The First Dressing

(Originally written late July 2012)

I dressed up for my girlfriend the other day – and loved it. Let me explain the events leading up to this.

About a week ago I ordered a ton of makeup on Amazon. Pretty much everything the internet said I would need. The makeup arrived, along with my new wig the day after and I was off to the races. When my girlfriend went out I put everything to use and was shocked at the outcome.

No, not completely passable, but different – much better. The different make up and a decent wig make is enormous – perhaps an even bigger jump than the silicone breasts and padding. I actually looked kind of female – and from a distance I may have even passed. At least I’d like to think.

Anyway, I took everything off quickly and when my girlfriend came home I told her what I’d done – and that I wanted to dress up for her too.

A few hours later, there we were, in front of the bathroom mirror watching me attempt to transform. She gave me a few pointers with the make-up, which I enjoyed, and then a few minutes later the change was complete.

I don’t think she was weirded out until the wig came on. I stood from half a room’s distance at first. Kind of like a frightened animal, not sure about my proximity. She came closer – and was, a little scared, but hopefully also slightly impressed.

We sat together, and she let me kiss her on the cheek. I am not a bizarre crossdressing monster. Success.

I didn’t stay dressed for long – I wasn’t really sure what to do or say. Regardless, I was happy. This felt like a very big step.

In the proceeding days I dressed in full one more time, when she went out for a run. This time, I stayed dressed when she came home and let her find me this way. She later told me that she liked that I was dressed when she came home. I want us both to be more comfortable with this.

Yesterday we went to the mall together – and I, kind of, got to shop for women’s clothes for the first time. She really did the shopping for “her” with me present, giving awkward advice. It’s tough to balance being excited about being in Victoria’s Secret Pink, but at the same time pretending to be the boyfriend dragged there unwillingly. Totally opposite ends of the spectrum.

In the end I/we picked up a few things that I’m excited about:

  • Long sleeve white shirt, to wear under short sleeve t-shirts.
  • Black long sleeve carigan to wear over other short sleeve clothes.
  • Victoria’s Secret PINK ¾ sleeve Mets shirt (this is both of ours)

The Mets shirt was my favorite pick-up, however it doesn’t quite fit as I’d like and the sleeves, of course, aren’t as long I would like in my ideal world.

That night, when we were going to sleep, I asked if she minded if I wear the shirt, along with the breasts and she was okay with it. I think going shopping, and this whole series of events in general has brought us closer.

I’ve since ordered three baby doll t-shirts online, along with four long sleeve crew-neck shirts and a dress for Halloween. Yes, I know it’s months away, but I can’t help but be excited about it.

Tonight my girlfriend helped pluck my eyebrows – not too much, though. I was nervous about how it would turn out, but it’s not nearly as drastic as I expected and they could probably use a little more. I feel like enough was plucked from my eyebrows to create an entire third eyebrow for someone in need. And my eyebrows are still bushy.

So I’ve accomplished a lot on my to-do list already, which is quite exciting. Much faster than I would have expected. You have to realize, though, that there is ten years of repression here all coming out at once. I think my recent “obsession” will boil down eventually to a normal hobby. Well, maybe not normal, but a hobby, none the less.

I do know, however, that I am looking forward to getting dressed up again. I have picked up with my girlfriend some makeup remover, which I’m oddly looking forward to trying, as well as a hairbrush and some girly sunglasses.

Things will continue to get better, and more comfortable. In the meantime, I will await my deliveries, knowing the more I think about them, the slower they will take to arrive.

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