So many posts here on this subject and for those of us that do shave, we all know it is a non-event. Shaving, in and of itself, does't out you as gay nor does it out you as cross dresser. I bike and have chosen to shave for that AS WELL AS shaving for cross dressing. No one asks, no one cares. Except....
Your wife or girlfriend will notice and will ask. The WHY of your shaving is what will make her care or not. If you are in a DADT deal or if cross dressing bothers her, shaving is just a reminder to her that you are a cross dresser. If you are not out to your wife/gf then shaving WILL bring up questions.
I'm willing to bet that no wife/gf will actually care about shaving, if you're doing so for some sport related activity (biking, swimming, triathleethon, etc). If your reason is for cross dressing, then the only person you must address is the one you love. The rest of the world is a don't care.