It was an easy question but how to ask it. Me and Jake had been friends for more than ten years before the question was asked. We had met through a mutual friend while I was working in a local nightclub. We just seemed to hit it off straight away and so we would spend most of my nights off in the same nightclub. We chatted about almost everything and often had long discussions on the most trivial topics. These discussions would last for hours and a lot of beers. We became members of the local casino and would go there after I finished work. Eventually I got a daytime job and we were able to go out more often and could go almost anywhere as all the local nightclubs had an arrangement where staff from one could go into any of the others for free. We would sit in the VIP lounge and drink quietly with the managers or other important people. This went on for years and we must have covered every possible topic during those long nights spent in noisy bars and club.
After a while I bought a house and started to settle down in my job, although neither of us had a steady girlfriend we did know lots of girls especially Jake. He worked in an office and seemed to know most of the women we would run into on our weekly nights out. The question of if we would get married was never an issue as we were both enjoying being bachelors too much. A few times we would forego the night out for a boozy night in at my place. Here we would watch a movie or two or just chat while we drank a large amount of beer. I had a few porno videos and occasionally we would watch one for a while but it didn't really interrupt the conversation or the beer.
One day a friend of ours asked me if I thought Jake was gay as she had never seen him with a girlfriend. I had had a few short-lived romances during the time I knew him but when I thought about it a little I realised that he hadn't had any. It got me thinking and I decided to find out one way or the other.
The next time we spent the night boozing at my house I asked him what he thought about gay men and if he had been to any of the local gay bars. His reaction was if anything a little too emphatic "No Never!" leading me to wonder if "he doth protest too much". I now wanted to really find out how far he would go.
I had a few porno videos in which a man would fuck the arse of some woman and she would scream and shout as if she was really getting off on it. I had one that started with the woman slowly sucking the guy hard and then he would turn her round and very slowly push his cock into her waiting anus. It finished with him pulling out and spraying her backside with cum. This would be perfect as much of the time the camera concentrated solely on his cock. It was easy enough to forget the gender of the asshole being pounded. This was what I would start the entertainment with next time.
The next time was a few weeks later and we started with a movie and a couple of beers. After an hour or so we decided the movie was a little boring so I suggested we watch a porno instead and Jake agreed. I started the video and tried to see his reaction without him noticing. He seemed to be interested but didn't really make any comments so I did.
"She seems to be enjoying sucking his cock" I said as dispassionately as I could. "He seems to be enjoying get it sucked as well". We watched as the head of his cock slowly slid inside her waiting ass. "God, that's a big cock to fit inside such a tight hole." I said as it disappeared all the way to his balls.
"Yeah" was all Jake said as he stared at the TV screen.
"He is really banging away on that ass." I said deliberately not saying anything thing about who's ass it was. "And they're really pushing back on to it." Another "yeah" was all the reply I got again as the guy built up towards the cumshot. "Fuck, look at all that thick cum". Jake was now on the edge of his seat watching as the guy's cock spurted the white fluid all over her back. From Jake's reaction I knew he was interested but I still wasn't sure if it was because the fucking the woman's ass was getting or the sight of the guy's cock so I decided to go even further next time.
I went to the local sex shop and bought a gay video with the intention of setting it up for the next night in. This time Jake asked if we could stay in the following week as he "didn't have much money this week". I wasn't sure but I hoped it was because he wanted to watch a video instead. I normally got a shower long before Jake arrived but this time I waited until only twenty minutes before he was due to arrive. I washed all over and made sure my hair was still wet when he arrived. I let him in dressed only in a towel and said I got home late and hadn't had time to get dressed yet. He seemed to be happy enough to sit and wait but I said I wouldn't bother as we weren't going out. It was warm enough to sit in just the towel so I suggested we get a beer and start the video instead of getting dressed again.
"No problem, it's your house." Was the reply as he sat down in front of the TV.
"I'll get the beers you find a video to watch. I got a few new ones, they are over there near the TV." There were a couple of crappy movies on top and then a porno and then the gay video. I took my time getting the beers and glasses so that he could look through all of them and choose the one I hoped he would choose. When I got back he was reading the cover of one of the boxes but I couldn't see which. "Put one in and start the player" I said as I put his beer down. It was at this point I should have thought about what would happen if he put the gay one in or least what I would do.
