Reluctant Diva
Inspired by Lipstick Discipline

Chapter 1 – A new persona
It was after attending the Friday night ball-game at the high school stadium that my life really changed. That date marked the end of an ongoing battle between Mom and myself. I had been ‘persuaded’ to go there wearing a dress, and a hairpiece too. Can you imagine?! Actually I have to admit I’d have been wearing a dress even if we hadn’t gone to the game and I’d picked out this one myself. The hairpiece was my mother’s idea, though. But I’m getting ahead of myself. How, in the late 1950s, did a red-blooded, all-American boy, in his freshman high-school year, ever find himself in dresses in the first place?
Wearing female attire had started so long before that I could hardly remember when. Even before my father had left us Mom had often tried to persuade me into dressing as a girl. Crazy! Perhaps she just wanted to explore what it would be like having a daughter. Anyway, each Hallowe’en I would be cajoled and pressured into becoming some female character. Her machinations had varying degrees of success. She sometimes got her way and there were a number of photographs in the family album which testified to those occasions, but in general I resisted. Especially as I got older. After my parents divorced, there were plenty of times when I experienced the same kind of persuading, but for a totally different reason.
As I got older, I guess I got more and more unruly and with Dad no longer around, my mom was probably about at the end of her rope trying to cope with my bad behaviour. When I was twelve or so I was caught out badly. She found some goods I had shop-lifted from the five-and-dime store. As a result of my light-fingered action I was sent to school next day wearing bright red nail polish. She believed in making the punishment fit the crime, you see! On another occasion I ended up attending class wearing pink lipstick for lying about completing my homework and it went downhill from there. Each time I had, or was deemed to have, misbehaved, the more draconian and humiliating my punishments became, until eventually it became quite the norm for me to change into girl’s clothes after school. While so dressed I was made to undertake a list of household chores that seemed endless. Just as if I really were a girl!
This punishment regime progressed as time went by. By alternate persuasion and threats I was eventually made to wear feminine undergarments under my outer clothes every day, school or no school. How could that happen?! Well, the next year I’d been caught in something all teenage boys go through. Mom had found my stash of girlie pictures! The fact that it was pretty tame by today’s standards – underwear commercials from teen magazines – didn’t save me from any of my mother’s anger. To say that her reaction was extreme is an understatement. After being labelled a pervert and soundly punished, I’d been hauled off to the lingerie department of the big store downtown and a whole collection of girl’s underwear was purchased for me, along with some dresses, girl’s shoes and other stuff. I now possessed a full range of those very items which clothed the lissom female bodies I’d found so fascinating in those magazines.
You will have noticed that the punishment was made to fit the crime once again. Mom picked on my interest in girls in underwear in this instance. It marked the start of a daily discipline every day consisting of dressing after school as my alter ego ‘Jennifer’, my mom’s femme name for me. All day at weekends! Worse, as a means of restricting access to my private area I was made to wear one of those long-legged panty girdles twenty-four seven.

Yes, that included all of the night-time, and at school as well under my boy clothes. Even though I was allowed to take a note to school excusing me from gym classes and sport, I remained paranoid that my guilty secret would be discovered. If found out there was no way I would ever live it down. How could I face any of my friends? With my regular absences from sports, they were fast diminishing in any case.
The by-product of being coerced like this was that I became expert at wearing heels, applying makeup, painting my nails and arranging my hair. I could have given lessons on the sort of deportment expected from a teenage girl in those days. My boyish pursuits were gradually traded one by one for girlish ones. I was further indoctrinated by being made to read teen magazines and chick-lit type novels and to watch a diet of soap operas and soppy romances on TV. My mother went as far as checking on me afterwards to make sure I had been paying attention.
Occasional rewards for good behaviour were also linked to my regime and I was introduced to the ‘delights’ of girlie times with Mom. Typical were days when, daintily dressed as a teenage miss, I would accompany my mom to the library, the museum, the art gallery, a cinema or a restaurant. Though I was petrified I’d be discovered, with my long hair (for a boy) and delicate features, it actually proved easy enough to keep my true gender a secret on such trips. We made the perfect ‘mother-daughter’ couple. Worse, to my consternation I even found myself beginning to enjoy the deception I was practising on bystanders. I had to admit that some of what I experienced was actually kinda nice. It felt like heaven to be pampered and cosseted like a tender flower in stark contrast to the stern treatment which was my usual lot.
The worst part of this regime was the accompanying mind games which Mom played on me. At each new departure and despite all my efforts to resist, the rationale for what took place somehow became twisted. I was tricked into acknowledging that it had been “my idea” to play with my lipsticks, and “my choice” over which girlie outfit I had ended up in. In reality the choice had been influenced by intimidation, accusations of lying, direct threats or the narrowing of an ever-shrinking set of options. There emerged a sort of pattern. First, an agreement that behaving this way wasn’t all that bad would be enticed from me. Well, I found the feel of feminine clothing very sensual and the knowledge that I was fooling most of the folks who saw me was quite amusing, so in honesty I had to agree that some of it was kind of fun. The next thing I knew, this admission was used in evidence that I wanted to be wearing dresses and makeup and behaving like a girl, whereas... I hated it!
If I then tried to justify how I actually felt I was then accused of being a liar which led to extra sanctions, usually painful ones. As time went on I was treated more and more as if I really were a girl. Instead of Robert, I had to answer to the name ‘Jennifer’. Whichever way I turned my manipulating parent had an unanswerable argument that it was my perverse choice to become a shameless sissy interested only in fashions, makeup and chasing boys! Yes! Boys!!

It wasn’t like that! No way! The worst thing was, I could never prove her wrong!
Despite every attempt at resistance I could come up with, I gradually saw my boyhood interests replaced one after another. Action men and comics were discarded. Going to baseball practice was actively discouraged, and if any of my buddies called for me I usually hid. Dressed the way I was for most of the time, the last thing I needed was my former friends catching sight of me. After the occasion when I was sent to junior high school in lipstick, most of my classmates had taken to avoiding me and that suited me just fine! The ultimate humiliation came when I was kicked off the baseball team. Thank God my dad wasn’t around then to witness the event. In fact he wasn’t around much at all, as Mom was only too pleased to remind both my little brother, Tom, and me at every opportunity.
For long enough, it was a welcome escape from Mom’s feminising discipline to pretend to myself that Dad still thought of me as a second baseman, his macho boy and his ‘li’l buddy’. However, that didn’t last! During a disastrous stay with him and Marnie, his second wife, the illusion had finally all unravelled and the last mental refuge for my masculinity disappeared.
It was quite recent. Since the split, there had been minimal contact with my father. Though visits with him and trips out had been arranged, more often than not they had been cut short, cancelled or postponed, to my intense disappointment. It didn’t help that Mom was vocal in expressing her disgust on these occasions over what she saw as further evidence of his unreliability and selfishness. In the past I had always revelled in trips to the ballgame, and camping and fishing expeditions with him. This latest visit of mine had been the first in as long as I could remember. It seemed to be a dream come true when I knew that I was going to spend some quality time with him; for nearly a week on this occasion. I was destined to be free of my enforced femininity at last. I thought I had died and gone to heaven; and then my mom ensured that it all went sour.
I’d always dreaded Dad’s reaction if he ever got a hint about my other-self, but at the end of the visit, the deadly secret finally come out into the open. Despite Mom hating Marnie with a vengeance, she made an unholy alliance against me with her. By packing some of my girlie things along with my boy stuff for my step-mom to find, she contrived to reveal that I spent time in female underwear and the existence of ‘Jennifer’ became impossible to hide. It wasn’t long before Marnie had wheedled the full facts out of me. Disaster! On the last day of my stay, my dad was called in to his office and it was then my stepmom saw her opportunity to humiliate me. Using the threat of full disclosure she manoeuvred me into a little harmless ‘experimenting’ and I found I was given little choice but to try on a variety of her own outfits. She then did exactly as she pleased with me, which even involved taking me on a trip to the mall, and later for drinks at a posh restaurant. This last was the scariest situation I had yet found myself in. To cap it all it was then that Dad showed up.
Marnie didn’t have to say a thing. My father was witness the spectacle that ‘Jennifer’ made, dressed for an evening out. By that stage I was more than a little tipsy. Along with full makeup and painted nails and wearing one of his second wife’s party frocks, my hair was even adorned with a little ‘fall’ or hairpiece! Being discovered like that was my worst nightmare come true. His too, probably, judging by the way his disappointment in me showed. As expected I experienced the full force of his anger and disgust. For months afterwards I felt sick to my stomach whenever I thought about how that unmasking and shaming had taken place.
Once back home I did attempt a last-ditch rebellion against Mom’s regime. With my hair cut short at Dad’s instigation (he’d always hated my long hair), and in my boy clothes, I plainly but politely told her I wasn’t going to be ‘Jennifer’ any more. This vain attempt to resist her and redeem my masculinity was short-lived. It was stamped on immediately and I found myself utterly defeated. As a consequence the realisation followed that I had no choice but to give in to her wishes completely. There was no alternative left that I could see. I had no place else to go and my future prospects were unutterably bleak. Worst of all, there was no way of restoring myself in Dad’s estimation. He was the one person whose good opinion I had really cared about. Well, that had gone for ever, or so I figured. Once the reality of this had sunk into my mind, it didn’t seem to matter much what anyone else might think.
So, the night of that ball-game marked the end of my resistance to my mother’s schemes. We spent the evening together as mother and daughter in outwardly perfect accord. Acceding to all her wishes wasn’t easy, but I did get an immediate reward by doing so with apparent good will. Her unqualified approval was something I had rarely known up until then. The contrast between how each of my parents viewed me in my ‘Jennifer’ persona couldn’t have been more marked. I began to see that the relationship between my mother and me might even begin to blossom in a new way.
In the following days I took some time to think my confusing situation through. I was now convinced that the only way to please my mother was by dressing and acting like a teenage girl. I couldn’t work out the reason why. The only thing I could come up with was that perhaps she really did miss the daughter she never had. It was easy enough to please her on a single occasion, but I found that to remain in her good books was something else. Every time I managed to satisfy her in one respect, then the bar was immediately raised and I had to try even harder.
What, I wondered, if I anticipated the next scary ordeal she might have in store for me and came up with some crazy scheme which was all my own. Instead of waiting to be cajoled and bullied all of the time, I could look for new ways to be as feminine as I could. Desperate as this course of action appeared, there was little left to lose. Any pretensions I had to masculinity had already disappeared pretty much completely, so why try and hold on to them?
There were other motivations working on me. The amount of fun I got making all and sundry believe I was a teenage girl was an unexpected source of enjoyment. It gave me mixed feelings even though on balance I would have preferred to be thought of as a real boy. Lastly, in the back of my mind lurked another faint hope. Against all the odds, Mom might have a change of heart and relent if she could see where her plans for me were leading. I still couldn’t really believe that she wanted to turn me into a full-time girl!
So with all these conflicting thoughts going round in my poor confused brain, I finally decided to try and find some way of topping Mom’s feminizing plans for me? That would really take some doing, but if it succeeded it would be worth it. I also had a sneaky suspicion that I might actually enjoy the attempt.
I came downstairs one Saturday morning knowing what I would do. I’d already bathed and dressed and fixed my make-up as was now my normal routine. It being the weekend, I was clad in my day-dress over panty-girdle, hose, bra, and heels. All was topped by a frilly apron. I checked myself in the mirror and wondered with a sigh where that second-baseman had gone. There was no going back, it seemed. I resigned myself to another day and got on with my girlish chores, as they were deemed back then. I had the coffee percolating, the eggs boiling and the toast browning for breakfast and had just started putting the laundry from the previous day in to soak, when Mom entered the kitchen.
“Breakfast’s ready” I said with what I hoped was a winning smile, “Come and sit down. The newspaper’s just here. I’ll call Tom, shall I?” My brother was two years younger than me and unlike me it seemed he could do no wrong in her eyes.
My thoughtfulness was rewarded, at least in part. “Looking after your poor old Mom, at last!” she smirked. “It’s almost like having a real daughter!” In passing I received a brief hug and a peck on the cheek, followed by a pinch on my other cheek, down below.
“Oww! Mom!” was my involuntary response, wincing. What hurt more than the pain was being reminded that my attempts at true girlhood were only regarded as fake after all.
“Don’t be a baby.” she scolded. “That cute little tush fills out the skirt of that dress so nicely, you are going to get it noticed, one way or another.” To my relief, I could see that she wasn’t trying to be mean. Her words were accompanied by a gleam of humour in her eyes.
After more than a year, the continual wearing of my tight undergarments had been having a shrinking effect on my waist which was only too predictable. The displaced body fat just had to go somewhere and my rear and thighs were the beneficiaries. I had become increasingly self-conscious about the size and shape of my butt, which became all the more noticeable as my waist grew ever smaller. Teenage boys just didn’t have such curvy figures and I didn’t enjoy Mom teasing me about it on this particular morning.
Her manner became serious. “Are you taking those ‘vitamins’ I got you?” she asked, for no apparent reason. “Every day?” she persisted.
I couldn’t follow where these questions were leading but her eyes had narrowed; always the warning sign of an impending storm!
“Yes Mom,” I answered truthfully, “Two every day. Just like you told me”.
I’d been taking some mysterious salmon coloured pills daily since just before my fourteenth birthday, nearly six months ago. Back about that time I had noticed a sort of chubbiness in the area of my chest. Needless to say, this was a horribly embarrassing development for any teenage boy, let alone one in my situation. Mom had put it down to my hormones when I finally plucked up the courage to ask her about it, and she maintained that my apparent boobs would naturally diminish as I grew older. Far from growing out of it however, the mounds on my chest seemed to get bigger and bigger and the little pills didn’t seem to help at all. The bras I had originally been made to wear as a discipline began to fit me all too well and by this time I was the owner of a bustline which many teenage girls of my age might be proud of.
In my innocence, I didn’t understand why Mom looked disproportionately pleased with my reply on this present occasion. Casually picking up her paper, she remarked, “Good. I think you might increase your dosage from now on, okay? Try taking three a day. A growing girl needs to have her hormones balanced just right.”

There was clearly some significance behind these instructions despite her assumed nonchalance but I didn’t understand her purpose then, so I just smiled “No problem. I’ll have enough to last me till the end of next month.”
When my brother Tom eventually made his appearance, Mom and I had done with breakfast, and I was about to clear our things from the table. He hadn’t spent any time in front of the mirror, as far as I could tell, and his t-shirt had a few marks down the front. You could see by their appearance that he had been eating chocolate ice-cream. Mom scowled at him from behind her paper, the warning furrows between her eye-brows ominously returning.
Her take on his laxity was typically biased and as usual the censure when it came was directed against me. “Jennifer, why is Tom wearing yesterday’s t-shirt?” she asked severely. I gulped anxiously. This rebuke wasn’t fair, of course, but defending myself wouldn’t be helping the success of my new resolution any. It always seemed as if Tom managed to get away with far worse behaviour than what I had ever been allowed. I had some faint hopes that that was about to change, at least.
“Oh gosh, Mom. That should be in the wash. Sorry! I must have missed it when I picked up” I stammered. “Come on, Tom, let’s go and find you a fresh one in your drawer.”
He looked mutinous.
“I know your favourite one is clean” I encouraged him.
Thankfully, he didn’t rebel against my coaxing this time but stumped out. I looked back and whispered conspiratorially “I’ll make sure he washes his face and hands too!”
Mom’s frown softened. “That’s more like it, my girl. I expect you to care for your little brother, you know”.
The situation safely defused for the moment, Mom returned to her paper. With much exercise of patience on my part, Tom was persuaded to wash and change and brush his hair.
On returning I started to clear away the breakfast things, while wondering when the best opening would come to start putting what I’d planned into effect. Mom seemed relaxed enough, drinking her coffee. So here goes! I slipped back to the table and sat in the chair next to her, as close as I could.
“Mo-om” I said, plaintively. “Can I ask a favour?” She looked up from the paper, a patient expression starting to spread across her face.
“It’s quite a big favour” I went on in my most winning tone. “You know the money Mrs Martin and Mrs Bennett have been paying me for helping them all this time. Well, I’ve spent hardly any of it, and when I was shopping for you last week, I had a look around Sears’ fashion department.” I had her full attention now.
“Well! I saw this dress!” Without even trying, I listened to myself starting to sound enthusiastic. Not so long ago I wouldn’t have believed that I’d be saying these things, but yes, it was really me, the red-blooded all-American freshman high-school boy!
Tom, sitting on the opposite side of the table, gaped at me. Ignoring him, I ploughed on. “You have given me some lovely dresses, I know, but this one is different. It’s a little bit longer and so much more grown up, like some that the senior girls would wear. The skirt is really full and the material is dreamy, soft and white with glossy spots. Oh, Mom, it would be heavenly to wear!” A good proportion of Jennifer’s wardrobe consisted of hand-me-downs so this approach ought to sound convincing.
Mom didn’t say anything but was looking at me with an odd expression. She probably couldn’t believe her ears. Tom, meanwhile, was choking with suppressed laughter.
She must suspect that I’m up to something. I ploughed on regardless. “I haven’t got enough cash to buy it outright, of course”. I hesitated before finally gulping out, “but if you would loan me the rest, I’d pay you back as soon as ever I could…” my voice trailed off and I sat waiting for her reply with eyes cast demurely downwards.
“Hmm. Well.” She temporised. “It sounds expensive. I’d have to see it.”
She thought some more then softened a little, “When would you wear it?”
“Well” I said, in for a penny, “it would have to be for a special occasion and I can’t think of one, but we might make our own occasion. You have some really stylish cocktail dresses which you never get to wear and you have such a great figure”. Still off-balance, she smiled at the compliment, despite herself. Perhaps this might be going better than I had dared hope. “I was wondering if we could hold a little party. There’s Thanksgiving… or New Year’s Eve… You have lots of friends that would come. It might be fun……”
“Well!” Mom exclaimed, laughing, “My ‘daughter’ is full of surprises this morning!”
She gave me a little squeeze. “What brought this on, honey?” Her arm was still around my shoulder and she clasped my hands with her free one. It was a relief to see how pleased she looked and enjoying her proximity gave rise to a delicious feeling of warmth. Together with an awareness of her perfume, I was even dismayed to feel a tingling down below. I knew that sensation only too well and it increased my confusion.
I blushed deeply and muttered lamely “Oh just seeing the dress, you know. I would so love it.”
At this Tom exploded with mirth. “What a priss!” he mocked.
“That’s enough from you, Thomas Cartwright”, Mom snapped back at him.
He stopped short, stunned to be the one on the receiving end of her displeasure for a change. I tried not to show any sign of satisfaction at his discomfiture. He got up from the table and stamped up to his room.
“You know, Jennifer, that boy needs taking in hand.” said Mom thoughtfully, but her attention quickly returned to me. “If we are going to look at dresses we had better change” she determined “and you need to fix your hair”.