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.

I am an above average intelligence, decent looking guy with a “special” personality, the latter I would regard as the best thing I’ve got going. My personality… I don’t really know how to describe it well. I possess both very masculine and very feminine traits and normally I present slightly to the masculine side, depending on who is around. I am very good at controlling which side is expressed. There is more to it than that, but I guess you’d really need to meet me to understand.

Like a lot of people I suppose, I started “experimenting” when I was young. I can’t really give you the year, my childhood was quite hectic. Owing largely to my circadian rhythm disorder and being “forced” into a time cycle foreign to my body, everyone was convinced there was something “wrong” with me. Though I possessed the intelligence, I horribly failed in school after the 6th grade because I was constantly sleep deprived, angry and confused. Because of this I spent much time in and out of psychiatric hospitals, force-fed medications like Thorazine, Haldol…( you name a psychiatric medication and they probably gave it to me) that did incredibly atrocious things to me, all culminating in a 2 year long stay in a psychiatric hospital that will remain unnamed. I could write a book on what they did to me or I could write a single word: TORTURE. But most importantly they taught me that “it is not okay to be who you are.” Well, they tried. Through God’s grace they didn’t break my personality, probably because I saw so many other people suffering in the same way and knew just how horribly wrong it all was. I could see that many these people sharing my situation were as “normal” as anyone, and through that I held on to myself as being a “valid person.” Of course there were very sick people there, with schizophrenia or worse.

But it was no better for them, in fact worse. They WERE sick and yet they were being treated like… I don’t even know. Less than human. Less than an animal. Less than a life. A very select few employees of that place were different though. They saw how horrible things were for us and did everything they could without losing their jobs to make it easier. It’s amazing, when basically everyone is telling you that you are “bad” and “broken,” the effect that one sentence by someone who truly cares can have on you. These special people are largely why I am still a human being and not a drone. Eventually, since I would not be broken, they discharged me as “untreatable.”

Obviously I wasn’t crossdressing in that situation per se, but I developed an incredibly elaborate fantasy life, including the persona Jessica, who actually wasn’t named until a few years ago. I still maintain this fantasy life to this day, when I lay my head on my pillow at night, I’m somewhere else ‘til I fall asleep. Sometimes as Jessica, sometimes as Josh.
After that, I was forced into a group home 3 days before my 18th birthday. The day I turned 18 in that group home I called my mom and said “Come get me or I’m signing myself out.” I came home, weaned myself off of those medications and said “Goodbye!” to that world. Now free of that horrible fate, initially I fell into a state of confusion and despair. I didn’t know how to live without being told what to do. My mother was rarely home, and I was left to my own devices.

I experimented with a lot of things in a lot of ways, things I would normally have done at a younger age had I not been in “that place.” One of these was crossdressing. I fell in love with it immediately.  I loved the way things felt, looked, moved, everything. I also loved that it was “wrong,” because it would be quite a few more years before I accepted myself. It was my secret, my rebellion, my way of saying “you can’t control me.” My resources were limited, both mom and I were and are on disability, and financial responsibility fell to my mom, who used the extra money to gamble.

So, I stuck to stealing her clothes when she wasn’t around, or even when she was sleeping. Neither then, nor now, have I ever been “caught,” i.e. seen as Jessica against my will. This continued for a while until gradually, my mother learned I was not as “crazy” as everyone thought. Eventually I was basically accepted to be a “person,” I know how ridiculous that might sound(or maybe not). It wasn’t long after that that I decided to buy my first outfit.

With my debit card I ordered some stuff online, only telling mom after the fact. I only told her what I spent and that I was going to be receiving a box and she’d better not mess with it if it came while I was at college. Well it did come on a school day, but I managed to capture it before I left. All day I dreamed and fantasized about it, and when I got home, though I had figured my size horribly wrong(lol) I knew then that this was going to be a part of my life forever. I was beginning to accept it as part of myself, but I still felt “delinquent” when I dressed.

Eventually, my mother’s overbearing behavior really started to get to me, and I “ran away” so to speak, [even though I was 23] and came to live with my sister, near where I reside now. My sister and her family were greatly accepting of me, and it wasn’t long before I confided her (and my 10 year old niece, children are so wonderfully accepting and honest) about what I liked to do. Things stayed good for a while, and it wasn’t uncommon to find me around their house wearing some sort of makeup or something. But I had made my sister promise when I moved in that if I ever became a burden, or started to cause inter-family problems for them, to tell me and I would leave. Since mom still had financial control over my disability check and refused to give it to me because “I had betrayed her,” I made a significant dent in their finances.

Not really because of me, but because of many factors, my sister’s family fell behind on their house. My sister approached me one day and told me how her husband had complained about me and how even though I wasn’t doing anything wrong I was still a financial hardship. That day, I packed up and left, even though the family, including her husband, begged me not to. I moved into a trailer in a small town nearby. Meanwhile my mom had gotten to the point where she could just not live on her own.

We moved back in together, in the apartment we currently live at, but things are much different than before. Staying with my sister and being allowed to be myself granted me confidence, and I no longer allowed myself to be controlled. Once mom realized this, we developed a positive relationship, one I’m glad to say we still have.

In the end, it turned out that in order to accept the part of myself that wanted… needed to crossdress, I needed to accept myself. Period. Roughly two years ago for the first time I looked in the mirror and liked what I saw. Not my physical appearance, but my soul, my personality. Me. I had amassed a decent collection of clothes and makeup by this time and spent quite a lot of time as Jessica, now named because she was now part of me. One night I decided to go into my backyard and sit on the swing while I was Jessica. It was perfect. I enjoyed it immensely and hated the fact that anyone in the world would dare look at me sideways for doing it.

After that, I got tired of sneaking around my own home and with mom’s deteriorating health she was increasingly present. So here it is. One day we were working in the kitchen and mom decided to share a very deep secret with me. And I knew it was time. I had no idea how she would react, I was terrified, so scared I was shaking head to toe. I had only told her I was going to reveal my biggest secret, so we should go sit down. I think she seriously thought I was going to tell her I killed someone lol. Slowly and while staring out the window, I told her about Jessica. I explained everything I could and told her to ask anything she liked. She asked typical questions like “When did you start?” “Are you gay?” “Do you think you should have been born a girl?” etc. I answered them all.

But here is where I knew she really wasn’t putting on a front: she asked me “What do you wear?” and I told her of my favorite ivory white party dress. Then she said “Can I see it?” So I fetched it from my closet and presented it to her like a child with their favorite toy. She said to me “Oh, that’s so pretty.” I was floored, I was expecting to be rejected almost completely, being told to keep it to myself. Instead she went on to ask me where I bought it, how I learned to do makeup etc.

From that moment since, I’ve been free to spend my time in the house as whoever I want, Josh or Jessica. Mom once commented on just how well my face transforms. And it really does. My face is definitely a guy’s, but only just. Properly applied makeup and my shoulder length, extremely dark brown, naturally curly hair pretty much finishes the look off. If only the REST of me would comply with my wishes that well… Anyway, when I’m not suffering from back pain, I would estimate I spend 40% of my time as this “other person.”

But here is the thing. Josh isn’t me. Jessica isn’t me either. They are both parts, and only together do they become “me.” Only gradually am I incorporating Jessica back into Josh, but I will always crossdress and let Jessica shine on her own: she is beautiful and special and she needs to be shown to everyone. But not just by literally letting myself be seen as her, but also through the personality I present regardless of “who I am” at the time. Whet
her I set foot out of this house as her or not, she is always there, whether in something I say or how I smile. Am I a boy? Am I a girl? Am I gay? Am I straight? The answer to them all is “I am me.”

It surprises me how powerful that statement is. ”I am me.”  I say it often. Once I had told my mom, everyone close to me then knew and they all are fine with it, often even encouraging me. One of my friends in turn told me of his experiments after learning of mine. Another simply told me, as long as it makes you happy then its right. I’m truly blessed to know these people. I’ve always been honest with them and because of that, when I told them about Jessica, they knew I was completely serious. Sometimes they poke fun at me and I usually respond with something only Jessica would say, which is always a good laugh for us. After so many years and everything I went through, it’s great to be free. But there are still hurdles.

A year ago I sort of stumbled on to my first real chance to “walk out the door” as Jessica. Me, my sister and her family were sitting around their table discussing Halloween, a holiday that always turns out to be great fun for us because it is free of what I call “the family BS” that holidays like Christmas can attract. I was originally planning to be Squall from Final Fantasy VIII when my sister suggested “You could always dress as a girl.” I said “Yes! I will do it!”

I could think of no easier way to show Jessica to the world than on Halloween, when all but the most ridiculous people would think little of seeing her. My sister then decided she would dress as a guy, and we would make a big deal of the whole thing. We would have, too. My niece was rather excited as well and told all of her friends that would be with us that night. Because she knew that there was nothing wrong with it, she thought little of telling anyone. Oops. After telling one of her close friends, that friend told their parents. The parents were shocked, floored, disgusted. They called my sister and said if we crossdressed then this friend of my niece would be forbidden to see her ever again. Such stupidity.

Of course, I refrained from dressing that night for my niece’s sake, but you know what? We went to the mall towards the end of our Halloween and what did we see? A man dressed as a woman(and not very well, Jessica is so much prettier…lol…). And you know what? That little girl, the friend of my niece – she wasn’t suddenly converted into some sort of demon by seeing a crossdresser. I wonder if she told her parents.

I’ve often heard it said if you accept yourself then the world will accept you. There is truth in that, but it is not the rule. There will always be people who attempt to cast you out of society. They will do it for any reason you give them. They’ll do it if you’re gay, if you crossdress, if you’re black, if you have a funny accent, if you’re Jewish, it does not matter. The second you align yourself with one group, you will be ostracized by another. But you know what? You are you. God made you. God doesn’t make mistakes.

Sometimes I wonder, (oh do I wonder!), why God made me the way He did. Some parts I love, some parts I hate. Sometimes I scream, even curse at Him saying “Why the F*** did You make me like this?” But I’m not referring to crossdressing. When I pray, I used to tell God I didn’t know if it was right or wrong to crossdress, but if it was, to forgive me. Now I say “Thank you.” God gave me this gift so I could express myself entirely, not just
what society wants to see. And yes, I know the few passages in the Bible on the topic are quite negative but here is my take: How many atrocities have been committed in God’s name? Just because you invoke the name of the Lord doesn’t mean your actions are condoned by Him. The Bible, though intended to be God’s word was written by MAN. And it has been translated… oh so many times. People are biased; they put their spin on things. The Bible is not exempt from this.

So if society at large is biased, and the Bible is biased, how do I know that it’s okay? I can feel it in my heart. If I lie, I can feel it is wrong. If I steal, I can feel the guilt. If I crossdress, I can feel the sun shine upon my soul. If God Himself comes to me and says crossdressing is wrong, then I will believe Him. Short of that, no person will come between Jessica and I. So that’s my story. Not only did I come to accept myself as a crossdresser, being a crossdresser helped me learn to accept myself. The person I feared most, was one of the most accepting. I know it can’t be that way for everyone, but for me… it was.

~Jessica

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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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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!

Other Transgender Posts

• Cross Dresser Success Stories: A Menagerie Of Stories (2)
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• A Sex Change at 7… (1)

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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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

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.

Other Transgender Posts

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