crossdresser success stories

Crossdressing With Her Wife’s Support

It’s Thursday – that means it must be time for a crossdressing success story! This week’s story comes from all the way south in Dallas, bounces off my computer screen in the Northwest and is now shared with you. Thank you Janice for sharing your crossdressing success story with us.

A quick note before we meet Janice. I’ve had a few ladies offer to write fictional stories. While there are many sites that are eager for crossdressing fiction, I’d like to keep the stories on Crossdresser Heaven about real crossdressing triumphs. I feel that the authentic victory in our transgendered nature, however small, is worth celebrating and inspires others on their path.

If you have a real life crossdressing success story to share I’d love to share it with others on Crossdresser Heaven! Send me a quick email to my address at vanessalaw@crossdresserheaven.com and include a brief introduction, your femme name, a short story (500-750 words) and a picture (optional). I hope to hear from you. Now it’s time to meet Janice…

Meet Janice

My fem name is Janice Kay Davis. I am a 62 year “young” life-long cd in Dallas with a beautiful and supportive wife who accepts both sides of me and helps me be feminine when I go out with the “girls.”

 Janice Crossdresses with the support of her wife The first time I remember wearing any sort of female clothing was when I was about 5 years old. I tried on a pair of stockings (my mother’s I suppose) and they felt very exciting and normal to me. From the hose I “graduated” to hose, heels, panties, nighties, etc.

I knew of no one else in the world who did this, so I thought I was “weird” or perverted. I thought this way all through elementary and high schools. In college my junior year, I lived alone in a rooming house and had quite a collection of hose, heels, lingerie and often wore feminine things under my boy clothes as I went to classes. It just felt normal for me to have some article or two of feminine clothing on, even if I was “underdressed.” I almost always wore panties and a nightgown when I went to bed and felt very feminine when I awoke in a nightgown. It made me a little sad that I couldn’t dress as a girl on campus, but I knew that was only a dream.

Through several years (and several wives who could not or would not tolerate my fem side), I learned that there were many more men just like me who had strong feminine sides and liked to explore those sides by crossdressing. My current (and final) wife, as I said, fully accepts Janice Kay as a part of who I am. She helps me be more feminine for my “outings” and is entirely comfortable with it. She, and sites such as Christian Crossdresser has helped immeasurably in me coming to grips with who I am and the fact that God made me this way and, as we know, “He don’t make no junk.”

Thank you Christian Crossdresser and thanks and blessings to all other gurlz out there. Just remember, you were “fearfully and wonderfully weaved in the womb” to be who you are today.

Janice Kay Davis

P.S. Janice, you look lovely for 62 years young – I can feel the joy in your smile even thousands of miles away.

P.P.S. If you haven’t told your wife yet – find out how to tell your wife you crossdress.

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Michelle’s Crossdresser Success Story – Tell One Person Today

When Michelle first emailed me her story she prefaced it with a sentence that many of us can identify with. She said:

I always saw that "Share your success story" thing in the emails and thought "I wish I had a success story."

I do that myself sometimes. I look at the other successful, beautiful, confident transgender woman and sometimes think to myself, “I wish I was like them. I wish I had a taste of such success.”

Michelle, thank you for sharing your success story, and for showing us that each of us can achieve our own success without needing to compare it to others.

If you’re like Michelle, and have been wondering whether you have a crossdresser success story to share – take a moment to think of any positive experience you’ve had crossdressing, and share your crossdresser story.

Meet Michelle

I have been going by Michelle online, but have also recently adopted the name Rachel, as it is more similar to my own name (Richard).  I started wearing panties in high school, but since I didn’t have sisters, they were what I bought for myself.  I gradually added bras and slips to my collection (which actually got purged on a regular basis), and started trying on skirts after I got married (over ten years ago).  I bought my first new dress for me five years ago (actually tried it on in the shop and had the lady make a few alterations for me) and currently own a few skirts and other ladies clothes, including some heels.  I rarely get a chance to dress, and even that is almost all at home in the privacy of my own bedroom (I can’t even walk around my own house because we have kids).  (Wow, I can really ramble sometimes — anyway, on with the story.)

Michelle’s Crossdresser Success Story

I recently started seeing a therapist to help me deal with my inappropriate reactions to stress (yelling at the kids, and inappropriate online activities).  We discussed my crossdressing and I ended up going to the mall to visit a lady I had met in a bridal shop before buying something for my wife, and had also developed a business relationship with.  I asked her if she knew that I was actually sort of shopping for myself as well, and she said she suspected but wasn’t certain.  It felt really good to have a real live person know about me and not just a random sales girl at a mall that I would likely never see again.  I have had several shopping trips that were somewhat successful in terms of me being honest about the intent of my purchase.

Yesterday’s story starts somewhat a few weeks ago.  I was getting ready to change the oil and for some reason ended up wearing a skirt under my coveralls instead of pants.  Then I realized I could probably get away with that with some of my looser fitting casual slacks as well.  So yesterday I wore a skirt under my pants as I went to the dentist.  Then after the dentist, I slipped my pants off in the car and went shopping at a bridal store in a skirt.  I didn’t have the awkward moment of, "It’s not for my wife, it’s for me."  It was great.  I had a really good time shopping and the lady was very nice.

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Aysha’s Crossdressing Success Story: Practice and Passing in Vancouver

Crossdressing success stories are heartfelt stories of crossdressing triumph. I thank all the wonderful ladies who have shared their story with me so far. If you’re still waiting to submit your story – what are you waiting for?

Before you meet our next lucky lady I’d like to appeal for a different type of story. I’ve received a few emails from wives and girlfriends of crossdressers. Many are confused and scared. It can be quite a daunting thing to learn that your man is a crossdresser.

If you’re the lady in a crossdressers life and would like to share a success story from a different perspective please email me (vanessalaw@crossdresserheaven.com). I can’t tell you how much it would mean to all the woman who come here trying to understand their husband’s strange desires. If you’d like to remain anonymous or use a pseudonym that’s no problem. Thank you for helping to spread the hop.

Meet Aysha

My name is Aysha, and I am a 36 year old East Indian crossdresser living in Abbotsford, BC Canada.  I am 5′6″ tall, 135 lbs. with a “pretty boy” face (so I have been told) and a slim build.  [Ed: You’re one lucky girl hon!]

Aysha’s Crossdressing Success Story

I have been dressing up since I was 14 years old, and over the years, I have perfected my transformation- right down to waxing my entire body and laser hair removal for my face.  My wife is supportive, but does not know I still go out in public. Two years ago, she found my clothes and threw them out, saying that “I was a fag” etc etc..  I told her I only had a fetish, not a compulsion to dress- that is, until she found my collection again!  This time, I “disposed” my clothes, makeup and wig, right to a monthly storage place!

She actually bought me a few lacy bras and panties, with some makeup when I told her the truth about my obsession.  She enjoys seeing me dressed up in private, and we have had many fun times in the bedroom, to say the least!  Over the years, I have perfected my technique, from the makeup to the clothes to the pitch of my voice and my walk.. I feel confident when I am a girl and always “pass” with no problems, whether I am dressed up “all business”, jeans casual, sexy niteclub wear, or even a skimpy bikini!

I love shopping, and often go to the malls in Vancouver, sometimes alone, or other times with a TS girlfriend.  My favorite look is a pair of tight dress pants with heels, a sexy low-cut top with a blazer and silver jewelry, and my business tote, so it looks like I just got off from work!

My wig is just past my shoulders, with sideswept bangs.  I keep my makeup low key and classy- some mascara and shadow, eyeliner and lip gloss, with a hint of blush on my cheeks.  My best advice to new crossdressers is to invest in a top quality hairpiece and keep current of the latest clothing fashions- nothing will give you away faster than hair that looks like it came from a halloween sale and clothes your grandmother would wear!

Finally, when you dress to impress, be confident and maintain eye contact- if you act shy and nervous, you WILL be “clocked” every time!  I have had a number of fun and sexy adventures while being dressed and would enjoy sharing these stories with the other girls.  Some of my experiences are VERY explicit and may not be appropriate in a public blog.

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Liberty’s Crossdresser Success Story – It Started With A Dare…

Crossdresser Success Stories are stories from real crossdressers who have succeeded in accommodating their inner woman. Some successes are spectacular, others are more modest – all are important breakthroughs for the wonderful ladies who experience them.

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. You’ll be famous ( :) ) , and you’ll be doing a good thing for everyone in the crossdressing community.

Meet Liberty

I am 53 years old and experimented with cross dressing for over 20 years.

Liberty’s Crossdresser Success Story

At first it was just a dare for a fancy dress party where men dressed as women, women dressed as men. So my ex wife did the business on me and we even borrowed a wig….and she made me into a tarty type women. At the time I thought wow I actually like this, putting on a suspender belt and stockings and a bra stuffed out with tissues to give me shape , I just felt good, and the swish of a skirt around my legs was so nice. I secretly love the way I looked and the shape I had.

After that I experimented in private alone and it started to dawn on me I was a transvestite, it was more than just cross dressing a bit…I wanted to feel and look like a proper woman, and felt so happy and comfortable when I was fully dressed. I would spend whole afternoons by myself dressed to the max .

I got divorced (nothing to do with that) and started to buy the most pretty things I could, from every day clothes to silk night wear, one shop assistant in an exclusive lingerie shop guessed what I was doing and asked me if they items were for me…so I just said yes…no problem she said…we get this a lot….and she started to advise me on what looked right and what did not……all my underwear was the best quality. Dont buy cheap it is false economy.

Then I met another lovely lady, (at a heavy rock concert) and we went steady and talked about so much and fell in love. Eventually the natural thing happen and we wanted to marry, but I decided I’d had enough of my secret side, so I told her, she never batted an eyelid, and just said that’s fine by me, she’d had another male friend exactly the same and it never bothered her…….she said, why should ONLY women know the feel of silks and nice clothes and if more men tried it they may find it a calming influence, and real chill out, especially after a serious hard and stressful day at work…….and she encouraged me then and there to cross dress anytime I felt the urge. She has taught me how to put to put make up on tastefully and the right sort of clothes so I look right……for a present she even secretly bought me a long natural hair wig. And she helped me choose a pair of proper synthetic boobs. So now when I am dressed up I do look the part with a beautiful DD curve up top, they were very expensive, made to measure and even skin toned to me and even give me a cleavage…..but you get what you pay for. And I can wear them all day without aggravation etc

So now my lovely wife and I spend what we call girly nights together, and when I transform I am known as Liberty…..I come home from work, and most evenings totally transform myself in a woman, I am still as heterosexual as the next man……and have NO gay or Bi-sexual desires…..I just love to dress and act as a lady. So what would you call me???

My Next step is to go out dressed like this…..but I have not plucked up the courage to go public….maybe one day. My wife tells me I am as natural looking as you could get and not many would notice I was a man especially when she applies make up on me, she really is an expert at hiding all my male facial lines.

I am one lucky guy to have such an understanding wife, but coming clean before we married was the key, so all you secret cross dressing men out there, tell your partners, you may well be surprised at their reaction……my wife feels she has a loving macho man husband and also the best girl friend she could ever want all rolled into one.


If you’re struggling to find the word’s to say when you tell your partner I highly recommend you read My Husband Betty and I Married A Crossdresser. You owe it to yourself and your wife to be prepared before you tell her.

Good luck!

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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.

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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!

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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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