My Boss

my first story so if its bad im sorry. This just happened so I had to write about it. My 40s or so boss drops many hints over a course of a few months until...

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  • 18 Min Read

I’m 19 and working as a CNA while I’m in college. The company I’ve been at for about a year and a half just merged with another one. In real-world terms, we just got a whole lot cheaper so they can pay one dude a bunch of fucking money. With this “merge” also came a new executive director—our previous one is moving up in the company. The old executive never really showed his face on the floor where we care for the residents. Our new one, who we’ll call Matt, comes around a lot.

The first time I noticed something a little flirty was when I was charting at the computer. From where I sit, I can see whoever comes onto the floor just by looking to the left. He was with someone else, giving a new hire a tour. I focused on my charting, but I heard him and the other girl walking up to me. Then I felt his strong hands grab me high up on my shoulders, kinda by my neck. I remember him saying something like, “This is Brett. If you’re lucky, you’ll get to work with him.” The only thing that tipped me off was that he was almost choking me and he held on for wayyyyy too long.

For reference, this man is fucking fine. I’m exactly six feet tall, and he’s about a couple inches taller than me. Bald. He has a big nose that fits his face perfectly, crow’s feet that make me wonder how many different people he’s gotten his dick into, and a full beard. The only imperfection I could spot was one of his front teeth that comes out slightly more than the other. But it just made him hotter.

Our second encounter that I deemed suspicious was about a week later. He came down to my floor and I was just walking back from answering a call light. This time he reached his hand out like he was gonna dap me up. But instead he went for a bro hug of sorts and said, “Hey Brett, how’s everyone doing?” During this “bro hug,” he pulled me into him and put his arm around me for a quick second, his hand placed on my lower back while mine was on his upper back.

He started to let go as I responded with, “It’s been good so far, but the morning was rough.” Then he said, “Have you seen ***** (my lead coworker)?” I told him where she was, and that was basically it. I noticed how he keeps touching me in sensual places for sensual amounts of time. It was hard to contain the boner in my scrubs.

Ever since the second time this happened, I remember wanting more and more. It was the type of horny where just a nudge of a thought would get me hard to where I was leaking in my fucking underwear at work.

The next couple of encounters were just vocal things. The first one was around my other coworkers. One of the other CNAs was talking with him just as I finished bringing one of my more difficult ladies to the bathroom—the one she had just tried to toilet. I work on the dementia floor that is basically all women. I walk up to them and they see me. My coworker says, “Christ, it bothers me that they just listen to you so well.”

Matt responds with, “They just can’t say no to a stud like Brett.” He looked me in the eyes while he said it. And fuck. The way he was looking at me and smiling—he could have folded me like a damn pretzel right then and there and I would have let him.

At this point in my mind, I didn’t know if he was trying to get at something or not. But my hopes soon came true. The next time he said something that gives me jerk-off fuel was the next day after that. It was a Wednesday. On Wednesdays the company has “team huddles.” Pretty fucking stupid if you ask me, but they basically have everyone come down on the floor—kitchen staff, nurses, sales, a bunch of people. Why their meeting place is the memory care unit, I have no clue. Anyway, he is always the first one down. It is during our downtime, right after breakfast, so we are usually charting.

This time all three of my coworkers were at the desk with me. One a girl my age, one in her late forties. He did the same thing and made me even start to question. He grabbed my traps and kinda dug his thumbs in and went in a circle and asked, “Jeez, Brettmeister, you stressed or you been working out?”

“Definitely gonna take that one as a compliment and go with working out,” I said.

He chuckled deeply as he started to walk away and said, “Well good, I can feel it.” And he winked. HE FUCKIN’ WINKED.

At this point I am entering obsession with this man and I am dying to know what he looks like naked. Trust me, I searched Facebook and Instagram and couldn’t even find a shirtless pic.

Now I am bi and don’t feel the need to flaunt it or tell every person that I see, so I ask my coworkers if that was kinda weird. They both said yeah and went on about how he always touches me. Then the girl my age says, “Well you guys are dudes and you are the only guy on dayshift.”

Anyway, this next part is when I really was like, damn, this is probably gonna happen.

So I am very vocal about how I use the nursing home’s gym because it’s free, always empty, and has way too nice of equipment for a nursing home. I have even told my scheduling team that I am usually in there at either 3:30 right after my shift or 8 p.m. if I’ve got a shitload of homework. I’ve also mentioned this to Matt. When I did, he told me he was gonna have to check it out. He said he had been a little busy with adjusting to his new job and new town so he hasn’t gotten a gym membership. But this conversation was way before anything weird happened.

But he must have remembered, because not long after my dick started pining for him, I saw his fine ass on the rower in the gym at about 8:09 p.m. Now I was so fucking scared because it was just him and me in the gym. He had headphones on, was wearing a loose grey wife-beater with shorts that were a little tight. He was all the way to the left where the cardio stuff was, and I walked all the way to the other side where the racks and machines were. I just started my workout like normal. It was chest day.

I had finished a couple sets of incline DB and cable flys when I peeked at him. He looked at me and smiled. Then he put the rowing bar down and got up. He walked over to the cable machine and held up his knuckles with one hand and leaned his arm up high against the cable machine. I could smell him and I started to get a little chubbed. As he went for the knuckles he said, “Brett! Getting those gains?”

I looked him up and down slightly first, just to see if he would catch it. Then I gave him knuckles and said, “Hell yeah, chest day. How about you?”

I think he caught my eyes because he immediately cupped one of my pecs, shook it, and squeezed it. I watched him reach for it too, then looked at him while he touched me.

“Nice pump, man. I was just warming up for back and bi.” Then he said, “A nice built young man like you has got to have a girlfriend.”

“Nah, just not looking for anything like that right now, you know?” While I said the word “looking,” I looked down at his bulge.

“I get you. You got all the time in the world though—you’re young. I’ll let you get back to your workout. No one likes to be bugged by their boss off company time,” he said while laughing.

“All good, man. You can bug me anytime you like, Matt.”

He paused for a moment and then put his headphones back on and went back to his workout. I did the same. The entire time we were lifting I could feel his eyes on me as I moved through my sets. And I’m sure—well, I know now—that his eyes were on me too.

I finished up with abs. I was walking to the corner where I leave my stuff. Matt was on the rowing machine—not the cardio one. I had to walk by him to get my stuff. While I was walking he looked up at me and freed an ear from his headphones. I said, “Have a good night, Matt.”

“I’ll walk out with you. I’m too gassed to do anything more. I must be getting old.”

My heart started racing because I go shower after I workout so I can just go home and go to bed. My thoughts started racing and I got so excited, so I started walking faster.

“I guess I’ll run with you then,” he said while looking over at me and smiling.

I just laughed. We got to the locker room door. I scanned us in. Now this is the moment of truth. The way the locker room is set up, it goes left and right. Lockers and showers on both sides. I just had to hope that he put his stuff in the locker on the right because that’s where my stuff was. He did. We both started walking towards the right.

This is when I started to move fast. I was digging for my towel and soap in my bag. He seemed to be digging for something as well. I pulled out my towel and my soap bag before he did. I wanted to go to the showers first to see if he was even gonna shower and if he was gonna stay on the side we were on or if he would go on the other side. All of the showers have a dry bench area that is also behind the curtain to change and undress.

I knew he was behind me still at his locker. I didn’t dare look to see if he was changing or not. I pulled the curtain just enough so it would seem like I closed it but just enough so he could see what I was about to do. I faced opposite from where he was at and pulled off my shirt and slid down my shorts. I was wearing a jock so my hairless hole was on full display. I then bent over with just my jock on to take off my socks. Then I wrapped my towel around me quick and walked towards the shower.

I looked back at him just in time to see him walking towards the shower next to mine in a towel. My heart is racing at this point. I am naked next to my DILF of a fucking boss. Of course I was boned. I mean, it ain’t hard to get a boner at 19. I was starting to wonder if this was just a bro kinda thing or if he was into it.

We both showered for about five minutes. Then I started to open my soap and it made a click sound.

“Brett, do you have any extra soap?”

My dick jumped hearing his voice while knowing he was naked. “Yeah,” I replied. But these nursing home showers weren’t like a regular locker room. They were each their individual stall with full walls and a curtain. There was no way I could have slid it under or tossed it over.

Some awkward time went by while we both decided how to handle this. Then he said, “Alright, I’ll just come grab it quick.”

I started to think rationally at this point—why I’m rational after I already flashed my asshole to him, no idea. I said, “I’m naked though.”

“So am I.”

“Yeah but I’m like extra naked.”

He laughed and it echoed through the locker room. Then he said, “What the hell does that mean?”

“Good lord, I can’t believe I am about to tell my boss that I have a boner.”

He starts cracking up. “Get hard after working out?” he asked.

I had my moment of rationality and now I decided to be bold. I said, “Yeah, among other things.”

He went quiet for like a full minute. I started to panic. Really bad. Then he said, “I’m gonna come grab the soap.”

I heard him walk out from under the water and open his curtain. Then I heard him open my curtain. That’s when I saw him. He had just the right amount of hair everywhere. Hairy chest but not too much to overdo it. A happy trail that made me one step closer to cumming. Then I saw his dick. It was not soft but not fully erect either. The shade of red was the most pretty shade of red I had ever seen on a dick. His scar from circumcision was larger than most. He had a nice bush but his dick and balls and like a half an inch around the base was hairless. If I had to guess, he was about six inches and that shit was still hanging down so he had a ways to go.

I had the soap in my hand. All he said was, “Holy shit, you have a big dick.” I’m 8 inches hard and thick. My best friend in high school had two nicknames for me: Popcan ’cause my dick was thick and Hook ’cause it hooked upward.

I said, “Thanks, you too,” I laughed and continued with, “This is so fucking weird.” He laughed too, took the soap, and said thanks and went back. He took a few minutes before he returned my soap. He came back and he was fully hard. His dick stuck straight out.

Then he said, “You know it was pretty easy to tell it was you on Grindr considering you take nudes in this locker room.”

I was so confused. Then it clicked for me. He is married. He has kids. He probably has a blank profile. He didn’t even let me reply before he entered my shower and pulled me into him by my neck and stuck his tongue down my throat. Our dicks touching while we moved with the makeout. Then he pushed me away and asked, “Do you want this?”

“Fuck yes,” I smiled.

“Good.”

Then he left the shower and I heard a key lock and I got really bummed out. I thought he had somehow heard something I didn’t and someone was coming into the locker room. Then he came back and said, “The door is locked.” That was all I needed to hear.

I dropped to my knees so fast. I went for his gooch to take a big whiff. He moaned. Loud. I licked from his taint all the way to the tip and deepthroated his dick. His hands found my head and he pushed and fucked my throat like a fleshlight for five solid minutes. I was close to throwing up when he pulled me off.

“Fuck, you can take a dick, can’t you?” he said from above while looking at me on my knees.

“What’s off limits?” I wanted to know where this was going.

“I’m game for anything, stud,” as he wiped some slime off my chin and put his fingers in my mouth.

I stood up and grabbed his dick with my left hand and the back of his neck with my other. I pulled him in and started kissing him again. Then my hand reached down to his ass. “Anything as in I get to fuck you too?” I asked.

“Not this time,” he said.

I responded swiftly with, “There will be a next time?”

“Let’s get through this first, yeah?”

“Fuck yeah. I’ve been wanting that dick since the first time you touched me.”

“You caught all that?”

“Yes. Now will you fuck me already?”

And with that he grabbed my hand and brought me to the dry area with the bench outside the shower. He made me sit. Then he dropped to his knees and started to push my chest down so I laid down on the bench. He was looking me in the eyes the entire time. Once I was flat he grabbed my feet and pulled them apart and pushed them up.

“Such a nice fucking hole.” It came out muffled because as he said that he started to eat my ass out. I felt his beard start scratching and I started moaning. I placed my legs on his shoulders. At first he was just lapping me everywhere, getting me wet. Then I felt his tongue go in my hole. His tongue must have been stronger than his biceps or something because it was the most pressure I had ever felt from getting head.

“Fuckkkk Matt,” I moaned as he was jabbing his tongue in and out of my hole. We stayed like this for a while. I think eating ass might be one of his favorite things to do. His tongue was doing so much work that I hardly realized when he slipped a finger in along with his tongue. I reached for my cock and he swatted my hand away.

He pulls his face out of my hole and grunts, “I’ll do that too… later.”

He went back to fingering and eating me.

“Matt?”

“Yes?”

“I know you said I can’t fuck you yet but can I eat you out? Can’t pass up a thick dad butt.”

He faltered for a moment when I said the word “dad.” It was quickly replaced with a new profound look of horny. He dropped my legs to the floor and removed his face from my ass. I started to get up because I just figured we would switch places. Then he pushed my chest down and duck-walked over me. He stopped once he was standing above my face. That view is still in my mind. At first he lowered just his balls and dragged them across my face. I remember thinking, Holy shit, my boss is fucking teabagging me right now. Then he put his hands above my head on the bench and contorted his body enough so his dick was right in front of my mouth. I started sucking. He got lost in me sucking and his thrusts. With my hands I reached up and started to rub his hole. I had to remind him of what I asked. He jolted. He caught my drift and started to pull his dick out of my throat. As soon as I could speak I asked, “Have you had a dick inside you?”

“No but my wife loves to play with my butt.”

Pretty sure with those words I leaked a copious amount of precum.

“Okay so let me then.”

Then he started to sit on my face.

I spread apart his muscular cheeks. His ass was hairy all over but around his hole was hairless.

He started moaning a lot more than when I was sucking his dick. Now it’s making sense why he ate my ass for so long. He knows how good it feels and he likes it. Then he actually started to sit on me. It was so intoxicating feeling his ass envelop my face. Then I started to panic because I couldn’t breathe anymore. I tapped his butt but he didn’t budge. Then I slapped his ass and he stood up fast. I gasped and looked at him, trying to smile but I was still taking in air. I could see in his eyes that he was worried. He made me sit up and gave me a few seconds before he sat on the bench and picked me up. We are both tall so I had to like climb on him instead of him lifting me all the way.

I was on his lap and I could feel his cock nestled between my cheeks. He kissed me really slow and said, “Are you okay? I’m so sorry.”

“Don’t be. I’m fine. I asked for it to be fair.”

“Yeah but I got carried away.”

“It’s okay really. I think I’m ready for you to fuck me though.”

“I’m not.”

Then he moved so I was off of him again. Then he laid on the bench.

“Your turn.”

I got up and went to go hover on his face carefully not to do what he did. Then he grabbed my hips and pulled me into his face. He started eating me again but this time he was rubbing his big nose along my hole. I was going crazy. I thought I was going to cum then. Once I was sat on his face how he wanted me, he took his hands and reached behind his dick and was trying to find my dick. I grabbed his hands and guided him towards it. He began double-fisting my cock while eating me and fucking me with his nose. I was moaning like a little bitch and he hadn’t even fucked me yet. I got close to cumming and I was going to get up to get away from him but he pulled me back down. I endured this terrible mental game of not letting this end yet for a few more minutes before he pushed me off. His face was red.

“What position is easy for you to take dick?” he asked as he spat on his cock.

“Genuinely you can pry me open however you want.”

“I want to look at you.”

So we resumed the position of me straddling him when he almost suffocated me with his ass. This time he started kissing me much more aggressively.

“Ready?” he asked.

“Please fuck me, Matt.”

I felt him push me up a little with his legs and grab his dick with his other hand. Once it was lined up with my hole I grabbed the side of the bench to raise myself a bit. Then I started sinking onto his fuckstick. It felt so fucking good. Felt like I just did a couple lines. He was grunting and moaning and nuzzling my neck the whole time I was taking his dick. Once it was all the way in he started to move but I stopped him.

“You are fucking huge. Just give me like thirty seconds.”

“Okay. I think I’m good.”

That was all he needed to hear. He removed his arms from around me and placed his hands on my lower back. He pushed my chest so I was leaning away from him but he was holding me up. Then he started to move his hips. Slowly at first. My dick starts leaking a lot. Then he starts humping up and down and I can feel his dick almost exit my hole each time but slam right back in. Each time he hit my prostate I moaned and almost came. He started going faster and he kept pulling me in to kiss and pushing me away to thrust. Every movement was adding to the pleasure between us.

“Fuck fuck fuck Brett,” he kept moaning and saying my name over and over. I couldn’t tell if he was close to cumming or not but I hoped he would want to fuck me doggy before this was done.

I was getting more and more turned on as this happened. It’s a little hazy but I think I asked him to spit in my mouth and he did. And he liked it.

After a while he laid me down and was fucking me missionary on the bench. I kept looking at his face and the part of his dick I could see go in and out of me.

“Brett I’m close. Can I come in you?”

“If we go back to me riding you I could probably cum hands-free from my dick slapping between us.”

In one go he picked me up and sat up so I was on him again. He jackhammered me for another couple minutes until I could see in his face he was going to cum any second.

“I’m really fuckin’ close.”

“You better grab my fuckin’ dick, Matt.”

He started stroking it. His rough hands on my dick and his fat cock in my ass. He grunted loudly and I could feel his hot sperm in my ass. I came with him and sprayed cum everywhere—all between us, up on his face and in his beard. He collapsed on me. This bench is way too small for the both of us but I loved the feeling of his weight on top of me so I didn’t move until he did.

He got up and I could hear the goopy sounds of my cum as he unstuck himself from me and pulled out. As soon as he did he grabbed a dollop of his cum from my hole and gave me a taste.

He started laughing. “Another shower then.”

We both went in the same shower and used my soap and soaped each other up.

As we got our things to go he said, “Brett…”

“I know, I know. This stays between us.”

And that was last night.

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