Crossdresser Heaven

Going Out Crossdressed For The First Time (Again)

A few weeks ago I shared my experience going out crossdressed for the first time. There are few things that get the adrenaline pumping, the voice quavering and the nerves tingling in quite the same way. I also shared the story about Vicki’s first time out in public outside of transgender meets. Today, Vicki shares her perspective on the outing that day.

If you’ve had a crossdressing success – perhaps it’s your first time out in public, or the first time attending a transgender event I’d love to hear about it. Take a moment to share the story of your first time crossdressed in public.

Vicki’s First Time Crossdressed in Public

This is my follow-up to Vanessa’s post about my first time out in a real public place cross-dressed. It was a mix of apprehension, followed by some moments of self consciousness, but overwhelmingly colored by a sense of accomplishment and joy. Vanessa remarks that her observation of the look on my face was far exceeded by what I was feeling inside. The biggest lesson I learned though was get a sensible pair of heels if one is going to go mall walking. What I hate to admit is that after all the feelings of apprehension and fear, once I was there, I wanted it to keep on going, but my vanity for 5” heels forced us back to the car and finally to home.

I suppose that I may not even have made it this far if it were not for my girlfriend who I have mentioned before is so supportive of and handy to my expression of my femme side. Without her makeup and fashion sense it is hard to believe I would have ever been presentable enough to do it on my own, but more importantly her moral encouragement is truly what has finally gotten me out the door and into the world. The morning of the intended venture I must have talked myself out of it a hundred times, and came very close to letting Vanessa know that I had once more chickened out. My lame excuse had ultimately come down to getting past the neighbors. What the response was, so what,. She told me to remember that my ultimate goal is to present a positive and teaching presence to a world that looks at us strangely. If I can’t get off the block because I’m afraid of what people think then I’m only lying to myself about my motives. Plus, she said, nobody is going to be looking out the window in all likelihood anyway.

So the last excuse was gone and all there was to do was get to it. Madeup, tastefully, and I’ve let my hair grow a little so a short upswept do. We decided that a pair of jeans, a nice blouse with my lacy things under, and a pair of my more comfortable boots would do. I met Vanessa at her car and off we went. Lunch at a nice Chinese restaurant and to be honest once I was inside I felt more and more comfortable. We ordered, aye, and chatted, and for the most part were left to ourselves and as far as I could tell, were not being stared at. As my girlfriend has told me in past attempts to go out, they don’t know me from Adam or Eve anyway. We paid our bills, we had to ask for separate checks and then off to the ladies. I boldly went and used the ladies and then off to the mall.

When Vanessa suggested the mall, it seemed as natural as anything to say yes. I think just being out was giving me little shots of confidence. This of course would be more public, it was the Saturday after Thanksgiving after all, But we parked at Northgate, walked up to the doors, passing many people on the way. I was a little self conscious, but I also felt very ecstatic about what we were doing. By the way, Vanessa carries herself with an air of confidence and an attitude of I belong here too that is easy to feed off and say what the heck. Well, we strolled up one side and down the other, if people were staring I tried not to notice, we browsed at a couple of kiosks, window shopped a couple of stores, went into Macy’s and browsed a couple of departments. Back out and into a bath goods store. We spent some time in there and eventually I allowed myself to detach from Vanessa’s side and allow her to do her own browsing and I did my own. As I was looking at a neat little massage tool, one of the female clerks came up to me and did a very good job of customer service. Alas, I was short of cash in my gf’s little LV purse, but I felt another surge of excitement that I was actually doing this. Vanessa was paying for something back at the check stand and I made my way back to meet up with her once more. We made some small talk with the checker and then we are off and back out on the mall. I was feeling very proud, but my feet at this point were killing me. As much as I wished to continue on, my gosh, I felt like I wished the day would go on forever, but my feet were killing me and we had a long way back to the car.

Well, to bring this to a close, I am hooked. I have not been out in public again yet, but the fears that kept me from even getting out the door are past. I am looking forward to my next venture with Vanessa, with my girlfriend, or just by myself. Not everyone can do it, trust me, I stayed inside for a lot of years, but if you feel strongly about it, then by all means do so. One of my problems has always been that I like to dress as femininely as possible, but as Vanessa and my girlfriend have pointed out, look at the women that are out shopping, sure a nice skirt and heels will work, but not that black latex mini and the platform sandals. Choose something feminine but subtle, by all means go with a friend if you are so fortunate to have someone like Vanessa about. (God bless you V) But most of all, act like you belong. I admit, Seattle is a pretty open minded city so I am lucky there too, but if you act as if you were strolling in male mode, which means YOU aren’t thinking about what you are wearing, you’ve done half the battle. Good luck and good dressing to all you wonderful gals, we are a special community.


Are you looking for confidence stepping out? With this crossdressing guide you’ll present your best crossdressed foot forward every time!

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A Teenage Crossdresser

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Teenagers and Crossdressing - too much confusion?

Every few weeks I get an email from a teenager who is struggling with crossdressing. They’re looking for advice, sometimes sure of their transgender identity, other times coming to terms with the alien desire to wear clothes of the opposite sex. I think it’s wonderful that the Internet allows us to explore the transgender demons inside us without letting on that we’re anything but normal. Yet in many ways I’m conflicted about replying, because being a teenager and knowing about crossdressing is not something I can relate to.

Even though I’ve had the strange desire to wear woman’s clothes since I was four years old, I didn’t have a name or anyone to reach out to when I was a teenager. So I have limited experience in receiving advice early on in life, and then looking retrospectively to see how helpful that advice was.

I’ll share some of my thoughts on the most common questions I’ve received from teenage crossdressers, and I encourage you to review the excellent resources provided for transgender youth by tsroadmap.com

I like to wear woman’s clothes, am I a crossdresser? Maybe, maybe not. During the teenage years there is a lot going on as our bodies change and mature. Hormones are raging, as we begin to fully form our identity separate from our parents and family. During this stage of life things which seem vitally important today may not seem so important three years from now. We go through phases that seem to leave as quickly as they came.

By no means am I saying that your desire to wear woman’s clothing, or your perceived identity as a member of the fairer sex is just a phase. Rather, you need to carefully examine your own feelings in light of the dramatic changes happening in your life. It may very well be that you are a crossdresser, and have been blessed to realize this so early in life. Only you know for certain whether you’re a crossdresser, and it’s okay to take a few months to figure it out.

Should I tell me parents? That’s a tricky one. I haven’t told my parents yet, even though I suspect my mom knew all along. There are few people in the world who care more about you than your parents. They want what is best for you, and can be your greatest allies as you explore your feminine side. Your parents could also end up harming your path to self discovery – a well intentioned parent may seek to cure you for fear of your future, or may have religious or moral objections to who you are that lends itself to destructive behavior. My advice would be to find another adult you feel safe confiding in. Perhaps it’s an aunt you have a good relationship with, or a school counselor - someone who is able to place your needs ahead of the need to tell your parents without your consent. There is no guarantee that this person will have all the answers, or even any good answers, but talking with someone will help you figure out things for yourself as well.

Am I gay? Maybe, maybe not. Just because you enjoy wearing woman’s clothes does not mean you’re gay. Sexual preference (do you like boys or girls) and gender identity (do I identify as a boy or girl) are separate. In fact many crossdressers are heterosexual men who identify as male, but enjoy wearing woman’s clothes on occasion.

How can I look better as a woman? If you’re friends with a girl you trust, a great way to perfect your look is to practice and get her feedback. She’s learning just like you are, and it can be a fun way to bond with someone. You’ll also find many crossdressing tips right here on Crossdresser Heaven.

Where do you hide your feminine things? It’s hard to find a place at home that is truly private. Even seemingly safe hiding places such as under your bed, in a suitcase full of regular clothes at the bottom of your closet are susceptible to accidental discovery (the day your mom decides to do laundry and turn over your bed, or go through old clothes looking for something to give to goodwill). The best hiding place is out in the open after your parents know, but this isn’t always an option. A pile of ‘your stuff’ is usually a great hiding place – the box that holds your CD collection, or in a cupboard behind school text books. Look for a place that someone else is unlikely to have reason to go.

How can I remove makeup before my parents get home? I remember the first time I tried on my mother’s lipstick I spent 30 minutes furiously scrubbing to try and get it off before she got back home. All the furious scrubbing made blood rush to my lips, so they looked red even though the lipstick was long gone. The best way to remove makeup is with makeup remover. Your mom probably has some, but if you’re unsure you can buy eye makeup remover at any drug store. This will remove eye shadow, mascara, and can even be used to take off lipstick. Most blush and foundation should come off with a good face wash.

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My Crossdressing Story: From Frustration to Acceptance

Dear Readers,

It has been a few weeks since I shared a crossdressing success story. With the festive season and rush of the “first week back at work” behind me, I’m back into the swing of things. This week’s story is from an avid reader of Crossdresser Heaven who contributes so much back to the community through her thoughtful and loving comments.

If you’ve got a story of crossdressing success, however small, take a moment to share your crossdressing story. Or once you’ve met Ragina, continue reading about Randi’s crossdressing adventure.

Meet Ragina

My femme name is Ragina, and I live in Georgia with my wife of 20 years. I have been crossdressing off and on since early childhood, but have been regularly dressing for about thirty years or so.

Crossdressing Success Story

My first recolection of crossdressing was many years ago when as a youngster I would have to accompany my mother to choir practice at church because my dad traveled a lot for his job at the time. During those years, women still wore gloves to church, and of course , someone would accidently leave a pair . They found thier way to the lost and found box, where they would sooner or later be claimed. I don’t know what attracted me to those pretty white gloves, but they called to me.

Nervously, I grabbed several pairs and hiding myself in a closet (ha,ha,), I tried them on. The feeling was like no other feeling I had ever had, and I pocketed a couple pairs to take home. This continued for a couple of years. Then I happened to find a pair of Mom’s stockings balled up in the trash and rescued them out of curiousity. I knew enough that they went on the legs, so , locking myself in my room, I tried them on and wow, what a feeling! So soft and smooth on my legs.

So that set in motion my pattern of crossdressing for a time. Of course I became more and more curious of the other things that women wore, bras,panties slips,and so on,and vowed somehow to get these garments for myself. By this time, I was in junior high school and all the girls were well developed. I was taking music lessons at the time and had to wait after school for my lesson. Somehow, I accidently wound up finding a girls clothes, and lo and behold were all the things that I’d desired.

I stuffed them all into my bookbag and took them home. This one act, along with trying those clothes on galvanized my love of all things feminine. I continued to crossdress in bits and pieces from then on, eventually being able to purchace clothes on my own. Of course, all this was done in secret, as Mom wouldn’ understand at all. Little did I know that she already knew.

Eventually I married and started a family, still dressing in secret. This first marriage didn’t last, not because of my crossdressing. I relocated here courtesy of the military, met and married my current wife, being careful to let her in on my secret hobby. At first, she had a very hard time understanding and accepting my feminine side, but as time went on,with tenderness and patience on my part, she grew to accept me as I am.

I now have the best of both worlds, a wife who loves the man that I am and a wonderful girlfriend to hang out with. Life doesn’t get much better than this. To all my sisters out there, be patient and loving, the person you are is wonderful and worth loving.


Ragina, thank you for your beautiful story – truly a crossdressing success! If any readers are struggling to find their own crossdressing success I highly recommend Peggy Rudd’s book, My Husband Wears My Clothes.

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Your Chance At Crossdressing Fame

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Your chance at crossdressing fame

I’m excited to share this opportunity with the lovely ladies of Crossdresser Heaven. It’s your chance at crossdressing fame, but more importantly, you’ll be able to impact public perception of crossdressing in a positive way. (And you’ll get some fabulous professional photos too!)

Kate, a journalist for More! (A UK woman’s glossy magazine) contacted me last week. She is writing a feature on modern crossdressing, and is looking to interview a young couple who have overcome crossdressing. In her words:

I’m after the story of a woman in her twenties whose boyfriend or husband dresses in women’s clothes and they’re both fine with it. The feature would be insightful and positive, rather than sensationalist and would look at a young couple who have dealt with cross dressing in a loving and supportive way. There would be a full professional photo shoot involved and possibly a fee. If you can help in any way, that would be fantastic

If you’re interested, you can contact Kate at katebc76@yahoo.co.uk. It’s a great opportunity for ladies in the UK, but Kate tells me she has access to photographers in the US as well – so don’t let distance prevent you from volunteering.

As a quick note, I’m in no way affiliated with More!, please use your best judgement when meeting people in regards to safety, and before paying any fees.

Would You Share Your Crossdressing in a Magazine Story?

Even if you don’t qualify for Kate’s story, I’m interested:


Would You Share Your Crossdressing in a Magazine Article?

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A Time of Renewal

Dear readers,

The new year hearkens a time when we look forward, where old things are reexamined and new things are planned. Vicki’s inspiration for this week invites us into the beauty that awaits in 2010. Remember, do you what you love, even if you love wearing woman’s clothing.

“For behold I create a new heavens and a new earth, and the former things shall not be remembered or come into mind.” Isaiah 65:17

The New Year is to most of us a time to look ahead to the future and promise that in the coming year we will do better at whatever it is we decide we need to be better at. “Should Auld Acquaintance Be Forgot and Never Brought to Mind”, that sort of thing which is so accurately reflected in the verse from Isaiah. Too often though, the old habits, old ways of thinking keep pulling us back I am no different than the rest, but events during this last holiday season have put this verse at the front of my thinking for the coming year, and once again I make promises that I already know will be hard to keep, but armed with some new insight from Isaiah, perhaps I will be more successful than before.

One of the biggest things that hang over me, especially at this time of year is how far am I willing to go to put myself on the line as a TG person. Indeed, how committed am I to maintaining a more regular schedule in terms of just writing these inspirations. It’s not from a lack of real inspiration as much as it is old habits convincing me personally that even this is a trivial exercise and there is so much more to be gained by surfing the net for useless information that I’ll never need again. A year ago I came across Crossdresser Heaven and resolved that I would finally listen to what I think God had been saying to me and step out in a positive and visible way in order to be a spokesperson for the TG and the larger LGBTG community. Well, this column was a start, and I did finally venture out into public, but the goals I had set last year kept being pushed off to the distant future. Habits, ways of thinking, and fears kept cropping up and making “good” excuses for NOT doing a column, not attending a LGBTG event at a local church, even in drab, not following up on other opportunities that came my way,

The holidays played a part in this new awakening to me. My relationship with my mother and siblings had taken a hit when I divorced my first wife and settled in with my girlfriend Molly. Four years later things have not improved though in my mind I had hoped for a Christmas Miracle. It is painful to me that my Lutheran family seems so hard hearted to the woman I love so deeply and who makes me happier than anyone ever has done in my life. She is my soul mate and it is painful for me that my family, mother especially, cannot allow themselves to accept this “Jezebel” and see beyond the event to the heart she has inside. Unfortunately a pleasant post Christmas visit, (minus the love of my life), was spoiled by a simple comment by mom that pretty much shattered my hopes for a full reconciliation anytime soon.

I was stung, not from a sense of feeling guilt, for the comment mom made was sorely out of proportion and context to a perceived slight. I realized that forgiveness was not forthcoming, for Molly, and by extension, for me. I struggled a day or two with this information until the words from Isaiah crept up on my e-mail Tuesday morning. God promises a new way of looking and seeing the world. Perhaps my blood relations cannot see it yet, but there is hope. But for my part, I need to let go of that hurt first and move on into the next phase of God’s life plan for me.

I can already hear many of you saying; well what does this have to do with cross dressing for goodness sake? A couple things, first any illusion of coming out to my family any time soon , before I make certain other steps in this lifestyle is not going to happen. Imagine the fireworks over that one, not only did he divorce his wife, he runs around in Jezebel’s clothes. But it doesn’t matter. To hold onto the past restricts my step to the future. What was in my mind an excuse became a roadblock. Not that I will forget mom entirely, I am her son, but I cannot let her opinion of me and my desire to “make it right” prevent me from moving ahead in a life affirming, love filled way. There is the second part of the lesson for us as cross dressers. No matter where you find yourself on the journey, look to the words of Isaiah. Old ways of thinking and behaving are out, God has established a new heaven on earth and we are assured of that in Christ. To all my sisters then, a Happy New Year, one filled with positive steps ahead, be it in acceptance of yourself as God accepts you, or in steps out into the world, to find where that self fits in , but most importantly to find the work that God wants you to give as a full measure of that self that is wholly you..

2 Comments | Posted in Vicki's Inspirations for Crossdressing Christians | Tagged | Trackback URL.

Crossdressing in the New Year

I figure that it’s still New Year’s through the first week of work, and I know a few unfortunate folks are working this Saturday – so in the nick of time, ‘Happy New Year!’

Do you make New Year’s resolutions? Do you have any that have survived the first week of the new year? :)

I’m the kind of person who likes to set New Year’s resolutions. Though I call them goals and hope that this renaming trick will give me an edge in actually attaining some of them, because as you know – resolutions are made to be broken, but goals are made to be achieved. At least that’s the theory, but my rebranded ‘Goals’ contain a few familiar faces.

Lose Weight. Check. I didn’t lose much last year, but I’m going to beat myself up all of this year until I make some more progress. Apart from all the health benefits to losing weight, I’ll feel good about myself and look better in the new dress I bought for Christmas.

Follow a budget. Check. I seem to have better luck at this goal than losing weight, which is surprising given how hard it is for me not to buy something.

This year was unique though, since I included a few transgender new year’s resolutions on my list. Over the last few years I’ve reached a point where I don’t feel as much apprehension and guilt as I used to and every new step along my transgender journey brings me joy.

My Transgender New Year’s Resolutions

Finish electrolysis: Sometimes it feels as though I’ve spent more time removing hair than I’ve spent crossdressed. So far I’ve logged almost 40 hours of laser hair removal, and another 30 hours of electrolysis. It’s probably the most painfully expensive fulfillment I’ve experienced, and it’s worth every grimace. My goal this year is to finally finish electrolysis for my facial hair. Having a baby smooth face and never needing to shave again are tantalizing indeed. I know that I’ll need to steel my resolve as I get closer to finishing. It’s easier to justify skipping a session when there are just a few blond hairs left :)

Make more (in real life) transgender friends: I’ve met some wonderful ladies through Crossdresser Heaven, but most of my transgender friends are virtual. I’ve also met a few fabulous girls in the real world (hi Vicki!), this year I want to make a few more “offline” transgender friends. This means, in part, that I need to get out to more transgender events, and be less self conscious going out when dressed – both things I’m looking forward to!

Attend a transgender conference: It’s hard to imagine that just a few years ago I would shudder at the thought of going to a transgender conference. I’m excited about all the things I’ll learn, and the new people I’ll meet in a transgender friendly environment. Since it’s local, I’m planning to attend Espirit this year. I’ll let you know closer to the date whether I’ll be going, it would be great to meet some of my lovely readers.

Begin building my feminine identity: Of all the goals I’ve set for 2010, this one is perhaps the most nebulous for me. I realize that when I am Vanessa a different side of my personality emerges – a person I enjoy being, but don’t yet fully understand. I have to thank Petra for bringing such ponderings to the forefront of my mind. This goal could perhaps be titled ‘Figure out whether I want to transition’, but my aim at the end of 2010 is not to come out with a single answer. Rather, by the end of this year I want to grow into the kind of person who can answer this question. Coming up with an answer to the ‘Do I want to transition?’ question may still take many months or years after 2010.

I hope 2010 has begun well for you! Do comment and let me know what your resolutions are for 2010, and if you don’t make resolutions let us know why not.

Onward into the brave unknown!

-Vanessa

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Merry Christmas

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Merry Christmas from Crossdresser Heaven

Merry Christmas to all the readers of Crossdresser Heaven. May your Christmas be filled with the joy of special moments and the love of special people.

With blessings to you and those you hold dear.

-Vanessa

Vicki has written some of her thoughts this Christmas, which I’d like to share with you as you celebrate the festive season.

Crossdressing, Christmas Time and God’s Love

Wow, what a year this has been. One year ago today, just home from work, snowbound on Christmas Eve, I chanced upon this wonderful little site called Crossdresser Heaven. It was just what I’d been looking for, a place to talk about Crossdressing, but also a place where one could find some good Christian support for this little hobby, or maybe better to say, lifestyle of ours. It may have been percolating in my mind a bit, but I still hadn’t figured out a way to get the thoughts and ideas I had about my feminine side and it’s relation to my spiritual side out and onto paper, though I knew I had to somehow. Finally a place to discuss it and perhaps rummage around in my “closet”, and a few other closets as well to figure out how it all fit together.

Little did I know that I’d be contributing, much less did I know that before the year has elapsed I’d be taking my first steps in the real world with our lovely and talented hostess Vanessa.

We are asked at this time of year though to step back a moment, and focus on the reason for Christmas. Trust me it sometimes is hard to find much of anything in Scripture about crossdressing, and in the one place it is mentioned it is regarded as an abomination in God’s eyes. Not much hope to go on there is it? But that tends to categorize us as somehow different, and though in society’s eyes we are, the story of the birth of Christ tells us that we are all a part of God’s fallen world, sinful, screwed up, dead in some ways to hope and promise. In God’s eyes there is no differentiation. God looks on the world and sees a place that needs His Saving Grace.

I have many favorite parts of the Christmas story, I love to sit in a hushed church on Christmas Eve and be reminded of the way Christ came into our world to be God among us, Immanuel. There is a special silence that seems to fall on this night that is different than any other. It may simply be that when I leave church, nothing is open and the rest of the world is inside. Not everyone of course, for there are still those that are homeless, in search of a place to lay their heads. And there it is, that part of the tale that connects us intimately with God, or rather connects God intimately with us. For on the night of His birth he too was “homeless”, weary from a long journey, showing up perhaps after everything was closed, they had no place to rest, no place for Mary to give birth but the stable. If God, King of Kings had wanted to establish His special place of birth, to place Himself above us in His Kingdom, he could have done much better. But He didn’t, He chose to be born into a place of squalor, with animals as His bedmates, in a hidden dark corner of a tiny village in the Middle East. He came in humble birth to announce that He is with us to live our experience, not to preach about how we should change who we are, but to say I love you and accept you because I’ve been there, and all I want is for you to love and be loved, by Me, but to also love each other as I have loved you first.

From that birth story we take this message, that God truly is Immanuel, God among us. He has been in the dark corner we have all been in, He has and still to this day experiences our pains as well as our joys. Having been exactly where each of us has been, His only response is to love us. How can He not, for to do so would be to not love Himself.

Peace to all on this Christmas 2009. May you all be Blessed and come to accept the Love God pours out to us all.

Vicki.

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