I yelped slightly at first, ‘fuck it’s so big.’ As soon as I had enough of him inside me that I could start riding him, Jack let go of his cock and held my hands, providing me with some much-needed balance. I started slowly bouncing up and down, trying to take more of Simon’s cock each time. I could feel my hole stretching to accommodate his girth. Whenever I took more of him inside me, I would take some time adjusting to his cock before lowering myself down again.
‘Big, isn’t it?’ Jack said with a big smile on his face.
‘It’s fucking huge,’ I moaned. And after what felt like a lifetime, I felt my ass cheeks land on his body, meaning I’d taken his full length inside me. ‘Ohhhh fuck,’ I let out a long moan.
Now I had him fully inside me, I started to grind myself on his cock, feeling him rub against my prostate which had me in heaven. As Jack held onto me, I started to bounce, the noise of our bodies meeting started to get louder, and so did my moans. His cock just felt so good inside me. I was starting to wish I’d done this a lot sooner. Simon had let me have full control for now, but I don’t think he was used to that, and I think he wanted to take more control. He had me reposition myself, leaning back and placing my hands either side of his body so he could start to fuck me. I felt his hands grab onto my hips shortly before he started to drive his cock inside me. My own cock started flapping around my body, but Jack made the quick decision to muffle my moans by standing above me and feeding me his cock. I started sucking, and moaning all over his cock. Simon’s continuous driving into my ass had me feeling all kinds of strange feelings. I had a mixture of feeling like I was going to cum or pee. And I didn’t want to let it go in case it was the latter.
Eventually, after the constant pleasure to my prostate, my legs turned to jelly, and I could no longer hold myself up. I collapsed onto Simon’s cock, driving it deeper inside me to the point I had to climb back off because he went a little too deep. I had to lay down to catch my breath, but Simon wasn’t interested in any sort of break. He quickly had Jack on all fours and was fucking him from behind making him scream with pleasure.
I watched them fuck for what felt like an eternity. It gave me time to recharge my own batteries, and I played with my own cock whilst watching Jack get fucked like a rag doll. Hopefully one day, that’s how I’ll be getting fucked, but it still may be too early for me. By the time I was ready to join back in, Jack had been flipped over and was getting fucked in the missionary position again. Simon had his hand wrapped around Jack’s cock and was slowly jerking him off, and Jack was enjoying every second. Maybe a little too much, he looked like he could cum at any moment and slapped Simon’s hand away.
‘James, sit on his cock while I’m fucking him,’ Simon told me. ‘It won’t take him long to fill you up.’
It took some figuring out, but Simon released Jack’s legs as much as he could until eventually, I was able to climb on top of Jack with my back to Simon and started to feel around for Jack’s cock before finding it and lining it up with my hole. It slipped in with ease this time and I started to ride him while Simon got back to fucking him. I bent over so I could kiss Jack whilst I did my best impression of twerking on his cock until he started to warn me that he was going to cum soon. I sat back up and put all my efforts into bouncing on his cock. Simon wrapped his arm around me from behind and started kissing my neck.
‘Fuck,’ Jack moaned. ‘I’m cumming.’ As I bounced on his cock, I watched as Jack started to squirm before his cock started pulsing inside my ass and he started to fill me with his cum. The warm feeling of his cum inside me, almost made me reach for my own cock to make myself cum but I still had Simon’s cock to think about. Once Jack had finished cumming, I climbed off him and his cum immediately started to leak from my ass. And I’d now decided that cum leaking from my ass was the best feeling in the world.
When I stood up above Jack, Simon immediately pulled my jockstrap down my legs and threw it away to the side. Jack rolled away and Simon had me lay down on my back. One of my legs was spread wide and Simon picked the other one up and rested it on his shoulder. He put some more lube on his cock and pushed himself inside me. I immediately felt that wave of pleasure and my cock showed it as a trail of pre cum started to appear at the head of my cock. I gripped onto the blanket and threw my head back.
‘Oh fuck,’ I screamed. ‘I need to cum soon, this feels to fucking good.’
‘Nearly there,’ Simon replied and quickened his pace. He was really slamming himself inside me now and soon started to breathe heavily and I could tell he was close.
‘Fill me up, please,’ I screamed at the top of my voice.
‘Arghhhhh, fuck,’ Simon moaned, and he thrust himself deep inside me one last time before he held himself there and I felt his cock starting to pulse. And it must’ve pulsed at least 6 or 7 times before it stopped. He then withdrew his cock from inside me and Jack practically jumped headfirst onto my crotch and took my cock into his mouth.
He swirled his tongue around the tip of my cock, and after everything I’d been through tonight, that was all I needed. I started to squirm and writhe on the blanket as I filled his mouth with cum. He continued to suck me until I couldn’t take it any longer and had to stop him. We all took some time to recover before sharing one last kiss and going our separate ways. I immediately headed back to my room, showered, and climbed into bed.
I slept and I slept well. Turns out being fucked can really make your tired. I didn’t wake up till noon the next day and had already missed half of my last full day. I climbed out of bed, showered, cleaned my ass, and then got dressed to head down to the pool for some snacks and a cold drink. I checked my tan lines out in the mirror, and they looked like they were coming along slightly. I was going to go back home looking like I’d barely seen the sun. So, when I got ready, Alvaro had bought me one thong swimsuit, so I put that on, covered it with some shorts and went on my way.
I’d been around the pool for a little while and received some admiring looks from passers-by as I laid there in my thong with a little bulge showing off my cock. Not sure how many people checked me out when I was laying on my front, but I was hope there was more than a couple. After a while, I made my way over to the pool bar, ordered an iced drink and some snacks. As I sat quietly eating my snacks, a familiar Irish accent appeared from behind me.
‘Knew you wouldn’t survive,’ the voice said, and I turned around to see Paddy walking towards me, dressed in a t-shirt and jeans.
‘I’m saying nothing,’ I smiled and then said, ‘I don’t know what you’re talking about.’
Paddy laughed, ‘you’ve probably had more cock than I have on this holiday.’
‘There’s still time for you to catch up,’ I said jokingly.