Andy is Trying - Chapter 10

ANDY IS TRYING

Chapter 10: Andy is Screwed

It was December and I had to get used to a chiller weather from what I knew back in Arkansas.

I wore pull-overs, winter shoes… And I was fooling around with my boss to keep myself warm.

In the couple of weeks which followed my date with Darius, David and I were a bit more distant within the days, - I think it had mostly to do with the fact that he was rarely at the office -, but we would meet again every Thursday night.

It had become some sort of a ritual.

The last employee would leave the building and I would walk, or crawl (depending on my mood), inside David’s office.

One time, I even sucked his dick while he was on the phone with one of his lawyers.

Wealthy and powerful men have multiple lawyers, do not ask me why.

As the days went by, I managed to convince myself that I was not doing anything wrong as David was the only one of us committed to a relationship.

Delulu was my middle name apparently.

Anytime I was feeling bad about myself, I was telling me that if it were not for me, David would cheat on his wife with Galvin or whoever else.

It was not what he was telling me though, pretending that I was different from the others.

I was not that special, nor that naïve.

As for Darius? Well, at this point, we were not moving forward much.

We were chatting through texts, I saw him a couple of times at the restaurant, and our exchanges were a bit ambiguous, but I was waiting for him to make a move and take things to the next step.

Partly because of his attitude towards his ex, I wanted to give Darius the opportunity to take the lead; that is, if he ever wanted anything to do with me.

I must say though, whatever was going on between David and I was certainly having an impact on my own attachment to Darius. 

I was telling myself stories that the sexy chef needed a little time and some space by himself before moving on to another relationship, but the truth was, I was the one who needed to figure out what I wanted.

In the end, it was like I was cut in half.

I found myself in a cute but very platonic relationship with Darius, getting to know him without any sort of physical intimacy.

And on the opposite side, I was in a purely sexual relationship with my boss, with whom I was not talking much but getting some spicy action anytime we were alone together.

Meaning, every Thursday night when Rebecca was having dinner with her powerful father.

Working was a great help in keeping me distracted from my tumultuous desires.

I was now fully integrated within the team and we had launched our first surveys to potential conservative voters to define David’s political agenda.

I was therefore spending a lot of time with Rebecca and Philips to finalize the surveys and to analyze the first results.

I even got to a first-name basis with Philips, now, I could call him Bradley!

Maybe someday I would even get to just call him Brad.

Obviously, I was still referring to Rebbeca as “Madam” or “Ms. Crown”.

I believe my mind was fully dissociating when I was working with Rebecca, as if I was putting aside, in a tiny little box in my brain, the fact that I was sleeping with her husband.

It was effective.

The worst part was that I actually learned to enjoy working with Rebecca and she seemed reversely happy with me.

I also learned to hate the old and MAGA conservative Broadhall, trying to get the governor’s seat for the third time, as much as she did.

We got to a point where we could joke about that and make fun of our opponent.

I found Rebecca smart, very qualified, and straight to the point, but I already knew that.

Besides, when I said that I was sleeping with her husband, that was not really the case.

So far, we had stopped ourselves at the blowjobs and some (rather delicious) ass-eating.

Was that even cheating?

Okay, I know… It definitely was.

But trust me, the human being is capable of rationalizing many things to justify their own actions.

And in any event, the excuse of “non actually” fucking did not last for long.

What was meant to happen happened.

And for this one, I think I can blame it on Cody.

He had sent me his scholarship application to take the final exams of his degree and he still had not found anyone in the field of urbanism, design, or architecture to endorse it.

I was correcting some typos in his presentation when it hit me.

I did happen to know the person in charge of urbanism in Philadelphia! I even had a pretty intimate relationship with him.

David Crown was respected, an important business man and a well-known politician in the city. His endorsement would for sure get Cody’s application on top of the list.

It also happened to be a Thursday late afternoon meaning that he was at the office… And Rebecca was not.

In all fairness, I could have done things differently to keep things professional.

For instance, I did not have to wait for practically everyone else to be gone to knock at David’s office.

“Is everyone home already?” He asked, surprised.

I would usually wait a couple more hours to sneak inside his office, and generally, he would already be playing with his fat cock.

As he said that, I realized that we had definitely made this a pattern. Oopsie.

My boss was expecting me to come to service his dick instead of even considering I could be there for work.

“No. I… I wanted to see you about something else.”

David seemed disappointed that I was not there to blow him.

He kept his cock in his pants and his hands above the desk.

“How may I help you? Another polling question to approve? You know I trust my team. Anything you come up with is fine by me.”

“It’s not about work actually.”

There was a spark in his eyes.

“Come in then, and shut the door!”

Fuck, he thought that I was getting a head start on our weekly shenanigans.

I did shut the door but I stopped him right away.

I mean, there was no way we would do anything while a few of my co-workers were still in the open space nearby! Right? We were not that insane.

I was just getting friendly with Bradley after all, I did not want him to catch me on my knees.

“Hold on, David. This is not what you think it’s about either.”

There it was again, the disappointment.

“Just state your piece, Andy.”

“I wanted to know if you could help me with a personal matter.”

His features softened. He truly looked gorgeous.

“Of course. Anything.”

“Well, it’s more a favor for a friend actually. My roommate’s been working for years for his architecture degree but he could not finance his final semester and he had to postpone taking the exam. He should be eligible for a scholarship but they didn’t grant it because his application was not endorsed by a third party, someone recognized for his work in urbanism, or …”

“Say less.” David cut me off, seeing where I was going with that.

“I wouldn’t ask this if Cody didn’t fully deserve that. He’s working tirelessly and he didn’t get the scholarship last time on a pure technicality.”

“That’s fine. Where do I sign?”

I was taken aback.

I put the application on his desk. It was quite a large file.

“You should… I mean, you should take a look at his submission before endorsing it, right?”

He puffed.

“You’re cute, Andy.”

That did not help.

“I don’t want you to do this because of what we’ve been doing.”

“And what have we been doing exactly?”

“You know…”

“Yes, I know that you’ve been doing some tremendous work since you’ve joined our team. I know Rebecca talks highly of you and of your dedication and I fully trust her judgment. And I, for one, can also speak for your deep involvement in our project.”

He winked at me.

Why did he have to add this last part?

“David…”

“So, if you’re telling me that your friend deserves this, I’m glad I can help him and I think it’s a great use of a favor.”

The way he had put it, I felt icky.

I did not have that in mind when I decided to ask for his help, but now, it felt very much like some sort of a bribe.

I wished David would have taken the file, read it, and then, did whatever he decided was fit.

Now, he was just doing this for me.

Yet, I thought of how much it would mean for Cody and I could not take that away from him. He had literally spent weeks on making sure his application was the best possible, he was counting on this so much.

So, instead of insisting on no special treatment, I just said:

“Thank you, David.”

“I’ll take a look later and write a little something when I sign this. Just… Come back to my office before you leave work so I can give it back you. Right?”

I cringed and bit my lips.

Would have I come back to his cock anyway? It was very likely.

Did he just seal that I would with that move? Certainly.

Was I still free to refuse? Of course.

But let’s be real. That morning, I had decided not to wear underwear with my jeans. I was fully expecting a late and private evening with my boss.

Maybe I could not so much blame my slip-up on Cody after all…

“Sure. I… I’ll see you later then.”

I went back to my desk with a raging hard-on.

Because I had decided to go to work commando, - something I would have never thought of in my life before Philadelphia -, I thought my excitement was pretty much on display.

Thankfully, Laurie was already gone and the others did not seem to pay the slightest attention to me, too busy trying to get done with their work to come back to their families.

Phillips, or rather Bradley, had told me that he was getting scolded by his wife for coming home too late and he did not want to “divorce for a job.”

Yet, he seemed to be working as much as Rebecca was.

Would Rebecca go through a divorce? Would it be because of me?

I should not have been thinking about that.

When Bradley left at 9 p.m., I was finishing compiling the data of thousands of surveys.

You bet that Rebecca was satisfied with my work, me waiting for her husband to be available and the office to be empty, had made me work extra-hours since the very beginning of my employment.

The woman should thank me!

Okay…

I may have gone too far with that one but I was about to, once again, walk into her husband’s office and take my clothes off.

I needed to fabricate an excuse so that it would not feel so wrong.

*

When I got in, David seemed to be working. It was a first!

“Hey, Andy. I’m finishing the endorsement letter.”

“Oh, thank you so much.”

“I did read the application. It’s a shame someone like him has to work two jobs and still not being able to get a loan for his tuition’s fees.”

“Are you sure that you’re a Republican?” I teased him.

“I’m a Republican who believes that talented and hard-working people should be able to get a degree in this State.”

“I’ll tell Bradley about it; we’ll include that in your campaign promises.”

David chuckled.

“You do that.”

He printed the letter and added it to the application.

“Honestly, thank you for that. You didn’t have to do this.”

“Please. Just take that and go home to your roommate.”

I did not expect that

A smile grew on David’s face as he handed me the file. He added:

“Unless… Unless of course you wanted to stay a little longer?”

The fucker!

He knew exactly what he was doing.

“Depends on what you have in mind.” I said cheekily.

“Absolutely nothing to do with work. That’s for sure.”

My eyes fell down towards his crotch. I felt myself getting red.

I put the file back on the desk.

“What could we possibly be doing if it’s not about work, boss?”

I wrapped my hands around his neck.

“So many things… And in fact, I’ve been thinking…”

He kissed me on the lips.

“Yes?”

“I’ve been looking at the jeans you’re wearing today… The very tight jeans and the ass that they give you… Splendid butt…”

His hands went from my back to my ass.

He groped me lewdly.

Did he notice that I was not wearing any underwear?

“Yes? Go on.”

I kissed his neck.

“I’ve been thinking you might want… You might want to take this to the next level.”

He whispered the last sentence so low that I could barely hear it.

Yet, it gave me chills as I understood what he was hinting at.

That being said, his hands caressing my ass was another clue.

It was not the first time either that he was mentioning my quote-on-quote “peachy bum”, “splendid butt”, or “great ass”.

But until that point, I had resisted crossing that last barrier.

“The next level? And what would that be?”

I liked to play the innocent card when I knew damn well that I was not fooling him. It was part of our little games.

He got his mouth even closer to my ear.

He even slightly bit it and then he muttered.

“Fucking your ass, baby.”

The shivers were definitely there, running through my whole body.

My asshole itself may have twitched.

Or maybe it was his hands going down underneath my jeans, feeling me bare, which were giving me the butterflies.

We kissed again. We were doing that a lot, making-out.

See my excuse about not really cheating on his wife… As if!

What can I say? Those were my favorite moments.

“Yes… I… I think I want that… I want you to be inside of me… Fully.”

Our bodies were already glued against one another. I could feel the erection growing in his suit pants.

Did he feel mine?

He seemed very much focused on my ass for now.

“That’s the most beautiful thing I’ve heard in a long time.” He spoke softly.

David took a step back. Indeed, his hard-on was impossible to ignore in his pants.

I was weak for it.

I wanted it so bad.

“Fuck me, then. Now!” I heard me say.

He was scanning me from head to toes.

“Would you take your clothes off for me? Start with your pull over and your shirt. Take your time.”

I used to be modest; I used to be shy; I thought my body was too lengthy, too skinny; but with David, I felt secure… And I felt slutty.

I stripped for him.

I took my glasses off to remove my pull over and I slowly opened my shirt. Just like he had requested.

“Put them back on.” David said, handing me the glasses.

“Really?”

“Yes, really. I like you with them.”

“Okay. But you should strip too. I want to see your hairy chest. I miss it.”

David smirked and obliged immediately.

I believe that it was the fifth time we were finding ourselves in his office, after dark, by ourselves.

Each time, we were getting more comfortable, more familiar with our respective bodies, our desires, our limits, our kinks.

I unbuckled my belt and my jeans sagged a little.

I liked the way it was revealing more of my body. One thing I was proud of was my V-lines.

They were much more defined than David’s who was bulkier than me.

“You wanna see my dick?” He whispered.

He was caressing his crotch through the fabric of his pants.

“Don’t ask stupid question.” I replied.

He giggled like a teenager.

“You’re right. Of course, you do want to see it… To feel it.”

I stayed still, looking at him as he was getting naked in front of me. No surprise there, he had been free-balling all day. David seemed to hate constraining his massive junks in more fabric than necessary.

I was withstanding myself from grabbing my own cock.

“Your cock is perfect, sir.”

It truly was.

Always, I was in awe of its girth, its length, his prominent veins, his cockhead, his foreskin… He had the cock of a man blessed by the Gods.

Big dick energy realness.

Sometimes, I still could not believe that he was even slightly interested in me.

I had not become a sex machine.

I was still my very nerdy awkward self.

But apparently, he liked me like that. Glasses included.

“When you look at me like this, you wake up my rawest instincts.” He said, leaning against his desk.

His massive cock was pointing to the ceiling.

Good Lord, I would really take that huge thing in my hole?! Would he hurt? Probably. Would he feel good? I was sure!

“Am I? Am I making you horny? Do you want to… to use me?”

“Fuck, Andy. Should I be a little rough on you?”

I gulped but I nodded yes.

In many of my recent fantasies, David was making me his little bitch.

“Say it then.” He insisted.

“I want you to fuck me like a rag doll.”

I was the one saying those words but I could barely believe it.

There had been many years of filthy and unreachable fantasies building in my head, and since I had moved to Philly, since I had met David, it felt like I was finally authorizing myself to live them.

As soon as I had said the words though, David jumped on me.

He held my entire body and took me off the ground.

“You’re mine, Andy! You’re fucking mine!”

I wrapped my legs around his back as he carried me.

“Aaah…”

He was also licking my neck.

I mentioned this before, David Crown was an excellent multi-tasker.

We turned around and he put me back on the floor.

“Turn around, slut. Bend over on the desk.”

“David…”

He grabbed my neck and made me move. I was his puppet.

“This is what you want, eh? A real man handling you like you deserve?”

“Yes… Yes, please… This is what I want.”

He slapped my ass.

I was still wearing my stupid jeans… But not for long.

David practically tore them apart as he went behind me to expose my butt.

“This is what I’m talking about, no undies! And this is the ass that deserves all my attention!”

He spanked me again, but this time, his hands were slapping my bare and pale bum… quickly turning red.

SLAP.

SLAP.

SLAP.

“Aaah… Yes… Please, more… I’ve been a very bad boy…”

Was it me saying those words?!

What the hell had I turned into?

“Don’t worry, I’m here now. I’ll teach you how to behave, Andy.”

He grabbed my neck, almost choked me, but then, he pulled and guided my hair to make sure my face was smashed against the wooden desk.

My nose was almost touching Cody’s application file.

Behind me, I felt a huge piece of wood rubbing against my crack. It was wet but it was fully hard.

“Eat me first… Please.”

I thought that was a reasonable request, but in any case, my “master” would have done anything I would have asked of him.

As always, I was the one truly in control of the situation.

I was writing the scenario.

Seconds after my demand, I felt David’s face against my ass and his tongue tossing my salad.

“I love your ass, Andy. I just love it. I love you.”

No. I did not take those words at face value. The man was mesmerized by my asshole.

I got that.

Victor described it as the best he had ever had.

He was a prick but I do not think he was lying on that.

“Hmmm… That’s it, David… Aaah.”

Already, he was reaching the most sensitive spots of my anatomy.

The future governor knew how to eat a hot ass without leaving any crumb.

Falling into my daze, - sex with David often gave me the effect of taking a hard drug -, he came back to my face and gave me his fingers.

The wedding ring was still there.

“Lick them off. Make them wet, bitch!”

I did as I was told.

And shortly after, I felt said fingers invading my hole.

It had been so long since I had not been fucked in the ass, I felt like I was losing my anal virginity all over again.

Yet, my asshole was naturally opening up for David’s dick.

I mean, it had been itching for so long. I had prepped it a little too. And once again, I have to say that the politician was very good at what he was doing.

He fucked me with his fingers, then with his tongue, then back with his fingers.

One, two, three…

He was opening me up and I was letting him take charge.

This was the most liberating feeling.

I did not have anything to think about.

David Crown had the mission of using, servicing and pleasuring me all at the same time.

All I had to do was to enjoy.

SLAP.

SLAP.

SLAP.

Another rounds of spanks.

His dick tickled my pucker again. I felt the cockhead pushing against my anal ring. He was in my ass crack.

The man grabbed my waist firmly, things were getting serious.

“Fuck me… Fuck me, please.” I mumbled.

“Since you ask so politely, babe.”

I heard the distinctive sound of David spitting on his dick, and he thrust his hips to get inside of me. For real.

My mind went wild as soon as he started penetrating me.

Just the tip of his cock was thick enough, he was already stretching me.

“OH GOD!”

I straightened up as I could not keep my face smashed against the desk.

He tightened his hold of my entire waist.

“Relax, baby, I’m just getting in… You have to relax…”

“Yes… Keep going.”

He pulled my entire body back until I was almost standing and he kissed my shoulders.

He got further inside my ass in this position before pushing me back against the desk once more.

“I recall you wanted to be rag doll? Eh? Fucking whore?”

The dirty talk was as exciting as his cock hammering deeper in my hole.

He was tearing me apart… But I asked for more.

“You’re getting near the spot. I can… Hmmm… I can feel it…”

His muscular chest was making one with my back. Because of his sweat, we were increasingly glued together.

David was now pounding me, thrusting his pelvis back and forth.

“I love it… Fucking hell, I love it… Your tight hole… That’s the shit that I want… Always… I’m gonna fuck you so good… I’m fucking you so good!”

“Yes, you are…. Keep going, keep going, more… More… Mooooore!”

I screamed.

I could not say how many inches I was taking deep but a large portion of his massive cock was now drilling me.

He finally hit the prostate and I saw stars.

David was grunting and roaring in my ears.

His dirty talk became more incoherent, I think he was losing his shit fucking me and that impression made me happy.

“Tell me that you’re mine… Tell me, Andy… I want you to be mine… Fuck, that hole belongs to me… Tell me that…”

“My hole belongs to you… I’m yours… I’m all yours…”

“Aaaaargh.”

I was dripping with sweat too.

The fucking was intense.

There was a tiny stain on Cody’s paperwork. Shit.

I pushed it aside and the file fell on the floor. The desk was too busy anyway.

And given what was about to happen, I had made the right choice.

David held my cock and started stroking me as he was still pounding my hole. Hard.

I felt like I had a huge truncheon making its way inside of me, wrecking my ass in a mad attempt to reach my guts.

Simultaneously, my cock was stimulated.

It did not take more than thirty seconds of stroking to have me paint a large part of the desk white.

“Oh no… David… Fuck, no!”

I was spraying dozens of documents with my sperm.

But I was an unstoppable geyser and David did not seem to give a single fuck about preserving work or official paperwork.

“Shut up, and enjoy, bitch!”

He even put his hand against my mouth to prevent me from talking… or yelling… or moaning…

I had to wait a couple of more minutes of intense fucking to speak up again.

There, I only had two words to say.

“Breed. Me.”

There was this extra-layer of taboo and filthiness to think he would deposit his precious cum deep inside of my asshole.

“I’ll mark you and it will seal our bound!”

Whatever boss, I just wanted to feel his juice in me.

“Yes, please.”

He was not done with banging me though.

He put his hands on my hips and there, he went on me like a bull, fucking the hell out of me.

Damn it, 46 years-old but the man had stamina.

This was a move only experienced athletes or very horny fuckers could pull. Lucky for me, David Crown was both.

BANG.

BANG.

BANG.

I was literally shouting, completely forgetting where I was and the risks we were taking.

“Aaaah… Yeeeeeeeeeeeeessss… Yeeeeeeeeeees…”

“I’m gonna cum, baby… I’m gonna bust my nuts inside of you…”

“Yeeees… I’m begging you…”

“I’m gonna destroy your tight ass for good.”

“Please…”

“Take.”

BANG.

“THIS.”

BANG.

“LOAD!”

BANG.

We were like a single entity and I felt the spasms running through David just as if they were running through my own body.

I experienced his orgasm and mine simultaneously.

His cock twitched inside my hole and I felt my ass getting filled with his creamy loads.

Best fuck of my life. No doubt.

David was wet with sweat and so was I. He let his cock deflating in my ass for a long time.

Neither of us wanted it to end. There would be no more first time.

We had to cherish this instant.

He was no longer dominant though; David was softly kissing my cheek. I shut my eyes and appreciated the bliss.

I did not want him to pull away.

When he did, I felt empty.

I felt sad too.

I was coming back to reality.

The mess in the office. The documents I was working on with his wife. The pictures of Zachary on a shelf. Cody’s application.

I felt dizzy for a whole other reason than the amazing sex.

I wanted so bad to spend the night with David, to cuddle and sleep in the same bed but this time around, I was the one who had to run away.

It would hurt too much to stay any longer.

The reality was there, laying in front of me, and my fantasy was gone, as soon as we were done fucking.

David seemed to get it. He did not try to make me stay.

What would have been the point anyway?

He only made sure I was not regretting what we had done and that I had had a good time.

How could have I regretted this? I had just lived something some people never got to experience in their entire life. A true orgasm.

I left as he was dressing back up.

“Wait!” David shouted as I was calling the elevators.

It was less than ten minutes after the fucking, meaning that I could very well feel the sperm coating in my ass.

He had released a huge amount of gooey milky juice. I could tell. Or maybe, it was my (dirty) imagination talking.

“David?”

“You… You forgot this.”

“Oh right, thank you.”

It was Cody’s application with the endorsement letter.

I recognized the stain on the first page but it did not look too bad. Cody would print it again, as long as the signed letter was safe.

I would say it was coffee or tea.

Who could think the stain was related in any way to sex with my married boss?

*

My head was spinning after the fuck and since it was not too late so I took my time to come back to the apartment.

I received a couple of texts from Cody but I ignored them.

I walked most of my way home.

I stayed alone with my thoughts; I did not even listen to music.

It helped getting me to a better head-space.

That was a thing my father used to say. A good walk is the best way to get yourself together.

He was right.

As always, as I was physically taking my distance with David, my brain was becoming saner and I could rationalize.

Besides, that night, I was coming back home with a great news that I could not wait to share with Cody.

He was home when I arrived a few minutes before midnight.

And he was pissed.

“Dude, I told you that you had to send me back the files in the afternoon. I have to submit it tomorrow and I still have a few things to add!”

Grumpy moody Cody was back…

“Wow, first of all, hello!”

“No, seriously, if you hadn’t had time to correct the typos, that’s fine. I didn’t even want to ask you for help but I’m super stressed with the timing.”

I smiled at him.

“Calm down, I’ve done the proof-reading and I’m sure you don’t have anything to add, your application’s already perfect.”

He sighed.

“Sorry. I didn’t mean to jump on you. This thing just drives me nut. I don’t know why it’s so hard to have a recommendation for a fucking scholar…”

I cut him off.

“You have one.”

“What?”

“You do have an endorsement. A strong one in fact.”

Cody stopped himself in his track.

He was confused.

“What are you talking about?”

I gave him the documents.

“Before you grunt about the stain on the cover, look at what’s inside.”

Cody checked it, perplexed.

“What’s that?” He asked, an envelope in his hand.

“Come on! Just open it!”

Frankly, watching Cody’s smile grew on his face as he read David’s letter was the perfect way to end the night.

He looked at me with teary eyes.

“Really? You got this?”

“Yes. I mean, it makes sense. Should be a big help, right?”

He nodded yes.

“Yes. Of course! I would never have asked that from you though… That’s crazy. How did you convince Crown?”

He came to hug me.

At least, I had done one thing right.

“Dude, you deserve it. So much. He read your application and he thought it was great.”

“But I didn’t think you were seeing your boss that much? I thought you were interacting almost exclusively with his wife.”

“I just gave him your submission and he thought it was worth endorsing.”

Cody laughed.

“Dang! Well, I hope you didn’t have to fuck him to get this signed!”

And right there, I was screwed.

I had been able to shut my mouth and not spill the beans, but I was not sure that I could outright lie.

Immediately, I felt my palms getting sweaty and I started stammering.

“What… What would you… What do you say that?”

“Andy, I was kidding. It’s just cause you told me he was fucking younger guys on the side, cheating on his wife in his office.”

He had made a simple joke and I was acting way too suspicious.

Of course, Cody knew about Galvin. I had shared that information.

“Oh yes… Right. That guy he had fucked… Once.”

Cody scanned me.

I saw the realization slowly sinking in his brain.

“Wait… Andy?”

See.

I was very bad at lying.

“Forget it. Just, enjoy the letter.”

“ANDY?! DID YOU FUCK WITH YOUR BOSS TO GET THE RECOMMENDATION LETTER?”

I nodded no.

“No, I didn’t.”

“Why are you acting so weird then?”

I took a deep breath and then, I added.

“I mean, the fuck wasn’t to get the recommendation letter…”

Cody’s face was the definition of jaw-dropping.

“You filthy fucker!”

I was about to explode; I had to tell someone… Right?!