The Gay-Cation

‘Jack,’ Simon put his hand under his chin and lifted it, so he was looking him in the eyes. ‘I think it’s time I fucked you, give James here a preview of what’s to come.’

Jack quickly got to his feet and went searching for the lube to get his ass ready. That gave me some one-on-one time with Simon, and I made sure to take advantage of the couple of minutes I had. I sucked his cock for a little while before standing up and letting his cock rub against my ass. I bent over, exposing my hole to him and felt him rubbing his cock up and down the crack of my ass. Jack, meanwhile, was ready. He had discarded his thong, and had made a pile out of all our clothes to lift his ass off the beach ever so slightly. He was now on his back, his legs spread, and Simon was ready.

‘What are we saying boys, condoms or no condoms?’ Simon said, we all quickly agreed no condoms and Simon walked over to where Jack was, dropped onto his knees and positioned the head of his cock at his hole, ready to penetrate him. He lifted one of his ankles onto is shoulder and spread Jack’s other leg wide. As he pushed himself inside, it was obvious that Jack was accustomed to taking his cock. There was little resistance and he quickly pushed himself balls deep as Jack started to moan. I laid down beside them and watched this beautiful act take place in front of me. I watched intently as Simon’s cock slid in and out of Jack’s hole with ease.

‘I love your big cock,’ Jack moaned as he took whatever Simon could give him.

I leaned over and started to kiss Jack, feeling kind of left out, I wanted to be involved. I wanted to be the centre of both their attentions. As he kissed me, he moaned into my mouth, and I reached down for his cock and slowly started to stroke him back to life till he was fully hard.

‘I think you should sit on his face James, let him get your ass nice and wet,’ Simon butted in.

I didn’t see any reason why I shouldn’t, so I let go of Jack’s cock and swung my leg over his head, so I was almost sitting on his chest. He freed his arms from in between my legs and I shuffled back slightly so I was nearer to his face. I felt him press his face against my ass and then his tongue started to work its way around my ass. Immediately my cock was twitching inside the jockstrap and then I felt Simon’s large hand around my neck as he pulled me forward so I could kiss him. He broke off the kiss and I locked eyes with him and all I could think about was having his cock inside me.

‘Your tongue feels so good on my ass,’ I told Jack as I started to jiggle my ass up and down causing his tongue to hit all different parts of my ass and taint. I reached forward and grabbed Jack’s cock once more, this time though I moved myself down on top of him so I could take him into my mouth. I was soon bobbing up and down on his cock with a perfect view of Simon’s cock sliding into his ass.

‘I hope you’re saving that load for me,’ I said to Simon, whilst stroking Jack’s cock.

‘It’s not just my load you’re getting,’ he smiled. ‘We both plan on filling you up before you go.’ I went back to sucking Jack’s cock and Simon encouraged me with hand on the back of my head to make sure I kept taking him deep.

‘How long till I get to feel a cock inside me?’ I decided to be bold, it felt like I’d waited and watched for long enough.

‘Are you ready for him Jack?’ Simon said, Jack muffled a response, but it sounded enough like a yes, that Simon pulled his cock out of Jack’s ass and sat back and started to stroke himself slowly.

‘Where do you want me?’ I asked Jack as I climbed off his face, even though I could’ve stayed there all night but the need for a cock inside me overruled that feeling.

‘Stay on all fours,’ Jack told me as he climbed up onto his knees and reached for the lube.

He rubbed a generous amount on my ass and slid a finger inside me. And now he started to finger me, exactly how I would finger Heather before I fucked her. He quickly worked his way up to two fingers and was really pushing them deep inside me, brushing against my prostate every time. My head rocked back, enjoying every second until Jack had me begging for his cock.

‘Please fuck me,’ I begged him. ‘I need to feel you inside me.’

Thankfully, he didn’t deny me any longer and I soon felt the head of his cock pushing against my ass. He pushed forwards and my ass opened for him so he could push himself inside. Once the head of his cock pushed past my sphincter I was in heaven. Jack kept edging himself further inside me until I felt him press his body against mine. Jack slowly started to rock backwards and forwards until my ass was ready to be fucked. Once he was able to enter me more easily, he started to pick up the pace and was soon fucking me harder. His balls were soon slapping against my body, and I was just there, gripping onto the picnic blanket with my face buried in it as I just moaned. I knew my cock wouldn’t be hard but that didn’t take anything away from the pleasure I was feeling.

Soon after Jack really started to fuck me, I felt Simon appear in front of me. He pulled my head up gently so I was eye level with his cock, and he just said, ‘suck it’, and waved his cock around in front of my face. When it stopped moving, I opened my mouth and managed to get it into my mouth and start sucking. I couldn’t use my hands, because I panicked and thought Jack would knock me off balance while he was fucking me.

‘What a perfect evening,’ Simon moaned. ‘We hit the jackpot finding this one. I didn’t think we’d have him spit roasted this quickly.’ They high fived above me, and it turned me on, thinking that I was some sort of conquest for these two. They’d obviously seen me about and had chosen me for tonight.

Jack took a tight grip on both my hips and started to fuck me harder, and I was now just moaning around Simon’s cock as he continuously rubbed his fingers through my hair. He was really slamming himself inside me now, almost like he was trying to force himself to go deeper, even though I don’t think it was possible. ‘I love fucking a tight ass,’ Jack moaned. ‘He’s fucking milking my cock.’ I started to meet his thrusts, not that I wanted him to cum early, but I wanted to push him to the edge. I wanted him to be on the verge of cumming and I knew he must’ve been getting close. He kept trying to slow the pace, but I wouldn’t let him.

‘Fuck, fuck, fuck,’ he grunted before quickly pulling his cock out. ‘I can’t, otherwise I’m going to cum.’

Simon laughed, ‘looks like I need to step in then,’ he let his cock fall out of my mouth. ‘I think you should ride me first.’

I stood up whilst Simon got himself onto his back, his big, thick cock standing to attention. I made sure to lather him in lube before doing the same to myself and then started to lower myself down. ‘Take your time,’ Jack told me as he held Simon’s cock steady as I lowered myself down until I felt the massive head of his cock trying to invade my ass. It took a couple of attempts of slowly lowering myself down until finally his big cock pushed past my assholes resistance and entered me.

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