The Night Out

I spun to face him and smiled in an apologetic way; I didn't want him to feel left out. I reached for the buttons on his trousers and soon had them around his knees as well. Underneath he was wearing a pair of white briefs which were straining due to his hard cock. He'd clearly enjoyed me playing with Jayden's cock. And he looked bigger than Jayden. I pulled his briefs down but had to reach in and grab his cock to prevent it getting stuck inside the briefs. It was bigger than Jayden's cock. Oli must've been around 8 inches and he was thick too. Suddenly, I was seriously nervous. I stroked his cock as he ran his fingers through my hair, and I turned to see that Jayden was stroking his own cock. I spent the next few minutes solely focusing on Oli and his cock. I ran my free hand up and down his legs whilst I stroked his cock which felt like it was getting harder.

I then grabbed Jayden's cock so that I was now stroking them both at the same time. I felt like such a slut, and I hadn't really done anything yet. I looked up to see them both smiling at each other, and it made me smile. And then they started laughing, 'what's so funny?' I asked them.

'We were going to have a bet about you when we first saw you in the bar,' Jayden said.

'And what was the bet going to be?' I enquired.

'What were the chances of us being able to take you home with us,' Oli said.

'And who won?' I smiled.

'No-one, we decided it wasn't a fair bet because we knew you'd definitely be coming home with us before we'd even spoke to you,' they both laughed, and I blushed.

After they'd stopped laughing, Jayden looked down at me; 'would you like to try sucking our cocks?'

When I looked at them both, I licked my lips without even thinking which prompted Oli to say, 'start with Jayden's, it'll get you used to having something in your mouth before you try mine.' I turned on my knees, so I had my back to Oli and took Jayden's cock into my hand and moved myself up slightly off my knees, so my head was level with his cock. I watched his cock as it twitched slightly, and my mouth went completely dry as I lifted his cock and licked the base right next to his balls, all the way to the tip.

'Oh fuck,' Jayden moaned. 'That's a good start.'

I continued to use my tongue to lick his shaft, then rotating what I was doing to lick around the head of his cock, making sure to pay extra attention to the tip. In my head, a thousand different things were going on, but all I was doing was trying to think of what I would like if someone was sucking my cock.

'You're moving quicker than I thought,' Oli said from behind me. 'Do you want to try putting it in your mouth?' I continued using my tongue even after what Oli had said. And when I pulled back, I kissed the head of his cock and I felt Oli put his hand on the back of my head and Jayden started to push forward. I didn't resist as I opened my mouth and felt Jayden's cock resting inside my mouth. It was a strange feeling at first, but I soon got used to it as I let him work his cock in and out on his own, taking more of him every time until my nose was pressed against his body. He pulled his cock all the way out of my mouth, but we were still connected thanks to a giant string of saliva as I got my breath back.

'His mouth is perfect,' Jayden said to Oli like I wasn't there. 'I think he was born to suck cock.'

'I bet he was born to be fucked by cock as well,' Oli laughed. 'But we'll find out later about that one.'

They continued to have a conversation above me whilst I sucked Jayden's cock. Sometimes Jayden would moan when he was talking to Oli, so I still knew I was doing a good job with his cock. I could hear parts of their conversation as they discussed earlier guys they fucked. My ears would prick up at certain words but for the most part I was focused on his cock. I was now building my own steady rhythm, one hand on his shaft whilst I took the rest of his cock into my mouth and swirled my tongue around it. This was when I was getting the biggest response from Jayden. He grabbed my head, moaned, and started to fuck my face.

'James,' Oli said with a raised voice from behind me. 'I'm starting to feel a bit left out here.'

I let Jayden's cock fall from my mouth and turned towards Oli, 'sorry, I got distracted,' I said as I wiped my face dry.

'You were really enjoying that, weren't you?' He said with a smile.

'Yeah,' I replied as I moved closer to him and took his cock into my hand and instantly remembered that he was a bit bigger than Jayden was, who was now sat on the sofa stroking his own cock, with his clothes in a pile at his feet as I got ready to pleasure his partner.

'You can start with the balls if you want,' Oli advised. 'I love it when someone sucks my balls.'

I took his advice, who I was to do anything other than what he wanted. I was still learning about how to pleasure another man. I didn't even know if I knew how to suck another man's balls. Luckily, Oli was well groomed downstairs, and his balls and cock were hairless. If they weren't, it was something I probably would've hesitated to do. So, I lifted his cock upwards, and exposed his balls to me. I moved my head underneath his cock and started to lick around his balls which he at once moaned his approval.

Not fully confident on what to do next, I took one of his balls into my mouth and sucked on it gently. He didn't disapprove or try to stop me, so I did the same thing with the other one and he continued to moan. I looked up at him and he was playing with his own nipples as I pleasured him. Then I licked him all the way to the top of his cock before taking him into my mouth without hesitation and tried to suck him to the base, but I struggled. He was just that little bit bigger and thicker than Jayden and I just couldn't get all of him into my throat on the first try. But I wasn't going to fail. I placed my hands on his ass and brought him towards me while keeping his cock in my mouth. I did everything I could not to gag and soon had my nose pressed against him.

'Oh shit,' he moaned. 'No first timer has ever been able to do that to me.'

I was now feeling so much more confident. So, I picked up the pace that I was sucking his cock. Working my hands on his shaft in double quick time, and swirling my tongue around the head of his cock and shaft, making sure I felt every vein on his cock. I imagine there was some strange noises coming from my mouth when it was full of cock, but no one said anything or reacted to it. I pushed his jeans and briefs down to his ankles and he started to step out of them as I continued to play with his cock.

'Oh my god,' Oli moaned. 'This feels so good, but we have so much more we want to do this evening.'

'And what might that be?' I asked cheekily.

'Well, I need to stretch that pretty little ass of yours before I fuck you,' Oli said with a smile. 'That's if you still want it.'

'Mmmm, I don't know,' I faked my unsureness. 'Of course, I want you to fuck me.'

'Jayden, why don't you go and get the bedroom set up,' Oli said as I took his cock back into my mouth. Jayden jumped up off the sofa, his hard cock bouncing in front of him, and he disappeared off into the bedroom whilst Oli started to moan again.

After another few minutes of me sucking his cock, Oli pulled his cock out of my mouth, and I followed him with my mouth wide open, wanting more of him. 'Easy there cockslut', he laughed. 'I think it's time for us to move this to the bedroom.' He put out his hand, which I took, and I stood in front of him, and he kissed me. As he was kissing me, he reached for the towel, which was tenting out in front of me because of my rejuvenated cock. The towel was quickly removed from my waist, and Oli reached down and grabbed a hold of my dick. 'I could use that to pull you into the bedroom if I needed to,' he laughed again. 'But I'd rather see your ass walking away for me.'

I took that as a hint, and set off on my way towards the bedroom before I felt a hand on my shoulder. 'Not so fast,' Oli said. 'Bend over for me.' I bent over slightly and leaned on the arms of the sofa as I felt Oli slide his hand down across my back and onto my ass cheek. He ran his finger down the middle of my ass and stopped to let it rest against my asshole. He pushed gently and I moaned, before he pulled away, gave my ass a stinging slap and walked off towards the bedroom with Oli at my side and his hand on my ass. Which was a strange feeling I might add.

As we walked into the bedroom, I hadn't realised just how big the bed was, there was enough room to have three of four people sleeping in there and you wouldn't have been uncomfortable. The mattress was quite high, but looked like that was designed for a specific reason. As Jayden stood next to the bed, he was at the perfect height for fucking someone who was laid on the bed. The bedsheets had been covered by a large blanket and by the side of the bed, on the bedside cabinet were the condoms and lube. Suddenly, things were starting to become very real. Oli closed the bedroom door behind us and then stood behind me and gently started to kiss my neck.

His hands were roaming all over my body as he kissed me before they eventually landed on my cock, and he gently stroked me. Jayden finished putting things out ready for sex and walked towards me. Oli let go of my cock and focused his attention on my ass, grabbing and spreading my ass cheeks. Jayden kissed me on the lips, Oli lifted my arms and wrapped them around Jayden's neck as his hand worked its way to my cock. I spent the next few minutes as the meat in this hunky man sandwich. Jayden and Oli eventually started kissing to the side of my head, and I could feel Jayden's hard cock pressing into my stomach and Oli's cock pressing into my ass.

When the kissing eventually stopped Jayden spoke to Oli, almost like I wasn't stuck in between them, 'do you think we should start prepping his ass?' Oli smiled at that and agreed that it was time. I was walked over to the bed before being spun around and pushed gently onto the bed, so I fell onto my back.

Jayden stayed stood up in front of me while Oli climbed onto the bed and was kneeling next to me. 'This is where we work as a team,' Oli said as Jayden began massaging my legs and Oli massaged my chest. My heart was beating a million times a minute as I let myself feel vulnerable and exposed to them both. None of this felt wrong to me, if anything it felt like this was meant to be. Maybe me and Oliva splitting up was going to be the best thing that happened to me? A chance for me to do some self-discovery. 'You see,' Oli continued, 'Jayden is going to get you nice and relaxed, and once he's done that, I'm going to get you ready to take some dick, sound good?' I nodded but my voice seemed to desert me.

I tried to relax as much as I could. I was staring at Oli's cock which was twitching next to my face as Jayden started to lift my legs into the air and spread them. He placed his hands on the backs of my legs to keep them in the air, until Oli positioned himself behind my head and held me by the ankles. Jayden started to gently caress my legs, kissing them, and eventually reaching forward so he could lick my cock, from the tip to my balls and then my taint.

'Oh fuck,' I moaned. 'That feels good.'

'He's just getting started baby,' Oli told me. 'Just lay back and let him work his magic.'

He seemed to focus on my taint for a little while, then splitting his time between my balls and just above my asshole. I moaned ever so slightly and then I felt his wonderful tongue on my asshole. A warm feeling surged through my body which helped me relax. He was using his hands to spread my ass cheeks as well, giving him even better access to my virgin asshole. I started making noises I didn't know I could make. He was eating my ass good, so good. I could feel myself opening for him. My asshole was twitching.

'Shit, he's licking my ass, oh fuck,' I moaned. 'This feels so fucking good.' I gripped onto the bed and Oli held me still as I started to squirm. It didn't feel like Jayden was taking a break to catch his breath. He just kept going and going until I was a moaning mess. Jayden was slowly rolling one of his hands over the head of my cock which only made me move about more.

Oli positioned himself to get a better look, which meant that his cock was now to the side of my head. I turned and couldn't resist. I took the head of his cock into my mouth and played with his balls with one of my hands. With my other hand, I reached down and ran my fingers through Jayden's hair. I felt like such a slut, but the thing is, I was loving life. Oli was now moaning as well, as tongue twirled around the tip of his cock, and I was moaning on his cock as Jayden continued to work my ass. My ass felt super wet, and Jayden then pressed his finger into my ass, and I moaned even harder onto Oli's cock.

'I think he's ready for the next part,' Jayden said to Oli whilst the tip of his finger was still inside my ass.

Oli moved off the bed, his cock leaving my mouth and me whimpering as he did so. I felt empty whilst they moved around. My legs touched the ground again and I played with my own cock until Oli was now on his knees in front of me after picking up some lube from the counter. Jayden now positioned himself next to me and I soon had his cock in my mouth as Oli started to spread some lube around the entrance to my ass.

'Oh fuck, that's cold,' I laughed.

'Trust me, it'll be worth it in the end,' Jayden said as Oli continued to coat my ass in lube. I then felt Oli dragging his finger up and down my ass, spreading the lube around my asshole before he gently pushed himself inside me. I moaned around Jayden's cock as Oli slowly worked all his finger inside me, before then withdrawing it again. When he pulled his finger out, I felt my asshole twitch slightly as I waited for the next time.

Oli didn't keep me waiting long and this time he fingered me like I would have fingered Olivia. Slowly he buried one finger as deep as it would go and then pulled it back out, but not all the way. Then he pushed it back in again but this time it was quicker. I let Jayden's cock fall out of my mouth as I couldn't focus on him whilst this was happening. Jayden then climbed off the bed and disappeared back into the living room. At a certain point, his finger would rub gently past my prostate which made me whimper and moan.

'Oooo,' Oli said with a big smile. 'I think I've found your pleasure button.'

My cock stayed hard while he worked my ass and Jayden was soon slapping my face with his own cock, and I couldn't resist playing with him. I hadn't even realised he'd come back into the room and in his hand, he had my phone.

'What are you doing?' I asked him as he held it in front of my face so it would unlock.

He turned it onto the camera, 'I just thought you'd like some memories of your first time, but I can stop?'

I thought about it briefly, and the thought of being recorded turned me on. 'As long as you don't try and send anything to anyone, then yeah I'd like some memories,' I smiled.

'It's for your eyes only,' he said. Then I saw him hit record and point it over my body. Oli continued to push his finger against my prostate and my cock twitched every time. I moaned and whimpered, and Jayden was presenting his cock to me again and I had to taste him. He was soon deep in my throat. I wanted to reach down and jerk myself off, but I didn't want to bring things to a premature end. The next time Oli withdrew his finger, he pushed himself back in again just with a lot more pressure. I could feel my ass stretching as he used two fingers to open me up, and I moaned loudly around Jayden's cock.

'He's taking it so well,' Oli said. 'I can't wait to see him with a cock inside him.'

The stretching of my ass continued for another 5 minutes or so. As he continued, he fingered me faster and faster. The noises I was making and his hand slapping against my ass when his fingers were buried deep inside of me were filling the room. I stopped sucking Jayden's cock and looked down at Oli who was just smiling at me. My own cock was leaking pre cum, a tiny puddle had formed around my belly button.

'That's so fucking hot,' Jayden said above me. 'Do you think he's ready?'

'Oh, I think he's ready alright,' Oli laughed. 'Do you think you're ready?'

'Yes, I'm ready,' I moaned as his finger pressed against my prostate again.

'What are you ready for?' He teased me.

'I'm ready for you... oh fuck... to fuck me.' I stuttered out.

They both laughed, 'I bet you didn't think you'd be saying that tonight, did you?'

I shook my head to say no, and Jayden jumped off the bed and was quickly rolling a condom onto his cock and covering it lube, and then some more lube. He finished it off with some more lube. You know what they say, there's no such thing as too much lube. He smothered some lube onto his fingers and approached where Oli had just been, but he was now climbing onto the bed and moving so he was next to me.

Jayden took the lube that was on his hands and rubbed it around my ass. I was getting used to the cold feeling now, and the sensation of having somebody else playing with my ass. Once he thought he'd spread enough lube, he lined up his cock with my hole. Oli was now kneeling above my head, his cock hanging over my head as he held me by the ankles and spread my legs, presenting my hole to Jayden.

'You ready to lose your virginity?' Jayden asked me, with the tip of his cock resting against my hole.

I looked at Jayden and nodded and felt Oli's cock hit the side of my face. Jayden started to push forward, slowly at first. He held his cock in one hand and placed the other on my chest. He kept telling me to relax. There was an initial burst of pain, then slightly more pain when his cock pushed past my sphincter and I let out an almighty moan, which was more a sigh of relief. The pain subsided immediately.

'This hole is so fucking tight,' Jayden said as he continued to push himself inside me slowly.

I could feel my asshole stretching even more to accommodate his cock. There was no pain, Oli had prepared me expertly and I was able to just lay back and enjoy the feeling. Soon, the entire length of his cock was inside me. He moved his other hand so that both were now on my chest and pulled his cock out of my hole before pushing it back inside me. I moaned again as his cock brushed against my prostate. Jayden was quickly into a rhythm of fucking me, and his cock was sliding effortlessly into my hole.

'How does it feel to have an ass full of cock?' Oli asked from above me, his hands still wrapped around my ankles.

'It feels... ugh... fucking good,' I moaned and wrapped my arms around his thighs and started rubbing them.

'You look so hot with a big cock in your ass?' Oli told me and I moaned as Jayden thrust deep inside me again. 'Would you like some memories to take away with this?'

'Yes... fuck... please,' I moaned. I think I was cock drunk; I didn't know what they'd do with the photos.

Oli let go of my legs, and Jayden took control of my ankles instead as I watched Oli walk out of the bedroom, my mouth wide open and moaning as Jayden fucked my hole. Oli was soon back in the room, a big smile on his face, my phone in his hand and his cock pointing straight out in front of him. 'I picked up your phone James, I hope you don't mind. That way, you can do what you like with the photos and videos.'

He stood in the doorway, 'Jayden start fucking him properly, let's get a good start to this show,' he laughed.

Jayden released my ankles and picked up the pace. He leaned closer to me and placed his hands on either side of my head. I instinctively wrapped my legs around his waist and welcomed the new pace he was fucking me with. I was moaning uncontrollably, and I could see Oli now walking around the bed, the phone pointing in our direction.