Bobbie's mother and sister discovered that Bobbie behaved much better when made to wear his sister's panties and dresses. Bobbie was terrified that someone would find out that he was a petticoated sissy, so he had to try to be as convincing a girl as possible; but ...
Copyright 2003 Bobbie838
Mum always left my underwear perfectly-folded in my drawer, Mary Poppins-style.
On the right side of the drawer was my ordinary, boys' underwear: mainly Y-fronts, other underpants and boxer shorts in various boys' colours.
On the left...were my sister's cast-off panties - girls' underwear. My heart sank slightly as I was reminded yet again of this new, encroaching, aspect of my life.
Cate's used panties were worn, but not worn out and comfortable, but of course without the convenient opening in the front for peeing, which was the first thing I noticed the very first day Mum instructed me to put them on...
***
Since that day my life had changed dramatically. I had become less cocky, less aggressive, less badly-behaved, but also less sure of myself as a growing boy. My feelings had become confused as I struggled to cope with two conflicting identities. Did Mummy really want two daughters? Didn't she like me as her son? Would she love me more if I changed into a girl, instead of just being dressed as a girl occasionally?
I wanted to be loved by my mother and I loved her deeply, but surely she understood the embarrassment and shame involved in my having to wear Cate's pretty panties? Surely she realized that I couldn't go out and play with my friends if I was wearing a skirt or a dress? Surely she didn't want me to be teased and mocked as a sissy boy by my buddies?
I used to dream at night that I was a real girl and that everything was perfect and lovely in my family, but then one of my friends would appear in the dream and say something like, "You're not really a girl, you're just a little fairy boy!". And I would wake up with a shock, and quickly reach my hand down to my groin to check what I really was.
***
Cate's used panties were different from my underpants. They were girly. They were mainly cotton and in girl's colours: pink, light blue, yellow, and of course white. Many had frills and lacey edging, some had little bows and flowery patterns, others were plainer. There were now as many girl's panties in my drawer as there were boy's underpants.
"Breakfast at 8 o'clock sharp!" Mum had said. "TWO well-behaved daughters this morning please!"
That was one of Mum's codes that today was to be a 'girly day' for me.
Mum popped her head round my bedroom door and passed me one of Cate's (or mine perhaps, by now) pretty cotton summer dresses to put on, very colourful, flowery and girlish and just above knee-length, with a slightly-flared skirt.
I slipped out of my, boy's, pyjamas and chose a pair of white, patterned panties for the day. The panties had little frills on the waistband and legs and a nice pattern of pink flowers with green stalks. They also had a tiny stain between the legs which washing hadn't got rid of. A little reminder that they had been my sister's.
I drew the panties gently up my pale legs, looking down as the elasticated legbands and distinctive girl-style gusset eased up my thighs towards my crotch. As the panties reached my groin I had to lean forward slightly and hold out the front of the panties so that they could envelop my boy's parts. Then I stretched them up over my bottom and all evidence of Robert Brown being a boy was securely snug within its girly cotton prison.
I had come to love the feeling of pulling panties over my little willy, enclosing it safely for the rest of the day. There was no front opening which it might escape through. It was hidden, and shrinking, as if it realized it had no important part to play.
Presently, arrayed for the day in my panties, my dress and my brown leather (girls') sandals, I arrived last in the kitchen for breakfast. My sister was finishing a piece of toast and raspberry jam. Cate was wearing a similar dress to mine, but in different colours.
"Mum, Bobbie's not wearing ribbons." declared my sister (who wasn't either).
"But Mum," I complained, "I'm a boy."
"Yes darling, of course you are, and a very sweet boy too. But we're going out shopping today. And since you're having a girly day today you don't want people to spot that you're a boy - do you?"
"We're going out, with me like this!" I replied.
"Yes, of course, darling. Why on earth not?" stated Mum with perfect common sense.
My hair wasn't as long as Cate's, but Mum fixed me up with a couple of little pink ribbons. She was right, I didn't want people to laugh at me because I was wearing a dress, so the more like a girl I looked the better. This was the big conundrum for me. I hated being dressed as a girl, but to avoid public humiliation I had to try to be as convincing a girl as possible!
"Panties check!" exclaimed Cate. She knew how to play the game now.
I knew what was coming if I didn't react obediently, a smack! So I delicately lifted up my dress to waist-height to show my mother and sister that I was indeed properly secure in pretty panties.
"Fine. Good girl." Said Mum.
I loved it when Mum showed approval like that. She was a good mother, even if she did like to dress me up as a girl. I knew she only did it because I was naughty and she wanted me to behave more like Cate.
She had found out that dressing me in Cate's clothes now and then was a good way to make me quieten down when I was obstreperous, which I often was. And she was right. It worked. I was terrified that any of my friends might find out and I knew that Mum wouldn't hesitate to use that weapon if she had to.
Mum had started by just making me wear one of Cate's dresses when she wanted to keep me quiet; but later she made me put on a skirt instead if that was more convenient, and even Cate's old shoes. One afternoon, when I accidentally broke one of her precious china ornaments while playing around, she decided she really needed to teach me a lesson. That was the day that she marched me upstairs to change for her, and reached into Cate's underwear drawer to thrust a pair of Cate's white and pink panties under my nose, saying, "Bobbie you will start with these!" Cate was watching smirking, at her bedroom door.
Mum began to assign Cate's used clothes to me more and more; starting with Cate's underwear, after Cate complained to her that she didn't like me wearing any of her "nicest stuff" and particularly her favourite panties.
I hated dressing like a girl, but part of me loved it.
The boy part of me thought girl's clothes were sissy and ridiculous - you weren't meant to get them dirty, you weren't meant to let anyone see your undies, you had to sit with your knees together... But another part of me loved the soft, comforting feeling of my sister's clothes, the calming feeling they exerted, the way my mother and sister treated me more kindly, more sympathetically, when I was dressed as one of them. I used to look at myself in the mirror and lift up my dress and look at my frilly panties, and say to myself,
