Valentine's Day isn't the Worst - Part 3 (Patreon)

Part 3

We still had about four hours to drive to Portland, and Oscar volunteered, pointing out that I must not have slept too well considering how much I was yawning. Damn right he should drive, he was the reason I had so much trouble falling asleep! In spite of that, I had some of the motel’s burned coffee in a to-go cup and resolved to stay awake, though it did occur to me to try to catch a nap in the car.

“Something on your mind?” Oscar asked while he drove.

“Oh yeah, just, uh thinking about today, how it’s gonna go.” I said, which was partially true. In fact I wished the presentation today had my full attention. Instead I kept thinking about my nude boss, that round pink ass, furry front and heavy balls. I sighed to myself.

“Let me know if there’s anything I can do to help.” He said.

“Maybe I can run it all by you? See if anything jumps out as needing correction?” I asked.

“Sure thing, I’ll do my best! We all know you’re a lot better with this kind of thing though.”

I pulled out my laptop and began going through it line by line with the boss. He mostly nodded, listening intently. When I was finished he smiled broadly under his thick mustache.

“Really well done, Jim! Couldn’t be any better!” He said proudly, and I blushed under his praise.

“Well good, one less thing to worry about.” I replied.

We grabbed a quick brunch when we reached the city. I had a pecan waffle with avocado and a fried egg on top and Oscar had a rice bowl with salmon. He used to be a big steak and eggs type of breakfast guy but I remembered him telling me about his doctor needing him to eat more thoughtfully for his heart. Pizza the night before was a treat, but as long as I was around I helped enforce the doctor’s orders. If anything happened to the big lug, it wouldn’t be on my watch!

We left the restaurant and headed just up the street to a gleaming glass office building where we were going to meet our potential benefactor. The skyscraper was immense. We found the floor through a directory, took an elevator up nineteen floors, met with a receptionist and waited patiently on a very comfortable couch. We didn’t wait long for our meeting either, and ultimately we were shaking hands with a guy who couldn’t have been older than me. He wore glasses, was clean-shaven, and dressed, surprisingly, in just a tee-shirt and ripped jeans. Conversely, Oscar and I were dressed in slacks and button-up shirts, trying to give a professional vibe. The fellow seemed nice enough, shaking our hands, and even raising an eyebrow at the thickly-built older man towering over him.

“Aren’t you impressive.” He said, and Oscar smiled.

Once we all introduced, I gave my presentation, all forty-six minutes of it, and I think it went quite well! Admittedly though the fellow seemed to be more interested in his phone while I was speaking, but he did look up at the end of it to give a thumbs-up.

“Great stuff guys, really. Excited to do business. My people will work out all the details with you over the next week.” He said as he got up from his chair and began heading to the door.

“Wait!” Said Oscar. And the smaller man stopped to look at him. “So we’re, good then? You’ll provide the funding we asked for?”

The guy in the tee-shirt shrugged. “Yup. It’s good publicity for my company, and it’ll be cool to help those homeless vets or whatever. Real humanitarian stuff, I like it.”

“We’re actually mostly dedicated to helping houseless families, as Jim explained.” Oscar said, gently correcting him.

The man shrugged again. “That’s what I just said, anyway, you’ll get your money so, we’re good?”

“I should think so! Thank you very much!” Oscar said happily.

The man nodded, gave an awkward smile and left the meeting room.

“I guess that went well.” I said to Oscar.

“I guess so.”

It was only early afternoon when we left the corporate office building and stepped out into the brisk February air.

“We should celebrate!” Oscar announced suddenly.

“Yeah we should! Um, what do you want to do? What’s even around here?”

“I don’t know! But certainly Champagne! And a nice meal?” He suggested.

“It’s like one fifteen in the afternoon.” I said.

“Well, something quick for lunch and on the way back something special for dinner?”

“That sounds great.” I said.

So we found a sandwich place for lunch, walked around downtown Portland for an hour, checking out specialty shops, bookstores and the like until it was time to pile back into the car and drive south. I drove that leg of the journey while Oscar used his phone to find us a hotel and a place to eat. We drove nearly five hours back into Northern California and found a nice place to spend the night. Oscar explained he wanted to treat me for ‘wowing’ the guy earlier. If I’m being completely honest, it seemed like the dude was going to give us the money regardless, but hey, a win’s a win.

As we parked in the hotel lot, I couldn’t help but notice it was actually quite a bit nicer than our digs the previous night, in fact it was downright fancy.

“This looks nice.” I said as I opened my door and we grabbed our bags.

“Well you deserve it for today.” Oscar said. “And it has a well-regarded restaurant downstairs, and a bar too, according to the reviews.”

We headed inside, where a sprawling white lobby greeted us as well as a pair of smiling guest services personnel. Happily there was no shortage of double beds, so we made dinner reservations at the restaurant nearby and headed up to our room. The room was spacious, with a big flatscreen on the wall, ceiling fan, a whirlpool tub in the bathroom and a well-stocked minibar.

“You spoil me, boss.” I said as we set our bags down.

He surprised me by coming up and pulling me into a crushing bear hug.

“You deserve it, not just for today but for everything you do to help out our organization.” He said.

Something I’ve always liked about the man: He doesn’t shy away from physical affection. Although I’ll admit that in our early days of working together, I used to read into his hugs and back pats a lot more.

“We both do a lot.” I reminded him. “It wouldn’t even exist without you.”

He kept hugging me, probably a couple beats longer than necessary before releasing me.

“I guess we should head down so they don’t give our table away hm?” He said.

The dinner was good, not super expensive or anything, but well made. They didn’t have champagne really so we settled for a bottle of wine between us, and then a second bottle. By the time we got back to the room a couple hours later, we were feeling pretty good, and more than a little tipsy.

“I’m gonna go have my shower now so I don’t need to take one in the morning.” I announced to Oscar.

“Good idea.” He said.

I went over to my duffel bag to collect my toiletries as Oscar kicked off his shoes, pulled his socks off and unbuttoned his shirt. It was getting pretty late, so I understood his want to get more comfortable. I moved into the bathroom, peed, brushed my teeth and flossed. I looked at myself in the mirror, studying the bearded face that looked back at me. The funny thing was, I didn’t always like wearing facial hair, but a couple years back when my then-goatee had gotten a little longer than usual, Oscar made the comment to me that it looked good. Ever since then, I liked the look of it on me. I wasn’t a bad looking bloke I reasoned. I started the shower, adjusting the faucet until it was the warmth I wanted and stripped down to my underwear. Dammit! Forgot my shampoo in the room. It didn’t fit into my small bathroom bag, so it was in a different pocket of the duffel. I thought about putting my pants back on, but considering Oscar had stripped down to his skin in front of me the night before, I figured going out into the room in my boxer briefs was fine.

I opened the washroom door and headed back into the main room when sudden movement from the nearest bed caught my attention. Oscar’s hands flew to his crotch, but not before I caught sight of an impressive stiffie. His blue briefs were tugged halfway down his thighs and he wore nothing else. He was sitting up at the top of the bed, with pillows propped under his back and I could hear porn on the hotel television.

“Jim!” He yelled, in a very ‘I’ve just been caught’ voice. “I thought you were in the shower!”

“I uh, forgot my shampoo.” I said, staring at the big man’s hairy body. My mouth went quite dry. For the second time in as many nights I was at a loss for what to do.

“Oh well, that makes sense.” He said.

“I’m just gonna go grab it.” I said and crossed the room in front of him. He kept his hands glued over his privates, and a very red color covered his face.

As I walked over to my duffel bag at the far side of the room I couldn’t help but notice the porno he was watching. A hung, youngish dude was plowing some chick. On its own that would have been nothing worth mentioning, but behind the first dude was another guy, licking his ass and getting ready to fuck him!

Oscar seemed to understand what I was seeing, and addressed it. “Straight porn, sometimes, uh, doesn’t do it for me anymore.” He said quietly. “The bi stuff is more exciting I guess.”

I held up my hands to him. “You really don’t owe me an explanation at all. And I’m really sorry for interrupting you like this.” I said.

Also, damn. Mr. Magnussen just admitted to me that he sometimes liked watching guys fuck around with each other? That it was more exciting than old-fashioned straight stuff? The boss was just full of surprises wasn’t he?

“I just, I figured I had some time to myself while you were in the shower to, quickly rub one out.”

“Sorry again.” I said and grimaced.

“I usually get off every day, at least once.” He further explained. “So I was kinda looking forward to taking care of it tonight after not getting to yesterday.” He laughed, both at his admission and the absurdity of the situation.

“Oscar, it’s fine, I’m the same way. But listen, I’m gonna go take a nice, long shower. You have thirty minutes to enjoy your movie there, I’m even going to set an alarm so you’ll know when I’m done.”

He grinned. “That’s very understanding of you.”

“I get it man, happen to be a guy myself.” I said and reached for the handle of the bathroom door.

“Uh, Jim?” He asked, and I just knew there was something about the way he said it.

“Yeah?”

“You like this kinda stuff?” He nodded at the film.

I looked back to the screen where the second fellow was just beginning to slide a finger into the first guy, and the first guy grunted as he pushed deeper into the lady.

“Bisexual porn? I mean, I just kind of ignore the chick, so, yeah I could be down. Although I… Ah, nevermind.” I said, realizing what I was about to say.

“No, what? Come on, tell me.”

I rolled my eyes. “I like the guys to be older, you know, like greyer, more bearish.”

He smiled knowingly. “Ah yes, I should’ve guessed.”

“Anyway, I should--”

He cut me off, saying, “You could watch it with me, if you want.”

My hand dropped from the door handle and I gave him my full attention. “What?”

That had to be the wine talking.

He shrugged a shoulder and gave me a shy smile. “It’s already on, you caught me, maybe it’s something we could both enjoy? Nothing complicated, just a couple friends watching a porno together.”

I had certainly heard stories that straight bros sometimes did stuff like this, though I’d never been invited to join in before. The obvious answer of course was, ‘no thank you’ with a side of ‘you’re married’ but in that moment, it didn’t feel so obvious. In that moment, the hottest man I’ve ever known was asking if I wanted to jerk off with him.

“Come on, Jim.” He said and moved one of his hands to pat the mattress next to him. “Don’t overthink it.”

I still lingered where I was, overthinking yes, but also realizing that this would change the dynamic of our friendship forever. Even if he could act tomorrow like nothing happened, I knew I couldn’t even if I wanted to.

“Well, let me know what you decide then.” He said, turning his attention back to the screen and moving his other hand from his crotch. He was still hard I could see, and he went back to slow stroking, while I watched, hypnotized. My cock began inflating immediately at the sight, and I had to quickly make a decision.

“Are you sure you want me on the same bed? I could just be on mine.” I suggested, making sure I was completely understanding what Oscar was requesting.

“Up to you, I don’t mind either way.” He said, and gave himself another slow stroke. I was transfixed, watching his strong hand slide over his thick, uncut meat.

I sat down on the bed next to him, making sure to leave some room between us. My heart was beating a mile a minute.

“You can lose the underwear.” He said.

“Y-yeah I guess so.”

I lifted my ass off the mattress and slid them down to my ankles. My almost painfully hard prick slapped up against my stomach. My boss casually looked me over.

“You got a nice one, buddy.” He said.

“Uh, thanks, you too.”

Oscar gave himself a few long, slow strokes while I watched him. Each time he brought his fingers all the way to his tip and squeezed his droopy foreskin, forcing precum out the end where it would glisten in the light of the porno. My eyes darted to the screen but they couldn’t stay there for long. The real show was beside me.

I spit into my hand and started to jerk myself too, matching Oscar’s timing. He watched the movie more, but every now and then he’d check out what I was doing. Every time his bright blue eyes lingered on my cock I’d feel a surge of excitement.

On the screen the first guy was now on his back as the second dude began to stuff his oversized porn star dong inside of him. The lady wasn’t really involved in this part of the flick.

“Hey, uh, can I ask you something?” Said Oscar.

“Sure.”

“How does that feel? I mean does it feel good?”

“Getting fucked?”

“Yeah.”

“Why do you want to know?”

His eyes darted to mine behind his glasses. “Just, I wonder is all. Seems like it would be painful.”

“It can be.” I admitted. “But if you’re with someone you trust to go slow, open you up gently, at your own speed, it can feel amazing.”

“Huh.” Said Oscar, eyes still glued to the men fucking in front of him.

In fairness to him, he had asked me similar questions about ‘being gay’ before. He’s curious by nature, as am I, and I’ve actually always appreciated being asked about my orientation and the culture rather than have folks just make outdated assumptions. That said, he’d never asked me how it felt to be fucked by a man before. My mind wandered, and wondered.

“It’s not gonna take me much longer at this rate.” He told me.

“Me neither.”

And then the big guy shocked me.

“Do you mind if I?” He asked and lifted his rugged hand from his own cock and moved it towards mine. His palm was covered in his own spit and pre. “You can touch me too, I think it’ll feel good for both of us.”

My breath caught in my throat, and I felt blood pounding around my ears.

“Yeah, okay.” I managed to say.

I removed my hand as Oscar slid his down over my length, tentatively at first, exploring me with his flesh wrapped around mine.

“Oh Jesus…” I moaned.

He no longer even gave the pretense of glancing toward the tv. He was focused entirely on my maleness.

My hand trembled as I reached for him, this intimate part of the man I had been fantasizing about for years. It bobbed with anticipation as I touched it for the first time. The head was hot and spongy, mostly hidden under a fantastic foreskin which I peeled back slightly with my thumb and fingertips. He sighed and closed his eyes for a moment. I grabbed more of him and began the slow descent to his fat, hairy balls which his muscular thighs pushed upwards to meet the heel of my hand.

We were both too horned up, I suspect. Likely there had been some sexual tension between us for some time, and definitely there had been a little too much alcohol at dinner, and there we were as a result. Two work friends, horny in a hotel room, jerking each other off to porn.

My skin tingled, and my blood rushed, and I could smell both of us in the close space. Our breathing sped up, and the boss began to thrust himself hard into my hand. I followed suit.

“Gonna cum!” He blurted out, and a moment later I was treated to fireworks.

Now I’ve been with a few older fellows, and usually when they get off, it’s little more than a dribble. That’s not a complaint mind you, just the nature of things, so it blew my mind when this mature male in his fifties shot his first rope about three feet straight up! My eyes widened and I think I even said, ‘wow’ as it happened. He shot again, and again, liberally splattering his thighs and abdomen and covering my hand that still jerked him even as his body writhed and shuddered under my ministrations.

“Oh fuck, oh fuck.” He said hoarsely, almost whimpering, and a moment later I began to cum too. I gritted my teeth as my first shot erupted all the way to my chin, landing against my chest and beard. We pumped each other, almost automatically by that point, reveling in the other’s orgasm. For what felt like a full minute we each shivered and shot and slowly began to catch our breaths.

“Haven’t cummed like that in years!” Oscar announced.

“M-me neither.” I admitted and smiled.

“Damn, what a mess we made, ha!” He said, seemingly very proud of what we had done.

“I’ll go grab us a towel in a second.” I said, wanting to enjoy the comedown for a few precious moments more.

“You don’t need to towel all of it up.” Said Oscar as he brought the hand that had just jerked me off to his mouth.

My eyes widened as the boss stuck out his tongue and lapped the creamy white substance from his rough fingers. FUCK! Oscar Magnussen was eating my fucking cum, and I did not know where to file that information. It was the hottest thing I’d ever seen, even causing my deflating cock to half-heartedly rise again. However I also couldn’t help but notice the wedding band on his left hand, even as he sucked some of my seed from his thumb.

I felt conflicted again as the guilt settled into my stomach. It was worse than before.

“That was tasty. You want to try mine?”

He was still very much in a sex headspace, so I tried to hold onto that. I lifted my hand up to my mouth and dribbled some of the boss’ essence onto my tongue. Salty and thick.

“Yeah that’s it.” He growled, spurring me on.

I couldn’t lap up all of it though, there was a lot.

“You got some in your beard!” He pointed out and laughed. “Is that yours or mine?”

“Honestly not too sure.” I said.

“Here, let me get it.”

I didn’t expect him to suddenly roll onto his side and pull me towards him. My face was now very near to his as he actually sucked the cum from my beard whiskers. His large nose bumped against my lips. When he had finished, he remained close to where he had been, but now he was looking me in the eyes. His expression was still lustful, his eyes glassed over as he looked at me. He was so close that I could feel his breath on my face. He stayed there, and I began to feel intensely nervous. The way he looked at me, as close as he was, it felt far more intimate, more personal even than what we had just done.

“Oscar, I’m gonna go grab those--” I began.

He leaned in and closed his mouth over mine. His tongue invaded my mouth almost immediately. He moaned and moved his imposing body on top of me. I felt him grind his groin against mine as his lips kissed me roughly, but passionately. Apparently we had both gotten hard again. I felt his furry front press into me and one of his hands slid over my chest and began to play with a nipple. I groaned into his mouth too, but I, in spite of everything, I didn’t feel okay. This wasn’t how I ever imagined this going. His body working with mine felt good, but it didn’t feel right.

With some effort I pulled my mouth away from his. He took it as a sign to attack my neck and ear with eager sucking and nibbling.

“Oscar,” I began to say.

“Ohh Jim…” He responded.

“No, Oscar, stop!” I said finally and struggled to move out from under him. It was impossible of course, he had easily a hundred pounds or more of solid muscle on me.

His dark eyebrows knit together as he looked down at me. “What is it? Isn’t this what you’ve been wanting?”

“I, I don’t know. I guess, but not like this.”

He looked me deep in the eyes, and I looked away. He slowly rolled off of me and onto his back on the far side of the bed. Without a word he picked up the remote control from the bedside table and clicked the television off. He stared up at the ceiling fan in the nearly dark room. The only light came from the open bathroom door. Neither one of us said anything for several minutes. The cum on my front had dried by that point, but at least I’d be showering shortly. All of a sudden that had become the least of my worries though.

“Oscar?”

“Yes?” He said, after a few moments of silence.

“I think we just crossed that line you mentioned.”

“Yeah, it seems that way.”

“We probably shouldn’t have done that.”

“Little late for that now.” He said.

“Plus you’re married.” I added, as if it needed to be said.

“I’m well aware, Jim.”

More suffocating silence as I tried to think of something useful to say. I wasn’t sure there was a non-embarrassing way to explain that I wanted him all to myself, when he wasn’t somehow married. That I wanted nothing more than to be his man, for the rest of our lives, but not if it meant being ‘the other woman.’ I had too much self respect to settle for it being just a night of drunk hotel sex for my maybe not-so-straight boss on a fucking business trip.

“Are you gonna take that shower?” He asked finally, tugging me back to reality.

“Yeah I probably should. I went from sticky to crusty.”

“Well, when you’re done I need to take mine so, don’t take too long.”

“Understood.” I said and swung my legs over the side of the bed before getting up.

I looked over my shoulder and Oscar was still just lying there staring up at the ceiling.

“Hey uh, I don’t know what to make of all this.” I said.

Oscar Magnussen sighed as he turned his head to look at me. He frowned slightly. “This was a mistake. Just a drunken, stupid mistake. I’m sorry Jim.”

“I see.” Was all I said to that.

I proceeded into the washroom where apparently I had left the shower running the entire time we had been fooling around in the bedroom. I was still nude so I just stepped into the tub and felt the warm water begin to wash over me from overhead. There were too many thoughts swimming around my mind just then and I wished I could shut them out. I thought about working with Oscar after this, how it was going to be weird, how I wouldn’t know how to talk to him anymore. Would he fire me over this? Would he tell his wife what happened? I wanted to cry, but I also needed to hold it together. If I could have I would have stayed in there all night, away from the new awkwardness between us that had never existed before. But I reminded myself that Oscar still needed to clean himself of what we had done so I turned the faucet off and grabbed a towel.

“Shower’s free.” I said as I stepped back into the room, wearing my pajama bottoms.

“Great.” Said Oscar as he got up from the bed and walked past me. He didn’t even look my way, and I wondered if it was the shame of cheating, or the shame that it was with a man.

I went over to my bed, which was still made and peeled back the top covers. I got underneath them and set my phone alarm for the morning. It was already going to be a long drive back home, but with the way things were now, it was going to be excruciating.