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Chapter 23
by
Lossleader2
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Surprise party
Max was finishing slurping down Denver’s warm seed on a Monday, enjoying the flavor and texture, when Denver said casually.
“It’s Harry’s birthday next week. Did you know that?”
“No.” Max said around a mouthful of cum.
“I got him a vacation package, you can use the company card but you should get him something.”
“I don’t know what to get him.” Max said. He took a deep breath through his nose as he pressed it against the fading swell of Denvers shaft, his chin resting in the folds of his warm orbs.
“You know what he likes by now.”
“Not really. He doesn’t talk about himself that much.”
“Well, you have a week to figure it out.” Max got out from under Denver’s desk and knelt on his pad. Denver looked down at him, enjoying the view. Max’s tits were growing in and he dressed to show them off. Denver smiled a little. “You look really good Max.”
“Thank you sir.” Max blushed a little.
“You’re really coming into your own lately.” Max had been embracing the debauchery of his lifestyle more this year. Between sex clubs with Tara, his morning routine with Denver, and the constant groping and flirting around the office Max had become a new sexual being.
“I think I’m getting the hang of it sir.”
“Part of me wants to split you in two, but I wouldn’t want to ruin a good thing.” Max’s heart skipped a beat.
“I’ve been practicing.”
“Oh yah?” Denver chuckled as if the thought of it was even ridiculous.
“I have.” Max pouted.
“Well good. I’m glad you have such a strong work ethic.” Max smiled and Denver dismissed him. He practically flew through the office. Denver wanted him. Max stopped by Harry’s office next. He was unshaven and looked tired.
“Long night?” Max asked.
“A bit.” Harry looked up at the young secretary and smiled. “You look good.”
“Thank you. Anything you need help with today?”
“I think I’m all set for now.”
“Harry, what do you want for your birthday?”
Harry looked surprised. “You don’t have to get me anything Maxine.”
“I want to. You’ve always been too good to me.”
“Well not too good.”
“I like when you’re not too good.” Max smiled knowingly.
“I don’t really need anything right now.”
“Well I’ll figure something out.”
“You really don’t have to.”
“Maybe I’ll get you a set of nice leather whips and you can test them on me.” Max teased.
“I’ve got some of those.” Harry winked. Blood rushed to Max’s crotch.
“And yet you never bring them in.”
“Maybe I will sometime.” Max left disappointed as usual. He pondered what to get Harry for his birthday. Maybe he could get him tickets to one of the private shows Tara had taken him to. Or book a room and meet him there. Maybe this was his chance to lure Harry to him. He brought this idea up to Tara and she liked the idea. She even recommend another club that was a little swankier and had bigger private rooms. Max called them and with Tara advising him as he talked to the club he booked a room for two weeks from now on a Saturday. Tara also helped him set up a backup girl if Harry didn’t want to go with Maxine. Max didn’t like the backup girl idea but Tara had a connection through a friend that said she could cancel last minute free of charge so Max agreed.
The next Wednesday Max went to Harry’s office with a wrapped box before Harry came in. Inside the box was a note MX wrote and a printed out “ticket” with the reservation information. The note read:
“Happy Birthday Harry!
I didn’t know what to get you so I took a leap and chose something risky. I think you deserve a night of no stress enjoyment. I will be at the reservation enclosed in this note, waiting for you. If you don’t want me to come, I also have someone that can take my place, so either way you get to go wild with someone. I hope you enjoy and I hope to see you there.”
Max had also put on lipstick and signed the letter with a kiss. He was a little embarrassed of the whole gesture and the backup girl felt lame but Tara had encouraged him to go through with it and he decided it was his best chance. He left the box on Harry’s desk and went to join Denver in his office. He spent the rest of the day waiting anxiously for Harry to say something to him about the gift. He walked by his office every chance he got but his door was closed each time he tried to peak in. Max stayed behind past the normal time he left hoping to catch Harry.
Finally Max heard Harry coming. He adjusted his sports bra to show off his tits and waited. Harry opened the door behind Max and stopped at his desk. He had a wide smile on his face.
“Maxine I told you no gifts!” He held up the un touched package.
“You haven’t opened it yet?” Max couldn’t hide his disappointment.
“Sorry, I was on calls all day. Should I open it now?”
“Yes, yes open it!” Max was excited and nervous and wanted to rip this bandaid off. Harry tore up the wrapping paper neatly and opened the box. He read the note and the reservation printout. And said nothing for a bit.
“Maxine.” He trailed off.
“I can call the backup girl if you want.”
“No, no that’s okay. Are you sure?”
“Of course I’m sure.” Harry was quiet again and then it was like realization dawned him and he smiled.
“Well it’s a date then.”
“Yay! I’m excited. Just tell me what you want me to wear. They provide everything else. I got a big room with every amenity. There’s a bunch of toys and tools and equipment and we have it booked for like 5 hours.” Max was giddy with excitement.
“That sounds incredible. You’re sure that you’re sure?” Harry was serious.
“Yes Harry.” Max straightened his face to show he was serious.
“You know what I want to do to you?”
“I don’t, but you can do anything you want.”
“We’ll see. Safeword is ‘pineapple’ okay? I’ll remind you.”
“Pineapple, got it.”
“I will send you a list of positions and things that you should look over and make sure you’re okay with.”
“Harry, cut the red tape. You’ve seen what I do here. I agree to whatever you want to do to me.”
Harry smiled. “Thank you Maxine. I’m so excited, I needed this.”
Max was overjoyed as he walked home. The next day he told Tara all about it and she smiled and congratulated him.
“I told you!”
“You did! Thank you so much!”
“Just make sure you’re ready for it. He sounds ****.” Tara warned.
“I mean what’s he gunna do? Shit in my mouth. I think that’s the only thing he could do that I wouldn’t be okay with.”
Tara laughed. “I think you’re good on that front.”
Max spent the rest of the week doing research into the club and bdsm. He watched videos and googled how to use safewords and what the rules were. Harry had sent a list of things to look into as well over text. Max recognized a lot of it from his own research but got a little nervous as he read through some of it. The list included what Mad expected, things like whipping, caning, enemas, and bondage positions. It also included anal pears, dilation, clamps, and other **** acts that Max had never even considered. Eventually he decided to just ignore the list. He didn’t want to know everything and he also was worried that it would scare him off. He wanted this badly enough that he decided he wouldn’t let an anxious feeling deter him.
The next two weeks were their own kind of ****. Every day felt like it was moving slower than the last. The things that usually got him excited felt boring in comparison to his anticipation for next Saturday. Even his mornings with Denver felt routine. Denver seemed to sense this as Max’s thoughts lingered while he swirled the head of Denver’s cock with his tongue.
“Everything alright Maxine?”
“Yes, sorry.” Max said with a mouthful of precum.
“I can tell your mind is elsewhere this week.”
“Sorry Denver. I’ve been caught up thinking about Harry’s gift.”
“Ah, I see.” Denver seemed to know about the gift Max had offered Harry. “Just remember, at the end of the day you’re mine.” Max was surprised by the sudden possessiveness.
“Of course sir.” Max redoubled his efforts, swallowing as much of his bossed snake as his throat could handle, which had become a considerable amount with all of his practice.
“I don’t mind pimping you out to my employees, but there’s a reason you’re in here every morning. Don’t forget who brought you in and made you what you are.”
“No sir, I’m yours, I’m here to please you.” Max begged between gasping breaths as he prepared to jam his throat full of Denver’s meat again.
“Good. Perhaps I’ve been a little too easy on you.” Max choked as his windpipe was pinched closed, his throat bulged as he **** his nose closer to Denver’s pelvis. As he fought the urge to breathe he began massaging Denver’s leathery sack with his hands, coaxing his orgasm. Denver groaned and finished into Max’s quivering throat.
Max stopped by Harry’s office a few times in the week leading up to their date. Harry was in an excellent mood and was even flirtatious with Max.
“Need help with anything Harry?”
“You’re about to be giving me all the help I’ll ever need.” Harry grinned like a kid on christmas as his eyes pored over his gift.
“I hope so.” Max did a little spin.
“Give me a little peak at my gift would you?” Max pulled down his black denim shorts to reveal his caged manhood. “It’s wrapped and everything. By the way you don’t have to wear that on Saturday okay?”
“Music to my ears.” Max smiled and turned to bounce his ass in front of Harry.
“Give me a spread too pretty please?” Max obliged, pulling his toned cheeks apart to let Harry analyze his tight entrance. “I cannot wait.” Harry sounded almost menacing, Max got excited.
“I guess you’ll have to wait a few more days.”
“What if I didn’t want to?”
“You want your gift early?” Max bent further forward and spread his legs so that Harry could see everything.
“Yes, but no. I don’t want to ruin the fun.” Max pulled his shorts back up in disappointment.
Max met with Tara for drinks after work on Friday. They had been going to the gym 3 days a week together and it had become routine to grab a drink and chat on Fridays after their workout.
“Tomorrow’s the big day.” Tara teased.
“I’m so excited. I can’t tell you how much I need this right now. This week was ****.” Max sipped his wine, his mind elsewhere.
“Tomorrow might be **** too.”
“God I hope so.”
“You’re funny. I remember the shy girl who didn’t want to shower naked at the gym not too long ago. And now you’re pissing your pants excited to go be your coworkers little sex toy.”
“Life comes at you fast I guess. Your influence probably didn’t help.”
“No, probably not. Well, I hope it’s everything you want. Be ready for some surprises.”
“I’m ready for anything.”
“I guess we’ll see.” Tara sipped her wine and watched her friend ruminate in anticipation.
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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
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