Friday

Max struggle with selecting an outfit. He had never been much for style and always picked what felt comfortable to wear. This job was testing his rudimentary fashion knowledge more than he expected. The outfits were mostly curated for him but there were only a few of those. Harry had given him a suitcase full of various fetish adjacent clothing but not everything appeared to be a perfect match. He would need to figure this out eventually. He remembered what Harry said and decided that his best bet was to dress slutty and worry about style later. He fished out a pair of panties which he wasn’t quite used to wearing. They didn’t seem designed to accommodate his package, but with the right adjustments he looked pretty good.

Next he grabbed a pair of black stockings that went past his knees, a pair of low cut boots, and some short jean shorts. He threw on a crop top with lace in the front and a light jacket and with the bob cut he looked at least a little bit goth. He figured this would do for now and really only got the idea from scrolling egirls on his phone. He found he was taking more inspiration from them and less attraction lately.

With this done Max threw on a large trenchcoat to hide his clothing selection and put on a little makeup the way the videos online taught him. Some darkening around the eyes to make them pop from his brown skin. A little bit of concealer and some lip balm.

When he arrived to work he went straight to Denver’s office with a cup of coffee as was his routine. He knelt by Denver’s knees, waiting to be released to go back to his desk. Denver mostly ignored Max which was fine by him, he didn’t need to spend 5 minutes tracing his thick cock through his pants. After about 30 minutes Max’s knees started to ache, he shuffled to get comfortable.

“Oh I’m sorry Max, I was distracted. You can go.” Max got up and began to walk to the door. Before he could open it Denver added “Good luck today, remember what you’re here to do.” Max nodded and walked out. He assumed Denver was talking about the same thing as Dylan but he had no clue what to expect at this point. His stomach tied itself in knots.

The rest of the day passed quietly. A couple of associates actually asked him to do work related stuff and Max enjoyed the busy work. They always gave him lots of compliments and were often very flirtatious but they weren’t aggressive the way Denver and Dylan were. He liked the attention at least, and it was a little thrilling when they leaned in close and brushed against his ass or legs.

At around 2:30 Harry messaged Max that Denver would be leaving soon and to do his check in before he left. Max groaned and knocked on Denver’s office door.

“Come in. I have to go so I’ll make this quick. We’re very happy with your performance so far and we plan to bring you on full time. I’ve emailed you a list of comments from the week and Harry will talk to you about your contract. Standard NDA similar to what you signed your first day, but much better pay package and use of the company card for all office related purchases. Your healtchare package is also unique and will cover elective procedures should you choose to do them. Very pricey.”

“Thank you sir.” Max said with some enthusiasm. He still felt weird about this job but the offer was good and he had no other prospects.

“Have a good weekend, and don’t let Dylan keep you up so late, though the pictures are nice.” Max was unsurprised at this point that Dylan had shared his pictures. Max noted that he could never send Dylan anything worse than he already had.

“Thank you sir, I’m glad you enjoyed them.” Max put on his most submissive voice for this. Denver finished gathering his things and walked up to Max. He grabbed Max’s face with one hand and kissed him on the mouth without warning. His lips were warm and his short beard scratched against Max’s smooth skin. He smelled amazing and Max barely registered that he had begun to touch Denver’s chest with one hand. Denver pulled away and then reached down and groped Max’s package through his jean shorts. “Good girl.” He said as he gave Max a squeeze, sending a jolt of pain from his sack to his stomach, but then a wave of pleasure as his cock strained against the denim and Denvers hand.

“When i get back from my trip next week I’m gunna be tired and pent up, I’m gunna need you to fix that when I arrive Thursday morning.” Max nodded, not sure what he was agreeing to. Denver left Max stunned as he walked out his office door. He held the door and Max scurried through.

Max returned to his desk in a haze. Did he just agree to suck Denver’s dick? Denver also just kissed him and Max was hot about it. Why was he so hard and why wouldn’t it go away.

Not 10 minutes after Denver left, Mx received a message from Dylan on his computer.

“Come by my office.” Max had been dreading this all day but he made his way to Dylan’s office. He was starting to feel like he was getting passed around.

Dylan’s door was open and Max walked in. Dylan motioned for Max to close the door and then proceeded to stare at Max in his outfit.

“You look good in this, I like the shorts.”

“Thank you.” Max had to keep from rolling his eyes.

“I think it’s missing something though. I doubt Harry included one of these in his little suitcase but this is a part of the uniform you should always include.” Harry reached into a drawer and pulled out a black box. He handed it to Max and gestured for him to open it. Max wasn’t sure what to expect, possibly jewelry? Max lifted the lid and was met with a large silver tear drop with a jeweled handle.

“Is this..” Max had seen things like this before online.

“A plug!” Dylan practically cheered, “You wear it everyday and once you get used to it, I can give you a bigger one.” Dylan was very excited.

“I don’t think this one will fit.” Max said skeptically.

“Sure it will, if you want help putting in I’m happy to assist.”

“No, that’s okay.” Max blurted out quickly.

“If it’s your first time it helps to have someone who knows what they’re doing.” Dylan said coyly.

“It seems simple enough.”

“Describe the process to me?” Dylan sat his head on his hands in a mocking manner.

“I would just insert it in my… ass until it hits the lip and then leave it there.” Max was sure he made a mistake by Dylan’s smile.

“I think that would hurt. Let me help you once and then you can do it on your own next time.”

Max felt like he couldn’t say no. This is what Dylan was so excited about. Not even a full week over with and he was already about to have someone playing with his ass like a toy. He’d always known deep down that this was inevitable when he agreed but he had hoped to retain some leverage or dignity.

“Fine, you can walk me through the steps from the other stall in the bathroom.” Max had to negotiate his was around Dylan or he’d be fucking him next week.

“You drive a hard bargain, but that works for me IF you let me see the end product.”

Max had gotten out of having Dylan shove something up his ass, this seemed to be a fair enough compromise. “Deal.” Max said sweetly.

Max met Dylan in the bathroom and they entered adjacent stalls. Dylan handed him a douche, a bottle of lube, some baby wipes and the plug. Dylan walked him through using the douche and had him hold it in his colon for as long as Max could. Once he was clean Max lubed up the plug and prepared himself.

“Is it in yet?” Dylan asked excitedly.

“Not yet. I don’t see what you get out of this.” Max said as he pressed the tip of the plug against his tight ring. It slid in easier than expected, but as it widened Max started to feel his sphincter strain.

“I get enjoyment out of it, that’s all you need to know.” Max groaned as the plug spread him further. It was a large plug for a beginner and Dylan knew it. It was an inch and a half on diameter at its largest point and at least 4 inches long. The lube made it easy but at it’s widest the plug was starting to hurt.

“You want some help?”

“Nooooh” Max’s voice went from an annoyed statement to a pained groan as he pressed the final bulge of the plug past his battered ring and into his asshole. As it finally slipped through his groan faded into a moan of pleasure as his sphincter closed around the narrow hilt and a wave of electricity went straight to his loins.

“Sounds like you got it!” Dylan cheered, “now come show me.”

Max stood upright and felt the metal shift and press against his hole as he moved. It was a snug fit but there was something satisfying about it. As he gathered the rest of his stuff from the stall floor the plug would push in just the right way to send a wave of pleasure up his colon, radiating deep into his loins and to the tip of his cock.

“How does it feel?”

“It hurts and I can still feel it every time I move.”

“Good, you’ll get used to it.” Max stepped out of the stall with his shorts back on.

“Not yet, go bend over the sink and pull down your shorts, we had a deal.” Max felt uncomfortable but decided a deal was a deal. He pulled his shorts part way down and pulled his right cheek aside so that the jewel on the hilt of the metal stuffed up his ass would be visible.

“Shorts and panties off, I want a good view. And look into the mirror, I want to see your face too.” Max begrudgingly pulled down his shorts and stuck his ass out for Dylan. He looked in the mirror to see Dylan practically salivating as he stared at the jewel parting Max’s firm ass.

“Hey you didn’t say anything about pictures!” Max moved to pull up his shorts but Dylan was on him, pressed against his bare ass Max could feel Dylan’s manhood. Dylan gripped Max’s hips and leaned in. Max began to feel hot and his breath came in short gasps.

“I don’t have to say anything about anything. I could have you right here if I wanted to. Even if someone walked in, no one would care. They’d just watch me pound your tight little hole while they piss, might even want a turn.” Dylan whispered these threats into Max’s ear. Max pushed Dylan off him and pulled up his shorts.

“Don’t touch me like that again.” Max said, his voice wavering.

“You didn’t finish reading Tanya’s notes did you?” Dylan laughed. Max realized that with everything going on he had forgotten to finish them.

“You got what you wanted and you have your pictures.”

“I didn’t quite get what I wanted but this was enough. Thank you for humoring me today.” Dylan almost seemed sincere as he walked out.

Max stood in the bathroom for a moment trying to process. There was no doubt in his mind that if he let it happen, Dylan would have taken him right there in the bathroom. He was doubting whether he would have disliked it though. Dylan was gross but his body pressed against Max’s ass had excited him, he could feel the precum leaking from the tip of his cock, staining his panties. The raw feral instinct had almost taken over. He needed to stay composed or Dylan would walk all over him.

Max returned to the office and sat back at his desk. He immediately went to read Tanya’s notes, scrolling past the first 12 pages or so he got to something that was a little easier to read but not necessarily easier to digest. Tanya’s notes began to look more like a diary.

“Denver brought me to a client dinner today to show off. He likes to entertain the big clients and I’m happy to help him out. Dinner was nice and the client liked the way I carried myself. Denver seems pleased with my performance, hopefully I’ll get big bonus this year.”

“Dylan was rough with me today. He seems to take a sadistic pleasure in humiliating me. Out of all of them he always has some new task to make me feel low. Even Denver is respectful and he’s the boss.”

The notes went on like this for pages and pages. Always vague about what actually happened but painting a picture in Max’s head of what was to come. Max closed out of the notes, he couldn’t read anymore. He needed a plan to retain some dignity. Max decided that the butt plug was too far. Denver hadn’t approved it and Max would not wear it on Monday.

As the day ended Dylan walked past his desk. He winked and said “I’ll be up late on Saturday, make sure to stay by your phone.” Max shuddered. He was going to have to figure something out.

Harry was the last to leave and Max walked out to the elevator with him.

“How was your first Friday?” Harry asked casually.

“It was good.” Max responded, not wanting to get into it.

“I saw Dylan’s picture this afternoon.”

“He sent that to you?” Max felt ashamed.

“Yah, he sent it to everyone. You looked really hot with that jewel in your ass.” Harry continued speaking in a casual tone.

“Thank you.” Max was worried where this was going. “Does Dylan always send the pictures he asks me to take?”

“The boss likes them, especially when he’s on a trip. And Dylan likes the process of getting them.”

“So Denver approved the butt plug?” Max’s heart sank.

“Of course. Make sure you wear it when he gets back.” Harry noticed Max’s expression, “you don’t like it?”

“This all just feels very violating.” Max spoke honestly.

“You seem like you’re enjoying it.”

“Maybe.” Max didn’t know anymore.

“Well just keep me in the loop. If you’re not happy we can find someone else.” Harry offered no comfort.

“No, sorry, I do like it.” Max said

“It doesn’t go unappreciated. Like I said, you looked hot. I was getting excited in my office just looking at the picture, a little jealous of Dylan too.” Harry was now openly staring at Max’s ass stuffed into the short denims.

“Thank you. If I can ever help you with anything to pay you back for all your help, don’t hesitate to ask.” Max resumed his role and his flirt voice, the moment of honesty past.

“I’ll hold you to that.” Harry said as the elevator doors opened. “Have a good weekend.”