Wolverine has lost a hand before in Age of Apocalypse and it did not grow back. However he has regrown eyes before along with regenerating after firebombing charred him to a cinder so we can likely assume his cock and balls would also grow back.
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Additional discussion question: It can be inferred that Wolverine regenerates blood, and it is known that beer has minimal effect on him due to his enhaced bodily functions related to his regeneration. With this in mind, does Wolverine have a refractory period or can he fuck all night?
He'd probably have trouble to stay in the right mood for hours on end.
She'll grow whatever her little wolverine heart desires!
Maybe it depends on their hormone levels 🤔
Right amount of HRT: Vagina. No HRT: Penis.
The healing factor would attack the foreign hormones. Wolverine can't get drunk either because his body heals too quickly.
Those are different things, though. Hormones would be closer to vitamins, the body uses them if they're present without necessarily causing harm to the body. The body produced hormones, but, chemically, if the hormones are made or introduced, chemically, they're the same. Ethanol is a poison that works by affecting the brain by attaching to GABA receptors, so it is a threat to the body.
That's all science though. Wolverine's healing ability is basically magic. I mean, it regrows his hair to a certain length in a certain style too.
The backstory for his character is that his healing factor not only "heals" him, but basically restores him to the way he previously was whenever there's a change to his body.
I mean, yeah, that's magic I guess. So if Wolverine got Scarlet Witch to give him HRT, he'd have titties in a jiffy.
it regrows his hair to a certain length in a certain style too.
lol I totally didn't think about that, hmm...
Hormones are also processes by the liver for what its worth, specifically estradiol
it's a fictional godlike character, what happens is what best suits the story
All people contain both estrogen and testosterone. They just have them in different quantities. How would his body know that they're not natural?
Referring to Iron Man: Extremis #3 it's safe to assume that without hijacking said repair center Wolverine would regrow a penis almost instantly

But is that blueprint dependent on hormone levels? Maybe wolverine would just rapidly grow a full female reproductive system and boobs on HRT, which then would mean that to revert, masculinizing HRT would be needed.
So in theory you could somehow edit the repair center to grow a vagina instead, then the dick would fall right off
Matter-of-factly, Ultron hacks into Extremis in a later run and turns Tony Stark into a Janet Van Dyne lookalike.

At the end of the ordeal Tony Stark checks to see if he still has a penis.
snake definitely
The dick thing (there's a reason "he" is angry), also lots of super heros are thwarted trans people. It's why they're always meeting their "girl" versions, life is trying to tell them something.
"This bright lycra outfit makes me feel like I'm flying! But I also have rage issues."
"Oh wow, a girl version of me, I'll have to try extra hard not to have any realizations about who I am".
I have a can of peanut brittle to share with you
depends if he still has adamantium skeleton, since adamantium is what slows his healing factor. he would probably regenerate his penis, balls instantly. his healing factor apparently isnt the most advanced. i think deadpool and another mutant has a more powerful one(at least in last stand, he fought a mutant that instantly regenerate his limbs in 1 second, which wolverine cant do. as he cant heal from brain damage apparently.
The movies change it based on what creates tension or is funny in the current situation.
In X-Men the Last Stand he is able to survive disintegration that goes through people around him in about a second by constantly healing the damage back (and his pants repair themselves too I guess). And a similar thing happens when he survives a nuclear bomb in the Wolverine. In Origins: Wolverine he is able to heal back from an adamantium bullet to the head fairly quickly but loses his memories.
Deadpool is supposed to have a stronger healing factor but it still takes something like hours to a day for his hand to finish growing back after it gets cut off in his movie.
I doubt the comics are much better about being consistent with the amount of retcons and changing writers that happen.