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.

EnFemme

More Articles by Jennifer Connolly

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    Cassie Jayson
    Duchess
    Trusted Member
    1 year ago

    Jennifer you said again the feelings I have for CDH. Can’t believe your 71, you don’t look a day over 50. For me if it hadn’t been for 2 things I wouldn’t be where I am today. First when my X found out she told our 3 grown kids and threatened to tell my 4 brothers. So I told my brothers myself and been telling others in my life a few here and there and have had no bad push back yet. The second was all the wonderful girls here and all their adventures, I so wanted to get out… Read more »

    Nora Grace Fergason
    Lady
    Member
    1 year ago

    Hello. I just wanted to send a cherry hello to all you lovely women out there. In one of life’s flukes, I think this site is in the U. K., but I got to make an aquitance two miles up the street. How funny is that. During Pride Week, we went out for her first time EVER!!! She talks about it even recently. Another quirky thing, she heads up the LGBTQ + group where she works, & always wanted to venture out, as a woman, but didn’t have a crazy woman like me to say, “To heck with them, we… Read more »

    Last edited 1 year ago by Nora Grace Fergason
    Lucinda Hawkns
    Lady
    Trusted Member
    1 year ago

    you look absolutely stunning, why not go outdoors and have a great time, no one would know it’s a man dressed up and no one would recognize you so why not go to a party with others near you and have a good time infem. i went to a Buffalo Bells meeting years ago and i was a little scared but i did go in but at first it was the wrong room, then i found the right room and sat down and all the ladies were very under standing and welcomed me to the meeting, we each had a… Read more »

    Ambermaria Martinez
    Lady
    Active Member
    1 year ago

    Hello Jennifer I must say yes the name does fit you very much my name is ambermaria my mom gave me that name when I first came out to her her middle name was Maria and I always loved the smell as Amber I’m very very happy with being a cross dresser my self And how wonderful it is to be a cross dresser but I not just another cross dresser I want to be a woman also I feel much happier in life as ambermaria I’m now 67 and I believe it’s time to let the world know I… Read more »

    Baily Marie Lovejoy
    Lady
    Active Member
    1 month ago

    I loved your story of your CDH beginnings, Jennifer. New girls just joining should be directed to this story. It’s very inspiring to read those words.

    I’ve seen your pics on here for quite some time and honestly would never have you down as someone in their 79’s. WOW girl. Definitely a 50 year old woman is who I see.

    I’m so glad we have girls like you to inspire all the future girls who just aren’t sure.

    Enjoy your day sweetie.

    Baily 🎀💁‍♀️🎀

    Nicki Johnson
    Baroness
    Active Member
    1 month ago

    Jennifer, you have summed up beautifully what most of us here have gone through. Unfortunately we are our worst critics and I am the same way. I always question my photos and it’so nice to get another perspective. The positive encouragement on this forum is overwhelming. It is such an uplift to have our photos looked at by someone other than ourselves. With that said, I want to repeat what I have said in the past. When I look at your photos I see a beautiful woman who is happy with herself. You always have such a lovely presentation and… Read more »

    Elaine
    Duchess
    Active Member
    1 month ago

    @Jennifer Connolly thanks for sharing Jennifer.  CDH has been a great experience for me also.

    Denise Smith
    Lady
    Active Member
    1 month ago

    @jennconn Thanks for posting Jenn. You have echoed so many of my thoughts about CDH. Please don’t underestimate the inspiration and support you provide. I’m so glad you’re here.
    Denise

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