DAY 15: the office

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Ryan & Vinny

"Vinny, do I have any messages?" Ryan asked as he stepped into the office. Vinny shook his head, too nervous to speak. He had previously been told to keep his mouth shut, so that's what he planned on doing. Ryan was his boss and a very intimidating one at that.

"Follow me," Ryan demanded, his jaw tensing as he handed his briefcase off to Vinny and checked his phone on the way to his room. He closed his door behind himself, fumbling for his bag for a moment before realizing where it was. Of course, Vinny was standing outside the door respectfully, waiting to be let in. And when he was, he shut the door behind himself as to not anger Ryan.

"Sit." Ryan ordered, pointing to a clean spot on his desk.  He relaxed in his leather chair, watching Vinny uncomfortably hop up on the leather pad, putting Ryan's bag to the side.  He stared for a moment before spinning to face the windows.

"So what's the plan for today?" Ryan asked, watching the city pulse below them. 

"Uh well, you have two interviews this morning for the sales department.  And then you have a meeting before lunch with the accounting department, a lunch meeting with the investors, paperwork for the new office park, and then tonight is dinner with the few retirees." Vinny listed off.  Ryan spun back to face him, sighing.

"If you want I could reschedule..." Vinny offered as he looked over the paper that said what needed to be done.  Ryan stood quickly, pushing his chair away.  Without thought, he raised his hand and smacked Vinny's cheek, causing him to whimper. 

"I am the CEO of this company. Do you think I am incapable of handling my duties?" Ryan demanded a response as he set his hands on either side of Vinny's lap, bringing his face close to the receptionists. 

"N-no, not-t at all... Sir." Vinny whispered, carefully using his hands to cover his groin.  He was unbelievably turned on by having a man in such power over him.  Ryan smirked and scoffed as he noticed this. He stood up straight and looked over Vinny, making him squirm. 

"Well? Are you going to drop to your knees or what?" Ryan grabbed Vinny by the front of his olive green shirt and forced him to the floor. Ryan leaned back on his desk, looking out at the city as Vinny set a shaking hand on Ryan's belt. 

Ryan sighed and undid his own pants, pulling his stiffening cock from his tight boxers, as it was taking Vinny to long to do so.  Vinny's eyes went wide and he glanced up at Ryan to see what he thought, but he wasn't paying attention.  It was clear to Vinny that a blow job for Ryan was as normal as scrolling through his phone while watching television.  But Vinny was determined to make this the best blow job Ryan ever received.  If only he had a bit more experience. 

Vinny wrapped a hand around Ryan's lower shaft, stroking him firmly while wrapping his lips around his tip.  He sucked slightly while taking more of his length into his mouth, gagging as it brushed the back of his throat.  Ryan found this hilarious though and grabbed Vinny by his hair, slamming the rest of the way into him.

Ryan moaned as the gaging continued, eventually pulling Vinny off for a breath of air before forcing him back on. There was spit dripping down his chin and tears running down his cheeks, his esophagus burning and groin aching.  He tried his best to bob his head for Ryan, but he eventually pushed Vinny's mouth off of him and stood him up. 

"I'm sorry..." Vinny apologized, thinking Ryan was disappointed in him.  Ryan shook his head and snicked to himself as he yanked Vinny's jeans down, revealing a pair of loose checkered boxers.  Vinny bit his lip as Ryan tugged those down too, showing off the tight little jock strap he wore.  Ryan squeezed him tight through the thin fabric, causing him to cringe before he was bent over the desk. 

Ryan pulled a bottle of lube from his desk drawer, dribbling a bit down Vinny's crack before slicking himself up.  He popped the tip of the tube into Vinny, squeezing a bit in just to ensure things would go smoothly. 

Vinny shuddered at this bit of contact and pushed his rear back towards Ryan, in desperate need to be filled. Ryan noticed this and slammed into Vinny with no warning, causing him to let out a scream, which quickly became a moan. 

"Oh my god." Vinny huffed under his breath as he clung to the edge of the desk, his knuckles turning white.  He was breathing heavily as Ryan began to move a bit, starting with shallow thrusts.  But these shallow thrusts quickly became deep thrusts where Ryan pulled almost all the way out before slamming in to be balls deep.

Ryan hooked a set of fingers into Vinny, pressing down into his prostate as he continued to ravage him. Vinny whined and shifted and teared up as the pleasure became too much for him and he came in his little panties.  He constricted around Ryan, milking him dry. 

Ryan pulled out slowly, giving Vinny's hole a kiss before cleaning him up and sitting him on his desk again.  Ryan relaxed in his desk chair, staring up at him with a smile.

"So what's the agenda again?" Ryan asked.

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