I had recently broken up with my live in girlfriend of 5 years and we had planned a vacation for my 30th birthday in the Bahamas at an all inclusive resort. I had gotten a deal by taking a non-refundable option and after some inner dialogue I decided to fly solo and try to enjoy myself.
After arriving at the resort I checked into my room, put on board shorts, an old basketball jersey, sandals, and tried to put on a happy face as I made my way down to the poolside bar.
At the time I wasn't quite in my college baseball shape, but I was standing at 6'3", 215 pounds of mostly muscle, but a little thicker than I used to be, a freshly shaved head and face, pale skin covered with assorted tattoos up and down my arms that desperately needed a tan, and some strategic grooming on my upper body hair. In my mind I was trying to be in the mind set of being single and ready to mingle.
I ordered some sort of tropical rum drink because it felt like to be right thing to do and the bartender quickly grabbed me one as I surveyed my surroundings. There were quite a few attractive women in my age range at the pool, but I'd need some more liquid courage to talk to them.
After three or four rum drinks I lost the tank top and sandles and took a dip in the pool with my drink. Like a wallflower I stayed in my spot, trying not to stare at anyone, and finished my drink at my spot along the edge of the pool.
It had started getting darker as the day turned into night and I made myself comfortable at the bar again. It was slower now at the bar and a well toned and tanned Filipino man took the seat next to me. He was 5'7", thin and toned, dark shoulder length hair, and he was wearing a purple speedo and an unbuttoned Hawaiian shirt. As he sat down he gave off some effeminate vibes as he introduced himself, Danny he said as he shook my hand.
We chatted for a bit and he told me that his friends had gone off to the club, but he didn't want to so he stayed at the pool. After he asked I went over my short story of my recent heartbreak and how I just came here solo hoping to have a good time. He then joked that this was my "Forgetting Sarah Marshall" trip and we had a good laugh at that.
After some more chatting and drinks, Danny became more flirtatious towards an oblivious me. At this point there was very little personal space and Danny gently placed his hand on my upper thigh, rubbing it slightly, and looked at me with a serious look in his eyes, if I had ever been with a man sexually. A little surprised by his forwardness and the question, I managed to stammer out and tell him no, that I never did. He slid his hand up my shorts, stopping short of my bulge, gave me a gentle squeeze, and gave me a sarcastically disappointed look and asked me why I never did. With that I nervously answered it was because I was straight. He smiled as he slid his hand further up my shorts squeezing my stiffening cock and asked me if I was sure. He then released my cock and said it looks like I was at least curious. He leaned over close to me, whispered into my ear, and said I should explore my curiosity with at least a blowjob and I found myself nodding in agreement. He stood up, grabbed my hand, and we headed to my room.
On the way up the elevator to my floor, he slid his hand down my shorts, stroking my cock, not giving me a chance to lose my nerve as we got to my floor. As soon as we got into my room, he pulled my shorts down, got on his knees and started sucking my hard cock. He expertly slid a hair tie off his arm and put his hair in a ponytail as he sucked me and I instinctively started lightly thrusting as I ran my hand through his hair, softly moaning and biting my lip at the talented blowjob.
He then stood up, pulled me over to the bed, told me to lay on my back, crawled between my legs, and started sucking again, now gently squeezing my balls and ass. As he sucks me he starts gently teasing my ass with his finger. Sensing that I was about to blow, he stopped, slid up, grabbed the back of my head, and gave me a forcible deep French kiss that I didn't resist.
As we made out he grabbed my hand and placed it on his hard cock, gently squeezing my hand to grip his cock that he had pulled out of his speedo, and I started to awkwardly stroke it. He kissed me deeply again as I stroked his cock.
He stopped to pull off his speedo, stood up on the bed, showing off an 8 inch cock, and told me to get on my knees and suck his cock. I hesitated and he told me that he knew I was curious about it, so why fight it. I slowly got on my knees as he positioned his tip in front of my mouth and I slowly took it in awkwardly, trying to remember how I like to get head, I started to mimic what I thought was good. He told me to relax as he slid his cock down my throat all the way, slowly thrusting in and out, making me comfortable before he grabbed the back of the head and started fucking my face, causing me to gag and moan. Several times he left his cock deep in my throat causing me to tear up before pulling it out and slapping my face with his cock.
I returned to tonguing and sucking on his hard cock, finding myself eager to please him. He screamed that he was going to cum as I felt his hot load filling my mouth. Not sure what to do, I swallowed his load to his approval and enjoyment. He complement me on being a natural at sucking cock.
As I lay back down he gave my cock a few strokes and said I earned a break and he'd return with some fresh drinks as he put his speedo back on and headed out the door. I sat up half drunk and still horny wondering to myself what just happened and surprised by how much I had enjoyed it.
Danny returned ten minutes later with drinks and a plastic bag full of what he said were snacks. As he handed me my drink, he once again complemented my cock sucking skills and said he'd make a proper slut out of me yet as he reached down and gave my cock a hard squeeze. He gave it a few strokes as we drank our drinks, making sure to keep the mood right. He then put his drink on the nightstand and grabbed mine and put it there as well.
He pushed me back on the bed and immediately started hungrily sucking my cock and as I moaned in pleasure he started teasing my tight virgin hole with his finger, causing me to squirm. As he felt me tensing up and ready to burst he stopped sucking and told me to flip over onto my stomach.
He tossed his speedo past my head and then began sliding his body up mine as I felt his hard cock against my inner thigh and ass. Feeling his cock on my lower back, he licked my ear, and whispered to me that he'd go easy, at first. I heard him grab the bag he had brought in and grab something out of it. Without me realizing it he had lubed up his fingers and slowly pushed one and then two fingers in my tight hole as I moaned. He worked them deeper, slowly stretching me out. After some more fingering to loosen up my ass, he grabbed a pillow, placed it under my hip to get an angle he liked, and told me to relax.
I could feel him lining up his hard cock with tight hole, slowly starting to push it in as I gripped the bedsheets from the initial pain and uncomfortableness. He dripped some more lube on my ass as he pulled out and pushed back in deeper, holding my hips, as he broke through, inching deeper and deeper all the way down as I grunted and moaned. He kept his cock deep inside me for a few moments before he pulled back and thrust slowly back in several times before he began pounding me harder and faster. I moaned and grunted with the thrusts as he broke me in, my hands gripping the bed sheets tightly.
Danny changed his angle slightly allowing him to fuck me even deeper, now pounding me into the mattress as I moaned. He called me a cock hungry slut and asked me who my ass belonged to? All I could say between moans was a muffled "yours".
He then turned me on my side, fucking me in a new position, gripping and pushing my leg up as he pounded away. He slapped my face as he fucked me and all I could do was take it. I was enjoying being used like this.
Danny told me to get on my back and slide to the edge of the bed, positioning my ankles on his shoulders as he looked me straight in the eyes as he slid his cock deep inside me, bending me to the right spot to start pounding and pounding me causing pre cum to leak from my own hard cock. He told me to jerk off and cum for him as he pounded me and I started to stroke my cock. Between his fucking and my own strokes, I shot a load onto my own chest, much to his enjoyment.
He asked me where I wanted him to cum and I told him wherever he wanted. He told me to get on my knees on the bed, pushed me face down into the mattress, grabbed my hips, and started fucking me deep and fast. As I moaned he told me to take it all as he filled my ass with his load, pounding away until he was satisfied.
He pulled out, slid up next to me on the bed, cum leaking from my ass, and as I was trying to catch my breath, he gave me a deep and dominating kiss. He complimented me for taking it like a man and he stood up, put his speedo and shirt back on, and told me he'd be at the resort all week as he wrote his number on the notepad on a nearby desk. He told me to text him if I'm down for another round. He then left, leaving me naked on the bed covered in sweat and full of cum. Unexpectedly enjoying my first gay experience.
