Jogging Quickie

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A neighborhood jog leads to first time magic.
6.5k words
4.7
156.2k
369

Part 1 of the 2 part series

Updated 06/10/2023
Created 12/20/2020
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Okay, so here is my setup.

I'm a good-looking, 25-year-old guy, who got married a couple of years before the quarantine began. I've been told I have sort of a Nick Robinson kind of look, the younger actor.

My wife is great, but we see each other every fucking day. 24/7. And soon to be 365. We had both been working from home during the quarantine, but I've just had my hours cut down to three days a week, which leaves me with even MORE time to twiddle my thumbs in perpetuity.

We've had about all the kinds of sex during our lockdown that she's comfortable with, and honestly, I've gotten insanely bored lately. Like...bored all the damn time. And horny. Horny and bored--the worst combination. I feel like I've gone through every single Pornhub category lately just out of sheer boredom-induced curiosity. Categories I would've NEVER watched in a non-pandemic world. I even wandered over into some bisexual content the other night. It wasn't half-bad. I found myself strangely looking at cocks more often when I would watch porn. I needed the cock to look nice for some reason. Not just the girl. That was peculiar. Fucking COVID thoughts. I swear. Ridiculous.

I started going on these long runs through my neighborhood to let off steam during the day. I can't always jack off easily due to the size of our condo and bathroom, so a lot of times I end up stuffing my constantly half-hard dick into my tight jogging shorts and heading out into the chilly fall weather to spring around the changing tree colors and smell the many fireplaces.

Our neighborhood is full of old Craftsman style homes in a suburb just on the edge of Seattle. There are a lot of well-off people that live out here. Tesla's and Audi's and wraparound porches and in-ground jacuzzi's, and so many other things told the biotech-bubble tale. There were a lot of movers and shakers living in this area that was for sure. I would often try to imagine what type of sex they were all having.

There is this one house that I always slow down by to admire a mile into my run. Faded red brick bleeding into a sort've modern black-and-gray facade. It somehow manages to look like a rustic and modern house all at once. The gray paint is smartly lined with black outlines and the chimney re-emerges with the stark red brick. The backyard has a basketball court, a jacuzzi on a raised deck, and even a pool. It's really quite something.

Today when I run by it, I pause a moment longer than usual and a taller man steps out of the garage of the house, which I hadn't yet realized was open.

"Hey there," he says, seeing me admiring his house. "Pretty amazing place isn't it?"

"Oh, hi! I'm sorry, didn't mean to seem weird, I always obsess over this house." I quickly say, feeling bad for having been caught. I'm very stoned, I should make that clear.

"Oh, please, it's really no big deal. People stop and stare all the time while they're on walks or jogs or whatever. That's kind of the nature of living in this neighborhood...lots of house-watching." He is immediately so nice and easy to talk to.

"Oh...gotcha. Well, yeah, it's an amazing house. Is it yours?" I ask, almost forgetting how to do small talk in that moment. There is an immediate presence to this man that is inescapable. He is 6'3 and looks like a slightly older version of the lawyer from that show JAG--all square jawed and perfectly-coifed hair, though tinted by a recently spilt salt and pepper shaker hue. He's also built. The kind of muscles I could probably develop if I paid more attention to weights and less to cardio. I certainly have the time. All that bored time. Sigh.

"It is, well...mine and my wife's. We bought it a couple years ago and have been adding some design features we really love every few months," He was wearing a pair of old gym shorts and a tank top and some expensive slippers, and that about was it. He'd been tinkering on something in the garage.

"That's great. I really love it." I don't know why I hadn't kept jogging, there was just something so magnetically interesting about this older, fit man that I found myself all of sudden talking to.

"Would you wanna see what the inside looks like? It's really incredible," he offered, and it seemed innocent enough. And why not? I had nothing else but time these days.

I probably should've been a little suspicious of his motives...but my brain had started to turn off from quarantine and I would get very stoned right before I went on my runs, because I found that I ran harder and I sweat more. I reached that endorphin fix I was looking for to coddle my unrequited desires of constant horniness.

"Sure! Why not," I finally decided. I honestly would've done anything for a good distraction or change in my routine at that point.

"I'm Roland by the way," he extended his large-fingered hand and we shook. He was warm to the touch. He was bigger than me. More towering than me. I looked up at him when I spoke.

"I'm Preston," I responded, and I smiled at him. I felt funny.

"Great to meet you Preston, come on in."

We passed some sort of black fabric with hooks, that was draped over a Craftsman work bench, and on through a door which led into the sprawling house. I passed his vintage sports car on the way which was also being worked on, and then was immediately swept up in the soft wood and earthen tones of the interior design. I felt like I had walked into a Restoration Hardware-meets-hunting lodge wet dream. Everything felt like it was fresh off an episode of some mind-soothing, Flip-This-House show.

He gave me the grand tour of the downstairs area, which included his weight room and sauna. His sauna was a four person sauna. Not too big, but still, how fucking cool to have a sauna in your house? He showed me the backyard, with the impressive swimming pool and spa and basketball court. He showed me the well-stocked kitchen with impressive fridge and island and bar stool area. That bled into an amazing lowered living room area with a large wraparound couch and trunk table and chairs and a huge 90 inch TV well placed in between two large floor to ceiling book cases. Jeez, what a great spot for TV or, honestly sex.

"Is your wife home?" I asked, as he showed off a bar he was very proud of in an adjoining wing with tons of incredible aged Scotch's and rare Tequilas.

"No, she works until 6 on weekdays and her office is still going into work. I mostly have my days to myself and my work is stocks so I make my own hours. What about you? Do you live with a wife or a girlfriend?" He asked, as we continued on down a hall. I didn't know why I was even in here but the house was incredible and he was such an alluring tour guide. He was clearly very proud of his home and things--I guessed he was probably in his early forties, but he looked incredible for his age. There was a small amount of sweat on his body from when he'd been working. I could smell him I thought. It was very present.

"I do...a wife. We have a condo together about a mile away...we both work from home currently." I said, and my voice drifted off as I said it, and he could sense my restlessness. I was also quite stoned, and always got more honest when I was stoned. Also I'd been running very hard right before I stopped at his house, so my blood was still pumping. It was pumping harder now, even.

"Oh, yeah...that's sounds cramped," he said, and his hands filled the large pockets of his gym shorts. His legs were very toned and had a pretty normal amount of hair. Why was I checking out his legs, though?

"Yeah...ha...it can be," I agreed. I wondered if he'd noticed where my eyes were. They darted away awkwardly.

"Do you want to see the upstairs, it's just as impressive." he asked now, and I still hadn't caught on to where this was going. Indica will knock you out.

"Uhh, yeah, totally." I readily agreed to the idea. I did want to see it.

He led me up the hanging woooden stairs that curved once, and I watched the way his muscular calves moved on the stairs in front of me. I'd never done anything with a guy before but if I was ever going to dip my toes into that pool he's probably the type of manly man I'd go for. Why was I even thinking about that?

He showed me their guest bedrooms and then opened up two doors to a master bedroom that was more impressive than any I'd ever seen. It led out onto a huge balcony that overlooked the amazing backyard which was also connected to a bathroom that similarly had a door leading out to said balcony; with a huge, jetted tub and rain shower and every possible feature imaginable.

He watched me checking out the sheer size of the room, and admiring the king-sized bed which was centered in the space. Brown and olive and burgundy bedding luxuriated before me. Martha Stewart-post jail term had been here.

"What a fucking setup!" I said, almost in jealous shock of the place.

I found myself standing at the very foot of the bed, taking in its size.

"Isn't it incredible?" He said, and I noticed he was standing closer behind me now, though not necessarily touching me.

I gulped breathlessly all of a sudden. I think I realized at that exact moment that he was into me...and that this wasn't in any way just an innocent sort of interaction.

I suddenly felt my entire body shake nervously...I'd never done anything with a guy, and had never had any intention of it.

"Shhh. It's okay." He said, and I felt him step up behind me and press himself against me. My legs pushed against his bed.

I was having trouble breathing I was so nervous. My cock was throbbing hard in my tight running shorts. I wasn't wearing underwear because they were built in to the track shorts.

His musky scent invaded my nose. He smelled like pine or...I dunno...some sort of flavored cigar.

I could feel his hard-on through his shorts as he pressed against my ass. His hands came up around my torso to hold my chest gently.

I breathed scared breaths out in front of me, like I was naked in an ice cave. My heart pinballed around inside my chest and the Butterfly Effect began in my stomach in earnest (the fucked up movie).

"Ummm..." I began to protest. Here was my one chance. "I don't think I wan..." I began to pull away, but then his soft lifts were on my neck.

He was kissing me.

Fuck.

He was kissing my neck.

And I likd it.

His muscled arms and chest felt strong against me. His cock felt big against me.

"Mmmm..." I moaned softly in the quiet room. I could hear a bird squawking and car driving by outside.

I could hear a million things all at once.

I was moaning for him. I was grinding against him.

He brought a hand down to my waist and began to stroke the top of my ass.

I liked that.

He kissed my chin and my ear. He kissed my cheek. He pulled my mouth to his and kissed him. He shoved his tongue into my mouth and I moaned from that. He forced me to french kiss him and I really, really moaned from that.

Then he was pulling my shorts off with his hand and he was pulling his shorts off right after.

He pressed his freed cock against me. He was big. I didn't know how big but I knew he was big. Bigger than me, and I didn't get complaints.

I was so nervous and turned on and excited.

He pushed me down suddenly so I was laying with my chest on the bed. My ass was exposed to him.

He went to grab something from his dresser and was quickly back behind me. I scrunched my arms in and bit my lip with an insane sort of crazy horniness I couldn't seem to slow down. I arched my ass back. A cold liquid poured down my crack and covered my virgin opening.

I had never wanted anything up my ass. But he was doing something naughty to me. He was bending me over right away. I was doing something stupidly fucking dirty and I wasn't even being given the time to overthink it or decide.

I was bent over on a king-sized luxury bed in the house of a sexy older man, and he was about to shove his...

"UNNNFFFFFFFFFFFFF!"

The thick helmet crested my tight anus and my sphincter tore a little to allow him inside of me. If ever there was a cherry to be taken, he had taken it.

I immediately screamed a little. It was a sexy scream though. I couldn't believe how sexy the noise sounded. I wanted him out. It hurt badly. I thought I was gonna maybe cry for a second it hurt so much.

"Shhhh...just trust me...you need to wait a second. I'll make this very good for you." He said, in his smooth baritone.

I did wait. I winced. I winced some more.

I wanted to stop, but also.

I had a cock in my ass.

Whoa.

I never would've imagined.

Whoa, whoa, whoa.

I was, no matter the pain, SO. FUCKING. HARD.

And soon, I didn't want to scream any more. More lube spilled into my ass, and his shaft began to slowly push into me.

I moaned for him.

I looked back at him and I moaned for him.

"Yeah. That's a good boy." He finally said.

And I realized that was exactly what this was. And why it was so hot to me.

I immediately understood that I wanted some kind of instruction or...I dunno...some guidance during this fuckshow of a year.

I spread my ass cheeks for him.

His four inches inside of me soon became five. And then six and seven.

I was moaning and feeling my ass open for the first time.

It hurt, and it also felt really fucking good.

"You like that cock, Preston?" I almost laughed because I didn't know if he was saying my name...or if I liked it pressed in.

"Yes," was the answer to both.

And then the eighth inch finished off my virginity.

He fucked me for the next five minutes. It was slow and sexy and I was so tight around his shaft that he already loved everything about my ass.

"I'm gonna cum in your ass, Preston." He said firmly to me, and I rocked myself back for him and moaned at how much I wanted him to.

"Cum for me...fuck...cum for me..." I moaned, not even believing they were my words.

"I'm going to cum for you, I'm gonna breed this naughty ass," he said.

And my brain couldn't grasp what it was like to hear those words.

He fucked me a little harder and soon his cock was exploding inside my ass as he pounded me into the bedsheets and i gripped hard to the bedspread.

I was practically crying from how good he felt against my prostate.

After he'd cum he flipped me over with his cock still inside me and began to jack me off.

I lasted only thirty seconds as he rocked himself into me and touched me just right.

I jizzed all over myself and it flew as far as my chin. I couldn't believe how fucking good it felt.

It was all over with ten minutes of having started.

I had just had sex with a man for the first time in my life.

"I, uhhh...I gotta get going," I said...suddenly very embarrassed and not really at all as horny as I had previously been.

"Of course," he said, seeming to understand.

I didn't even stop to use the bathroom. I said goodbye to him at his front door.

"Ummm, thanks for showing me the house," I joked awkwardly, not sure how I was feeling.

"Preston..." he started matter-of-factly, "if you ever want to stop by during the day, I'll take care of you." I gulped and looked nervously at my feet as he spoke, "I'll fuck your ass, and I'll teach you how to suck cock. And I'll make you my slutty little boy. And that's the dynamic we can have, and you can stop or leave whenever you want. Okay?" There was such an easy confidence to everything he said.

"Ummm...yeah, I don't know. I'll think about it," I said.

"Totally...no worries either way. Maybe it was just a one time thing. Maybe you'll totally forget about me," he said, and we locked eyes one last time. He was just barely smiling.

We shook hands and I headed off to go on my run.

My body was so wildly confused that I simply ran as hard as I could. I ran for three more miles, completing a loop that would bring me back home.

My wife was still completing some work calls. It would be another hour before she came out of the bedroom where she buried beneath her laptop.

I quickly grabbed a water bottle and went to the bathroom. I didn't turn the light on...I just used the late-afternoon light that streamed through the window.

I squatted over the toilet and was amazed to feel how much squishy juice dumped from my very opened ass. I was sore already.

I took a while on the toilet and cleaned myself out the best I could. He had cum so much inside me and I couldn't tell if I thought that was gross.

Then I turned on a very hot shower and stepped in. I just stood there for a while, in the silent acoustics of the bathroom, letting the water hit my back and run down my ass.

I had just been fucked.

Fuck. It felt so damn weird.

And yet...

I began to soap up my body and there was a strangely good feeling that was still running over my body. It was confusing and new.

My wife and I had our typical night together that night and she fell asleep earlier than me, as we finished off another season of Shameless and she announced having work early and giving me a kiss before prodding off. I felt a little guilty. I'd never cheated until today.

I was in our living room browsing trash TV, and I absentmindedly found my mind replaying the scene from earlier, over and over again.

I couldn't stop thinking about it.

I was getting hard thinking of it.

I took my cock out of my sweats, and closed my eyes.

I thought about how he bent me over.

I touched myself softly. Slowly. I took my time.

I thought about how it felt. I thought about how nervous and excited he made me. His presence. His feel. His cock.

I thought about his cock a lot.

And soon I was cumming all over myself. The memory was like instant sexual fantasy lava.

I couldn't believe how hard I was cumming again, all from fantasizing about Roland's huge dick.

And the way it slid inside me. The way he held me to him. The way he opened me up. I thought about his cock fucking me in slow motion as I came.

I even moaned lightly to myself. It turned me on to hear myself moaning. It was dangerous. It was unexpected.

Fuck.

I went to bed after cleaning myself up with a paper towel.

And then, for that next week...I tried to stop thinking about it. I tried to convince myself that it was a one time thing, and I definitely didn't need to dip my toe further into that very bad behavior.

I went on three runs, each time choosing a slightly different route.

But then my wife was going away to see her Mom for an upcoming weekend. She was apart of her very small quaranteam.

And it was the middle of that Friday that I decided to get very stoned, knowing I had the house to myself for the next two days.

I eyed my runners peaking out at me from our coat room that stood by our front door.

I took another long hit off of my weed pen and quickly got some running shorts and a shirt and a sweater, because it was a little chilly outside now, and I started my run.

I was nervous as hell.

I wondered which route I would take when I neared a mile. Would I head downtown...or towards the fancier houses?

My feet didn't even give me a choice. After about 8 very fast minutes of running, I pulled up in front of the midday shine of the sprawling property.

His garage was closed this time and I was almost disappointed, but after standing for about thirty seconds wondering if should do something, I laughed at myself, and I began to run away.

"PRESTON!" I heard a deep voice call for me. I was about 20 yards away from the house. He had just seen me from his window.

I stopped and ran slowly back. I was so nervous.

"Hey..." I said with silly smile, approaching, not sure what to say. I was very stoned again. I'd taken a bigger hit than usual.

"It's great to see you! Would you like to come inside?" He asked so simply. No fucking around.

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