Sluts Before Social Media

Things were much different before social media. If you ask me - social media ruined a LOT of good fun.

When I was in my twenties I was big on traveling alone. I loved the idea that I could travel to a new city like San Francisco or Key West and have all the fun I wanted without everyone back home knowing all my business.

Key West was a great place to visit during the off season. Hotel rates were cheaper, drinks were cheaper and there were still plenty of hot guys roaming the island. One of my favorite trips was back in 2002. I arrived in Key West for a weeklong stay and had decided to stay at a gay clothing optional resort for the first time. I’m your average 6ft 180lb guy next door. In shape but a small belly from my love of beer and certainly did not live in the gym. But at 25 you really don’t have to try that hard to be ‘in shape’.

I arrived at the resort before official check-in time so the guy behind the desk said they would be happy to store my luggage if I wanted to enjoy the pool or explore in-town until my room was ready. I got my keys and took a walk out to the pool area to check it out before heading to a nearby bar for a drink. The pool area itself was surrounded by the guest house rooms on two floors. The upper rooms also had a nice balcony walkway that ran the length of the pool, and I noticed a few guys just hanging out upstairs enjoying the view. And by view, I mean the hunky guys around and in the pool. Some were wearing swimsuits, some were clearly embracing the clothing optional…option. One specify guy was laying in a lounge chair directly in front of me across the pool. He had on mirrored sunglasses and a gold necklace…and nothing else. I couldn’t see his eyes to tell if he was asleep or awake…but he had a half-smile on his face that made it seem he was relaxed and enjoying himself. My eyes were hidden behind my sunglasses so I took my chance to enjoy the view from head to foot. He had salt and pepper hair that was buzzed short and sparkled in the sun. Those mirrored sunglasses sat on a handsome face with a square jaw and thick gym-build neck and shoulders. What really took my breath away was his fur covered huge chest. It looked like something out of a Tom of Finland book. And just as you would expect it was followed by a flat fury stomach, small tight waist and then the biggest thickest dick I have ever seen. Even soft, it rested on his huge balls and cast a shadow on his thick thigh. His thighs were so muscled that they just pushed his balls up and out making that beautiful cock even more pronounced. I must have spent a bit too long staring because when I looked up I noticed that his grin had grown into a full blow smile and he was looking in my direction. 

A bit flustered I tried to play it off by walking the opposite way around the pool. I made a show of looking EVERYWHERE but in his direction as I worked my way around the pool and then back towards the front door of the guesthouse. I breezed past the front desk and out the door of the resort. Stopped, adjusted my stiffening dick in my shorts, and then took off in search of a cold beer.

There is a great bar on Duval street that is a bar facing the street but it is also attached to a guesthouse - so there is a pool/bar in the back. I walked through the dark cool air-conditioned bar and out the back door to the hot summer Key West heat I loved so much. It was early in the day and so it was just me and the bartender when I arrived. I ordered a beer and shot and then settled myself on a barstool to soak in the relaxing tropical air.

Some idol chit-chat, a few beers and a few shots later I was really starting to let go of the everyday stress I came here to escape. The heat and humidity were both so high that I was sweating like crazy just sitting still at the bar. I got up and went to the restroom and then on my way back I peeled out of my tank top and shoved it into the back pocket of my shorts.  The bartender was already shirtless and because it was a pool bar I figured no harm done. 

When I got back to my seat at the bar a few more customers had arrived. A friendly ( already kinda drunk ) couple visiting from Texas and a quiet older guy visiting from Baltimore. We had some great conversation and before I knew it my official check-in time had flown by. I thanked the bartender for the drinks and service, said my goodbyes and headed back to the resort. The whole walk back, all I could think about was getting another look at the hunky god next to the pool. 

Before you know it I had collected my luggage from the front desk of the resort and started toward my room. I was on the upper floor in a king bed room that faced the pool…score!

As I rounded the corner to the pool I was a bit disappointed to see that my vacation crush was no longer sunning himself at the pool. There was plenty of other eye-candy but nothing that stopped me in my tracks. 

Once I got to my room I made quick work of unpacking my things into the closet and dresser, set up my toiletries in the bathroom, put a bottle of lube and some condoms in the nightstand and then stripped off all my sweaty clothes. After a quick rinse in the shower and a quick towel dry…I opened my dresser and grabbed a pair of swim trunks I bought especially for this trip. They were short and snug and showed off my package. The best part was that they were white thin material and so once they got wet they left little to the imagination. I figured I might as well jump right in to this vacation. 

I grabbed a towel and threw it over my shoulder, put on my sunglasses and was out the door in no time. Standing on the upper balcony looking down at the pool I got a great view of everyone. Across the way around the upper balcony was a sundeck across from my room. As I headed off in that direction I realized that the upper balcony split off in two directions. To the left it lead across to the upper sun deck with lots of lounge chairs and some those cooling water misting fans. 

To the right it looked like there were some more guest rooms and another door with black plastic strips hanging in the doorway. Curiosity getting the better of me I decided to wander back and peek inside. As I got closer it dawned on my it was the ‘play room’ they had advertised. Mostly it was just a dark room with dim red lights were guys could go to mess around. I was guessing that because it was so crazy hot outside that it was probably more of a night-time thing. Not being one to want to mess out I poked my head through the plastic strips and stepped inside anyway. As soon as my eyes adjusted I was stopped dead in my tracks. Directly in front of me was a giant guy with his back to me. Kneeling in front of him was a guy on his knees. The giant guy was clearly giving him a good face-fucking judging from the gagging sputtering sounds. Neither guy seemed to notice my arrival since they didn’t miss a beat. I stood there mesmerized by the moving muscles on the giant guys shoulder and arms. I watched his huge arms and back muscles move in time with his hip thrusts. His tank top had ridden up his sweaty back and his swimsuit was pulled down just far enough to see the tops of his ass cheeks. His rhythm was fast and rough…it looked more like he was using a sex toy than another guys mouth. 

The whole scene was intoxicating. Unnoticed, I was getting to enjoy a real life porn. As my eyes darted around the room I saw that there were mirrors all over - including a few at angles up towards the ceiling. As my eyes searched all the angles I realized that every view was a different kind of hot. One direction I could watch his dick sliding in and out of the guys mouth. Another I could see my own reflection with my hand down the front of my swimsuit stroking my dick. But my eyes just kept returning to the sweaty tank top sticking to they guys back and the motion of his ass slamming backward and forward. 

Enjoying the show, I pushed my swimsuit down to my knees and started to jerk my dick in time with his strokes. It wasn’t long until I was headed to the point of no return. 

Before I could get close to an orgasm the big guy let out a series of grunts and his hips lost their rhythm. He pulled the kneeling guys face tight into his pubes and I watched him throw his head back and shoot a load into the waiting throat. That was enough to push me over the edge too and I started to feel the orgasm coming on. It was a quick series of events.

The big guy started shooting his load, the kneeling guy started sputtering and choking on the load and I started to feel the electricity of a good orgasm run up my spine. I watched as the big guy spasmed and thrust his hips and I kept myself right on the edge to prolong the thrill. I waited just a bit too long because the next thing that happened was that the big guy made one last grunt followed by a sigh of relief. That made every muscle in my body flex and the first shot of cum rocketed out of my dick. In one smooth motion the big guy pushed the kneeling guys head off his dick and was putting his dick back in his shorts as he turned around to see the second shot of cum leave my dick. With my hand still pounding my dick, our eyes met as the third shot rocketed out of my dick. Then it dawned on me that I was looking at the greek god from the pool.

He took a step toward me as bursts of cum kept shooting out of my dick. The orgasm had control and I couldn’t stop stroking. Our eyes stayed locked as he walked toward me and reached down to grab my dick. He used the cum still covering my dick and hand as lube as he helped took over milking out the last few spurts. The orgasm had my knees weak and I had to lean back against the wall. I dropped my hand away from my dick and looked into the strangers eyes as he milked what was left of my orgasm out of my body and then worked my sensitive dick making my whole body twitch. 

Without warning he released my dick, wiped the cum on my towel still over my shoulder and then slipped out of the plastic strips on the door. 

I was a bit stunned and only then realized that the kneeling guys was now walking past me to the exit smiling and licking his lips…then he too was gone. I was left standing in the dark room with my shorts around my knees and my sensitive dick still bouncing up and down from the final orgasm spasms running through my body.

Wow. What a way to start a vacation. After I collected myself and got my dick put away in my swimsuit I decided to head out to the pool deck to get some sun.

I slipped out of the dark room and made my way over to the sun deck on the upper level. I was the only one in the area and decided that it would be a good opportunity to strip naked and catch some of the evening sun as it was setting over the island. 

Super relaxed from my dark room encounter I quickly fell asleep. When I woke up, the sun had gone down and the resort was almost silent and peaceful. I returned to my room, showered and put on a baggy pair of cargo shorts, tank top, baseball cap and some flip flops..then headed out to grab some dinner. 

After dinner I decided to take a walk down Duval to check out what was happening in the bars. One bar had drag queens performing, one looked like your typical happy hour crowd and then my eyes caught the bar with the strippers standing out front. Bingo!

I made a quick trip to the ATM and then headed up to the bar for some drinks. I got a shot, a beer and then asked the bartender to change my $200 into singles, fives and twenties. I took a seat at table in the back and took my time to enjoy the view. 

Before you know it a hunky stripper made his way over to me to start chatting. We ran through the typical “where are you from…blah, blah, blah” questions. I slipped a few dollars into his waistband. He was wearing a thin pair of black soccer shorts pulled down low enough on his hips to see the white jock he was wearing underneath. Each time I slipped more dollars in his waistband he would pull the front of the shorts a bit lower. He had his back to the rest of the bar so his little show was pretty much for my eyes only. About $40 and half a beer later he had the front of the shorts pulled over and under his bulging jock so it pushed his package up and out towards me. I was sitting on the barstool with my legs spread and he was standing in front of me between my knees. 

I was thinking to myself that they sure allow a lot of touching compared to most strip bars I’ve been in. I didn’t even complete the thought as he tucked his thumbs into the waistband of his jock and slid it down over his huge cock and balls. As they sprung out the front of his jock I quickly started looking around to see if we were going to get busted. He chuckled and told me not to worry…it was ok. In the same breath he took my hand and guided it to his now stiffening dick. 

You don’t have to tell me twice. I grabbed hold of his cock with one hand and then moved my other underneath his balls. We continued our chatting as I slow stroked his cock and massaged his balls. He was a guy with a lot of pre-cum and I didn’t let it go to waste. I used it to slick up his dick and massage the head until he was throbbing. After I had him pretty worked up he asked if I wanted a private lap dance. I thought, what the hell and off we went to a little room with a curtain at the back of the bar. We slipped inside, he pulled the curtain closed. I sat down on the wooden bench against the wall and he walked over and straddled my legs. He started his lap dance in time to the music. Rubbing on my chest and shoulders and grinding into my hardon pushing against the inside of my shorts. 

He told me he lived in Miami and that he came to Key West on weekends to dance. I stood him up off my lap and took him by the waist to turn him around. He had an amazing ass and I wanted to see more of it while we had the privacy of the room. After I had his back to me I reached up and grabbed the waistband of his little black shorts. I started to slide them down over his jock and asked him if it was ok. He said of course and played into grinding his hips as I lowered his shorts to his knees. 

The way the jock framed his ass had my dick leaking in my shorts. It had already made a wet spot in the front. In the process of lowering his shorts a few of his dollars dropped onto the floor. Knowing exactly how to use his body he bent over to make a show of picking them up one by one. I was massaging his ass and every time he bent over his muscled ass cheeks would spread just enough to ALMOST show his asshole. After a few teases I couldn’t take any more and with the next time he bent I helped them apart with my hands. He seemed to be into it so the next bend I did it again and then reached in for a quick lick of that tight hole. That made him freeze in the bent over position and lean back towards me. That was all the green light I needed. I spread those cheeks apart and gave him a good working over. He had to brace his hands against the floor and that left him open and ready for me. I worked his hole with my tongue up and down his crack until he was grinding and gyrating his hips. I decided to see just how much fun this hunk was looking for so I slid my hand up inside his jock from behind. In one motion I stretched his jock down away from his body with my left hand and used my right hand to free his dick and balls. His dick was rock hard and instantly became my handle to keep him in place. With a firm grip on his boner in my right hand I gave him the rimming of his life. I licked his ass and stroked his cock until is was nice and slick and then alternated licking and tounge fucking his tight hole. 

At this point his shorts and jock were around his ankles and that was the only thing keeping him from spreading his legs wider. I was horny and wondering how far this dude would go in a public place…so I reached down with my left hand lifted his left foot off the ground. As he lifted his foot I slipped his shorts and jock off over his tennis shoe. He lowered his foot back to the ground and his now free leg slid further apart. 

I started using both hands to slick up his hard dick and I continued to lick his crack, balls and tongue fuck him. I could tell he was getting close to orgasm because his balls had pulled up tight to his body. I spent the next twenty minutes getting him right to the edge and then backing off…over and over.

Once he was bent over with his hands on the ground, jock and shorts around one foot and begging to cum. I decided it was time to put him out of his misery. I worked him back up to the edge and this time didn’t slow down. I pumped his dick with my right hand and started tongue fucking for all I was worth. I reached up between his legs and grabbed his nipple with my left hand and that was all it took. His legs started shaking and he couldn’t hold back his moans. I swear I could hear the first shot of cum hit the floor over the loud music in the club. I moved my left hand back to I was using both hands to stoke his dick from top to bottom - milking out every drop of cum he had been working up. Even after the cum stopped I kept up the slow milking until his whole body was covered in sweat and trembling from the extended orgasm. When he finally couldn’t take any more he dropped down until he was on his hands and his knees. 

I didn’t let go of his dick with my right hand and continued the slow stroking with his stiff dick now pointing out behind him. His raging boner caused him to almost put his face and chest on the floor to keep from hurting his dick and that expose his hole even more. I took the opportunity to spit a fat wad right on to his hole and work it around in circles using the thumb of my left hand. I kept up the slow strokes and hole massage until he was a puddle on the dirty club floor. I could tell he was still riding the after effects of the orgasm and hole massage and was guessing he would stay in that position as long as I kept it up. 

I was prepared to see how long he would go when the little black curtain to the room flew open. A stripper led another customer into to booth until they were almost right on top of us. As soon as they realized the room was occupied they quickly shifted focus to the stripper that was naked on the floor getting his dick and hole worked. The other stripper apologized and said they could find a room. Without letting go of his dick I told them to come on in we were just finishing up. Everyone was all smiles and they both stepped inside and slid the curtain shut. The customer took a seat next to me and the strippers were making some serious eye contact trying to decide what to do next. 

I decided to go with the flow and asked the customer next to me if he could take over for me. I moved his hand to take hold of my strippers dick and he went right to stroking. I then stood up and kept up massaging his hole as the new customer slid into my place. The stripper on the floor seemed to stay in the zone. I moved off to the side so I could just watch the show.

Thinking that I had for sure gotten more than my moneys worth I pulled the remaining cash out of my pocket. I bent down to my knees so I could look the stripper on the ground in the face. I lifted his chin and told him that was the most amazing lap dance I have ever had. He was blushing and smiling but not saying much. They new customer continued to work his dick and hole as I was talking to him. I held out the cash I pulled out of my pocket until he reached up and took it from me. I tried to start up a conversation just to see how he would handle it. I asked if he was working tomorrow. When he was going back to Miami. How late he was working tonight and anything else I could think of. His eyes were fluttering and sweat was dripping off his face. I could tell that the new customer was doing a great job at cranking up the next orgasm. The stripper on the floor was struggling to keep up with my conversation.

I did my best to get the new stripper and new customer all in on the questions and answers. Everyone was carrying on like the naked guy on the floor getting jerked and fingered was totally normal.

Then I stood up, adjusted myself and slid the curtain open wide. I took my time saying goodbye to ensure that all the guys in the back of the bar got an eye full of the show. The stripper of the floor was obviously embarrassed but far to horny to make a move to get up. I kept up my questions to get him to look up at me then finally said goodbye and walked off leaving the curtain open. A few of the guys standing around had moved in closer so I’m not sure if they curtain ever got closed again or not. 

I had a raging boner that needed some attention so I headed out of the bar and back towards the resort. 

When I got back to the resort it was pretty early in the evening. It was just before 11pm and everyone was clearly still out at the bars for the night. I went back to my room, stripped out of my clothes and decide it would be a good time for a skinny dip in the quiet pool.  I wrapped a towel around my waist, left my room unlocked so I didn’t have to keep up with a key…and then headed out to the pool.

As I closed my door I thought it might be a good idea to peek into the dark room. I still had a hardon that needed some attention. Maybe  I would be lucky enough to catch a repeat performance by my muscle daddy from earlier.

When I poked my head into the dark room I was a bit disappointed to see that it was empty. The only thing different from earlier was that there was now porn playing on the tv in the corner of the room. With time to take a closer look at room - I slipped inside and noticed that what I thought was a  bench earlier, was actually a large leather covered platform bed/ play area. Nice!

Since there was a lack of action up here it was time to head down to the pool. Just as before it looked like I had the whole place to myself. The idea of a clothing optional place was enough on it’s own to keep me horny. 

I decided to test the limits of my new freedom and threw my towel over my shoulder. I roamed around the resort checking things out with my hard dick bobbing around in front of me. I checked out the hot tub area and the vending machines I had missed earlier. I noticed that around the corner from the bar by the pool there was a restroom available as well. Once I felt like I had the lay of the land I threw my towel on a lounge chair and got in the pool. 

The peaceful quiet resort was just perfect. I swam around leisurely feel the warm water slide over my naked body and hard dick. Growing a bit bolder with my new freedom - I decided to hop out of the pool and hit the restroom by the bar. I didn’t even bother grabbing my towel. Just the short naked walk had my dick harder than ever and I took me some time to accomplish taking a leak. 

Once I returned to the pool, I decided to take an even longer ‘naked walk’ back to my room to get a beer. I had grabbed a 6-pack on the way home and stocked my little mini fridge with beer and the bottle of tequila I had packed in my luggage.

I even decided to take the long way back to my room. With my dick bobbing in front of me I climbed the stairs on the opposite side of the pool to the upper sun deck and then made my way around past the other guest rooms back to my room. 

I was almost back to my room when the door next to mine opened up and my muscle god from earlier stepped out onto the walkway between me and my door. He was dressed in jeans, boots and a white tank top with that gold chain catching the overhead light.

He instantly made eye contact and then took a slow look down my body to my hard dick where his eyes stopped and lingered. The walkway wasn’t super wide so there was really nowhere for me to go. He walked right up to me, stuck out his hand and introduced himself as Bob. 

Rattled I took his hand and shook it and introduced myself as well. Instead of dropping my hand he just held on and began asking me other questions. My heart was beating so hard that I struggled to follow his line of questions. He asked if I was enjoying myself and I nervously laughed and said yes. Holding my right hand with his right hand he casually swung his left hand up and grabbed on to my hard dick between us. 

He said he thought it looked like I was having fun. As he continued to ask me questions he started a casual slow stroking on my rock hard dick. He asked me if I was heading out to the bar and I told him I had gone earlier. He let go of my hand moved his now free hand up to tug at my hard nipples in turn - back and forth while he was stroking my cock. 

My brain was on overload. My hands just hung at my side and I stared up into the that hunky face while he tugged my dick and nipples and chatted away. He said he thought I should come with him for a drink and in my state of mind how could I say no!

I told him I needed to get my towel from the pool and put on some clothes. He said he would wait for me and let go of my dick and nipple and leaned against the wall outside my room. As I nervously excused myself I tried to step past him to my door. He reached out and put a flat hand on my stomach stopping me in place. He said ‘ I thought you needed to go get your towel from the pool’…Stunned and still rattled I said ‘oh, yeah…be right back’. And then flipped around and hurried back down to the pool. My dick was flopping back and forth in front of me and my nipples felt like they were tingling with electricity. 

I got back down to the pool, grabbed my towel and quickly wrapped it around my waist to try to trap my hard dick against my stomach. As I headed back up the stairs I had all kinds of images flashing through my head. Mostly that I hoped I got to suck that big beautiful dick of his before the night was over.

When I got back to my room he followed me inside leaving the door standing open and then sitting on my bed. My thought was to drop the towel, pull back on my cargo shorts, tank, cap and flip flops and then we would be on our way.

What happened was I dropped the towel and bent over to grab my shorts. When I did, Bob grabbed me by the waist and pulled me over to where he was sitting on the foot of my bed. He turned me around to face him, took my shorts out of my hand and laid them on the bed next to us. Then he pulled me up onto his lap facing him so that my legs were straddling his. 

He lifted my arms and put them around his neck which brought our faces close together. With his free hands he reached down and grabbed both my nipples in a firm grip. My nipple are super sensitive and this made me moan. He leaned in closer and started kissing me. I was all about it and really got into the kissing. With my arms around his neck he let his hands slide from my nipples down my sides, around to my ass cheeks, down the outside of my thighs to my knees and then up the inside of my things until I felt him grab my dick and balls. He started the slow stroke of my dick at the same time he circled my balls and started to pull down on them. This got another moan out of me. 

He broke off from the kiss and started asking me questions as he massage my dick and balls. ‘How long are you visiting for?’ ‘Do you have a boyfriend?’ ‘ Do you like to bottom?’ 

With that last question he released my balls and time the question with the exact movement from releasing my balls to sliding his fingers under my balls and across my asshole. You can imaging the groan and ‘yes’ answer all at once.

When I said yes he smiled really big and began slow teasing circles around my spread hole as he was working my dick.  Then he leaned in and started kissing me again while he worked my hole and dick.

I was thinking were absolutely not going out for that drink now! He kept up the kissing, jerking and hole massaging until he had me moaning and grinding my hips into his teasing fingers. He broke the kiss and asked ‘do you have any lube?’ I said yes and he said ‘go get it’. 

I reluctantly slid back wards off his lap and hurried over to the nightstand where I had stored my lube and condoms. I grabbed the bottle and a condom and went back to stand in front of him. He pulled me back onto his lap and returned to the slow jerking of my dick. He told me ‘open that bottle and lube up your asshole for me’. 

He took the condom out of my hand and quickly opened the lube bottle, squirted some into my hand and then reached around to start lubing up my hole. After a few squirt and repeats I was successfully fingering my self smoothly. He reached down and grabbed my discarded towel off the floor and handed it to me to wipe the lube off my hands. 

While I was wiping my hands he laid the condom on the bed next to us and said ‘we don’t need that just yet’.

As I was wiping my hands he kept his jerking of my dick slow and reached under and between my legs to start rubbing my now well lubed hole. I threw the towel on the floor returned my arms around his neck. He reached up and started kissing me as I felt his first finger slide into my hole. He was a master at moving the focus from our kiss to my dick to my hole and back again. It seems like that make out session went on forever until he had me moaning and groaning. Eventually I realized his hand had moved off my dick to the small of my back and we were just making out while he held my ass cheek in one hand and finger fucked me from underneath with the other. My dick stayed hard with the head rubbing back and forth on the front of his shirt. 

I was really getting into it when he pulled back from the kiss and reached for the lube bottle with his free hand. As he slowly fingered my hole he asked ‘does that feel good?’ 

I moaned and said yes and watched as he popped the top on the lube bottle. He slid his finger out of my hole and then squeezed more lube onto his fingers. He stared into my eyes and he returned his newly slick fingers to my hole. I wasn’t able to break eye contact as he slid two slick fingers in all the way to the second knuckles and made me moan again. 

Then he pulled his fingers out and started the fresh lube process over again. He stared into my eyes as he repeated the process over and over. All the way in, all the way out, more lube. All the way in, all the way out, more lube. It was like the penetration was the first time every time. But every time he did it his fingers slid in easier and easier as I got more and more relaxed.

Eventually there was no kissing or jerking my dick. It was just me straddling his lap and him fingering me all the way out and all the way in. Then he started the conversation again. ‘Where do you want to go for a drink?’. I was having trouble focusing and responding. And he had to ask me again. I said ‘we can just stay here’…

He started chuckling and said ‘no, we have to go for a drink. This is just the warm up..’ At this point I was slutty putty in his hands. He said ‘ You have a great hole’. I wasn’t even sure how to respond to that. Then he said ‘Stand up.’ 

Without taking his fingers out of my hole he slid me backwards until my feet slid down off his lap and hit the floor. My knees were weak and I had to keep holding on to his shoulders. Once I was standing he stood up too. He reached down with his left hand and pulled my right knee up until my right foot was on the end of the bed. Now his fingers were still in my hole but my one foot up on the bed and one foot on the floor spread my hole even further open. Standing in front of me he started to slowly finger fuck me again and used his free hand to start tugging on my nipples again. My moaning got a little louder and his finger fucking started picking up speed. All the way out to the finger tips and then all the way back in to the second knuckles. My moaning started to turn into grunting as I got close to cumming. I had never cum hands free before but that was where this was headed for sure.

Then like someone flipping a light switch he pulled his fingers out and stepped around behind me. He grabbed the lube bottle off the bed…pop…squirt…more lube on the fingers and then I felt one hand grab my left shoulder and the newly slick fingers slide back into my hole. 

Now he was standing behind me holding my shoulder and finger fucking my hole long deep smooth strokes. All the way in… all the way out. I had one foot on the bed and one of the floor. My hard dick standing out like a flag pole and my hands hanging at my sides.

All of the sudden I realized we never closed the door. And I could hear voice down by the pool. This seem to ratchet up the excitement to all new levels. He started the conversation again..’what do you feel like…beer..or liquor?’ chuckling he said ‘Is this too distracting?’ …

All I could do is grunt and groan. About that time two guys walked by my open door and took in the scene. I thought that was it…I felt the orgasm coming on and my body tensed up. 

Almost like it was planned his fingers left my hole and used my shoulder to keep me steady while he grabbed the towel off the bed. He looked up to the two guys standing in the door way and said ‘Hey, you guys want to join us for a drink?’ And just like that they stepped inside and started a conversation. My orgasm was ruined and I just kinda stood there in a fog. 

Bob walked over and rinsed his hands off in the sink and the two guys stepped up to shake my hand and introduce themselves.

My foot still on the bed and boner pointing straight out. I could feel my face go instantly red. Everyone was shaking hands and doing introductions as Bob handed me my shorts and tank. I dumbly got dressed and then we walked out of my room together to go get a beer.

With our two new friends a few steps ahead of us Bob leaned into my ear and said ‘That was totally fucking hot. Can’t wait to finish you off later..” 

The walk to the bar was a blur because my mind was still back in my room thinking about the fact that I just let some dude I just met finger fuck me in front of an open door until two MORE strangers walked in and watched me miss the best orgasm of my life. What?!

Next thing you know we ended up walking right back into the stripper bar I was at earlier. My stripper from earlier instantly made eye contact and started to make his way over to us. He smiled as he approached and was looking Bob and our new friends up and down. The stripper said ‘ Hey! Did yo bring some friends back for another lap dance?”

Bob looked at me and the stripper and I said ‘Hi, maybe in a bit. I didn’t know we were coming back tonight’. The stripper said he would be around and then wandered off. I ended up telling Bob the story and he said he was sorry he missed it.

We made the rounds to a few bars and eventually ended up parting ways with our two new friends. Around 3am we headed back to the resort. The streets were quiet and didn’t have many people walking around. Our resort was on the far end of town and required walking down some long dark streets with sporadic street lights. Bob had been flirty and touchy feely all night. It didn’t feel like my dick ever got soft since my finger fucking earlier in my room. Much more tipsy and hornier than ever I was so ready to get back to the resort and let Bob finish what he started.

About four blocks from the resort on an especially dark block Bob stopped me and leaned me up against a parked truck. He leaned in and started kissing me as he slid his hand down the front of my shorts. Finding my still hard dick he made quick work of unzipping then popping the button on my shorts. The loose short fell to my ankles and in another swift move he whipped my tank top off up over my head. Boom! I was naked with my shorts around my ankles. Dick hard making out with Bob.

Bob grabbed me around the waist and with a quick lift sat me up on the hood of the parked truck. My shorts fell off my feet to the ground taking my flip flops with them. Next thing I know Bob took my rock hard dick into his mouth and started a slow deep throat blowjob that made me lean back to catch myself with both hands. 

It didn’t take Bob long to get me groaning again. I heard a pop and looked down to see that Bob had brought the bottle of lube with us earlier. I watched him squeeze out a hand full of lube as he said ‘ lay back…I thought we might need this..’

Not to be one to pass up a blowjob or hand job I did as I was told. I felt Bob slick up my dick and then another slicked up hand slid between my legs as his lubed fingers entered my hole. He made quick work out of stroking my dick teasing my hole back to where he had me earlier. 

Leaning back on the hood of the truck he said ‘grab your knees and spread your hole for me’. I reached down and grabbed my knees and pulled them to my chest spread wide. Bob kept up the teasing slow hand job but his real focus was back to the slow in and out finger fuck of my hole. Once he had me grunting and groaning again he let go of my dick and circled his fingers around my balls. With a firm grip on my balls he kept the tugging on my balls in rhythm with his finger fucking.

Being drunk, horny and denied an orgasm earlier I was quickly in another world. I heard Bob open the lube bottle again..then I started to feel him use two sets of fingers on my hole. He was doing the slow deep finger fuck but now alternating left hand right hand. With me leaning back holding my knees apart for him…this was the closest I had ever come to being fisted. And I was doing it naked on the hood of a truck on a public street!! 

My dick was throbbing and I couldn’t help the grunts and groans as Bob really got into things. I was riding the ecstasy when the finger fucking stopped and Bob said ‘Sit up here for a sec.” I was like jelly and had to have help sitting up. Bob reached under my arms and lifted me down off the truck to stand on the street. Then he turned me around and put my hands on the hood. Reached down and spread my feet apart and then slid his right hand down my back, into my crack and slid his middle finger into my hole. 

He reached around and grabbed my hard cock with his other hand and started stroking in time with the finger fucking. I was getting close to orgasm but he was keeping me right on the edge. He leaned up into my ear and asked ‘ Do you want to go back to the resort and get this hole worked over real good?’

I groaned and agreed and he said ‘Are you feeling slutty enough to take my dick?”

Oh my god yes! I groaned again and said ‘fuck yes.’ He said ‘ok, let’s go..’ He reached down and put one then the other flip flop on my foot as I held on to the truck for balance. Then he picked up my shorts and shirt and took off walking to the resort. 

That snapped me out of my horny fog and I took off after him dick bouncing and looking around. He was chucking and walking fast saying ‘Keep up! Don’t want to get left behind!’

He was making a point to walk in all the brightest street lights and I was forced to take a zigzag pattern to stay in the shadows of the street.

I didn’t think he would really leave me behind - but it was enough to snap me out of my freshly finger fucked haze. My heart was pumping and I was sticking to the shadows when I heard voices. Coming up quickly behind us on the street was one of those bicycle pedi-cabs. We were only about a block away from the resort but there was nowhere for me to go. I decided to stick to the shadows as the pedi-cab zoomed by. Bob was standing just up ahead at the gate to the resort and wouldn’t you know that is exactly where the pedi-cab was headed. 

I froze in the shadows as Bob started up a conversation with both the driver and the passenger. A few word were exchanged that I couldn’t hear and then all at once they all turned in my direction and started my way. 

After making a circle in the street the bicycle cab headlight swung in my direction and put me in a spot light. I could tell Bob was enjoying every moment from the evil smile on his face. Both the other guys were smiling as well and before you know it they were all 6 feet away. They were all chuckling and the cab driver said ‘ Uh oh! Someone lost a bet!” 

This caught me off guard because I had no idea what he was talking about. Then Bob chimed in ‘ I told them you lost the bet that you couldn’t make it all the way back to the resort without someone seeing you naked.’

The cab driver said ‘ You lost the bet! What’s the punishment?’ I was frozen. Standing in the spotlight trying to hide my boner. Bob said ‘If he lost he had to let me fuck him anytime and anywhere I want for the rest of this week’. 

They all had a good chuckle and the previous passenger said ‘No time like the present! Let us watch!’ My knees were shaking and strangely I was turned on at the same time. I felt like I had already let strangers watch me get finger fucked earlier in my room, then I let a dude finger fuck and blow me on the street. I guess I was capable of anything. 

Bob said ‘Well - we can give you a little preview I guess.’ Then he turned to me ‘ if that is ok with you?’

Oh crap…he was leaving it up to me?

My knees were shaking and I couldn’t get any words out. I just kinda shrugged my shoulders and bobbed my head up and down. That was all he needed. Bob took control and walked over to me. He stepped behind me and then reached around to take both my hands. He pulled them away from my dick and raised them up to my nipples. He got me to take a nipple between each thumb and forefinger and then got me to start tugging on them.

Once he had me working my nipples he reached down and started stroking my cock for our audience. The customer sat back in the cab and the cab driver stayed on his bicycle seat with his headlight pointed at me.

Bob pulled out the bottle of lube and made a show of squeezing some into his hand and then lubing up my dick. With him working my dick and me working my nipples it wasn’t hard to turn back on my slut switch. The guy in the back of the cab unzipped his shorts and pulled his dick out. He started stroking watching the show.

Bob was working my dick and then took a break to lube up his other hand before sliding it into my ass crack. I felt his middle finger slip inside and the whole scene became too real. I was watching the guy stroking his dick. Bob asked the driver ‘Don’t you want to jerk off too?’ 

The pedi-cab driver said ‘naw man - I’m straight, but this is hysterical.’ That just changed the whole dynamic. Bob moved his hand from my dick up to my stomach so he could get more leverage with his fingers that were fucking me through my ass cheeks. I still had hold of both my nipples when Bob said into my ear but loud enough for the guys to hear ‘Put your hands behind your head and spread your knees wider and give me access to that tight hole’. 

I did what he said and realized that my eyes were locked with the straight guy. He was chuckling and enjoying the show. The cab driver asked me ‘Does that feel good?’ All I could do was grunt and shake my head yes.

Without warning Bob said ‘Ok - end of the preview. you guys have a great night’. He pulled his finger out of my ass, grabbed me around the waist with his free hand and walked me past the guys and towards out resort. I was rattled, horny, embarrassed and had been denied yet another orgasm.

I didn’t even think about it as he walked me right through the resort gate and in past the front desk naked and hard as could be. The guy at the desk looked up and welcomed us then checked out my dick as we shuffled past.

I though for sure that Bob would lead me back to my room. But instead he lead me back to his room. Once we were inside he left the door open and started to get undressed. In five seconds he was naked and hard right in front of me. He had pulled out another bottle of lube and a whole box of condoms and tossed them on the bed. He opened the box, tore off a condom, ripped open the package, lubed up, slid it on his dick and then looked at me. ‘turn around, bend over and grab the end of the bed. I did what he said and with out any hesitation he stepped up behind me, squirted lube on my hole..quick finger fuck…squirted more lube on my hole…. two more quick finger fucks then slid his dick in all the way balls deep.

Then he leaned over my back and said ‘You are the sluttiest guy I have met in a long time. I love how turned on you get when guys are watching me fuck your hole.’

With that he started long deep slow fucking of my hole. With a grip on both sides of my hips he started to work my hole that he had been loosening up all night. He would fuck long and slow and then speed up until he was pounding. Then he would slow down and then speed up.

When I didn’t think my knees would hold up any more he grabbed me by the hand, grabbed the bottle of lube, box of condoms and then led us both out of the room onto the balcony. All the guys floating down below in the pool watched us walk out of his room and turn towards the play room. When we got to the play room we were the only ones there. He let go of my hand and climbed up on the platform to sit with his bar leaning against the wall facing the door. Then we said ‘Climb up here and ride my dick’.

This is what I was waiting for so I scrambled up on the platform and went to straddle him. He stopped me and turned me around so I was facing the door too. Then he brought me back wards until my hole was over his dick. 

He lowered me onto his dick and said ‘ Play with your nipples and ride my dick. Don’t cum until I tell you and don’t stop even if someone walks in to watch.’

I did as I was told and started tugging on my nipples and fucking myself on his dick while he laid back and watched. It wasn’t long until the first stranger walked into the room. Bob grabbed my hips and started to thrust up into me. The stranger pulled out his dick and started stroking while he watched us. 

My dick was hard and I wanted to cum so bad that I decided to embrace this new slutty side of me. I was staring right into the strangers face while I rode Bob’s dick. Then another guy walked in. Then a couple. Then more guys. Before long the room was packed with guys watching me get fucked. Most had on clothes..some had their dicks out pumping away.

That was when Bob took it to the next level. He moved me forward into doggie style and fucked me from behind. He waived one of the guys over and told him to play with my nipples. 

This raised the level again. 

Then he rolled me over on my back and started fucking me. The new stranger continued tugging my nipples. 

Then Bob waved another guy over and moved my hand to start stroking the stranger. Then the same on the other side. I was giving two hand jobs, getting my nipple played with and letting Bob fuck me for a crowd.

I was really getting into the scene when one of the guys started shooting on my hand and arm. He quickly moved on an his dick was replaced with a new dick. 

This kept up with Bob directing the scene until he pulled out and walked around to my head. He pulled to the edge of the platform so my head was hanging off upside down. He pulled off his condom and then slid his dick into my mouth and started a slow fucking. I felt him lay the box of condoms on my chest and then he said ‘You want to fuck him? Grab a condom and some lube.’

Before you know it I felt another strangers dick slide in my hole. Bob continued my face fucking while I jerked guys and got fucked by stranger after stranger for what seemed like hours.

The whole time my dick stayed hard as a rock but nobody ever touched it. I was so horny and caught up in the moment. 

At one point Bob pulled his dick out of my mouth and held my head up so I could drink some bottle water. I let go of the dicks in my hand but someone kept pounding my hole. After getting a drink I look to see who the guy was fucking me. It was one of the guys from earlier that watched Bob finger fuck me in my room. 

Bob laid my head back down and slid his dick back in my mouth to start pumping again. This time he was pumping harder and faster. He kept up that pace for a few minutes on my relaxed throat until I felt him stiffen up and then felt his hot cum fill the back of my throat. The next shot filled my mouth as he started to pull out and then he was jerking his dick as his cum shots covered my face. There were comments of encouragement from the crowd and then the guy fucking me was shooting his load filling the condom in my ass.

When they were both done Bob helped me sit up. Everyone was moving around and Bob said ‘Hey sexy, you ready to cum yet?’ I instantly grabbed my dick and started pumping and he said ‘wait wait wait..on sec.’ Then he helped move me around on the platform until I was on my knees facing the door. Everyone had moved to the other side of the room so they all had a great view. Then Bob handed me the bottle of lube and backed off the platform to stand with the other guys and watch.

He said ‘Ok, now cum for us. Keep your eyes open and on me.’ 

I lubed up my dick and started pumping. As I was getting close Bob said. ‘Wait…finger your hole while you cum. We all know how much you like that hole pounded”.

I did what he said without even thinking about it. I spread my knees wide so I could stroke my dick and finger fuck my hole. As I was reaching the edge of orgasm again Bob said ‘I think you let every guy in the resort fuck your hole and cum on you tonight. The rest of the week you don’t have to pretend with anyone. You can can be as slutty as you want. That little slutty hole of yours is gonna be stretched out for weeks so you just became the public sex toy for the resort’

Realizing the scope of what he just said I felt the first wave of orgasm come over me. I shot my first load looking into the faces of the crowd and they all started to clap and cheer. Cum just kept shooting out of my dick pump after pump until the orgasm started to subside. With my hand still slowly milking my dick, covered in sweat and cum I noticed the entire box of used condoms laying around me on the platform. Then I realized it had to be WAY more than was in the box Bob had.

Then I looked back up at the crowd and Bob was all smiles. He walked back over to the platform. Grabbed the bottle of lube and squeezed some on to his hand. 

He reached up and pulled me over until I was kneeling on the platform in front of him. He reached down between my legs and slid past my balls until I felt two of his fingers enter my hole. He started slowly and finger fucking me as he reached up and started kissing me. The kissing and finger fucking continued for a few minutes until I felt my dick starting to get hard again. Bob leaned back from the kiss and said ‘ You keep this up and I may have to marry you.’ 

He said ‘Maybe we could get married on a gay cruise and I could watch you spend 14 days taking a whole cruise ship in this little slutty hole of yours’.