Reluctant Diva 3
Inspired by Lipstick Discipline
Chapter 3 – My little ‘sister’
The very next day was Sunday, and wet. The rain wasn’t letting up and looked as if it was on all day. The problem with that was that Mom had agreed to let Tom have Miles and another of his friends, Andy, over to play. That didn’t suit me at all. It was bad enough to put up with Tom’s repertoire of mocking looks and snide remarks about my feminine attire without having any of his friends there. Their presence was likely to egg my little brother on to open ridicule while Mom would look on wearing her amused expression, or would make ‘helpful’ comments like “Now you’re getting a taste of what we women have to put up with from the opposite sex”.
If it were wet, they would be cooped up inside and the prospect for me was a whole day of torment to which I wouldn’t dare to retaliate. This would surely put my newfound resolve to exceed my mother’s feminising schemes to the test.
The morning started reasonably well for me, as the trio were allowed up to Tom’s room to swap comic books and play with model soldiers. Though we didn’t often get to church Mom liked Sundays to be different, so chores had to be completed the day before or left till Monday. Mom and I had time to ourselves, reading some of her magazines and talking about our upcoming party. I was wearing a Sunday outfit which included a flimsier and prettier dress than the ones I wore for doing my chores.
After an hour or so Mom told me to make sandwiches and drinks for lunch. “You can take the ‘boys’ theirs” she remarked, a glint in her eye. Her emphasis made me wince at my implied exclusion from that group but obediently I loaded a tray and carried it upstairs. Taking a deep breath I opened the door of Tom’s room and clopped across to his desk in my heels to put down the tray.

There was an ominous silence.
“Lunch, boys!” I trilled with a brave smile “and there will be a piece of cake for you when you are done with these.”
At this Tom rolled his eyes at his friends derisively as they grabbed the drinks. “It’s just my fairy brother” he sneered and continued, showing off before his buddies, “Let’s have the cake now, sissy boy! We don’t want sandwiches and I don’t take orders from a big girl’s blouse like you”.
His friends stared at him, then at me.
“Why are you wearing a dress?” said Andy. Then scornfully, “You must be a faggot or something!”
“Yeah!” Miles joined in.
“Faggot, faggot, faggot!” they chanted in unison.
Clenching my fists under this hail of ridicule, I was reminded not to retaliate by my long painted nails digging into the palms of my hands. I knew only too well that I was expected to behave like a ‘lady’ even under this sort of provocation.
“Oh what a shame, I see you’re not hungry, Thomas.” I said finally. “Shall I ask Mom if you can have something different?”
My loaded question, and the use of his full name, got through to Tom for the moment, and he pulled a face and fell silent. His friends were in no way overawed, however, and continued to make fun of me, flouncing about the room in effeminate poses and putting on a high pitched imitation of my voice. Incidentally, for some reason that was yet to break, providing another source of embarrassment for me among my peers.
Deciding I could safely ignore them I slipped out of the room and left them to it. Hunger would probably make them eat what was set out for them eventually, I reasoned. I knew enough not to mention any of this to Mom, relying on no sympathy from that quarter and sure enough, on my return she sat sipping her lunchtime coffee and pretending to hide that irritating smile of hers.
After half an hour had passed things started to get noisy upstairs again. After letting it go for what seemed like an age, “Go see what they’re up to, Jennifer” said Mom, frowning.
Reluctantly, I got to my feet and marched back upstairs. Tom’s door was open and I stopped short on the landing. I could see the three of them parading around the room, arms held limply out in what they thought were girlie poses. I was horrified to see that they had put on a variety of garments which I recognised as some of the contents of the laundry basket. Andy and Miles each wore a bra over their t-shirts and Tom was wearing one of my blouses, on his head! I froze as I realised that, while the bra Miles had on was mine, the one Andy was wearing was clearly not.
“What in heaven do you think you are doing?!” cried an angry voice from behind me.
Mom had come silently up the stairs and was surveying the three miscreants with blazing eyes.
“That’s mine! How dare you?!” she yelled, as she took the offending undergarment from Andy, none too gently. I backed into a corner to get out of the way.
“Don’t you have any respect for other people’s things?” she thundered. “Wait till I tell your mothers how you behave when you’re visiting. Out! Now!” Turning to Tom “I’ll deal with you later” she snarled as she marched them downstairs and out towards the car.
He looked at me with fear in the back of his eyes. I couldn’t help but feel a little sympathy for him (although only a little) plus some trepidation on my own account. Tom was usually allowed to get away with any amount of bad behaviour, but this time “I think you may have crossed the line” I said.
“Oh, she’ll get over it” he scoffed, but the words sounded hollow and didn’t convince either of us.
The scene when Mom returned was one I would dearly like to forget. She still looked mad when she entered the house. Tom had retreated to his room but was commanded in short order “Thomas, get down here!”
“Mom, I’m sorry, we didn’t mean…” he started but next instant she had bent him over her knee, the hair brush in her hand.
“Never, ever, go near, my underwear, again!” she yelled, punctuating her words with well-aimed blows. Tom yelled and squirmed and finally wriggled from her grasp, defiant.
“What’s the matter with you? We weren’t doing any harm” he shouted at her.
I squeezed up into a corner, knowing the kind of explosion this response would just have triggered in Mom, and fearing that somehow I would get blamed too. The next ten minutes seemed unbearable and ended finally with Tom being sent to bed alternately sobbing and muttering incoherently about running away.
Mom was shaking when it was all over and stood at the kitchen sink staring mutely out of the window. The rain poured steadily down and every prospect seemed brooding and sullen. I watched her anxiously for a while. After a bit, she seemed to have calmed down and when I looked closely I could see a tear rolling unchecked down her cheek. She looked vulnerable and a little frail.
Without stopping to think how risky such an action might be, I found myself crossing the room and coming up behind her to slip my arms gently round her waist. She didn’t attempt to stop me, so I just nestled my head into the hollow of her back and held her.
After a few minutes she sort of sighed “What kind of mother must I be?”
I just squeezed her a little tighter and we stood there looking out into the rainy, darkening afternoon.
Eventually she turned round and enveloped me in a warm hug. “Honey! That was awful sweet of you”, she crooned. “So you do love your poor old Mom, even when she gets a little cross?”
I didn’t answer. She pulled my head down to nestle against her breasts and I felt some more tears splash down on my cheek. It was kinda special, being that close. She took my hands in hers and stood back looking at me and smiling. “Who’d have thought it?” she mused. “Just when I needed a woman’s sympathy. Jennifer, Jennifer!”
“I’ll make us some coffee?” was all I could think to say. She nodded assent.
By the time it had percolated and we were sitting at the table, Mom was more herself again. “What am I going to do with that brother of yours?!” she exclaimed, and seemed actually to be expecting me to supply the answer.
I didn’t know what to say, but came out with “I guess it might be easier, if I had a little sister!”
We both laughed. “Too right!” agreed Mom with feeling. “But I don’t think I’ve the energy to go through all that again, this time with Tom.”
I stared at her as I realised that my remark had conveyed a shade of meaning to her that I hadn’t intended.
“I wonder how you would manage, though? A teenage girl should get as much practice as she can making younger ones behave.” She was thinking out loud. “You will be sorely needing it when you have a husband making demands on you while you are bringing up your own family”.
“Mom, please!” I protested feebly. What was she thinking?!
She brushed aside my objection. “Okay, let’s see! This is how it’s going to be. Over the next month Tom’s behaviour is going to show a marked improvement, or he’s going to find himself in dresses. How you achieve either outcome is entirely up to you. You can use any ‘inducement’ you think might be effective, but keep your hands to yourself. I won’t have any bullying, got it?”
“But how….?” I interjected, but was cut short.
“That’s not my problem, Jennifer. There’s a lot more to being a woman than wearing pretty dresses and flirting with the boys. If you are really wanting to impress me then let’s see how you are as a big sister. I will give you this one hint: it’s best not to meet every problem head on, okay?”
“I think so” I hesitated. I hadn’t a clue as to what she meant!
“If you can make a success of this little project,” she thought for a second, “then I won’t make you pay for that dress, or for anything else you might need soon. I’ve a few other purchases in mind. Thanksgiving’s not far away and I’ve some great ideas for your costume then”, she grinned. Costume?! “And another thing; you won’t be going to Mrs Martin’s quite so much if you are looking after Tom, so you’ll find you have to watch your pennies in any case.”
She looked decided. “How about it? Deal?”
“Deal!” I said, with outward complacency while internally I was anxiously wondering what those “other purchases” might entail. I knew I could expect Mom to find some way of pushing the boat out much further than I was prepared to go and dressing me up for Thanksgiving might give her a perfect excuse. While I felt sure I could carry off the majority of female outfits, I didn’t have the same confidence about one of Mom’s ‘costumes’.
I was able to deal with this little qualm fairly well by remembering my decision of the day before. I needed to push the envelope continually if I was to keep my parent on side. Back in the present, what was demanding my attention more urgently was how, exactly, I planned to bring Tom into line. After a moment more of thought, I got up and headed purposefully for the door.
“I think I’ll go sort through my clothes,” I said. “There’s quite a few that are too small for me now. I somehow feel sure they might come in useful! Thomas may be in for a little surprise!”
“Good girl!” Mom’s laugh had a meaning ring to it. “This could be fun to watch!”
The next day dawned bright and sunny and the air felt fresh after yesterday’s rain. As it was a Monday I was up extra early to pick up and start the laundry before fixing everyone’s breakfast. I had Mom’s uniform and shoes laid out ready for her so she wouldn’t need to rush. After such a full-on weekend, it felt odd to be wearing a boy’s shirt and trousers even if they were on top of my obligatory panty-girdle. I nearly forgot to rearrange my hair so I would look like Robert once again at school.
Tom was strangely quiet at the table. He was keeping a low profile and needed no second telling to get himself ready. He was out the door in plenty of time for his bus. My own school bus ran later than his by about ten minutes, which just gave me time to head back upstairs and rearrange some clothes in various drawers, before I too left the house. Mom evidently guessed what I had been up to because I received a conspiratorial wink from her as I left. It was good to know she and I were in sync just at present.
Tom’s day ended earlier than mine so the arrangement was that he would stay at a neighbour’s house in the next block until I called to collect him on my way home. Today was no different and he seemed his normal cheeky self as we walked along. The events of the weekend seemed to be forgotten. As soon as we got home, Tom kicked off his shoes, went to the kitchen to get himself his usual juice and biscuit and plonked himself down on the sofa in front of the TV. I went upstairs and changed into my girl clothes then fixed my face and hair. I came down and entering the lounge, walked across the room and turned the television off.
As my brother started to protest I cut him short “Before you get stuck into TV, Thomas” I said gravely, “There’s something you need to consider. Mom is still seriously displeased with the way you and your friends behaved yesterday and you are likely to get punished further”.
“Oh, come on, Rob! This is too much” he whined, but I had gotten his attention.
“You’ve got to realise that a woman’s underwear is personal to her. If you mess with it, it shows you don’t respect her, so you need to change Mom’s mind and show her that you do.”
“We were just having fun!” he moaned.
“Yes I know you thought that, but if your fun is at someone else’s expense then it stops being ‘just’ anything.” I explained.
“We didn’t even know that the stupid bra was hers” he mumbled.
“Hers or mine, it’s still the same thing” I enlightened him, improvising wildly. “Now here’s what you can do. Mom was inclined to say, no TV for a week.”
“A week!” He gaped.
“Well it would certainly make you remember all right, but I think that’s a bit harsh, so there is another way. What if you were able to show Mom you wanted to see for yourself how it felt to be female? That would show you think women are important.”
Tom looked doubtful at this and thought for a minute before asking, “So what would I have to do?”
“Okay, this is how you can get out of a more serious punishment. You can try wearing a bra yourself for a few hours. That would show you were really sorry.”
Tom looked horrified. “I’m not dressing up like you do, with makeup and everything. I’m not a fa…”
“Thomas!” I cut him short “That’s no way to talk. You’ll end up in worse trouble, that way.”
I went on patiently “No-one is asking you to dress “like I do”. It’s just a token gesture. If you were to do this after school till bedtime, I’m sure that would be the end of it.”
He looked at me sullenly.
“Ok then” I continued, assuming silence meant assent, “In your top drawer upstairs you’ll find three of my old training bras. They’re all clean, so why don’t you go and choose one to wear before Mom gets home. If you are quick you won’t miss the start of the Lone Ranger. I’ve put in some tops as well that no longer fit me, for you to wear over whichever bra you decide on. You won’t even be able to see it.”
I smiled encouragingly. “You had better wash your face and hands first”.
He sat for a full five minutes thinking, a frown all across his face. Finally he got up and went upstairs without a word. I could hear him open his top drawer and indulged myself by imagining the creeping horror that must be filling his little mind. This was sweet! It would repay him for some of those jibes and scornful looks I’d been forced to put up with, from my own little brother.
After a while I called up the stairs “How are you getting on?” There was no answer so I went up to his room.
He was knelt on the floor in just his shorts and socks with one of the bras twisted across his chest. “I can’t get this thing fastened” he complained.
Suppressing a grin, I took it off him and showed him which was the right way up, where the arms went and how to line up the hooks and eyes to fasten at the back. He needed the tightest of the three settings. I adjusted the straps till it was nicely in place.
“There, that’s how it should be” I said, and promptly undid it and took it off him again.
“Now you do it” I said. “Mom will be impressed if you can manage one all by yourself.” It took three more attempts before he finally did it without help from me. “That’s great” I encouraged “now choose a top to go over it”.
He looked in his drawer and then back at me aghast. “Do I have to?”
I considered for a moment then “No, but then you will be showing your bra for anyone to see. Or you could just do without TV.”
He went back reluctantly and selected one at random and put it over his head. I straightened it for him. Oh joy! It was the pink crop top with the kitten gambolling on the front, which I had hated being forced to wear so much. It seemed so long ago now.

The light padding on the bra made the front stand out a little and the fit was just about right. Just then I heard Mom come in. Perfect timing! “That looks good on you. Let’s go and say hello to Mom and see what she says?” I smiled reassuringly.
Mom was sitting at the kitchen table changing her shoes when we got down. She looked up and gazed at Tom appraisingly. “Tell me Jennifer, why is Thomas dressed like that?” she demanded coldly, still staring at him critically.
“Oh Mom,” I started, “he is really sorry about how he behaved yesterday. To show you he wasn’t meaning any disrespect, he wants to know what it’s really like to be a girl. He picked out these things himself…” My voice trailed off as her face showed no signs of softening.
“And you think a girl would want to be seen like this?” addressing Tom this time. She grabbed his hand roughly “Look at your grubby fingernails. And! Those! Knees!” slapping his legs. “Get upstairs and into the bathtub and quick about it!”
“You said this would be okay” yelled Tom to me and stormed off defiantly.
“Not a great start, Jennifer” said Mom quietly after he had gone. “You forgot that the basics are the most important. Ah, well. Better try again tomorrow – it’s another day.”