When I was a kid in grade school I bottomed the first time for a boy who was a highschooler. It wasn't painful at all, in fact I liked it. Corduroys off, legs spread wide with underpants yanked down in the back I submitted.
I was nine and he was fifteen. He fucked me at least weekly till I moved in my twelfth year.
My boyishly pert little boy's cheeks welcomed the contact of boy on boy flesh, but I had yet to orgasm. We'd moved a short distance away and after a month still totally smooth I was awakened by a strange sensation. I'd already been having dry orgasms, but there it was my young boys white cotton underpants were fully drenched in the front from my little stiffies first orgasm. It unloaded with an intensity that woke up for the finish. I was dreaming of Him fucking me.
I spent the Christmas week at Grandma's, his neighborhood. We hooked up immediately when his parents conveniently were at work. I was shy about nudity and thought I was risque when I stripped down to my underpants in front of him and slid under the covers.
He went to the bathroom down the hall opposite his bedroom. With the bathroom door open the mirror on it was perfect, I could see his gorgeously cute eighteen year old body as he washed his cock. I slipped out of my underpants as he walked back to his room. Sitting up, keeping myself covered I leaned forward and took him in my mouth, something I hadn't done before, though he'd asked numerous times.
He came immediately and I swallowed the best I could. I blushed with embarrassment as soon as I looked at him. He slid under the covers and kissed me on my lips. Also a first, he'd been fucking me but we never made love till now.
When he discovered my nudity his more experienced tongue fluttering like a butterfly all over my smooth flesh. Within moments he entered me and I exploded with my first cock in the ass orgasm. We made love twice a day the entire week, even outside in the snow, lol. Then it was he that moved, too far away to meet.
I went through my teenage years with an occasional boy/boy, man/boy relationship. Getting fucked kind of hurt now for some reason.
When I was engaged to get married I decided I needed to experience man/man love making. Though it was excited and satisfying I've yet to feel a cock that doesn't feel like it's gonna split me open.
Size aside even a relatively small cock feels too big. I keep trying!