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My First Boyfriend

my first boyfriend crossdressing story

Since childhood, I was always fascinated by women’s clothing. I used to secretly put on my step mother’s dress s 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 step mother’s room more often. I tried on her outfits, her makeup and shoes. 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 on a trip to one of our relatives. I somehow managed to stay behind, saying I have a few tasks to finish. It was a great opportunity to take the whole house to myself. So my parents left and I was so excited to get dressed. I really wanted to wear a full make-up from head to toe and spend as much time as a girl.



I started getting ready without wasting time. I started with makeup, then undergarments and a pink bodycon dress that I recently brought in. I finished my transformation with a blonde wig, pantyhose and high heels. It was surprising 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 outfit. It felt really great. I took so many photos and videos that I did not understand how time passed. My parents were only coming back the next day, so I still had time to spend as a girl.

I had been out to the backyard several times dressed before, but it was only for a short time.

I walked into my backyard, feeling a little nervous if my neighbors saw it. So I looked around until I was comfortable. After confirming, I set up the camera and started shooting.



I noticed there was a boy looking after me from the neighbor’s house. I didn’t know how long he stayed there. I immediately panicked. My heartbeat got faster and faster. But I still tried not to overreact. I simply and slowly entered the house.

I was terrified that my cross-dressing secret would be exposed and my family would find out.

Soon the boy rang the bell and entered the house and kissed me. I was now a boy’s girlfriend.

The End

Submitted by Denise

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