He should be patient, supportive and not squeamish
Relax
Use lubricant
Go slowly
Communicate honestly with each other throughout the process
Don't expect pleasure right away... but it's there and waiting

Quote by honeydipped
i've often wondered this as well. i've seen a number of profiles where trans members have felt the need to explain why their selected gender doesn't match their avatar in their bio. if they had the ability to select transwoman/man, that could be eliminated. i also think fluid would be a welcome addition.
Quote by Jimwillhavefun
She needs to clear her cache files in whatever browser she is using. Make sure she logs out of any sites she is in first. Then she can log back in and it will refresh any connections to files it needs. This is common if she has stayed logged in too long. The cache gets full and no longer makes the connections.