from Derek

Dear Auntie Helga,

I was visiting my neighbour, Aunt Molly, like I would do on any other weekend. As she had lost her parents and was staying alone, I was a pampered boy and a 'Prince' whenever I stepped into her house. I had to abide by all the rules and put up good behaviour at all times but I was never given a "No" for an answer if I asked for something reasonable.

I was nearing 14 years old. She was twenty-two. I was helping her arrange her wardrobe. Suddenly she fished out pantyhose from one pile of clothes. I quickly related them to trousers. Out of natural curiosity, I asked why she would wear them. She smiled and said it was for women. I kept saying no and continued to argue. She challenged me if I could wear it without help and prove it to her. Her smile in every sentence suggested she was enjoying my childlike persistence. I immediately took up the challenge and said I would change from my shorts to her 'trousers' in a minute and return. She tried to stop me as I rushed and locked the bathroom door. She knocked and yelled out (never had I made her raise her voice); asking if I was wearing underwear. I answered, "Yes of course!" She warned me and said, "I will check if you have damaged my pantyhose on it when you come out."

I slipped down my shorts and with a little difficulty, managed to wear the pantyhose all the way to my waist. I unlocked the door and bent down to reach for my shorts. I noticed my underwear and my legs were totally visible! I have always worn briefs so it was embarrassing for me to walk out like that. In the hurried argument I didn't realise it was transparent. I quickly locked the door before I could be seen and began to remove it.

Aunt Molly knocked the door and asked if I was done. I told her what I noticed. She laughed heartily and said to leave the pantyhose on and wear my shorts over it. I did so and I came out. I expected a lot more laughter but she just went down on her knees, rubbed her hands on my legs, feet and then pulled up my t-shirt. On my waist towards the left, she pulled up the pantyhose and then reached for my underwear. She was happy I followed her instructions. She asked if I was convinced that those were not ordinary trousers. I agreed instantly. I wanted to change but then she insisted I leave it on till I go home.

This is exactly how it began in the 1990s for me. I used to frequently wear her pantyhose. In a span of two months, she gifted me a coffee colour pantyhose saying it was all mine and told me it was on the wooden shelf with all my other toys.

One day she asked me if my parents knew about this. I said no. She said that she saw me hating the time when I was dressed as a girl in school plays. So she asked why I was wearing her stuff. I said I disliked being made fun of. I always loved feminine attire. I urged her not to tell my parents. She agreed and said that as long as I live in accordance to her rules, all was well taken care of.


It was a Friday afternoon again. I was home from school. After quickly gobbling up my lunch, there was a rage of fur gushing through my stomach. It was the day of the week when I would finally get my hands on my pantyhose. No one except Aunt Molly knew about this. Mom insisted I change my footwear but I was too excited as I had waited 4 long days.

I was sixteen years old now. I had been doing this for many years. What was so special that the excitement today was only multiplying? Aunt Molly had promised me a while back that she would let me try all different colours of pantyhose on a lucky day if I would not question her about them over and over again. But I was not expecting this today.

What was strange about Aunt Molly was that she frequently used to talk to herself. Our balconies were placed in extreme proximity. Three days ago she had washed a set of clothes that her friends recently gifted her. She was putting them out to dry in the sun. Her body structure and mine is highly identical. But her friends in Germany had gifted her still smaller size of clothes. I overheard from my balcony when she murmured to herself "I will let my little Derek put this entire set on someday."

I could not believe my ears. On one hand I was trying to hide from my neighbour. Mom was yelling out as I was not responding. Hearing Aunt Molly and looking at those clothes got me a bit aroused. But I was very scared of my mom. So I rushed inside immediately and resumed studying.

Coming back to Friday, I was just waiting to say hello to Aunt Molly. I rang the doorbell and she answered the door quickly with a smile. I greeted her and rushed to the wooden shelf. As soon as she locked the door, I reached my favourite toy, my coffee colour pantyhose. She was laughing when she saw me rushing to the bathroom to change.

I was more than content with the nylon on my legs. Aunt Molly was friendly and pampered me but rules are rules in her house. I was never to wear my pantyhose without my underwear. She periodically kept a check on me. Once I had failed the test. I was punished with no pantyhose for three consecutive weekends.

The moment I came out of the bathroom, she pulled up my t-shirt and checked for underwear on my waist. She then pulled down my t-shirt, played with my hair and said, "Don't you get tired of white colour?" We laughed and she took me to the bedroom and brushed my hair for over ten minutes talking generally about my week at school.

Seated like a girl with one leg over another, I slowly looked around for what I was expecting. After three trials I located the set. It was in the corner of the room. I stopped listening to Aunt Molly and began imagining myself dolled up in that dress. Suddenly, a pat on my back put me back into my senses and I stood up to play with her. Hide and Seek was what we enjoyed but I could not take my eyes off those clothes. She had noticed me and realised I was very distracted.

She took a break and went on to prepare tea. I took the opportunity to touch the gift she had received. It seemed to be a sleeveless one piece dress which would cover me from my chest till my upper thighs. It was sort of skimpy. On turning it around, the leggings attached to the dress fell out. I could not afford to be caught so I quickly put it back as it was. Luck was on my side and I got away with it. I was happy not wearing it as long as I didn't get caught.

Saturday evening, there was no one at home. I was reading and bored. I went to her place. She was tutoring a student in the drawing room. I was told to wait in the bedroom and play with the train set. But my eyes were only looking for the dress. As soon as I found it, I quickly came in front of the mirror, put the dress in front of my body and admired myself. I had ample time so I separated the leggings. They were so soft I could wear them day and night. I was a bit aroused but I didn't know what was happening to me at that point in time.

So I kept the dress away and proceeded towards my one and only pantyhose. I realized I came unprepared as I was not wearing anything underneath. She had checked me just yesterday. So I decided to quickly wear the pantyhose below my shorts and remove it before she finished tutoring. I just wanted to make the best of the weekend.

I let my shorts fall on to the floor. My penis was erect like never before as I was in the bedroom this time and the door was not lockable. I started wearing the pantyhose but found it difficult to adjust it due to my erection. I now understood why she taught me the importance of underwear. This was just the second time I wore it on my bare skin but first time in front of the mirror with a strong erection. My penis looked ugly but when I turned around, my rear end looked fabulous. I literally started admiring myself in the mirror. My t-shirt was also off. I remembered the door was open so I quickly got my thoughts back together and dressed normally. I waited for her to finish tutoring, played a little chess with her and returned home.

Sunday afternoon would get very lonely and hot. I visited her and she just woke up from her nap. She smiled and told me to get dressed for high tea. It was a code which meant I need to wear pantyhose after which we would have tea and she would comb my hair and apply a little powder on my face. I was waiting to do the exact same thing as I did the previous day. Without underwear, I rushed into the bathroom and wore the pantyhose. I wore my shorts, controlled my erection and came out. I wasn't expecting a check.

We had a good cup of tea. She briefed me about her trip to Germany. She showed me the dress which I had been eying for a long time. But what I had not seen was matching panties and bra which she removed from beneath the top portion of the dress. The pink panties with tiny flowers were perfectly my size!

I was highly aroused. But I was seated so no harm had been done. She told me to hurry up with my tea and get the utensils back to the kitchen. I thought my erection would subside but it became only stronger. A huge bulge could be seen. I could not even stand. She raised her voice and told me that if I don't get the cup inside and remain defiant, I would be punished. I did not know how to explain myself. I got up and pulled my t-shirt way down to cover myself. It worked as she didn't notice. But on my way out, I had to pass her the second time and I was asked to lift the cloth on the floor. I did so and the pantyhose ripped. A distinct sound was heard by both of us. We both knew the end of the pantyhose was near. But she could not stop laughing. She told me to stand back-up and I was still in squat position. She told me to change and get her the pantyhose. She wanted to see if she could fix it. I rushed to the task. I was lucky again. But it was short-lived. Before she could find the torn portion, she noticed the front end of the crotch was wet. She asked me if I had wet my pants. I said no. She frowned and looked at my shorts. She saw my partly alive erection and demanded me to show her my underwear from my waist. I tried to fool her by showing the inner portion of my pants.

I committed two errors. One was disobeying. Second was lying. She said I was a pig and told me to stand in the bathroom for 30 minutes till she decided how to deal with me.

She returned with a cane in her hand. I knew what to expect. She asked me how long I was going to be at her place as I can't go home with red swollen palms. I said I had two hours. She told me to stretch my hands forward and I got 5 strikes on each hand. I thought it was over and burst into tears. But nothing was happening as I expected. She did not hug me to comfort me like before. She turned around, locked the door behind her and switched off the bathroom light. I ran behind her but I was too late. I knew I pushed my luck way too far. I kept crying, pleading and knocking. She came in after a long time and said I was not a kid anymore. My punishment was that I would not be given new pantyhose and I was to forget about all of that completely.

more to come...


Thank you for your letter Derek. What a charming and delightful childhood introduction to petticoating and thank you for sharing. For many boys, pantyhose with their silky texture, are hard to resist, something your Aunt Molly knew all too well. Her playful good hearted nature must have been a joy to experience and I know our readers will enjoy the continuation of this fascinating story.

Auntie Helga

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Letter 10