My Boss is a Masochist (w/KaseKatty) | NSFW

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Aalyiarah

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The endless scroll through LinkedIn’s feed had become boring half an hour ago, but he was waiting on the meeting to end before going into his boss’ office. Greyson was caught up with his work, he prided himself on his work ethic and being a perfectionist since he could recall he had groomed himself to be nearly flawless with his work and hardly had to double check a single e-mail or document that he wrote. The office was busy, and he had meant to see his boss before the meeting had started but a need to pee had caused him to miss his window of opportunity since the bathrooms on their floor were all out of order. A phone call would come through, he’d answer but end up taking a memo. Another task complete and he was still bored. Looking at his black matte apple watch as it told him to stand. Just as he would the door opened and the two potential clients were about to leave. “I have your car coming to pick you up,” bowing slightly in respect after tapping a few times on his watch, making his statement true. They would offer him a hand to shake but quickly headed off.

Smoothing out his black pinstriped button-down shirt, and grey tie, Greyson used the voice commands to set aside thirty minutes putting all means of contact with him on hold. Stepping into the office, “well, you have a small window of downtime.” A smug expression tugged at his lips, “I’m bored. This job doesn’t challenge me and that is why I must punish you.” Dark brown orbs looking over through the clear lens. “We won’t be interrupted. I have booked us the next half an hour.” Walking over to the nearby bookshelf, a well-manicured hand reached out grabbing a well-designed mock book that housed a small compartment. “It’s been a while since we have used these,” holding up a string of anal beads, “too long wouldn’t you say?” Approaching the other’s desk, “we can do this your way or mine…” The strand measure over fourteen inches in insertable length with each ball getting wider starting with half an inch and going up to two and a half inches. Letting the anal bead string fall into the desk with a thud these weren’t your typical beads but each one was weighted to add to the fullness feeling.
 
Vincent was a shorter man at 5'3, his stronger personality made up for the height. He always showed authority so no one looked down on him despite how they were taller than him. He wasnt as meticulous as Greyson but he did keep himself clean and proper looking, his hair slicked back except for a few strands the the gel could seem to hold down. He had been glad he was so busy. He knew what would happen if Greyson go the chance to be alone with him. He tried to keep the meeting with his clients going for as long as possible. He was glad Greyson missed the first window. When the clients left he sighed and looked at his paperwork hoping Greyson was busy.

Vincent tensed up slightly hearing Greyson speak. He looked up at him but stayed silent he couldnt think of an excuse yet. Vincent saw Greyson grab the book and turned dark red seeing the anal bead "i had forgotten those were there. " it had been awhile. he knew every toy Greyson had used so far. He had photographic memory but if he was overworked he sometimes forgot things. Vincent looked at Greyson when he spoke trying to make a bit of an excuse " i still have to file all my paper work. I dont have the time for that. " he said straight forward his face red as he go hard just looking at the toy. Vincent picked up his paper work and looked through it. He was trying to act like he didnt want to but when he rolled his chair back to open a drawer on his desk the bulge in his pants was visible.
 
“Lair.” Greyson coldly spoke his eyes peering down as Vincent rolled back in his chair, the red coloring of his once pale skin and the bulge in his slacks verified that his little slut wanted to be forcefully filled. “Paperwork can wait,” grabbing the papers and with a twitch of his wrist Greyson tossed them onto the floor on the other side of his boss’ chair, “Oops.” Watching as the submissive male went to pick them up having to turn away from him. At that moment he’d grab Vincent by the wrist and twist his arm up behind hind his back. “Don’t talk back to me,” shoving him into the desk Vincent’s crotch used to shut the drawer with the motion. Bending him over letting his chest strike the desktop. “Mm, it’s so tempting to fuck you right here, but you’d like that too much.” Adding pressure to make sure the other wouldn’t move too much, Greyson manipulated Vincent’s hips pulling him a little away from the desk. Reaching around him unbuckling the belt that was keeping his prey from him, Greyson worked the belt, button, and zipper skillfully and soon a cool breeze would grace over his boss’ newly bared backside.

Reaching for the weighed anal beads Greyson adjusted the way he held them before rubbing the slight tip of the first tapered ball against his pet’s dry ring. “Don’t scream. You don’t want the employees to know you like things shoved into your ass,” he’d push the half in thick velvety-soft ball passed the ring of muscles watching at it deliciously stretched Vincent’s ass. The strand now hanging out there were two balls left. Letting go he’d smack the bubbly backside forcing his toy to tighten before shoving in the next ball in, this one a little thicker at one and a fourth inch. “Keep that ass clenched.” Ordering as he let go of the strand to reach under and grab his boss’ harden shaft. Greyson then released Vincent’s arm. Tugging on the beads and shoving Vincent’s cock into the open hole grip piece on the strong retrieval cord which was meant to be used to pull the beads out but was being used as a cock loose fitting cock ring. “One more,” the final bead was inserted, this one he had to use more than his thumb to press its girth to pass the small entry. “How does that feel, pet?” Greyson smirked. “Now, don’t you have some paperwork to do?” He’d turn around, unlock the door, and slip out leaving his boss exposed and little time to get himself presentable.
 
Vincent was a bit pissed when the papers landed he had just organized that stack. He had gotten up and bent over to pick up the papers. They were still somewhat organized. When he was grabbed the papers flew out of his hand now they were messed up completely. Vincent didnt fight much, he couldnt Greyson was stronger than him. He didnt struggle as his pants were removed, his cock hard as a rock. Vincent would much rather be fucked than what he knew was gonna happen.

Vincent clenched his teeth as the first ball went in it hurt but he still enjoyed it. When his ass was smacked he immediately tightened up it was a trained response. He tried hard not to moan but it felt so good. He let out a pleased moan when the last one went in. The ring around his cock pulled on his cock if moved too much. His face was a deep red as he panted softly. When Greyson left he collected himself and fixed his pants he found it hard into move without wanting to moan but he tried to keep calm and collected. He put all the papers on the desk and sat down organizing them again. When he sat down the bead went a little bit deeper. He tensed up and stayed where he was. If he stayed sitting he could bear with it until he got home.
 
Sitting down at his desk Greyson refreshed his Boss’ Calendly page, there were two new bookings, both for this afternoon. Picking up the landline at his desk, Greyson placed the phone to his ear and hit the extension number. The phone rang out a couple of times before he heard the voice on the other line, “Vincent, I wanted to let you know that you have a 2:15 and a 4:00 today.” Reading over the content of the requests, “your 2:15 is in the Office with…” explaining all the details of the booking and even updating his boss on the client a little to make sure he was up to speed. “While your 4:00 is an early dinner with the mayor, we will be meeting him at the Steak House.” Oh, this was too good for Greyson and there was a slight enjoyment knowing how hard it was going to be for Vincent. “Should I confirm these appointments, boss?” Even if he was told no he would still confirm the 2:15.

One of the mailroom attendants walked up, “Mr. Greyson?” They were holding a package that wasn’t labeled other than the basic delivery address. Handing over the package, the boy would ask for him to sign for it before heading off. Checking the time, it was only 2:00. They hadn’t needed the entire thirty minutes he had booked, but there was still fifteen minutes before the meeting and clients weren’t normally early. “Melissa, please take my calls,” asking politely with an award-winning smile. The girl would swoon and nod allowing him to leave his desk once more and return to the office with the package in hand. “I’ve been thinking about how neglectful I may seem, so I wanted to get you something. It just came in.” Inside the box, Vincent would find a 'gates of hell' chastity device. Each of the four rings are hinged for a better fit and more manipulation. This cage is meant to be held upright when the detectable urethral insert slides deep inside. An Allen wrench is included to clamp the sound in place once it’s shoved in as deep. The hollow core allows liquid such as cum and piss to pass through while the device is worn and the sub is trapped. “My favorite part is the sounding rod…” Greyson commented crossing his arms over his chest.
 
Vincent heard his phone ringing and pick up "yes Greyson? " he listened to everything Greyson said. When Greyson finished Vincent spoke after a somewhat frustrated groan. " confirm both appointments. " he wasnt going to let anything get in the way of work. Work was somthing he took seriously. His professional image is important to him. Its why there things Greyson does turns him on. He likes when he has to try hard to keep up his professional appearance while he feels like he wants to be a moaning mess.

Vincent groaned when Greyson walked in. He looked at the device in the box. He knew exactly what it was hed found it before when curiously looking at toys it was actually something he had saved. Vincents face turned a deep red "i think the beads are plenty i cant got to dinner with the mayor with this on. He knew his words werent going to change anything but he tried.
 
“Come now, I’ve been way to lenient on you lately,” Greyson responded looking at his apple, “we have twelve minutes.” Uncrossing his arms with a smug smirk, “there have been some change of plans, I won’t be joining you for this dinner since you never added a plus one.” Actually, Vincent had, but Greyson went over event logged in as his boss and changed it. A setup to try out a new device while giving his superior a low blow to his pride. “By the time this was brought to my attention today, it was too late for the RSVP to be changed. We both know how the Major hates change.” Stepping behind the chair, looking down at the much shorter male that almost looked like a youth sitting in the large executive chair. Pulling him away from the desk and turning the chair on the swivel to face him. “I need to make sure that you don’t get excited too much, have you looked at the itinerary for the dinner. No?” Squatting down before his boss, swiftly work the zipper on his slacks down once more. “You have dinner at 4:00 then you will be meeting up with him and several of the county commissioners at Traps and Tramps.” Knowing that the way he had inserted the beads and used the handle as a cock ring would make much wiggling painful Greyson didn’t expect his pet to fight him. “I looked up Traps and Tramps and that is a strip club. There is no way in hell I am letting you go there. I can’t trust you to behave.” Pulling Vincent from his boxers Grayson grabbed his sac firmly giving him a rough squeeze, “you’re a little slut after all, and still, need a lot more training.”

Grabbing the Chasity device, he’d lock him in place utilizing the small lock that came with the toy. “Hmm, before you leave I’ll add in the sounding rod. Make sure you go to the bathroom beforehand,” Greyson’s phone buzzed, “you’re 2:15 will be here in five minutes, fix yourself.” Grabbing the box Greyson would start to break it down as he exited and returned to his desk to dress the members of the next meeting.
 
Vincent wasnt stupid "you removed yourself didnt you? I know i added you to come with me" vincent groaned and watched him he looked up at the taller male with an unhappy expression. He was upset yet he couldnt stop Greyson. Vincents face was red as his cock was pulled out. He ried to move only to let out a soft moan. When Greyson mentioned the strip club he spoke "i dont like strip clubs you know th..." He was cut off by a quiet moan when his sac was squeezed. Vincent groaned when when Greyson was done he was so turned on but also embarrassed at the same time hopefully no one would notice anything. Vincent slowly fixed his clothes. He sat in his chair and tried to hide his big boner he had as the men walked in. He stayed seated but politely greated them and offered his had. He had calmed himself enough to look professional
 
Greyson, proud of his work, as he set down at his desk couldn't help but think about Vincent. His ass stuffed with weighted anal beads, the circular handhold on them used as a makeshift loose fitting cock ring and his cock caged making it painful for him to have an erection. Those thoughts caused the groomed man to groan slightly which was masked as him clearing this throat. Greyson enjoyed having such control over his boss it made him feel empowered. As the workday came to an end, and the 4:00 meeting ended, Greyson signed out of his computer then walked into his boss' office. "Vincent, how are you feeling?" Shutting the door, locking it, and approaching the other's desk. "I expect you to be home no later than eight o'clock. That is plenty of time to entertain and build up your rapport with the major." Speaking firmly his eyes never leaving the other's gaze. "If you are late...well, we haven't had a live dungeon show in a few weeks. I'll get everything set up just encase you are late." Looking down at the man's lap, "I hope you have peed." Ordering the smaller framed male to reveal his cock, Grayson pulled out the sounding rod from his pocket. "This thing will be locked in place," holding Vincent's dick upright Greyson shoved it in the thick piece of metal sliding down the small slit. Those deep moans causing his cock to surge, forcefully twitching in his slacks. Locking the rod at its max depth, "but before you go.," he'd reveal his own harden endowment. "Get on your fucking knees and suck my cock." Grabbing a handful of Vincent's hair he'd pull him roughly encouraging him to move onto the floor.
 
Vincent tried hard to stay professional with his clients so far he was doing pretty good. Once done he sighed he remembered to use the restroom before the end of the work day. When greyson walked in vincents head was on his desk and he groaned. It hurt but he was staying hard, he enjoyed the pain. He listened to Greyson and nodded gulping slightly "i wont be late" when order Vincent didnt hesitate to listen he pulled his cock out for Greyson. He was still really hard, precum dripping from the tip. He let out some moans as the rod went in. Vincents face looked lustful when greysons cock was pulled out. He gasped softly as his hair was pulled and happily went to his knees. The one thing he was really good at was sucking cock. He took greysons cock in his mouth and swirled his tongue around as he moved his head. He looked so pleased as he sucked the cock he loved so much.
 
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