White Collar Affair

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White Collar Affair

I was working as a financial manager for some years now in an important retail company. At my 27 years of age, I had managed to land a pretty nice job and I was planning to work my way up. My job was hard and I spent almost all day in the office, but I was good at it and I loved it. Usually, I'd go home late at night and watch some Netflix before falling asleep. On the weekends, I would do my workout routines and open the dating apps at night and maybe go out with some guy.

Lately, things hadn't been going great at my office. They were struggling with money, so the executive management team decided to let some people go. I was lucky that I wasn't laid off, but I had to pull my weight in order to keep the company afloat.

One of the biggest changes we had in my office was the new CEO. He was a big guy in his early forties with lots of experience in the field. His name was Robert.

I remember the first time we were introduced was at a morning meeting. He shook my hand with his huge right hand and I felt this warm energy running down my body. I smiled nervously and looked up at his bright blue eyes. He had some dark short hair with some grays in between and a trimmed beard, he was definitely my type.

"I'm Thomas... the Financial Manager..."

"I'm looking forward to working with you, sir." I stated, shaking his hand and smiling.

"I'm Robert Miller. Nice to meet you, Thomas." He said with a deep voice.

After the introductions, I had to present a new budget plan to everyone on the team. I remember feeling a bit more nervous than usual with my new boss staring attentively at me from the other side of the table, resting his face on his manly knuckles. He listened carefully and made a few comments at the end but all in all it had been a strong presentation. I couldn't help to blush when he grabbed my shoulder and said 'Good job, Thomas' at the end of the meeting. I quickly went back to my small office and continued working.

***

Time went by, and soon our new boss knew everybody's names. He was very good at keeping a nice work atmosphere, whenever he made a comment he was always constructive and honest. At the same time, he pressured us to do our best for the company. We were all working very hard.

I remember he would go around the office in his navy suit, and I would do my best not to stare at his round ass when he returned to his desk. His muscular daddy appearance was enough to entice my imagination.

Sadly, he was definitely just a fantasy and there were many reasons not to get involved with him. First, he was my new boss so that made him off limits and secondly, he was probably straight. But that didn't mean I couldn't imagine him fucking me hard on his desk.

Everybody knew I was gay and most people were okay with that. As long as I wasn't flaunting or discussing the details of my latest Grindr date in the break room, it was fine. My colleagues were all very open-minded.

One time I was talking to one of my colleagues, Jennifer, and she told me all the tea about our boss Mr. Miller. Apparently, he was going through a messy divorce and he had a teenage daughter. I had noticed he had some pictures of a blond girl in his office, so I guessed it was his kid. He didn't look like he was going through rough times, but I guess he was just a professional guy that kept his personal life separate from work.

After presenting my budget plan, I had been working overtime almost every day. I was getting exhausted and I thought about telling my boss. At the same time, I didn't want to be ungrateful as I still had a job. I knew many of the people that had been fired before he arrived, so I wasn't sure how to approach him. It was almost 5 p.m. on a Friday, so I had to take some documents to my boss before I could finish my shift. He had to check everything was in order.

I knocked on his big office and went inside. His office had a minimalist design with a dark and sleek desk, one leather chair that he usually sat on, and two chairs on the other side. There was a big window on the back and you could see the whole city from there.

I told him that he needed to see these documents, he took them and nodded at me. His face looked tired and sad, I had never seeing him like that. For a moment, I felt bad about complaining. He came to work every day with a smile, despite dealing with his whole divorce. He checked everything and then gave me back the papers. I was going to leave when his voice stopped me.

"Mm... Thomas?" He said standing up and getting close to me, I had to look up as he was a couple inches taller.

"Yeah, boss?"

"I know that I have been putting a lot of pressure on you... and I want you to know that I truly appreciate your hard work..." He commented putting his big hand on my shoulder.

His gesture didn't seem inappropriate or like he had any weird intentions. I saw his bright blue eyes and I felt strangely happy. I knew he really meant that, because we were alone so he wasn't putting a show for the rest of the team.

"Thanks..."

"Now, go home and rest. You must be tired." He commanded with his deep voice and a smile that made my body tingle.

"Yes, sir... See you Monday."

I left his office and went to get my things on my desk. I couldn't wait to get to my apartment and rest. As I pressed the button on the elevator, my boss rushed inside. It was a bit awkward and we just waited for the elevator to get to the ground floor. We were both standing next to each other, I could smell his manly perfume it was intoxicating. I said goodbye and went straight to my car.

Back into my apartment, I immediately got in the shower to relax. Feeling the water down my lean body I couldn't help to think about my boss Robert. I had kept my mind off him for the most part, but now I was wishing he was there in the shower. I imagined his strong tall body behind me, caressing my chest and kissing my neck. Using my fingers, I pictured his fat cock filling my tight hole. God, I wanted him so bad. Soon, I shot my load all over the shower floor.

That weekend, I needed to get laid urgently. The next day, I opened the apps and went hunting for a guy to fuck. Swiping right and left, I made a match with a guy that looked in his forties. He had a buzz cut and a beard. He sent me a picture of his fat cut dick. I needed it.

In no time, I got cleaned up and ready. I looked in the mirror and fixed my short brown hair. I had always been on the thinner side, with some lean muscle definition. That day, I went for a dark green tee that complimented my hazel eyes and a hoodie with some dark jeans. My ass was looking nice and round in my jeans.

The guy's apartment was in the city centre, just a few blocks away from my small apartment. I went outside and headed that way. The streets were full of people, as usual for a Saturday evening. The shops were closing and people were walking home. I had to cross a park to get to this guy's place. That's when I saw him.

My boss was wearing some loose running shorts and was walking a big husky dog. He had stopped to drink some water. He didn't see me as I passed by. It was a surprise to see him in something different than a suit, I barely recognized him. His sleeveless hoodie revealed some strong arms. As he kneeled to give his dog some water I noticed his hairy calves. He caressed his fluffy dog and smiled. Some crowfeet appeared next to his blue eyes. I just melted, he was a stunning man.

A guy running came my way, and I snapped out of it. I got out of the park and found the apartment. Once I got up and knocked, the door opened and I saw my date. This guy was nothing like his profile picture. He was shorter and probably a few years older. I was already there so I decided to just go for it.

Immediately, we began kissing. He was briskly grabbing my ass, and removing his clothes at the same time. Then he got down on his knees, I let him blow me and then I turned around so he could fuck me right away. There was a sofa in his apartment so I just got my pants down and waited on all fours. My hole was ready for him.

The only think he didn't lie about was the size of his cock. I yelled as soon as he popped the head in. It was considerably thick. I closed my eyes enjoying his meat filling me up, inch by inch. Soon, he was going in and out, his movements changing from slow to a faster pace. My hands were grabbing tightly onto the sides of the sofa.

In no time, his cock was pounding me hard. His rough hands shifted from my hips to my shoulders and he was jackhammering my pale ass. My eyes were rolling back in ecstasy.

"Fuck...You're so tight baby..."

"..Yeah...Fuck me daddy..." I whispered looking back at him with a dizzy look on my face.

In the heat of the moment, flashes of my boss Robert came through my mind. His strong hands, those blue eyes, seeing him in his workout outfit, I couldn't help to think of him at that moment.

"...Oh fuck... Fuck me Robert..." I blurted out while he was pounding me.

"...What?" He asked confused.

"...Nothing... k..keep fucking me..." I said embarrassed. It was the first time I yelled someone's name while fucking.

He continued pounding me hard on the couch, grabbing me by the shoulders. His huge balls were making lewd sounds against my body. My ass was so full of his thick cock it was driving me crazy, I was moaning desperately. Soon, his thrusts became faster and I could feel his orgasm was close.

"I'm about to cum...Oh god!" He pulled out, took the condom out, and came on my back.

I had to jerk off to finish. Then I left his apartment and spent the rest of my weekend trying to relax and not to think of work and my hot boss. Although I definitely didn't want to admit it, I always had a thing for older men. When I was a teenager, I wasn't interested in boys my age but I always felt weak and nervous around their fathers or older brothers. There was something about their confidence that made me feel this incredible attraction.

***

Monday, I was back at work. We stopped working extra hours so that was great, everyone was glad about that. However, my boss was looking extra gloomy. He called me into the office at the end of the day to give him a full report. I had to stay a bit longer to finish everything. At that point, I think we were probably the only ones left in the office.

I was sitting in front of him explaining everything on the desk, pointing to the different numbers, and graphs on my report. He nodded and stared at me with those piercing blue eyes. He had taken his jacket off. After a long day of work, I couldn't help to notice his smell and felt my cock get stiff. Shit. Maybe it was his aftershave or perfume, but there was definitely something about him that made me crazy. I was trying to finish my presentation and get out of his office without him noticing my arousal.

Suddenly, he grabbed my wrist with his huge hand startling me. In a second I wondered, if his hands were that big what his dick would be like.

"That's enough for today, Thomas. I'm very pleased with the results." He mentioned with a sad face.

"...You okay, sir...?" I dared to ask.

"Yeah, it's just... Can I be honest with you?"

"Sure..."

"Well, it's the whole divorce thing... Tomorrow, I have a meeting with my lawyer to sign everything and then I'm finally done..." He sighed grabbing the sides of his brown leather chair.

I could tell he needed someone to listen to him.

"My daughter tells me it's the right thing to do and that I should start getting myself out there and meet new people... But who would want to date a divorced guy in his forties?" He added looking at her picture and then staring at me.

I couldn't believe this guy couldn't see how hot he was.

"If I may say so, I think you're a very handsome man and I bet many ladies would be interested."

"Hell, even guys would be all over you if you joined a gay dating app."

I immediately regretted saying that last thing to my boss because he gave me a different look. He was now aware that I found him attractive. My face was probably blushing after that realization.

"You really think that, Thomas?" He asked with a sly smile. Was he hitting on me? I couldn't believe it.

"...Uhm...Yeah..."

The tension between us was killing me. The desk was the only thing dividing us and covering the obvious hard-on in my pants. He was my boss and right now he had me in the palm of his hand. We were alone and he had complete power over me.

"So... what would you do if I were gay?" He teased leaning back on his leather chair, spreading his strong legs.

For a moment, I just froze not knowing what to do. An alarm was buzzing in my mind telling me this was a bad idea. On the other hand, my pants felt tight and I couldn't think straight.

"...I just..." I mustered but it was too late.

"You know what..."

"I'm sorry, Thomas... This is highly inappropriate and the last thing I need is someone filing a sexual harassment complaint..." He said scratching the back of his neck.

Then he stood up and guided me to the door.

I needed to make my move. His hand was opening the door.

I couldn't continue lusting over him every day. So, I just said it.

"You want to know what I would do...?" I whispered staring up at his eyes. He was holding the door for me.

"I would blow you on that chair and swallow every drop." I stated and I saw his impressed face. We were both still for a second.

His right hand slowly closed the door. Our eyes met. Both waiting for the other person to back down. He put the lock on and the blinds made a shutting sound. He went back to his chair. I followed him and stood in front of him.

I gulped. I couldn't believe it. It was my daddy fantasy come to life. There he was, resting his manly hands on his chair, looking all handsome wearing his shirt and tie. His legs wide open, revealing a big bulge in between. I loosen up my tie and went down on my knees. The sun had just come down on the city, so the room was filled with a dim golden light.

"Go ahead, Thomas..."

I slowly caressed the outline of his big cock over the soft fabric, I could feel it getting hard. With my fingers, I began by unfastening his pants revealing his white boxer briefs. His meat looked huge under the cotton fabric, it was a nice cut cock leaned to his left. I licked my lips and my head went down. My hot mouth was kissing and licking his cock, paying special attention to the head. My spit was soaking his white undies and the head started to show. I wanted to give him the best blow job ever.

Being so close to him his musky scent had me already leaking precum. My right hand began to grab my cock over my pants. I wanted to really savour that moment, I was kissing and burring my face down his balls. Sniffing him like a good dog. He rested his head back and started panting. His fingers swiftly loosen up his tie and began caressing his nipples over the shirt.

Once I teased him enough. I lowered his underwear and his cock sprung up almost hitting me in the face. He looked down on me and smiled, seeing my surprised face at the size of it.

I grabbed it with both hands and began jerking him nice and slow. I wanted to see how big and hard he could get. It was a perfect cock with veins going around and a big pink head that was already wet. Slowly, I put the tip in and tasted his sweet precum. I couldn't get enough of him. I was spitting and licking his cock like a hungry boy. While my hands were jerking him my mouth followed the same movement. My moans were muffled by his cock.

"...God... your mouth feels so good..."He whispered closing his eyes in pleasure.

I was delighted to make him feel that good. After getting him wet enough, I looked at him with my hazel eyes and I took his whole meat in until my nose touched his hairs. I managed to put the whole thing in for a few seconds, before choking. Over and over, I stuffed his huge cock down my throat making eye contact with him. His massive body was shaking.

"...F..fuck!...Thomas..." He blurted grabbing the sides of his chair. He calling my name made me the happiest guy.

"You like this, sir?" I teased while slapping his meat on my face and catching my breath.

"It feels amazing..." He said smiling.

For a few minutes I enjoyed his cock, licking and kissing from his balls all the way to the head. A line of spit came up to my lips. My right hand began stroking him hard, and his cock began throbbing. I wanted his cum so bad. I began sucking him real hard, I could feel his orgasm was coming.

"Oh god!...I'm coming...Shit..." He yelled shooting a load of hot cum down my throat. I quickly swallowed it all.

It was so much that some of it dripped down the sides of my mouth, he probably hadn't had an orgasm in a while. I took it out and he saw my dizzy face with his cum dripping down my chin onto my tie. His body was still shaking from such an intense orgasm. At the same time, I began quickly jerking my cock until I came. With my hand I wiped my chin and licked my fingers. He tasted better than I imagined. He was looking down at me impressed by my naughtiness I guess.

After that he put is cock back in his pants and I did the same thing. As he was fixing his tie when he said:

"Well... I think that was by far the best blow job I've had..."

"I'm glad to hear that, sir..." I said getting my things.

"I think is better that we never... ever speak of this. Understood?"

"Yes.."

"Good. Go home now and see you tomorrow."

"Bye, sir." I replied leaving his office and running to the elevator.

I couldn't believe what had just happened. It all seemed like a dream. On the way to my apartment, I could still taste him. His smell and his moans, I just kept replaying the events in my mind over and over again. That night, after the initial rush had passed I wondered about the reality of the facts. How would I face him now at work and would I still have a job after what happened. Either way, I was happy to have fulfilled my fantasy.