opened it to find a much larger butt plug, similarly jeweled at the hilt.
“Thank you.” Max said flatly.
“You okay?” Dylan seemed genuinely concerned.
“Yah, just tired.” Max lied.
“Why not just embrace it at this point?” Dylan lingered by his desk.
“Embrace what?” Max played dumb.
“You clearly like this. Look at yourself.” He gestured to Max’s cumstained outfit. “Youre a natural office slut, embrace it.”
“You’d like that wouldn’t you.” Max said with venom.
“Of course.” Dylan grinned.
“I’m not a slut.” Max said indignantly. “I’m doing this to keep my job, that’s it.”
“You keep telling yourself that, but I know one when I see it. You want to be on your knees doing that for Denver every morning by my estimate.”
“I didn’t do anything.”
“Thats not what it looks like.” Dylan sang.
“You like the idea of another man sucking your dick?”
“If that man looks like you and doesn’t complain too much.” Dylan said almost menacingly.
“Good luck with that.” Max was frustrated.
“I’ll win you over eventually. I know your type. You like to play hard to get. Not so hard to get for Denver though.”
“What I do for Denver is none of your business.”
“Ah, but it is.” Dylan leaned over Max’s desk. “I have all these pictures of you, don’t forget that.” Dylan walked away. Max sat there dumbfounded. How could he be so stupid. Dylan had pictures of him covered in cum, pictures of him filling his asshole with a buttplug. Was he threatening him? Max felt like he was going to cry.
The rest of the day Max felt paralyzed. He was in too deep into this weird pervy job and was feeling pretty fed up. He decided to go talk to Harry about Dylan and his ****. He knocked on Harry’s door and was called in.
“Harry, I need to talk to you about something.”
“Yes, Denver let me know about your little incident this morning. Your equipment is in the bag. I’ve emailed you a link with a video instruction on how to use it. There’s also this.” Harry opened his drawer and pulled out a stack of paper which he handed to Max. Max began to read it and then looked up at Harry.
“Is this a lease?” Max asked confused.
“Denver saw it fit to reward all your hard work. If you want it, it’s yours. You have until next Monday to sign the papers so go check it out this weekend if you can.”
“This is an apartment? I can’t afford this.” Max looked at the monthly rent, it was an eyewatering sum to him, even with his new salary it was way more than he could reasonably afford.
“The firm is offering it to you pro bono. You would make the payment on the company card in your name so that you can build credit and so that you have control of the lease, but you wouldn’t actually have to pay anything for it.” Max was shocked. The pictures attached to the back showed a well lit one bedroom apartment with a washer and dryer, a relatively large living room and a master bedroom with a walk in closet.
“It’s pre furnished, I hope you don’t mind. You’ll need to get a mattress of course but the bed frame fits a queen. It’s also much closer to work, which should make the commute less of a chore.” Harry smiled. “You’re doing a great job Max, this job is tough but it has it’s benefits. You’re clearly making Denver happy. Keep it up.” Max nodded.
“Thank you.”
“Make sure you have the cage on by tomorrow and call me if it gives you any trouble.”
“Right, okay.” Max walked out of Harry’s office carrying the bag and the lease.
When he arrived home he told his parents the news. They were thrilled and they called the leasing company to view the apartment on saturday.
“You are so lucky, I’ve never heard of a job paying for an apartment before, they must really like you!” Max’s mom was overjoyed. “Don’t make them upset.” His dad added in a joking tone. Max felt warm at how happy his parent’s were for him. They seemed so excited.
“I haven’t made a decision yet but it seems like a good deal.”
“Its an amazing deal, you’ll be able to save so much money. Why wouldn’t you take it.”
Max hesitated. He couldn’t tell them about the harassment or the fact that he got this by basically sucking his bosses dick.
“You’re right, I’d be stupid not to take it.”
Friday was a trial of a morning. The new butt plug was thicker and slightly longer than the last one and Max’s guts cramped as he tried to take the whole thing. It wasn’t huge by what he could find online but it was almost more than he could bear. It tore at the tender walls of his anus and his sphincter felt like it would snap as it came to the thickest point. After about 20 minutes of slowly impaling himself onto this cursed hunk of metal he was finally able to push past his broken ring and lodge the object somewhere that felt like it was next to his lungs. He waddled around his room, each step a new position for the invasive object as it molested his prostate and gouged at his colon. He quickly realized he should have done the cage first since despite the immense pain of penetrating his virgin hole he was now feeling the benefits of being airtight. His cock was constantly slightly aroused and the video tutoral for his cock cage was confusing enough as it was. He slipped the first piece over his cock and the second piece wrapped around his scrotum. The pieces were meant to join and be locked with a small padlock when done but his arousal made this seem impossible. He waited and tried to think of something mundane. Eventually he was able to get the thing closed and by the end his dick was stuffed into a small pink plastic cage. It was extremely uncomfortable, the little piece of plastic felt like it was **** his member into unconsciousness. With all of this done he barely had time to throw on an outfit before running out the door. He chose black dress pants with a black crop top with gold chains hanging from a metal choker. He noticed that this top didn’t fit as well as it did when he first tried it on. His chest was too big. Max removed the top and went to the mirror. He was growing breasts!
They were plump brown little mounds of fat where his flat chest had been just weeks ago. They were small mounds but it was obvious that he was growing a small pair of tits. Max’s mind raced and he realized that Harry had said something about the supplements he was taking changing where he stored fat. He turned around and realized his hips and his ass were bigger too. His ass in particular looked like it was going to bust out of his pants, a perfect little bubble butt. Max’s alarms were going off now and he didn’t have time to worry about this. He put the top back on and made his way to work.
It was a busy day with bills due to the clients so Max spent the day actually working. He skipped his morning meeting with Denver at his request so that he could focus on getting the bills out. It was another day of the typical flirting and sexual passes by his coworkers.
“Your ass is looking very edible today.” One of the analysts said as he strode by to the printer. Max flashed back to Harry devouring him from behind and got a little flushed.
“Max, can you come sit on my lap, I need some comfort.” Another analyst said as he was organizing a file. Max considered it but decided to let it pass.
“If you had a nose ring on you’d be my ideal woman.” Said an associate as he walked by Max’s desk. Max smiled at him but said nothing. People were always very flirt on Friday. The day passed quickly and Max was finished with his task. He was reorganizing his desk when a message from Dylan popped up.
“My office please little piggy.” The message read. Max bristled at the name. Denver must have shared his story with Dylan. Max walked over to Dylan’s office to find it open and another associate talking to Dylan. Dylan motioned for Max to shut the door. He did so hesitantly.
“Okay, well if you could help me close the account out, I would appreciate it.” The associate said, Max vaguely recalled his name to be James.
“Sounds good.” Dylan said and turned to Max. “Max thank you for coming. You know James right? He works from home a lot, the lucky bastard.” They both chuckled.
“Not so lucky because it seems I’m missing out.” James looked at Max like a piece of meat to be eaten.
“There are perks to coming in to the office. Max why don’t you show him one of the perks.” Dylan said slyly. Max’s gut went cold. There was no way he was doing this with them.
“Do you need some coffee?” Max said with a little bit of sass.
“Ooh i like it, very fun.” James said with a laugh.
“Why don’t you give him the Denver special?” Dylan egged it on.
“I can go get that for you.” Max pretended this was still about coffee.
“Don’t make her uncomfortable Dyl,” James said scoldingly, “I just want a little smooch, is that okay?” James tapped his cheek as if Max was supposed to kiss it. Max didn’t move from his spot. Dylan got up from his chair, the office was feeling very small now.
“Come on Maxy, just a little peck on the cheek.” Dylan said, laughing while he did it. Max wanted to run from the office but he stayed strong. He stepped toward James and bent forward, acting flirty, and gave him a peck on the cheek. Before he could back away completely, Dylan was behind him. Max stood between the two of them, not 5 feet spanning between all three.
“I like this outfit Max, your ass looks great.” Dylan pinched Max’s ass and he yelped.
“Don’t do that.” Max said, the fear obvious in his voice. James leaned in and grabbed Max’s face in one rough squeeze. He pulled Max in and their lips met. James held Max there as he kissed his lips. Dylan grabbed Max by the waist and held him tight but not painfully tight. James continued his **** and Max began to reciprocate out of fear of what Dylan might do.
“That’s hot Maxy,” Dylan teased as Max and James continued to make out, “give him some tongue now.” Dylan pressed his hips against Max’s ass as James slid his tongue down his throat. Max could feel Dylan getting hard and James’ breaths were getting fast. They were getting into this. Both men pressed closer, squeezing Mx against their bodies. Dylan started to grind his hips against Max’s ass as James put a hand up to his throat, lightly encircling it in his grasp but not squeezing. Despite his fear Max was feeling warm and that now familiar haze was starting to form in his brain. He kissed back, craning his neck and pushing and pulling with James’ aggressive advance. His hand found its way to James’ hip and he arched his back as Dylan continued to rub his crotch against his backside.
“Does she do more?” James asked after pulling away from Max’s lips.
“You’ll have to ask her.” Dylan said playfully.
“What else can you do?” James asked Max, his hand pulling Max’s towards his cock. Max pulled away and stepped out of Dylan’s grip. Max was a little bit glad he had the cage on because he didn’t want Dylan to know how much the two of them forcing themselves on him had turned him on.
“I won’t do that.” Max said breathlessly.
“Aww, thats a pity.” James faked a pout, “I need something to pick me up today before I go back to my wife and kids.”
“Does your wife know you try to fuck the male secretary?” Max asked pointedly.
“She met Tanya a few times but I don’t fuck male secretaries.” James said eyeing Max. “But if I call you Maxine it’s all the same at the end of the day.” Max’s head was spinning. He needed to find a way out of this room.
“How about you boys sit down and I’ll give you a little show?” Max offered. Dylan and James looked at eachother and both shrugged and took a seat. Max stood there a little bit dumbfounded. He hadn’t thought this through.
“Well, let’s see it.” Dylan said. Max started moving his hips in what felt like a sensual way. As soon as he started he felt ridiculous and almost regretted not letting them double team him in Dylan’s office.
“Strip!” James laughed and pretended to yell across a bar.
Max pulled his shirt up over his head and the men cheered quietly. He started to rub his chest which elicited a fuzzy sensation as the half formed breasts felt sensitive.
“Nice tits!” Dylan pretended to yell. Max blushed and resumed feeling stupid. He swayed back and forth and rubbed his chest for a bit longer, the quiet of the room felt like it was closing in on him. Dylan began to look impatient and Max realized they wouldn’t be satisfied by his small breasts. Max unbottomed his pants and slipped them off. His caged cock hung and clacked as he did so despite the panties holding it in place. He spun around to show off his ass and bent over so they could glimpse the plug that filled his gut. He shook his ass a little bit and he felt a hand on it. He stood and shook his head.
“Touch yourself!” Dylan laughed. Max began rubbing the cage and his exposed sack like he’d seen women do in porn. Unfortunately this turned him on and he continued to rub and fondle himself for their entertainment and his. Max finally removed his panties, now clad in only a choker, his cock cage and a butt plug. He turned about so that the men could see his accessories, he bent over again and then he stood up straight and bowed.
“Thank you for coming to my show.” Max said. They both clapped sarcastically.
“Very nice Max!” Dylan said as he stood up. He crossed the space between them with one long stride and took Max’s chin in his thumb and forfinger. Max looked up into Dylan’s eyes. “Next time we’re all together, I expect better entertainment than this.” Dylan said quietly and he kissed Max, holding him by the chin. Max hate Dylan but the kiss felt good and his insides melted a little.
“I’m getting a little jealous you two.” James said jokingly.
“Don’t worry James, next time you come in I’ll make sure Max gives you the Denver special.” Dylan patted James on the back as he took his seat. James watched Max’s naked body. He was skinny but the fat was accentuating his feminine features. He looked like a skinny asian woman if not for his caged cock.
“God, you guys sure know how to pick em.” James said, absently rubbing his crotch.
“You have no idea. Max you can get dressed now.” Dylan said dismissively. Max sheepishly gathered his clothes and slipped them on. The men resumed talking like Max wasn’t there, he felt used and discarded but every day without a dick in the ass was going to have to be a success. Max finished dressing and walked out of the office.
What's next?
Office Intern
First day
Max is a young college dropout with no prospects, but an offer from his uncle to work for a large firm might be his chance to make his parents proud. Little does he know that “Office Assistant” means more than he expects.
Updated on Jun 4, 2026
by Lossleader2
Created on Nov 11, 2025
by Lossleader2
- All Comments
- Chapter Comments
