Sure, I do it all the time. Send a text message to his email address. That will give him the proper email address to reply in a text to you. For instance, those using verizon can receive text msgs at phonenumber with a dot and vtext.com added. For sending images they can receive at the phone number with a dot and vzwpix.com

Example;
9998887654@vtext.com
9998887654@vzwpix.com

Others are;
@att.text.net for ATT
@mms.att.net for ATT
@mypixmessages.com for some Tracfones
@tmomail.net for T-Mobile