Forced To Wear Her Panties: A Sissy's Descent

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I was brought up in a village in Hertfordshire in the 1950s and 60s. I lived with my mother and sister, my dad having taken off to find some excitement when I was quite small. My sister Sally was about a year older than me. Sally tended to look down on me, both because of her age and the fact that I was a mere male! Mum, while she was very kind, was very Victorian in her outlook. She tended to regard any discussing of sexual matters, almost anything below the belt, as rather dirty, and never tried to give me even the slightest hint about puberty or the ‘Facts of Life’!

It made me feel a little sexy sometimes as it swung across my shoulders if I wore a tank top. Every night I’d have to sit there and brush it to bring out the oils, she said. Long hair takes time, she said. Do it right or not at all was her motto. No wonder I never wanted to keep it nice before but then, I had all summer, only school would be starting soon and I knew she wasn’t going to let up on the hair or anything else. She seemed absolutely relentless about my grooming and deportment. I suppose it wasn’t too bad but I was beginning to have some doubts about myself lately. I felt, I don’t know, different somehow but just couldn’t put my finger on it. I think I was acting differently too, I don’t quite understand it! My sister made good her promise to totally ignore me in the future, while my mother reminded me of my sins on a daily basis for many months. In the end, completely fed up with the nagging and bad atmosphere, I went into an Army recruiting office and signed on with the Boys’ Service. My mother readily signed the approval forms, saying that it would make a man out of me! I was about to graduate from grade school, 14 years old, and ready to conquer the world. Mom and Dad said I had an attitude problem. I saw it as more of an expression of independence. Well, they were going to Europe for a year because of Dad’s job and I was to stay with Aunt Rose. She was my father’s sister and had bankrolled his import business. He pretty much did things her way or not at all even though he was president of the company. I rather say that as whipping out on his part but he was my dad and I had to respect that and all the money he made anyway.As soon as I was free the 5th of June, Mom and Dad were off to New York and London and who knows where else. Well, that was fine with me. I could use a break from parental supervision. I was a dyed in the wool slob and enjoyed it immensely. You know, sneakers, hole in the knee jeans, tee-shirt, long, dirty hair, the hoop earring in the left ear, the usual. Aunt Rose was pretty bossy though and I admit that I was a little afraid of her too. She was sufficiently larger than I was so she could probably put a hurt on me. She seemed kind enough when I was dropped off at her place though. I think that may have just been to fake me out though. As a teenager I always used to spend about ten days each year with Cousin Clare and her parents. Clare wasn’t actually my cousin, but her mother and my mother were at school together, and it was a convenient way to refer to her. Clare was an only child. Oh, sorry,” she said. She relaxed her grip. “Is that better?” She gave it a little rub, and I just gulped, and nodded ‘yes!’ At the house I was shown to my room, a different one from normal. It looked like a large box-room and had several extra items of furniture, including a big old dressing table. Suddenly I almost jumped out of my skin and my heart stopped as the bedroom door opened, and there in the doorway staring at me, was my mother, with my sister Sally peering right behind her!

Sally and I lived in a sort of truce most of the time, with a battle likely to break out at any minute, while our mum tried to keep the peace. However, Sally was a clever girl and eventually went to college to get a degree. She also had inherited Mum’s fastidious attitude to hygiene, washed her hands frequently, and she bathed far more frequently than was necessary in my view! She also changed her clothes frequently, especially her underwear. This was to my advantage as she put her discarded underclothing in the laundry basket in the bathroom. At the time of the following exciting adventure we were sixteen, but I was a few months older than she was.Clare said again, “Come on Tom! Don’t worry, I won’t tell mummy, but I might if you don’t let me have a look!” This exciting adventure was repeated every bedtime. Aunt Frances had a large washing machine and I don’t think she examined my pants before putting them in the wash, which was just as well! All went well for a few days. Then the sky darkened and the rain poured down! Uncle Mike was at his office, of course. Aunt Frances was visiting some friends for the day, and Clare said she would be at the farm attending to her pony until lunchtime. I couldn’t go fishing in that weather, so I said I would stay at home and read the set book from school, which I’d been told to read in the holidays. (It was The War of the Worlds!) My bummy old blue jeans became history. She threw them out. Aunt Rose would help me with the housework but I did the washing too. Since I did the washing, I had apparently gotten an appreciation for keeping myself clean too. She taught me how to separate things and how to treat various fabrics, how to fold and what to fold and what to iron. Oh yes, she taught me how to iron too. I found that once I understood how to flatten things and maneuver sleeves and what temperatures to use, it wasn’t so bad but that was a painful experience nonetheless. SUMMARY - Keenan was left in the care of his father’s sister while his parents went to Europe on business. They left him with Aunt Rose to teach him some manners and improve his dress code. Then they invited the new Keenan to spend the summer in Holland with them. The business they came home to was getting used to their new teenager. As far as I was concerned, I was beginning to look darned feminine to go along with all my girlish chores. I didn’t mind helping Aunt Rose out but these feelings I was having were most peculiar. I believe I was becoming accustomed to the gentler side of life and continued handling of Aunt Rose’s lingerie was having a peculiar effect on me, like, I actually caught myself wondering what it felt like to wear something so soft and silky. I noticed I wasn’t complaining about stuff any more like I did when I first came there. I just sort of accepted things now as they were.