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Dressing up in-front of Girlfriend for First Time

Dressing up in-front of Girlfriend for First Time
I’ve always been fascinated with girls clothes since I was quite young. I used to wear my mum’s dresses when I was alone at home. Later, I started wearing her bra and I really liked it. As I’ve gotten older, I have been in a few relationship with girls and whenever I was alone, I have dressed in their clothes secretly.

I really like wearing short dresses and pantyhose specially. When I moved out from my parent’s house, I started buying feminine stuffs for myself and this was the time that I really started to experiment with a lot of feminine things. The first time I got dressed up from head to toe was an amazing experience that I will never forget. I really had no idea that I would look so good as a girl. Since my body type is quite slim, most of the girl’s outfit suited me.

I thought of myself as a straight crossdresser and was never really attracted to guys. But slowly with time, I started fantasizing about being handled by guys whenever I dressed up. But I continued to date girls only. I kept my crossdressing a complete secret from everyone. It was only when I meet a special girl who forever changed my life.

I had just recently started dating this lovely & quite daring girl. She was quite adventurous and was always ready to try out new things. One time while we were making out, she joked about me trying out her lingerie. I was pretty skeptic but she really forced me and I tried it on for her. To be honest, it felt quite nice and liberating. We had a lot of fun together.

I would wear her outfits secretly whenever I had a chance. Dressing in her clothes seems to make me feel so girly. At one point, I finally decided to tell her about my crossdressing secret and she took it really well and said she was okay with it. She also confessed that she was attracted to guys as well as girls. She asked me to dress up for her and I did. I felt quite nervous since this was the first time any person would see me as a girl.

I got ready in about 20 minutes and when she saw me, she was really surprised. She was really supportive and even offered me to do my makeup properly. I agreed and then we had a great time together, talking and fooling around while she did my makeup.

It felt really wonderful having someone feminize me even further and it felt like I was in a trance. When she was finished with the makeup, I was really shocked to see myself in the mirror. I really look so feminine and beautiful. After that, we made out and I was really turned on by this whole new experience of being a girl front of someone.

After that, I started dressing up more frequently in-front of my girlfriend. She would teach me a lot about makeup and styling. I started getting better with makeup and my feminine manners. It was almost like two girls living together. I felt really lucky to have a girl like her in my life.

One day, she suggested that we should go shopping together while I was dressed as a girl. I was really excited and nervous at the same time. She told me it was no big deal and that it would be a really fun thing for me. We picked an afternoon time to go out to a mall.

I got ready in a white top and brown skirt with sneakers. I had my blonde lace hair wig on and applied some light makeup. It felt really exciting to go out as a girl for the first time. So off we went and the whole time I was in the car, it felt really nice to be dressed feminine and express my girly side so openly.

We arrived at the mall and I was very nervous but my girlfriend said it was going to be alright and nobody would notice if we minded our own business. We went inside the mall, there wasn’t  many people at that time and I started feeling a bit relaxed.

However, it felt like people were starting at me the whole time and I felt really shy & nervous time to time. We went to many stores and checked out so many things. I talked very little while we were in the store because I didn’t wanted people to find out. The staffs in the stores were quite friendly and except them no body  bothered us at all.

I brought one bodycon dress and a few makeup products. We also hanged out in the food court and it was amazing. We headed back home and I was really grateful to have such an amazing girlfriend. When we reached home, we were both so tired after a long day of shopping and crashed on the bed straight away.

Eventually, I started going out more frequently dressed as a girl but only with my girlfriend. We would go to the movies, restaurants or go for a walk in the park. My feminine wardrobe grew quite a lot and I would wear most of my girlfriend’s clothes too. On my birthday, she got me a surprise gift and when I opened it, it was a strap-on. I blushed and she knew I really wanted to try that. So, it was going to be a exciting night for both of us.

We went out for dinner, just me and her and I was dressed in a floral mini dress & high heels with a glam makeup on. We both got a bit drunk as well before we headed back home. When we finally reached home, I could barely walk in the 3 inch high heels that I was wearing.

Then, finally inside the bedroom, she told me to strip for her. I gave her a good strip tease and she was impressed. I only had my bra and thong on now and then she took out the strap on. I was so turned on by just the thought of it. Then, we kissed for a bit and finally she wore the strap-on and adjust it nicely. It was also her first time giving it to a guy and she seemed equally excited.

First, she told me to get down on my knees and  give her a nice blow-job . I did as she said and slowly started to lick the tip of the strap-on and then finally put it in my mouth. She then forced it deeper in my mouth and I suck-ed on it intensely. After a few minutes of that, she told me to lie down on the bed with my legs open wide.

Then she took off the thong that I was wearing and started caressing my butthole. I was getting so arous-ed and completely in her spell now. She then put on some lubrication in my hole and gradually pressed the strap-on inside me. It was quite painful and I really didn’t expect it. I told her to stop but she had already inserted it deep inside my hole.

Then she slowly started to move it in and out. I couldn’t help but scream and moan while she penetrated me. It hurt so much but I wanted more of it. It was a very intense sensation. Then she started to go faster and I went crazy as I moaned really loudly. Then she got me into the doggy position and started penetrating me even harder. I finally discharged and my girlfriend was happy that she could make me do it while she was being in charge. One of the best birthday of my life.

– Sent by Sophia Miller

Facebook Comments


  1. Wish I get a gf like her

  2. Iam cross💃

  3. mmm, wish i had you as a g/f

  4. My better half did that to me about three months into our relationship she knew about me dressing I told her by wearing a nighty and thong the first night and she was more than delighted with me and now after more than 20 years together still get excited about playing

  5. I love your story, I’ve wished for decades for a woman like your girlfriend.

    1. Me too 😘😘

  6. Wonderful story. My wife is supportive even after many years as a CD, but never an initiator. Lucky you and your partner

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