A gay story: Working Late “James, don’t stay too late, Okay? It’s a Friday and I already feel bad about you coming in today to help me,” Alex said as he walked towards the door leading to the lobby.
“First, coming in wasn’t a big deal. Second, it’s not like I have any real plans tonight.” I said without even looking up from the screen.
Alex looked back at me, leaning the gold frames of his sunglasses down, a look of defeat across his face.
“Ok, fine but seriously don’t spend all night here.” He said as walked out the door.
I turned on the stereo that Alex and I kept in our office, queued up a lo-fi playlist, and got back to work.
I wanted to make sure I put my best effort into our current project. Alex had been with the company a few years and was well known throughout the firm as one of the best project managers. I was new but I wanted to make sure that everyone knew I could pull my own weight after they assigned me to his team.
I reached over to grab my water bottle and picked it up, I realized it was empty. The lightness of the empty bottle being enough to snap me out of the focused state I had been in all afternoon.
Looking over at the clock revealed I had been sitting here working till almost 10.
I turned and looked out the window of the office, taking in the city at night. I could probably put in a few more hours before I headed home.
With it being Friday and having no plans this weekend, I figured I’ll just sleep all weekend so working late wasn’t going to be an issue. I leaned back in my chair and took a deep breath as I prepared to knock these last few hours out.
“Why are you still here?!”
I shot forward almost completely out of my chair as I awoke from what felt like a fairly deep sleep and, while it caught me off guard, I knew exactly who that voice belonged to.
Alex stood at the door of our shared office. The look of disappointment and anger was hard to miss. It wasn’t the first time I had seen that look. Honestly I had seen it a million times and it probably wasn’t going to be the last.
“Hey, I was just going to wrap up some stuff and head home.” I said standing up and stepping from behind the desk as he walked across the office to my desk.
The look on Alex’s face showed he wasn’t buying it.
“James, what time is it?”
“Ummm…..Like 10:30.” I said while looking up to the clock on the bookcase.
12:58AM…….Fuck.
“So I might have fallen asleep at like 10ish….” I said looking up at the clock.
Alex let out a sigh as I tried in my head to remember exactly when I fell asleep.
“So…um…..How did you know I was still here?”I said as I leaned over my desk and started saving and shutting everything down.
Alex walked over to the window and pointed at a large apartment building a few blocks over.
“I can see the office from my balcony. I came home and saw the lights on, so I pulled up sharepoint and saw several files listed you are currently viewing.” He said with a hint of frustration.
I wasn’t sure which was more annoying, the fact he could see the office or the fact he was dedicated enough to check what I was doing.
“Ah….well thanks for coming to check on me. Judging by the clothes I’m guessing you went out tonight?” I asked. Alex had gone through a rough breakup a few months ago and so it was nice to know he was getting back out.
I often joked that he needed to get back out there because at least one of us needed a social life.
“I did. Went out with Mia and Shane but It wasn’t the best night so I called it early.” he said as walked around the office making sure all the lights were off. Mia and Shane were on the marketing team and despite being in their 30’s like Alex and I, they partied like they were in their 20’s. Honestly, I found them annoying but luckily, I was on product design and that meant I didn’t have to interact with marketing that much.
I turned my attention back to Alex watching him frustratedly close up everything for the night. I always thought he was cute and I had a small office crush on him before I was on his team. I sorta stopped thinking about him like that after finding he was in a pretty serious relationship but I still enjoyed at least getting to look at him.
Tonight he was definitely something worth looking at, while at work Alex always dressed in a very professional manner, but here he was wearing a t-shirt that looked almost painted on and jeans that were just as tight. I tried not to look too hard as I took in the way the jeans showed off the shape of his ass and hips and how certain movements caused his shirt to rise up revealing his midriff. The white tee contrasted nicely against the light brown of his skin.
“Ready to go?” Alex asked as I snapped back to reality.
“Yeah….” I grabbed my backpack and tossed it over my shoulder as we walked out of the office and into the lobby near the elevators, all while Alex watched to make sure I didn’t try and slip back into the office.
“Have you had anything to eat?” Alex asked as we waited for the elevator.
“And don’t lie!” He added with a bite.
“Ok, chill. Nah, I kinda just sorta snacked on some stuff earlier.” I said, knowing that I hadn’t even done that.
Alex had a habit of being sort of an office mom, and was always trying to make sure we took care of ourselves. I actually found it cute when he would get all upset about me not eating or drinking enough water. Alex couldn’t have been more than 160 pounds and all of 5 ‘8 vs Me at 6’ 6 and closer to 330, so even when he was trying to be intimidating it was more hilarious than anything.
As the door to the elevator opened, I stepped out and began walking towards the hall to the parking garage.
“And where are you going?!”
“Uh…home?” I said, not sure why that was surprising.
“Nope! We are going to go get you some food first and foremost.” Alex interjected as he grabbed my hand and tried to pull me towards the front door.
I could have easily pulled away and headed home but I decided against it. I didn’t have anything better to do and I really hadn’t had anything to eat and Alex was going to just complain if I didn’t go with him.
“Fine, where are we going?” I tried to sound defeated as I responded, which prompted a look of frustration from Alex as we headed out the front lobby door and onto the street.
“There is a small dinner near my apartment that’s open till 3. We can get you some food and then you can sleep in my guest room. I’ll bring you back tomorrow after breakfast and you can get your car and go home.”
“Wait? When did I say I was spending the night?” I was caught off guard by the fact Alex had said this like I had no say in the matter.
“You live an hour outside the city, it’s a fifteen minute walk from the diner to the office. The way I see it is that you wouldn’t get home till 5ish and you already fell asleep in the office so I know you’re tired and I refuse to let you just walk through the city at night by yourself.”
I could have argued with him about that but I knew it didn’t really matter and I didn’t have anything to lose from it so I guess spending one night wasn’t going to hurt.
Even at 1:30 in the morning, it was a still relatively warm night, one of the advantages of that early August weather. While the streets weren’t empty, they weren’t packed either and you could tell some people thought we were a couple.
It took about 20 min for us to get to the diner, a lot of that time was just spent standing at the crossing waiting for the walk signal.
The diner was nice, it was tucked into the corner of a building about a block from where Alex said his apartment was. I could tell he came here often as the waitress immediately greeted us and led us to a table in the back corner, one she referred to as Alex’s usual spot.
“So you must come here often?” I said as I looked over the menu.
“It’s close by, open late, and they have good desserts” Alex said while tapping on his phone.
Before I could ask another question, the waitress returned and asked what I wanted to drink.
I fought the urge to order a coffee and just ordered a coke. Alex didn’t even say a thing as the waitress walked away. When she returned she had my coke in one hand and a green milkshake in the other.
“I’m guessing that’s your regular?” I asked as I removed the straw from the wrapper.
Alex did the same before taking a deep pull from the straw.
“Mint Chocolate Chip.” He said before returning to his drink.
Alex moved the shake to the side and looked at me.
“I want to apologize…” he said while looking down.
I was confused because I couldn’t understand what he was apologizing for.
“For work. You put in all this extra effort and work yourself to exhaustion. You didn’t even need to be in the office today and yet you came and helped me and then stayed late to work on the project.” Alex said.
“Alex, didn’t I say earlier this wasn’t a problem and it definitely didn’t warrant an apology.”
“But!” Alex tried to interrupt but I motioned for him to stop and pointed to the waitress moving towards us with our plates in her hands.
I hadn’t realized how hungry I had been till Alex pointed out how fast I was eating.
“Hey, Alex…Thanks for making me eat something… I would have just gone home and skipped eating.” I said as I finished my last fry.
“Somebody has to take care of you since you obviously won’t do it yourself.” He said with an almost sarcastic tone.
We spent the next few minutes talking about what I stayed and worked on before I decided to change the topic.
“Hey, so what happened tonight that made you ditch Mia and Shane?”
I figured that it had to have sucked to make him ditch those two but I thought talking about it would have made him feel a little better.
“It was nothing really. I just wanted to go home and they wanted to stay out.” Alex said as he looked at the window of the diner.
“Nah, something else happened. Earlier, you said it was a bad night, so something had to happen to make it a bad night. I just want to see if I can help. It’s what I’m here for.” I knew I was taking a chance but I really wanted to help.
Alex looked back at me and gave a long sigh.
“Ok so Mia and Shane wanted to go to this club that’s over by the docks. I really didn’t want to go because it’s where my ex likes to go and with it being a friday, I knew it was a pretty good chance he would be there.”
“Was he?” I asked as I leaned back and adjusted to a more relaxed position in the booth.
“He did show up but I’m not sure when he actually got there. We had been there for a bit before I ran into him at the bar. I was getting another round of drinks for us and he just happened to be getting something for himself. It wasn’t a long interaction but I just sorta lost the will to be there. So I just told Mia and Shane I didn’t feel good and left.”
I knew that Alex’s breakup was rough. He worked from home a whole week after it happened. He had said it was covid but I heard the truth from Mia. Shane was also useful in that he told me what caused the break up.
As somebody who had been cheated on, I knew that it sucked and how it could be hard to get over that. It was the main reason I had not really started dating again myself.
I wanted to pry a little more but I decided against it.
After we ate we walked over to Alex’s apartment. Just seeing the building and lobby I knew Alex was definitely doing better financially than I was. We entered the elevator and Alex pushed the button to his floor. The trip felt longer because of the silence.
As we exited on the 25th floor, I followed Alex down the hall, trying my best to not watch his hips and ass as we proceeded down the hall. I stood off to the side as he unlocked the door and then followed him inside.
The entire apartment was spotless and just as tidy as he kept our office.
“Alex, I have to say this place is really nice!” I said while I looked around.
“Thank you! Do you want a drink or something?” He asked while moving to the bar on a wall across from the couch I had just sat down on.
A few moments later Alex came and sat down on the couch next to me with two glasses, each with a goldish liquid and perfect ice sphere.
“Hope you like it.” Alex said, sipping his before eagerly watching, waiting for me to taste my drink.
It was slightly sweeter than I expected but not bad. The carbonation was a nice touch.
I took another large sip before putting down my glass.
“Pretty good. What is it?” I asked.
I watched as Alex sipped on his own glass before pausing to answer my question.
“Jack Daniels Tennessee Honey and ginger ale. Simple but really good” he answered before going back to his drink.
We sat for another hour or so just talking. It was nice to do this as I had said earlier, I didn’t have much of a social life and so just enjoying somebody else’s company was nice.
I watched as Alex put down his glass and looked at me.
“So James.. I have a question and if it makes you uncomfortable you don’t have to answer.”
I was leaning back on the couch but I sat up so I could see what this question actually was.
“Oh this could be interesting!” saying as I put my glass on the table.
“Go on,ask!” I said with a smirk.
“So do you like guys? I kinda never really got a read on you and well.. I just wanted to make sure before we go any further….” Alex said, his voice trailing out as he got to the end of his sentence.
I leaned back and took another sip of my drink.
“Do I like guys? Most guys? No, but if we are talking about you, then I could make an exception.” I watched as he quickly slid over on the couch and kissed me before I could continue.
Alex broke off the kiss as he readjusted and straddled my lap. I watched as Alex leaned down kissing me again, this time letting our tongues meet. While his lips had looked soft I wasn’t ready for how soft they really were. I moved my hands down along his sides before squeezing his ass, causing him to let out a cute moan without breaking our kiss.
Alex leaned back and wiped a small string of spit from his mouth. Instead of unbuttoning my shirt Alex roughly pulled it open, causing the buttons to go flying. I heard the small taping of the buttons on the floor around us.
“Just so we’re clear, you owe me a shir…. Oh fuck!”
Before I could finish my statement I felt Alex take my right nipple in my mouth and lightly bit down. I had always had sensitive nipples but more than a year with no stimulation had made even that tiny bite overwhelming.
I looked down to see Alex with the nipple still in his mouth while I felt his right hand caress me lightly as he worked his way up and pinched the other nipple still while sucking and licking the other one.
Alex released my nipple from his mouth, giving one last lick before moving up to my neck, all while giving shallow bites.
This whole time my erection had been straining hard against my jeans, Alex’s grinding not making the situation any better. Alex finally noticed and got up from my lap before reaching down and undoing my belt and the button for my jeans. I watched as he started to pull my jeans down and stopped halfway, My jeans now sitting by my knees as he released the waistband of the jeans and I felt his fingers slide into the band of my underwear. Alex got on his knees between my legs and laid his head on the area of my boxers that was straining against where my dick was. Alex laid there and I heard the deep inhale then I could feel the hot air from his nose as he exhaled taking in my scent deeply. I was never a scents kind of person but he seemed to really enjoy himself.
After getting his fill, Alex proceeded to remove my boxers and the jeans he started to take off earlier before getting ready to return to his knees before me.
“Hey Alex, don’t leave me being the only one undressed.” I said as he had already got down on one knee.
Alex stood up and I watched as he pulled his shirt over his head allowing me to get a good look at him. He was actually a little more muscular than I was expecting but he still had a smooth body just very well toned. I watched as he turned so his back was facing me, wanting to give a little show for me as he removed his jeans revealing black thong that was lost in his ass only noticeable by the gold fabric making its way around his hips as the dim light of the room reflected off the bracelets on his wrist.
I watched intently as he refused to turn around but backed up to me before lowering himself and grinding on my lap for a bit before standing back up. Once again I sat up to take in the sights but Alex turned around and with more force than I expected, pushed me back on the couch. He was enjoying this little show and so was I. Alex seemed to know what he was doing and I Was perfectly fine letting him dictate how the night was going to go.
Alex finally returned to the floor, slowly dragging his finger, teasing along my legs. I had to concentrate as the feeling had been electric and I wanted to stay as relaxed as possible.
My dick had been leaking pre almost the whole time, giving a heavy shine to my foreskin and a slight puddle on my stomach. I watched as Alex slowly licked the pre that was pooling up before making his way back and peeling more foreskin down, quickly taking my dick into his mouth, the warmness almost causing me to shoot my load right then and there.
I was worried about lasting as long as it had been awhile since I was with anybody and a quick shot would have really ruined the night, or at least that was how I felt.
I felt a slight tinge of jealousy and then anger at how Alex’s ex could have cheated on him and given up someone who was this good at taking care of someone. Those thoughts were quickly thrown out though as I felt Alex wrap his tongue around my balls.
“Fuck…….” My cursing turned into a deep moan.
It had been the first word that had been said in what felt like hours.
I looked down to see Alex looking up at me, a look of pride and satisfaction on his face, the trail of spit still connecting from his lips to balls.
I reached down and placed a finger under his chin lightly directing him back to kiss me.
As we held the kiss I finally noticed his dick pressing against my stomach. It was a little longer than mine but not as thick and he was cut. I reached down and began playing with the head, his own pre acting as lube. Even as we continued our kiss I still toyed with him, enjoying the occasional moan and pant without breaking our kiss.
A sudden deeper moan, followed by several warm splashes on my chest was all the warning I received before Alex collapsed over my shoulder.
“You good?” I asked as he rested and tried to regain his composure.
“…..Yeah I just really needed that.” Alex said, though his labored breaths.
It didn’t take him long to recover after that.
“Can we move this to my bedroom? I don’t want to make a mess on the couch.” He said looking at the mess he had already created on my chest.
“So it’s fine to make a mess on me but not the couch?” I said jokingly.
Alex repositioned himself on my lap and began licking his cum from my chest.
“Well you’re a lot easier to clean than the couch!” Making sure to get every spot before standing up and offering me a hand to get up.
I followed Alex down the hall and to the bedroom. Alex kept the rest of the apartment as clean as the living room and kitchen upfront. As we walked to the room I could swear he was swaying his hips just a little bit more than his usual walk, knowing I was enjoying the view.
As we walked in the room, the room filled with a dim light from recessed strips on the walls. I watched as Alex slid on to the cream colored sheets, inviting me to join him.
As we cuddled up together on the bed, I let my hand run down his leg before taking his dick in my hand again, the twitch he gave showing he was still sensitive from earlier.
Alex had closed his eyes and just enjoyed the moment too much to realize I had moved to laying on my stomach between his legs.
He did notice though when I put the tip of his dick and wrapped my tongue around it. I wasn’t really sure on the best way to proceed but I figured that I could figure it out as I went.
I continued to lower my head, taking more in, but giving myself time to adjust. Alex’s movements spurred me on and gave feedback and let me know what was working. A quick twist of my tongue, a lick on the underside, brushing the head against the roof of my mouth. All of these gave feedback that I was doing it right. I was feeling confident and I wanted to try and take him deeper. I came up for air before trying to go deeper than I had before. I could feel Alex rubbing his hands along my shoulders before catching me off guard and placing his hands on the back of my head forcing me down a little further and producing a slight gag as I felt my nose touch the base of his, which pulled him back to reality and released my head.
“James, I am so sorry…… I just sort of got caught up and I got too rough! I’m sorry!”
Alex tried to get his words out but was fumbling. I couldn’t help but laugh at his worried reaction as I sat up and wiped the thick saliva from my mouth and took a breath of air.
“You think that was too rough? Please, give me some credit. You see me? I can take more than some slight gagging.” I said, quite proud of what I had accomplished, taking him all the way on my first attempt.
I pushed Alex back on the bed to his former position. He looked like he was going to voice more concerns but he held back. I had already known what I was going to do next. I know that my plan was just going to be to let him lead tonight but I wanted to have a little fun myself.
Alex was light enough for me to roll him over with no issue. I gave his ass a quick slap to watch the jiggle. I felt it would have been a crime not to.
I let my hands work their way down his back, tracing his hips before spreading his ass while firmly grasping his ass. I leaned over and gave light kisses as I worked down. I buried my face in his ass, giving a long lick all along his crack.
While I was pretty much flying blind while sucking him off, eating ass was an artform I was quite gifted at and I was ready to let Alex know this.
A few licks on his hole had already loosened it up enough for me to begin to work my tongue in. I couldn’t hear much from him as I was fully engrossed in working my way deeper. The only real feedback was his legs shifting and the occasional muffled moan. I could have stayed there forever but Alex had other plans as I felt him push back, slowly fucking himself on my tongue.
I pulled back and tok in the sight of Alex, lightly panting, the spot where his dick had been leaking on the sheets leaving a visible wet spot.
I layed on top of him, my dick wanting to be in his warm and waiting ass.
Alex rolled over and looked up at me.
“It’s been a while and… I want to ride you…. let me get adjusted first… you’re a lot thicker than what i’m used to”
I was more than okay with that and I wouldn’t want to go too hard and hurt him in any way, so I rolled over on my back, propping myself against the pillows and leaning back with my hands resting behind my head.
Alex leaned over to the nightstand and I heard a drawer open and close, followed by the sound of a cap releasing. I watched as Alex squirted the thick jelly like substance on his hand before working the liquid over my dick.
Alex swung a leg over me and moved forward, my cock poking his back. I felt him lift up and slowly guide me into his hole. I watched as inch after inch disappeared and he adjusted to me. I could feel the tremors in his hand as he made his way down.
I enjoyed the view and sight as he let out small curses and moans followed by a much deeper moan and tightening as he bottomed out. I felt the tightness right behind the head and the release as he lifted up and began to lower himself once more. The pressure to not fill him immediately was immense. I watched as he picked up speed and reached behind his head and undid whatever was holding his hair up without losing pace. Alex moved his hands from my sides to grab my chest and squeezing as he rode. I finally removed my hands from behind my head and reached once again for that wonderful ass. My own grip on him acting like a button for him to ride harder and faster. It didn’t take long though before Alex came too far and I came out completely.
I reached for my dick trying to line it back up before I was stopped by Alex. It had come at a good time as I had felt my load rising and thi allowed me enough time to come back from the edge.
I watched as Alex rolled over and pulled on a cheek inviting me back in which was all I needed before grabbing his hips and pulling him back on me.
Even with that short break though, I was at my limit is just a few more minutes and as I picked up pace, I leaned forward, putting all my weight on Alex, causing him to collapse as I laid on top of him, filling his hole with one of the largest loads of my life and forcing Alex to unload as well on the bed under him.
I rolled off Alex’s back and felt my cum flow down his hole and onto the bed.
Alex took a few more minutes before he rolled over and laid his head on my stomach.
“You know, If working late would lead to more nights like this, then I think I wouldn’t complain about it so much” Alex said, sleepily.
I laughed as I ran my fingers through his hair.
“Somehow I don’t think that’s true..”