I happen to come across a virgin guy and he's interested in being a bottom. We've tried but he's too tight, or rather he's too timid of the intrusion. We both enjoy each other's company and want to get more close......how do I go about, please guide me

 

You must be very patient.  Some people may take a long time before they start enjoying anal sex. They have to learn to relax and focus the attention somewhere else.  Try using lubricants and also try touching other parts of his body. That way he will focus on the pleasure rather than the pain.  The key is to learn to relax.  Good luck!