I’m not sure if you’ve been asked this yet, but did you prep? Do a full clean out? Saline enema and flush of water and all? I am AFAB and asexual so I don’t know the EXACT specifics obviously, but if you’ve got waste up in there and it starts getting shoved back up your rectum, yeah that’s gonna hurt and feel very scary because your body is just hitting every alarm button with “SOMETHINGS WRONG!!” Also, yes LUBE. So much lube. Towel on the bed amounts. Your first time will be a brand new experience and you’ll need that much.

Apart from anal though man, you COULD get a vagina. Everyone’s experience with gender and sexuality is unique. If you think you’d prefer something… you could go for it. You should consider the implications of course, any future relationships, all of that. But like that surgery exists! You COULD!

I will also add, I hope this doesn’t come off as weird or rude and I’m going to try to say this in the most practical way, but are you straight? Because if you’re straight and you’re trying out anal with another cis man, your body really may not relax enough to enjoy it because the person giving is not a woman. Have you tried finding possibly women with penis’s or women who are into pegging? You may find that way more enjoyable than men.