I have been a life-long closeted crossdresser. Until recently, the only other person to see me dressed as a woman is my Mother, she caught me wearing her bra and panties when I was sixteen. Over the years I have developed a nice wardrobe, sexy lingerie, some really nice shoes, and some wigs. I hide everything in my office. I own a small office building with a small efficiency apartment where I keep it all. I have been married for almost twenty years, we have three kids, nice home, etc. To look at me I'm the last kind of guy you'd expect to see wearing a dress, let alone having his painted lips wrapped around a big juicy cock.

After years of fantasy I finally worked up the nerve to be with a man. The family was away and I was on my own so I posted to Craigslist. I was amazed at how many responses and finally clicked with a guy. After a few emails I was on my way to meet him. I was dressed to the nines, garter, hose, stilettos, and sexy makeup. I am quite passable and was utterly pleased at his response when he answered the door. He liked what he saw but quite honestly there was little small talk. Just inside his door I was on my knees and face to face with the first hard cock other than my own I had ever seen.

I became a cocksucker for life the moment my lips parted for his musky, heavy hard cock. It was everything and more that I had imagined. I took to it naturally and had him on the verge in no time. He slowed me down and had me remove my dress. We climbed on the bed and after a little lube he slowly eased his hard cock into my tight asshole. The sensation wasn't painful as I imagined, just very uncomfortable at first until the head of his cock penetrated my ass. Then he slowly but forcefully pushed deep into me, working in and out until he was pumping his dick hard and deep. He grunted as he uploaded his cum deep in me.

I felt a wild array of emotions, fear, guilt, joy, disgust, elation, you name it. I quickly got myself together. I used the bathroom to fix my makeup and hair and left immediately after. I nervously drove home and only breathed a sigh of relief as I pulled into my garage and closed the door. I took a long shower and relived the evening in my mind. I now more than ever want to please men every chance I get.