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My Scariest Moment as a Crossdresser

Crossdresser Story I am an 18 years old secret crossdresser. Since I was young, I was fascinated by clothes of the opposite gender and started to crossdress in my sister’s clothes secretly. Over time I would buy many girly stuff online and would dress up in my room usually at night time.

One day, I brought a pink baby doll set online and when it arrived I was overjoyed. I couldn’t wait to dress up in it. The timing couldn’t be more perfect as my family was going out for the afternoon. I decided to make it extra special by getting all dolled up and doing something more adventurous inside the house.

First, I made sure the front and back door of the house was locked and then went to my room. I closed all the curtains and decided to do my makeup first. I had already shaved in the morning so I just washed my face and put on some moisturizer so its easier to take of my makeup later.

Then I applied foundation on my face, much more than needed probably because I was so excited at that moment. I was able to remove the excess by dabbing it with some tissues. Once that was done, I put on some eyeliner. I usually struggle to put on the eyeliner neatly on both my eyes so they match. After a lot of tries, I finally managed to do a decent job with the eyeliner.

Next, I put on some pink lip gloss and my makeup was done. I did some final retouching to my makeup and got undressed. My body was shaking with excitement. First, I put on the pink thong and I loved how it felt and looked on my body. Then I put on the pink baby doll and I instantly felt so feminine and beautiful. Buying the baby doll set was definitely worth it.

Now, for the final part of the transformation. I put on my favorite blonde wig and adjusted it nicely on my head. I looked in the mirror and I was so happy with my reflection. I looked so cute. I was totally in love with my new look.

I decided to wear my golden pumps to complete the look. Then I posed in-front of the mirror and couldn’t stop admiring myself. I took a lot of photos and videos and it was so much fun. Then I decided to step out of the room and sneak into my sister’s room to grab some of her perfume. It was really exciting for me because I have never stepped out of my room fully dressed.

As I took my first few steps outside of my room, I felt scared and excited at the same time. I felt vulnerable and my heart beat was increasing more and more with the steps I took. I finally managed to get in front of my sister room and opened the door. The curtains were all open. That made me scared to go inside because someone from outside might see me. After peeking here and there, I decided to step in and put on some perfume. I splashed myself with one of her perfume and it was really nice.

Then I decided to take a couple of photos and videos in my sister’s room. It was really exciting to be in her room all dressed up. Then I wondered if I should go to the living room and take some photos there too. I slowly walked to the living room and my heart was beating faster again. The thrill of getting caught was quite intense.

Even though I must have spent so much time in the living room, this time it felt as if it was my first time being there. I was just too scared to relax and take pictures so I rushed and took a couple of pics and hurried back to my room. Once I was in the safety of my room, I felt more relieved.

I decided to make a couple of videos and placed my phone on a tripod. Took a few videos but felt like it was a bit dark. So. I decided to open up the curtains. First I peeked outside to see if any of the neighbors were out. I didn’t see anyone, so I slowly opened the curtains. The light was so much better now to make some videos but at the same time, I was really nervous that someone would see me. I was very conscious of it.

I took some videos but occasionally my eyes would automatically go to the window to see if anyone was watching me. After a few takes, I started getting more comfortable and confident to pose. I decided to make some girly videos of myself and lost track of time. I just didn’t want to stop at that moment but I knew my parents would be home soon. So, I decided to make one more video and call it a day.

As I finished recording my last video and went to hit the stop button, I suddenly saw two girls at the window of the house across the street and they seemed to be filming me and giggling. I was completely terrified and so shaken. I panicked and immediately closed the curtains. How long were they watching me?  Why didn’t I notice them before? Why was I so stupid to open the curtains for such a long time? Were they actually recording me? All these questions were hammering in my heard.

I undressed myself and put on my normal clothes. Then went to the bathroom to take of my makeup quickly. While I was doing all this, I couldn’t shake up the embarrassment of being caught and worse if they actually recorded me in such a naughty outfit.

After I removed the makeup properly, I put everything back in my closet and decided to check if the girls were still there at the window. I slowly peeked and the girls were still there looking over occasionally. The girls looked like they were in their twenties. What if they posted the video on TikTok or Instagram? I felt so busted and humiliated. My mind was running blank on what I should do next. Should I go over and ask them not to post any videos on the internet?

Then, I heard my dad’s car pulling in to the drive way. My parents were back. I  checked my face again to see if there was any trace of makeup. Then I rushed to open the front door. From the side window, I peeked to see if the girls were still there and they were. I was so scared. I rushed back to my room and pretended to be on my phone.

My parents and my sister walked into the house and my mom called me to say they brought me some food. I told them I was watching a movie and will eat it later. Luckily, no one came into my room at that moment. After a few minutes had passed, I peeked out my window to check on the girls and finally, they were not there. I was still so scared to open up the curtains but if I didn’t my mom would surely suspect something if she came into my room. So, I opened the curtains, my heart was beating like crazy.

So many thoughts were racing in my head. I didn’t recognize the girls from the neighbor’s house. Maybe they were friends of Jane, the neighbor’s daughter or perhaps they could just be relatives. I was so spooked at that moment not able to wrap my head around what just happened and what I should do next.

Surely, I saw them with their phones out. Did they take some photos or were they recording a video? It would be a disaster if they posted them online and someone recognized me. I had no courage to go to the house and face the girls. I was just praying they didn’t post anything online or told the neighbors what they saw.

Its been a few weeks now since the incident and luckily there hasn’t been any news from the neighbors or any posting on the internet that I have been able to  find. Hopefully, this will just pass away with time. I would like to advice other secret crossdressers out there to be careful to protect their identity.

Sent by Alice

Facebook Comments


  1. What’s the worst that could happen?
    If you don’t know them it’s unlikely they’ll work out who you are.
    I think you need to consider the rule of N.
    N things have to happen for you to be “discovered” and something to happen.

    1. the girls needed to have actually been videoing
    2. the video needs to be good enough quality to see what was going on
    3. the girls need to decide to share it
    4. they actually need to share it
    5. someone has to actually see the shared vid.
    6. and think it’s unusual
    7. and want to share it further
    8. someone seeing the vid needs to recognise you
    9. and then be confident enough to confront you.

    i think it’s all pretty unlikely and if something happens…
    Well, you will probably be telling someone someday anyway.

    More likely the girls were fascinated and happy to see something exciting for a change.
    Perhaps you need to say hello to them when you see them and tell them it was you. You never now, they might all become girlfriends and they’ll dress you up and take you out!

    Don’t worry – it probably won’t happen.
    Enjoy yourself


  2. How exciting that must have been. I do protect myself but when I go away on business sometimes I wander the hotel hallway dressed as it doesn’t matter if people I don’t know catch me. Just don’t want to ruin my daily life.


  4. I have been cross dressing since I was ten.. I was caught by my Aunt who decided to black mail me.. She said that I have to do what she wants I had to say yes ma’am.she would dress me up in sexy lingerie and heels and have me take care of her needs that is when I was taught how to go down on her and give her multiple orgasms..I loved everything she said and made me do

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