Casual Updates

So much tell everyone regarding the weeks following my transformation session, but it’s late, so I’m going to be quick.

Halloween – I was Little Red Riding Hood, while my fiancee was the Big Bad Wolf. Totally rocked it, and told a number of people (quite clearly) about the role crossdressing plays in my life. Felt good.

Casual – I’ve been doing a lot more casual/hidden-in-plain-sight dressing lately. Leggings beneath jeans, underwear, painted toe nails. It’s easy to do, and makes me happy.

New Wig – I couldn’t get over how much I liked the long-hair pictures from the transformation session, so I bought my own long hair wig. It arrived this week, but I didn’t get a chance to try it on until today. It’s a little bit browner than I thought I was getting, but after playing around with it, and wearing half the day, I think I have it under control. Here’s a pic of the wig, front and back.


front and back

Overall, I think the short wigs do a better job of shaping my face, but there’s nothing like having long hair to play with and style. The brown hue is also growing on me.

In case anyone was curious, there are about 40 pictures from the transformation on flickr. At some point I will edit a few to make my postable here, but they’re worth creating a flickr account for, because his make-up job is fantastic. I can’t wait to go back.

I want to update a bit more frequently going forward, but easier said than done. Until next time!

All It Takes

I guess all it takes to get over a little dressing related stress is to in fact, dress.

New wig came few days ago, ordered from Etsy. It’s the cheapest wig I’ve purchased, and one of my favorites. Double win. I wish there were a few more layers of hair to thicken it out a bit, but it’s not that big of a deal.

What’s the point of questioning why you want to dress? Even if it remains an unsolved mystery, so be it. Not going to question what makes me happy.

See what books you can recognize in the background

New Wig!

I’m enjoying myself so much, I think I’ll dress again on Sunday.

One Of These Things

I hate posting twice in one day, but during my never ending quest to find the perfect wig (affordable, black, shoulder length, lace-front, with some bangs) I came across something golden.

Before you look ahead, some brief back story.

Google Images has a wonderful feature that allows you search using actual images as your query, rather than words. I found a great wig on ebay (affordable, shoulder length, lace front, with some bangs) except the color was off. In an effort to find another wig seller with the same wig styles, I used this Google Images feature. My results are below.

Just doesn't belong....

What doesn’t belong?

Can you figure out what doesn’t belong? Hmmmm….



  • Taking a walk around the block, dressed, with your girlfriend, is the most wonderful feeling in the world.
  • Crossdressing is more competitive than I thought before I started – every time I think I’ve done a good job with something, I see someone else has done it waaaay better.
  • Payless UGG knock-offs are awesome and comfortable. And look great with leggings.
  • I have a new lace-front wig coming in the mail soon. Not quite sure how it works, but I’m hoping it has more styling options than my current wig. Does anyone know if it’s possible for a human-blend wig to get split ends?
  • Halloween costume is coming together nicely. Going to need some gorrila tape to keep some articles of clothing in place. Expect a pictorial Halloween costume themed post this weekend.
  • I took a great picture tonight, that I wish I could post unblurred – the below will have to do, though. The clear photo, and more, can be found on Flickr. (Contacts only – add me and I’ll add you.)
  • Number of propositions received since I started crossdressing: 3.
  • Number of propositions received in over twenty-five years of male form: 0 (not including girlfriend or exes.)
New Necklace

If you squint, it looks kind of clear.

A few more days until the weekend! Looking forward to a relaxing weekend of crossdressing, football and pizza.



Convincing? You’ll not notice my hairy arms cropped out. You will notice the bottom of my new wig. It feels great. Soft, flowy…. but it’s also a bit wild, and I don’t care for the way it parts. I’m going to see if my girlfriend can straighten it. I like the look of my synthetic wig better, but this one is clearly higher quality. Alas, like a real head of hair, I’ll have to play around with it.