Beach Vacation

I was traveling on vacation with my wife and never even considered this would become an opportunity to explore a gay sexual adventure. I haven't been with another man for almost two years and while I thought about exploring that side of my sexuality on occasion, I just hadn't searched out another experience, but things were about to change.

As we arrived at our tropical destination I immediately noticed that there were a proportionately large number of gay couples in attendance, including two of the 4 couples on our bus from the airport to the resort. While I have a couple of experiences with guys in the past, my wife is in the dark about those experiences, so while I was getting turned on thinking about all the gay sex that would be taking place at the resort, I never let my wife know of those secret fantasies, nor did I think that any opportunity would arise for me to partake in the fulfillment of the fantasies I was having.

All that would change on a rainy afternoon.

There was a particular older gentleman that had been catching my eye for the first couple of days. He and his partner always occupied the same seats on the deck of the pool, and my wife and I ended up sitting only a few chairs away on each of those first days. The gentleman in question was probably mid 50's, while I am slowly nearing my 40th birthday. He would wear a speedo each day to the pool, and while he sported a few extra pounds, that he wore well for an older man, his body didn't get many looks from me as my eyes were always drawn to his speedo and what appeared to be a large cock contained by the tight fabric.

As I sat on my lounge chair reading, I would take peaks of him and his partner rubbing sunscreen on each other or watch him walking to and from the pool bar. Some time I guess the peaks weren't quite so subtle as I would catch him looking back at me, but in those instances I would try and play it off by giving him a quick smile and then switch my gaze to other things going on around the pool. From what I could gauge, it didn't seem like he was interested in anyone other than his partner, and I was there with my wife, so it wasn't like I was looking to pursue anything anyway.

On the third afternoon of the trip the ball started rolling downhill and, unbeknownst to me, I was being lured into an experience that ended up satisfying a lot of the cravings that I had been suppressing for the past couple of years.

As I approached the pool bar for my second round of drinks of the afternoon, I saw the gentleman get up off his chair and walk towards the bar and I gave him a quick glance, but then turned back to order our drinks. As I stood waiting for our drinks to be prepared, I felt someone standing close behind me. I knew it was him, but didn't have the courage to turn and look at him. Instead I watched as the bartender mixed the drinks and felt the gentleman behind me push up against my back, his stomach pressing into my back. Then he reached across my body to signal he wanted a drink, brushing his arm against mine and letting it linger momentarily as I didn't move away. We stood there for a moment as I waited for my drinks, with him pressed closely behind me and my cock hardening in my board shorts.

As the drinks arrived, I snatched them up and reluctantly started to ease past him to head back to my lounge chair. As I passed him, he let his hand slide across my body and I'm sure he could feel my semi-erect cock as it brushed the back of his hand. This was definitely the point where I knew the game had changed and was certain that the rest of the vacation could be a little more interesting than I was expecting. When I arrived at my lounge chair, I got settled and then glanced to see him returning to his chair. This time we locked eyes and neither of us tried to play it off as a casual glance.

The next time I went to get drinks, it was no surprise to see him casually following me to the bar and this time I was eager to see what would happen. This time he again came up behind me and pressed his body against me, but this time I felt his hand reach down between us and grab hold of my ass. He let his hand wander all over my ass until my drinks arrived and I had to return to my lounge chair, sporting what was now a much more erect cock.

The next half hour saw cloud cover roll in and a big storm start to gain traction. My wife decided to make a run to the comfort of our hotel room, while I made a decision to wait out the storm at the swim up bar, figuring it would be wet in the pool anyway. I was hoping my gentleman friend might make a similar decision. As I jumped in the pool I saw him lean over to speak to his partner and moments later he was following me towards the swim up bar.

As I approached the swim bar, I realized I wasn't the only one with this idea and people were actually lined up a couple rows deep waiting for drinks, meaning that I wasn't even able to get to a spot where I could stand with more than my shoulders out of the water. As my friend approached, I looked over my shoulder to notice that he was alone and that his partner had headed back to their room to avoid the weather. He approached and made clear what his intentions were as his hand reached under the water and gave my ass a quick grab before reaching around and grabbing my cock. He didn't just grab my cock through my shorts, but actually put his hand down my swim trunks and started stroking me, making it very clear that we were both understanding where this was headed.

We didn't even think of ordering drinks and instead he asked me if I wanted to come back to his hotel room. I was worried that my wife might come out and notice I was missing, but at the same time knew that I couldn't resist this opportunity, so I nodded my head and followed him as he climbed out of the water and headed towards his hotel room. As we got out of the rain and into the hallway leading to his room, I asked if his partner was going to be in the room and whether or not he was okay with this, to which he responded in a thick, what I thought to be German, accent that his partner would be there but only watching unless I asked him to join. This was the point where I almost changed my mind as I was a little worried to be entering a room by myself with two strange guys, but the thought of what might take place was enough to displace my fear and I didn't give it another worry and blindly followed this man to his room.

We reached his room and with a swipe of his card and the green light appearing, I felt my knees begin to tremble as the nervousness took over. In a span of only microseconds, but what felt like an eternity, I questioned whether I was ready for this. Would my relative inexperience cause me to make a fool of myself?

All those thoughts were thrown to the wind as he grabbed my hand and guided me into his room. As the door closed behind me, he pulled me tight to his body and leaned down to kiss me. His lips felt soft against mine and we started passionately making out, both of us breathing heavy and beginning to explore each other's bodies with our hands. As we kissed I felt his tongue begin probing and without hesitation parted my lips to allow our tongues access to one another. His hands were on my ass, pulling our groins tight to one another and had one hand on the back of his head, while I played with his nipples with my other hand.

There was no sense of urgency, as our makeout session continued for quite some time and we were both content to feel our bodies pressing together and explore with our hands. But eventually, I got so turned on by the feel of his hard cock against my stomach that I had to feel it. As we continued to kiss, I reached down and slid my hand over top of his speedo, rubbing his hard cock with the nice smooth fabric covering it. He was moaning into my mouth and without actually saying it, was begging for me to help him lose the speedo and get my hand on his cock.

Given that I had the luxury of seeing him parade around in a speedo all week, I knew that he had a considerably large package, but this was the first opportunity I had to see it at full mast and as I reached inside his speedo and pulled out his cock, I was in awe at it's actual enormity. I've seen some large cocks in porno films, but never had an opportunity to see one over 7 inches in person. This cock was impressive and I had to guess it was approaching 9 inches in length as it reached its maximum rigidness. It took my breath away as I never imagined I would be holding such a large and perfect cock in my hand. The girth was so thick that I couldn't actually get my hand all the way around it as I stroked him.

I had to break off our makeout session and get a close up view of this cock that was quickly becoming a play toy in my hands. I dropped to my knees and continued to stroke his cock with one hand, while I pulled down his speedo with my other hand. As he stepped out of his speedo, I ran my hand up his leg until I reached his testicles and then continued to stroke his shaft while giving his balls a nice massage. I was working up the courage to put this gorgeous piece of meat in my mouth, but was reluctant due to it's size and my not knowing if I could even fit it in my mouth.

I knew I had to taste this marvelous cock, but decided to take it slow and work my way up, starting by licking his balls and then up and down his shaft a few time with my tongue. Finally I couldn't resist and put my doubts aside and went for it. I opened wide and slid as much of that cock into my mouth as I could handle. As it turns out, I couldn't handle much of it and found myself gagging before I even got halfway down the shaft. I wasn't going to disappoint though, so I continued to bear down on this magnificent cock and as I bobbed up and down I was able to take a little more of his cock each time. It was going so deep in my throat that I thought I was going to suffocate myself, but I stuck with it and was finally able to take his whole cock down, fighting hard not to gag. He was so patient with my attempt, but once he found I was able to deal with his size, he grabbed the back of my head and slowly began to fuck my face. While I was gasping for air at time, the feeling of being used as this guys personal fuck toy had me so hard that I was close to cumming without even being touched. We stayed in this position for a while, getting a nice rhythm going. As he fucked my face I was rubbing his balls with my hand and I could feel them starting to tighten up as his pace quickened.

As his balls tightened, I could feel the massive head of his cock expand in mouth and what seemed like a never ending flow of cum erupt down my throat. His first couple of squirts were straight down my throat, causing me to almost choke, then he pulled out and finished cumming as he sprayed my face with copious amounts of his cream, some of which dripped onto my chest and others that found the tile floor of his room. I've never been a huge fan of swallowing cum, but I wasn't going to let this man down, so I managed to swallow all the cum that had ended up in my mouth and then I pulled his cock back to my face and licked it clean.

As I was cleaning his cock, I noticed movement out of the corner of the room and suddenly remembered that this man's partner was in the room. His partner came over to me with a towel and gently removed all the cum from my face and body that had been deposited by our mutual lover. He was fully clothed in shorts and a t-shirt, but I could see his cock straining as he finished toweling me off and returned to sit in a chair in the dark corner of their room.

This was the first lull in our encounter and I wasn't sure what was next, but my new partner pulled me to my feet and guided me to the king sized canopy bed housed in the middle of their room. He gently pushed me onto my back on the bed and reached down to remove my swim trunks. After tossing my swim trunks onto the floor, he climbed into bed with me and we began to kiss once again, this time with our naked bodies intertwined and his still hard cock pinned between our bodies. With the massive cock between his legs, I wondered if he would have any interest in my little 6 inch cock, but as we made out, he reached down and took hold of it in his large hand. He then started kissing down my body, taking lot of time to lick and suck my nipples and ended with his tongue slowly licking across my shaft, down my balls and then finding a spot between my balls and ass. Next he lifted my ass up with his hands and started rimming my ass. I love the feeling of being rimmed and can just about reach orgasm from that alone. My cock was dripping pre-cum at this point and wasn't sure how long I could last if he touched it.

He had other ideas though and starting inserting his thick fingers into my ass as he spit on them to get lubrication. After pumping me with his fingers for a couple of minutes and watching the pre-cum pour out of my cock, he slowly made his way back up my body until our lips met again. We started kissing again and he positioned himself so that I could feel his massive member rubbing on my hole. As he rubbed up and down I began to spread my legs further apart, giving him an invitation to enter me. He sensed my acceptance and reached down to guide his head into my hole. It wasn't an easy process as my ass was really tight, having only been fucked one other time, so I was grateful that he took things slowly and eased his cock in inch by inch, stopping repeatedly to give me time to relax and open up to take more. After a grueling amount of time, and some considerable pain on my end of things, I was finally able to feel him reach bottom. He stayed still for a few moments, making out with me, but leaving his cock at its full depth, letting me get accustomed to a fullness that I've never felt before. It felt like he was so deep into me that if he were to come it would end up flying out my nose.

After a couple of minutes of making out, he began to slowly fuck me. At first only moving his cock an inch or two, then starting to take longer strokes, before finally pulling all the way out and pushing back into my gaping hole. I was a complete mess as his cock was hitting pleasure spots I didn't know I had and I didn't want this to stop. He picked up the rhythm and any pain I had experienced in the beginning was now replaced with incredible pleasure.

As he pounded me, I glanced over to see that his partner had removed his shorts and was slowly stroking himself in the corner while he watched me being used like a sex doll. While his partner didn't have quite as big of a cock, it was probably still 7 inches and much thicker than my cock. At this point I was lost in ecstasy and decided to go for broke. I motioned for his partner to come over and while I was getting fucked I took his cock into my mouth and tried to match the rhythm of my fucking as I bobbed on his cock.

It wasn't long before I felt the cock in my mouth starting to erupt. He pulled it out and as I lay with my mouth open he sprayed cum all over my face and in my mouth, finishing by slapping the cock across my face and letting me clean the remaining cum off of him.

Watching his partner cum must have been a catalyst for my new lover as I felt his cock go rigid and then felt a warmth deep in my bowels that I've never felt before. He unleashed a massive load into my innards and as this was happening I reached down to stroke my own cock and it exploded all over my stomach and chest with only a couple of pulls.

I was a complete mess, cum all over my face, in my hair, all over my body and in my ass, but I had never felt so sexually fulfilled in my life. My new lover and his partner both leaned down to give me a kiss and after a few minutes of alternating between kissing the two of them, I decided that I needed to get cleaned up and back to reality. I had a quick shower, threw my swim trunks back on and headed out of the room. It was still raining outside, so I headed back to my room, where I found my wife sound asleep in our bed, oblivious to my crazy afternoon.