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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

Facebook Comments


  1. Lucky boy, no doubt.

  2. Yes, then what happened?

  3. Awesome story. I actually kind of liked that you ended the story with saying that you’d become his girlfriend and let the reader’s imagination fill in the rest of the story after you two disappear behind the closed door to experience intimacy in private. Loved it!

  4. I loved it when he kissed me. It opened up a new world for me. Not only was I dressed as a girl, but now I was loved by a sweet little boy. Oh, what I could do for him! Mmmmmmm . . . . . .
    Miss Roxanne Lanyon

    1. I hope you DID do it for him. And he do it to you… Uh, for you.

      1. Oh, I just know he will be ever so nice to me! I will adore being his girl! I just want to be in mis arms forever, and do whatever he asks! I LOVE BEING HIS WOMAN!
        Miss Roxanne Lanyon

    2. Title says he was your FIRST boyfriend. Can you tell us about your subsequent ones?

  5. Dears,
    that event fullfilled my dreams. I now had a man! I became the happiest girl in the world, and did everything for him! It is such a good feeling to actually belong to a loving man, a wonderful person so full of masculinity! It makes being feminine a real dream! I will be his woman forever, and always obey his wishes, no matter how slippery and creamy it becomes! I just want to love my man forever and ever! I will make him ever so happy and pleased he owns me!
    Miss Roxanne Lanyon

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