FabGuys.com forum: My first sleazy holiday

By *orthing500 OP Man
7 days ago

Callington

This is a true story of my awakening to the more sleazy side of gay sex and clubs. Back in the 90's I was mid 20's, fit and single. I was straight and had girlfriends until I was about 24. For a year or so I was meeting men and women.

Using gaydar I met an older couple of guys and we had some great threesomes with them. They were both about 60 and fit, I loved the daddy son play that we always did. They asked me if I would like to come on holiday with them as they have a two bedroom holiday flat in Gran Canaria, all I had to pay was for my flights.

On the flight over they asked if I fancied a bit of a twist. The flat was two bedrooms and I was assuming I would get one room and they would be in the other. They suggested that each one of them would have a bedroom each and I could switch between each bedroom, first night in one and the next night with the other guy. Yes I am game for that I told them.

Back then I was 50:50 vers and always did safe sex with everyone and we had great threesomes with them taking the lead and me being submissive and doing what they wanted. This was a massive turn on for me.

The plan was that they would show me all the scene and we would all have some great sex. I loved the idea that when we went to a bar that they would tell me what to wear and if they wanted me to take off my shirt or shirt and shorts when we were in the bar I would. I was working on building sites and had a great body and making me wear just my underwear in the sleazy bars would be good to show me off to anyone in the bar. I would even go shopping with them and get sexy underwear, the harness I have in some of my profile photos was the harness that they got for me on that holiday, it's now 30+ years old and I still wear it.

We arrived at their flat which was in easy walking distance from the yumbo centre. I was to be with John that night who was vers but more of a top, he had the room that had a small bathroom attached which would be handy so I could douch when he was needing me to be fucked. We chatted about what to wear in bed and both guys preferred me in underwear or naked. I had only played with them as a couple and I didn't expect it to be even better when I was one to one with one of them. The sex was so different and more sensual. Loads more kissing and cuddling. It was fantastic to sleep with another man. All of my gay life I had been single and this was a completely different experience. My nights with John were not all fucking but was mostly more sensual, when he did fuck me it was so natural and uninhibited. We would be spooning and I could feel his cock rubbing against my hole, his cock would occasionally slip in a bit then we would stop to grab a condom before I got a good fucking.

A couple of nights later I was with John again and again it was so sensual he dipped his cock into my ass, as he pulled out he asked me if he could bareback me? I knew they were both regular tested and agreed. It was one of the best fucks I had. As he was building up he asked if he could come in my ass, fuck yes I said. The next morning he asked me not to tell Ian about us barebacking as he would not approve.

Nights with Ian were just as sensational he was much more hairy than John and had the typical bear look. The nights were much the same and I loved sleeping with my daddy bear. I can remember me lying on my back with him on top of me with my cock rubbing along his hairy ass. I am still massively turned on with hairy guys. We were passionately kissing and I asked if I can slip my cock in raw? Fuck I would love that but don't tell John, he was riding my cock like nothing I have done before. He didn't stop until I burst my spunk into his ass.

The rest of the two weeks were the best sex I have ever had. They showed me the dark rooms of Gran Canaria and I had some great sex all safe with many guys. Neither of them mentioned the Bearback sex and we never talked about it but from that first couple of nights all the sex I had with each of them was fucking raw. They taught me so much and it was a holiday I have never forgotten. For years later it was always safe sex and it's only the last five years when because of PrEP that I have fucked and been fucked raw but I will never forget that holiday. I would love to hear any holiday stories from other guys.