December

December had arrived and Max’s routine was down pat at this point. He would doll himself up at home, walk to work, suck Denver’s dick and take his advice or belittlement or compliments and then fend off the analysts and associates as they attempted to get any piece of him they could. When he arrived home he would be so wired from the day that he would unwind by working out at home and then ride his dildo to unwind from that.

It had all become so routine at this point and Max could barely process any of it. His breasts had become sore, growing at a surprising rate they now showed if he didn’t wear a bra of some kind. They were still small but it was clear his body was not that of a typical guy his age. His parents had taken notice of the changes. His long dark hair and smooth hairless skin complimented by his burgeoning breasts were hard to hide every time he saw them and it had become obvious he was going through changes. To their credit, they didn’t say anything about it to Max and he didn’t know how to bring it up without telling them that he was functionally an office sex ****. His dad did suggest that he join a gym and Max felt that this wasn’t a bad idea. If he could put on some mass he might be able to mask some of the changes. They researched gyms near him and he found one in his price range that seemed relatively high end.

Harry had been absent for about a week and when he came back he immediately asked Max to join him in his office. They had not spoken much lately and Max had been wondering what he’d been up to. The day he called him in Max was wearing a pair of assless chaps, a tight leather top, a collar and a ring gag. It was an outfit requested by multiple analysts which made it tough to turn down but the assless chaps felt like an on the nose joke about Max’s recent foray into anal poundings.

Harry looked Max up and down a little confused. He didn’t say anything but Max could tell he liked the way he was dressed. Harry looked haggard on the other hand. His normal clean shave was an untamed short beard, his hair wasn’t gelled the way it usually was and his suit wasn’t professionally pressed.

“Maxine thank you for coming in to talk to me. I have need of your assistance. You can take out the ring gag, I don’t need drool on my floor.” Harry seemed almost annoyed.

“Sorry.” Max said submissively.

“It’s okay, I’m sorry for being rude. I am dealing with some stuff at home and I am now also in charge of planning the christmas party, which is where I need your help.” Max nodded. “Will you go around the office and survey everyone to see what kind of entertainment they want? I have you doing some but I need to know who else to hire. I need preferences on hair color, skin color, measurements, and of course whether they want dick or pussy or both.” Max was confused.

“What are we ordering?”

“Prostitutes Maxine, please keep up.”

“Right, sorry.” Max felt awkward but asked anyway. “Both?”

“We’re ordering multiple and I need to know if they want prostitutes with dicks or pussies and how they like them.” Harry said hurriedly.

“Gotcha, I will go around and ask.”

“Thank you. Also, I have you down to sing, strip, and do a santa thing, is that good?”

“I can’t sing.” Max had already resigned himself to the fact that he would be playing whore at this thing so he was almost happy to hear the word strip.

“Hmm fine, strip and santa thing it is.”

“Whats the santa thing?”

“You’re just going to help deliver little gifts to everyone, it’s doesn’t require much.”

“Okay.” Harry looked stressed. Max felt bad for him and decided that this was probably where Denver would want him to exceed expectations. He turned around and put his hands against the wall and stuck out his ass, which was bare except for a thong. He shook it a little bit. Harry looked at him and chuckled.

“I’m sorry Maxine, that’s nice but that’s not what I need right now.”

“What do you need?” Max mustered his most seductive voice. Harry looked at Max like he was seeing him for the first time today. His eyes got that hungry look they’d had the last time he’d taken sexual favors from Max.

“Bend over my knee.” He scooted his chair back and pointed at his knee. Max hesitated and Harry stared him down. A small cold fear shot through Max and he bent over Harry’s chair, both arms resting on the left armrest, his pelvis up against the right. Harry began caressing Max’s supple ass, fondling the exposed skin and molding it in his hands. Max let a small moan escape his lips.

“You’ve come a long way in such a short time.” Harry rubbed one of Max’s ass cheeks and then delivered a light slap. Max yelped but held his tongue. “I almost forget sometimes that you’ve been deflowered.” Another slap, this time harder. A crack sounded through his office. Max bit his lip at the small spurts of pain. “Just because Denver likes you everyone keeps their hands off, theyre too scared of him.” Another slap to the same cheek, Max started at the pain and his ass buzzed. “You’re the one who should be scared, not me.” Harry squeezed Max and slapped him again. “Are you scared?” Harry whispered in Max’s ear.

“No sir.” Max moaned.

“That’s why they like you, you’re a natural born slut.” Harry slapped Max’s other cheek, the first one was turning red. “I like my meat a little less pampered.” Harry delivered two harsh strikes to Max’s ass and Max began to feel the rawness more with each blow.

“I’m sorry sir.” Max said, a little bit of fear creeping into his voice. He’d never seen Harry angry, but this was close. Harry mangled Max’s ass and slammed his hand down hard with a crack. Max yelped again and tears welled in his eyes. “I’m sorry sir.” Max repeated again. Harry delivered several more slaps, each as hard as the last. Max had tears in his eyes now and his ass stung more with each slap. “I’m sorry sir.” Max cried.

“You better be sorry.” Harry reached between Max’s legs and groped his caged cock. “You walk around here caged and you still act like Denver’s favorite student.” Harry squeezed Max’s tender testicles and Max’s stomach turned. He yelped again.

“Please sir, I’m sorry sir.” Max pleaded with Harry. His cock fought against its cage.

“You’re a pet, you’re less than a pet. I don’t beat my pets.” Harry struck Max’s ass again. Despite the pain Max was relieved to have Harry’s grip release from his balls.

“Yes sir.” Max said.

“You go in there every morning and suck Denver’s cock. You’re like his personal little sex pet. You forget your place!” Harry gripped Max by the testicles again, squeezing tightly and Max cried out in pain. Harry’s hand covered his mouth but his grip didn’t loosen on Max’s tender orbs. He mangled them in his hand and Max squirmed and bucked as his stomach cramped and turned. Tears streamed from his eyes. Harry released his grip and Max gasped through the hand holding his mouth. Harry yanked the plug from Max’s ass in one forceful pull. Max screamed into his hand. Suddenly the warm plug was shoved into his mouth.

“Shut it. This is the treatment you should be used to be now.” He covered the plug in Max’s mouth with his hand again and delivered another slap to Max’s ass. The metal plug tasted like lube and his own hole. On instinct he circled it with his tongue and had to stop himself.

Suddenly Max felt his sphincter spread as Harry shoved two fingers into Max. He moaned and Harry shoved in a third. His ass had become a much more welcoming hole and Harry noticed.

“You get ass fucked one time and your hole is already this loose?” Harry clawed at Max’s insides, burrowing deeper with great effort. Max let out something between a cry and a moan. “You gunna break this quickly on us sissy slut? You haven’t even begun to do this job. When we’re done with you you’ll be begging for cock on the street.” Harry pulled and plunged his fingers, twisting and lunging as if to try to touch every inch of Max’s colon. Max bucked his hips, unable to control the instinct to ride Harry’s invasion. Harry released his hand from Max’s mouth and pulled the plug out. Max gasped for air. He pushed Max between his legs and stood up. He unzipped his pants and pulled out his large white cock. He slapped Max across the face.

“You should be stopping here after Denver every morning you dumb slut.” He slapped Max again. Max was crying. Harry stroked his erection over Max, be knelt a little and dragged his sack across Max’s face.

“That’s right where you belong. Lick my fucking taint.” Harry was swept up with lust and anger and Max began licking his sweaty taint. He tasted his ballsack and smelled his odor. It wasn’t like Denver’s, it wasn’t unpleasant but it wasn’t pleasure able like Denvers was. Harry stroked vigorously and Max felt his orgasm coming through the sack on his forehead. Harry pulled back. “Show me your little tits.” Max pulled down his top and Harry sprayed him with his orgasm. Harry stopped stroking and sat back down in his chair with Max’s cum-soaked body between his legs. He seemed to almost wake from a dream and looked at Max.

“I’m sorry Maxine, that was too far.” He grabbed a tissue and helped Max clean up.

“Its okay.” Max said, not sure how to feel.

“Its not, i didnt mean that stuff. Youre doing a great job.” Max left the office with cum on his clothes and shame in his gut. He didn’t understand Harry and now he was scared of him. Max’s cock was extremely uncomfortable as the cage strangled his arousal. He wiped his face and smeared make up and went and replaced the butt plug, wincing as it irritated the sensitive area where Harry had dug his fingers in. His dick had a mind of its own as it strained against its cage. Here he was wiping tears from his eyes and massaging his injured orifice while his libido begged for more.

Harry was extra kind the rest of that week and the next. He bought Max flowers for his desk and candy in a christmas themed box. Max was perplexed by his fluctuating behavior. One morning as he wiped Denver’s orgasm from his lips he asked

“What’s up with Harry?”

“What do you mean?”

“Sometimes he’s the nicest guy in the office and other times it feels like he wants to hurt me.”

“Ah, yah. Harry’s a complicated guy. He and his wife are separated and I think he’s having trouble with that. He was also one of the first secretaries we had back in the day. Back then it wasn’t as established, the position didnt have as many responsibilities as it does now, but I think he sees himself in you a little.”

“Wow, I would never have guessed.”

“Trying to picture Harry with a ball gag?” Denver chuckled.

“Did he wear one?”

“Once. Like I said, it was more of a hazing thing back then. He wasn’t in charge of keeping morale up, we outsourced that stuff. But that got expensive and that was when we hired Tanya.” Denver seemed almost nostalgic.

Max thought about this as he licked up the remains of Denver’s load off the ground. Once he was dismissed he went by Harry’s office.

“You wanted me to come by after Denver’s right?” Max asked innocently.

“No, sorry Maxine that’s not necessary.”

“Okay, well if you change your mind, you know where to find me.” Harry watched Max’s ass as he turned to leave.

“I only make love to my wife. My tastes are probably a little **** for you.” Harry said as he left.

Max turned and winked. “If you let me have some fun too I’m happy to try anything.” Harry smiled.