Crossdressing Storieslatest

My Last Day as a Crossdresser

Last day as CrossdresserBeep. Beep. Beep.

I rolled over and took a big sigh. “Todays the day, buddy.” I said as I pet my dog. “Let’s go potty.” I rolled out of bed and put whatever clothes were sitting on the floor. Then I grabbed his leash and took him out into the yard.

When we came back inside, I went straight to the bathroom and started getting everything in order. I grabbed some tweezers, my manscaper, some razors, and a can of shaving cream. I quickly started to work on my eyebrows in the mirror. Plucking away one stray at a time until they looked shapely and clean enough. Then I grabbed a razor, and cleaned up the outsides of my eyebrows and the space between them.

Once I was content with my eyebrows, I started working on my body hair. I wish I had some nair, I could burn all of this off quick and easy, but I forgot to pick some up and I was in too deep now. I got in the tub and used the manscaper to trim down all of my hair from my facial hair to my ankles and everything in between. When that was done, I wiped up all the hair so I wouldn’t clog the drain, then I grabbed my shaving cream and my razor. I started at my toes and worked my way up. Then when I was done, I did it all over again. This was my first time shaving my whole body, so I would rather be safe than sorry!

When I was done, I took a quick shower. As I lathered up with the body wash, I couldn’t help but realize how smooth and soft my skin was without all the hair. It was a strange sensation. It felt like I was touching a stranger’s body. After getting out of the shower, I quickly applied a thick layer of lotion to my whole body. Then I wrapped myself up in my towel and retrieved my makeup bag from under the sink.

Once my face was dry, I put a light layer of orange color corrector where my shadow usually appears, then I covered my face with a generous layer of foundation. Next I grabbed my highlighter and my bronzer to cover the deeps bags under my eyes and contour my face. I added some blush along my cheek bones for a pop of color.

I always struggled with eyelash extensions and rarely wore them, but I decided I wanted to that day. I carefully applied the glue, grabbed my tweezers and carefully tried to line them up to get them perfectly in place. I tried and failed several times before I decided that they were good enough for me. Then I applied some mascara and used my eyelash curler to help my natural eyelashes and extensions blend together. I finished off my eyes with a light coating of white eyeshadow to help my eyes pop and I finished off my makeup with my favorite pink lip gloss.

I checked my phone and the time had flown that morning. Between the grooming, shower, and makeup, I had spent way more time in the bathroom than I had planned on that morning, so I quickly moved to the bedroom to start getting dressed. I grabbed my gaff and quickly tucked. Then I grabbed my sticky bra. I placed them right on the outside of my pecks so that the inside corner covered my nipple then pulled them together and secured them. I stacked two my nubras on top of it and covered it all with a padded pushup bra. Then I went back to the bathroom to quickly contour my bre@sts with some bronzer, before going back to my closet to pick out my wig.

On the top shelf of my closet, I had five wig stands each displaying their own unique wig. From left to right, I had a long straight black wig with a middle part, a medium wavy brunette wig with a side part, a medium wavy auburn wig with a middle part, a long wavy dirty blonde wig with dark roots and a middle part, and a shoulder length platinum blonde wig with a side part.

Each wig belonged to a different era of my life and had their own set of stories. The brunette wig was my first one and belonged to the period when I never left the house. The auburn wig was my longest running wig. This is the wig where I truly started to discover who I was and who I’m going to be. I left the house for the first time in this wig, had social media and dating accounts in this wig, etc. The black wig was an instant mistake. I probably wore that wig for a total of two hours. The dirty blonde wig was my adventurous wig. It wasn’t worn a lot, but I made frequent trips to Walmart in it. The platinum blonde wig was the newest. This belonged to my “hot girl summer” era.

By the time I had this wig, I had my makeup and shapewear routines fully figured out. No longer was I afraid to wear more “revealing” clothing because I didn’t have to worry about my breastforms looking fake because I wasn’t wearing breastforms at all! I had figured out a way to have realistic looking breaks where the only part people see was truly my own flesh thanks to nubras, padded pushup bras, and makeup. I also was a lot better at tucking at this point too! So, my outfits progressively became tighter, shorter, and more revealing.

I was several months deep into my “hot girl summer,” so there was no debate over which wig I was going to wear. I slid a wig cap over my natural hair and carefully tucked my brunette curls up into it before sliding the wig over my head and securing it with some wig tape. Once it was secure, I quickly brushed it for a few minutes.

At this point, my skin was hairless and glowing, my hair was on point, my makeup look amazing, my bre@st looked perky, natural, and real, and as far as the world was concerned my male bulge was non-existent.

My mind quickly wondered, “how did I end up here? How did I go from a boy who played with Barbies to becoming a Barbie myself?” I mean of course there was more to it than that like playing dress up with my sister and her friends as a kid, starting to “borrow” clothes from my mother and sister’s closets when I was home alone in middle school, accepting a dare to go as a sexy nurse for Halloween in undergrad, etc. It was a long journey of questioning who I am and who I want to be and at this point in life I still didn’t know the answer to either of those questions, but that didn’t matter because in this moment I knew I was a woman. I was undeniably a woman. I was 100% woman in everything but DNA, but nobody who saw me would know that because I just looked like a woman and I was happy.

I was so happy that I started to tear up a little, but I stopped myself because I couldn’t ruin my makeup. I just took a few minutes to admire myself in the mirror and I couldn’t stop smiling. “Maybe I’m not a crossdresser,” I thought, “maybe I truly am a woman trapped in a man’s body. Maybe I’m a transwoman.”

I threw on a dress from my closet and sent a few snapchats to some of my friends. I wasn’t out to any of my friends at this point so all of them took it as a huge surprise. All the replies were along the lines of “you look so good/cute,” “it all looks so real/natural,” and “I barely recognized you.” This filled my already happy heart with even more joy!

I suddenly became overcome with this feeling that I had to go! I didn’t know where, but I wanted to get out of the house and be out in the world. The dress didn’t seem like a practical thing to wear, so I changed into a tangerine cropped t-shirt, lavender short shorts, and white converse. Then I grabbed my sunglasses and cross body bag, and headed to campus.

I sat on the Quad and people watched for a little bit. A few people greeted me as they walked by. Then I went over to the student center to grab something for lunch. While I waited in line, a group of guys started talking to me. They told me that I should get out of line and come with them to the bar down the street. They’re grabbing food and drinks then heading to a darty afterwards. I was extremely nervous and flattered. Like did they know I wasn’t a cisgender woman and if not, how would they react when they found out? I declined their offer, but they kept insisting. Eventually, I told them that I’m going to sit out on lunch, but I’ll meet them at the darty later. They asked for my number so they could text me the details, but I had them give me theirs instead. It just felt like a better move for me since it gave me more control over the situation. Plus, if they tried calling me, my voicemail would have outed me.

I took my lunch back out to the quad and ate it there. I had a few more people try to take to me but I put airpods in and was scrolling on my phone while I ate. I decided I didn’t want to go to the darty and I didn’t want to put myself into a position to run into those guys again either, so I had to leave campus. I looked on my phone for other things to do today.

There was a movie playing that I wanted to see and I’ve never had the chance to sneak snacks in with a purse, so I decided that’s what was next for me. I texted my friends that I came out to early and all of them were busy. I didn’t want to go alone, so I took to my Tinder roster. I had been on Tinder for a few months and had a few different guys and girls I talked to regularly. I wasn’t interested in hooking up or dating anyone, it just felt nice to talk to people who thought I was hot. I didn’t think I would ever meet up with anyone, but I really wanted to go to the movie and I didn’t want to go alone, so I was a little desperate.

Not a lot of them replied fast enough. Those who did were either too far away, busy, or they kind of creeped me out. The ones who creeped me out talked about wanting to makeout, cuddle, or more during the movie and I wasn’t interested in any of those. Nobody was interested in just going to see a movie as just friends, so I went to the movie by myself.

It was a horror movie and I ended up having the whole theater to myself which was cool. It kind of made the whole experience creepier. It also gave me a chance to be on my phone during it and not be rude. Not that I was on it a lot because the only messages I was getting were from disappointed Tinder dudes. The movie also featured a trans actress which was cool. After the movie, I had to pee, so I stopped at the women’s restroom on my way out then headed home.

At home, I got changed a few times and took some pictures. For dinner, I got Taco Bell drive thru and the people working called me ma’am. Overall, it was just a really good day. That night, I played Fortnite with my friends and it was just business as usual. They were just treating me like one of the bros because why wouldn’t they be, but little did they know I was in full femme mode wearing a sundress and having random dudes slide into my DMs on my secret Insta.

(I feel like it’s important to note, I’m not into guys at all. Never have and more likely than not never will be. I do however talk to a lot of guys because it feels amazing to be complimented and treated like a woman. Is that wrong of me? Yes. Am I using them? Yes. Do I tell them all of this? Honestly, yes! They are all just convinced that they will be the one to change me, lol.)

That night, I didn’t feel like changing back, so I put on an oversized t-shirt and climbed into bed with my wig, makeup, and shapewear still on. As I laid there, my mind was all over the place. This was an amazing day, possibly the best day of my life. I looked amazing, felt amazing, had awesome adventures, came out to some friends, etc. I was so incredibly happy! It was everything I wanted the day to be and so much more!

Despite all of this, I knew that I could never go back, that today would be my last day as a crossdresser. I finally knew in my heart of hearts, that I wasn’t a crossdresser. I wasn’t just a guy wearing women’s clothes or even dressing up as a girl. I wasn’t just a guy, I was a girl. I was a woman. I was a woman in everything but DNA. Am I a transwoman? Maybe, but maybe not? Because I am a woman, but I’m also a man too. And I didn’t hate being a man, but I really loved being a woman…

My mind wandered like that for hours until I eventually fell asleep. I never figured out who I was that night, but I did figure out that I was more than just a crossdresser. This day sparked a new chapter in my gender journey. I wouldn’t truly understand or figure out who I was for at least another year, but I was happy and that’s all that matters!

Submitted by Lulu Digioia

Facebook Comments


  1. It is a wonderful story and the most important thing is how you feel about yourself, I also have that feeling without knowing why but when I wear something feminine it makes me happy and it does not create behaviors or interest in relationships with boys. Thank you very much for your story.

  2. There are so many of us that are a woman, trapped in a man’s body, and screaming to get out, to be free, to be liberated. Just like spending time in a cell with no door and no way of escaping.The only release we get, is to dress in feminine attire, with the hope we shall find some solace in it for a while. Those who are accepted as a woman, are fortunate. Then there are those who are encouraged to dress in women’s clothes. Then there are those who find it exciting to be enforced to dress in ladies wear, and have to execute household chores, that were done by women in the past decades.

  3. I.liked💄👗👠

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