Giving Casey A Ride

As I stated in the first story about my drives between San Francisco and L.A., I would often masturbate along the way to pass the time. As things started to open up in 2021 and I received my vaccinations, I resumed flying to L.A. for my work trips most of the time.  However, my neighbor, Jack, thought I was still driving back and forth.  I saw him out in the yard one afternoon and he walked over and said hi, then made some small talk to see how I was doing.  I don't know him well, but we're always cordial when we see each other.  And, as I mentioned in the previous story, his son Casey is a really nice looking dude - I believe 26 or 27, good build, and a very cute bubble butt.  When the conversation turned to Casey, I perked up right away.  He mentioned that Casey has a job interview coming up in a couple of weeks in the L.A. area and asked if I'd mind giving him a ride if I'd be going that week.  I did have flights booked for the week in question, but didn't hesitate to say yes, I'd be happy to give him a ride.  So, I promptly canceled my ticket and set up arrangements to drive down with Casey.

The plan was for us to drive down on Tuesday, stay three nights, then drive back on Friday.  I had my hotel booked near the LA office downtown.  Casey was to stay with a former college friend in Santa Monica, so I'd drop him off and pick him up there.  Casey arrived right on time at 8:30am and we packed his stuff up in the car and hit the road.  As much as his dad was just a cordial acquaintance, I really didn't know Casey at all.  We'd just said hi several times in the yard, but I always admired how cute he is.  We had a lot of small talk for at least the first hour of the drive - our shared opinions on life during COVID, some sports (turns out we're both baseball fans), etc.  I then asked if he had a girlfriend and he said yes, Heather is her name.  I asked if she'd be moving to L.A. with him if he gets the job he'd be interviewing for and he confirmed that is the plan.  I'm sure his dad knows I'm gay, as I mostly had male friends over and certainly don't hide anything.  So I wasn't sure if Casey knew or not.  Then he asked the question if I was seeing anyone.  I said not at the moment, which he didn't probe any deeper on, so we continued on with light small talk.

Almost two hours into the drive Casey asked if I'd mind if he smoked a joint.  While I don't smoke marijuana, I have no problem with others doing so, but not in my car.  I told him I'd be happy to pull off somewhere if he really wanted to smoke.  At first he said no, then I said it's really no problem and I wouldn't mind stretching my legs.  He agree and I looked for an exit that was pretty remote where I knew there wouldn't be a lot of cars or people around.  There are a lot of those type exits along I-5.  Off we went and I found some type of orchard to park next to under some trees.  We got out and Casey lit up.  It was exciting being so close to him with no one around.  I wanted to direct the conversation back to him and his girlfriend's sex life to see if I could get him going, but held off  He offered me hits several times, but I just said I better not, since I'm driving.  He finished up and just as I was about to get back in the car, he said he needed to take a leak before we get back on the road.  Without much warning, he was unzipping his shorts and pulled out his cock to pee.  I tried to not be obvious, but I couldn't help but take a peek as I saw him rolling back his foreskin and starting his flow.  I thought 'awesome, he's uncut like me,' which is a turn on for me.  I wanted to get a good look at it, but only stole a few glances - but what I saw was gorgeous.  Pretty meaty for a soft cock and appeared to be a good four inches or so.  He finished up, zipped up, and we were back on our way.

I now had a semi growing in my shorts and was commando, like I usually am for my drives.  It wasn't long before my dick started leaking precum, which I was embarrassed he's see and freak out.  So, I positioned my arm to block the growing wet spot from his view.  Now that he was a little loose from his buzz, I had the courage to ask about his sex life.  I asked if Heather was good in bed and he said yes, but that she only likes to do it once or twice a week.  I said that's seems pretty odd for kids their age.  He laughed at the 'kids' comment, but when you're in your 40s, that's how it feels sometimes.  He said he agreed and wished she was a little more aggressive in that department.  I got up the courage once again to go for it and said 'do you save it up for her, or do you have someone else on the side, or just jack off a lot.'  He said he doesn't mess around, but yeah, he jacks off a lot.  That got my dick from semi to full mast and now leaking even more.  I was afraid I wouldn't be able to keep it hidden, but kept my arm strategically placed.  I asked how much is a lot and he said usually once or twice a day.  I said that's about the same for me, to which he seemed surprised.  He said, 'no offense, but I thought when you get into your 40s you lose some interest in sex.'  To which I said, I don't know about other guys, but I'm just as horny as I was when I was his age.  He said that's good to know.

I looked over and could swear I saw a bit larger of a bulge in his shorts, so I felt this was my chance to go for it. I said, 'in fact, I usually jack off in the car on this drive, which I'd probably be doing if I were alone.'  He said 'no shit, really?  Aren't you afraid of these truckers who can see right down into your car?'  I just told him if they want to look that bad, then it's their problem, not mine.  I pushed further saying there is something liberating about jacking while driving and asked if he'd ever done it.  To my surprise, he said he doesn't drive.  I forget this generation isn't crazy about driving themselves, apparently.  I said it would be tough to jack while driving if you're always with someone else doing the driving.  He agreed.  Since this was an opportunity like no other, I said 'unless the driver is jacking too, I guess.'  He chuckled, but didn't say anything.  I decided to go for it and said, 'hey dude, all this talk has me pretty boned up.  I could really use a release.  I certainly won't if it'll make you uncomfortable, but would you mind if I take care of it?'  He hesitated, then said, 'hey, it's your car and you're doing me a favor, so I'm cool if you want to.'  I said he could join me if he'd like and let him know I could see a large bulge in his shorts.  He said, 'no I'm good, thanks.'

So, I was faced with a dilemma.  Do I go ahead and jack right there next to him while he seems a little uncomfortable, or tell him I'll just hold off?  I said if he's not truly cool with it, I can hold off.  He said, 'no, I'm good - you can go ahead and take care of it.'  So, I moved my arm so my precum soaked short and hard cock within them were in plain view as I started to unbutton my shorts.  I couldn't see him looking over at all, but I continued and unzipped my shorts, then stuck my hand in to feel my warm, pulsating cock.  It was then a saw him look over and he said 'holy shit man, did you just cum in your shorts?'  I said no, I just precum a lot and my dick started leaking when I got hard.  He said 'I precum a bit, but not like that.  It totally looks like you came in your shorts.'  I was now as hard as I think I've ever been and started to push my shorts down and release my six inch cock.  I pulled it out and started slowing stroking, my foreskin exposing the rock hard tip as it flowed up and down.  Precum was the full length of my dick now and I said 'see, it's just precum making all that mess.'  

I asked if he was sure he didn't want to rub one out, as well, as I was more direct this time in pointing out his now pretty full bulge.  He said it's a little weird, but he could stand to take care of it he guessed.  I encouraged him to go ahead.  After another minute or two of him seeing me stroking, he unbuttoned his fly and unzipped his shorts, but opened them just enough to see his boxers.  He slid his hand in and began stoking under his boxers.  I told him it feels much more invigorating to let it and jack in the open air.  He hesitated, but within another minute or so he pulled to top of his boxers down and unleashed his beautiful uncut cock.  Looked to be about the same length as mine, but a little thicker.  It was amazing!  After seeing that, I lifted my butt off the seat and pulled my shorts down to my knees, exposing the full package with my balls shaking up and down with each stroke.  I told him this is the way you really feel free when jacking on a drive.  He didn't say anything, but I was him lift up and within a few seconds that fantastic bubble butt was bare ass on my passenger seat with his shorts and boxers around his ankles.  Oh my god, what an amazing site!  

I could see precum oozing out of his cock, so I commented that he clearly precums more than just a bit.  He said 'yeah, this is more than usual.'  I was out of my mind at this point and told him it's more distracting doing this with someone else, but I'm kind of liking it.  I said it would probably be better to find another secluded area like where he had his joint so we can finish.  He didn't object, so I soon pulled off and found a similar orchard with no one around.  I pulled off under a tree again and we both sat there jacking for a few minutes.  I felt like I was about to explode and said, 'hey, so we don't make a mess of my car, how about we finish up outside.'  I didn't really care about the car, but I wanted to see if I could get him out of the car to see that bubble butt in full glory.  I opened up my door and shucked my shorts on the floor so that I was now only wearing a t-shirt.  I stepped out and went around to the passenger side, away from the road. My dick had a flow of precum streaming down and I shouted for him to step out and finish up.  

The passenger door opened and he stepped out, now also only in a t-shirt.  As he got out I was transfixed on his beautiful butt.  It was like it was sculpted to perfection.  Very slight fuzz on it and very tight.  I mentioned that our dicks are a pretty even match and he said 'yeah, guess so' as we both continued stroking.  I moved a little closer and kid of faced him, then said 'you got me beat on girth though.'  Standing there, just a few feet from him, watching his hand glide up and down his beautiful cock, balls bouncing, foreskin exposing then covering his pink head put me over the edge.  My cock exploded in one of my biggest ejaculations in years!  It shot further than usual as I was so turned on and barely missed hitting his foot.  As he saw me shoot, he then let out a grunt, stood up on this tiptoes and started shooting a massive load.  At least seven or eight ropes of cum and, to my delight, the first shot him my thigh!  As he finished his eruption, he leaned his head back and didn't say anything.  With head back and eyes closed, I took the opportunity to wipe his cum from my thigh and lick it down. It tasted so good!

As both our cocks started to deflate, I told him I have some napkins in the glove box we can use to clean up.  I moved past him, getting a close up look at his adorable butt.  I leaned in and opened the glove box, noticing that I never had taken out my precum soaked mask from a year ago.  I'd have to put that back on when I got to L.A. to see how it's held up.  I handed him some napkins and we both dried off our now semi hard dicks.  We put our shorts back on, mine still soaked with precum, and finished up the drive.  I told him I appreciated him being cool with me getting off along the way and he said he could really see how that helps pass the time on this boring drive.  After that, we really didn't talk about what happened.  I dropped him off in Santa Monica, as planned, and told him I'd see him Friday for the drive back.  While he seemed pretty cool with our J.O. session, I then got a text on Thursday saying his plans had changed and he'd be staying a few more days.  I said I could push my stay back to give him a ride back, but he declined and said the interview went well and they want to see him again Monday and they agreed to pay for the flight back if he could stay.  Then he texted for me to 'enjoy that drive as you cum back to SF' and included a winking emoji.  So, at least he was light hearted about it, even if he may not have wanted to do it again.  

This was about six weeks ago.  I saw his dad if he'd gotten the job and he said yes - that he and his girlfriend would be moving to L.A. in September.  I haven't see Casey over since, but his dad said they'd be having a going away party for them before they leave and I would be more than welcome to attend.  That will be this coming weekend and I'm nervous about going.  I asked Jack to be sure Casey wouldn't mind, since we really only know each other from one drive to L.A.  He said Casey was the one who asked him to see if I'd want to join, so I'll be going, but still very nervous about it.  In the meantime, I have jacked off every day to this amazing memory and hard as a rock now as I write this.  I guess it's time for my next j.o. with Casey's butt and cock in mind.