I'm usually the "short man" in the room when we swing with a couple or group. But, I've found out there are other things to worry about, other than my dick length. IE thickness goes a long way in making up for length
And the tongue, can make the night one to remember if used correctly.
It's entirely a male thing. Not much you can do there, except hang with it. I wouldn't recommend surgery, especially after reading follow ups from people who had the surgery. Maggie gave up 3 extra inches when she met me (as opposed to her ex), and she's still here 2 years later. So of course that does do something good for the ego of us short folks
Me in particular.
If you're looking to help ease his mind. Try some ALUM...Then see if he still thinks it's too small.