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.
He sent back. Cool. What are you looking for?
Whatever comes my way. Would like to get sucked and fuck someone. Willing to reciprocate.
I waited anxiously for a reply.
Me to. Can you host?
Having my own place I would be fine as long as we didn't get to loud.
Yes. I replied. Do you have pics. He would of seen mine, it was a standard headshot and one of me standing sideways in the mirror with my shirt on.
The first picture I got was of him lying down the camera looking over his shoulder at his naked body. I could see his ass, a small round bubble of pure joy. Next pic was of his dick looking down at it as it stood erect. I was salivating at the sight of these. Quickly sent him a pic of my cock from the I had in folder of it rock hard from the side.
Love your ass, you are so sexy. I sent him.
Thanks. He replied. I want to taste your cock.
I was getting ready to ask him if he need directions or a ride when he sent his final picture. It was a head shot.
My heart skipped a beat as I stared at it. Holy Shit! Its Dan! My mouth went dry as I tried to think of what to say to him.
Hi tim, I've been wanting to do this since I caught you checking me out.
I'll admit I was hoping you thought I was watching your work and not your body.
Do you still want to do this? He asked. Was he nervous now that I knew who it was.
I quickly typed back.
Fuck yes I want to. Do you need a ride or directions?
My folks need the car for the weekend. I'll tell them I'm going over to a buddies to work on a group project for my history course.
You can pick me up at the end of my block. The directions soon followed.
Ok. I will be leaving shortly.
My heart was pounding in my ears as I got my shoes on and grabbed the keys to my car. Getting in I took some deep breaths to calm my nerves. Opening the garage door I blessed the fact that it was still early in the night but late enough for my neighbors to be out. Turning the radio on tuned in the local heavy metal/rock station help keep me from cumming in my pants. My cock was fighting against my clothes; I could feel the precum leaking out as I drove.
After ten minutes of driving I pulled up on his street. My mind tumbled over the questions I wanted to ask as he opened the door.
"Hi," I said glancing at Dan as he climbed in.
He set a small bag on his lap. "Hi, just some change of clothes. Since we have the whole weekend to ourselves."
My mouth was dry as I turned the car around and headed for my apartment. I turned the radio down, so we could talk but I had lost my voice.
"Are you nervous." He asked.
"Ye..Yes." I stammered.
Dan smiled. "Me too."
"Do you have any experience in this?"
"Some, I dated a few guys in high school. And I've had sex with some guys in college."
That made sense to me. College was the place where I to had experienced my first gay sex. My cock was fighting to break free as I drove us home. I glanced at him again, that profile of a body I had long engrained into memory.
"How long did you know it was me?"
Dan looked up from his phone, "I only joined recently, I shouldn't of been surprised to see you on there. You never really did speak about much besides work."
"Sorry about that, it takes me sometime to warm up to people, only a handful are special enough for me to click with right away." I said pulling into the garage.
"It's okay, I wasn't sure how you would respond when you figure it out it was me. I hoped for the best since you were always checking me out at work."
We got out the car and entered my apartment. I apologized for how it looked. While I worked for a cleaning company it took me a longer time to clean my apartment than the jobs I did. Giving him a quick tour, we may our way to the bedroom. Dan set his bag down by the bed and sat down on it. I stood there watching him, wondering how far this thing would go. Taking a seat on a chair next to my computer I faced him.
"Before we go anywhere with this I just need to know how far do you want to go?"
"Do you mean like sex stuff."
I sighed wanting to get this over with and get straight to sex. "I mean are you just looking for one time thing or a boyfriend?"
"I'm not really sure," Dan replied. "Right now I think I want this to be more than a one time thing, but I'm not really looking for a boy friend."
"So your looking for more of fuck buddies."
He smiled. "Yeah. Anything else?" I could tell he was as anxious as I was.
"Do you want to be top or bottom."
"I want to suck your cock and have you fuck me in the ass." He said taking off his shirt.
Standing up I watched as he unbuckled his belt and started to unzip his jeans. Shit, we have all weekend to do what ever we want, I thought as I removed my shirt and kicked off my shoes. Removing his shoes he slid his pants down to the floor, leaving him with only his boxers. His cock was tenting fighting against the fabric. I drank in the site of his body.
He was skinny as I thought he was, though I couldn't see his ribs. He's probably light enough I could hold him as we try to fuck. Reaching out I took his hand and gently pulled him from the bed. Dan stood there looking at me wondering what to do next. I wasn't sure myself. His fingers reached out and touched me, running his hands over my chest he meet my gaze. I want to pull him in an kiss him, but I had only done that with women and always just had slam bam thank you sir sex with the guys I had been with. Dan seemed to read my mind leaning in he kissed me on the lips, I hesitated before returning it. Our mouths opened as our tongues intertwined for the first time.
I reached behind him and pulled his body into mine, the warm and feel of his smooth skin melted my anxiety. Running my hands over his back I made my way down to his boxers. My hands found what they sought, the checks of his butt. Giving them a squeeze Dan pushed himself into me as we broke our kiss. He took a step back Giving me a good look at his body, taking the waistband of his boxer's in his fingers he slowly pushed them down. He must of smiled when I saw his cock pop out of its cage. Letting them fall to the floor Dan stepped out of them and leaned into me once more.
The hardness of his cock pressed against my jeans as we resumed our kiss. My left had found the bareness of his ass as I fondled him. I brought my right hand around and pushed it in between us as I sought his cock. The feel of the warmth radiating from it brought me pleasure as I stroked him. Dan moaned into my mouth. My dreams were slowly starting to come true.
Dan broke the kiss again looked at me with smile. "I need to see your cock."
"You said you wanted to suck my cock." I said still slowly stroking his, as I to wanted to suck on this lovely dick.
"That too," he said his hands reaching for my button on my jeans.
I placed my hands on his shoulders and gently pushed down. Dan knew what he and I both wanted. He dropped to his knees as he undid the button and the zipper. I helped slid them down to reveal a pair of red boxer briefs. Stepping out of the jeans I stood before him, he looked at me with a mischievous grin as he rubbed my hard cock trough the fabric. His fingers gliding over the wet spot where my precum had soaked through.
"Looks like someone's excited to see me." He said.
I was dying to feel his mouth on my dick.