Crossdresser Heaven

En Femme, In Stealth

Unfortunately we can’t spend every day presenting as our feminine persona. Whether it’s work, family or friends we all have occasion dress as a man. If you’re like me, this can be immensely frustrating. When dressed as a man I feel as though I’m wearing a mask that hides my true self. Yet there are many ways to express your femininity without letting your inner girl run wild.

In this week’s crossdressing poll, I’d love to hear how you express your femininity in stealth. If you have a way not listed below, please take a moment to share – I know that many of the readers would appreciate learning new ways to be the girl inside, even when circumstances don’t allow.


How do you feel more feminine when presenting as a man

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Last Week’s Crossdressing Poll

The results from last week’s early crossdressing valentine poll are in. Almost half of you gorgeous ladies take the opportunity on Valentine’s day to buy yourself some sexy lingerie, while for a good number Valentine’s day is about spending a romantic evening with the person you love. Whatever you choose to do on this hallmark holiday – do it with all your heart and look fabulous!

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Peace At Last

Dear readers, I think we all have something we can learn from Anne’s crossdressing success story this week. I’m particularly impressed by the patience, love and consideration with which Anne shares her crossdressing with her wife. Credit is also due to her lovely wife – she gave Anne the opportunity to share, was open enough to learn more about crossdressing, and accepts Anne for who she is. Truly this story is like oil on the troubled waters of our souls.

If you would like to share your crossdressing success story, please take a moment and submit your story here: http://www.crossdresserheaven.com/contact-vanessa/submit-your-crossdressing-success-story/

Meet Anne

I am early 60’s with a wife of 40 years, 3 children and 4 grandchildren. I was raised in a Christian family, spent most of my career in the aviation field, and actually pastored a small church for a few years. I retired 5 years ago and we live in BC, Canada. My interests include golf, boating, biking, gardening and learning more (from your pages as well as books etc) about this crossdressing thing.

Anne’s Crossdressing Success Story

The latest chapter of my life began just over a year ago (Dec 08) when I emerged from the closet (literally, as we have a walk in closet) with a bra on and asked my wife what she thought! We had just finished an evening of sex, and I had probably put on her nightie at some point in the proceedings, as I had done here and there during lovemaking over the 39 years of our marriage. She had always taken it to be just an extra turn on for me and had never really objected to these momentary aberrations on my part.

Little did she know that I had been crossdressing in secret over the previous 6 years or so, and that now I was making a statement about who I really was. She was totally shocked as I began to open up about my desires to wear women’s clothing, as she had barely heard of such a thing before, our family being good Christians where such behaviour would have been viewed as sinful.

But to her credit she listened as I poured out my heart, then she began to ask questions, then listened some more. We talked until dawn, then steadily for the next few days. I brought out my stash of clothes and she watched in amazement as I modelled for her right there in the kitchen. By then we were able to have a laugh or two over the whole business, and both of us began some research into the “condition”. We scoured the internet and bought Peggy Rudd’s book which shed much light on the subject, then to my wife’s great credit she consented to letting me dress while in the house, and to keeping a drawer and some hangers for my “stuff”.

It felt like I had died and gone to heaven and still does as I write this while seated at the kitchen counter dressed in a pale blue skirt over patterned stockings, and white knit top over pink camisole and rather nice, lacy white bra. No makeup or wig at present, and generally I wait until my wife is out of the house before doing all that, as I try to be respectful of her at all times. Sometimes we just know when enough is enough!

I do get out of the house a bit while dressed , but covered. This afternoon it was raining pleasantly, so I put my rainpants and jacket over skirt and top and went for a long walk. What peace was mine as I stopped in the woods to observe the birds, while being very aware of what I was wearing and the effect it had on me.

Who knows where I go from here, but I feel that the freedom my wife has given me to excercise some of my innerself has been a huge blessing. My secret has gone no further than her , and yet we both believe that I am a more open, compassionate person with all the members of our family. Over the years I have been a moody person and even diagnosed with depression, which I felt as a Christian I should have been able to overcome. Since I have been free to dress, whether I actually do or not, I have been of a more even and contented temperament. It seems amazing what a bra and slip can accomplish, and I believe that God might just have been waiting for me to discover that!

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An Early Valentine’s Day Crossdressing Poll

For many men there are few holidays more dreaded than Valentine’s day. Between the prospect of spending the day alone for some, or forgetting and spending the day in the dog box for others one can almost lose the sweet romance. Yet perhaps because of all the Hallmark-hype love, togetherness and the tender touch of your soulmate are just the start. Gifts have become a staple of February 14th – flowers, chocolates, and perhaps even some sexy lingerie are all appropriate, expected or hoped for.

I usually start thinking about Valentine’s day the first week of February, but today my lovely wife surprised me and suggested that Valentine’s day would make for a great poll topic for Crossdresser Heaven. I wonder… do all woman start thinking about this holiday so early? Perhaps for the moment I’m still a man with the soul of a woman.

With this week’s poll you get to tell me: as a crossdressing valentine who buys the panties in your house.


With Valentines day coming up, do you:

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Crossdressing, Haiti and God’s enduring love

Vicki brings us another inspiration for crossdressing Christians inspired by the devastation in Haiti, and the outpouring of love from around the world. Truly, God is there when it is darkest, even though His instrument may look to you and me like a caring person and not a flash of lightening from the sky.

Now there are varieties of gifts, but the same Spirit; and there are varieties of services, but the same Lord; and there are varieties of activities, but it is the same God who activates all of them in everyone. ! Corinthians 12: 4-6

The events in Haiti and some of the negative comments from certain religious and political figures here in the US and elsewhere certainly made me a little uncomfortable with sharing the label Christian. I’ll admit, at the beginning of this crisis, I tried to avoid the images. We’d just finished the season of Christmas and all of a sudden the sick stark reality of the world was trying to rumble back into my conscious. But Pat Robertson’s and Rush Limbaugh’s comments put me in a fighting mood and now I am riveted by the stories, and images emerging from the devastation. A local woman, Molly Hightower, a Catholic woman died in Haiti, trying to help a people already beset by poverty, disease, and suffering. Yet despite this and despite stories from people who have fled, they all seem united in one common thought. Let us catch our breath and then we are going back to help, to rebuild, and to affect lives in a loving and positive way. These people live the message of God. This morning I saw a news clip about how an Israeli rescue team had freed a man trapped since the quake nearly two weeks ago.  What The  rescuer said, when asked about the man’s condition was, “I don’t care, he’s alive.”

People from different walks of life, people with different talents and abilities, all are working to ease the hurt. That is God’s response, not one of turning His back, or rendering the destruction in the first place to punish an evil people and nation. So, where is the connection to this, and cross dressing life? Sisters, God gave us a gift. Though many may see it as sinful or an aberration, it is a gift that God gave and if we approach it that way, and live our lives that way, then the fruits of that gift can blossom with the aid of the Spirit. Those who look on us as sick or aberrant are missing the point that, for me at least, when I embrace my feminine side and let go of the macho mask I try to put up, my creative spirit, my empathetic spirit, my loving spirit is strengthened. But most importantly, I find myself actually coming closer to God. Rather than God turning from me because I like to express a feminine side of my personality, He seems to be celebrating with me that I have discovered He made me this way, and He has a plan to use me in the world.

At 54, I am still trying to discover exactly what God has in mind for me. But for the first time, I feel like I am finally on a path to discovering what it is. My heart aches for the people of Haiti right now, I want to do something other than sit with tears in my eyes as the images continue to play on my tv screen. A donation however small does not seem to be enough. Then I realize that perhaps it is enough, that there are talented people who DO belong at the side of the Haitian people. Their skills and spirit are well suited to the task at hand. Maybe it is enough to pray and do what little I can; God has something else in mind for me. God has something in mind for you too. God made you this way for a very good reason. Knowing that at this point may be enough, but be open to God’s call when it does come. And if it be in a skirt and blouse that He asks you to employ your talents, then know that it was always a part of His plan.

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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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