I am a very shy and keep-to-myself man. But when I let Holly out, she’s everything I want to be but not allowed to be by society! Playful, sexy, cute, girly, silly, loud, daring, etc! Normally this girl is very much kept in the closet…well, this girl went temporarily running and screaming out of the closet one weekend…terrified the whole time, but I actually did it!
I made a very big step and approached the voodoo topic of my other side with my wife. For the first time ever, it went well. It was still awkward, but for once I kept going instead of letting it just shut down. We both dumped our feelings on the table and as hard as it was, it was open and honest. At the end of it all, we both were still smiling, said we loved each other and hugged and kissed. I was empowered by the fact that after a talk with her before leaving for this business trip, she said that she knew I would be dressing up while away. Knowing for once that I wasn’t “sneaking” around was SUCH A RELIEF!
Finding no one to go with me to a club or bar, I went out shopping instead! Granted, I started slow and went to Target…in my knee-high boots to go with my favorite black flowing semi-short but tasteful skirt and a very cute tight red top (can you see me smiling!). This outfit is now the first skirt/dress I’ve ever worn out in public! What a feeling! I’m such a girly girl, but the couple quick times I dared to go outside, I always went out in tight jeans because I was scared.
The last time I was out in California, though, I went to a CD store and had a wonderful time purchasing a lace front wig…what a difference that makes! For once I felt like I didn’t look like a guy in a dress, but rather the fairly attractive, extremely tall blonde woman I’ve always hidden away if I do say so myself 😉 I had so much fun strutting my stuff around Target in the women’s section and then the makeup section that when I left, I decided to keep on shopping!
I went out to a far more adult-themed store looking for a new corset as my last one just bit the dust. Unfortunately, they didn’t have any, but regardless I had a wonderful time browsing and talking with one of the sales girls who was very nice to me. Finally, I went out to Ross to look for new dresses. This was the first time I’ve ever shopped there, or really anywhere, while en femme…what a different experience! I was able to hold up dresses to my body out in the open without feeling weird! I picked out five dresses and walked to the dressing room.
Now…this is where I have a past. I have taken dresses to the dressing room and had two VERY different experiences. Ross makes you hang up the items out in the open. The first was wonderful…no judgment, and I confidently took the 3 elegant dresses back to the men’s dressing room. The second time was horrible…far more crowded, but emboldened by the first experience, I took a couple dresses up to the dressing room again. This time, the woman was argumentative, judging, and made me feel horrible! Never the less, I didn’t back down (even though I almost had a heart attack in the process) and after making a huge scene that I swore would go viral on YouTube, I walked back to the men’s dressing room with my dresses…and in the end bought one just to make a point to her!
So, now coming back to this trip, I walked up in my cute outfit on my first semi-confident real night out en femme with my 5 dresses and presented them to the woman at the dressing room. She gave me my tag without issue and I went to turn left into the dressing room because I thought it was the woman’s….well…it wasn’t! To my great surprise, she stopped me! She said, “No miss, this way”, and directed me to the women’s dressing room. I’m fairly certain she made me out and was a little uncertain about how to handle it, but in the end, she was perfect. I really can’t fully describe my thoughts as I walked in. All I could think of was I was accepted! I tried on all of those dresses, took pictures, and even walked outside of my stall to look at myself in the big 3-way mirror to get a better look…as well as to simply strut my stuff! 🙂 I, unfortunately, didn’t buy any of them, but the experience was amazing.
Fast forward to the next night…I was confident…I was excited…I wanted to go out again…so I decided on the dress that I had targeted as the first dress I would wear out in public! (Seriously, what is going on with me?) So I did all my makeup, which thankfully I haven’t completely lost my touch after a long hiatus from “Holly time”, put on my dress, and then my wig. I must say…I adore this outfit and want the world to see me in it! It is just so feminine that I love it!
When I went to open my hotel room door, I paused…again…scared about going out in public in a dress. I couldn’t let this chance pass…I opened the door and left…went to my car…and found a flat tire! SERIOUSLY!! Well crap, now what? There was no way I’m changing a flat in a dress that doesn’t come to my knees!
Ok…back to the room, change into my “manly clothes”, but put a hat on to attempt to cover the fact that my face is completely done up en femme including one of my best sexy lips attempts! There’s no way I’m wiping that off! I go back out with female face, but male clothes, change the tire, start putting things away when another man comes out to ask if I need any help…PANIC!! “No I just finished!”…”Wow, perfect timing!”…and that was that…in hindsight, I feel like a jerk for not thanking him for the offer, but I was too busy almost climbing into the trunk to hide my “perfect” face!
Ok…swallow heart…alone again…quickly put everything away and walk back inside. Ok, I didn’t go through all this to just cower in my room, so I put my dress, wig, and heels back on and went out! Granted I only got a takeout salad at a pizza place and then went back to Target to buy a bottle of wine for myself, but still, I was strutting around in my dress and having fun with it!
The priceless point of the evening was when I got carded for the bottle of wine at Target! The girl asked for my ID and I handed her my male ID. I felt sorry for her because she looked so shocked that she wasn’t sure what to say! I just smiled at her and kept talking (in a voice that definitely needs work…remember, never been out in public before!) She was a trooper and finished checking me out. I then got back to my room and realized I only had plastic cups, so I pressed my luck and walked to the front desk in my dress to ask for a “glass” glass for my wine! Again, I was amazed that I was completely accepted and treated as a woman.
All of this has shown me that I may not pass if people look closely, but even when I don’t, people accept me for who I want to be or who I decide to present at the time. It was a horrible travel weekend full of flight issues, lost bags, feeling ill, no sleep, etc, but it had been one of the most amazing trips! For the first time ever, I let Holly truly out in public dressed as the girl she was meant to be and I had no issues…other than my boots being too tight after 3 hours of walking around, but what’s a girl to do? 😉
The world may not fully accept us or understand us…heck most of us don’t understand us…I know I don’t fully yet, but I was accepted, treated wonderfully, and I couldn’t have asked for anything more. I wish the same for every other girl looking for their first opportunity to let their true selves out to play!
Holly, what an inspiring story. You are a courageous person, daring to live your life as who you are, not what society thinks you should be. A lesson for all of us. I myself am just getting nerve to wear panties under my man clothes. But, one step at a time.
Thanks for sharing,
JaiymeLynn
Thanks JaiymeLynn, I’ve been through quite a number of stages through this and many times it’s 2 steps forward, 14 steps back! The important part is finding friends to talk to and being comfortable with yourself. CDH has been wonderful for me in that regard!
Holy crap Holly! That was an awesome article! I can’t believe you are the once shy girl I met right after joining the site three years ago! You gotta come visit me soon, girl! I am SO happy for you! No one can stop you now!
Hugs,
Cyn
Thanks Cyn! I almost didn’t post this as it happened back in the Spring and since then found out that the conversation with my wife was not as perfect as I had thought. Regardless of the aftershocks I’m dealing with, this was such a wonderful, amazing, and at times funny experience that I decided I still wanted to share with everyone. It still makes me smile thinking about it. 🙂
What a great article!!! Holly like you I am a shy keep to myself guy. I would never ever wear shorts or anything that would draw attention to myself. But Daniella is fun flirty girly. Loves high heels, short summer dresses and loves to experiment with makeup. Someone has already commented on being our own worst enemy and it is so true. We believe everyone is looking at us. Something bad is going to happen when we step out. I remember I was walking down a street and a couple just ahead of me had stopped and they were talking… Read more »
Love it Daniella! Like you said, most people really don’t seem to care or notice if we’re simply trying to blend in. I need to update my dress collection so I have more options to go out in like this when I get another chance because that was WAY more fun than the few times I ventured out in tight jeans!
Hello Holly and thanks for sharing It’s certainly hard to describe the thrill and satisfaction of stepping out and you seem to have nailed it . I think when your stepping out into the " role " , it’s the degree of preparation and the confidence in which one presents that makes the difference . It’s also about being streetwise , sober , straight and aware to advoid , at best , embarrassing , and at worst ,dangerous situations . For the time being at least , there is still a highly intolerant , insidious element in society that one… Read more »
Holly- Thanks for sharing that crazy evening. I love your perseverance and attitude. If we could only bottle that like the wine we both enjoy. I know it seems like “the rest of the world" is waiting for us to screw up, but most of that is probably somewhere in our acquired inhibitions. WE SHALL OVERCOME these inhibitions, Holly. You are well on your way… and I’m still back a ways. Love to you. -Lara
I’m definitely not all the way there, but this one week everything seemed to align…even if I had to deal with a flat tire! You’ll get there Lara! Hugs!
Great story holly you motivate me good luck in the future. I hope to find joy like that some day with someone
Thanks Michaelle! I hope you do to!
Thanks Holly, a great story to share! I feel the inspiration!
What a great story Holly. Also to have an understanding wife.
Holly, I absolutely love your story…so much so I read it twice. I want to get out so bad but I still don’t have the confidence in my looks to do it yet. I’m about 10-15 lbs from my weight goal, I work on my make up a couple times a week, that is hit and miss but I’m at least getting it done faster than I was before (down to an hour now) and I work on my voice daily. I haven’t decided what I should wear, every time I think I have it nailed, I take pictures and… Read more »
You’ll get there Erica! Something about this dress called to me when I found it. It was just 100% my style and made me want to show it off! It accented the good and not the bad which is what every girl wants, isn’t it? 🙂 Somehow the makeup gods shined on me that weekend too because I haven’t been practicing as much as I used to, but somehow I was able to pull off a very understated, but still evening style look that I felt very confident in. I’m confident I didn’t pass all of the time, but I… Read more »
Holly thanks so much for replying. I still haven’t found that “magic" dress or outfit I feel confident in. I think I could do a half way decent make up job if I took my time. I still have a long way to go in a feminine walk, I know I have to stand straighter and have the confidence in my look to convince other I am what first glances should tell them I am. I have made some friends here recently and they are in about the same “place" I am. Although they are miles away I am hoping… Read more »
Thank you Holly for such an inspiring story. I’ve never had a problem with the dressing room but do make it a point to avoid interaction with any other customers. And what timing it is with the flat tire. I don’t know what I would have done if I had to fix a flat. If I was at the hotel I think I would have gone back and changed to my ladies jeans and a T-shirt or something casual, but what if I had to do it in my dress and heels. I suppose I wouldn’t have had any choice.… Read more »
Trust me Stacy…I went back and forth on how to handle the flat a LOT that night. I still can’t believe I timed it just right that I was covered before that nice man came by to help me! I can’t imagine what his response to my dolled up face would have been!!!