Reluctant Diva 7
Inspired by Lipstick Discipline
Chapter 7 – Changes
In one of the history lessons at school I remembered reading about some ancient Greek guy who had to perform one feat of endurance after another to atone for doing some pretty bad stuff. It seemed I was fated to follow the same path, though I beg to point out that the stuff I might have done and was certainly paying for was no way in the same league as his.
The following Saturday evening I was midway through prepping the vegetables for supper when I heard Mom on the phone in the hallway. Listening intently, I could overhear only the odd phrase or two, but even that was enough to fill me with dread.
“…been dying to go out with you again…. It’s been ages, Karen.” This was followed by a lot of clandestine discussion that I couldn’t make out, accompanied by much sly merriment. Call me paranoid, but it sounded ominous. Before Mom made her reappearance, the call ended with “Don’t worry! I’ll make sure ‘she’ is there. Bye!” There was heavy emphasis on the pronoun.
She made her announcement straight away. “Now you will be pleased to learn that I’ve arranged a nice treat for you with your little girlfriend. I’ve noticed how you’ve been neglecting each other. It’ll be tomorrow night. She’s really excited over how well you did in the pageant and is just dying to hear first-hand how it all went.”
I stared in disbelief. The source of more pain than pleasure, this was one relationship I had been trying to play down for some time. Karen Morris had been a sort of girlfriend, but I had soon realised that in between her dates with me, she had been seeing at least one of the jocks from the junior football team and I had given up trying to compete. Well, almost. She could be quite hard to resist when she chose to be nice. A single glance from her puppy-dog eyes always made me melt.
“Now don’t thank me!” was Mom’s parting shot as she left me to my chores.
It had been at the fancy dress day at school that Karen and I had first got together. Although it was strange to start a relationship when she was dressed as a boy and I as a girl, we’d had a lot of fun that day, one way and another. Being taller than me and confident with it, she had actually saved me from being picked on by a couple of school bullies, Lee Rafferty and his black sidekick, Abe. For me that was a definite highlight in our relationship and afterwards I always felt I owed her, which was something she had taken full advantage of. In the weeks that followed, when I had been crazy about her, it turned out that the only time she was interested in me was when I was being 'Jennifer'. Dressed as she invariably was in pants and t-shirt and wearing her hair cut short, we made a perfect couple. I guess it could have been viewed as an ideal boy-girl relationship. Except that I never got to be the boy!
At first I was so desperate to go out with her that I reluctantly agreed to dress the way she wished me to. We would go to the coffee bar where most kids of our age liked to meet. Sunday evenings were best because others might be at church service with their parents or doing last minute homework. There were few customers and we could always find empty booths which were ideal for making out. A plus for me was that the scarcity of patrons reduced the chance I'd be seen by someone who knew me. All the same, I found it completely nerve-wracking, and that seemed only to add to Karen’s enjoyment! After the first couple of such evenings it was understandable that my ardour had cooled considerably.
I couldn’t understand why Karen was now wanting to revive our relationship. It was puzzling. The next question I had to face was what to wear. When I had delivered that parcel of hand-me downs to Mrs Morris, she had responded in kind, not wanting to be outdone in curtesy. I hadn’t had any curiosity about what had been sent over, but Mom took a different view, as I discovered when she told me that it was time to get ready.
“Everything you will need is laid out on the bed for you. I’ve picked you out a pretty dress and top that were Karen’s. You will definitely be in her good books if she sees you are wearing them.”
Any new way of endearing myself to my fickle paramour was welcome and I found my mom’s logic convincing enough, though there was an amused glint in her eye which should have given me pause. I hesitated but was given no time to consider. “They may need a little pressing so you had better jump to it.”

Obediently I went upstairs and found a pink cotton tea-dress on my bed with a matching bolero jacket. The pairing was crumpled and looked fairly ordinary. When I’d ironed them there was a real transformation, which put me in a good mood. I found ironing satisfying and I have to say my standards were very high, which was no doubt due to the amount of practice I got. Even so, with its circle skirt and attached paper nylon petticoats, pressing this extremely bouffant dress took me forever. It was adorned with a dainty white collar and little puff sleeves. I smiled to myself as I worked, supposing that it would please my date if I were to be wearing something so pretty.

On the bed were some other items I hadn’t worn before. As a gift to celebrate my success in the pageant, my mother had bought me some expensive lingerie “for evening wear”. Gee, thanks Mom! I examined it again curiously. There were a pair of tap pants and a matching garter belt and bra. They were in a white silky material and were so flimsy they might have been made of cobwebs. My Mary-Jane heels were arrayed by the vanity on which were a pair of pink hair ribbons and a roll of surgical tape. There were no doubts in my mind as to the purpose for which the latter was intended.

Doubtless my mom had her own reasons for choosing this ensemble but it seemed as always that the best option was to play along. She knew best, I guess. When I slipped into them, the floaty tap pants felt like… well… just nothing. Similarly I was also conscious of the way the thin silky bra caressed my budding ‘breasts’. It made me feel fragile and defenceless and the sensuous nature of that feeling surprised me. There was also relief not to have to wear my restricting girdle but without its accustomed security down below it was reassuring to know that I had everything safely taped away.

I finished dressing and checked myself in the mirror. The garter belt cinched my waist in tightly and the dress fitted closely in that area too. The combination of the two made the full layers of skirts flare, standing out dramatically from my hips which looked larger in consequence. I gave a twirl in front of the glass. The material of the dress flowed beautifully as I moved. It was a lovely sensation and my head was full of happy thoughts as I sat to work on my make-up. When I clopped down the stairs to show her my outfit, my parent voiced her unqualified approval “Pretty, pretty girl!”

I handed her the hair ribbons to tie in for me. With my extensions still in place she had plenty of options as to how my hair could be arranged. As ever, Mom seemed to find putting the finishing touches to my attire fascinating. When finally satisfied “There that’s better, now, isn’t it!” she crooned dotingly, sliding her arm around my waist. Times like these between us were special.

However, I was given no time to dwell in the moment but was hurried straight out to the station wagon. From where Mom set me down I had to walk the last few blocks to the coffee bar, serving to heighten my sense of vulnerability on this occasion. My ever-present fear was of being recognised. Fortunately dusk was falling early now the season was so advanced and I could keep to the pools of darkness between the street lamps. Disconcertingly, there seemed to be more people around than I had hoped to encounter. The skirts of my dress were calf-length and extremely full. I’d expected that the shape would serve to conceal the way my hips moved as I walked in my heels. This hope was completely unfounded, however, even when I tried walking slowly. The dress’s skirt swayed uncontrollably with each step I took, accentuating the motion. That was bound to attract attention and the rustling of its paper nylon petticoats made matters worse. To my fevered imagination every head seemed to be turned in my direction. Embarrassing!

Though I was a few minutes late, Karen was even later. Standing outside the coffee bar I attracted stares from other customers who went in ahead of me. It slowly began to dawn on me that I was more than a fraction overdressed for this downbeat type of venue. T-shirt and jeans would have been nicely inconspicuous. The realisation hit me that though Mom must have been fully aware of the incongruity of my outfit, she had persisted in choosing it. Why would she want to subject me to public curiosity like that?

After what seemed like hours but in reality can’t have been more than a few minutes, my date appeared. Karen was dressed in loose pants, casual jacket and a white t-shirt and with her short hair and absence of makeup she looked very much like a boy. Of course when you looked closer, her pretty features, full lips and wide eyes gave her away. She greeted me with the broadest of smiles and assured me how cute I looked. Attempting to return her compliment I stammered that she looked good too.

She gave a smirk, “I’m glad you are getting some use out of that old thing. I only ever wore it once… to a fancy dress ball! But you’re such a pretty boy you can get away with anything! Tonight you can be my little princess!” she giggled at my discomfiture.

I was consoled a little when my date next slipped a protective arm around me and drew me close. She was now trying her hardest to be nice, telling me again how she liked having such a pretty girlfriend. She was taller than me even with my heels so when she pulled me to her and kissed me on the mouth I had to reach up to her. It made me feel even more like the girl in our relationship.

Once inside the café, Karen sat me down in an empty booth right at the back. Mercifully, it was dimly lit in that corner. Relaxing a little, I took off my jacket and smoothed the folds of my dress while she fetched us our drinks, my favourite hot chocolate and her black coffee. She put some coins in the jukebox then sat down next to me. It was starting to look like the evening might go better than I had originally hoped. We seemed to be getting on really well. This was so nice! She wanted to hear all about the Thanksgiving parade. She let me know that she and Mom had put their heads together to plan my cigar girl costume. It was clear she wanted to bask a little in the reflected glory of my success, while I was somewhat piqued that she had been involved in putting me through that ordeal. I let it pass however.

After a while the conversation turned to how long it had been since we had been out together.
“So much has happened. I gather that I have a rival for Jennifer’s affections these days?” she grinned mischievously.

I wasn’t sure who she was referring to, but in my haste to reassure her I found myself bursting out with, “If you mean Dennis, he’s just a friend, only Mom likes to make a thing of it.” I coloured as I said this, hoping my mother had not revealed any other ‘rival’ when they had put their heads together on one of those long phone conversations, someone that I actually had some feelings for.

My denial did me little good. She laughed archly “Jennifer, you’re such a little fibber! Yes, that weirdo Dennis, and it wasn’t your mom, I have other sources!”

Oh no, Sandra must have revealed all! I tried again to pass it off, unsuccessfully. “He’s just a friend!”

“Liar! I’ll bet you were all over each other. No making out then? ”

“No… Course not… We may have kissed.” Why did I blurt that out? Her eyes narrowed, in a manner worryingly like my mother’s.

“I knew it! You can’t stay away from the boys, can you? Horny little sissy!”

Ah yes, Dennis and Sandra! I need to clarify. Well, Dennis was just a friend from the sophomore year at high school and we did some stuff together. That’s about it really. Well… There was a bit more to it than that. Actually a lot more! Okay, here’s what happened.
That fancy dress day when I attended school in girl’s clothes was the start of a number of things. Besides signalling Karen’s interest in me and mine in her, something else got started, though inadvertently. I was noticed, and in particular, the expertise with which I handled my girlish attire got noticed. Someone spotted that here was a boy who was unusually au-fait with lipstick, mascara and walking in heels. Now who would notice a thing like that? That’s right; another boy who had similar experience!
A few days later, I was joined at table one lunch break by a sophomore who introduced himself as Dennis. I remembered him as one of the boys who had cross-dressed on the fancy dress day. In doing so he had looked very authentic but had seemed extremely shy. Smaller than me, he was of slender build, had dark hair and a lot of freckles. As we ate lunch, he was full of questions about how I’d managed to be dressed with such attention to detail. I tried to pass this off as one of my mom’s little games but he was persistent and couldn’t believe that my transformation was all down to my manipulating parent. It turned out that he was a self-confessed sissy and I couldn’t shake his assumption that I was “just like him”.
Apparently he was fascinated by anything and everything female and in his case it was entirely from choice! He lived with his aunt and Sandra, the younger of his two sisters, who I knew to be in her freshman year like me. He was allowed to dress whichever way he pleased and at home, as I was to learn, that was mainly as his alter ego ‘Denise’!
Over the next few weeks we spent a bit of time at school together. I was pretty much starved of friendship just then, especially with another guy, even if he was rather a strange one. He invariably wanted to turn our conversation to subjects like make-up, dresses and lingerie instead of talking about action men or football. Also he was demonstrably affectionate towards me, embarrassingly so at times. However, at least I had a buddy and that meant a lot to me, lonely as I was. Mom seemed to approve of our friendship and even allowed me to go over to his house one Friday evening. I’d had to use the pretext that he was helping me with my math and she was more than happy with that. My grades certainly were in dire need of some extra tuition and it was his best subject. At the time I was surprised she allowed me to go but, in retrospect, perhaps she knew a little more about Dennis and his propensities than I did. I often wondered what was exchanged in all the time she spent on the phone with Karen and later I tumbled to it that she was privy to all the school gossip.
It was on my visit there that events took a turn that I hadn’t anticipated. Dennis’s aunt was out so he and Sandra were alone in the house with his elder sister being away at college. They had the run of her room including access to her party dresses, underwear, make-up, heels, you name it! It was mind-blowing! I was inured to the trappings of femininity by this time but the full extent of my new friend’s cross-dressing activities shook me. That and his feelings for me which were totally unexpected. And unwelcome!
The term ‘gay’ had other meanings back then but its present usage would now aptly describe both Dennis and, as it later turned out, his sister Sandra too. It was the first time I had encountered anyone who openly owned up to such ‘tendencies’ and I had to suppress my instinctive recoil from such things so as not to offend either of them. This was the 1950s, remember.
The visit progressed from initial embarrassment to total humiliation. First-off the siblings wheedled me into showing them my skills with make-up. They seemed genuinely awestruck by my expertise. I was flattered by their praise and this led to my performing a full makeover on myself and then on Dennis. It was child’s play and I began feeling pretty proud of myself. To complete the look we tried on some of their sister’s outfits. It was quite a laugh seeing their amazement at the transformation achieved. When Sandra slipped out of the room, ostensibly to get us drinks, next thing I knew her brother had grabbed my hands and pulling me to him was kissing me full on the lips.

Completely taken aback, I simply froze and stood there waiting for him to stop. Well… he didn’t. The kiss went on and on. I remember thinking that the sensation was quite different to anything I’d experienced before. I found myself kinda liking it, strangely, and when he eventually pulled back I didn’t know how to react. My ‘friend’ on the other hand knew exactly what he wanted and repeated the experiment, this time with tongues! Eugh Yuk! Yes, but I have to admit thinking it was nice too!
Then I was startled by a bright flash. No! It wasn’t one of the effects of kissing a boy upon my confused senses! Out of the corner of my eye I could see Sandra in the doorway holding a camera. She had a greedy expression on her face, and was taking picture after picture. The subject matter was me apparently making out with her brother. Aaargh! No way! That changed the group dynamic somewhat and for the rest of the evening I was forced to do whatever they wanted under the threat of those photos being circulated around the whole of our school. I’d like to forget the rest. Suffice it to say we explored to the fullest the contents their big sister’s wardrobe, trying look after look on me, and him. In the midst of this prolonged makeover session their aunt returned. She didn’t seem to mind but could it get more humiliating? Well, yes, actually!
Unimaginably, in the middle of it all, Mom turned up to check on me. As a result she was able to confirm with her own eyes that I had a ‘boyfriend’. I would never be allowed to forget this fact and was more completely in her power than ever!

Back to my present date with my so-called true-love; “Please Karen, don’t be mean. I only want to be with you, but I never get the chance.” I could feel the tears welling up in my eyes.

“Well, don’t get upset, sissy boy! I just haven’t had any time since I started dating Louis.” She had a gleam in her eye as she let fall the name of the quarterback I’d seen her with. Trying to avoid showing my disappointment, I listened in horror while she went on to extol his chiselled features, huge shoulders, strong hands and how tall and manly he was.
“He really makes me feel like a woman, you know” she confided, and unwillingly I heard about the effect he had on her when they kissed. His other endowments were also alluded to in some detail, much to my chagrin. This was way too much information!
“But I hear you know all about that kind of thing now” she continued slyly. “You and that Dennis!”
I tried to look as if I didn't know what she meant but without success. “Come on now, don’t act so innocent! We both know what you really like!”
As if to illustrate her meaning, Karen pulled me to her roughly and started to kiss me full on the mouth. That was okay and at first I gladly surrendered to her. While her lips fiercely made play, her tongue darted in and out wickedly, leaving me gasping for breath. She began running her hands over my ‘bust’ which was only protected by the layers of flimsy material. It was fortunate that our corner was in the shadows. Her mouth was clamped over mine and her fingers squeezed my poor boobs, tweaking my nipples and not gently. I could make no sound in protest. I had never been as strong as her, and now less so than ever, it seemed. I squirmed in attempted revolt, all the while conscious of a sensation down below which felt intensely pleasurable. Oh no! That was something I really didn’t need! As if she read my mind, she leaned back and sweeping her hand up my skirt, began to explore. I gasped in a mixture of horror and ecstasy.
“Aagh! Karen! Nooo!” I whispered, but to no avail. Those silky panties offered no protection and I found myself moaning from the conflicting emotions I was experiencing.

“That’s right, little girl! You want it, don’t you?” she murmured in my ear. Trying to resist her, I squeezed my legs tightly together but with an evil glint in her eye she continued, leaning back to watch the effect it was having on me.
In response to her manipulations, I was close to losing control but summoning the last remnants of strength I could muster I took hold of her hands and pushed them away. It was a struggle but once free, I lay back in the booth and feebly covered myself up. It seemed a miracle that we hadn’t attracted the attention of the other occupants of the coffee bar, but the merciful darkness and the loud music must have kept us from notice. Karen just sat there pretending smugly that nothing had happened that could have caused me any distress.
“This is interesting! Now we know what you’re really like, we can have some proper fun.” Her laugh was just nasty. “I must get you on a date with one of Louis’s buddies. Or perhaps with Louis” she tittered. “Who knows? It might be more fun if we swap! He’s quite something, I can tell you. Wouldn’t you like…?”
What she whispered in my ear made me freeze. Dully I found myself wondering “How might that feel? It would…” Then I realised what she had actually said!! Ewk! No! That was so disgusting!
Hating myself for being so weak, I made a supreme effort to halt the train of thought she had started. I fervently wished I had never set eyes on my erstwhile heart-throb whose taunting looks were so painful to me. To gain some respite from her goading, I told her I needed the restroom and pushed past her. Once alone I sorted out my dress and my makeup in an attempt to regain something like composure. I was strangely relieved to find that my flimsy underwear had withstood her probing fingers surprisingly well and was undamaged. As if that mattered! The rest of the evening passed interminably slowly. There was an uncomfortable hour I somehow got through before Mom’s station wagon drew up to collect me again. On the way back home I made a firm resolve that I’d never go on another date with her. Never again!
At school the following day there came a further humiliation. You can guess my horror when I saw Karen and Sandra sitting together during lunch and the latter staring at me mockingly while Karen smirked in that evil way she had. I almost dropped my lunch tray when I realized what they must have been discussing. Talk about an unholy alliance. Wasn’t there anyone on my side? The remainder of the week passed without things getting any better. When it ended I was faced with something even more worrying. It was all to do with the impact of my new medication. The effects of my new ‘regime’ as Mom called it, hadn’t been felt immediately, but when they kicked in they were drastic. The first thing that I noticed occurred when I had my first hot flash. It happened in the course of one of my part-time jobs. As a maid!
“Isn’t it warm today?” I said to Rachel as I arrived at her house to do my chores on one particular afternoon, a few weeks after Thanksgiving. “Can I have a glass of water?”
She looked at me with immediate concern, kind as ever. “Are you feeling ill? You must leave that work for now”. She was training to be a nurse and my plight immediately brought her caring nature to the fore. She made me sit down on the sofa next to her. There was a worried expression on her lovely face and her big eyes were full of sympathy. Feeling quite sorry for myself, I could feel the tears welling up. Next thing I knew, I was enveloped in a hug and had the exquisite sensation of her large and shapely breasts pressed tightly against me. That did nothing to cool me down! On the contrary I felt warmer than ever, but it felt so nice all the same.
After a moment I returned the squeeze in kind. She pulled away and looked at me critically, smiling wryly “Hmm. Well I think you’ll live this time!” Slightly embarrassed, after sitting with her a few minutes more I said I ought to get on with my duties. I thought about the incident on the way back home and how much I liked cuddling up to Rachel. It was only then that I realised that in the days leading up to this I had been missing my usual physical reaction when I had let my thoughts dwell on girls and their bodies. The ‘normal’ pressure from my private area on my panty-girdle had been notably absent of late no matter what the stimuli. My body’s reaction on this occasion had only been triggered because she had squeezed herself up against me so intimately, that plus my warm feelings for Rachel which weren’t just about her gorgeous physical attributes. My previous lack of arousal really was disturbing and I pondered about it all the rest of the way home.
When I got to my room and could be alone, I took out one of my teen magazines as an experiment. It was one of those Mom had ordered for me with the subscription in my male name. At the time that was yet another source of humiliation, but it had shrunk into insignificance these days, as so much more was happening to me. I turned to a bra commercial which had caught my eye a few days before and I allowed myself to stare at the picture. The girl was pretty and the photo showed off her curvy body, revealing enough to get the imagination working. It was pleasurable to mentally run my hands over those soft curves; quite exciting in fact. They seemed so real that I could imagine just how they would feel to the touch! Strangely, I got no response from down below. Just nothing! This was a new departure for me and altogether confusing.
The following week I noticed how sensitive my ‘bust’ had become. To prevent undue attention being drawn to the swelling mounds on my chest, I had taken to wearing a tight singlet for school which flattened that area as much as possible. On this occasion I was in the corridor and there was the usual scrum for the lockers. In the ensuing press, I took an elbow in my chest which hurt like hell and left me sore there for the rest of the day. I showed the bruise to Mom that evening but was told unsympathetically that I needed to be more careful. Oh, and it was tiresome but it looked as if I’d outgrown my bra, again, and we should have to go for a fitting later in the week. I also pointed out that my panty-girdles, purchased new at the start of the school term, had also become way too tight. Though this statement was dismissed with initial disbelief, she checked me with her tape measure and reluctantly had to agree.
As arranged, on the Friday Mom picked me up from school and by the time we reached the shops I had performed my change-in-the-back-of-the-car routine and was wearing one of my day dresses. Instead of going into Sears, Mom led the way to a small store which displayed items of lingerie in the window. It looked a bit old fashioned and the interior smelled a little on the musty side.
We entered and waited while the manageress finished up serving a middle-aged woman ahead of us. It seemed to take her an age and I idly gazed around at the many shelves with their boxes and boxes until Mom’s none too gentle tug on my arm abruptly dragged me from my reverie.
The woman behind the counter seemed ancient and wore heavy makeup. As we approached we were greeted by “Madame’s daughter requires a fitting? That is easy to see.”
I was ushered into a curtained-off area and when bidden I unbuttoned my dress, unhooked my bra and stood while the woman ran her tape measure over me. As I looked in the mirror it was obvious how much more of me there was than a few weeks before, at least in one area.
“Since your old brassiere was fitted, you have gained more than a cup size” she remarked after checking the label. “A lot of growth even at your age, but what is less usual is that you seem to have lost some inches under your bust, if your last fitting was correct. You will need a band size which is smaller.” She gazed at me curiously and I flushed hotly. Apparently she made sense of what was happening to my body even if I could not. I felt like some kind of freak. My chest was slimmer but my bust was bigger. How was that happening?
The woman next inspected the long-legged panty girdle I was wearing. It felt comfortable enough around my waist but it was stretched tight across my butt and thighs. With a satisfied smile she declared. “This is the wrong shape for Miss. You require a girdle from our Curvy range.” She left me and returned with a couple of bras for me to try. Mom was called in to examine the results and eventually a pretty bra by Formfit was selected.

In shape it was somewhere between an everyday bra and the pointy bullet bras fashionable for evening wear in those days. My mother told the woman we would take two in the new size in white and also two corresponding ‘curvy’ girdles.
Everything a growing boy could need!