Ask Hannah!

I’m new to crossdressing, I have never dressed up in women’s clothes but want to. I am scared to this but if someone were to give me guidance I would love to do it. Another thing, I love the look of women wearing knee high riding boots and I want to see if I can pull that look.

I fully believe that crossdressing is something you learn my doing.  However, I do have a guide that might help you get started.

You can also see if your city has any transformation services that may be able to help.

And yes, you look good in knee high boots.  Everyone looks good in knee high boots.


Love, Hannah


Ask Hannah!

I would like to start a group similar to the MN T-girls but I am having trouble finding other CD’s that might join the group. Could you share some of the steps you took when starting the MN T-girls? Particularly how did you contact a community of people that is typically in the “closet”.


Congratulations on starting your group!  It will be one of the most rewarding and occasionally frustrating things that you’ll ever do.  I knew it would be difficult to meet others like me, especially those who were brave and confident and ready enough to go out.  Luckily I had a blog and had a lot of people who visited it each day.  I blogged about the group and invited t-girls in the area to email me.  Being a little web savvy, I knew the most searched term people used to find my blog was “crossdressing in Minnesota”.  I knew people were looking for others like me in Minnesota so I started to tag Minnesota on my blog so Google would start directing people to my site.  So, setting up a blog that is updated frequently is a good start.  Of course, starting a blog is a challenge in it of itself, but WordPress is very user friendly option.  You might want to start blogging about LGBTQIA issues in your home state, share your thoughts and experiences and write about resources for our community in your area like I have here.  A blog is a great way for people to get to know you so others feel comfortable reaching out to you.

The next thing I did was posting a thread on  There is a section there titled ‘Places to Go, Places to Meet’. is probably the biggest social group for girls like us.  T-girls constantly discover my group through this forum.   You may also want to visit a local PFLAG meeting and invite members to your group.

Creating, organizing and, maintaining a group like this is a challenge and can be frustrating at times.  But it is also very rewarding and fun.  It takes a lot of patience and professionalism and dedication.  It takes commitment.  It is a lot of hard work.  It takes a lot of my time.  However, through the group I’ve been able to do many amazing things and I am constantly looking for new adventures for us.

I will say if you are going to create a group then it really is something you need to commit to. You’ll need to stay in contact with the members, keep them updated about outings and listen to requests. You’ll need to be reliable and consistent. You need to be social and outgoing and friendly and confident. The group really brings me out of my comfort zone in terms of being social, and I really need to be organized and plan ahead. You’ll also need to be able to not take things personally. There have been many events where ten T-Girls say they’ll be there…but two show up. There are times when I get frustrated when not as many girls show up as I expected because the events can take a lot of time to plan. Most outings take a few weeks, or sometimes even months to plan. The last outing was in the works for three months, for example.

I wish you the best of luck! I hope it goes well and thank you for creating a group!  Let me know when you group is up and running and I’ll writ a post about it.

Love, Hannah


Ask Hannah!

How do I know if I’m a crossdresser or if I’m transgender? And if I am transgender, then Ok, I’m transgender. Now what?  Do I really have to come out?  I can’t afford a therapist. What do I do?

As far as I know, there is no agreed upon definition of what a crossdresser is.  But if you asked me what a crossdresser was, I suppose I’d define the term as an individual that enjoys wearing clothes that are traditionally associated with a different gender.   A little vague but I think most people get the idea.

Personally I think all crossdressers can be considered transgender.  I wrote a little about this here.  To be honest, you can identify as however you want.  I started to identify as transgender when I realized that all….THIS went beyond just panties and heels.  Identifying as a gender (even on a limited basis) that was different than the one I was assigned to at birth was what really pushed me to identifying as transgender.

If you are transgender, well, okay, now what?  Only you can answer that.  Coming out as transgender is not the same for everyone.  There is no next step you have to take.  Coming out is not the same for all of us.  Do what you feel is right.  Take it slow, though.  You can come out if you want to.  But you don’t have to if you don’t want to.  There are no rules…except for wearing non-nude stockings with open-toed heels.  Don’t do that.

If you can’t afford a therapist, please, reach out to PFLAG.

Love, Hannah


Ask Hannah!

I’m a married man that crossdresses. My wife knows about it. I’ve been crossdressing for quite some time now and the one thing I’ve always wanted to do is go out in public. My wife is not ok with me going in public all dressed up. I was wondering if you have any advice for that.

Yes, my advice is to listen to her.

Relationships and…what we do and who we are, are not easy.  Some of us have partners that participate and help us shop or put together an outfit or hit the mall with us.  Some of us have a “don’t-ask-don’t-tell” policy, some relationships are very tense due to this, and some of us haven’t come out to our significant others.

Telling our partners (mind, I use the term telling our partners as opposed to being caught by our partners) can be a huge weight of our shoulders.  We need to be honest with ourselves and with our partners.  I know it’s easier said than done, but it’s the truth.  And we need to have these conversations when the relationship get serious.  Not after you move in with them, not after you get engaged, not after you get married.  Before.  Before any of that.

Keeping something as big as this a secret is almost suffocating.  But we need to tell our partners.  It’s better to be up front with this than it is to be caught.  Once this secret is out, then we need to conscious of how they will react to this.  They are coming to grips with this, too.

And yes, once you come out to your partner, they will likely set boundaries.  Sometimes it’s not telling the kids or telling anyone else, or not posting photos or not chatting with anyone online or not leaving the house.

Sometimes boundaries can be a small price compared to stress of keeping a secret.  Out of respect for your wife, respect these boundaries.  She is dealing with this, too.  Be respectful of her and her feelings and her request.

If you go behind her back, you run the risk of losing her trust.  And nothing is worth that.

Love, Hannah


Ask Hannah!

I’m in a sexless marriage. I started to dress a while ago because it makes me feel special. Are there any places near Ann Arbor Michigan that I can talk to ?

I would encourage you and your spouse to seek out counseling when it comes to your marriage.

I would also recommend reaching out to PFLAG, who, according to their website, unites people who are lesbian, gay, bisexual, transgender, and queer (LGBTQ) with families, friends, and allies, PFLAG is committed to advancing equality through its mission of support, education, and advocacy. PFLAG has 400 chapters and 200,000 supporters crossing multiple generations of American families in major urban centers, small cities, and rural areas in all 50 states.

There are chapters all across the country, including one in Ann Arbor.

Take care.

Love, Hannah

Ask Hannah!

New to cross dressing. Do you know any great studios in NYC to start me on my journey.

Thks so much.


Sometimes I wish I could relive those early days of transforming, at least temporarily, my gender.  I have been transgender even before I knew the word existed.

But I digress.

I have never been to New York but I would love to go.  A quick Google search of the terms ‘gender transformation services NYC’ provides quite a few options.  Here’s a few:

Miss Vera’s Finishing School for Boys Who Want to be Girls

Monica Prata

Fairplay Imaging

I wrote a small article on Miss Vera not too long ago which you can read here.

Your journey will be your own, and all of our journeys are different from each other and end at different places.  Transforming your gender is about creating yourself.  This is something you learn.  This is something you learn by doing.  It can be a humbling, frustrating experience.  I have no doubt that you’ll have an amazing time at any studio you visit.  Just be prepared that professional work is not free.

My only caution is that your first (or one of your first) experience with makeup is with a professional makeup artist.  You will look amazing, you’ll feel even more amazing-er.  I know that’s not a word.

However, depending on how often you dress up, it may not be realistic to be able to visit a professional each time you want to get glammed up.  Eventually you’ll have to learn to do your own makeup.  If you’re like most of us, your first few attempts at makeup will be disappointing.  It took a long time for me to be happy with doing my own makeup.  But the more I did it, the more I learned and the happier I was…my skill and confidence grew.

It was a few years of doing my own makeup before I had a professional makeover, and a few years after that until I had a makeover with someone who had specifically trained in the art of gender transformation.  I am still amazed at the magic Corrie at Midwest Makeup Supply can do.   I’m glad I had been doing my own makeup for years before I had these experiences.  Had I visited with Corrie or another professional that early in my journey I would have been incredibly discouraged when I did my own makeup after that.


The photo on the left was one of my first attempts, probably taken about six years ago.  The one on the right is from earlier this month.  If I had started with a professional makeover my heart would have sunk as I would not (nor will I ever) be able to duplicate what Corrie did, but these days I am happy with my makeup.  But it took some time.

Working on your look has a lot to do with keeping your expectations realistic and always, always practicing.  I’ve said it many times before and it will likely be etched onto my neon pink tombstone, but crossdressing takes time, practice and money.

Don’t get discouraged when it’s time to do your own makeup after visiting with a professional.  Don’t be too hard on yourself.  Don’t give up.

Love, Hannah




Ask Hannah!

The Super Bowl is in your town this weekend. Are you a football fan? Do you plan to wear a football themed outfit to watch the big game?

I was wondering why there was so much more traffic this week!  😉

I am not a football fan, so I am not planning on watching the Super Bowl.  But even though I am not a Vikings fan, I still wear purple on occasion.


I am proud that Minneapolis is getting a lot of attention at the moment, though.  I think we have an amazing city for many reasons.  It’s a very progressive city that has a lot of resources and support for our community.  In November Andrea Jenkins became the first out trans woman of color elected to public office in America.  The University of Minnesota also recently curated an exhibit documenting the history of the transgender and gender non-conforming community. IMG_0593


If you’re in town for the game I hope you enjoy our city and I promise you that it’s not normally this cold.

Love, Hannah