Category Archives: Crossdressing Success Stories

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.

Finding Acceptance in The Most Surprising Places

By Vanessa Law | Published August 23, 2010 | 2 Comments |

Dear Readers,

It’s with great pleasure that I share this week’s crossdressing success story. It’s a story of struggle, of accepting blessings amidst the struggle, and of courage to share the deepest part of oneself expecting rejection.

I encourage you to share your crossdressing success story, however short or long, heart breaking or inspirational – your sharing will be a blessing to others.

Meet Jessica

Hello, my name is Jessica. I’m 26 years old and live in an EXTREMELY republican, very closed minded part of the United States. I wouldn’t dare set foot out of my house as Jessica, at least not in this county. 30 or so miles away… maybe… Anyway, I love the site. I love the support and the encouragement, love the positive energy. It made me want to share my story. It is somewhat long. I present it to you so that you may share it with others if you like, in hopes that it might inspire even just one person to accept themselves.

Jessica’s Crossdressing Success Story

There are a lot of things “wrong” with me. I’m referring to problems that greatly inhibit my ability to have a “normal”[hate that word] life. Let’s not say normal, let’s say… productive. I have a 26.5 hour circadian rhythm, so I have a great deal of trouble staying “aligned” with the normal daily cycle. On top of that, I have a quite painful back condition which I cannot treat, because I cannot take NSAIDs and am a recovering addict to Vicodin, so narcotic pain relievers are a big NO.

I have a lot of social difficulties, largely due to the way I was raised. I consider myself straight, [though if emotions stirred in me the other way I would not reject them] yet I’ve never had a girlfriend, never had sex, never been kissed. I’ve been told more than once by girls I’ve met in college that I’m “just what girls are looking for,” I imagine that largely owes to my sensitivity and opened mindedness. I just fail epically when it comes to the point of expressing my interest. Usually I just avoid the situation, but when I’ve forced myself forward I’ve even had panic attacks. It is a HUGE area of difficulty in my life, and it depresses me greatly, so I will cease speaking of it now.

So that’s what’s wrong with me.

Now for what’s right.

Continue reading »

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A Transgender Wife and a Transgender Husband in Love

By Vanessa Law | Published July 21, 2010 | 7 Comments |

It’s such a wonderful blessing to hear stories from wives who love and accept their transgendered husband. This week’s crossdressing success story is unique journey of discovery for both partners – beautiful, moving and inspiring.

If you’re the partner of a crossdresser please take a moment and click here to share your crossdressing success story. Your joys and frustrations, acceptance and struggles will inspire and comfort other partners. Stories of the good times will provide light and hope, and stories of the bad times will let them know they’re not alone in their pain.

Andy and Natalie’s Transgender Success Story

I feel the need to share our story in the belief that it may help other wives understand and support their husband. I’ll get straight to the point, when my husband told me that he likes wearing feminine clothing & make up I honestly wasn’t that judgmental about it, because my mother taught me to be open minded to such things.

He informed me in a letter that he made me read in private in another room for fear I may react negatively; quite the opposite I can proudly say. I read the letter and thought about everything. It made me realize that I secretly desired to be a man. I told him my secret desire, and I will never forget the look on his face; surprise mixed with love and happiness.

Ever since our relationship has grown immensely. We encourage each other & refer to each other in the opposite sex more. Our spiritual connection was bursting with passion,
understanding, and deep love for each other; it made our relationship stronger. I sense the envy that people have when they see us and it honestly makes me thankful; I’ve found a bestfriend, lover, and soulmate all in one (a rarity in these current times I sadly believe).

I love to have girl nights with him. We practice & share makeup & some clothes. The only downfall we have come to learn is how & if we tell our friends and family about us, but we agree that this is a minute concern & don’t stress about outsiders. We see each other inside & out & share a deep connection & desire for each other.

I just hope that other wives will be as open & understanding because they may come to realize that it can strengthen & intensify the relationship. Just remember that he is opening his soul to you, he’s in a fragile state of self consciousness and any sense of negativity may hurt him. He’s looking for understanding, acceptance, and in my opinion, informing you that he loves you enough to reveal this to you.

It can be a spiritual revelation to the relationship & it has (and I can testify) lead us to act upon our fantasies in a way that I can only describe as ‘OMG, satisfaction.’
- Andy & Natalie from Houston, TX.

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My Beautiful Veronica

By Vanessa Law | Published July 14, 2010 | 2 Comments |

It’s always a treat when I receive a crossdressing success story from the spouse or loved one of a crossdresser. The beauty of their acceptance is matched only by their courage in sharing their story.

If you’re the wife or girlfriend of a crossdresser, today I’d especially like to encourage you to share your crossdressing success story. It only takes a few moments to submit your story, but you will undoubtedly touch the lives of others in your situation. Even if you’re not fully comfortable with your significant other crossdressing, sharing your story of the first time they told you, or the first time you felt comfortable seeing her dressed would be a blessing to us all.

Meet Charlie

Hello, I’m Charlie. I just want to start off by saying that I am a woman. This is a short story about my boyfriend and sometimes girlfriend Veronica. How I came to find out about her crossdressing and how we are doing now. I hope this brings encouragement to other Crossdressers and transgendered ladies out there.

Charlie and Veronica’s Crossdressing Success Story

When I met Veronica, love just existed, like some outside force pulled us together. When I started staying over at his house I always noticed little feminine things, like the way he (at the time) sat, sometimes the way he looked over his shoulder and giggled.. in a way I thought of it as girlishly cute…

As time progressed our relationship began to get a little rocky, we actually were in an argument when he told me “I like to wear womens lingerie sometimes”, I responded with a surprised, “what?!”. He then proceeded to yell, “I’m a cross dresser”. At first I was in shock, I had never encountered anything like that before. I was a bit distant for the firstday or so, I had to collect my thoughts and figure out whether I could handle a crossdressing (he also admited he was bisexual at the same time) boyfriend. I decided I would try because I was verr in love with him.

I had a lot of questions, and he was completely open and honest with me. I began to feel more comfortable with the idea of my boyfriend in panties as we continued to talk. Eventually I looked at pictures and to my surprise, he looked verry sexy in drag. To be honest I was a bit turned on by his provocative debut.

I decided that him and I should go shopping and buy him some things. Our shopping trip was a bit frusturating for us in the fact that he was nervous and I didnt know what to pick for him. (just a tip: work out a plan if your not ready to be open with your transness yet). When our shopping trip was over he dressed up for me, and I realy liked it.

We have had other personal troubles but her crossdressing has actually brought us closer. I love the night’s when we are not us as the world knows us. I love getting her dressed and doing her make up and turning my boyfriend into my beautiful Veronica.

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If you’d like to look better as a woman I encourage you to try the world’s best crossdressing guide –  I guarantee you’ll learn a thing or two about passing as a woman and enhance your feminine image!

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Sometimes I Think The Stares Lead To Acceptance

By Vanessa Law | Published July 7, 2010 | 5 Comments |

I was moved by the sentiment in this week’s Crossdressing Success Story. It’s not one of first experiences, or feminine perfection. It’s more powerful. It’s a story of courageous outreach born of a deep self confidence. It’s a perfect example of how to change the hearts and minds of others without even saying a word.

If you have a real life crossdressing success story you’d life to share, please take a moment to submit your crossdresser success story.

Now I’ll let Jill tell her story…

Jill’s Crossdressing Success Story

After reading your post on staring (Ed – stare at a crossdresser?), I thought I’d reply with my recent experience. My friend Gale and I were on our way to Milwaukee’s Pridefest celebration when we stopped at a McDonalds for a bite to eat (much cheaper than eating at the festival). We were both dressed to blend in rather than stand out but niether one of us speaks in a feminine voice and our baritone is a dead giveaway to our masculine side. As we ordered none of the counter people made eye contact with us but after receiving our meals we sat in a semi enclosed area to eat and chat.

The tee hees and whispers started as soon as we walked away from the counter. I guess the young people on staff had never seen a couple of Tgirls before because it seemed as if everybody from the counter, to drive through, to kitchen staff walked past our table to get a better look. Gale and I found it quite amusing but at the same time flattering for being noticed by so many. Most of the other customers didn’t seem to bat an eye in our direction but the young staffers showed a great deal of curiosity.

I don’t know how to label the looks and stares but niether Gale nor I felt awkward or uncomfortable, as I think the young staffers did. After eating, we continued on to Pridefest where we enjoyed entertainment by Patti Labelle. The festival started breaking up around midnight and as we drove back to my suburban community, my car died and I had to call for a tow. The driver was very courteous and treated us both as ladies, but I’m willing to bet he had plenty ot tell his co workers when he got back to his shop. Sometimes I think the stares lead to acceptance. Luv and Hugs, Jill

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Alice’s Crossdressing Success Story – A Lingerie Desire

By Vanessa Law | Published June 30, 2010 | 3 Comments |

Do you remember the first time that you heard the call from feminine lingerie? The imagining and anticipation mixed with fear and trepidation? In this week’s crossdressing success story Alice shares her first crossdressing encounter with lingerie.

If you have a real life success story you’d like to share, please take a moment  to submit your crossdressing story. I’ll share it with the other readers of Crossdresser Heaven.

Alice’s Crossdressing Success Story – A Lingerie Desire

Alice's Crossdressing Lingerie Desire

Alice's Crossdressing Lingerie Desire

I remember when I was about 8 or 9 finding out my feelings about wanting to be a lady. I remember my first touch of lingerie. I went over to a friend’s house early in the  morning. In those days we usually called out the name then went inside. Well I went inside and found out nooone was home.

Now I will admit there mother was kind of a single sexy lady back then. Anyhow I went inside and entered the living room. Lying on the floor was a pair of panties with soft nylons attached to them. I guess they were like panty hose but better. Next to them was a beautiful bra and slip. I reached down, touched them and immediately knew I wanted them so I grabbed them and ran home with them tucked in my pants.

I went into my basement examined them, tried them on and from then on I was hooked. I would take any chance I had to to get more lingerie off clothes lines, laundry baskets etc. Today I am a full crossdresser, have more lingerie and dresses than a gal needs and love them all – Now if only I could find a girlfriend to share things with oh well sweet things to all.

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