On the outside, I am alpha type of guy. Grew up in sports. Went to college for it. Went into law enforcement. And other similar career paths. I am currently married and don’t know what to do. I have been crossdressing on and off my whole life. From a young teen to even now. I have always worn and stole clothes of women in my life from my mother, to cousins, to girlfriends, and now my wife. EVEN HER MOTHER ugh. I have cheated on my wife a number of times with men. Mostly oral and only bottomed for one man. I came instantly as his cock was in me. Every time. It was the hottest thing I’ve ever done. All while wearing her lingerie. She’s much smaller than me so it was stuff I really had to stretch to get in. I also have tattoos. I’m not small or petit. Not fat. Not a humongous body builder. I’m 511 195.
I have never really felt comfortable with myself. Always comparing myself to others. I’ve always been a better judge of what women should wear out or wear getting dressed up to look sexy.
I think what I’m trying to get at, is to ask you for guidance/ help. I don’t know what to do. I’ve never went this far down the rabbit hole. And the deeper I go the more I feel like I’m slipping up hiding this side of myself away. I always thought “you would never pull it off you’re too manly. You will look dumb because you’re not small or petit”. But I believe I could do it. I’m not afraid of the process or what it will entail to become this but I am afraid of how easily I am able to just be willing to walk away from my life now. I’ve noticed the more I research and read the more tired and exhausted I am of my current lifestyle.
Never dabbled too deeply. Been tied up. That about it. BUT I will do what is demanded of me.