Arin's Assistant.

There was nothing about my job that I would change. I loved it. I wouldn't want to do anything else. When I landed the gig to be a personal assistant for Arin, "the video game boy" Hanson, I had no idea that I was going to have the time of my life. Arin was probably the best boss I ever had. Each day was something different, and in the 8 months I had been working for Arin, I had gotten pretty close to him. I walked through the front door of the game grumps building with two boxes of donuts In my hands. Fridays were always the most chill day of the week, so I decided to sweeten it by bringing everyone's favorite. I placed the boxes down in the break room and made my way to my desk. At the beginning of the day, I was often alone. The rest of the grumps came in around noon. I started up my computer and waited for the machine to start up. I walked over to the coffee maker. I opened the top cabinet with a groan. There was no more of my favorite brew, so I checked my backup stash in the bottom drawer. Still none. No one touched the Starbucks Caramel brew, so seeing it empty was pretty annoying. I mumbled to myself as I made my way to the break room closet, "I guess the office assistant didn't fill it up.". The doorknob turned slowly and I pushed it open. "Ah!" A shrill scream echoed against the closet walls. Arin screamed back, and his hands came up to shield his face. I noticed that he did not have pants on. I closed the door halfway to still be able to get some sort of explanation through the crack. "Miranda, what are you doing here?" Arin called out. His voice wavered as if he had just woken up. "Me? What are you doing here? Why are you not wearing pants in the only closet that has food?" I questioned, I could hear Arin zip up his pants as he pulled the door open from the halfway point I held it at. "Trust me, you don't want to know," Arin mentioned casually. He pushed past me and walked over to the break area where he noticed the donuts. I couldn't help but wonder further. What was Arin doing in there? "You weren't like…in there, were you?" I walked closer as Arin washed his hands before grabbing a donut. I could feel my face heat up. "You don't want to know, Miranda," Arin spoke more sternly. I couldn't help but flinch at Arin's unnaturally harsh demeanor. I nodded and grabbed a donut as well, completely forgetting about the coffee. It wasn't important. "Well, do you and Avidan have something going on today?" "No," Arin answered shortly. It wasn't normal for Arin to be so blunt with me. Most of the time we made fun of each other. "Okay, well I guess I'll get to work." I wrapped a napkin around my donut and walked off into my office. The office is directly outside of Arin's. If you could even call where Arin worked as an office. The computer had loaded up to the sign-in screen and I began to work. I watched out of the corner of my eye as Arin walked around and through his office door. The air remained silent after the encounter but I didn't particularly mind it, at least until I heard whining coming from the other room. I turned my attention to the direction it was coming from. What the hell was going on? I locked my screen and stood up, turning my body towards Arin's office and I pressed my ear to the door. "Please… oh please," Arin whined again. A soft slapping sound made its wait through the door. "I just wanna c*m. Please." My eyes widened and I slowly pulled my head back. So he was jacking off in the break room closet! Gross… "f**k, no. No, please." Arin pleaded. Another groan followed. "Come on." His voice broke, something I hadn't heard from him yet. What happened to Arin? Why is he so troubled right now? I took a deep breath and knocked on the door. There was a still moment before Arin answered. "Come in." I slowly opened the door and peeked through the opening. "I hate to say it, but you're a bit loud." I c****d my head to the side and noticed Arin slumped in his chair. "Can you please tell me what's going on? You sound like you're hurt." I stepped closer and closed the door behind me. "I have blue balls." Arin blurted out. "Is that what you want to hear? My d**k has been semi-hard for days and I have tried jacking off to no avail. It feels raw and the pressure in my balls makes me want to bash my head against the wall.” I stood there with a confused and shocked expression. "I-Oh." I didn't really know how to react to what Arin said, but I knew he must have been pretty irritable if he was willing to snap at me like that. "What methods of m**********n have you tried?" I asked calmly, I've had odd conversations with Arin before. Of course, he is an odd person. We've gotten drunk together after work, and I've learned a lot about his s*x life. I kept mine mainly to myself. "What?" Arin asked. His anger dissipated, and he looked at me like a deer in headlights. "You obviously need some assistance, and I'm your assistant. So what have you tried?" Arin's face turned bright red, and he shook his head. "Just playing with my d**k. I guess." I nodded and pulled my hair up. "Okay, have you tried fleshlights? Vibrators? Are you into anal play? I have Domme Demi's number from the gentleman's club we went to. I'm sure she would love to help you-" "N-No it's okay. Uh, I've never tried to put anything in my butt, and I don't think I will. I know there's a G stop in there, but it's gotta hurt to get to it." Arin stood up, and I looked down to see a tent in the front of Arin's pants. He signed and flinched as he tried to adjust himself. I nodded in understanding. "We'll all of my exes were super into it, but I'm not a guy. So, I'm not sure." "Wait, you've… you've put stuff up your ex's ass?" He asked, his face even redder than before if it was even possible. "Yeah, it's called pegging. It's pretty popular. Of course some guys just like a finger or two, but you might like it. Plus, you said your d**k is pretty raw. I could only imagine that hurts worse." "I know what it's called…" Arin rubbed the back of his neck and cleared his throat. "Since you've done it before, Would you be willing to help me take care of this? Please? I'm pretty desperate." Arin pointed down at his bulge, and I bobbed my head slowly. "Sure. Not to mention my ex's business, but I've usually gotten them to c*m pretty quick and intensely with prostate stimulation. Do you have any lube?" I could watch Arin's eyes dart to the drawer next to him. "Yeah," Arin reached out his hand and opened up this drawer. He pulled out a small bottle of KY lube and held it up. "Is this enough?" He looked from the bottle to me, and I nodded. I walked up to Arin and took the bottle from him. "Let's move you to the couch for more comfort." I smiled and placed the lube bottle in my shirt, between my breasts. It was the easiest way to heat it up. "You promise you won't tell anyone?" "Arin, I promise. I just want to help you. We can forget it even happened when it's over." Arin smiled back at me, and I watched as he made his way to the couch near the window. Luckily we were on the 3rd floor. No one would be able to see anything. I walked over to Arin and sat next to him. "How do you want me to handle this?" I respect boundaries, so if Arin wanted only a single finger without affection, I would give it to him. "I don't know." Arin looked down at his lap and cleared his throat. "I don't know... if I'm being honest, I have a few self-esteem issues. If you find me attractive, then you can do what you like. You're way too pretty to be even thinking about doing this." I touched my cheeks, and I looked down at my lap as well. "We can do what feels right in the moment." I offered. In response to his nod, I leaned in to kiss his cheek. "You're in good hands. I promise." I scooted towards the edge of the couch and turned my body to Arin. "Lay down. It's up to you if you want to lay on your stomach or back." "Which is easier for you?" I thought about it for a moment as Arin laid down. His breath was uneven, and I laid my hand on his. "Will it make you feel better if you can see me?" Arin's fingers undid his pants and slowly pushed them down. I helped take them off and folded them before I placed them under the couch. "Actually I think it'll make me feel weird." Arin turned on his stomach, I grabbed a secondary pillow to put under Arin's hips. I rubbed my hand against the curve of Arin's behind. I could feel him tense under my hand and I moved my hand up to his back. "Try to relax," I whispered softly. I laced my fingers in his hair and gently ran my fingers through his locks. Arin closed his eyes and nodded. "I'm going to move my hands to your boxers, okay?" Arin nodded, and I grabbed the waistband of his boxers. I slowly pulled them down and rubbed the pale, white skin under my hands. I messaged his cheeks in my hands before I slowly pushed them apart. Arin whined and shuddered. "f**k, this feels so weird," Arin commented, his voice much softer and calm than before. I reached my hand into my shirt and opened the lube bottle. I squirted some on my fingers and rubbed it against my skin to warm it up further. I took my free hand and rubbed Arin's back as I slid my index finger inside of him. "Okay, stop. No, I don't like this." Arin freaked out, and I tried my best to stay still to not hurt him. "Arin, hold still. I don't want to hurt you." I tried to soothe him before I removed my finger. If he clenched too hard it would hurt to pull it out. I turned my hand a bit before Arin moaned out loud. "Oh f**k. Wait." Arin took a moment to steady his breathing before he turned to look at me. "That felt good, do it again." "Are you sure?" I watched as Arin nodded slowly and closed his eyes. "I trust you." I smiled and slowly pulled out my finger before I slid it back in. I made sure the tip of my finger pressed against his prostate. "Ahh~" I continued to massage the small bundle of nerves before I pulled back. The man in front of me moaned lewdly, his hips pushed back against my hand as I started to remove my finger. "Oh f**k. That feels really f*****g good." Arin shoved his face into the couch under him, and I couldn't help but want to give him more. My finger curled as I thrust in and out at a steady pace. With rhythm, Arin rocked back against my finger. He moaned out into the air, his mouth slightly open. "Yes, Oh s**t. Mmmhp~" slowly and gently I slipped a second finger inside and bit my lip while Arin gasped loudly. I could see the goosebumps on his skin as he shuddered. I plunged in, knuckles deep into Arin's entrance. His moans made me feral. I would have loved nothing more than to have him wrap around my strap-on, but perhaps that was something for later. "Miranda." A soft whine pierced the air, and I smirked, nothing better than having a grown man drool over my fingers. "More?" I whispered to Arin. I pressed my fingers firmly against his walls as I squeezed his prostate. "Harder." He threw his head back as hair stuck to his forehead and cheeks. I nodded and with more force, began to finger Arin faster and with more intensity. "Oh my God." I had to bite back a smile. Arin always said God should be a woman, and I guess his is. Arin rubbed his hips against the pillow as my index and middle fingers twirled inside of his heat. His walls contracted around me as he moaned like a cheap w***e. Each moan was more loud and whiny than the one before. He had to be close. I knew the muscle spasms too well. He was about to c*m, and it was going to be hard. I began to scissor him to help open him open up more. Without thinking, I let a glob of saliva drop from my mouth into his gaping hole. Arin shuddered once more, his pants and moans almost indistinguishable. "So hot," Arin muttered. He dropped his head onto the couch, and I watched as his eyes rolled to the back of his head. "I'm gonna- I'm gonna-" without another word, Arin's hips snapped forwards and his walls tightened around me so hard that I couldn't move my fingers out of him without almost ripping them out. "Ahhhhh~" Soon Arin's hips loosened, and he dropped down onto the couch. His breathing was erratic as I slowly pulled my fingers out of him. I walked up to use the restroom in Arin's office. I washed my hands twice, always being a stickler for cleanliness and I grabbed the pack of moist toilets to help clean Arin up. I walked back out into the office to see Arin with his eyes closed and pants around his ankles. He must have really enjoyed himself. "Arin?" I walked up to him and squatted down next to him. Arin opened his eyes and gave a sheepish smile. "Thank you, that felt really good. I feel a lot better." He whispered, I brushed the hair out of his face and nodded. "I'm glad you feel better. Here let me help clean you up." I handed Arin some wipes and helped him sit up. I grabbed the pillow covered in Arin's semen and looked back at him. "Do you just want new pillows?" Arin nodded silently, and I made a mental note to throw out the pillow at the end of the day so it could be tossed in the dumpster with no one noticing. I placed the used toilets and pillow into a garbage bag and placed it under my desk as I walked out. I sat down at my computer, ready to get back to work. I wiggled my mouse as Dan walked up to me. "Hey, thanks for the donuts. Is Arin in his office?" "Yep! He's in a pretty good mood today so, don't ruin it." I smiled. Dan laughed off my joke as he walked towards Arin's office door. If only Dan knew how much work it was to get him in that good mood.