How did you manage to get ******, with him crying at the same time?

That's awkward.

FYL, to both you and the guy. For some people, sex can be a traumatic and unpleasant experience. I'm not going to laugh or insult somebody who finds something upsetting. Maybe he wasn't ready or maybe sex isn't for him, full stop. That's okay too, and it's a shame society puts so much pressure on people to have to have sex. Especially men, where if they don't want to have sex or have a lower sex drive it's seen as them having something wrong with them. (It also sucks that society shames people who have sex 'too much' or 'wrong' by its standards too. Basically, there's only a certain type of sex seen as acceptable and I very much doubt most people actually fall into that.)

Why would you continue having sex with someone who was crying the whole time???? Why wouldn't you stop and ask if he was okay (which from your FML, he clearly wasn't)???? *facepalm*

and what exactly do you say to your parents after that ?! how awkward

How manly is he lol

For his first time, maybe the clamps shouldn't have been so tight....

Those had better be tears of joy, ************.

Sounds like someone wasn't ready to play grown-up.

The crying was either a result of childhood sexual abuse, or creepy overbearing parents who brainwashed him by repeatedly saying having sex will condemn him to hell.