Ask Hannah!

Dear Hannah,

I came out to my wonderful, selfless near saintly wife of 18 years. She knows what transgender is just not who it is. What I know is that she loves me and that will not change :):):)
It can be delicate for a while. Both of us just letting it digest. This can take overnight or it could take years (this would be a mutual denial) This is my greatest fear. The girl wants out and she wants to be acknowledged. To just go into a holding pattern would be worse then internalizing it.
Support groups? Books? Therapist? ( OK, I have one)
Any advice?


Coming out to anyone, especially your significant other is probably one of the hardest things we will ever do.  I’m sure it wasn’t easy and I’m glad you did it.  It’s always better for us to come out as opposed to being caught.  I get at least one email a week from a significant other of a crossdresser or t-girl who pour their hearts out because they caught their boyfriend, fiance or husband or discovered their wardrobe.  Many times it’s not about the clothes, it’s about the lying and not being honest with them.

I know it’s not easy, but I urge you all to please, please tell your significant other about this side of you before get married or live with each other.  I know it’ll be hard, but you owe it to them.

But I digress.

When you come out to someone, especially a significant other, it’s easy to let things get out of hand.  For many of us we have kept this part of ourselves secret for so long that it’s a relief to talk to someone about it.  It’s possible we’ve never talked about this to anyone else and soon our experiences, desires and secrets just pour out.  This can be very overwhelming.  The person you came out to is still processing this information and when you add more to it, it can be a lot to take in.  Take it slow.

When it comes to what’s next, well, that’s up to you.  What do you want to do?  What do you currently do?  Do you dress at all?  With my wife I did not go from coming out to dressing completely in a couple days.  It took time for both of us to adjust.  It started with her seeing panties in my dresser and her getting used to that.  Then sleeping in a nightgown and so on.  It was about four years after I came out before I was in a dress, makeup and a wig.  I didn’t always make the right decisions during this time and I got lost in the pink fog a lot, but my wife is an incredible person and she was always honest and direct with me with what she was thinking, feeling as well as what she was and wasn’t comfortable with.

Don’t be surprised if this is two steps forward and one step back for a while.  Don’t fight her if she asks you to not dress up for a few days…or weeks or around her.  If she sets limits or boundaries, respect and honor them.  You mention you have a therapist, perhaps you may consider a couples session where the two of you attend to discuss this part of you.  She may also need someone to talk to independent of you and I would recommend PFLAG, a wonderful organization that provides, among other things, support groups for our friends and families.

Good luck!

Love, Hannah

Ask Hannah!

For background, I am a straight, closeted crossdresser. I identify as a “sissy” meaning I tend to prefer frilly, innocent outfits (think baby dolls and Alice in wonderland) … dressing is arousing for me … and I am not interested in really being female in public.

Here is where I could use some advice. I have three outfits but I always feel intimidated to put them on (they are a bit over the top in terms of frills and lace so not really public appropriate). And when I do, I put them on and don’t really know what to do with myself. I’ll curtsy a few times in the mirror and then put everything away.  I think about dressing a lot but I don’t understand why I only allow myself a few minutes to feel pretty and then pack “Ashleigh” away. Do you have any advice as to why I might feel this way or ways to explore my dressing in more fulfilling ways?



I like to think that the term ‘transgender’ covers a lot of different forms of gender identity.  Someone explained to me that the term covers any form of identification that is outside of the normal cultural norms that are associated with the gender that is assigned to someone at birth.  So, by that definition I believe transgender can cover everything from drag to transitioning.

As a lifelong crossdresser/t-girl, the world of sissy dressing is not new to me, although it’s not something I’ve ever explored.  However, I think part of us feel that there is a bit of a shift in personality as we go from one gender to another.  I certainly don’t feel that there is a lot of overlap in both of my lives/genders.  As I get ready and do my makeup, I definitely feel myself…crossing over.  It’s a strange feeling and not easy to explain, but I think many of us can relate.

I used to feel a bit of a blend between both sides of me, regardless of which gender I am presenting as.  But over the last few years, I feel the separation of my two sides are more defined than ever.  As Hannah, I almost completely withdraw from my male life.  I don’t do the things I would normally do as a male.  The same is true when I am in male mode.  When I am out running errands, I won’t drop by Sephora for eyeliner.  I’ll wait until Hannah is out.  It feels a little odd to me to do things as one gender for the other.

I think you need to let yourself slip into your other self.  You need to mentally shift into your other gender.  It’s easy to feel a little self-conscience as you dress and when you first see yourself in the mirror.  But let go of your male side and enjoy you are.

You may also consider exploring your female side in other ways.  You obviously love frilly dresses, but perhaps considering wearing clothes that are less “dress up” and more casual.  I think for some (not all) that dress up as a sissy do it as a fetish or a sexual thrill and for many of us, that’s where our gender exploration began.  It’s certainly where I began.  But I evolved, I tried other clothes that were less fetish-y and more appropriate for a night out or an afternoon at the mall.  Perhaps if you dressed in a way that would allow you to blend in, you may feel more comfortable leaving the house.

The clothes you wear can have a direct impact on how you feel.  I have a beautiful floor length ballgown that I absolutely love but I feel a little silly when I where it my living room.   I feel much more comfortable in a casual dress.  And killer heels.

I hope that helps!

Love, Hannah


Ask Hannah!

Maybe more of an observation than a question. Since only a small few of us t-girls can truly pass I think it’s imperative to then master the finer things to near perfection. I think it’s more thrilling to be in public with your hair and makeup on point and your clothes and accessories to be age and environment appropriate causing a stranger or passer by to either not notice or simply nod with appreciation for looking good and “playing” the part.

Now you are much more public and accomplished than I’ll ever be, so I’d love for you to share your point of view.

Thank you.

I’ve written a little about what I call ‘the myth of passing’ and the older I get and the more I dress, the more I stand by it.  I don’t think passing is something that is realistic for any of us.  I think if I waited until I thought I passed I’d still be sitting in my car in my garage.  Of course, I would have missed out on so many amazing experiences that I’ve had.  I sometimes wonder what I missed in all those years before I was confident enough to go out.

Look at this picture.  Do I “pass”?


414It doesn’t matter.  I love you all, but it really doesn’t matter to me if you think I pass or not.  I look at the picture and I see ME.  I remember the day it was taken.  It was a Saturday in July, I spent the day at the Mall of America wearing my new dress.  I found an amazing new outfit, spent too much on makeup and bought a pair of black heels.

Looking in the mirror, I know my shoulders are broader than most cis-women, I know my hands are larger, too.  But that doesn’t mean women, trans or cis have to have hands of a certain size.  I’ve seen women basketball players that are taller than me in my stilettos.  And I have tall stilettos.

What got me out of my room, my house, my car, my garage all those years ago was a complete and unshakeable confidence in myself and the undying desire to experience the world in a way I always wanted.  I wanted to feel the wind through my long hair, to hear the click of my heels in the mall, I wanted to see my lipstick on the lid of a Starbucks cup.  I did it and I’ve never looked back.

I love looking my best.  I know I am likely the most overdressed person in the room, the store or the entire mall.  You’re right, it is a thrill to be out with the perfect necklace and accessories and heels to match my dress.

People stare, people take a second look, people say wonderful things, people smile sincerely, people compliment…and that’s all okay.  Even the smirkers.  People look at me as if they’re seeing a transperson for the first time…because there is a good chance they are.  I know I am representing the transcommunity and I want to look my best for us.

It’s okay if people think you’re trans.  And really, you’ll never, EVER know what people think of you unless you ask them.

I never see what I do as “playing the part”.  I simply am who I am.

Love, Hannah

Ask Hannah!

You’ve been doing this for a long time and clearly it looks like you’ve become quite confident, but my question to you is, over time has your crossdressing become less exciting or thrilling or fun? Have you come to a point where you’ve committed to going out as Hannah and then you get bummed or stressed because of having made a commitment to be Hannah?

It’s my firm belief that one is always a crossdresser.  We do what we do because it is who we are.  No matter how many times we purge, or promise ourselves…or others that we will never do it again, we almost always do.  Because of this, I think that crossdressing will always be exciting and fun to us.  It’s who we are, but there’s a reason we keep coming back to this.

But I understand your question.  I always want to feel that going out as Hannah is special and fun.  One way I help make that happen is by really limiting how often I dress and go out.  I go out about twice a month which is often enough to satisfy me, but not enough to take away the fun of it.  Limiting the times I dress and go out helps keeps my wife from feeling overwhelmed by who I am, too.  My wife is wonderful and accepting of my femme side, but a large contributor to her acceptance is that I don’t overwhelm her with it and I’ve found a good balance with both sides of who I am.

Love, Hannah

Ask Hannah!

There are times this father of a daughter and loving husband feels feminine. Very, very feminine. I like to dress up. I like being a woman I have always felt this. I have always felt that I should be not a masculine being but the other end. I cannot explain it any better then that. When the phase shifts I am again man. I put away the dresses. The shoes (hardest part. I LOVE my shoes). I really don’t know. Am I a t-girl? A wannabe? A pretender?  The last thing I want is to diminish the bravery that you and other have shown in show in the world who you are. Are there others like me? Caught between one life or another?  Who am I?

I think most of go back and forth between how we identify ourselves.  Sometimes these identities can change throughout the day, or even longer.  Four years ago I identified as a crossdresser; these days it is transgender, but I prefer t-girl.  The term transgender does cover a lot of different identities, and labels, if you will.

My suggestion is to stop stressing about how you identify.  It’s okay if it changes.  It probably will, however, the term transgender is a bit of a catch all and likely covers everything we all feel we are.

It’s also normal for many of us to shift back and forth between what we feel like doing.  Sometimes I feel like reading, sometimes I feel like doing yardwork, sometimes I feel like getting a makeover.  You don’t have to pick one thing to do, to wear, or to be.

And yes, there are others like you.  There are so many like you.

As for myself, I fully embrace having two lives, having two genders.  Sometimes they blend together but why should I pick one?  Some of us do, but I like having options.

Love, Hannah


Ask Hannah!

I love reading about your adventures and experiences.  You say that you think you are too tall to pass in public.  Would you tell me how tall you are without shoes, & then how tall of a heel that you wear?
The reason that I ask is that I am 6ft 4 in. barefoot, I wear 2 1/2 inch heels, as that is the lowest heel that I am able to find in a size 17 women’s shoe.  Flats do not seem to be available in that size.

I don’t think anyone is too tall to pass.  I don’t think anyone is too…anything to pass in public.  The only person’s opinion about whether or not you’re beautiful is your own.  What do you care if the guy you walked by at the store doesn’t like your look?  It doesn’t affect you.  You’ll never please everyone, so focus on making yourself happy.  I don’t think you can have standards as to what one should look like to look like a woman because then we have expectations on what a cis-woman “should” look like.  Have you ever looked at a cis-woman and thought she was too tall to look like a woman?  Every time I think I am the tallest girl in the mall, I see a girl taller than I am.

I say this because I’d like to do my part in moving our community away from the need to “pass” and helping others really examine why passing is a myth and ultimately an unrealistic expectation and holding us back.  I don’t know a single cis-woman who worries that she is not pretty enough or short enough or not girlish enough to “pass” as a woman in public.  I’ve never heard a cis-woman say that she is too tall and people won’t know she’s a girl.  Cis-women know that all women are different and have different bodies and are different sizes.  T-girls are not any different.

I digress.  I am a little over 6 feet tall and I wear everything from flats (no, I’m kidding, I don’t wear flats) to five inch stilettos.  I usually leave the stilettos at home and wear a 2 or a 3 inch heel when I go out. I am not trying to pass or blend in by wearing the shorter heel, I dress and wear what I wear based on what is appropriate to where I am going.  A tight mini dress and sky high heels are perfect for a club but you’ll stand out at Target.

So, mall outfits…

These, not so much.

I am surprised you’re having trouble finding flats in that size.  Have you visiting this site?  I think you’ll have better luck online.

I hope this helps!

Love, Hannah

Ask Hannah!

Do you have any other hobbies?  Or do you focus on crossdressing related activities in your free time?  Just curious.

I like to keep busy and I am almost always doing something.  Sitting on the couch watching tv is not something I do very often.  I do like to read and I stay active by running, biking and working out.  Although I feel I have two halves of my life, I try to maintain a balance between them and not let crossdressing dominate my life, despite what my website suggests.  Balance is important especially when you are married.

Balance with anything in life is tricky, especially to crossdressers who are newly out to their significant others.  When we come out to someone, especially our partners, it can go many different ways.  Sometimes our partners are willing to see how crossdressing will affect their relationship and will allow us to wear panties or dress at home or set boundaries.  Many relationships are damaged when limits or boundaries are broken.  Crossdressing alone usually doesn’t lead to a broken relationship.  I hear from many t-girls that their relationship was damaged when they violated the boundaries their wives set, such as being asked to not post pictures online or leave the house.  Lying to your significant other, whether about crossdressing or anything else never helps a relationship.  If a crossdresser has a supportive partner, it is so easy for us to just go from zero to sixty with this.  All of a sudden our drawers are filled with lingerie and our closets have dozens of dresses in them.  This can lead our partners into thinking where will this end and wondering what they have gotten themselves into.

Usually a crossdresser gets one chance to bring this part of us into a relationship.  If we let this part of us dominate our lives or overwhelm our partners, it can lead to some very hurt feelings.  So, we especially need to keep balance in mind because it is not fair to our partners or significant others or wives.

I will take this moment to remind all of us that if you are not married, please, please, please tell your partner about this part of you before you do get married.  It is not fair to spring this on them after you are wed.  I fully believe in putting all cards on the table before you commit to each other.

Anyway, balance.

I have a friend who loves football.  He met a girl a few years ago who also loved football.  He thought he hit the jackpot.  She loved watching the games, loved tailgating, wore her jersey proudly and knew as much about the teams as he did.  They met and fell in love over a shared interest they were both passionate about.  He was thrilled he found someone who supported his hobby.

After a while, football really took over his life.  Whenever a game was on, he’d watch it.  All weekend he’d sit in front of the television watching sports.  He’d go to the home games, he’d go to Fantasy Football drafts, he lived and breathed football.  It was all he talked about.  His wife’s interest, however, didn’t keep up with his.  It got to the point where she was exhausted by it.  It dominated their relationship.  Everything was centered around the game.  They’d fight about it, she was frustrated by how this took over their life and she was simply overwhelmed by it.  Although she loved football, she grew weary of it and hated that she lost her husband to something.

He on the other hand was confused by how she had changed.  He thought she was into football and thought she was supportive of his passion for it.  Unfortunately he let it dominate their lives.  It was all he talked about, all he watched, all he did.

Having a supportive significant other is a wonderful thing.  Whether they are supportive of a hobby, a job, or crossdressing.  The thing we all need to remember is that we can’t let anything take over our relationship.  When many of us come out to our wives, we find it hard to talk about anything else.  I was careful not to let this overwhelm my wife with this side of me.  I tried not to talk about it constantly.  Sometimes it was hard and sometimes I wasn’t paying as much attention to her as I should have and didn’t pick up on her thoughts and feelings.  Through honesty and communication we found a very balanced life when it came to my crossdressing.

Love, Hannah