Could have put this in the "When I was a kid" section too.......As a sixteen year old kid, I witnessed our neighbor sticking a dildo up his ass one afternoon, when I went to get a ball I kicked over their fence. He was lay on towel in their kitchen and fucking himself, when he saw me staring at him. I didn't know it immediately as I was too busy watching him, but I'd gotten a hard on.
The rear patio doors were open, so he simply asked and signaled with his index finger for me to enter. I did as he asked and stood only a couple of feet away. He looked up at me and said "You lost your cherry yet boy". When I shook my head, he said "You wanna stick that boner up my hole here". It was only then I realized I had an erection.
I'd heard other guys my age, telling of their supposed conquests fucking girls. And one guy admitting he'd been fucked, but I didn't know anyone who'd fucked a guys asshole.
So with not too much forethought, I dropped my shorts, let my cock out of the loose fitting underwear I had on, and sort of held my cock to his asshole after kneeling down. He took hold of my cock shaft, tugged on it a few times telling me I was real big and then told me to push it into his ass. I did as I was told and before I knew it, I was deep inside our neighbors asshole. It just came naturally from that point onwards with me fucking him, using his asshole as I'd used my right hand many times before.
He raised his legs high and wide and began to moan loudly, especially when I pounded into him harder and harder. Taking hold of his smaller fat cock he started to wank himself off, which in turn made me want to fuck him faster as my own orgasm built up. Telling him I wanted to cum after fucking him for no more than five minutes, he sort of yelled out for me to cum up his ass. No sooner than I begun to cum, than his cock let go and his cum flew everywhere.
I'd just about emptied my balls as I now remember, when the front door to his home opened and his wife shouted out for him to help her with the shopping. We quickly got ourselves together and I hoped over the fence forgetting to pick up my ball. Later that evening he called by with it. My mom answered the door to him and shouted to me that or neighbor had my ball. Walking to the door, he had a huge grin on his face when I got there. And looking at my mom, then me, he said "If you want some more tips about football, let me know, I'm free all afternoon tomorrow". He smiled, said goodbye to me and my mom and walked away.
The following afternoon, I was showered, horny and ready to learn. His wife had gone out to play a golf tournament with her club and wouldn't be back until late. It gave us plenty of time to explore everything sexual I'd been thinking about all night and that morning. I had my first very blow job and performed my first fellatio on a guy. A guy who was in his mid thirties and one for the next five years I sucked and fucked with, whenever we got any time to have sex.
Even the arrival of his first child, didn't stop him wanting every inch of my eight inch cock fucking him. Indeed six days after his daughter was born, I was fucking him from behind in his garage as his wife feeding the baby in their house.
To this very day I still pay him a sexual visit when I go to see my parents. This weekend will be the twentieth anniversary of our first fuck, and we've already agreed to meet up outdoors to celebrate. I'm going to fuck the shit out of him along with a surprise I've arranged. He's a nineteen year old who's cock I've had the joy of sucking. It's a little over ten inches long and so thick. It's my present to him for all the good times we've had together. I just hope he's ready to be fucked senseless.