On November 28, I joined Crossdresser Heaven. I had been crossdressing for a long time, but had never embraced it fully
I really didn’t know that much about CDH when I joined, but I immediately came to understand what it was all about. Just the thought of even revealing myself to anyone was terrifying to me. So right after I registered, I received my first private message. I thought to myself, a private message, this can’t be good. So I opened it, not sure what to expect. It was a very welcoming message from a member here who was wondering where in the state I lived. I hadn’t revealed that in my profile, since I wasn’t comfortable with anyone finding out where I actually lived. But upon finding out that I was close, she invited me to a Christmas party. In my mind, I thought how I had always dreamed of doing something like that, but of course there was great apprehension on my part since I wasn’t at all comfortable with my presentation to be able to go out. So, I declined the invitation, but got a friend request so I could learn about future events. I thought to myself that I had accomplished 2 firsts, one that I had just revealed to a complete stranger that I was a crossdresser, and accepted my first friend request.
So, I was contemplating where all of this was heading, and thinking to myself, “what am I doing here, there could be all kinds of different people here to out me”. But then the next day, I received posts to my introduction from fellow girls here that welcomed me, and let me know how it was a friendly, open and non- intimidating place to be. So I was convinced by them to stick around and see what this was all about.
The next big thing for me was thinking about posting a picture. I had been looking at all the gorgeous pictures that everyone posted in the photos section, and was very impressed with everyone’s presentation. But being self-critical of my female look, I had a really hard time picking out a photo. Then after I finally found one that I liked I posted my first public photo. Within minutes, I was so afraid of this photo being downloaded and shared on the internet, that I immediately deleted it.
From here, I started to read and post some responses on discussion forums, and was excited to participate. All along the way, with the forums, I received encouraging posts from members here, and slowly realized that there was nothing to be concerned about. So I decided that I could upgrade my membership and at least post a picture in the private photos section. It was difficult to choose a photo, since I really didn’t like any of them, so the one that I picked was one where I changed my wig to a longer style through Faceapp.
By posting in the private photo section, I didn’t have to worry about the exposure to the entire world on the internet. Then, as I posted some more on the forums, I received a few messages about the photo that were very encouraging. Some said that it actually looked really good. Some even wrote comments on the photos about the picture, and I was beginning to think that maybe I could stick around on CDH and with a lot of work, get my look down so I at least would satisfy my own critical self and feel good about posting more pictures.
I didn’t have any more opportunities to dress during the holidays, but I couldn’t wait to get to try my next presentation. I really liked the hair that Faceapp had put on me, so I searched for a new wig that might fit the bill. But by then I had read that using photo manipulation wasn’t really fair if you wanted to present an accurate picture of who you were. So I replaced the manipulated photo with the original. Surprise, surprise, I got the same type of comments about that photo without the long hair. So I was even more encouraged to try to perfect my presentation.
Then my search for the hair that I wanted seemed to be over, and I had ordered a new wig to match what I thought would be a good look for me. I was excited when it arrived, and couldn’t wait to try it on. So I opened it up, and put it on. When I looked in the mirror, I thought I was seeing Wayne from Wayne’s world, and was ready to send it back. But I remembered that several people had complimented me on a picture of a new dress with the old hair. So I decided to at least get dressed and see what the wig looked like with that dress. The next time I looked in the mirror, I was a little more encouraged. I decided that I’d try a little makeup to see what it was really like. Then to my surprise, I really began to like the new wig. Wayne from Wayne’s world was gone and replaced by a decent looking woman. So off for a few more pictures. I liked a few, but wasn’t that happy with makeup, since I hadn’t taken the time to do it properly. But the pictures were good enough to post. I actually got a few positive comments from friends that they liked the look.
Then last weekend, a new dress arrived and I was excited to give it my best effort. I took my time on makeup and thought that it looked pretty good. So I proceeded to take some more pictures. I saved the best ones, and then realized that there was one that I really loved. I could see nothing in that picture except a woman, and plucked up the courage to post it publicly (my first). I decided that even in a public photo, no one would ever suspect that person to be me. Then I decided that I liked it so much that I sent it for consideration for featured photo. The next day, I was shocked to have been chosen. Me, the brand new know nothing newbie, being selected for featured photo on crossdresser heaven. You can’t imagine how excited I was. But my excitement didn’t stop there. There were a bunch of positive comments posted on the photo, which made me even happier. After all, I hadn’t been at this very long, and wasn’t very sure of myself and my new efforts to crossdress.
Later I received an even more encouraging private message from a friend here that had let me know how much I had influenced her through our communications here. I never thought that it could happen to me that I could have a friend who I could help to crossdress. What a treat for me.
To say the least, it was a very good day for me to have affirmation from members that I could look good enough to actually look like a real woman. I’m so happy about it.
I just wanted to write this article to thank everyone here that has responded to my posts and provided words of encouragement to me in my journey with this wherever it leads. I no longer feel alone in crossdressing, and am very thankful to be a part of this sisterhood. I am looking forward to posting more, and hopefully even better photos in the future. Thank you all you have been incredibly supportive.

More Articles by Jennifer Connolly

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    Roberta Broussard
    Trusted Member
    1 month ago

    Hi Jen,
    Thanks for putting to words what I think most everyone here has encountered. I too am new to all of this. Since joining CDH, I’ve noticed one of the most interesting thing about this site is the overall willingness to help others. I’ve seen many new members come in being ever so shy. Then watch how they blossom to full fledge Big Sister to so many others.
    It truly is the best.

    Lucinda Hawkns
    Trusted Member
    1 month ago

    Hello Jen if i may call you Jen. you look absolutely stunning, yes no one would know it’s you for you look different dressed up in that pretty outfit, you have the figure of a female may i say so. too bad about the Xmas dinner that someone asked you to come too, you would have had a great time with the rest of the girls and enjoyed yourself. i went to a Buffalo Bells meeting years back and i had a great time, we all talked about our self-one at a time and it came up to me to… Read more »

    Angela Booth
    Active Member
    1 month ago

    Schwinggggg….Party on Jen. You look just fabulous, Thank you for an insight to Jens World…...

    Michelle McQueen
    Active Member
    1 month ago

    You look great and I’m glad you decided to stick around. I look forward to reading you on the forums dear. This truly is a sisterhood and this is the best site I’ve found for support and encouragement. All of us need to know there are many more out there just like us all over the world and its not a crime to enjoy our passion but its just who we are and thats ok.

    Michelle Davis
    Active Member
    1 month ago

    Thanks for sharing your CDH journey. I have seen your confidence grow just in the short time we’ve known each other and I’m glad to be a friend.

    Noble Member
    1 month ago

    Jennifer, this is such a wonderful article and so true! It perfectly describes my own journey here on CDH – hiding my face on the first few photos that I posted, terrified that I would instantly be outed, fearful that I did not measure up to all the gorgeous ladies posting photos here. Gradually I worked up the courage to keep going beyond those initial stages. This is such a fantastic supportive community – it is really unique that way. Please know that you are in the right place to express the woman in you fully and openly – you… Read more »

    Active Member
    1 month ago

    Thank you for sharing your story Jennifer! You look good!

    charlottejane ross
    1 month ago

    very intersting but dont have any worries you pic is perfect xx

    Twinkie Brashear
    1 month ago

    Hi Jen!
    Many, if not most of us, have experienced what you spoke of. We all get better with our dressing over time. Who knew that learning how to be a girl could be so complicated right? 😉 You look awesome in your photo btw! God bless you on your journey to femininity…

    Michelle Rich
    1 month ago

    Jennifer, when I saw your photo I saw a pretty WOMAN. You really knocked it out of the park girl. I wish I looked as good! But then again I am 150 and you are 30 right? lol. Welcome to girl heaven for those of us who discovered our alter ego. Like you, I hesitated. But its become a bigger part of me. I love my fem side and spend as much time as possible that way. It destresses me. I am calmer on the phone when dealing with a crisis if I am in fem mode instead of drab… Read more »

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