Jack's office fling

 

I met Jack online, he is a few years younger than I, but at first I thought he was a younger man, looking for a Daddy.  I initially I kept my distance.  After he made a certain comment, I said to him that he only thought that way since he was so young.  He asked me how old I thought he was.  When I told him, mid 20s, he laughed and said his age, which was 3 years younger than I am.

After that, our conversations changed in tone and context.  He’s divorced, has  children (grown) but is currently single and has been for some time.  He runs his own company, which despite the pandemic is doing well.  We began to flirt, to discuss sexual fantasies.

Jack confessed that while he’d thought about being with a man, he’d never actually been with one yet and had only dated women.  He had had toys used on his ass and had been pegged by one girlfriend.  That’s what got him thinking about being with a man.

We continued to chat for some time. I had mad an assumption on where he was located, based on his late-night posts, I decided he must be a west coast resident and US based, as well.  When he suggested that we meet, I asked him how he thought we could do that, given the geographical challenges. 

He informed that he lived in Scarborough (the same borough of Toronto that I live in) and we deduced that we’re about 10 minutes away from each other.

I agreed to meet him for coffee at a local mall – everything is still closed due to the pandemic but coffee shops are deemed necessities so they’re open.  I walked, he drove. And on a Saturday morning we met for coffee. Took it to go, the only option, and sat in his car.

We sat and chatted, getting to know each other.  He’s very cute, about the same height as I am at 5’8”, nice build, not overly muscular, but not gone to pot either.  He was wearing a hoodie, a tee and sweatpants, over a pair of jogging shoes. As we talked I noticed movement in his sweat pants.  I’d seen a pic of his cock, it has a narrow shaft and a bulbous mushroom head that flairs out.  Someone getting fucked by that would feel it going in.  Without asking, as we talked, I reached over and slid my hand into his sweats and clasped onto his semi-hard cock.  No underwear. 

He moaned immediately, and uttered an “oh my god” and I traced that big head with my fingertips.

Taking his coffee and putting it in the drink holder, I reached over and took his hand and brought to my own cock.  I was wearing jeans so it wasn’t as easy for him to access it. But together we managed to get my cock out.  He stroked it a few times and then I told him to suck it.  We had discussed that he needed guidance, someone to tell him what to do, so I was taking that roll.

He tried to bend over but was knocking the coffees and he couldn’t quite reach.

Just as he sat back up, someone walked by the car, which spooked him.  Without asking he started the engine and pulled out.  I asked him what he had in mind.  He said “Let’s go to my office – it’s about 5 minutes from here and we’ll have privacy.”

He pulled up to a single-story industrial unit, the kind with offices in the front, plant in the back.  And we got out of the car…His cock was still out, I asked him to leave it out.  He was nervous but did as I asked.  He unlocked the front door, shut off the alarm and we headed into his office.  I walked close behind him and reached around to grasp is cock.  He stopped as I closed the gap between us and stroked him, and bit gently on the back of his neck.

He leaned back into me, pressing his ass into my crotch and my hard cock. His head tilted back, and I leaned forward and kissed him. He turned and I embraced him pulling him tight trapping his hard cock between us and our tongues danced.  I bit his lower lip as I pulled away.

He gasped.  “I never imagined..” he started, I kissed him again and simply said, “where?”

Reluctantly, he let go and grabbed my belt pulling me along as he led the way to his office.

His office door is laminated in a shiny material, so shiny, it’s virtually a mirror – a foggy one but reflective, none-the-less.  As we entered his office and closed the door behind us, I took him again and this time pressed him into the door, kissing him and running my hands over his body.  The nice thing about sweat pants is how easy they are to remove.  And pushing down, they simply fell to pool at his ankles.

Stopping the kiss for a second, I pull the tee up and over his head and he’s virtually naked before me.  I return to kissing him and bite my way down to nibble on his nipples.  “Fuck” I hear him say.

His cock is bouncing against my leg and looking down and I see a wet spot on my jeans from his pre-cum dripping from that big head.  I reach down and stroke him again, sliding my hand along his narrow shaft and up and around that big thick head.  All together about 6 very solid inches. Nice balls, smallish but a good handful.

“You owe me a blow job”, I tell him.  And push him down to his knees.  He unbuckles my jeans and slides them down, revealing the fact that I’m commando under them, my hard cock slaps him the face.  He dives onto my cock, trying for the base.  And instantly gags.

“Slowly”, I tell him, and I hold his head still and slowly fuck his mouth to set a pace and depth for him.  Once I think he’s got it, I let him take control of his pace. And he’s fucking me with his mouth.  I’m watching the muddy reflection and I can see us, him bouncing his head on my cock, my hand resting on his head but not guiding.

He’s a rookie but he’s doing a good job and I’m forced to stop him before I shoot.

Standing him up, I ask him if he thinks he’s ready to be fucked, to finally take a real cock?  He says he is.

So I flip him around, and press him into that reflective door, I drop down and rim his ass, and slide one, two, three fingers into him.  They go in easily, he doesn’t resist at all, so I know we’re really ready.  I stand up and he’s leaning to the door, hands supporting his weight, looking into the reflection, looking at me.

I step forward and my cock head presses into his ass.  He asked me to fuck him raw, he wanted to feel a cock and a load in his ass. I comply and raw, my cock presses into his ass. I have to bend him slightly to get the right angle.  He eyes never leave me in the reflection.

He’s anxious and pushes back, just as I push forward. My head pierces him.  He gasps, and he tightens around me and I think maybe he wasn’t as ready as I thought. But the clamping tightness eases in a moment and I’m able to begin to slide into him. It doesn’t take long until I’m buried balls deep (being only 6 inches has its advantages).

I hold my position and pulling him up a bit and leaning over his body, I nibble the back of his neck.  I hear a sigh, and his body relaxes into mine and I know he’s ready now to be fucked, not just penetrated.

I start slow, building a rhythm and increasing the tempo.  Fucking him balls deep, fully out, then back in balls deep.  I start to slam into him, the hard slap of flesh against flesh is filling his office. I continue to bite his neck, his shoulder, his ear lobes, I reach around and stroke his cock.  I can’t keep time to my thrusting, and I don’t even try.  Instead, I pump and clasp his cock, my hand covering the shaft, leaving only the head exposed.  I slide up and down, over that sensitive head, back down, back up.  He starts to groan loudly and I know he’s close, I pick up my pace and really start to fuck him hard.  I want us to come together.

With a loud moan, he blasts that shiny door, 4, 5 6 pulses jet from his cock head and paints that door, streaming down towards the floor. I feel his cock pulsing in my hand.  By the third pulse, I’m filling his ass with my load.  When I’m done, I let his cock go, and step back, away from him, pulling my cock out of his ass.  He collapses to his knees and folds at the waist, catching his breath.

“Holy shit” he says, “that was so fucking amazing”.

Reaching over him to the door, I scoop up a finger full of his load and insert that finger into his mouth.  He tries to turn away but I force the issue and he’s soon licking my finger clean.  We’re both on the floor now, pants still around our ankles, he’s shirtless and sweaty.

Outside the door, instead of a quiet, empty office we hear music playing and the sound of the copier running – it’s next to his office.  And we know we’re not alone.  The office fuck was his fantasy, we’d talked about it – I didn’t expect to do it today but he had insisted that when we did, we’d have to do it when the office was empty.  It looks like someone else came in, however, while we were busy.

He cleans up his door. Smudges remain, leaving a visible tracking of his load as it ran down the door.

We pull our clothes up and put ourselves together, so we look presentable.   And we head out of his office, bracing to see someone there.  However, we don’t see whoever it was that was in that office on that weekend day but he does recognize the car in the lot.  He’s going to have to say something to her on Monday. He says he can’t face her today, but he’ll feel her out to see if she heard anything.

Instead, we head back to his place and fuck again and again.  For two old guys, our libidos are working overtime.