Vanessa's Transgender Experience

Vanessa Law shares her experience as a 30 year old transgender girl. Come join in her joys of crossdressing, relationship advice and ponderings on how being transgendered has forever altered her life.

My Most Embarrassing Crossdressing Moment

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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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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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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Going Out Crossdressed For The First Time

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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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Sometimes It’s Just Bad Service

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Crossdressing Bliss In A Pedicure

My wife and I had a wonderful day planned today. We were going to sleep in, have a late breakfast and then head to the city for facials. After a relaxing hour being pampered we had a pedicure booked at a fancy salon and then dinner together. Truly a luxurious day spent with the person I love the most.

Except it didn’t all quite work out as planned…

The facials were a fabulous hour of stress relief and beauty (and all for just $70 for both of us! I love the Greenwood Academy). My wife has sensitive skin, and had a mild reaction to the moisturizer they used. It was nothing a few cold compresses and suitably soothing potions couldn’t cure, but we had our pedicures booked across town and after the hastily applied first aid we ended up with less than 20 minutes to get there.

However, luck was on our side even if the traffics gods weren’t. We made it to Gene Juarez (the fancy salon we had picked today) right on time only to wander into a chaotic mess.

Gene Juarez = High Prices and Terrible Service

There was noone at the counter checking people in, so we stood around awkwardly wondering whether we should stand in the checkout line to check in. Eventually someone arrived to help us, and we were told that we didn’t have an appointment. At this point if I had made the booking I would begin to doubt myself, ‘Perhaps I booked for the wrong day?’ However, my wife made the booking, and she is nothing if not thorough and fastidious.

The clerk spent a few minutes trying to find us on the computer, enlisted help from his manager and asked us to spell our names three or four times –  no luck. After this revelation they then proceeded to blame us – ‘perhaps you booked at a different store?’, ‘perhaps you booked for a different day?’. They showed no concern for the fact that we’d arrived for an appointment that now no longer existed. They didn’t even offer to help by trying to find us later appointments or shuffling things around.

If things had concluded more positively I would probably write the whole experience off to a computer glitch or a quirk of fate. Sometimes things happen. The utter disdain the staff of Gene Juarez showed us has prompted me to share a strong recommendation with you: don’t go to Gene Juarez. Their prices are very high (more than $60 for a pedicure?!), the service we experienced is terrible and it looks like we’re not the only ones saying so. Find a local independent salon to support. I’ve found a wonderful hairdresser and electrologist who don’t work at any of the big chain stores. There’s something special about building a relationship with them over many years, rather than being treated like cattle with a credit card.

Sometimes Bad Service Has Nothing To Do With Crossdressing

When I’m dressed I can be overly sensitive to what people say and how they look at me. Sometimes I wonder if the service is less than pleasant because they’ve seen through my feminine disguise and are subtly sharing their disapproval. Today my wife and I were together, as normal as any couple could be. This experience has helped me look on my misgivings in a new, more positive light. Sometimes bad service has nothing to do with crossdressing. Sometimes it’s just bad service.

Here’s hoping your spa experience is more beautiful and relaxing than ours turned out to be.

Hugs,
Vanessa

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Crossdressing Again After A Brief Intermission

Time doesn’t just fly when you’re having fun, it spreads it’s wings when you’re busy, work or play. Now I’d like to say that I spent the last week in absence crossdressing and perfecting new feminine techniques to share with you, but alas I only did that for a few days :)

I spent most of my time working on some exciting improvements that will be coming soon to Crossdresser Heaven. Stay tuned, I’ll take the wraps off them in the next week or two.

This was a brief crossdressing intermission for Crossdresser Heaven, and if anything I know that crossdressers understand those brief or long periods between your feminine expression. Thanks to all the ladies who recently submitted Crossdressing Success Stories, or sent me email – I’m working to catch up over the next week or two, you should hear from me soon.

A Pause in Your Crossdressing?

Crossdressers purge at their peril!

Crossdressers purge at their peril!

We take a breather from crossdressing for many reasons. For some the summer months are so filled with family activities that it’s hard to find some feminine time. Others may be intimidated by the more revealing summer styles (more on this in a future post…). Perhaps it’s the ritual purge performed in search of a cure for crossdressing, or the natural waxing and waning in the desire to crossdress.

Whatever your reason, I’m willing to bet that you’ve spent some period of time not crossdressing – not even thinking about it. As strange as it sounds, perhaps you’ve even felt guilty about not crossdressing. You’ve thought to yourself, ‘if I don’t feel like crossdressing now, perhaps it really is just a phase I’m going through?’.

There’s nothing wrong with a brief respite from crossdressing as long as you don’t feel forced or coerced into it. And trust me, there’s nothing quite like an overactive sense of shame and guilt to force you into an unwilling crossdressing vacation.

Have you taken a break from crossdressing recently? Why did you do it?

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Be Encouraged By What You Learn

Be Encouraged by What You Learn Crossdressing

Be Encouraged by What You Learn Crossdressing

At the start of every yoga class we’re urged to set an intention for the practice. The intention is set as something to grasp onto when the practice gets tough. When your muscles are aching and sweat is dripping down your forehead you can come back to your intention for strength and motivation.

Recently I made my second trip to an advanced yoga practice. The first one had been a miserable experience. Overwhelmed and unable to follow along with the instructor I spent most of the class lying on my mat. It had taken a few months before I braved the advanced class again, yet the memory of my failure was still in my mind.

I knew that the class was going to be just as hard, and I would feel overwhelmed, tired and frustrated. So I chose my intention carefully. This practice I was going to focus on one thought:

Be Encouraged By What You Learn

Be encouraged by learning, not by perfection. Even if I try a pose and fail, my muscles become stronger, I learn more about the technique. Even if I’m too tired to stand up, I watch others and learn from them.

Throughout the practice I felt encouraged by my frustrations. I felt encouraged when I couldn’t do a pose. I felt encouraged when my muscles ached and my body quivered. I felt encouraged by what I was learning in every moment.

Crossdress and Be Encouraged

Sometimes crossdressing is like the most difficult yoga practice. You’re frustrated because you can’t seem to get your makeup right. Your clothes don’t fit properly, you struggle to walk in heels and you ladder your stockings. Every step you take as a crossdresser seems manly, clumsy and awkward. You may even have people laugh at you, or stare with intense interest. Your feet might be hurting, sweat ruining your makeup and the teller calls you, ‘sir’.

Despite being excited at the prospect of a wonderful day spent en femme you end your day in despair. Cursing your transgendered misfortune.

But Be Encouraged By What You Learn

It’s easy to get caught in the perfection trap. Always striving for perfect, yet never achieving it. Each failure chipping away at your pride until you barely feel like wearing anything at all. Don’t let your own judgments stop you from crossdressing.

Wear those clothes, do your makeup, put on that wig. Do your feminine best, and be encouraged by what you learn. Even if all you learn is how ill suited that red sweater is for your figure, have fun being awfully gorgeous.

We’re all just practicing our femininity, some of us have been at it a while longer, that’s all.

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