πŸ“š the-night-out Part 17 of 14
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The Night Out

The Night Out

by Plaza_plaz
19 min read
4.8 (12800 views)
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It had all started on a work night out. Dinner and drinks in a pub first and then the majority went home around 10pm back to their families and other halves. There were four of us remaining: myself, Lydia, Jess and Amy. Lydia, as she always did, was talking up the merits of going to the local gay club and with the other two in agreement I shrugged my shoulders and began walking down the street with them. I had nowhere else to be tonight having recently split up with my girlfriend of 8 years and I'd kind of hoped that I might get a chance to flirt with Jess a bit as I'd always fancied her.

When we got inside it took all of twenty minutes of generic chatting with Jess to realise she really wasn't interested in me that way which took the pressure off. I decided I was just going to drink, dance and enjoy my night so headed to the bar. It was while I was standing at the bar James first came over.

"Good night?" he asked as he sidled in next to me. I turned to look at him. James must have been in his late 30s. He was around 6 foot tall, with a trim beard and deep brown eyes, and he had a manner and smile that instantly put you at ease.

"Yeah not bad thanks," I replied quickly before turning back to the barman who was giving me the shots I had ordered for the girls.

"Don't think I've seen you in here before," James said. His tone was relaxed but definitely flirty.

"Work night out," I nodded across to where the three girls were sat.

"Ahhh, you straight then?" James' tone changed ever so slightly.

"Usually," I replied jokingly and then instantly wondered why I had. I mean, I was straight and had definitely been for the last 8 years. I'd experimented with a guy in my early twenties but that was it and I had originally come here to try my luck with Jess. So why didn't I just say yes? I didn't really know. Maybe it was because I'd been flattered by the attention of James and felt bad when he sounded disappointed. Anyway, it was said now and James had raised an eyebrow.

"When are you unusual then?" he teased.

"Honestly," I started, deciding that honesty was probably the best policy here, "not for ten years or so. And it wasn't great from what I can remember."

"I see."

I could see James looking me up and down and I wondered what he was thinking. Was he trying to decide if I was worth the hassle? To be honest I probably wasn't and he was a cute guy who I was sure would be going home with someone at the end of the night if that was what he was after. I decided a subject change was in order.

"Who are you out with?" I asked.

"Want to know if I'm here with my boyfriend?" he fired back and I went red.

"No...I... was just..." I stuttered and he laughed.

"Relax, I'm just taking the piss. I'm here with a group but we always end up peeling off from each other as the night goes on. I'm James by the way."

"Steve," I replied and momentarily nearly offered my hand to shake his but thought better of it. I was really starting to fulfill every stereotype of a straight guy at a gay bar.

"Well nice to meet you Steve. Maybe I'll see you later if you come through to dance."

He took his drink and left and I went back to the girls with our shots. For the next hour or so I sat chatting with the girls, drinking and getting up to dance for the odd tune. I wasn't much of a dancer but as they started busting out some 90s classics I found myself up more and more alongside Lydia who would dance at anything. The next part of the night was a blur of dancing, drinking and I swear I saw Lydia getting of with a girl near the smoking area. Now it made sense why she wanted to come here. I turned with the intention of telling Jess and Amy but then realised in my slow, drunk way that they had left twenty minutes ago. With Lydia otherwise engaged it looked like the night had come to a natural end.

"I should probably go," I said to myself and started walking through the club and out. I had thought about saying goodbye to Lydia but I didn't want to interrupt her. I could get all the gossip on Monday anyway. It was while I was thinking about this I bumped into James again near the stairs to the exit. He smiled that easy smile at me.

"You off then?"

"Yeah, night has kind of come to its natural end," I told him. "What about you."

"I was thinking about it. Think I'm as drunk as I want to be and I'm not really in the mood to stay up late dancing."

"Fair enough. I'm thinking the same thing. Hope getting a taxi out here won't be too hard."

"I've got an Uber ordered," James said flashing me a look at his phone. "Where do you stay?"

"Just down by Penny Street, near the old school."

"I stay just up from the Rush if you want to jump in my cab. You'll be practically there," he offered. I thought about his offer for a moment. He was right. I would just be a ten minute walk from my house.

"Sure, but I'll give you some cash if you..."

"Don't even think about it. I'm going whether you're in the car or not so it makes no difference to me."

"Thanks," I said and he nodded towards the exit. I followed him out into the cool night air.

I needn't had worried as it wasn't particularly busy outside. A few people were milling about deciding whether to try and go home or go on and the queue for taxis was about 8 deep across the road. I turned from the queue to look at James and noticed he was staring at me quite intently with those brown eyes. I could tell he was weighing something up again.

"Are you o..." I began to say and was stopped as he leaned and kissed me. I was taken aback but only momentarily. He was a good kisser and my God I was actually really horny. I'd played it down as I didn't think I was getting a shot with Jess but I had come out with the intention of getting laid tonight. I kissed him back and opened my mouth allowing our tongues to start intertwining. This felt right but I had so many questions in my head. I broke it off and looked at him.

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"Sorry," he said. "I just wasn't sure whether you were being deliberately flirty or whether you were being obliviously straight so I took a chance."

"I think I was being both," I told him and laughed nervously. There was a brief pause between us and this time I went back in for the kiss. Slower and more deliberate.

Our hands started searching each others bodies as we did and I could feel my cock starting to swell. I could also feel his through his jeans. We kissed for a moment longer and then stopped when James felt his phone vibrate.

"Taxi's a minute away," he told me. "And I have a no kissing policy in Ubers after a homophobic twat gave me a bad rating."

"That's too bad," I replied.

"So I guess the question is do you want to come back to mine or walk home by yourself?"

"Come back to yours?" I questioned, except this time I understood the signals loud and clear. I just wanted to hear him say what he was thinking.

"Yeah, come to mine so I can fuck you," he smiled.

"Taxi's here," I told him as I noticed it pulling round the corner and I shot him a grin. I was going back to his.

The taxi ride to James' wasn't a long one but it felt like an eternity. Now I'd kissed him my inhibitions had been released but the sexual tension was unbearable. We sat in the back just looking at each other. I was mentally undressing him, wondering whether he was hairy or smooth, what his cock was like. I also thought about those encounters of years ago. I'd sucked a dick but that was about it. What else where we going to do? What else could we do?

Eventually the taxi came to a stop and we got out. James gestured me into his close and up the stairs towards his flat and I followed. I was really doing this. I was about to go into this man's flat and have sex with him, something I hadn't even considered a possibility several hours ago. James turned the key in his front door and I followed him into the hallway closing the door behind me. As soon as I did James tossed his keys onto the small table next to him and took one step towards me.

We kissed again but this time it was urgent. Hands began to grope and fly everywhere. Within seconds he had lifted off my t-shirt and I had unbuttoned the shirt he was wearing. He had some hair on his chest, quite similar to me. Not hirsuite but not smooth.

"Mmm, you're hairy. I like that," he told me and dove straight towards my nipple, teasing it with his teeth and flicking it with his tongue. I let out a little moan and felt him grab my hardening cock through my jeans. "Bedroom. Now," he ordered. pointing to a room just off on the left. I walked ahead of him and as I did he slapped my ass. I hadn't really thought about roles or how this encounter was going to go down but I was rapidly getting the feeling that James was going to be in charge and the thought of that turned me on even more. I walked into his bedroom and sat down on the edge of the bed as he came towards me and slid his shirt off. I decided it was time for me to take some initiative and I stopped him short of the bed, his crotch in line with my face and began to unbuckle his jeans. I undid them and slid them down and could see his erection thickly outlined in the briefs he was wearing.

It'd been a while since I'd done anything like this but I decided to just go for it and began to kiss around the outline of his cock in his pants. I teased and toyed with him this way for a few minutes before finally deciding that I needed to see it. I continued to kiss it and as I did I hitched my hands into either side of his pants and pulled them down. His cock sprang out and now I could I fully see what I was working with. Seven or so inches with a decent thickness to it. It wasn't too big or too thick which I was thankful for given my inexperience. I took it in my hand and slowly pumped it: once, twice, a third time. James let out a guttural moan and I looked him in his deep brown eyes. His expression was one of firm insistence. I knew what I had to do. I opened my mouth and slowly started to suck his cock. I tried to concentrate on all the things I knew I liked when getting a blow-job and although there was no way I was going to get all of it in my mouth I knew I could use my tongue to good effect. It seemed to be working anyway as James was offering encouragement.

"Mmm yeah that's it. That's good," he told me as I bobbed up and down on his dick.

Feeling like I was getting into a rhythm I decided I to look up at him as I was sucking his cock and as I did I could see pure lust in his eyes. I kept eye contact with him and withdrew my mouth from his dick. He raised an eyebrow at me and I just smiled and then ran my tongue all the way from his balls across the bottom of his shaft slowly without breaking eye contact. He stared wantonly at me as I made my way to the tip. I balanced my tongue there and slowly swirled it around before taking him in my mouth once more.

"Mmmmmm," I moaned as I broke eye contact and tried to take as much of him as I could.

"Fuuucckkk," he breathed heavily as I did. "Are you sure the last time you did this you weren't very good?" I stopped sucking and smiled up to him.

"Maybe you bring out the best in me," I joked.

"Take your clothes off," he ordered as he slipped his jeans and pants off to be fully naked. I did as I was asked and was soon naked in front of him. I was about to go back to sucking him but James clearly had other ideas. "No, I want you to lay face down on the bed," he told me. The nerves came back. Did he want my ass? I'd never done anything like that in my life. I felt like I wanted it but I wasn't so sure.

I laid down as I was told, after all I had come this far, and waited with bated breath for what James was going to do. I felt him climbing onto the bed and his hands on my back. He ran them down my back towards my ass and rested them on my cheeks. I shivered as he pulled them apart.

"Mmm. Look at this hole. Have you ever been fucked Steve?" he asked me.

"No," I replied truthfully.

"Beautiful," he murmured and slapped my ass gently. "Don't worry, I'm going to do this just right. In fact when I'm done you're going to be wondering why you waited so long to have a man fuck you," he said confidently. I was about to reply when I felt his beard on the small of my back and his tongue then running down towards my ass crack. I didn't know what to expect but as he started to slowly eat my ass I felt sensations I had never felt before.

"Oh fuck," was all I could think to say as he licked and probed my virgin hole. He was fucking good at it and as he continued to rim me I was become acutely aware of the pleasurable sensations my ass was giving me. It was unlocking new parts of my brain I hadn't even thought existed and I was loving it. He continued to probe my hole with his tongue, making it wetter and going deeper. As he did I began to think about what his main intention was. It wasn't just to eat my ass, as much as we were both enjoying it, it was so he could fuck it. After a while he stopped rimming me and started running his hands over my ass cheeks and lower back.

"Let's see how much that's loosened you up," he told me. I looked over my shoulder and could see him eagerly licking his fingers and covering them with saliva. He winked at me as he lowered his wet finger to my ass and began to slowly probe my hole with it. My hole felt wet but it was still difficult for him to slide his finger in.

"Okay, we're going to need some lube for this," he said as he leaned over to his bedside table and opened a draw. I heard a bottle snap open and then felt cool liquid drizzling onto my ass crack. He closed the bottle, replaced it on the table and then started running his fingers up and down my crack again, lubing them up. This time when his finger came to my sphincter it slid in with much less resistance.

"Woah," I jolted slightly as this new sensation took hold.

"Relax," James reassured me. "I promise you this will feel good and if it doesn't you can tell me."

For the next few minutes James worked his one finger in and out of my hole and I slowly got used to the sensation of it inside me. He then started to work a second finger which felt okay. The third, when it came, was a bit sore at first but the lube was helping and as he slid those fingers in deeper I was beginning to lose myself in the sensations. I began to gyrate in time with his fingers and enjoyed the twin sensations of them inside me and my cock rubbing against the mattress.

"Mmmm, does that feel good. You like having those fingers inside you?"

"Yeah, it does feel good."

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"Do you know what's going to feel even better?" James asked, the intentions clear in his tone. Again, I knew what he was going to say but I wanted to hear him say it.

"What?"

"My cock. Sliding inside you. Fucking you."

I moaned as he jabbed his fingers deeper into me as he said 'fucking you'. I looked over my shoulder at him again but there was no grin on my face this time. Just desire. I wanted this man to fuck me and I could tell that he wanted it to. He removed his fingers from my hole and placed his hands either side of my hips.

"On your hands and knees," he told me. I propped myself up onto my hands and knees and watched him carefully as he got the lube again. I felt some more applied to my hole and then him rubbing some along his cock.

"Are you ready?" he asked me.

"As ready as I'll ever be."

"This might hurt at first. As you feel it going in push out and if it's too much just tell me. It's going to feel really different to the fingers."

"Okay. I'm ready," I told him and braced myself. I felt him shift up behind me and line his cock up with my hole. I could feel the tip sliding in my crack as it searched for the entrance.

"Here we go," he said as his cockhead found my sphincter and pushed against it.

There was resistance at first and I pushed back against it and then I felt him enter me for the first time and I felt a jab of pain as he began to slide into me.

"Ahhhh. I think it's too much," I told him as he slid all the way in and then I pulled away. "Sorry, that was a lot." James smiled at me reassuringly.

"It's fine. We'll go at your pace and take it slow." He leaned over me. "Here," he said. I turned to him and he kissed me. It was deep kiss full of desire and as we kissed there was no pain in my ass anymore and I could feel myself wanting him to try again.

"You should try again," I said as I broke off the kiss. He said nothing, went back behind me and lined up to try again. This time there was less resistance and as the cock slid back into my hole there was much less pain. I pushed back towards him and heard him moan as he bottomed out in me.

"I'm just going to wait a bit, let you get used to me," he told me. It was in that moment I became hyper aware that I was fully naked, on all fours on a man's bed with his cock buried deep inside me and in this moment of self-awareness I realised that my life would never be the same again. There was a cock deep inside my ass and I felt good. "How does that feel?" James asked.

"Good," I replied truthfully. "I didn't think it would."

"Well it's about to get even better," he said and slowly began to move. He took it slow at first allowing me time to process all the new sensations of what it was like to be fucked in the ass and then as we slowly began to build a rhythm I started to rock back and forth with him.

"Ooohhh God," I whispered as he fucked me.

"Yeah, you like that? You like how my hard cock feels in you?" he demanded.

"It feels good, so good," I told him as we began to quicken our pace.

"Mmm yeah. I knew your ass was going to feel good the moment I saw you," he said as he moved his hands to my shoulders and started to pound deeper.

"I didn't know. I didn't know how good," I said breathlessly.

"Yeah but you do now don't you. You know how good cock feels and you'll never be the same again," James moaned as he pumped me harder and I knew he was right. How could I be the same after this? Before tonight I never even knew these sensations existed and now, now I was fully indoctrinated.

"Fuck me James, fuck me," I begged. I was begging a man to fuck me.

"Mmmm yeah, fuck," he growled. He was properly fucking me now. The slow and steady start had given way to relentless pounding as his cock slid in and out of my previously virgin hole. His hands moved from his shoulders to my hair and he pulled me up towards him. He wrapped one hand gently around my neck to give himself leverage and the other slid to my cock and began to stroke it. All the while he continued to fuck me. I could feel his hot breath on the back of my neck and I turned my head towards him. The angle wasn't the best but I wanted to kiss him. I needed to kiss him. Our lips mashed together and our tongues probed as he fucked me harder still. Pure lust had now overtaken both of us. He continued to massage my cock with his free hand and I was becoming acutely aware that my orgasm was building. He broke the kiss off and and then moved his lips to my ear.

"I'm getting close. I'm going to cum soon," he whispered directly into my ear.

"Me too," I raggedly replied. I suddenly became aware that he wasn't wearing a condom but instantly dismissed it. I was too far into this now to let that worry me.

"Where do you want me to shoot," he asked me, obviously aware that he was barebacking a stranger.

"I want you to cum inside me," I told him. There was no way I wasn't getting the full experience.

"Are you sure," he asked again but I knew this was more out of politeness than worry. He wanted to cum in my ass as much as I wanted him to.

"Don't you fucking dare pull out," I warned him and he smiled that smile of his again.

"I wasn't going to," he said firmly as I heard his breathing becoming sharper. "I'm nearly there," he said and I could feel my own orgasm building as he worked my cock with his hand.

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