Unexpected Holiday Fun

My previous works have all been related to my experiences in my younger days. This one recalls a recent encounter in my 50's. Although fairly active in my 20's, I never really came out and retreated back into the closet and as time passed became less sexually active to the point where I'd basically given up on ever having sex again.

It's 2024, I have three sisters, two who are happily married with families and one who has the uncanny knack of ending up with guys who are just idiots, layabouts and generally a waste of time.

So after yet another break up, I offered to take her and her daughter on holiday at my expense. All was arranged and then with three weeks to go, she gets back with an ex and wants to bring him along. Absolutely not happening. We argue, she refuses to come, so I have a three seats on the plane and villa in Cyprus to myself for two weeks in August.

I arrive at the villa around 2pm, check in isn't until 4 and there is no one there to meet me so I get out of the sun and sit outside in the shade ready to wait until the owner turns up. I'd been there for about 15 minutes when three guys in late 20's walk down the street and into the next door villa. We briefly exchange nods of the head and then a few moments later, one of the guys returns and asked me if I'm waiting to get into the villa

I respond yes and it transpired that the owner owns both of the villas. The guys have his phone number and call him for me. He tells me the owner will be round in about 20 minutes with the keys and offers me a cold beer which I accept and thank him. He disappears back to his villa and true to his word the owner arrives 20 minutes later.

I unpack my stuff, spend a bit of time by the pool and then head out to explore the area and find out where the bars, restaurants and shops are. I stop off at a few bars for drinks and pick up some food basics, time is now about 8pm and I'm feeling knackered having been up since 2am. I pick up a pizza and head back to the villa.

I eat my pizza and open a lager and put on some gay porn on my iPad. The porn does enough to get be feeling horny and i go upstairs to bed, wank off and crash out for the night.

I wake up next morning about 9:30, glad for the long sleep and with a nice hard on to start the day. Pre holiday I'd treated myself to a skimpy pair of speedos and slip into them. My bulge looks great and I take a selfie to post on one of the websites I'm a member of. I venture out to the pool area, taking in the surroundings. It's perfect, nobody overlooks the garden. The decision is made, I'm going naked for the next two weeks.

The speedos are removed and i set about sorting out my sun lounger and blowing up the airbed, left by the last visitors. Being naked keeps me aroused and I begin a nice slow edging session, ending up floating on the airbed in the pool wanking myself to a fantastic orgasm. I can't believe how being naked outside turns me on and I spend the next four days in a sun drenched wanking fest.

Day five of the holiday, i do a day trip excursion, which was pleasant enough but I missed out on a day of nudity and wanking. Night time, I go out for something to eat and find a bar to drink in. Around 10ish, I move to another bar for a change of scenery and the three guys from the villa next door are in there. I say hello as i walk by them. The bar is reasonably busy and there are no seats and I'm about to leave, when one of the guys waves me over to them and invites me to join them at their table.

I get a round of drinks in and they introduce themselves as Josh, Alex and Ryan. We make a bit of general chat and watch the football playing on the tv. At some point i went off to use the toilet and returned to find just Ryan at the table. I asked where the other two had gone and was told that their taxi to take them into Aya Napa arrived while I away.

"Why haven't you gone? This place is a bit of a family resort, I don't see many single women around, you should have gone with your mates" I said

Ryan smiled and replied " I don't think they'll be looking for girls Mark"

It was probably the drink but I gave him a puzzled look for a couple of seconds before the penny dropped " Oh... yeah, oh ok, sorry i was a bit slow on the uptake there" I half laughed in response.

"I'm a bit pissed off about it, if I'm being honest " Ryan replied " We've been mates for ages, and yes we've played around occasionally but we were all single when we booked the holiday about six months ago. Then about a month ago they announce that there a couple, so I've either got to sack off my holiday or be Mr Gooseberry to the happy couple for two weeks. And I've paid too much fuckin money to sit at home, while that pair play Mr and Mrs on holiday "

Ryan had clearly been annoyed about this but instantly apologised for his rant and just needed to get it off his chest. I was about to get some more drinks when the Elvis tribute act took to the stage. I looked at Ryan and said

" I'm not listening to this." He laughed and replied " Me neither"

We left the bar, it was around midnight and I think we had both had enough and without really saying anything we headed back towards the villas. Ryan went into a mini market close to the villas and came back with two large bottles of lager.

"One for the road?" he asked. " Yeah why not" I replied

As we walked the last bit back, I kept thinking about Ryan fooling around with his mates and wishing I was 30 years younger and started to feel something stirring inside my pants. Mine was the first villa, so we went and sat by my pool and opened the beers. The temperature was still around 27c and very humid. Ryan removed his top and I followed suit making some comment about how hot it was to avoid any misunderstanding that i was trying it on or hoping he'd fancy me

We sat there in shorts and flip flops, just making general chat although I couldn't help taking sneeky glances and Ryans hot body. The stirring in my pants returned again. After about ten minutes Ryan stood up and said "Come on, let's skinny dip"

Ryan dropped his shorts and pants and stood there waiting for me to follow his lead. The sight of Ryan's naked body turned the stirring into a full blown hard on. I couldn't just drop my pants and reveal everything, I hadn't picked up any sexual intentions from Ryan. Why would he be interested in a guy 30 years older than him. The embarrassment would have been too much. He was just a young guy, without any cares happy to go skinny dipping

"Just need a quick pee, I'll be there in a second" I replied as I tried desperately to hide my erection and made my way into the villa. Inside i stripped off and tried to think unsexy thoughts. I managed to droop to a semi hard on and heard Ryan splash into the pool. I sneaked a peek out the door and saw he was facing away from me. I made the short dash to the pool and plunged in. Despite the muggy temperature, the pool had cooled down significantly and this had the desired effect of subduing my hard on.

Ryan grabbed the airbed and we floated around a bit holding onto the side of it, before Ryan got onto it solo. Despite the cool water, Ryan showed no signs of shrinking and his naked body started to turn me on again.

"Your turn he" he said as rolled off the airbed. Nervously, I clambered on, subconscious about revealing my semi erection. Ryan pushed the airbed down to the shallow end of the pool and swam down to me.

"You see our bathroom window up there" he said pointing upwards towards his villa,

"That's where I stand and watch you as you float around wanking yourself off"

I was shocked, I hadn't noticed that window. What i did notice though was Ryan's hand was now stroking my cock.

" I missed watching you today because of your trip out. I bet you haven't had the chance to wank today have you?" he asked

"No" was my mumbled reply aware that I was now fully aroused

"Shall we get out and see if we can sort that out?"

We got out of the pool and grabbed a couple of towels to dry off and then Ryan told me to lay on the sun lounger. He then moved his next to me and began to stroke my cock again. i was sitting half upright, Ryans naked body just inches away from me. I asked Ryan to go slowly as it had been a long time since I'd been with a guy and I wasn't sure how long I'd last. My precum was leaking like a fountain and Ryan wiped it from the tip of my cock and licked it off his fingers before repeating it and feeding me my own precum.

I couldn't believe my luck and wanted the moment to last for ever but I also wanted to shoot my load

"Make me cum. make my cum" I begged

Ryan increased the tempo and a fewer moments later i was ejaculating onto my stomach. He then took my cock into his mouth and devoured the cum that was still leaking out of my cock. My erection finally waned though i remained in a semi aroused state

"Shall we go inside?" He asked. We went in and Ryan told me to stand with my arms out touching the wall, while he groped my arse and cock, occasionally rubbing his hard cock up and down the crack in my arse before telling me to "Go and sit on the sofa"

I did as instructed and Ryan came and stood in front of me, it didn't take a genius to work out what he wanted and i set to work on sucking his 6" inch hard cock. sitting on the sofa wasn't the best position so I dropped down onto my knees and continued to devour his cock. I felt Ryans hands around my head as he began to fuck my mouth. I still kept thinking wow is this really happening?

Ryan finally pulled his cock out of my mouth and I excitedly waited for him to blast his cum all over my face. To my surprise he just stepped away put on his shorts and flip flops and said "Back in a couple of minutes "

I was confused, what was going on? Was he going because my blow job hadn't made him cum? A few minutes later he returned, clutching a small bag. I looked at him confused and then he spoke

"Would i be correct in assuming you didn't pack condoms and lube?"

"Yes, didn't think there'd be required" I replied

"Well somebody thought wrong then didn't they " Ryan replied with a huge grin on his face. I walked over to him and passionately kissed him, our tongues exploring each other's mouths. My cock was hard again and I held Ryan tightly squeezing my cock up against his muscular legs. I broke off our kiss and moved back slightly. I noticed that id leaked precum onto Ryan's shorts. I quickly put my hands inside his waistband and pulled them to the floor.

Ryan's semi erect cock sprung free and i led him to the sofa this time, sat him down and parted his legs. Kneeling down, I grasped his cock and quickly slipped my lips around it again, it didn't take long until I could feel Ryan was fully hard again. I was sucking on Ryans cock and wanking myself at the same time. Ryan saw this and told me to stop wanking and he would be the one who would make me cum again.

"Come on let's go upstairs " Ryan said.

I stood up and started to head up the stairs, followed by Ryan. About halfway up Ryan spoke

" Stop there, put your hands on the steps and bend over so I can see your arse"

I did as instructed.

"Mmmmm, very nice. Spread your cheeks, I want to see how tight your hole looks"

Again I did as as instructed and felt Ryan rubbing his finger up and down my crack and then pressing on my hole. I tried to relax and felt Ryan inserting the tip of his finger into me.

"Ohh, fuck yes" I moaned

"Get up them stairs, you horny old fucker" He said laughing

into the bedroom we went, I hadn't switched on the air con so the room was hot and sticky. I lay on the bed in anticipation of what Ryan was going to do to me. He got astride me and began to suck my cock before manoeuvring himself into a 69 with me. I lasted about 30 seconds before begging him to stop as i was close to cumming. We broke off our 69'ing and lay next to each other just kissing. Ryan said it was ok for me to continue to fondle him but he wouldn't touch me as he didn't want me to cum yet. Just the kissing alone with the gorgeous guy kept me very close to the edge but eventually I managed to calm myself and back down a little from blowing my load.

We were both sweating like crazy now and after about five minutes of kissing and hugging Ryan spoke

"You ok now? You're not going to cum yet are you?"

"I'll do my best not to" I replied " but it's probably best if you don't touch my cock for a bit" I added.

I thought to myself what kind of guy says he doesn't want another guy to play with his cock? but I knew it had been so long since id last been with a guy it wouldn't take much for be to boil over and as much as I wanted to cum, I also wanted to make the most of the moment. Thankfully, I think Ryan understood the situation and temporarily kept away from my cock.

"That's cool Mark" he replied " Why don't you bend over and show me that hot arse again"

I stood up and moved to the end of the bed, spread my legs a little and leant forward with my hands touching the bed. Ryan repositioned himself behind me and again initially groped my arse before beginning to rub his fingers up and down my arse crack and caressing my hole. He temporarily stopped and and I heard a rustling as Ryan got something out of the bag.

He gently kicked my legs slightly further apart and then I felt the cold sensation of lube being worked into my hole by Ryans finger. I moaned with pleasure as he gently fingered me. More lube was applied and a second finger made its way inside me and finally two fingers and a thumb. This was more than I could take in the standing position and I collapsed onto the bed on my hands and knees with my arse sticking up.

"You ready for some cock?" Ryan asked

"Oh fuck yeah, gimme it, fuck me, fuck me now " I replied, desperate to have my arse filled.

I felt the tip of his cock at my entrance and then felt the first couple of inches enter me. Oh my god, how I'd missed this feeling. Had it really been 20+ years since I'd last been fucked. Sadly the answer was yes but the old instincts returned. l knew the burning sensation would pass and be replaced by the wonderful full feeling up inside me. l relaxed and Ryan was able to fully penetrate me. It felt great to have my arse stuffed again.

Ryan held his cock deep inside me until I gave him the ok to start fucking me. Slowly at first before building up the pace, slamming back into me, feeling his thighs slapping against my cheeks. My cock was leaking like a fountain now. At some point Ryan pulled back to far and his cock slipped out. l fell forward onto the bed, glad for the temporary respite from the pounding Ryan was giving me.

The respite was short lived as Ryan rolled me over onto my back, spreading my legs apart as he lubed me up again and began fucking me again. I couldn't hold on anymore. My cock began to twitch and the hands free orgasm started. My cum was beginning to flow and Ryan started furiously wanking me while still fucking my arse. I must have shot five or six loads of hot cum onto my chest. I couldn't believe id managed this considering it was less than an hour since Ryan had wanked me by the pool. I guess when you're my age getting fucked by a young guy, the horny feeling really takes over.

Ryan was now furiously banging away at me as I continued to moan with pleasure. Ryan was now moaning hard as well and I knew he was close to cumming. I wanted to feel his hot cum inside me

" I want you to cum in me " I begged him. Ryan pulled out and whipped off his condom, quickly wanked himself and shot his load over my cock, balls and gaping hole before repositioning himself and to fill my mouth with his still hard cock, allowing me to suck out and swallow his remaining cum.

We were both literally dripping with sweat and Ryan again suggested skinny dipping to cool off. This time there was no embarrassment on my part as we headed back down stairs. Ryans cum was dribbling down my legs by the time we made it to the pool.

We cooled down and I got onto the airbed and Ryan stood next to me and we began to kiss again. I thanked Ryan for giving me my first fucking in at least twenty years. The kissing had already started to get me aroused again and Ryan again started playing with my cock.

"How do feel about having your second fuck in twenty years?"

"Oh fuckin hell, yes. That felt so good. I can't believe how horny your making me"

We quickly dried off for the second time and headed back up to the bedroom. I was fully erect by the time we got there in the anticipation of the fuckin i was about to get. Ryan was in a semi aroused state and I began wanking him before taking his cock back into my mouth until i could feel he was fully hard. I stopped sucking and moved fully onto the bed, lay on my back, pulled my legs up and apart and offered my arse to him

Ryan lubed me up again and inserted a finger into me. I think with the ease I took his finger, he knew i was ready for his cock again. Ryan reached for the bag and pulled out another condom to put on. I looked at him and said

" You don't have to, if you don't want to"

He looked at me and replied "Are you sure?"

I nodded back at him.. I wanted to feel his cock inside me and for him to fill me with his cum. He spread my legs a bit wider apart and slid his cock deep into me again. Having just cum less than half an hour ago, seemed to give Ryan the ability to fuck me forever. I lost count of how many positions he put me in before finally finishing me off doggy style, pumping my hole full with an unbelievable amounts of cum.

I collapsed face down from the fucking I'd taken. Ryan got me to roll onto my back and began to wank me off with one hand whilst fingering my cum filled hole with the other. Despite being as horny as fuck, I wasn't sure if I'd be able to ejaculate for a third time. However Ryan continued to wank anf finger fuck me and gave me the most amazing orgasm. It was actually quite painful I only managed a few dribbles of very watery cum but the intensity of the orgasm was unbelievably as my cock twitched and pulsed as I tried to shoot out a non existent load. I felt my whole body spasm at one point.

Well and truly fucked, I fell asleep next to Ryan. I awoke in the morning and he wasn't there. I lay in bed till around ten before getting up. Next door was quite and I assumed the lads had gone out for the day, so I spent a peaceful morning and early afternoon naked sunbathing.

Around 3pm the silence was shattered by the sound of kids jumping into the pool next door. I realised Ryan and his mates had left. I scampered back inside and put on a modest pair of swim shorts before returning to the sun lounger and pool and relived the memories of the previous night. Later that day I called the sister who I'd argued with to make up with her but secretly I couldn't have been more happy she wasn't there.