Archive for the ‘Halloween’ Category

The Halloween Sissy

Thursday, September 8th, 2016

Its never too early to plan for Halloween. Make sure you have the right lingerie, stockings, garter belt, corset or bra, heels and dress. You’ll also need to do something with your hair, and for many of you that means a wig.

Makeup help is always available and is as close as your local beauty salon. Ideally you’ll stop in ahead of time and make an appointment, then come in that afternoon or evening fully dressed.

Make sure everything fits, practice walking in your high heels, and decide on the right jewelry and perfume. You’ll also need a cute purse or bag for lipstick, extra panties and of course condoms.

Just don’t bite off more than you can chew.

Head to toe

Head to toe

The Halloween Sissy

Wednesday, October 28th, 2015

You’ve been planning this night all year, and you’re finally ready to go out into the world dressed as an adorable, sexy girl. Your outfit has been carefully chosen, you found someone to do your hair and makeup, your lingerie fits like a second skin, and you know exactly where you want to go and what you want to do.

I have a few quick suggestions to help you make this a memorable night.

1: Carry a medium to large purse. Not only will you need a place to stash your makeup, phone, and wallet, a full purse makes a great weapon if needed.

2: Bring extra panties, pantyhose and condoms. You may not need any of those, but just knowing they’re there will let you concentrate on having a great time.

3: Remember, you may be dressed like a slut but you’re not a prostitute, probably.

The Halloween Sissy

The Halloween Sissy

The Unique Vintage Crossdresser

Monday, August 31st, 2015

Yes its 90 degrees today, humid and sticky. It feels like one of the dog days of August, probably because it is. But August ends tomorrow and that means fall is just about here. It also means something very important to all you boys that like to dress up as girls. It means that Halloween is right around the block (not literally).

I suggest that you start thinking about it now, and I also suggest that you don’t get a cheap costume at one of those party stores. Consider buying something that you can wear again and again.

Now I know what you’re thinking, when people ask what your costume is, you don’t want to just say you’re a girl. OK then, how about an amazing outfit that you can wear again and again, that can also be considered a costume? Get ready for the most incredible collection of unique vintage dresses and clothing that you’ve ever seen. You can even choose a look based on your favorite era, the 1920’s through the 1980’s.

Picture yourself in this 1920s Style Beaded Mesh Flapper Dress. Gorgeous right? And not only does this dress come in sizes all the way to 2x, they have the matching slip that you’ll need.

Remember: Procrastination makes easy things hard, hard things harder. I understand if that confuses you.

Unique Vintage Dresses & Clothing

Beaded Mesh Flapper Dress

Beaded Mesh Flapper Dress

Halloween Sissy Story Contest – Its too short!

Wednesday, October 22nd, 2014

Some of you are complaining that one page or 1200 words is not long enough for a great sissy story. So let me give you a tip to make things easier.

Skip the beginning and get right into the action. Whether you’re caught in the closet by your sister or tied up by cheerleaders, resist the desire to describe everything that led up to the situation in minute detail.

Most sissies have limited patience unless tied up, so to make your story more exciting start in the middle. Remember, every reader will have one hand on their mouse and one hand in their panties.

Let me give you a graphic example. This guy seems to be in a bit of trouble. It doesn’t matter how and why he’s in this position, what’s important is what happens next. Ya feel me?

Remember, the Deadline for this contest has been moved up to October 31st 2014.

Halloween Sissy Story Contest

Pantyhose Bondage

Pantyhose Bondage

Official Dress Up as a Girl Day

Monday, September 1st, 2014

Yes its time to start thinking about that very special day once again. Official Dress Up as a Girl Day comes only once a year, and its your ticket to ride (or anything else you want to do while dressed as a girl from head to toe).

Of course I’m talking about Halloween.

You’ve probably seen pumpkins for sale already, and more importantly, advertisements for Halloween costumes.

On this special day you can do things you’ve only dreamed about, like go out in public dressed in your cutest outfit. Not only is dressing up approved by the entire world on Halloween, dressing up as completely as possible is absolutely encouraged. Now what does that mean to you, the average crossdresser you might ask?

It means panties, pantyhose, bras, slips, petticoats, dresses, skirts, blouses, wigs, FULL MAKEUP, nail polish, high heels, perfume, jewelery, and anything else you want to wear.

Do you realize that once you’re all dressed up, you can leisurely stroll though your local mall without a care in the world? Or walk right into your local beauty salon for a manicure? Or shop for lingerie, dresses and makeup anywhere you like, all while looking pretty and witty? Or have a set of professional photos taken at one of the photography studios tucked away in many department stores by a pretty girl who thinks you’re simply adorable? Well you can and you should.

This is my friend Claudia. He’s just a normal guy that likes to dress up as a girl as often as possible. Claudia doesn’t have to wait for Halloween to go out, but I think he’s one of the few that doesn’t. Most crossdressers never leave their house while dressed up. This is your chance-take it!

Tip: Halloween is on a Friday this year, so the whole week should be considered close enough to count as Halloween related.

Claudia Tyler Mae

Claudia Tyler Mae