wow what a poor attitude towards your friend. Obviously he likes her or he wouldn't have waited three years. Why does it matter to you if she is lying about being a virgin ?

To answer your question; no pain. Just slightly tender for a couple of minutes after.
How you feel afterwards will depend on a lot of things as others have said.

With that being said why not kill this girl with kindness. Quite being a nag to your buddy and just tell him you don't think she's good enough for him, but if he is happy that is all that matters. then leave his love life to him, stop trying to be a third party in the bedroom, that's just wrong.

Depends on what kind of 3rd Partying he's doing. It's not wrong if it involves a video camera or some double-teaming.

if ur buddy wants i can join in on a 3some and give him some pointers

what's wrong with you two?
he said she's ugly in the first post.

:facepalm:

nothing wrong with a paper bag!

that what I woulda figured. I've been with 2 virgins, one was on top, went in fine, just a little bit of pressure then no more cherry, second one she was on top at first but she couldn't get an angle that worked right for her, used the edge of the bed technique, went in no prob after that. neither bled as far as I know

pics or it didnt happen

It's not like some promiscuous women don't have tight vaginies either though.

so he really can't judge based on that