My first time out was at a good friend's (male) Halloween party. I went all out and had the greatest time. All the women wanted to know who did my makeup, what shade was that on my nails, what brand of stockings I was wearing and all that. I had so much attention from the ladies that the guys were all getting jealous.
If you've never been out in public then take the opportunity. You have an accepting wife so enjoy the experience. Just go with the flow and if need be, when you are asked delicate questions camp it up a bit and they will never know the truth.