I have secretly crossdressed since I was a young teenager. Until recently only two people have seen me wearing women's clothes. My mother caught me struggling to hook one of her bras behind my back when I was sixteen. From outside her bedroom door and to my utter shock she calmly said that there is an easier way to do that. I stood frozen in fear and shame as she walked over and took her bra from my hands. She gently wrapped it around my torso fastened the snaps in front and spun it around helping me slip the straps to my shoulders. She adjusted the straps and padded the cups with some hose from her stocking drawer. I was mortified when she asked me if I wanted to try on some makeup. This happened just once and we never spoke of it again. A few years later a friend of my parents came by the house and caught me fully dressed in the garage. I was utterly embarrassed and he was nice about it and apologized for intruding. He never said a thing.
Years later I have kept my secret from everyone else, including my wife and kids. I maintain an extensive wardrobe not too far my office. I own some apartment buildings and maintain a small place in one of them devoted exclusively to the rare opportunity I get to dress up. No one but me had ever been there. I had always wondered about being with a man, but for the longest time the masturbation sessions were enough for me. Oh my God. What the hell was I thinking? I have missed years of cock.
A few months ago I put up a profile on a mature crossdresser site and was soon inundated with requests to meet. I connected with the perfect guy for my first blowjob and invited him over to the apartment. He told me I looked hot and that I was a naturally talented cocksucker. He showed me how to lick and suck his cock and balls. Holding my head firmly as he fucked my face and with no warning came in my mouth and pulled out finishing on my lips and chin. I was mesmerized by the experienced and was intent on remembering the taste of his cum on my tongue before I swallowed it. About a month later I gave up my ass. Since then I have given about thirty blowjobs and been fucked a half dozen times by five different guys. I have remained utterly discreet but have been sneaking away from home and the office a bit more than I should. But right now I cannot get enough cock.