I dont think you can hurt yourself ejaculating more than 1-2 times in a few mins.
I do think you can hurt your penis by bending it when hard. However you would likely not hurt yourself if you only bent it for a short time when it wasn’t fully hard.
You will likely get a plack/red/dark spot on your penis if you hurt yourself.
Of course if it hurt a lot and you dont get soft, or you have a swollen part ahead of the bend, you probably need to run to the doctor immediately.
I dont believe you have hurt yourself.
And man dont beat yourself up over ejaculating too soon. Most men blow before their woman is satisfied.
Men who have been having good sex for decades, still blow before their women do.
There is a fine line where you can excite youe woman and get her ready to orgasm with your hands, and fuck her just hard enough to make her orgasm her brains out, and just as she’s done and trust me it will be a long long time, several minutes you blow.
To make it worse, most women wont tell you in what spot they are, because usually it breaks their “flow”.
I can recognize it by the look on her face, but I’ve been finely tuned to my wife for decades. And even so, of late the patterns of both our sexualities has changed and I cant either find it, or fuck her long enough to make it happen. I now have to get her done by hand, and then just fuck her for myself. Still experimenting, for women orgasms with a penis are better. Finger orgasms hurt due to the fingerprints as well as lack a little of the satisfaction. Sorta like getting a hand job, instead of a blow job, or proper sex. As much as I love hand jobs, they hurt, blow jobs are great, but I dont cum, I’ve even fucked her face while fingering her pussy, and still dont cum.
Keep at it and you will get better.
Keep working your penis, and you will get bigger, stronger and most importantly last longer and get good erections on demand.
Lots of people are hung up on size (no pun intended) but getting a good hardon and being able to stay hard as long as you want, till you see the “oooooooo baby I’ve cum and cum and cum and you’re still fucking me, please blow and curl up with me” look on her face, and blowing it good and powerfully is better - trust me. Most women dont want a 10X6 hammer. Yea sure than works for some women, but if I had a 10X6, my wife would first never let me use more than 1/2 of it in her pussy, I’d never get anywhere near her ass with it, and to top it off, if I dont have it hard till she’s done, I’d get the “ewwww you have this big ugly thing and its dead before I’m even warm, get away from me”.
Practice both what you see here and with her. And enjoy the learning curves (as well as all other curves).
With, 25 years of fucking, and not bored with it yet, and yes I have got better, just that now, I have gone backwards and am working my way back.