Reluctant Diva 5
Inspired by Lipstick Discipline
Chapter 5 – My big day
The day before Thanksgiving I was surprised to see my mother’s station wagon at the school gates at the end of the day. When she saw me she motioned me to get in the back of the car.
“Hurry Jennifer! We’ve a lot to do and not much time to do it in,” she greeted me as I pulled the door shut behind me. I was desperately hoping that no-one within earshot had heard her make use of my femme name!
“You can change as we drive” she instructed, pointing to the clothes laid out on the rear seat.
Of course I was already wearing my panty-girdle under my clothes so it was easy enough to remove my shirt and pants and put on the bra and dress laid out on the seat. I swapped my socks and trainers for sandals and by the time we pulled up in the parking lot, all that was left to do was fix Jennifer’s face and brush out her hair.
Mom’s air of mystery still prevailed, but I can’t say I was totally surprised when we drew up in front of the hair salon she patronised. The name blazoned across the shop front read Belle Boutique. I regarded it with dread. I’d been there on two former occasions, the most recent being to prepare for a fancy dress day at school to have my hair styled. For that event my mom had dressed me up and had gone way over the top, resulting in my complete humiliation. All my objections had been to no avail then, but with the recent improvement in our relationship I had a small glimmer of hope that this time her ideas for me would be less extreme.
When we walked in the door it was immediately obvious that the stylist, Delia, was expecting us. She complimented me on how much cuter I had grown in the weeks since she’d last seen me, but this friendly welcome was accompanied by the sliest of smiles. I grinned back nervously. It was evident that Mom had already laid down what she wanted to be done so I just had to sit in the chair and hope her plans weren’t too way out. Though my hair was beginning to grow again, it was still quite short and I took some comfort in thinking there wasn’t much scope for anything too dramatic. Wrong again! On the counter before me were laid out a dozen or so flat lengths of hair. Each was about eight inches long and the colour was close to my own.
Delia laughed at my look of consternation. “Don’t worry, honey. These are extensions. They’re really good quality, too. Human hair! You’re going to look so pretty.”
Thus ‘reassured’, I resigned myself to go with the flow. In reality I had little choice so I made myself sit still in mute terror while she began the styling process. She started off by trimming the extensions to length, holding each up to a different part of my head and then snipping, or not, as required. That done, she selected a section of my own hair with her comb and pinned it up gluing the corresponding piece in place. This process was repeated until just about all the extensions had been employed. Once the glue was set she brushed it all out and, lo and behold, I had a head of nearly shoulder length hair.
The next step entailed wetting it and then forming a centre parting. With the front combed forward she next trimmed across at the level of my eyes. She laughed merrily at my worried look. “Once the curling is done your bangs will hang above those gorgeous eyes of yours. We wouldn’t want to hide them, now, would we?"
When ‘my’ hair was trimmed to Delia’s satisfaction, it received a shampoo while she chattered away non-stop. That process was only to be expected but I was further alarmed to be told that she was adding some tint. This was to achieve an all-over match apparently and also add some ‘natural’ highlights. She finally wound my locks on rollers, which were secured tightly against my scalp with bobby pins. A pungent smelling setting lotion was applied and the drier was lowered over the whole. Its roar effectively drowned out any conversation though in any case I was feeling too stunned to attempt to make any.
While my hair was setting, attention was paid to my nails. They were washed and soaked, and then had false nails glued in place. Once fixed, these were coated with layers of shocking pink polish and lacquer so that they seemed to glitter like fairy lights. Delia removed my sandals so that my toenails could benefit from the same treatment, with cotton balls separating the toes while the polish dried. When I looked down I realised that super sexy was the signal I was broadcasting, literally from head to toe. This couldn’t be happening!
Delia then turned her attention to my eyes. “I’m shaping your brows to look a little more defined,” she explained. Thankfully, the result wasn’t the extreme fine arch that I immediately envisaged and dreaded but merely a taper to the side and an angle near the centre. To my alarm, however, several trios of false eyelashes, three lashes in each, were next glued onto my upper eyelid and trimmed to length. She crimped them in a curler and with an application of mascara, my eyes seemed rounder and larger than ever in the mirror.
Eventually the drier had done its work and the hood was removed. I waited to see the finished results with trepidation. Beaming with satisfaction, Delia took out the rollers, brushed out my curls and preened the bangs on my forehead. When she turned the mirror for me to see, my appearance was certainly dramatic. Where was the boy who had walked out of school a couple of hours before? No trace of him was left that I could find, and neither of that ‘girl’ that I often saw there these days. There was only the reflection of a glamorous young woman in her place. Her hair and complexion looked flawless and her eyes seemed huge, like deep wells of mystery. The effect was intimidating and I was sure that I would not be able to carry off the part which my parent had assigned to me. Clutching at straws, I took refuge in one small plus point. It was a huge relief to know that under all of this, Robert Cartwright would be completely unrecognisable!

“That… that can’t be me!” I stammered
“Like what you see?” Delia smirked proudly. “Told you that you were going to be pretty! You’re not just pretty, honey, you’re hot!” Like that made me feel any better!
Mom was chatting to the manageress and to a tall elegant woman who seemed to be in charge of the salon. I’d noticed the latter watching me intently, almost hungrily, while I was being worked on. Delia’s next remark was addressed to my parent, “He… No… She’ll need a hairnet in bed tonight to keep the curl in place. Then a gentle brushing in the morning and she’ll be good to go. Big day tomorrow, sweetie. You’re going to knock ’em dead! Have yourself a blast!”
Both the other women came over to scrutinise the results of the employee’s handiwork, before turning to each other with a satisfied smile and nodding approvingly. Predictably Mom was pleased as well and the outcome of her own examination clearly proved favourable. “You’re just amazing Delia. Here!” handing her some bills. “Worth every cent!”
I gathered that this payment must have included a handsome tip. My stylist beamed with gratitude. This must be costing my mother a packet, I mused ruefully. Was trying to make me resemble some kind of sex symbol really worth it, whatever the result? As we walked to the car I even plucked up the courage to ask “How are you affording all this, Mom?”
“Just think of it as an investment, Jennifer” she replied airily, then more significantly, “and if you do exactly as I say…. Well I’m hoping for a fast return!” More mystery!
One final preparation was called for which I should have been expecting but wasn’t. It occurred just before bedtime. I had already undressed and was about to slip on my nightwear when Mom appeared at the door of my room. “Before you get ready for bed, there’s something we need to do”, she informed me.
Wildly embarrassed I stood there in my birthday suit, holding the nightgown against me to preserve some modesty but unsure which part of me to cover, the swollen mounds on my chest or my private area. My mom seemed blissfully unaware of my discomfort and showed me what was in her hand. She was holding her Remington lady shaver which she proceeded to connect to the socket, telling me that she was going to remove the fuzz from my legs, arms and underarms which would be essential the next day. I didn’t really have any hair there to speak of but by the time she was finished, and she had anointed the areas so treated with copious amounts of lotion, all my skin was satin smooth.
The next day was Thanksgiving and I was awakened by my mother entering my bedroom and gently shaking me. As it was usually my job to get up first and get the breakfast ready, I started up guiltily in alarm. Then I saw the clock and realised there was still another hour before my normal time.
“It’s okay, sweetie.” Her voice was gentle and her face wore a concerned expression I hadn’t seen there too often. However I could sense an undercurrent of excitement in her too.
“No chores for you this morning” she continued. “I want you looking your best. Here’s your coffee. Now, when you’ve drunk it you need to bathe.” Her parting shot, “Oh and wear a shower cap when you are in the bathtub. We don’t want steam from the tub ruining that hair-do.”
Slightly bemused, I sat up and sipped my coffee. This was better. I could get used to being pampered like this! Ten minutes later I was on my way to the bathroom. Mom was there to check my head was properly covered. “That’s fine! Now don’t be too long. And make sure you douche beforehand!”
Ah yes! The douche! Something I should explain perhaps. I had met this item of torment (and fascination) nearly a year ago. One day I had got in from school to find my mother returned from work early with one of her sick headaches. I realise now it would have been that “time of the month” for her. Tom was out playing with friends and I was already changed into a day-dress I particularly hated and was starting on my chores when I was called into my mother’s room. I was surprised to find her laid on the bed in her nightgown, a damp cloth on her head. She asked me to go to the store for her and pick up a prescription and a whole list of things.
Though I daren’t refuse, in those days I was unused to go out by myself when dressed as ‘Jennifer’. Also I was wearing that hideous dress. I couldn’t face being seen in it and was desperate to think up an effective excuse so as not to go. I looked at my mom laying feebly on the bed and an idea came to me that seemed worth a try. I complained that I too was feeling bad and probably had got what she had got! Big mistake!
At first she was naturally inclined to ridicule the idea of a boy having period pains but then her manner softened and she actually seemed to go along with my story. Feigning concern, she put her hand on my forehead, and then on my belly while I moaned and played along. It was working! There was absolutely no way I would have to leave the house in that stupid dress! The shopping would have to wait until Tom came home. Maybe he could run Mom’s errand for her. However I ought not to have bargained on getting the better of an experienced nurse. Although she gave as her diagnosis the probability that it must be my time of the month too, there was a glint in her eye which should have been a warning to me!
Still seemingly sympathetic, she explained all the ins and outs of teenage girls’ periods and the sort of things they need to do to themselves ‘down there’ each month as a result. It was way too much information! Then I received my just desserts. As a remedy for my pretended pains she introduced me to the rigours of the douche. This device was formed of a kind of pink rubber bulb, on the end of which was a strange-looking nozzle, long and fluted and with all sorts of holes in it, like some sort of water sprinkler. She filled the bulb with warm soapy water. Then I nearly died of embarrassment when I learned how this thing of nightmares should be applied (making allowances for my anatomical differences of course!). Embarrassment, yes totally, but I also I was surprised to find that there was a surprising up-side too. Shall we say it was mind-blowing, a whole educational experience?! After a thorough internal cleansing and a follow-up bubble bath, I was pronounced to be “sparkling clean, inside and out”. Then I had to go to the store anyway.
Mom laid down that the next five days would form the extent of my ‘period’ and in that time each month I would be expected to adhere to a regime of douching regularly each day.

Worse, I had to wear a tampon for the days of my ‘period’, a further humiliation. At the same time I became experienced in the use of sanitary pads. Can you believe it?! Aaargh!!
That was how this particular aspect of my feminisation had begun. By the time Thanksgiving had come around it didn’t strike me as out of the ordinary to be reminded to douche on my way to the bathroom. It was okay. After my session and a soak in the warm scented tub I felt serenely relaxed about what the rest of the day might hold for me. That feeling wasn’t to last, as you might guess. With my bathrobe wrapped around me I made my leisurely way back to my bedroom to find my mom standing there. She was already dressed in one of her best outfits and awaiting me impatiently. On my bedside table I noticed she had set a breakfast tray. The contents were quite minimal, just fruit and a little cereal, but she laid stress on the importance of keeping my figure in trim. She motioned me to sit and eat and told me it would save time if she busied herself with my hair while I did. Once she had fluffed out my locks and arranged them to her satisfaction, all I now needed was to get myself dressed for the day ahead. At last the mystery of what costume had been lined up for me was finally to be revealed.
“Now pay attention, Jennifer” she began. These days the instruction would have sounded ludicrously like the introduction to a briefing by Q, but the James Bond films had yet to be screened back then and in any case my mood would soon have sobered up when the details of what Mom had been planning were unfolded. Perforce I listened carefully enough to suit the demands of my exacting parent.
“As you know, today our town has its Thanksgiving parade” she went on. “There are two floats which are for entrants to the beauty pageant.” My face fell as I guessed what might be coming next. “Yes, my girl, I have entered as you as one of the contestants. Isn’t that going to be so exciting?”
Totally shocked and horrified, I could only gape in reply.
Apparently heedless of my mental turmoil she went on brightly “In the parade itself the girls are to be dressed in keeping with a theme from American culture. That part of the programme starts at noon, by the way. Then after that there’s the bathing beauty section and for the grand finale the girls’ attire will be evening or cocktail dresses. That’s when the results of the contest will be declared.”
I gazed at her wide-eyed. “Err… Mom…!” I was going to object but that’s when a sickening realisation hit me. So much for my intentions to go beyond my mother’s schemes! There was never ever going to be the chance of accomplishing that. All I would ever be able do to please her would be to go along with whatever crazy idea she came up with next.
“Now this may surprise you, but in my estimation you stand a really good chance of making the final” she continued, seemingly blissfully ignorant of the panic that was rising inside me. “You are only fourteen but could easily pass for seventeen or eighteen, and have got everything going for you….. your face, hair, legs and your figure too. Trust me, it will be worth it. There’s a first prize of $250 with a guaranteed entry into this year’s state-wide beauty contest. Second prize is $150 and third is $100. See why I’m hoping that you will try your hardest!” She took my hands and looked into my eyes with an excited smile. She reminded me of an eager child. “Well! What do you say?”
“Er… well… er… okay… I guess.” I was horrified but she was being so nice to me I didn’t see a way to say no (or, never in a million years!) without triggering a major falling out, especially as I knew she had laid out quite a sum of money in paying for all those preparations. Though it was quite a novelty for me not to find myself being bullied into doing something so totally against my wishes, I was discovering that being cajoled into complying could be quite as effective as a means of manipulation. Basically I just couldn’t face letting her down! Once I’d reluctantly acquiesced, concerns over the finer details of her scheme came to the fore in my head.
“So… what will I be wearing?” I enquired tentatively. A little curiosity might, I felt, be justifiable!
Mom glanced at my face as if to reassure herself that I was fully on-board. “Well, you already know what you will wear for the final, that beautiful new dress from Sears. For the bathing beauty display I bought you a really stunning swimsuit in the summer sale. It’s by the Hollywood designer Cole of California and will really turn some heads.” Conveniently overlooking the fact that turning heads came near the bottom of my list of priorities, she pushed on to the pièce de résistance.
“For the parade itself you need to wear something more than just eye-catching. It has to celebrate the heritage of our community. Well, we used to be tobacco growers round here and we still grow some in certain parts of this state, so your costume will be that of a Cigar Girl. Get it? Back in the thirties, nightclubs and speakeasies always featured pretty young women, dressed to please, with trays of cigars. Your costume is in pink. You’ll just love it!”
In my mind’s eye I could conjure up the image of just such a costume. It wouldn’t have been my first choice but sounded as if it might be something I could just about go along with.

Mom looked delighted over my acceptance of all this. If she was a little surprised, she hid it quite well, but I felt sure that she was expecting to have to use one of her more draconian methods of persuasion to get her way. Without any objections from me, however, she was like an irresistible force and became instantly practical.
“Firstly Jennifer, we need to think about dealing with your bottom end. Now, as you have decided (Really? I have decided?!) to put yourself on public display in a cute little costume, then nothing but nothing must show. One of your short panty-girdles will work but we also need to get rid of the least little bulge down there. It’s called tucking. Let me demonstrate.”
She took off my bathrobe and knelt down in front of me, level with my privates. In her hand was a roll of surgical tape. To say that I found this position embarrassing is a wild understatement and I coloured to the roots of my hair and wanted to die! Undeterred she reached forward and first fastened a piece of tape across-ways. She next attached two more pieces of tape to pull everything back between my legs and secured them. The result was that all vestiges of my maleness completely disappeared upwards and backwards. She handed me my panty-girdle which I stepped into, pulled up my legs and eased over everything. When I looked down below, I was totally smooth and secure without any hint of a tell-tale bulge.

Mom had me turn around and walk up and down in front of her. Once her critical gaze was satisfied, she gave me the roll of tape to keep in my purse, “in case I needed to use the bathroom later”. I was allowed to slip my robe back on while she sat me at the vanity and spent the next hour working on my make-up. Besides the usual cosmetic routine, my eyebrows were more sharply defined in pencil, my extended lashes were crimped, curled and mascara applied, and my cheeks were delicately rouged. Finally she used a fine brush to give a pretty outline to my lips before filling them in. The shade of the lipstick matched my nails exactly. She handed me the tube so I could freshen my mouth whenever it might be necessary.
Time was flying by and after checking her watch Mom told me to make haste. She reached down what was to be my costume from where it was hanging in the closet and handed it to me. Seeing the garment for the first time, I examined it curiously. It was in a soft silky pink material and short, but bore little other resemblance to the cigar girl image that my mind had conjured up. There were garter tabs attached for one thing, six of them. The top and bottom hems were trimmed with lace, so that it bore more of a resemblance to lingerie than the dress which I’d been imagining. The bodice was boned and strapless and I could see that I wouldn’t need to wear a bra underneath.
In for a penny! I sighed and stepped into the skimpy thing and pulled it up as high as I could. It was tight and unsurprisingly revealing so that generous amounts of my ‘bust’ were left on view. To go with it were a pair of fully-fashioned nude stockings and for my feet, a pair of pink high-heeled sandals. Resignedly I slipped the rest of the ensemble on and went to stand before the mirror to see how the complete thing looked.

The image before me was breath-taking! Oh boy, would I get noticed in this! To my mind it screamed one thing. SEX! Dismayed, I stood there and racked my brains as to how I might avoid going out attired so. The thought that I would be on public view was totally scary and my brain had frozen. No escape route came to mind. I didn’t dare refuse. From bitter experience I knew that if ever I went back on anything I’d said I would do, my mom would go ballistic, deeming me to have proven myself a liar. She was now gazing at me, beaming all across her face at the sight that met her eyes and I hadn’t either the heart or the courage to raise any objection. She took hold of my shoulders and looked me up and down approvingly. Far from being concerned over its total lack of modesty she seemed absolutely delighted with the outfit. “Jennifer! You are going to knock them absolutely dead!”
I was (and am) puzzled by her attitude. Surely, if I had really been her daughter, her reaction would have been something more along the lines of “You’re not leaving this house dressed like that!”
Mom was ready herself, looking very smart in an elegant two-piece. She fastened my fairy locket round my neck and sprayed some perfume on me. Treating me like some exotic piece of porcelain, she made sure I was wrapped in a warm scarf before she helped me into my coat. She checked my purse so I had everything I might need and then picked up the dress-holder which contained my other two outfits. Allowing me to carry nothing but my purse, she shepherded me outside and held the rear door of the car for me. Tom was already ensconced up front wearing an expressive grin that I longed to wipe off his cheeky face. We dropped him off at Miles’s house on the way to the theatre where the parade was due to start. He was going to come downtown later to watch the festival with his friends.
On the seat beside me was the cigar girl’s tray complete with a pink satin ribbon to go around my neck. Sitting in all my state in the back while my mother drove me felt kinda special, like I was a celebrity, but when we pulled into the parking lot, my nerves were jangling. Was this really happening? In a daze I allowed my mom to escort me to a side door and we walked down a seemingly endless corridor to the green room reserved for the contestants.
Once ushered inside I could see that there were about half of the other participants already there. The room wasn’t any too warm and some girls were sitting in their outside coats but I could see some of the costumes; a couple of cowgirl outfits, an Eskimo, Snow White and another princess of some kind in the line for registration. We tailed on to the end and after a wait of ten minutes or so reached the desk. A middle-aged gent with slicked-back hair and a small black moustache gave me what was supposed to be a winning smile and introduced himself.
“Hello, my dear! I’m Percy Gardner, the host for today’s event. This is my wife, Janet.” He gestured toward the buxom woman by his side. She had dyed blond hair and a lot of jewellery and looked coldly at me. “And your name?”
“Her name is Jennifer Cartwright. I’m her mother.”
“Ah yes, Mrs Cartwright, Jennifer. Welcome, my dear.” His hair was jet black, not wholly naturally, and his eyes flickered over my face while his wife checked the list of contestants.
“Yes, Cartwright. Here we are. Number 16.”
“Sweet sixteen, eh!” Another oily smile. “You can leave your daughter in our hands, Mrs Cartwright, and make your way to City Hall where the parade will finish. If you’d like to take your daughter’s things…”
Mom helped me out of my coat and enveloped me in a huge hug. “Good luck, sweetie!” She handed me my cigar girl tray and stifling a little sob, turned and ran from the room. She was clearly emotional and it took me a moment to get over the realisation that I must mean a lot to her, after all. When I turned back Mr Gardner was leering at me, holding out the label with my entry number, 16, to me. His eyes, instead of flickering up and down my face, were now alternating between my ‘boobs’ and the top of my legs. Well, I guess, there was plenty exposed for him to see! His wife’s expression froze further.
“Let me help you with this.” My hands were holding the tray, which was surprisingly heavy, so I hadn’t taken the label with my number on it from him. He deftly peeled the adhesive sticker from its backing paper and turning me around placed it firmly onto the costume. He actually located it on my right buttock! When he gave my butt a little rub, doubtless to make sure the adhesive had stuck securely, his hand lingered there for noticeably longer than was necessary. Completely taken aback by this intimacy I just stood and let it happen. What worried me most was that it felt sort of nice, to be touched like that. How was that?! Ewk! He turned me back to face him, one of his hands ‘accidentally’ brushing across my bust as he did so!
“Just wait over there, dear!” his wife intervened. Whilst the forced smile remained fixed on her face, her eyes glared at him.
As directed I went over to the door where the other girls were lined up. Even more of a variety of costumes were now visible. The young woman next to me was a few years older than me and was dressed as a mermaid. With her swim top and fishtail skirt her costume was almost as revealing as mine.
She grinned as I joined her. “I can see you’ve made a hit with Pervy Percy! You have to be quick to escape those hands, dearie!”
I grinned back ruefully. While we waited I took note of the contents of my tray. Mom had gone to town! Across the front was the logo Tobacco is King with the name and colours of our state. Arrayed on it were boxes and boxes of candy cigarettes and matches, chocolate cigarettes and bubble gum cigars of several varieties. I offered one to my neighbour but she declined, laughing. “Nice try! This outfit is tight enough on me!” She was right!

Just then Janet came over and started to marshal us out to the floats. It took some time and there didn’t seem to be a lot of rationale for deciding who got posed where. I was placed on a velour-covered hay bale near the back of the second float. I was partially hidden by one of the drapes and that suited me fine. We were about to start off when I heard someone exclaim “No! No! No!” It was the host, Percy, who had come fussing over to do a final check. I was astonished when I saw he was referring to me.
“The colours, woman! The colours!” he blazed to his wife. He came over and taking my arm pulled me from the orange drape of the bale I was seated on. I had to agree that my shocking pink ensemble rather clashed with it. He made ‘Snow White’ change places with me so that I ended up on the highest perch in the centre of the float. The next few minutes were spent in getting my limbs arranged to his satisfaction, which seemed to necessitate his hands gripping my butt and thighs and my bare shoulders quite a bit, while Janet looked daggers at him all the while. When ‘perfection’ had been finally achieved I could truthfully say I knew just what being manhandled entailed! With a final admonition to us all from his wife “Now smile and wave girls!” the cavalcade set off.