Archives: January 2009

Linda's Crossdressing Success Story – From Hell to Heaven

Crossdressing Success Stories are real stories from crossdressers who have succeeded in an aspect of femininity. Their success may be personal or public, but the lifelong impact is unquestionable. Each step on the way to success builds confidence until finally we can comfortably live as who we are.

Share Your Crossdressing Success Story

If you would like to share your crossdressing success story, please email me at vanessalaw@crossdresserheaven.com and let me know you’d like me to share with others. Please include:

  • Your femme name
  • A brief introduction (1-2 sentences about where you live, how old you are and such)
  • Your story (if you go over 700 words I’m going to edit you down :) )
  • Optional – A photo of you (no nudity please)

I’ll post your story on Crossdresser Heaven within a few weeks.

Even though your success might seem small to you, I promise you that it will encourage and uplift a sister who has yet to achieve such success.

Meet Linda

My femme name is Linda.  I am 60 years old and started crossdressing about 10 years ago.

Linda’s Crossdressing Success Story

linda-crossdressing-success-story

Linda shares her crossdressing success with us

Before then, I had never been motivated to do such a thing being too busy earning an income and bringing up a family.  Looking back, I do love women and in general preferred their company to men.  When my wife was shopping for new clothes, I always went with her encouraging her and criticising when needed.  In my lunch hour, I often bought clothes for her and was never interested in buying men’s clothes for myself; in fact, the only time I bought my own clothes was when something needed replacing.  I loved my wife to wear miniskirts and high heels, which she didn’t like much at all.  It was only later in life that I realised that I was the one who should be wearing them.

About ten years ago, I started experimenting in secret.  In three years, I had accumulated a small wardrobe of miniskirts and tops and some badly fitting high heels shoes.  It had to be small as I had to keep it hidden in a locked brief case in my study.  I wanted to go further but the secrecy prevented me.  I realised that I must tell my wife and come out of the closet as it were.  I really did not know what to expect, but one morning when we were lying in bed having just woken up, I confessed.  Naturally, my wife was shocked and her initial reaction was that I could continue to do it in private but she did not want to be present at the time.  I asked her if I could email her some photos so that she could see what I looked like.  I guess she must have been curious as she said yes.  We kept talking about it and eventually she consented to see me dressed.  When she saw me, she said I looked OK, although she was a bit jealous of my legs and figure.  Shortly after she told me that she would accept my crossdressing because in her words: “Once I saw that it was still my M________ under the clothes, I realised I had nothing to worry about.”

linda-crossdresser-success-story-shopping

Linda confidently goes out in public

From then on things just got better and better.  Not only did my wife accept my crossdressing, she became an active participant and supporter.  She helps me buy clothes, jewelry, make-up, shoes, hose, wigs and in fact anything I need to be a girl.  My life went from hell to heaven in no time at all.  Christmas and birthdays took on a new meaning with a whole new range of gifts that could be bought.  We have such fun together; crossdressing has added a whole new dimension to both our lives.  Shopping together is always fun as we are always on the lookout for new “frocks”.  We both know that crossdressing is fun, creative, sexy and harms no one.  And we love it.


The emphasis on the last sentence was mine, just so you don’t miss what a positive experience crossdressing is for Linda and her wife! Read a few more crossdressing success stories, or decide to take the next step towards your crossdressing success. Read a crossdressing book, share a resource on crossdressing with your wife or transform your feminine appearance.

The Luxurious Taste Of Femininity

There are so many aspects of crossdressing that I enjoy immensely. The swish of a skirt as I walk. The gentle touch of stockinged legs against each other. The sway in my hips as my heels click against the concrete. Whether a tactile sensation or auditory delight they all thrill my soul, surrounding my senses with femininity.

Yet all this would seem incomplete without the luxurious taste of femininity on my lips. A deep lipstick or light and breezy lip gloss seems to complete the experience. It’s not just the sheer femininity of it’s appearance, but also the unmistakable taste.

Lipstick comes in more than just a tube

Lipstick comes in more than just a tube

When I was younger I had mixed emotions about lipstick. I desperately wanted to wear my mother’s lipstick, but I was afraid that I wouldn’t be able to get it off when the time came to conceal my cross dressing desires. One day when my mom was out the temptation overcame me, and I “expertly” did my lips in a deep red. For the next hour I was in heaven, intoxicated by the taste and smell, but all too soon I had to I embark on “operation extreme hygeine”. This involved:

  • Vigorous removal of the lipstick with tissues that were dutifully flushed.
  • Washing my face with soap
  • Showering and another scrub of my lips with the face cloth

At the end of it all I was mortified. My lips were still red, in fact they looked redder than before. What I didn’t realize at the time, was all the scrubbing had brought the blood to my lips. The lipstick was long gone, but now I was naturally tinted.

Thankfully my mom never suspected, or if she did she kept her suspicions to herself.

These days I know that makeup remover is the easiest and fastest way to remove lipstick. Yet strangely I’m also more comfortable wearing it out – perhaps the long hair, skirt and heels would give me away first :)

I also enjoy experimented with different techniques and types of lip colors. Next on my list is Bare Escentuals lip colors. I’ve always wanted to be able to craft movie star perfect lips. I’m hoping that lipstick made to be brushed on will give me finer control, for a more perfect look.

Is lipstick your ultimate taste of femininity? Comment and share you lipstick inspired story.

Some Tips for Passing as a Woman

Passing… it seems like the holy grail for crossdressers. If we could work hard enough, lose that extra pound and practice voice lessons for another hour – maybe, just maybe we could pass as a woman. In our minds we’ve build up passing as something elusive that is to be dreamed about and never achieved.

Yet passing is closer, and easier than you’d think if you let go of the notion that everyone, all the time must only every perceive you as the woman you’re trying to impersonate.

Here are nineteen practical tips from Kelly Stevens for how to pass as a woman. If you’re serious about passing you’ll find more high quality advice in the world’s best crossdressing guide.

How to Crossdress and Pass As A Woman

1. Dress your age. If you aren’t a junior, don’t buy your clothing in the juniors department

2.  Dress appropriately for the situation. A cocktail dress at the mall isn’t optimum. Make up needs to be appropriate.

3.  Crossdressing is an illusion. A genetic woman can go out without any make up and can look a mess but not look like a man. You can do the same as a man and not look like a woman. You need to constantly preserve the illusion and this involves diverting attention away from your flaws and using clothing and most importantly accessories to preserve the illusion. I do not need glasses but found they feminize me so I bought some (in the women’s section of an eyeglass store). wearing men’s glasses simply is not good enough in 99% of the people I know. I wear a hair band, diamond engagement ring, chain bracelet, necklace, earrings that dangle, and red lipstick because many people have critiqued me and said these things feminize me. The red lipstick and nail polish divert the eyes away from other parts of me.

4.  Choose a wig wisely, This may be among the most important things you do. Length, color, style all matter. (If it is too perfect, it will look fake.)

5.  Hair removal is always an issue.  You think nothing of spending a great deal of money on clothing and cosmetics so spend some on a quality razor.  Consider hair removal on your face if necessary. I had laser hair removal and it was the best thing I ever did. Use the right foundation to cover the beard but shave it off first! covering is not as good as removing. Shave closely and several times.

6.  Apply make up skillfully.

7.  Cover your arms if you need to. My arms are larger than a woman’s so I wear some type of top. This means I never get to wear sexy cocktail gowns and expect to pass but I can usually find something nice with sleeves. Cover your Navy tatoo!

8.  Keep your skirt length appropriate.  In fact, keep everything appropriate. Anything that looks out of the ordinary will be noticed and once you are noticed you will not pass.  Much of the time if others really noticed me i would not pass yet somehow I pass extremely well. Why?  Because I blend in and fly under their radar.

9.  Avoid direct confrontation with anyone and when it i necessary to interface with a waiter, store clerk, etc. be prepared.  When i go to the grocery store i know they will inevitably ask me paper or plastic so I am ready and reach for a plastic bag.  I know I will be asked cash or credit so I have my cash or credit card in my  hand where they can see it before they ask. But if I have to speak, I speak softly and quietly and smile.In a restaurant, point to the menu item as you order. This reduces the need to fully speak in detail.

10.  Choose where you go in public carefully to minimize problems. If you don’t really pass, stay out of the ladies’ room. I go out at any time of the day or night in Times Square and pass but I avoid groups of teenagers like the plague. They will notice and if they notice they will not notice quietly.

11.  Walk like a woman not a caveman.

12.  Relax. If you are afraid, you will walk like you are afraid. Have confidence.

13.  I’ve seen many men who do not prepare themselves to pass. One CD friends is an auto mechanic and he shows up at support group meetings with black grease on his hands.

14.  Eat and drink like a lady. I love beer but more women drink wine so i drink wine. Men stuff their faces. Women are much more, well, feminine in how they eat.  Study female  behavior so you can emulate it properly. A word about smoking. I personally feel that smoking is one of the easiest means to tell if someone is a CD or a real woman. Few men can smoke like a woman. You think you can, but you can’t.

15.  Carry a mirror and use it. Men don’t need much attention but women need constant attention. Walking from the parking lot to the Mall can result in blown hair. Eating can alter make up. Be prepared.

16.  Smell like a woman.

17.  Pay attention to detail. You may not be into make up and real women don’t need it to look like a woman but it will really help you. Curl your lashes. (No, don’t use artificial lashes). Keep your clothing stylish. No, that man’s coat isn’t going to pass as a woman’s coat. Details! If you have a huge Adam’s Apple, wear turtle necks. Learn to adapt.

18.  We all want to have our own set of 52 DD tits but if you wear 52DD tits you are going to attract attention and you will therefore be noticed.

19.  Be self aware. Know your limitations. Unless you have practiced dancing like a girl you probably won’t do it like a girl.

And there you have it – nineteen practical tips for crossdressing that don’t require night classes or intentisive training. Don’t stop now, there is so much more to learn about crossdressing – learn how to pass as a woman.

Sarah's Crossdressing Success Story – A Sister's Secret

Crossdressing Success Stories are real stories from crossdressers who have succeeded in an aspect of femininity. Their successes may be big or small, but their significance is important. Small successes lead to larger successes, and even though not all of us will be the perfect picture of femininity we all deserve to enjoy the crossdressing journey.

Share Your Crossdressing Success Story

If you would like to share your crossdressing success story, please email me at vanessalaw@crossdresserheaven.com and let me know you’d like me to share with others. Please include:

  • Your femme name
  • A brief introduction (1-2 sentences about where you live, how old you are and such)
  • Your story (if you go over 700 words I’m going to edit you down :) )
  • Optional – A photo of you (no nudity please)

I’ll post your story on Crossdresser Heaven within a few weeks.

Meet Sarah

My femme name is Sarah. I currently live in Fall River, MA. I am 53 and have been doing this since I was 13 – that may be the age when you figure out who you are.

Sarah’s Crossdressing Success Story

I started doing this when my sister dressed me up for Halloween (it was more of a treat than a trick,since i liked the feel.)  I went on to keep doing it, through service in the Army in the 82nd Airborne. I would rent a motel room for the weekend, and dress like I wanted.

I got married, but still liked to dress. Got seperated, spent 2 years dressing (at my own place and wearing frillies at work), then went to infantry combat in Afghanistan. When i came home I went to my sisters house where we exchanged secrets.

She told me she was a Wiccan – I did not care, freedom of religion ,right?  I told her about Sarah. She wondered where some of her underwear went!! As a result I spent a weekend with her as a woman. We went shopping for dresses, underwear, makeup, went out to eat (I can pass).

IT WAS FANTASTIC!!!!

It had nothing to do with sex, it was just about the bras, panties, stockings, garterbelt (HATE pantyhose), slip, skirt, blouse and heels(though i did learn how to choose shoes after that!) Still LOVE this!!!!!!!!!!!!!!!!


You can more wonderful crossdressing success stories such as Teresa’s first time passing. If you’d like to experience a crossdressing success of your own the world’s best crossdressing guide will give you the tools you need to look fabulously feminine!

Petra's Crossdresser Success Story – A Tale of 2 Trips to Victoria's Secret

Crossdresser Success Stories are real stories from real crossdressers who have overcome what life has thrown at them to achieve their own measure of transgender success. Whether it’s getting your nails done at a salon, attending a transgender event or shopping for yourself in a mall. The crossdressing journey has many joys and these stories are shared to provide hope, encouragement and upliftment to all in the transgender community. If you would like to provide strength to a sister, please share your crossdresser success story. All it takes is a few heartfelt words, and I’ll post your story on Crossdresser Heaven within a few weeks.

Meet Petra

Petra shares her crossdresser success story

Petra shares her crossdresser success story

I’m 46 years old and live in Atlanta GA, happily married (Petra is not out to partner sadly – big New Year project). Petra lives at voyagesenrose.blogspot.com more then she does in the real world. But she does get out when she can.

Petra’s Crossdresser Success Story

Over the years I have bought many nice things in stores. In drab. Sometimes for my wife, sometimes for me. My shopping was typically cloaked under the plausible pretence of shopping for my wife. Good cover.

Nonetheless, even when I am legitimately buying something nice for my wife, there is a part of me that wonders …. “Does she think this is for me? Did she clock me? Does she deal with crossdressers everyday?”

Well, I did some nice shopping en femme recently, and it gave me some courage to change the way I shop in drab. Last week, dressed, I popped into Macys, stopped in intimates, looked at shoes, thought about a couple of dresses, not seriously shopping, but rehearsing shopping. Nothing really stood out, including it seems, Petra. Just another girl in a store.

The out into the mall and inevitably into Victoria’s Secret. All the mirrors and the pretty, pretty things. Now the fun begins. The entirely cute young VS girl said hello and said she was envious of my ability to walk in heels. Sweet. That night, she said, a $10.00 purchase would win me a surprise value card – likely worth $10, but maybe $1,000. And then, my new friend said that if I wanted to try anything on, I was most welcomed.

Somebody shoot me while I am happy.

I really had the wrong outfit on (turtleneck knit dress – a real wig-popper) so I couldn’t take her up on it. But do you know, the point was, I was fooling nobody (fully) and it just did not matter. I am a girl on a budget, so I just picked up a pair of control top hose with a very pretty lace garter effect. Cashed out, got a little spritz of perfume, a nice catalog, a yet to be redeemed gift card and a pretty pink bag to walk back out to the car with.

And this really got me thinking. I cannot get out as much as I like to en femme (who does really?). But I do like to prepare for nights (and days) en femme. When I see a nice look on a real woman, I often say, Petra ought to have that look. And then, maybe I go shopping for Petra. In drab. Can I make that more fun?

Visit # 2
So I was in drab yesterday, and my new gift card was burning a hole in my pocket. Those hose I mentioned earlier on – fabulous. Really snug around the hips and butt. Nice glossy finish. Yum. So I dropped in on Victoria again.

“Can I help you find something today?”
“Sure, I am looking for hosiery”
“Is this a gift?”
“No, its for me.”
“OK, just over here…”

And do you know something, there were no flashing red lights, no women and children shrieking and running away. Just me and the nice girl talking ’bout tights.

“You don’t need the control tops do you? I mean look how skinny you are…”
“Well, I have different parts I need to … ummm…. well, contain you know… and the padded panties, well they need to be smoothed out a bit too.”
“Really? Well, yeah, I guess that makes sense … oops, hey, I think we are out of the black in C. How about almost black. Would that work for you?”
“Sure, that will do”
“Do you need anything else today?”
“Need, no. I want everything, but.. .”
“O, well you just come back anytime. Do you have a Victoria’s Secret Angel Card?”
“Um, not yet.”
“You really ought to get it. You’ll never ever pay full price”
“OK, well I will figure that one out later….”

Well, there it is. I am committed. When I shop for me, I will shop openly. I pretty much expect that I will get terrific service, and will probably meet some nice people just by being a little more honest about it. And it might just make life a little more interesting for the nice, nice women working in a small handful of shops.


Don’t give up having your own successful crossdressing experience – read other crossdresser success stories here and then let your feminine beauty emerge by following the advice in this crossdressing guide.

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