A new thrill

Hey guys - just wanted to share a quick experience from this summer that I think you might enjoy. I always go to my parents house in SoCal for July 4th and then afterwards I take myself to Palm Springs for a few days before heading home to New Jersey.

I spent a week at home and then hopped my flight to PS last Thursday in time for a long weekend after the holiday which meant it was really slow. I always book the same AirBnB every time I visit and have come to know the owner pretty well. He will always meet up with me while I am in town at least once or twice for a drink. One of the reasons I keep going back to the same place is because the unit is a guest house / pool house with its own separate entrance and driveway on the side of the house. But the best part is that the pool between the houses is super nice with lots of landscaping and privacy. The owner ( I’ll leave out his name for privacy ) is probably in his late 50’s, muscled but thick, taller than me by about 5 inches and has a sort of biker daddy / corporate lawyer thing going on. 

A little background…every time I stay at this place I get a thrill from going out to the bars, have a few drinks, Uber back home and have one last drink by the pool before bed. The thing is I always have my drink and then slip out of my clothes and take a walk around the dark back yard before turning in for the night. I know it sounds silly - but it feels like a safe space…I ‘kind of’ know the guy in the main house and yet it’s still a thrill to think about the fact that I’m walking around naked with him asleep inside and there is a possibility of getting caught.

So anyway, nothing different on this trip. The host told me he would be in town while I was there and we should grab a drink…like normal. So I got in on Thursday night and hit up Toolshed for underwear night. I’m pretty fit so I enjoy showing off a bit. Over the years I have compiled a collection of underwear that I reserve exclusively for these nights. The pair I chose to take is a pair of boxers I’ve had forever. The elastic I stretched out so they ride really low on my hips and shows off the rope crack of my ass…and over the years the cotton has become super thin so you can see the outline of my dick.

So I hit the bar, checked my clothes and of course instantly made friends with some other guys from out of town that were really drunk. I stayed with them for a few drinks, we ventured out to the patio and watched a not so discreet handjob and say lots of skin around. The handjob was given to a very drunk and pretty handsome 20-something by a not very handsome older gentleman in a lot of leather. I think it was beer goggles. But we all took in the show because they were both pretty drunk and thought they were being sly under the table…problem was the table faced the crowd and the 20-something was standing between the wall and the older guy on a bar stool ( but his underwear were on the ground around one ankle.

Anyway…that isn’t the story. That is just the reason that when I headed home I was so horned up. So the Uber dropped me off on the side street and I entered the pool house gate to the yard. I could see the main house was dark and I zipped inside my unit to make a beer and grab my swim trunks. After I changed, I grabbed a towel and beer and head quietly out to the pool. I mentioned before that there is a lot of landscaping so I picked a lounge chair in a dark corner, tossed my towel on it and kicked off my flip flops. My dick was still semi hard from the evening show at the bar and the buzz from the drinks..so I hadn’t even made it half way through my beer before I decided to start pushing the boundaries. First I took a casual wander through the whole yard to make sure the main house was dark and the host was asleep. 

When all looked quiet I walked back to the side gate and slid my swimsuit to my ankles and stepped out of it. I picked it up and then started wandering back towards my pool chair casually sipping on my beer. Just the hot air on my body gave me a full hardon. I made it back to my chair and dropping my swimsuit on it and picked up my towel to drape around my neck. I figured I can always wrap it around my waist if the host happed to wake up for some reason.

I made another few circles through the yard and MAY have tugged my dick a few times in the process ..so I was super hard. I know this scenario is silly - but it’s one of the few places I get to enjoy being naked with a thrill but still safe. I also MAY have had a special gummy bear on the way home so that was kicking in too.

This is where I branched out from my normal visits. For some reason I was really feeling daring ( and horny) so I walked back to the side gate and opened it with only my towel around my neck. The side street and the streets around the house are pretty dark over all with some spaced out street lights. Most of the houses have walls in the front yards so overall it’s pretty quiet and private.

I stood in the gate and jerked for a few minutes and built up the courage to venture farther. I dared myself to prop open the gate and walk to the end of the drive way and back. So I pulled a rock out to the flower bed, propped open the gate and then walked out about 6 feet and stood there. Then I walked another 6 feet and another until I was at the end of the driveway about 20 feet from the open gate. My heart was pounding and I kept taking it a bit further and further. maybe it was the booze and weed gummy. Next I walked back to the gate and laid the towel on the ground and repeated my journey down the driveway totally naked and with a raging boner.

Then I decided to go a little further out of the drive way and along the neighbors wall to the next drive away and back. And then I made it two driveways down and back. It was like being a 21 again and feeling the thrill going to the bars the first time. So I kept pushing it until I worked my way up to the end of the block. If a car had driven by I would have been busted for sure. 

I made the full block trip a couple times and then decided to bump up the thrill a little more and I dared myself to close the gate with my towel inside, and then hide my key at one end of the block and then go the opposite way to the other end of the block and back. I can’t explain the rush, but it is what it is. So I did just that, the gate clicked closed and I darted to the end of the block and set my key on a landscape rock. Then I took off to the other end of the block crossing the street back and forth to avoid the street lights.

I made it to the end of the street, edged my dick for a few minutes and then headed back for my key. I made it to the end of the block and couldn’t find my key. Booze and weed is a bad combo for remembering something while you are horny and streaking.

I started to panic but remembered that the host had also given me a digital code for the gate at the front of the house. So decide to slip around the front of the house, go through the gate and slip around to the back yard.

The problem with my kink is that this scenario only made it more exciting. So I got to the front gate and stepped into the light over the gate…. and was frantically trying to remember the code and it just keep blinking red. I guess I was focused on the digital pad because all the sudden the whole front of the house lit up with headlights as a SUV pulled up infront of the house. I froze and like a deer in headlights and the car just  kept sitting there. I was racing to figure out how to explain myself when the back door opened and shut and the SUV drove away. It was the host! I guess he had been at a party and was jsut coming home. He was obviously a few drinks in and laughing as he realized it was me. I could tell he was taking it all in and I just decided to come clean and tell the truth. I’m sure I was bright red but the host listened as I told him about my night and my pool adventures. The whole time I could see him staring at my hard dick and that just made me harder. He was really giggling pretty good by the end of my story. I could tell my horny adventures were kind turning him on. He even reached up at one point and grabbed my hard dick pointing at him and said it looked like I was still having a good night. He lingered and tugged me a few times and let him. Hell, I would have probably let him jerk me off right there at the front gate. HE must have grasped the turn on for me because instead of letting me in the gate, he said, lets go find that key…show me where you lost it. Then he followed me back down the street to where I had lost the key. He was pretty flirty grabbing my dick a few more times on the walk and walking up close behind me as I was bent over looking in the dirt. 

He finally said, oh well, we will find it tomorrow. And looped his arm around my neck and headed back to the house, but he weaved out into the middle of the street so we were walking down the middle of the street back to the house. And then he didn’t go to the front gate he kept walking to the side gate. And then he didn’t stop at the side gate and kept walking. My heart started racing again and he asked if this was a turn on. I nervously said yes and that was all he needed to hear I guess because he just kept walking. I’m sure he knew the neighborhood well but my heart was in my throat…dick bobbing infront of me as he walked me through street light after street light deep into the neighborhood. We finally got to a little park like lookout over the city and he let me into another lamppost light by a bench where he left me standing and sat on the bench. Then he said he had seen porn like this and asked if the next step was that I jerked off for him. I could tell he was pushing to see if I would cave and I decided fuck it and went for it. 

So I did…I stood there in the lamplight and looked directly at him while I jerked out a load. Probably one the top ten orgasms of my life. BUT….as always the orgasm faded and post nut clarity struck. 

He didn’t waste any time after i came to stand up loop his arm around my neck and lead me back though the neighborhood with cum still dripping off my hand and dick.

Nothing else happened on that trip but I can not WAIT to go back. I really hope he sees this somehow so he knows I am up for more adventures !@