While not much of one to use labels, I talk to a good number of transgender, sissy, and fetish crossdresser callers. While each is unique, there is one sentiment that I’ve heard expressed to me on many occasions. It’s a wistful longing for the feminine things that they didn’t get to experience during their early years.

Those conversations have caused me to think about what could be done to help alleviate that feeling. Though one can never go back, I think that we can create situations and experiences in our current lives that feed our unmet needs.

After a couple of months of mulling it over, I’ve come up with something that I believe will not only be girly fun, but it will also involve prizes. And what pretty thing can say no to the opportunity to win something fabulous?

It won’t be long before Spring is upon us, and all sissies and fembois worth their collective salt know that means an explosion of fashion, color and new sissy makeup collections. Those things are just what we need to help get us out of the doldrums that winter can often create.

Sissy Style Off

I’m going to hold a Sissy Style Off contest. You are all invited to participate and get your girl on. It won’t cost you a dime, and it will allow you to do something along the lines of playing virtual paper dolls, and most importantly, will let you express your marvelous creativity!

This 3 part sissy assignment is your first step toward participating in the Sissy Style Off:

You are to go to Polyvore and create an account.

Once you have a profile there, click your username. That should bring up a page that shows a toolbox. In that toolbox, you’ll find the option of finding members to follow. Search for my username (msclaire) and follow me.

After you’ve done that, you need to go to my blog, and look for the post that is announcing the Sissy Style Off. That post will go live sometime on January 30th. After it does, you need to comment there with your Polyvore username.

The prizes and official rules will be contained in that post on my blog. So be sure to study them to know exactly what you need to do to win. Not knowing the rules will not be considered a valid excuse, and will not only disqualify your entry, but it will earn you a spanking and sissy humiliation of the unpleasant variety.

Questions? Exhibit some sissy patience, wait until full details of the Sissy Style Off are unveiled, and ask them at my blog or in the comments below. In the meantime, browse Polyvore and look at some of the incredible sets dreamed up by others.