My story is probably like many of you that have gone before me. I have been cross dressing off and on since I was 12. I got married and had a son doing what is normal for a guy, but even though I suppressed my feelings for dressing, they were always there. I would dress when I was out of town for work and I have gone out mainly at night in the car driving around. Yes, I mainly dressed for myself in the closet. My feelings when I dressed were becoming stronger that I really love being Cheryl and my personality both dressed as Cheryl and when I couldn’t dress definitely shows my feminine side. Cheryl is definitely taking over my thoughts. My desire to go out as Cheryl has been brewing for years and I finally worked up to where I needed to get out.
My story is probably like many of you that have gone before me. I have been cross-dressing off and on since I was 12.
I got married and had a son, doing what is normal for a guy, but even though I suppressed my feelings for dressing, they were always there. I would dress when I was out of town for work and would go out driving the car, mainly at night. Yes, I mostly dressed for myself in the closet. The feeling that I really loved being Cheryl when dressed was becoming stronger, and my personality, both dressed as Cheryl and when I couldn’t dress, definitely showed my feminine side.
Cheryl is taking over my thoughts. My desire to go out as Cheryl has been brewing for years and I finally worked up to the point where I needed to get out.
We have a local store in the Chicago area called Transformations by Rori, that hosts a TG party at a local bar. I have thought about going to that party for years but I have chickened out more times than I care to mention: Last Thursday, I finally worked up my courage to go there.
I got a hotel room nearby so I could dress since my wife does not outwardly acknowledge my dressing (I think she knows since she suggested that I pierce my ears). I selected my blue dress, to wear with nude hose and black heels. I wore my blue dangle earrings and matching necklace. I even changed the band on my Fitbit to light blue for the occasion!
I was really nervous, but when the time came to leave, I put on my puffer coat and out of the room I went.
It was a cool night at about 38 degrees with a slight breeze. The feeling of the night air on my legs was amazing as I left the hotel, hearing my heels click on the pavement.
I drove to the parking garage and took the elevator down. When the door opened, a woman was getting on as I left; she said ‘hi’. I returned the hi in my best Cheryl voice; it was a nice interaction.
As I walked down the street to the bar, I passed several people who did not really seem to care. I walked into the bar, found the group and was welcomed immediately. I introduced myself to everyone.
It was a wonderful evening talking with the other girls and to think that I was so nervous about going. There were several girls that got up to dance to the music being played on the piano, with everyone enjoying themselves. I didn’t dance this time, but I definitely plan to go there again, to dance and let myself go. My fun this time was just meeting everyone and talking.
Now, I need to plan my next outing. Something I have always wanted to do is go shopping dressed as Cheryl as, so far, shopping in drab and Amazon has been the norm. I think this is going to be my next adventure which I will try to share. I have started getting leggings and flats for the shopping trip; I am hoping that I can do this soon.
I hope this article will help someone realize that going out may be scary, but it is well worth it. It took me way too long!
Latest posts by Cheryl (see all)
- Cheryl goes out for the evening - April 17, 2025
Good for you Cheryl! You are sitting next to my “big sister" Kendra. I just went out first time last weekend.
@Aria Faraci Aria, it is good to hear that you went out for the first time. I hope it was a great experience.
Yes, very good! The Oak Brook Girls Night Out Social is a great event for a newcomer.
@Aria Faraci Aria, I will need to look that up. I think I saw that it is on the weekend.Â
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Look for calendar on Transformations.com
after reading Cheryl’s write up it dawned on me that it would be great if CDH developed some kind of resource directory to allow those wanting to venture OUT for the 1st time an awareness of places in the USA where they would be comfortable and accepted
@emilyfÂ
Hi, Emily, I just noticed your post and don’t know if you’ve seen this already but you can search by location. These places are compiled and verified by members.
https://www.crossdresserheaven.com/local-places/
Allie x
@emilyfÂ
We’re building on the Local Places directory all the time, so it’s worth keeping on eye on it. I added over 500 localities in March this year (mainly for the UK, Europe, with some in Canada) and the US localities are building at a similar speed 🙂