Chapter 2 – A new departure

Inspired by Lipstick Discipline

An hour later with my hair fluffed over my eyes and neatly arranged – it still hadn’t quite grown out enough to be put in Mom’s preferred style of “dog’s ears” – and wearing my newest dress in bright blue with matching jacket, three inch white heels and purse, I followed Mom out of the house to the station wagon. The day was fine but breezy and the little gusts tugged fitfully at the hem of my dress.
She was dressed in her cream suit in a similar style. With white purse and heels just like mine we made a typical ‘mother and daughter’ couple. Mom had arranged for Tom to go over and hang out with one of his friends, Miles, and we dropped him there on the way to the store.
When we had parked up I slipped out of the car quickly and stood waiting while Mom picked up her purse and checked her makeup in the mirror.
“My, you are an impatient little hussy!” she exclaimed, beaming with pleasure at my eagerness which I have to admit wasn’t completely feigned. How come?! I couldn’t believe how well everything was working out, I guess. This treatment was so different from being yelled at or worse and I couldn’t get enough of it. It was gratifying to see her so obviously having fun too and to know my behaviour was the cause of it. I led the way into Sears and onto the escalator to the first floor.
“Legs together, sweetie” whispered my Mom “you never know who is looking.”
The hem of her skirt fell just below her knees, whereas mine was shorter, making this caution necessary. I found myself liking the feelings of vulnerability that this thought provoked, as if I were somehow delicate and fragile. I gathered the loose folds of material against my thigh, before checking around to see who might be getting an uninvited glimpse. There were a number of males on the floor below but no-one seemed to be paying me any attention. Now why was that realisation accompanied by a twinge of disappointment? Strange!
Mom’s knowing look revealed that she understood what was in my mind. “Jennifer! You little tease!” she laughed with mock reproof. I coloured up to the roots of my hair in confusion. What had I been thinking?
At the top of the flight was the fashion department. She stepped off the escalator and stood there giggling helplessly at my continued embarrassment. I grabbed her hand and pulled her still laughing towards the evening dress section. To my dismay, the dress I had picked out was no longer on any of the display mannequins on the stand.
“Oh no! It’s already been sold!” I cried, gesturing to the display dummies and feeling genuinely distraught.
“Calm down” Mom soothed. “I’ll bet there’s one on the rail, you goose! Come on! Let’s look!”
She was right of course and when she led me over to where a whole row of cocktail dresses were arrayed, amongst them I could see three examples of the one I had picked out, in varying sizes. They didn’t look as striking on the rail as the one I’d seen on the dummy so I still felt a little deflated, but when Mom had selected an example in my size and held it against me, my doubts started to subside. Yes, this would be a wonderful dress that any ‘girl’ would dream to wear. My mom was sure to love it and ought to be so impressed that I had chosen it by myself.
A middle-aged sales assistant made her way over to us. “Can I be of assistance, madam?” She addressed Mom, while I stood indulging myself in a fantasy of being the girl in that dress and surrendering to the charm of that fantasy.
“My daughter would like to try this dress” said Mom firmly. “Come on, dreamy one!” she said to me, rudely breaking into my girlish reverie by rapping me on the head with her knuckles. “We haven’t got all day”.
I was shown into one of the tiny changing rooms and handed the dress. The curtain having been pulled across behind me, I proceeded to hang up my purse, slip off my jacket and shoes and unzip my own dress. My fingers were fumbling with excitement and anticipation.
I took the dress from the hangar and undid the zipper. I saw that the bodice of the dress was stiffly boned and the sweetheart neckline had built-in cups, so I unfastened my bra and hung it up, as that item of underwear would not be needed either. The dress had attached petticoats sewn-in and I found myself searching through their several layers to find the intended opening. When at last I slid it over my head and arms, I was surrounded with fold after fold of slippery soft fabric. The sensation was thrilling and started the tingling down below again. I managed to ignore it and arranged the material, straightening and smoothing out its layers. I felt the bodice pulling my waist in as I did up the zip at the side. I had to exhale deeply before I could fasten it all the way. I slipped my shoes back on and finally I turned and looked in the mirror.
I was too close to the glass to take it all in, but what I saw was enchanting. The bodice had padded inserts in the base of each of its cups, so I’d had to ease the swollen mounds that formed my chest upwards, to fit over them. The result was a cleavage which would have done credit to a model in a commercial. My waist looked tiny, making my ‘bosom’ seem even larger.
I couldn’t take my eyes from the image. The effect it was having on my private area was beginning to grow stronger, when… “What are you doing, Jennifer?” My mother’s voice broke in upon me and at the next moment the curtain was swept aside. “Let’s have a look at you.” A pause then, “Turn around, sweetie”. I obeyed and stepped out of the cubicle.

Mom stepped back, took a deep breath and sat down on one of the chairs provided. An even longer pause, then she beamed at me.
“Oh, Jennifer! It looks amazing on you! You were right about this dress. I was going to suggest a couple of alternatives but……” her voice trailed off.
The assistant hurried over and added her compliments. “You have such a pretty daughter, madam!” Admired by all (another assistant came over and joined in the chorus of approval), I paraded up and down in front of the big mirror gazing at this wonderful creation. I actually found myself revelling in the all the attention I was getting.
Now that I was able to see the whole thing properly I couldn’t get over the realisation that this stunning creature, with décolleté bosom and hourglass figure, was little ol’ me. The thrill I was experiencing was up there with the best sensations I’d had as ‘Jennifer’ so far! I caught myself checking around the store for any male shoppers whom I might impress and feeling another twinge of disappointment that there were none to see me. Why was I even thinking that? Unexpectedly, thoughts of Chris Bennett flashed through my head and I found myself imagining him seated there and myself twirling round so that layers of the delicate skirt would brush flirtatiously across his legs. Then….
“We’ll take it,” said my mom to the assistant decisively; and to me “You can pay me back every cent, mind, and soon too. You realise that earning all that money is going to mean you’ll be spending much more time at your cleaning jobs.”
Perhaps I should explain about Chris. I’d known him from when his older sister Rachel used to babysit me and my little brother. Stunning to look at and kind in nature, she was always my idol of female perfection. Until recently Chris and I had never really hung around each other because of the difference in our ages. Nearly two years older than me, he was popular, athletic and smart; everything I wanted to be. However we’d encountered each other a few nights after my return from Dad’s. We’d called over to see his mother, my mom’s oldest friend, the night that my brief rebellion against Mom had been finally put down. When he put in an appearance during the course of the visit, I’d found him fascinating.
I’d never realised before but he was actually very good looking if you really paid attention to him. A shock of blond hair framed his face. He had blue, almost violet eyes that shone directly into mine and a pair of full lips formed a wide, fascinating smile. Curiously he seemed to be just as interested in me. This was really odd considering how I was dressed at the time and the way that my presence had been announced by his sister “Look who is here, Chris. It’s Robert!”
If I hadn't been so ashamed of my girlie appearance, I'd have thought him a pretty neat guy to hang out with. We kind of hit it off despite the shaky start, and parted as, well, as friends. Well, perhaps a bit more than that; somehow he’d ended up with the imprint my lips on his cheek! How had that happened?! I was definitely not into guys! No way!
My mind recovered from the recollection, back in the store. “Gee thanks Mom, you’re the best. I don’t mind paying you back, really I don’t. Oh, I can’t wait for Mrs Bennett to see me in this, and Rachel and…. and… er… C… er… Karen too!”
It was useful to substitute the last named at that point to hide my true thoughts. Karen was my erstwhile school sweetheart. She knew all about ‘Jennifer’ and was a sore subject with me. We’d got together not long after I first started high school and I had been crazy about her. However it soon turned out that she never wanted to go out with me in my boy clothes but only with my feminized self. On top of that I found out she was dating one (or two) of the high school football jocks at the same time as me! In my make-up and dresses I couldn’t begin to compete with them. She and my mom had formed an alliance against my masculinity which had made my life uncomfortable ever since. By now I’d given up on the relationship. Sort of… My daydreams these days went in other directions, one of which I didn’t like to acknowledge to myself, let alone discuss with my parent.
When I’d changed back into my own clothes, I caught up with Mom who had paid for the dress and was browsing absently around the store. I was pleased to see her looking a little dazed, at which I wasn’t altogether surprised. Perhaps she was having to adjust mentally to a great deal right now. What did take me unawares though was just how much I was loving this. We returned to the parking lot and I flounced across to the car on her arm. The way the wind flipped at the hem of my skirt chimed in with my elation, and I chose to ignore its fluttering, despite attracting stares from a group of high school boys we passed. I looked straight past them, head held disdainfully high, to their confusion and Mom’s evident approval and delight.
On the way home I wondered “what next?” The first thing that came into my head was to ask her when we might arrange our party, and actually I felt that I couldn’t wait!!! You can tell that this was going too well, can’t you? So I was to discover. My mother had fallen silent and was thoughtful. As we pulled up in the driveway I sensed that the fun-filled mood we were sharing at the store had somehow evaporated.
“What is it you’re not telling me?” The ominous question came from my mom before we got out of the car.
Baffled, I looked across at her, not understanding what she could be referring to. “Err... Mom?” I stammered, wondering what had gone wrong.
“Don’t play games with me!” she snapped back. “I know when you’re hiding something. What is it?”
“N... n... n... nothing” I croaked, aghast. SLAP.
“Don’t lie to me!” she exclaimed. “I know when you’re lying. You stopped short before you mentioned Karen at the store – you tried to cover it up but you weren’t thinking of her, were you?”
My cheek stinging, I looked in her angry face, and finally the penny dropped. “Oh!”
“Yes. Oh!” she went on. “Well!”
I really didn’t want to have open my inmost feelings up for discussion, so sat there silently considering what to say. Another SLAP. “Mom, please” I whined, my eyes filling with tears.
“Now just listen, little mister” she scolded. “It’s no good pretending to be my good little daughter, if you’re going to have secrets from me. You want me to trust you? Fine! That works both ways. Whatever is going through your head, you tell me. Whether you want to or not, you tell me! Even if you think I might not like it. Especially if you think I won’t like it! Got that?”
I looked away, choking back a sob. “I guess.”
“Pardon me!” she demanded.
“Yes, ma’am.” I said quietly, realising I would have to give in, no matter how it left me feeling.
“It’s for your own good, Jennifer” she went on in a calmer tone. “Pretty girls your age are vulnerable. Don’t I know it?!” she added ruefully. “You’re starting to think you can handle admirers? If you are going to be running around with kids your own age, you need an older and wiser head to understand what you are going through. Someone that cares enough about you to be sure and protect you! No secrets! Spill!”
I nodded dumbly.
“What were you thinking back in the store?” she persisted. All the recent ground I thought I had gained in her approval had been lost again apparently.
I hesitated. I really didn’t want to do this, but there didn’t seem to be any choice. “I was thinking about… well… I wanted Chris to see me in my dress, that’s all.”
Mom sat silently for several minutes. When I looked up I could see a twinkle in her eyes. “Chris? Really? Why had that got to be such a secret, then?”
I thought for a while “He’s different, I guess.” I thought some more. “I like him a lot. He’s a proper boy but he’s really nice to me, even though he knows all about me.”
It wasn’t getting any easier the more I talked to her. “He’s cute too. I can’t help thinking about him, even when I don’t mean to,” I wailed. “I… I don’t want to be a fa… I mean to have sex with boys, but I can’t help being… well… turned on by him. That’s awful! Right?” I ended tearfully.
“It is what it is” she replied gently.
I sat there miserably, tears welling in my eyes, feeling raw and exposed. She put her arms round me and I sobbed onto her shoulder. “Oh Mom, I feel such a mess inside.”
Later that day I had time to reflect whether my plan had paid off. True, it had been a rocky road with a stumble along the way, but the final outcome had been okay, and my mom and I were a mite closer than before. I reckoned that it was probably worth persevering with my attempt.