Crystal's StorySite


Girly Day

by 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,

"You are a very sweet, pretty girl Bobbie."

Which was the real Bobbie? I was beginning to doubt whether I was a real boy. Maybe I was a girl inside, but with boy's features, boy's parts on the outside. Maybe Mummy realized this and was trying to help me?

* * *

The shopping trip went fine. No one in the streets or the stores thought anything other than that my mother had two pretty, well-dressed daughters...

...Until when my sister and I both wanted to go to the bathroom. The nearest one comprised a public toilet block in the middle of an attractive little park which boasted a lawn, flowerbeds and trees. Of course, I had no intention of going into the Ladies part, but I suddenly remembered that I was wearing a dress! I would have to go into the Ladies side...wouldn't I?

No one seemed to be around...and I was still trying to decide what to do, when Cate piped up,

"Mum, I don't want Bobbie in the Ladies with me. He's a boy!"

Mum thought for a moment, and then told me I might as well slip into the Mens since no one was around.

"When you're both finished I'll meet you over at that store." said Mum, pointing at a general store about a hundred yards away across the grass.

Cate disappeared into the Ladies to go to the toilet in girly privacy and I cautiously stepped into the Mens. Thank God! There was definitely no one in there.

In the single cubicle, I pulled up my dress, pulled down my very pretty girly panties right to my ankles and sat down on the toilet seat. It was easier that way...

...I had had a messy accident once before - trying to pee standing up, panties round my knees, while holding my dress out of the way. Mum had been very angry because I had spoiled the dress and had behaved in an unladylike manner while in girl's clothes. She sent me to bed, in a long white nightdress, for the rest of that day.

...But...Oh no!...disaster...

...Boys' voices came to my ears, clearly moving this way. My heart missed several beats...

And then...their footsteps...coming into the least three of them!

...Well, I calculated to myself, problem, I would just sit and wait for them to go.

- - -

The boys carried on chatting, and I could hear them peeing at the urinal wall. But they didn't leave...

...Without warning, an aggressive teenage voice echoed, "Can you hurry up in there dude! I'm dying for a shit."

My entire body turned cold and tingly with fear. I felt weak all over, and could only stammer,

"Er, sure, I'll be as quick as I can."

Oh no! Why did I say that ?

But, what else could I do? He sounded tough and I was certainly not tough. And he was obviously older than me.

But I didn't move. I couldn't. I was frozen with fear.

I stayed rigidly seated on the toilet, delicate panties round my ankles, dress around my waist - afraid even to move in case a rustle of material gave away my secret.

"Come on kid. ...Or we'll pull you out of there!"

Then, a scraping of feet sounded outside the cubicle and...

...a face appeared underneath the door! Looking up at me...

The teenage boy's eyes caught my eyes for a moment...and were about to withdraw in embarrassment, thinking I was a girl, when he glimpsed my willy between my open legs...

"Hey guys! It's a boy kid in a girl's dress!...AND with frilly panties round his ankles. What's going on?!

"Come on kid, get out of there or I'll come in and shit all over you!"

His friends laughed.

My heart was pounding in my chest. I was even more terrified now. But I thought if I didn't move, they might force open the door or something...

I shouted, "OK ...uh...pardon me. ...I'm coming out right now. Don't come in, please."

I stood up, shaking like a leaf. I pulled up my panties, and pushed down my dress...and gingerly opened the door.

Three young thug types were staring at me, the boy in a girl's dress, in amazement.

"Hey frilly-panties, what are you doing in the Mens? Shouldn't you be in the Ladies?"

"Show us your little panties, panty-boy!"

I tried to get to the exit door, but they blocked the way. One of them reached out and pulled loose one of my hair ribbons.

"Oops! Your pretty ribbon has come undone!"

"Come on little boy. Lift up your dress and show us what you're covering up."

"Show us your little dicky, little girly. Have your nuts come down yet?"

"Has your Mumsie left you all alone? How sad!"

I was staring to cry and simultaneously to hyperventilate with panic now. I couldn't even feel my willy, which seemed to be trying to shrivel up and disappear inside my body.

"Come on kid. Show us what you've got if you want to get out of here."

"OK! OK! I'll do what you want if you just let me go!"

In surrender, I reached up underneath my dress, up to my waist and tugged my panties down to my knees. Then I lifted up my dress in humiliation for all to see my little scared willy, in all its hairless naked pink glory, projecting prissily from my groin.

I wanted the earth to swallow me up.

The boys just burst out laughing.

"Holy cow, it's SMALL, isn't it?" one of them announced.

"Tiny! About as big as a girl's clit." said another.

"No wonder his Mummy dresses him as a girl. She probably can't tell whether he's a boy!"

"Cute panties though! They would great on a real girl."

I just stared at them in whimpering horror, waiting for some sign in their eyes that they might let me go now...

"OK little girly. Run off and play now." said the first boy.

Desperate to escape this humiliation, I tried to simultaneously pull up my panties and walk past the boys to the door. But they weren't making it that easy...and all of a sudden I was tripped up and fell flat on my face on the dirty floor! With my panties still down and my dress still up! With my white, but rapidly blushing bottom, exposed to view by all. One of the boys leant down and slapped my bottom hard and loudly, sneering,

"Smacked botty for dirtying your pretty clothesies, little girl!"

His smack stung my bottom and made me gasp. I stumbled part-way to my feet, now with a grazed knee and with a red bottom, and sort of half-crawled, half-walked out through the exit door - my dress all over the place and crumpled up, my panties half-way up my thighs, my cheeks lined with tears.

But at least I was out now. I pulled my panties back up to my waist and tried to rearrange my dress more or less back into place, and ran as fast as I could towards the general store, sneers and insults being hurled after me across the park, for anyone within range to hear...

"We don't want to see you in the Mens again, girly-boy!"

"Go home and play with your dolls, you sissy!"

"Lift up your skirt and show everyone else your frilly panties and your tiny pee pee!"

I ran and ran, crying like a baby until finally I reached the store...and safety...

Mum was there. Cate was there. Half the town seemed to be in there! ...As I staggered in, looking like a very messy, miserable and tearful girl.

"Bobbie! Where on earth have you been? And why are your clothes such a mess?"

"M-Mummy, I had a little trouble...g-getting back...There were some rough boys toilets."


"Oh you poor poor little darling! Come to Mummy..."




I would enjoy corresponding with other people whether in my position or in my mother or sister's position. If you are interested please e-mail me at my above address. - Bobbie.




2003 by Bobbie838. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of StorySite and the copyright holder.