As far as 5 years old I was drawn to womens clothes and throughout my childhood and into my early 20's I regularly dressed up as a girl. My features were always somewhat feminine and during my teen years I was usually noticed by men that knew about crossdressers, they could tell. My earlier sexual experiences were with boys my age and I always adopted the feminine role and as I got older, even though I liked women I dressed up as a girl and later in my late teens I had sex with a few men while looking feminine. Later in life I got married and my wife supported my dressing up so during my first years of marriage I shaved my legs, plucked my eyebrows and had my hair styled in a feminine fashion but still able to look boyish around friends and family that didnt know. Eventually this caused resentment in my wife and 8 yrs into our marriage she slept with someone while visiting family mainly because she wanted to be with a "real" man as she put it. It was painful but 5 years later I started getting into cuckold porn and eventually convinced my wife to date for money as a sugarbaby and enjoy herself with other men. She dated older men with $$ that gave her gifts for her time and took her to fancy restaurants, expensive hotels etc.. this was very erotic to me but I am curious how it all connects. Im not sure what everyones thoughts are as to how my years of dressing up and trying to look feminine concluded in me having my wife date other men, even tho the 1st affair was so painful to me...how did it switch and why? thoughts welcome.