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I’m sorry to hear it dude. But yes, training may be an issue: both for your top(s) and for your ass.I don't think it's the tops fault tbh... I mean, it's not like he can see inside. I don't know... It always hurts with all tops, I don't think all of them are that dumb sexually hehe...
But yes, I guess it's training?
For me personally, my hole tends to cramp up when a guy first goes in, though it relaxes after a few seconds. I found that if I used a dildo or vibrator beforehand, I could condition my ass to avoid the worst of the cramping. Or at least I can get it out of the way when I’m by myself, so it doesn’t hurt when we’re in the moment.
It sounds like you might’ve already tried some technique, but wanted to share what works for me, for whatever that’s worth!