crossdressing success story

Miriam’s Crossdressing Success Story: It Started With a Halloween Party

By Vanessa Law | Published April 16, 2009 | 3 Comments

Today we’re blessed to share a crossdresser success story from Miriam, who looks back on many years of crossdressing to share two experiences that started it all for her. She’s a wonderful writer and I was touched by how her story combines trepidation and excitement with the loving support of a good friend.

If you’d like to share, please submit your crossdressing success story and I’ll post it on Crossdresser Heaven in a few weeks.

Meet Miriam

My story is not unlike others. I started very young and have been a crossdresser for over 45 years. I am happy to say that in all this past time, I have always enjoyed my femme side.

Miriam’s Crossdressing Success Story

My first real time experience came at age 14. Sandra Dee was the girl of everyone’s dreams, blond, blue eyed, young and sexy. I had fooled around with wearing high heels and such for a few years, basically what most kids do as they discover their desires. My neighbor and I got together for a Halloween party, she was 16 and very sweet and supportive, it was she who actually bought me my first pair of heels.

We decided that I would go to the party as Sandra Dee, great poodle skirt, pink angora sweater, brown stiletto heels. I was blessed with very smooth femme features, baby face as they say, no sign of a beard until I was in my 20’s. I was a girl size 8, shoe size girls 8 and a 32 c size chest.

She did my makeup in light tones, red lipstick, gold drop earrings. I wore beige panties and a beige bra with padding, neutral toned stockings with a garter belt and had my nails done in red even though they were short. She did my hair up in a French knot, my hair was naturally long, Beatles era. We went to the party as cousins and not one person was able to tell I wasn’t a girl. It was a breath taking moment. Every chance I had to dress up I did, mostly with her clothes until I decided that it was time to buy my own.

On my 16th birthday I bit the bullet and went shopping. I went to a local dress shop to buy my first outfit. I was sweating all over, but I decided I had to do it. A young sales girl came over to help me and asked was I looking for a gift for my sister, I said no. I said it was for me. She looked at me and said you look like a size 8 or so and I said an 8 and that was that, I had broken the ice. I bought a beautiful blue outfit and one in red too. They had a great shoe department  and I bought 3 pair of heels. I tried them all on with the dresses to see how they looked and I was very pleased, so was the sales girl. The rest is history as they say. I have been buying women’s outfits since and will continue being my femme self hopefully for a long time to come.

Not every experience is always good, I was lucky. I decided I was not going to hide who I was, maybe that’s what made the difference. Self confidence that’s what will make it happen

Miriam

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Would you like to live a crossdressing success story of your own? Lean how to crossdress and pass as a woman.

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Steve’s Transgender Success Story – To Desert Storm and Back

By Vanessa Law | Published March 26, 2009 | 1 Comment

I’ve retitled this week’s crossdressing success story since it involves people who both identify with two different places on the transgender spectrum.

If you have a story to share you’d like to share with the readers of Crossdresser Heaven, please email me at vanessalaw@crossdresserheaven.com and let me know you’d like me to share with others. If you identify anywhere else on the gender spectrum (transgender, transsexual, etc.) you are also welcome to submit a story. Readers of Crossdresser Heaven are at many places on their journey through gender self-discovery. I know that I would personally love to hear from more ladies who have found a different answer to their gender questions.  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)

Meet Steve

Steve is a 50 year old cross dresser who lives in the beautiful Pacific Northwest (Washington State).

Steve’s Transgender Success Story

I remember I was about 12 years old trying on some of Mom’s old swimsuits I found one day. Then I can remember being about 14 when I got an pair of my sister’s panties.   Little yellow polka dot ones of yellow nylon/white dots.

I used to spend a lot of time looking at women’s underwear pictures in newspaper ads and Sears Catalog and such before I finally got up the nerve to buy some granny panties. This was when I was 15 or 16, and I can tell you I did not like those as much and threw them away. The next time I got panties was when I was 18 and ordered some from a department store. They were white bikini panties, that I then started buying regularly from department stores – the boxed Playtext panties. This went on for several years – I would buy them from department stores by filling out the order form and waiting for delivery (Ed: Ahh, the Internet is such a blessing for the modern crossdresser)

When I got married I told my first wife and she hid all my men’s underwear to force me to give up panties.  Alas I had to throw them all away, I was in the military and could not wear them 24/7. That did not last long and I went through several buy and purge cycles before finally getting a divorce and being able to keep my underwear. I got remarried few years later (you would think I would learn) and told her up front. The marriage lasted a couple of years and when I wanted to wear woman’s jeans we got a divorce. She said I was not “Man Enough”.

Anyway when I retired from the Military I decided to wear what I wanted.   I kept both men’s and women’s underwear.  I met my partner at local Crossdress Social Club meeting.  She was Pre Op Transsexual and we got married after she had the operation. I have been wearing panties and women’s clothes (jeans, some shirts) since then. Heck, I don’t own any men’s underwear or jeans.   Lane Bryant “Right Fit” are my favorite jeans.

I tried the whole dress up thing – Wig, dress, heels and such.  It just was not me.  I’ve been out in public dressed (to dinner with a group), but I realize that I’m a guy who likes to wear woman’s clothes.

I now have a very supportive wife and live quite happily.  I do the housework (I got hurt in Military during Desert Storm and get VA Disability, SSA and CRDP Pay) so I can do what I want and have enough money to live.

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Steve – thank you for sharing your story. It may take a while, but we can all find love and acceptance if we look hard enough.

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JamieGhee’s Crossdressing Success Story – Out The Closet And Into A Ball Gown!

By Vanessa Law | Published March 13, 2009 | 2 Comments

Greetings Dear Readers, this week we have a story from a very special lady who went out en femme for the first time ever a few months ago. Of all the crossdressing success stories I must confess that the two stories that bring the most joy to my heart are those where our fearless heroine engages in a first of epic proportions – venturing out en femme for the first time, or telling their special someone about the woman inside.

Meet JamieGhee

I am JamieGhee, and have been cross dressing since forever. I have never been out en femme, and went to my first event, “Beauty and the Beach,” in Rehobeth Beach, Delaware.

JamieGhee’s Crossdressing Success Story

As I am waiting for check-in time, I am back to experiencing that excitement mixed with anxiety that I have had since I first signed up to be here-back in March. It is now the day before Halloween. All those months of waiting and wondering, and now I’m finally here! The trunk of my car is packed to the top with suit bags, suitcases, four pairs of shoes, three wigs, makeup and a jewelry box. I don’t know if I have brought too much or not enough.

An hour before the first gathering of the evening, I find myself rushing around my room, getting a little frantic as I try to sort out what to wear. I have chosen to bring “age appropriate” clothing, being 64 years old after all. My first choice is a dark red, ankle length skirt with a white, puffy sleeved blouse. With makeup done, I put on my hair and slip into black pumps with three inch heels, my most comfortable shoes. Then there’s this totally new thing, a purse, and what goes in it? Then finally, there she is, reflected back in the full length mirror. The image smiles a little, and oh my gosh, this is it!

I have determined in advance, from the advice on Ms. VickiRene’s website, to smile and greet everyone I encounter. I have no illusions that I “pass,” and I know I’m not by nature an outgoing person. I am determined to do the best that I can, and not to run away from myself either. I step into the hall and tingle with excitement and anticipation. I do my best feminine walk (from the hips, girl!), and arrive at the dining room. Suddenly, my eyes go “macro,” as I try to take in everything I see. There is a large room filling with some of the most beautiful people I have ever seen, and nearly all of them, except the genetic women, are just like me. I cannot keep myself from smiling.

The next morning, another-first-time-in-my-life, being dressed en femme to start the day. Although not a morning person, I arrive at the dining room already smiling. Later in the afternoon I decide on another never-done-that-before thing-fingernail polish, on my own, grown-long nails. This starts out being a minor disaster, and I am asking myself, how hard can this be?

By dinner, my jaw muscles ache from smiling, but I am describing my experience to anyone who asks as, fantastic. This is Friday, the evening for one’s best dress, and for something called the Princess Promenade. I wear an evening dress, which is a light peach color, and has an elegant flow to it. When I return to the dining room for the event, I find it is now filled with really beautiful people. Those who want to enter the promenade line up, and at this point I find myself thinking the unthinkable-would I actually want to do that? Won’t I look foolish, at my age? Then I find myself doing the unthinkable, and joining the line to be escorted into the spotlight and introduced. At that point my eyes go out of focus, I forget everything I know about how to walk, how to stand, and feel that I shuffle off into the darkness after my 15 seconds in the spotlight. But I did it!

Saturday morning brings the announcement of the Princess and her court, then a group photo on the boardwalk. In the evening is the talent show after dinner. Though not something I would ordinarily find entertaining, I seem to have a different mood in my black evening dress and four inch heels. And all too soon it is all over.

Back home, I find a certain joy, and in some odd way I am proud of myself for presenting the person who is JamieGhee for the first time, for bringing her out from the deepest part of her closet. I met so many beautiful people. For all that I wasn’t-like passable-there is so much that I was, for myself, perhaps for others.

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If you have a story to share you’d like to share with the readers of Crossdresser Heaven, 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)
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Joanna’s Cross Dresser Success Story – Celebrating the Woman Inside You

By Vanessa Law | Published February 27, 2009 | 4 Comments

This week our cross dresser success story takes us all the way north to Quebec Canada, where we join Joanna on her journey through hardship to celebrate the woman inside. As regular readers know by now, cross dresser success stories are real life stories from wonderful transgendered woman all over the world. These ladies have conquered self-doubt, bad hair days and all manner of malady’s to achieve success in some aspect of their crossdressing.

Please share your own cross dresser success story. It can be funny, scary, dramatic, emotional or described by some other adjective completely. A small slice of your cross dressing journey will shine a light for those who still travel this road in darkness.

Meet Joanna

My name is Joanna and I live in Montreal Quebec Canada. I have been a crossdresser since a very young age. Now divorced and looking to start the next phase of my life. I am 45 years old.

Joanna’s Cross Dresser Success Story – Celebrating the Woman Inside You

joanna-cross-dresser-success-story

Joanna Shares Her Cross Dressing Success Story

My story begins at age 5 or so when I was playing dress up with my 2 younger sisters. I remember donning a pair of mom’s pumps and putting a rag on my head to serve as long hair.

My mom sent me a strong message that day to never to repeat this (although she does not remember doing so) and things went underground from there. I continued to dress in my room and when there was no one home. I would go into mom’s closet and wear her dresses, heels and makeup.

As puberty hit and the dreaded orgasm appeared I started to feel the guilt around my dressing and began the dreaded purge cycle for quite a number of years. You see I was raised in a very religious household and this was an aberration. I remember one time as a teenager crying in the shower praying that the urge would go away. Of course it never did.
I married shortly after my father’s death from cancer (in retrospect a mistake) and tried hard to suppress my desires for as long as a year at a time. I would buy clothes and after having masturbated in them after an outing as Joanna promptly threw them out always promising myself to never do it again.

Then after 12 years of marriage I told my wife about my secret in a letter to her which she actually found before I could give it to her. At first there seemed to be nothing but understanding and compassion around this issue and it was great. I entered a gender therapy program at the hospital to try and figure out where I was going with all this. My wife even went out with me a few times with me dressed as a woman. Then some months later she turned on the whole thing and said she wanted a divorce.

Our marriage had never been the strongest from the start and now this was the camel that broke the camel’s back for her. I was not happy either and after having had a health crisis in late 2007 (as it turned out a small stroke) things started to really go downhill for the marriage. In fact during my 10 day stay at the hospital she came for a one hour visit.
I am now divorced and things seem to be going better. I am feeling more relaxed, my children are adjusting well and my ex and I are able to communicate better. We are co-parenting our children and focusing on them. The therapy helped me to accept myself as I am and to realize that I am this way for a reason. God loves me exactly as I am and there need for guilt or shame regarding this activity. My mother and siblings now know about Joanna and have tried to be very understanding – so while they may not relate to what I am doing they take my word that it is something very deep and trust that I need to express it. God love them for it.
I now celebrate the woman in me by regularly going out and doing the little things as Joanna. I grocery shop or go downtown for a coffee. I get tremendous peace from this and treasure this part of myself. I am currently living with my mother until I get a new place and she faithfully washes my boy and girl clothes. I know I really have a good thing there.
Although I am now alone and would welcome an understanding woman in my life, I will never again suppress this part of myself to please another. I have learnt that we all need to be ourselves and in so doing be a better person towards other people even if society rejects us for who we are.
Peace,
Joanna

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Mandy’s Crossdressing Success Story – The Encouraging Crossdresser’s Wife

By Vanessa Law | Published February 13, 2009 | 1 Comment

Crossdressing Success Stories are real stories from crossdressers who have overcome fear and self-doubt to let their feminine beauty emerge. Their story of success may be one of triumph over adversity, or the blossoming of a special relationship of openness with those they love. Perhaps the crossdresser’s wife played an even more integral part of their success story.

Share Your Crossdressing Success Story

Please share your crossdressing success story, it only takes a moment and your crossdressing victory will encourage a sister who is just exploring her transgendered nature. I’ll post your story on Crossdresser Heaven within a few weeks.

Meet Mandy

I’m a 31 year old white male, heterosexual, and live in the Seattle area.  I’ve had the desire to crossdress for about as long as I can remember.

Mandy’s Crossdressing Success Story

I think it started when I was maybe 5 or 6?  My best friend, a girl, lived across the street from me.  She was really big into dance, and as such, had lots of different costumes.  I remember she had me try on one of her pink tutu’s one day (don’t know why…. she probably thought it’d be funny.)  I remember once I put it on, the embarassment went away and I felt oddly comfortable, and even satisfied.  For awhile, every time I went over to her house, I wanted to try on the tutu.  The humor in it wore off eventually, and I started to experiment on my own.  I remember taking naps in the afternoon when home, and while mom was at the other end of the house watching her soaps, I’d sneak into her room and steal a few things from her drawers.

Taking mom’s stuff, or stuff from female friends and cousins, was all I did up until I moved out and lived on my own.  Thank God for the JCPenney catalog, and the internet.  I ordered myself a decent amount of underwear (that actually FIT!), then sort of lost interest in it all for awhile.  Don’t know why.  A good few years went by where I still had the free time to do it, just never really did.  When the opportunity came to move across the country for a job, I took that as the chance to pitch everything (purge…  I know, “don’t do it!!!”)  as I thought I was done with all of it.  It wasn’t until I told my wife about it a few years later that I got back into it, through her encouragement.

I’m now married, have an amazing wife who loves and accepts everything about me, and is willing (sometimes pushing) me to explore the depths of my interest in it all.  I’ve learned a lot this last year, and am loving it more than ever!  Hopefully, with the wife’s help, I’ll work up to a night out or something fully dressed  :)

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It warms my heart to hear stories where the crossdressers wife plays such a positive and affirming role. I know that many crossdressers agonize over their wife’s acceptance, often keeping their secret for many years beyond what they should bear. If you are struggling to tell your wife, please read how to tell your wife you crossdress. If you’ve told your wife with great success, please comment and share your advice with others.

Hugs and blessings,
Vanessa

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

By Vanessa Law | Published February 6, 2009 | 3 Comments

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.

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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

By Vanessa Law | Published January 30, 2009 | 5 Comments

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.

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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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