Last Night in Paradise

This story took place on our last night in San Juan, and it was a great end to the most romantic trip of our lives. For Christmas, I surprised my girlfriend Lily with plane tickets to Puerto Rico where we spent a week hanging out in a beautiful beachfront condo.

We spent most of the week smoking weed at the beach, doing excursions, eating delicious food and fucking all over every square inch of our oceanfront suite. Being young and in love with a white sand beach and crystal blue waters as our backdrop made for an unforgettable vacation. Even though this story is now several years old, I still remember the details as if they happened yesterday.

We started our last night in San Juan with dinner and drinks at La Placita, the local market area that turns into a large street party after dark. This place was as fun and lively as all the locals had told us it would be. There were beautiful Latin women flooding the streets dancing to both the live local music being played masterfully by skilled musicians on the corners and the pop hits being blasted out of the bars that were scattered around the square. I'd be lying if I didn't say that occasionally taking glimpses of some of the heavenly booties that littered the streets.

It was a very cool experience because most bars encouraged you to get out and explore, pouring your drinks in disposable cups so the party literally poured out into the streets as people wandered the area while drinking and dancing. We had a great time getting high and drunk after our delicious dinner of local delicacies. We danced the night away as we hopped from one bar to another, making out like college kids who couldn't be bothered to find any privacy for our intimacy.

Lily looked particularly beautiful on the epic evening. She's a 5'3" Asian spinner with a tight ass, a mesmerizing smile and beautiful brown eyes and great tattoos decorating her gorgeous body. Even more beautiful than her physical appearance is her give no fucks attitude. She says and does what she wants, when she wants and doesn't care who it offends. She's the most genuine human being I've ever met, which is one of the reasons I fell in love with her.

She was wearing a skin tight black mini dress that hugged her modest curves and felt particularly good as she rubbed up against me while we danced to the beats that filled the streets. Eventually it started to feel a little too good and I started regretting the decision to wear skinny jeans on this hot and sticky Caribbean night.

I was now faced with a dilemma of sorts. Dancing with my beautiful girlfriend was giving me a massive erection that my pants were not designed to contain and if I stopped dancing with her it would be plainly evident that I was sporting a world class hard-on in the middle of this street party. So I did the only thing that seemed logical to me at the time, burst into a full on PDA in front of countless strangers as we made our way towards a more secluded destination for the culmination of our final night in this island paradise.

After getting our hands on some street grilled chicken skewers (the aromas distracted us momentarily), we found an area where we could pick up an Uber (luckily the area had free Wi-Fi) and headed back towards our condo. I put my arm around Lily and held her tight as she lay her head on my shoulder as we reflected on our wonderful evening. The arm that wasn't around her shoulder I began to use to rub her pussy over her soaking wet panties. She had both of her tiny hands in my lap gently rubbing on my ever expanding dickprint as we drove through the moonlit streets.

Then I made the decision that changed the night. As we prepared to turn down the street that led to our final destination, I asked the driver to go straight and drop us off at the entrance to the beach. Sometimes my inner romantic and inner pervert work harmoniously together to think of a clever idea. We were going to take a romantic walk down the beach and I was going to find a secluded spot where we could fuck.

As we walked down the beach it was almost as empty as I would've hoped but there were still about a dozen couples who had chosen to end their night laying in the sand as the seabreeze soothed their souls. We walked along the beach searching for a secluded spot where we could enjoy the ambience with a little bit of privacy. We found our spot at the back of a restaurant we had visited a few days earlier.

There was a bench facing the ocean that looked like it was used by the staff when they were taking breaks. Being up against a building shielded us from anyone being able to walk up behind us and see what we were getting up to without walking down the stairs which would give us time to escape if necessary. I sat on the bench and she sat on my lap. We started making out immediately. Our kissing was now even more desperate and full of passion.

My body refused to wait any longer to be inside her and it felt like I was about to tear through my jeans like the Hulk. She got the hint and started grinding on my bulge clearly enjoying my struggle before finally taking the initiative and releasing my monster from its confines. You could see the pre-cum leaking from my cock in the moonlight as it was finally revealed and a devilish grin that had crept across Lily's face.

She turned around so her back was facing me, lifted her skirt pulling her panties to the side and slowly lowered herself onto my rigid rod. A hushed moan escaped her lips as her body betrayed her while she tried to silently slide down onto my shaft. She was only able to take a couple inches on her first attempt but her persistence paid off and she leaked all over my now slick shaft and bounced up and down with greater ease on each stroke. Our breathing intensified with her movement but she was able to stifle her moans with the help of my hand.

While we were fairly sheltered from the rear, but it would have been pretty obvious to anyone who looked back at us from the beach what we were up to, so it was important to avoid catching anyone's attention. The thrill of getting caught made this endeavor all the more exhilarating. I knew I wasn't going to last long as she was now bouncing up and down on my thick cock, taking me from tip to base on every stroke. I could tell from the way her pussy was contracting around me that she was nearing her climax as well so I did what I could to hold off my impending explosion until she could join me in the land of orgasmic bliss. I had my hands around her hips helping to control her pace and force as much of myself into her as I could without alerting our neighbors who were as close as 25 yards down the beach from us.

Her body began to shake as her legs began to weaken and I took full control in that moment, knowing I could bring us to a wonderful simultaneous climax. My hand tightened around her mouth knowing that she was going to have trouble staying silent with what I had planned for a finale. I fucked her hard from beneath as my balls tightened and within seconds I released a torrent of cum as her lips clamped onto my cock, milking every drop of my seed into her gushing gash.

We sat there in silence for several minutes, catching our breath as we soaked in the final moments of our vacation in paradise. In the morning we would be heading back to the cold of Canada but for now we had a chance to smell the sea breeze as it melded with the scent of our sex. As my cock softened and slipped out of my girlfriend a pool of cum flooded out with it. She replaced her panties to soak up the remnants of our cum cocktail as we sorted ourselves out enough to make the short walk back to our accommodations.

We both liked to sleep naked so once we got back to the place we stripped down and she dropped to her knees and proceeded to lick my cock clean of the cum that had dried on my shaft. The visual alone of her tongue lapping along my foreskin was enough to encourage another erection out of me and we fucked again until we passed in a loving embrace.