It started out like any other business trip I'd been on, I never expected it to end the way it did...

After securing a pretty good deal me and my boss headed straight to the hotel bar to grab a nice cold beer to celebrate after a long day of meetings and being stuck in hot meeting rooms. We were having a good time and had a few beers and a meal, we planned on grabbing a some bottles from the shop next door to take up to our rooms to continue the celebration before grabbing the train home the next day. I'd been working at this company for many years and had been on many trips with my boss and other colleagues, all ending up in similar ways of having a good meal and drinks and heading back to the rooms. This time felt different.

My boss had been pretty open about his recent breakup and we had ended up talking about the lack of sex in our lives. We were both single so decided we could go out in the local town bars and clubs to try and find some women to take back to our rooms to fuck, however we were both unsuccessful after every bar we went into was basically full of men. We decided to head back to our hotel, and finish the crate of beer we'd opened, the room was so hot when we got back into his room, so naturally we opened our shirts slightly and unfastened our ties etc. 

Things were still pretty normal and our conversation ended leading back towards sex. We talked about the things we liked and ended up finding we were both liked threesomes, especially mmf. The conversations continued and we talked about the best sex we'd both had, the weirdest places we'd fucked. The conversations were started to get me quite aroused and started to wonder if my boss was feeling the same, little did i know, he definitely was.

I glanced down at my trousers to make sure my boner that I'd now developed wasn't too visible, I subtly tried to rearrange my trousers and position slightly to hide my hard cock that had continued to grow. I was just giving my trousers a final touch up when my boss looked across and slyly glanced down towards my crotch, I stopped and moved my hands back to my sides and picked up my beer to take a quick drink, now nervous he'd caught me I downed the rest of my bottle and walked across to the dresser to pick up another bottle, I asked my boss if he wanted another which he agreed to and as I turned around to walk back across the room to give him another beer he had now unbuttoned more of his shirt and he was now rearranging his position, clearly trying to hide his boner too. I tried not to look for too long until he broke the ice and said "I caught you trying to hide yours before and hadn't realised how hard i got!" I nervously laughed and quickly responded saying it was okay and quickly sat back down and tried to let the conversation quickly get flowing again so I would be able to forget how awkward this could get, but my boss didn't seem to want to move on...

'Wheres the strangest place you've wanked?" he said. I was taken aback by the question slightly and swallowing some beer with a nervous gulp. 

"wow, i ermm" i know we were talking about sex and women but never expected to come into this topic with my boss, yes we'd joked and talked about sex before, but talking about wanking seemed different. "just the gym toilets or showers" i replied "nothing too crazy for me haha" 

"mine could possibly be out in the woods or maybe in my office at work" he continued with "i quite like the thrill of it, what would happen if someone caught me you know" i'd always thought the same but had always been too nervous to actually go out and wank in public, he seemed to be more brave than me, but i was growing more curious and wanted to know more "and have you ever been caught?" i asked...

he quickly responded with a no, but held his breath, almost as if he wasn't finished answering my question.

"however i have always wondered what it would be like" 

I couldn't believe what was happening, one of my biggest fantasies had always been getting caught wanking, but an even. bigger fantasy... "wanking with someone else has always made me curious too" he continued. I was in disbelief at what was happening... and the fact my boss had scarily the same fantasies as I had. I must of been so deep in thought when I looked back across and my boss was rearranging himself again. I thought I would maybe never get an opportunity like this again, so I plucked up the courage and told him

"you know I've always thought the same"

the awkward tension seemed to drop, and I could feel my shoulders relaxing, looking across at my boss it looked like he had the same reaction, he let out a sigh and asked me.

"have you ever wanked with another guy?"

could this finally be happening, I think he could almost tell what my answer would be, I could tell he was still nervous, just by the tone of his voice. Me and my boss weren't that close, we'd always invited each other out for our birthdays occasionally and often went out to play golf and things, but this was the first time we had talked about something like this. Almost as if we were both so embarrassed about it all. 

'no" i replied, i could feel my boss waiting for me to continue this sentence, he was almost leaned forward, so he could hear better, his bottle of beer, tightly clutched in his hands. It seemed we'd both forgotten we had a drink, I took a quick sip. It was warm, my hands must have been sweating so much they'd warmed it up. After the sip of courage I needed i finally continued my sentence. "I have always wanted to try it though"

Since I was around 16 it's been a fantasy of mine to wank with another guy. It had never happened with any of my mates and I'd always been too nervous to go out cruising or meeting guys I'd talked to on my alternate twitter page, I'd grown up in quite a small town and was always scared someone I know would catch me and tell everyone. I'd hoped since moving closer into the city it would have eventually happened, but I'd had no luck.

I started telling my boss all of this and it turns out he had similar experience and concern. 

Fuck it! I thought and was about to open my mouth to ask him....

"why don't we just try it then" he said

my mouth went dry and his words shocked me, my boss was the last person I expected this to happen with.  He never seemed like the sort of person who would want to try this out with me, but as the night had gone on I never realised how much we had in common. 

'why not" i replied "theres bound to be some porn we can find"

"yeah" he responded "lets just put some porn on, have another beer and let it happen naturally"

within minutes we'd found a porn channel on the hotel room TV, I had some lube in my room I remembered, I always packed some on work trips to hotels. I knew I'd always end up back in my room wanking. I said I'd quickly pop to my room opposite to get it and then come back in.

I got up from the chair and headed out, still in shock at what was about to happen, I'd thought about a moment like this for years and now it was finally happening.  I poked my head out his door and looked to see if there was anyone around,  luckily the corridor was empty because there was no hiding how hard my cock now was, I went into my room grabbed my bottle of lube from my bag and headed back onto his room to find him like this....