Does it hurt a guy when he loses his virginity

If a guy experiences discomfort or pain when he has his penis in a vagina or anus, he's doing something very wrong.

The hymen is not made of sheet steel. In any case, many women don't have much of a hymen to begin with, and the hymen of others will have been torn or stretched by sports, other physical activities or masturbation. Some women do find PIV sex uncomfortable to some extent the first time, but it's a myth that it's always agonisingly painful for a woman to lose her virginity.

A virgin vagina will be a snug fit, but it's not like trying to cram your dick into a knothole. If the guy knows what he's doing and if the girl is definitely in the mood for sex, there should be a lot of natural lubrication, so the guy shouldn't experience a lot of friction, especially if he's using a condom.

There is something called vaginismus, which is an involuntary spasm of the muscles surrounding the lower third of the vagina. This can make PIV sex extremely uncomfortable for the woman, but as far as I know, the vagina just feels very tight to the man.

It seems to me that there are two main possibilities. Either your friend is bullshitting and his sexual experiences are completely imaginary, or he wasn't using a condom, and the girls he's had sex with were totally dry because he's totally crap at sex. If the latter is the case, you can be sure they found the experience even more uncomfortable than he did.

Not at the time but the next day my dick felt a little sore... in a good way though.

You're sure he's talking about himself and not the girls who were experiencing pain?

Guy's either really bad at sex, or is just lying. Did he lose his virginity to a blender?! Even if your girl is really tight, it doesn't hurt.
Losing your virginity as a man doesn't hurt.

Your friend either is full of shit or was really bad at what he was doing.