I completely know what you mean. I underdressed for years. Before I got married, I took the proverbial leap of faith and told my wife. She already suspected and accepted and supported me. I?m now retired and dress daily and I both love it and it does feel so natural and normal. She?s been so helpful with advice like makeup. I daily enjoy the daily question...oh what to wear, what color bra, panties, etc. when she shops, she often surprises me. She teases me about my special love of underwire bras and hose.