Dear Auntie Helga,
I don't know if this was my very, very, first experience with women's underthings but it was the most memorable. It was the summer of my 11th year and I was sent to spend a good portion of it with my grandmother in the Boston area. My parents were separated, not yet divorced but dad traveled and mom was putting herself into a business and "needed a break" for a bit. I was generally quite shy but could also be a boy - "rambunctious" was the word they used. My mother's last words in dropping me off were "I don't want to hear one single complaint from your grandmother or you will be sorry... do you understand me"? I don't recall my exact response but am sure it was acquiescence of some sort.
My grandmother was young and peppy for her age - a fact that probably helped her to offer to take me. She only just in her early 60's at the time and I had always been a bit enamored with her. We visited some but not enough for me to be comfortable. Though obviously older I had always thought her pretty. I knew for a fact that she felt "today's parents" were too permissive in general. I had heard her more than once saying such to mom. My mother was no pushover but I expected grandma to be stricter. However I had no anticipation of what occurred.
I had gotten there somewhat late the first night and was sent off to bed pretty quickly. It was the next day when grandma said we would have a talk. The next morning after breakfast I showered and she asked me to meet her in her room. The house in general was big and her room was a very large one. She sat on the edge of the bed and motioned for me to sit next to her to talk. I had totally noticed that spread out on the bottom of the large king sized bed was an outfit of feminine underthings - panties and a slip both satin and nylon type.
After initially noticing the garments I turned most of my attention to my grandmother who proceeded to both give me somewhat of a lecture as well as to ask a few questions here and there. She asked me a bit about my "behavior" at home - did I ever cause problems, not do my chores, etc. etc. This was a bit of a turn in the conversation and I recall looking down and being very uncomfortable as I admitted to her that this had happened. Of course I was not telling her anything that she was not fully aware of - she just wanted it said out loud.
Part of her was somewhat warm about it all. She said she was sure "we" were not going to have those difficulties this summer. She said she does not tolerate disrespect. I can still recall just looking at the floor and feeling small. It was at some point just then when I noticed she had picked up the panties from the bed. She just held them in her hand while she kept talking. She was generally going over rules and expectations as well as telling me some of the potentially fun things we would be doing during the summer. At one point she stopped and asked (I still recall this like it was yesterday) "Do you think things are going to work out for us this summer sweetheart"? The word "sweetheart" itself made me feel incredibly small - looking back I expect that was the intent.
I was pretty much just feeling awkward, shy, and a bit dumb. I was hoping the "talk" was near over when it got a lot worse. She told me she was going to ensure that we had no problems this summer. She asked me if I thought that was a good idea. At that point I was virtually agreeing to everything and am sure stammering a bit. It was then that she dropped the bomb. I am always amazed at how clearly I can not only recall the events but her precise words. I have thought of them like a million times.
Still holding the panties in her hand she said "Take off your clothing for me honey". You might think I would have balked or said something or objected in some way but in that moment I was way beyond any of that. I was under the tutelage of a strong, confident, maternal force and I did as told. I am sure I was more than beet red just standing bare naked in front of her. She was not harsh or aggressive - in some ways quite the contrary - gentle and soft spoken but clearly in total control of me. I was in a sort of dazed, shocked, compliance when she held open the panties - clearly indicating that I needed to step in to them. I was humiliated and embarrassed but was on a sort of "automatic" as I stepped in. I was even somewhat relieved to be at least "covered" in some way. Moments later I was "asked" to raise my arms and the slip was pulled over my head.
There was almost no talking at this point - certainly not from me - only a few motions and directions from my grandmother. She led me over to her dressing table and sat me in front of the mirror. There was not a big "make up" thing but she did sit me there and brush my hair for a bit. After that she took some perfume and dabbed a little behind my ears. In a soft clear voice she said "I don't think we are going to have any difficulties at all this summer, do you"? I can recall that I felt too ashamed (or tongue tied) to really answer.
That was an introduction for me. I had seen and touched feminine garments before that but this was a whole different thing. It impacted me greatly. My grandmother did not keep me in garments all the time that summer and much of the time was "normal" and quite fun but there were times when she would give me something to put on. Sometimes it was because there was a transgression on my part and it was "punishment" but there were other times (at least this is what I think) when it was more "preventative" and to keep me in my place and respectful of her and her authority. I confess that I did not question that during that summer or well beyond. I was grateful that for the most part this was a "private" punishment. With perhaps one or two exceptions I don't think she told others.
It is funny - what was once a source of punishment is now more a source of comfort.
Thank you for your letter Jim. I can certainly see how this was the most memorable, a simply perfect introduction to petticoating done with both love and determination. Your grandmother, bless her heart, did this to help you and it obviously worked, your polite and respectful responses to her as well as your letter to me speaks volumes of its success. Our readers will understand why as an adult you can look back fondly at the experience and feel comfort at this special memory and we appreciate your sharing it with us.