I had finally returned to the city after living in the countryside for a few years. I had come to the small city for college after high school and had a few flings with girls, the milf who took my cherry and where I sucked my first cock. I am bi, average build, I think the term would be otter on the account of my beard. During my time away I had come to the city on small trips and would fool around with someone depending on my mood.
Now I was back and I was eager to cross something's off my bucket list (fucket list is what I call it my head.) Apps and some websites had help set up some get togethers, though they seemed to end in disappointments. The guy would be into the hook up till I got there only to become distracted by something else. I would end up fooling around with cocks that never stayed hard, jerk off and leave dishearten. I tried to select men who would provide a good time, trying to avoid those who don't fit what I am looking for.
When it comes to having sex with men it comes down two things for me. Body type and cock. The encounter's I've had were mostly with older men who don't fall into the body type I'm looking for, I was horny and tried of being picky. I love twinks and have always wanted to be with on. With cock's the bigger the better. Something to make me gag on when sucking or getting fucked. I'm usually the bottom when having sex with men, I love the feeling of being handled by someone with a good size cock and knows how to use. This being said I've always want to top someone, to be the person driving their cock in that perfect ass as they moan face down in the pillow.
I had taken a job with a janitorial company which left me open during the day but the people whom I sought were out looking while I was at work. And getting off late did not leave much options either. Porn, my fleshlight with the ass opening, prostate massager, dildo and two different size butt plugs would help satisfy the urges and thoughts. Few months into the job a higher position opened up and I was recommended for the job and eventually got it. Now I was in charge of some buildings and the cleaning staff. Part of my task while learning my new role was training my eventual replacements. I kept myself distant from the ones who came in trying to fit in my role as boss. In the biggest job I covered I had asked they find someone like me to fill it.
Someone tall and not afraid to have to life heavy filled bags of trash into the dumpster. I was told the person replacing me was named Dan and he was a college freshman with some experience in cleaning. To say he was what I was expecting for the job fell short. I am 6 ft tall where he was 5'6 at the best. Where I am average build with strength from years of splitting wood by hand he was a skinny little thing. Almost what I was in high school but skinner. He was a twink, but a little skinny for my taste, he wore his hair in that Bieber hair style.
The first two days I meet with him I kept my mind on work, and making sure he was doing everything like showed him. It was the third time we meet where my troubles slowly began. The first two day's I trained him we made brief small talk as I should him the job and walked him through it the second day. I made small observations about him, his smooth face, I don't think he could grow a beard or he just liked to keep his face clean shaven. It was a warm and inviting face with kind of a girlish look. His arms were skinny and hairless, his hand small and feminine with long fingers. Dan could have dressed up as a sissy boy or t-girl and I, along with many others, would have snatched him up.
The third day I was shadowing him, making sure he got everything. The job was only three days a week I had many buildings to drive and check one, so it would have to be something enticing to break my concentration. I saw it first but thought nothing of it when he squatted down to get some loose papers that had missed the garbage. The second time I saw it was when he was checking to make sure he dusted behind the something. The thinness of his legs leading to his ass which he really didn't have, the smoothness of his back where his t-shirt rode up to that head of hair. My mind began to wonder what he would look like naked as I plowed his ass.
I tried to push these thoughts from my mind, and focused on his work. Finishing work my mind wandered over dirty thoughts about him as I drove home. Eating quickly I pulled up some of my favorite twink porn I had downloaded over the years and furiously jerked off. I didn't last long I was super horny form the ride home. Cleaning myself up I thought about Dan. How would I even broach this subject to him. If we weren't working together I might be more forthcoming, I wished I had meet him on the hookup apps for it would make this easier. Even in this age of tolerance, I felt he would push back if I ask him if he was gay or even bi.
A quick look at social media sites didn't help me either. Work took me away from him for a few days as I had other areas to work on. Finally I had a chance to check up on him without him knowing I was coming. My heart skipped a beat as I drove to the building, my mind filling with impure thoughts. The one which stiffened my cock as it played before me was my favorite. It was Dan on my bed, he clutched them as his face lay on it side. His ass was in the air before me, begging me to enjoy the tightness of his hole. The paleness of his skin was warm as I ran my hands across the smoothness. He sighed with pleasure before begging me to fuck him.
Spreading his checks I run my cock up and down his crack, grabbing the bottle of lube a dribble it down his crack and on my cock. Covering my fingers I insert them in him, he moans in happiness as I work his hole. Pulling out he whimpers as he wants the feeling of emptiness to go away. Stroking my cock to spread the lube, I pull the foreskin back. I feel the rush of excitement as I guide the tip to the entrance to heaven. Gently I push in letting as he adjust to my two inches of girth, slowly we go till all seven inches are in.
Bending down I whisper in his ear, "Do you love my cock inside your ass."
"Yes," he replies, "fuck me gently."
I oblige him slowly moving in and out waiting for him to tell me when to change the pace for I know he likes a good pounding on days when he doesn't want to make love. Our hips bump together as he moans into the pillow, his hands clenching and unclenching. He becomes looser and I know what is come.
"Fuck me Tim," he says. "Fuck my ass."
With a grin I pick up the pace and begin to pound his ass. My hands move from cupping his checks, to grabbing his hips in oder to drill him deeper. He gasps as the I fuck his ass, he lifts his head mouth agape. Reaching out with my right hand I grab his head pulling it back. I love how he moans my name as I slam in and out of him.
Shaking my head I try to get into my work mode as I climb from the car. My pulse was racing and my checks were flushed from these thoughts. I did not seek him out right away, I checked his work while trying to make myself feel calm and collected. He was startled to see me when I finally found him, granted he as listening to music and I have a bad habit of sneaking up on people without trying to do. Explaining why I was there I asked if he had any questions about the job or problems remember anything. Dan had a couple and wanted me to look at somethings, I obliged him. As we walked and talked I continued my observations recording them in my mind in order to expand my fantasies when I got home after work.
One of the things I tried to pay keen attention to his face while trying to get caught for staring. I was still nervous about asking him and hoped I could broach the subject some other way and not on company time. Answering his questions, I let him go back to his work as I double checked somethings before for leaving to finish my work for the night.
Returning home that night I made dinner as was my custom before jumping on my computer to catch up on things. Finally I was ready to jerk off before I went to bed. Deciding to make it special I got one of my but plugs out a lubed it up. Pleasure ran through me as it stretched my hole before resting next to my prostate. Opening some pov porn of sexy female porn stars I stroked myself thinking about Dan.
His small mouth sliding up and my shaft, occasionally deep throating me as the head of my cock blocked his airways. He pulled off gasping for air while he jerked me off with his small hand. The look of joy in his brown eyes as he jumped back on my spit covered dick. I reached out placing my hand on his head guiding him. He looks so cute on his knees, his skinny body screaming for me to fuck him as he jerks himself off. His cock in my mind isn't big, it's similar to mine seven inches long and two around. The only difference is he is cut, but I have no care about that. As I guide him I hold him in place as he takes as much as he can into his throat I moan in pleasure.
Dan is getting better at this, soon he will be able to swallow me hole. I look forward to the day his nose is able to touch my trimmed pubic hair. My balls being to tighten, I tell him I about to come. Slowly he backs offs letting my dick pop from his mouth like a lollipop, Dan holds my gaze as he does this. I almost cum right there.
I want you to come on my face he says. Jerking my cock he leans down to lick and suck my balls urging me to cum faster so he can have his reward. Moaning at the eagerness of this young man I cry out that I can't hold back. Dan shoves himself backward and aims my cock at his face. He sits there mouth open, his tongue out and eye's shut. I feel like I'm in heaven as the first spirt of my load shoots out and lands on his face. More gooey strands follow. I feel light headed ready to sit down, Dan works my cock making sure every drop gets out before putting me back in his mouth to clean me off.
Increase my speed as this dream comes to an end. My seed spews into my cum rag, I am spent. Leaning back in my chair I feel my cock go flaccid as I feel the guilt flow over me.
A month after starting my new position I transferred to a different part of the company, I found this acceptable as I felt my abilities were being wasted checking on others works. The company agreed with me on this. It took a few days to catch everyone up on me shifting positions. Dan was one of the last to find out as he had been off for a few days. When I finally say him I had to fight the urge to not just blurt out how I felt. In the back of my head I was already thinking about reaching out once I was in my new job, as I would no longer be his boss.
The first week of the new job I took all my free time to relax, my old position had left me stressed. I didn't do much, lounged about when I wasn't at work taking care of a few small things. I had plan to reach out to some people for a hookup but decided against it, I just want to be alone. The next week I was scrolling through one of the apps on my phone when a message appeared. I took my time getting to it as I was looking at the faces of those on and offline while reading the profiles of those who perked my interest. Looking at the message I saw it was a person who had no profile pic. I'll admit I always loathed those for it was to much mystery for me to handle. Taping the blank image I looked at the profile. There wasn't much there. A simple handle, and a short blurb about a shy twink looking for someone older who wanted someone with a dad bod. There was a basic height, hair color, and position. This one was both top and bottom.
Why me I thought going back to the message screen. This twink could have anyone he wants. I had never considered myself to have a dad body since I wasn't a dad. I'll admit I do have a small paunch from my love of beer. I could read the message before I even opened it all it said was hi. Looking at my phone I debated about responding. This could be what I am really looking for, and it could be some asshole just yanking my chain. If I don't respond and he never gets tries to message me again will I be caught up on the what could of been?
Fuck it, I thought as I typed back.
Hi, how are you?
Good.
He replied.
You?
Alright, just seeing whats out there tonight.
