jrmdavis saidOh I was hoping there was a similar position or some variation of cowboy that could work. Like if he sits up while Im on top or something. I'm inexperienced as a bottom and he's a fuck buddy, not a boyfriend, so I'm shy to awkwardly fumble through 20 different positions trying to ride him without hurting him.
Let the top guide you with positions that work for him. It might be with him sitting in an armless kitchen chair, or straddling a bench, you seated on his lap, facing him or away. Or missionary style with you on top. Only instead of you penetrating him, he's inside you. And you're moving back & forth along his chest, rather than up & down. Oil your bodies and have some sliding fun!
Experimenting with different positions can be great. And remember, HE'S part of the equation, too. You may have a favorite position that makes you orgasm best. But save that one for your finale, and first go through others that HE likes.
As the bottom, though, it's understood you'll probably want to cum first, if you can while bottoming, because once your top pops the show is likely over, at least for a while.
I'll mention something about hardon bending: don't ever do it - dicks break! Some men can burst the erectile bodies inside the penis that produce an erection (the 2 corpora cavernosa are most susceptible to damage). Guys who have an extreme curve to their erect penis likely have experienced a problem with one of these bodies. Healing is problematical and can take a long time, if ever.
So while an erection can be hard as steel (we hope) it's still fragile, and shouldn't be manhandled (slight pun). You can stroke it, suck it, and sit on it, but don't strain it or strike it.