My name is Garry and I am going to share one of my scariest moment as a crossdresser about how my girlfriend caught me wearing her clothes.
Since I was a kid, I was quite attracted to feminine clothing like skirts and dresses that girls used to wear. I really wanted to dress like a girl and wear cute outfits. I didn’t have any sisters so the only feminine outfits I could try was my mother’s clothes. It was only after I joined college and moved out from my parent’s house that I got the opportunity to dress up more freely.
I started to crossdress quite a lot during my college years and used to buy a lot of outfits and feminine stuffs online. It was just so wonderful to dress up and express my feminine side. But time and again, I felt like it was sometime I shouldn’t be doing and would purge all my feminine stuffs.
I tried many times to stop myself from crossdressing but sooner or later, I always felt the need to dress up and just express my feminine side. Then I would buy stuffs again to dress up and again after some months, I would throw away all my girly things to try to stop my crossdressing habit. It was going on like that for sometimes.
As time passed, I got into a relationship with this lovely girl I met at a friend’s party. We got really close and started to hang out together all the time. Then I asked her to move in with me and she did. I decided to stop crossdressing for good and after that I didn’t dress up at all.
Everything was going great, I had a good job and a lovely girlfriend. I didn’t have too much time to think about crossdressing and I felt no urge to dress up. But after 6 months or so into our relationship, one day as I was going through the folders in my laptop, I found old pictures of me crossdressing and it immediately brought back so many memories. I did miss dressing up and feeling cute, and expressing my girly side. Slowly, after that moment, I started having the urge to dress up again.
So, one day while my girlfriend was out. I opened her closet and I could feel the thrill flowing in my body again. I looked around and then took out one of her panties and padded bra. I didn’t know if the bra and panties would fit me and when I tried them on, they did. I could sense my heart beat getting faster as I looked myself in the mirror.
Then I started browsing through my girlfriend’s lingerie collection and found a bunch of pantyhose. I took one out, put them on and it felt wonderful. Next, I took out one of her formal wear. It was a white blouse and black skirt. I put them on and I could feel the rush inside my body. It was an incredible sensation. The clothes were a little tight for my body but I could fit in them.
After posing and walking around for sometime, I started to feel like I was missing something. I realized I didn’t look girly enough without a nice hair wig and high heels. Then I decided to try on one of my girlfriend’s heel but unfortunately they were too small for me. After few minutes, I took everything off , put them back and walked out of the room trying not to think about it again.
But I couldn’t stop visualizing about all the cute lingerie and clothes that my girlfriend had after that moment. I wanted to try on everything. And it started again, I would sneak into my girlfriend’s closet and wear her outfits whenever I had a chance. It went on for a month and then I decided to get myself a nice hair wig and a pair of heels. I didn’t wanted to buy more things because I knew it would be a problem to hide them from my girlfriend.
It was exciting to order the wig and heels online. I couldn’t wait for them to arrive. And after few days, they did. I hid them in the storage room in my old CPU case. As time passed, I was dressing up more and more in my girlfriend’s clothes.
One day, while my girlfriend was out with her friends on a weekend. I decided to give myself a full makeover and do a photoshoot afterwards. I had already planned everything and after my girlfriend was out, I got dressed in her black dress and sheer pantyhose.
Then I decide to do a full glam makeup look and it felt amazing getting ready for a full transformation. I put on some foundation, then some eyeliner , mascara, and finally a red lipstick. After I was done with makeup, I put on my hair wig and the high heels. I loved how feminine I looked. I was so excited to walk around the house and take lots of videos and photos.
My girlfriend was only supposed to be back in the evening so I thought I had plenty of time to keep staying dressed. I walked around the house in heels, took a lot of photos and I was having a great time. After some hours, I felt like taking videos in my bedroom. So, I went to the bedroom, setup the camera in the tripod, put on some music and started taking videos. While I was doing so, I was unaware that my girlfriend had came home early and with the music on, I didn’t hear her parking the car in the garage.
It was the moment every secret cross-dresser dreads; I was posing in-front of the camera when the door swung open and I saw her. I was completely terrified and she was quite shocked seeing me like that too. I just froze looking at my girlfriend. I was so embarrassed that she saw me like that and to make matter worse, I was wearing her clothes and makeup too. I didn’t knew what to do next, I was so busted.
“What are you doing? I can’t believe this. Are you doing a prank on me or something?”, she asked me.
I didn’t know how to reply back. I covered my face and just stood there. My girlfriend was pretty confused about the situation and I didn’t blame her. Then she came close to me and we both sat down on the bed. I never felt so humiliated in my life before and I apologized to her.
I had no other option but to tell her everything and I was surprised how calm and supportive she was. She patiently listened to me and told me it was all-right. She did mentioned that it would have been better if I had told her about my crossdressing before. Then I went to change clothes and she stopped me and said ” You do make a beautiful girl”. I blushed and she kissed me.
After that incident, we had a long conversation and I had to convince her that I wasn’t interested in men but I did like to dress feminine once in a while. She was very understanding. I was sure she would leave me but she didn’t and now she is okay with me dressing up sometimes but only inside the house. Now, when I think of it, it was better that I was caught because after that I felt really relieved and accept myself for who I am.
Sent by Garry