Crossdressing Stories


“Since childhood, I was always fascinated by women’s clothing. I used to secretly put on my sister’s dress and liked feeling pretty and girly. I tried to stop those urges but it only grew bigger. As time went by, I started to sneak into my sister’s room more often. I tried on her outfits, her makeup and shoes. It was such a rush. So, every time I was going to be alone in the house, I would simply dress up.

I started to buy outfits, lingerie, hair wigs from online stores and kept everything hidden in my closet.

One day, my whole family was going away for a trip to one of our relatives. I somehow managed to stay back saying I had few assignments to finish. It was a great opportunity to have the whole house to myself. So, my family left and I was so thrilled to dress up. I really wanted to have a complete makeover from head to toe and spend as much time as a girl.

Wasting no time, I started to get ready. I started with makeup, then put on undergarments and a pink bodycon dress that I had recently brought. I completed my transformation with a blonde hair wig, pantyhose and heels. It was amazing to see my reflection in the mirror as a girl. I thought I looked cute.

After I was ready, I walked around the house in my new attire. It really felt great. I took so many photos and videos that I lost track of time. My family was only coming back the next day, so I still had some time left to spend as a girl.

In the evening, I cooked dinner all dressed up for the first time. It was great. Then after I was done with eating, i was simply too tired. I decided to go to my backyard for a cigarette, take few videos and call it a day.

I did go outside in the backyard dressed up few times before but they were only for a short period.

I walked out to my backyard, I was feeling a bit nervous if my neighbors would see. So, I inspected around for a bit till I was comfortable. Then after confirming, I setup the camera, lit the cigarette and started filming.

It was only after I put out the cigarette that I noticed there was a women staring at me from the neighbor’s house. I had no idea how long she was there. I immediately panicked. My heart beat got faster and faster. But still, I tried to not overreact. Simply and slowly, I walked back inside the house.

I felt quite scared that my crossdressing secret was now exposed and my parents would also find out about it.

I was planning to spend the whole night dressed up but this incident made me change my mind. So, I undressed and went to bed. I was having so many thoughts that night. It would be so embarrassing if other people found about my crossdressing habit.

Next day, my family came back. I was nervous that the neighbors might talk with my mom about seeing me crossdress.

It was after a week that my mom calls me down in the kitchen and says she wants to talk with me. I get really nervous. She then asks about the day that I was alone in the house. “Who was that girl?” asked my mom ” I told you not to bring girls over to the house.”.

I was a little puzzled and replied “What girl?”.

She then tells me that our neighbor mentioned to her that they saw a girl in our backyard and thought she was pretty. When I heard that, I was just so surprised. My neighbors didn’t recognize me and thought I was actually a girl. I felt relieved and happy at the same time.

Making something up, I then told my mom that one of my college friend did drop by for some notes but she didn’t stay that long. My mom believed my story and I got away with it. It’s been quite a long time after that but I will never forget that crossdressing moment.”

The End

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  1. I used to take mom’s panties when I was younger now that I am older I buy my own panties I would like to get caught wearing panties

  2. Boys are often curious about moms things. I remember how exciting it felt the first time I touched my moms panties and bra. It was so intoxicating to feel them that I couldn’t help but imagine what it must be like to wear them.

  3. But it must have made you feel good, to say that your neighbour thought she’d seen a girl, It would have given me whole load of confidence if it had been me,

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