Advice and Encouragement

My Most Embarrassing Crossdressing Moment

By Vanessa Law | Published March 9, 2010 | 6 Comments

Have you ever had a moment when you wished your high heels would part the sidewalk beneath your feet just long enough to envelop you? A moment when time seemed to draw out like the never ending strands of your favorite silk blouse, and all you could hear was a wave of laughter slowly washing over you? It’s perhaps at times like this you wished, hoped, dared to believe that crossdressing would forever remain in your past.

I’ve been quite fortunate in my crossdressing career (my transgendered life?) to have had few moments of outright crossdressing embarrassment. Most people I meet in public are either friendlier than usual, or don’t notice me as they walk by in their own world. A few people share a look of dawning surprise on their face – one which is usually soothed by my friendly smile. At least I think it’s my smile – perhaps they figure I’m a crazy woman and don’t want to attract too much of my attention :)

My Most Poignant Crossdressing Embarrassment

There is, however, one moment which sticks out in my mind and still makes me blush. Though I find I blush more so at my reaction than the situation itself. One evening many years ago I decided – quite boldly – to apply a coat of nail polish before venturing out as a guy. Having once attended boy scouts, I knew to always ‘Be Prepared’ and “wisely” wore a baggy jacket with plenty of hand-hiding room. Perfect for concealing my painted nails, should someone choose to notice them.

I spent a nervous fifteen minutes browsing Circuit City, where I’m sure I spent a good three minutes with my hands courageously not shoved deep into my pockets. After mustering all the nerve left within me I took my purchase to the cashier. Just as I was paying a man behind me exclaimed to his friend in a rich Southern accent, “Hey, there’s one of them crossdressers”.

I was busted, and couldn’t very well finish paying with my hands in my pockets. I smiled nervously at the cashier, and felt my vision narrow as I tried fervently to hide in plain sight from the two men next in line. Time seemed to stand in awkward stillness as I rushed to finish paying and get out of the store. The cashier seemed to be embarrassed as well, as if somehow my crossdressing embarrassment were contagious.

Eventually I made it out the store and into my car. Apart from a few moments of furious blushing, nothing bad happened at all. I sometimes wish I could go back in time to that moment and do it differently. I imagine myself turning to the gentlemen, and with a warm smile extending my hand and saying, “Pleased to meet you.”


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The Last Crossdressing Poll

Wow! Almost 3000 lovely ladies answered the last crossdressing poll. Under-dressing was the overwhelming favorite for expressing your feminine side while dressed ‘en homme’. From panties to stockings, a cami or bra hidden underneath an otherwise normal exterior you ladies enjoy your well concealed feminine graces.

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Peace At Last

By Vanessa Law | Published January 28, 2010 | 7 Comments

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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Going Out Crossdressed For The First Time (Again)

By Vanessa Law | Published January 21, 2010 | 10 Comments

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.

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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

By Vanessa Law | Published January 19, 2010 | 12 Comments
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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

By Vanessa Law | Published January 14, 2010 | Leave a comment

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.

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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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Crossdressing in the New Year

By Vanessa Law | Published January 9, 2010 | 8 Comments

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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Going Out Crossdressed For The First Time

By Vanessa Law | Published December 20, 2009 | 51 Comments
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Were you nervous the first time you crossdressed?

I’ll never forget my first time going out crossdressed, even though it’s almost eight years ago now. I had been dressing at home for many, many years and underdressing as often as I could, but I had never been out ‘en-femme’ before. A few weeks earlier I had joined a local crossdressing group and  had finally plucked up the courage to attend a Tri-Ess meeting.

In my infinite wisdom I thought it would be a good idea to go out crossdressed for the first time. I was conservative in my femininity – I wore a blue blouse over some slightly feminine jeans with a bra for my breastforms and just a dash of makeup. With trepidation I exited my apartment, eager to quickly make the trip down two flights of stairs to my car without being seen. Then as I step foot into the parking lot I’m confronted by

Cops, everywhere – and they’re after crossdressers!

And I’m dressed. They’ll notice my boobs and my feminine blouse. Oh God! Now I’ve gone and done it I knew I shouldn’t have dared to venture out crossdressed. I almost died of embarrassment right there. I knew I was going to get into trouble, or at least a stern rebuke.

As it turns out, the police officer wasn’t outside my apartment waiting for crossdressers and he didn’t pay me much mind. I got into my car without any problems, and was off to my first Tri-Ess meeting.

Over exaggerated fear of what will likely never happen. That’s what I experienced the first time I went out crossdressed, and I have a hunch that I’m not alone. Our worst fears rarely come to pass yet we spend so long dwelling on them. It’s only when we’re out in the moment that the fear can be replaced with the joy of expressing one’s feminine self.

Going Out Crossdressed For the First Time

A few weeks ago I was blessed to take my good friend Vicki on her first crossdressing expedition into the cisgender world. She had visited the Emerald City (a local transgender club in Seattle) before, but leaving the safety of an understanding transgender group was new for her. We started out the afternoon with lunch at Chinese restaurant that we had all to ourselves, and despite some interesting smiles from our hosts it was a great way to ease into crossdressing in public.

Vicki truly showed mastery of her nerves when she suggested a quick trip to the mall together. Dining in a deserted restaurant is one thing, walking through a crowded mall is quite another. It was wonderful to see the sense of joy and accomplishment in her face as she took a proud step forward into the world as her feminine persona.

What was you first time going out crossdressed like? Was it nerve wracking, exciting, joyous, liberating or something else entirely? I’d love to hear, comment and let me know.

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