My youngest guys were a couple of my friends when I was 15 years old, one of them was a couple of months older than me and the other one was a week older than me. We were at a holiday home of one of their parents all alone for a weekend, the two of them were there about six months before and that's when they had sex with each other for the 1st time.
We drank a bit of beer (and since I didn't draik at all before that I felt pretty drunk after a couple of beers) and started watching porn (which one of my friends took from his parents bedroom and if I remember it was Private teacher), as time went on I was getting hotter and hotter, one of them left the room saying he'll be back in a couple of mins and the other started to pull down his pants, he left his boxer shorts on and he started to jerk off slowly. He looked at me and asked me what I'm waiting for, so I dropped my pants as well and I started to jerk off as well.
Soon after that he said that he's tired and that he's leaving for the bedroom, I stayed on the couch in the living room jerking off to the movie. After about 30mins passed I started to wonder where's my other frined. I went looking for him in his room and as I got closer to his bedroom door I heard someone moaning and grunting, I slowly opened the door and saw one of my friends lying on top of the other while the other was fingering him and sucking him off.
I watched them for a little bit and I got really horny, I found some courage and entered the room and asked them what the hell they were doing. One of them told me to either join them or close the door and leave. He didn't need to ask me twice, since I dreamt of playing with the two of them every time I saw them strut their stuff butt naked in the locker room after practie or games. I joined them and went on to fuck for hours. It was pretty sloppy sex, but it was my 1st time with a men/boy and I loved every second of it.
Later on we went on those weekends every time we got a chance.
The oldest guy I had sex with was a trainer (and my neighbour) at my local gym. He was around 50 years old and he's an insane power bottom (but he didn't mind topping either), I was 22 at the time. I just joined a gym he was working in and I asked him if he would want to discuss what would be a good workout regime for me, he told me that he hasn't got the time at the moment, but that he's free later in the day and that I could come to his house if I want to.
Later on I went to his house and we started talking about what I should do, he started showing me some excercisses. We started doing some workouts and he was telling me what to do, I did some squats with weights and he started talking about how firm my ass is going to be after some time, if I stick with what he's telling me to do.
I was madly in attracted to him from the first time I saw him. He was absolutely perfect, hairy chest, ass and legs, unshaven face, muscular, unshaven pubes and a beautiful slightly curved ,short but rather thick (thickness is what matter boys and girls) uncut dick, I was in awe every time I saw him in the showers.
I intentianally wore a really tight workout shorts (without shirt) and I really tried to tease him because I suspected he has the hots for me. After the workout he told me to stretch out and I stood right in front of him, while he was sitting in a chair, I turned around from him and bent over doing my stretching out, he stood up from his chair and he grabbed me by my tighs and started talking about how firm they are.
He told me to keep stretching and that he'll try to massage my tighs and calfs while I'm stretching. He went to grab some oil and told me he'll be right back, when he returned I could clearly see that his dick was rock hard. I told him my arm feels a bit sore, he told me he'll check it out and started walking towards me, when he came close I just grabbed him and kissed him. We ended up making out and we pounded eachother pretty hard.
It's safe to say that squating down on his dick became my favourite workout routine.
