Just a quick recap on my straight mate from work "Jack". We used to work together and I, along with every other gay and women in the office, fancied the pants off him. Alas he was straight and also had a gf who worked in the same office. Jack was always curious about life in general and eventually his curiosity turned to sexuality. Not long after he started to become curious his gf dumped him, he he saw this as his chance to explore. As one of his few gay friends I was the lucky one he wanted to explore with. I have previously written about a couple of our encounters here part 1 & part 2.

We hooked up several times over the space of about 6 months and sent each other LOTS of pics and images. He was fascinated by closes up of my cock and ass and we would sext a lot. In fact he wanted to do it even more than I did.

Sadly for me though Jack decided to move back home. He arranged some leaving drinks a few weeks before he left and invited me along with several other former work colleagues. Of course he had told no one of what we got up to so as far as everyone else knew we were just mates who hadn't really seen much of each other in the last year or so. It was fun just us all hanging out together like the old days but super hot knowing Jack and me were having a secret affair. It was even hotter when he was chatting to the guys about all the women he had been seeing since he's now single, none of them knowing that actually the guy sitting opposite him was filling his ass and giving him head.

Thankfully that was not the last time I would see Jack. We arranged our own private good bye for a week later.

Over the past 6 months or so of Jack exploring he had really gotten a taste for anal play and loved his ass being filled. In his last few weeks in London he was living with a friend and was too embarrassed to take his dildo with him in case it was spotted. As such he was pretty eager to get his hole filled before he left the country and I was pretty eager to oblige.

One thing that had disappointed me about our previous hook ups was that Jack never wanted to cum. He said he was scared cause he always loses interest as soon as he cums and was worried it would be too awkward. As a result I would edge his a lot but never allowed to finish him off. It was super frustrating I have to admit as I really have a thing for satisfying guys so it was a but unfulfilling in a way (still hot as fuck though). This time however he was well up for cumming (yes!). I think the fact this would be the last time we would ever meet meant that he didn't really worry if it was awkward or not, he would soon be on the other side of the planet so what did it matter.

So the day comes and I'm in the midst of moving house so my room is pretty empty with just a bed frame minus a mattress left. Not the comfiest environment to fuck in but that was not going to stop either of us.

As usual he wanted to go to the bathroom first while I stripped off in my room. As there was no mattress I was standing, cock out waiting for him when he walked in to my room naked. He walked over to me and I started to run my hands over his toned chest towards his semi hard cock and peachy bum. I started to stroke his cock as he started playing with mine before I got on my knees and started to blow him. He was moaning almost instantly and it wasn't long before he was rock hard in my mouth.

He soon pulled out his wet rock hard cock and turned around presenting his hot pink hole. I wasted no time in sticking my tongue in his ass and working it around his hole while i played with his low hanging balls and swinging cock.

After a lot of moaning he turned around and got on his knees and started to suck me. I may have mentioned this previously but fuck he gives good head. For someone who has only sucked cock a handful of times before (all being with me) he was fucking good, better than a lot of gay guys who have blown many, many more cocks. He got me nice and hard before be pulled away to grab his back. He pulled out a bottle of lube and a condom and handed them to me while he got on all 4's on the floor. I positioned my self behind him and rimmed him some more while I suited up and covered my dick in lube. I then lubed up his hole and started to push a finger in. As I started to massage his prostate I played with his cock before he was lose enough to push another finger inside him. Now he was nice and primed I pushed inside him. He takes cock like an absolute champ and was moaning loudly now. He really liked it as I picked up speed and began fucking him hard so my balls were smacking against his arse.

After a while on all 4's we switched positions. I lay down and he got on top and rode my dick. When he have done this before he has always faced away from me but this time he faced me as be bounced on my cock. This allowed me to jerk him off as I fucked him and to see the look on his face was priceless. It wasn't long till the magic moment, he wanted to cum and was going to let me. I picked up the past and fucked him as hard as I could till he blew his hot load all over my chest and stomach. The first time he had ever been made to cum by another guy. It felt so good to be covered in his cum.

Post clean up I had expected him to be a little awkward but there was none at all. We got dressed and talked about what he will do when he gets back home and his plans for the future. Seems I could have been making him cum all this time without any awkwardness at all! Oh well.

That unfortunately will probably be the last time I get to see Jack in the flesh, we have however continued to sext so I'll still get to see that gorgeous body and cock but I'll never get to taste it again. There were many times when we could have hooked up and didn't which he now says he regrets. Had he got over his nervousness at dabbling in man on man action sooner we probably could have had many, many more hot times like this but sadly it wasn't meant to be. I hope one day he will come back, even just for a holiday, but till then I have these encounters to remember.