By December we would start gearing up for the new tax season, with the first four months of the year being the busiest in my line of work.I found a little bar close to the motel I was staying at. I was feeling extremely sorry for myself. The more I drank, the more I pictured Shelly and her big dicked paramour fucking on our bed. Then they both turn to me and make fun of me while they kept on fucking. I didn’t need a wild imagination to do that. It was fairly close to the reality that I had witnessed.I felt like a complete loser with nothing to offer to the world, especially to a woman. Shelly had told me that I was useless in bed. But to me, and I guess to any guy, that translated to being useless period. My bartender was a guy named Matt. He was a small man, maybe an inch or two shorter than my 5’8.At first, he patiently listened to my tale of woe, which was very helpful. However, he stopped being helpful when he went from being a listener to being an advisor. He said that guys like. I visited his house several times, we just sat and talked and had fun, nothing sexual. After a while he mentioned that he missed his daughter being at home so that’s why he liked c***dren being around. He then asked if I would dress and pretend to be her for a while. I was excited when he put me in her clothes and my little cock was sticking out when he put her knickers on me. So I wore a little gingham dress white cotton knickers and white knee high socks. He was very gentle and just played with me as if I was his daughter, again nothing sexual, but making sure I wore several outfits, with him dressing me every time. I never questioned why he just had her clothes in a bedroom and nothing belonging to her mother..When I visited him, I used to enter the house from the back lane, making sure that all was clear. Our little routine was that when I got there, I would get undressed put on a nightie and get into bed . He would come into the bedroom as if I had been sleeping and wake me up. I.
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