Dressed To Please
I'm going to share a confession that, in the past, has drawn the whole range of reactions from, "You lucky boy!" to, "You poor thing, you must be so angry and upset." I'll tell you the last of these is wholly inappropriate; and I say that having had over forty years to think about it. When I was a young lad (best if I don't say how young), I had a great aunt, Gwen. She was in her fifties and widowed. I used to love to visit her because she fed me lovely home made cake, and I used to get some lovely glimpses up her skirt (if I was careful). I particularly liked the old fashioned bloomers she used to wear, and it was with her that I came to appreciate the delicacy of lacy slips. One day when I was visiting, she started to talk to me about her life. What had been her hopes and dreams, and how things had actually turned out (I think she was feeling a bit down at the time). Anyway, she mentioned that, despite having a lovely son, she had always wanted a daughter to love. I think I always listened sympathetically to Aunt Gwen and I must have shown some understanding of her depth of feeling because, out of the blue, she said, "I don't suppose you would consider being my daughter when you visit?" This was such an off the wall question for a young boy to deal with that I asked her what she meant. She said, "Would you dress as girl for me, and act as if you were my daughter?" I asked, incredulously, if she was serious and she said she was. Well, it was an interesting idea and, having established that this would just be between her and me, I said I would give it a try. It turned out that she must have been thinking about this for a while because she took me upstairs where she had girl's clothes my size! I was a bit embarrassed as she helped me out of my boy's clothes and into the knickers, knee length socks, skirt and blouse (in fact, a regular school uniform) that she had there. There's no denying that it felt good. Very good! So good, in fact, that there was a very unfeminine "lump" that wouldn't let the front of my skirt lie flat like it should. "Hmm. We'll have to do something about that before you can be my daughter," she said. She had me lie back on the bed, then lay down beside me. Pulling my skirt up, she took care of my rampant male member. As she worked, I went into a sort of trance. The sensations were so powerful; they were like nothing I'd ever experienced before. She kissed the side of my face and said, "I've often noticed you peeking up my skirt. Did you like what you could see?" I croaked, "Yes, but I could never see enough." To this she replied, "Well, it's going to be mother to daughter from now on, so there'll be no secrets. You'll get to see it all." That was the trigger point and I messed on my new knickers. "Luckily," said Aunt Gwen, "I thought this might happen, so I've got some fresh knickers for you to put on." She got me out of my old ones, cleaned me up and helped me into a fresh pair. Now my skirt sat as it should. From that day until I went away to college, I would regularly go visit Aunt Gwen and be her daughter. She would invariably have to "tame" me first, but usually without messing my clothes up like the first time. True to her word, we did share everything like mother and daughter, so I got more than my fair share of seeing her in and out of her underwear. We never went further than what was necessary to make my clothes sit correctly. Aunt Gwen just needed her "daughter" and what I got back in return was more than a fair trade as far as I was concerned. Sadly, Great Aunt Gwen is no longer with us, but I will always think fondly of her and those wonderful days I spent as her daughter.
— Brian, 59