First time…..

Musings from WannabeGinger

For all of us, there are many “first time” for many things in our lives. Here are a few more of my own.

Chapter 3

There I stood, lipstick tasting creamy on my lips, with one of my Mum’s bras in my hands. It was black and lacey. It was quite a thing of beauty in my teenage mind. How did it fasten? How would it fit? Why was it so attractive? What would anyone say who walked in now…?! Mum, or Dad, or a Brother? How could I explain what I was doing? I had no answers. And yet, I had this compulsion to put the bra on myself. To feel what a girl feels.

Of course, girls think nothing of it — the experience is an everyday thing, so it’s unnoticed, no doubt. But the first time?? This was my first time….

Girls get their first time experience of wearing a bra with their Mums, I’m sure. Then it’s special. They’re growing up into young women. I couldn’t feel that. I had no Mum there to share it with. If she were there, what would she say if I asked if i could try a bra on? I'm a boy, for Chrissake! I couldn't ask... of course, I couldn't. I’ve read stories about young men who have had understanding Mums to share a first wearing of a bra and panties with. Some have even been the driver of the idea. Mums who wanted a daughter.

I’ve always thought these were excessively unreal….. but maybe such things do happen. Lucky boys, I say.

I struggled with the bra. It seemed to have a mind of its own. My arms went through the straps over the shoulders ok….. but the cups where my tits would go turned inside out. My tits? What tits? Oh, if only…. For the first time in my life, I wanted tits!

How many times since that moment have I wanted tits! Of my own!

Off came the damned thing and I turned it inside-out, or inside-in I guess. Arms back through the shoulder straps. Now there it was, hanging loose with the chest strap flapping down either side. How to get them to join up, behind my back? I grabbed at each one in turn. Why hadn’t I looked at them before putting it on again? They felt like snakes.

(I later learnt the trick of fastening the bra at the front and sliding the strap round to the beck before putting arms through the shoulder straps. Why doesn't anyone tell you that when you're a thirteen year old boy!?)

I looked over my shoulder and saw that the bedroom door was wide open…. What if someone came up the stairs? They would see directly in to where I was standing…….. I crossed the room and cautiously looked outside, and listened….. Nothing could be heard. Nobody about….. the bra continued to flap, the cups staying across my chest.

I could do this…… I was sure……….

I reached behind me again, this time in front of the mirror. I was captivated by the scene. There I was, my panties looking perfect, my bra looking a total mess, and my face smeared with lipstick. My hair was tousled around my face. I must do something with that….

I thought then for the first time how important hair is in my appreciation of a woman’s beauty. How much I felt it was important for my hair to be right if I was to play a girl in my secret dream.

What a dream.

That bra strap in my left hand was more difficult to grasp than the one in my right. That was ok because the right side had the hooks in it. The left side had the eyelets that needed to be located by the hooks.

I had to stretch the fabric of the chest strap. The elastic had plenty of ‘give’ in it. The bra was also quite a bit larger than my slender body needed. After all, Mum was a 5ft 7inch average woman whose size wasn’t as small as she would wish!

Good for me… to get this beautiful lacey creation on to my back.

Getting my arms behind my back was awkward — unusual for sure. I never had cause to put my hands right up behind my back. If I was a girl, I realized for the first time, I’d have to do this every day. I continued to struggle. My mind was focused on nothing else.

Success! For the first time, I caught a hook into an eyelet behind me.

Damn! It was a top hook and a bottom eyelet. I could tell it wasn’t quite right. The strap across behind my back cut into my flesh a little. It wasn’t flat across there like I knew it should be. What should I do? Un-do it and risk not connecting again…. Or risk it? I decided to risk it……

Success! Second time lucky….. or thirty-second time more like it. The bra felt snug across the front but now there was too much slack in the adjustment for it to fit well. After all, Mum had a larger frame than me. But it was good enough…. Good enough for me to stand and look in the mirror again.

There I was, just me, being the ‘me’ I could be in my dreams.

I went back to the bathroom, where Mum did her make-up. I wiped the lipstick from my lips and took time to re-apply it, avoiding looking at my acne-marked face as best I could. Geez, how I hated those zits! The lipstick went on smoothly. For someone with no practice, I think I did better than could be expected. the colour was deep burgundy red. The outline of my lips, taken slowly, was easy to follow.

I took Mum’s hair brush and spent some time moving my hair around. I had washed it in the shower that morning so it was easily shaped. I divided it with a central parting, allowing each side to fall down to my ears, and a little beyond. I made a transverse parting in front of the crown and brushed the hair back from there, leaving a raised crown Satisfied, I returned to the bedroom.

For a moment, I was conscious that time had been running by so fast. I had over-stayed my welcome in Mum’s private space. The bra had to come off…….. I paused for another long appreciation of the image in the mirror. Yes, for a first attempt, this was really a girly me.

Off with the bra! Easier said than done. The whole process in reverse. Undoing the hooks and eyelets was a nightmare. It seemed to take for ever.

Once removed, the bra had to go back in the drawer where it had laid before my attack! I put the bra back in where I had taken it from. I laid it as flat as I could, remembering that the cups had been folded in ‘spoon-style’ and the straps had been under them. Now, was that drawer open or shut? I couldn’t remember. When I had come in… could I see in the drawer? I had to know — to leave it as I had found it.

To get that wrong would invite suspicion. How did Mum usually leave that drawer?!....Panic!

I had to make a decision. All of the other drawers we shut. So I shut this one. Only time would tell if Mum thought there was something unusual. And maybe I’d never know, because, probably, she would say nothing.

I walked back to my bedroom wearing only my lovely panties, determined that the next purchase with my wages would be a bra, as I had already planned.

I sat in my room for a while before getting dressed, covering up my wonderful panties with my boy clothes. All the time, in the mirror above my desk, the lipstick looked good. It tasted so gorgeous. Surrounding my face, my hair looked really nice.

My thoughts went back to that little Jewish girl, Riva, whose ginger hair was so beautifully styled in a bob cut. For the first time, I wished I was a redhead, not a light mousey-brown.

Chapter 4 will take you on to my mid-teens and the many first times that come at you like a tsunami when you're 15, 16, 17......