Masculine Desires Feminine Clothes
I once knew this guy who wore women’s panties to board meetings. He was the head of his company who had a liking for satin panties under his $2000 silk suits. He said that he liked the way they made him feel when he knew he was wearing them. He loves designer clothes and always buys the best, most expensive ones he can find. He has a tailor on his payroll to make his panties and most of his other clothes, so they have the best fit. How did I get to know jet-setting mogul in an Armani suit and Vera Wang camisole?
He and I had known each other since our college days, when we had to pool our money to go to the local burger joint. He’s parents had money, yeah they were loaded, but they only gave their son a small monthly allowance. They wanted to teach him about the “real world”. I never understood this reasoning, because he was going to get the bulk of his inheritance when he finished college anyway, so what was the point of giving him a “poor experience” just for college? Anyway, he always seemed broke and I would ask him where the money they did give him was going. Usually, he would avoid the answering the question and point my attention in another direction.
Finally, I confronted him about it. We were sitting in his apartment one night when I said that I was tired of paying for everything and told him that he better start pitching in some gas money or come up with a really good reason why he couldn’t cough up some cash. He looked very uncomfortable and said that he was afraid that I wouldn’t like him anymore if he told me the truth. Suddenly realizing that there was something serious going on, I tried to reassure him that I would like him even if he had this huge drug habit or the school bullies were extorting him, or he was supporting a wife and kids in some far away place. He thought about it a moment longer, then said that I could never say anything to anyone about what he was going to show me, even if I didn’t agree with it. I nodded and followed him into his bedroom, wondering what the hell could possibly be the issue. He led me to his closet and told me to look at his clothes.
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Dress You Up
At first, I didn’t understand what I was supposed to see, and then I realized slowly that his closet was full of beautiful clothes. Women’s clothes. My jaw dropped as I stared at all these outfits. I asked him if he wore all these. He nodded and then said again that I promised not to tell any one. I promised again that I wouldn’t tell anyone, and then asked him what size he wore, hoping that we could share all these beautiful clothes that I could never afford. According to what he told me that night as we sat in his overflowing closet, he had always wanted to wear girl’s clothes, but he wasn‘t interested in sex with men. He just loved make up, heels, and girly things. He had decided when he got to college to indulge his passion and set about acquiring this extensive wardrobe. He had the best of everything. Brand name make up, shoes, underwear and bras. Oh my!
He was so happy when I told him that I was cool with his cross-dressing. After that first night, the two of us had fun dressing up together and going out. We would go to nearby towns. Although he could pass pretty well, he didn’t want to take the chance of someone recognizing him and telling his parents. No one ever did though. Then our senior year we went to Mardi Gras and had a blast walking down Bourbon Street and finding out he was all man under those panties!
Still Pretty After All These Years
After college, we drifted apart. He got a high powered job somewhere in New York and began working his way up the corporate latter. I got my own career and life just kept moving forward. I see him every now and then on some business talk show and wonder what color underwear he has on. He and I exchange Christmas cards and he still alludes to his secret life in his short notes. He laments that he can’t wear a nice bathing suit and sarong on the beach when he goes on vacation in Ibiza. He says that someday he and I will return to Mardi Gras and New Orleans. Although I doubt that it will ever happen, I always tell him that I will meet him there.
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