Crossdressing Stories

Going to Wedding as a Girl with my Best Friend

Crossdressing Story - Going to Wedding as a Girl

My name is Jake. Since a young age, I was interested in crossdressing. When I was young, we had a play in school and the teacher dressed few of us boys as girls. I remember she told me to put on a pink frock and white stockings. Since then, I was really hooked on dressing like a girl. I loved everything about it. But I  kept my crossdressing a secret until one day ,my best friend found out about it. Amy was her name. She was so cool and we use to hang out a lot. She was kind of a tom-boy and didn’t really fit with the other girls. I was quite shy but I felt really comfortable around Amy.  We  did so many things together and I could always count on her.

I was crossdressing almost everyday when I was around 18 years old. I used to buy things like dresses and makeup online. I lived with my mother and most of the time she was out of the house due to her long work shift. That gave me more time to dress up around the house.

As time passed by, my desire to go out in public grew. I was bored dressing just inside the house. But at the same time, I was sacred to go out and afraid someone might find my secret. So slowly, I started to make myself become more passable as a girl. I practiced a lot in-front of the mirror to improve my feminine gestures and walk. I used to learn dance steps to famous girl group songs. After some time, I did get better at my transformation and my confidence grew.  But I only did all these things when I was alone. My mom had no idea because I was very good at keeping things hidden from here. I wanted to share my crossdressing with someone but I really feared they would not accept me after that.

During one college week, we had tons of assignment. Amy was my group partner in most of the subjects. I used to invite Amy to my house a lot but mostly we hanged out in the living room because I had many things hidden in my closet and I took every precaution I could to hide my crossdressing secret. One afternoon, we were doing a group report together in my house. We finished the report and Amy left the house. My mom wasn’t going to comeback for a few more hours, So i decided to dress up.

I went to my room to get ready.  I undressed myself completely and put on the bra and knickers first. Then, I slipped into a  yellow summer dress and sheer pantyhose. And to finish the look, I put on a brown straight hair wig that I brought recently. I didn’t feel like putting on the makeup because it took time and effort to remove them as well. So, I just put on some pink lip gloss. I had 3 pair of shoes, all of them high heels. This time, I decided to wear the white heels. I checked myself in the mirror and I was happy with how I looked.

Then, I opened the door and stepped into the living room. To my horror, Amy was standing right there. She saw me and screamed with surprise. I turned back immediately & stood there not knowing what to do. I was so shocked to see her.

Amy then finally spoke and asked ” Who are you? What are you doing here?”
I froze completely feeling so embarrassed. I figured it was no point to hide it anymore. She has seen me now. So I tried to think what to say but I was feeling so shy to turned around and face Amy.

Amy spoke again”” Who are you? Where is Jake? Are you his girlfriend?”
I was surprised. She really thought I was a girl. She was going to get really shocked few moments later.

With all the courage I had, I turned around . She looked at me. I was nervous to look into her eyes so kept staring down.

Amy getting a little closer now ” Why aren’t you talking? What are you doing here?”. She sounded pretty nervous as well.

I finally looked up and spoke. I could see from her face, Amy was totally shocked to realize it was actually me dressed as a girl.

I told her everything and she sat there listening. After a lot of talking, she was very supportive and praised my looks. Amy told me she actually came back to get back her notebook which she left in my house. We laughed at the coincidence. I had never felt so close to someone and I felt strange at first but relieved to share my secret with someone.

After that day, Amy and I used to hang out even more. Even though, she was not much interested to dress up or glam up, she loved getting me dressed up. I felt like she was enjoying feeling more manly in our friendship as I was the more feminine one. I went out in public for the first time with Amy and it was really amazing. I wore a cute white top and blue knee length skirt with black sandals. We went to the mall, did a lot of shopping and went out to eat in restaurant and then  went for walk in the park. I really wanted those moment to not end. It was so wonderful. Amy made my dreams come true and I thanked her always for that. She was modest about it but she really cared.

I started going out with Amy more frequently and sometimes, I would go alone too. I started getting quite confident about my feminine looks. I even managed to sound more feminine and I grew my hair quite long.

One evening, Amy called me up and asked me if I could go on a short trip with her. It was a wedding and she was one of the bride’s maid. It was her school friend’s wedding. Another friend who was supposed to be a bride’s maid was sick and could not attend.  Amy told me she also knew very less people there and it was a small wedding. She said she also had a spare dress of the bride’s maid and suggested me to go with her as a girl for the whole trip and also be one of the bride’s maid in her friends wedding.

Hearing that, I was super thrilled. I immediately said I would manage it anyhow. It was like a dream come true for me. So, I planned everything out with my mom and told her I was going with Amy for a short trip.

The day arrived, Amy came to pick me up in her car. I had butterflies in my stomach. I was super excited. As we drove out of the neighborhood, I slipped into a white floral dress inside the car. Amy was giggling the whole time. I was already wearing bra and knickers inside my male clothes before leaving the house. I let my  hair down and slipped into a pair of brown wedge shoes. Then I applied some eyeliner and lip gloss.

It was a 3 hours drive to the wedding so we had to get few snacks and drinks from the department store. We picked the stuffs and started driving again. It was an amazing sensation to be so far away from home and dress like a girl. I loved every moment of it and felt like a real girl. I couldn’t thank Amy enough.

As, we reached Amy’s friend house, I was getting nervous again. Amy looked at me as we parked the car and told me it would be fine and we would have a great time. I nodded and we gave each other a high-five. We got out of the car, took our things and went inside the house. There were few people working here and there and as we made an entrance, all of them turned their eyes on us. I felt quite shy. Amy’s friend Genny welcomed us inside the house. She was the one getting married the next day.   Everyone greeted us and then Amy introduced me as one of her close friend Julia.

Genny took us to the room where we would be spending the next few nights.

“You gals must be tired from the drive, get some rest and we will catch up in few hours.” Genny said with a smile.

We nodded and got to unpack our things. As soon as Amy and I was alone, I went up to Amy and gave her a big hug. She smiled and pushed me away teasingly.

We started un-packing. I had left all my manly things in the car and only brought the feminine stuffs in the bag. I had brought few dresses,  4 different pantyhose, a box of  makeup and three pair of shoes.

“You really are a girl!!” Amy said as she saw the things that I had packed. I blushed.

” Look, this will make you really happy. This is bridemaid’s dress you will wear for tomorrow. What do you think?”,  She added as she showed me this beautiful light yellow dress in her hands.

“Oh my dear, it’s so beautiful. I can’t believe I am going to be a bride’s maid tomorrow.” I screamed with joy.

” You are not only going to be a bride’s maid tomorrow, You are going to be the most beautiful bride’s maid ever. Also, I am so happy that we are going to be wearing the same dress tomorrow.”. Amy said with a smile.

I blushed again. I was having the time of my life. She handed me the dress and I couldn’t wait to try it on. I took off my dress and put on the dress. The fabric felt amazing and the dress was a perfect fit. I felt so beautiful looking at the mirror. Amy also complimented me about how great I looked in the dress. She also wore her dress and we posed infront of the mirror fooling around and having a lot of fun.

That night, Amy introduced me to her other friends she knew and everybody was so nice to me. I didn’t spoke much and tried to stay as elegant as I could. No one suspected me to be a boy and it felt like even if they knew, they won’t really care much. They were very friendly and accepting people.

I felt really grateful to experience these beautiful moments and I kept thanking god silently the whole night.

Amy and I had a great time that night and we made a lot of other new friends. We partied till late night and I tried my best to not get drunk. Amy was getting wasted and I was trying to take care of her the whole night. But it was a great party with friends that night.

We finally went to bed around 2 am and when we woke up it was late morning. I woke up first and then woke up Amy. We freshened up for the long day ahead and went to get breakfast. Most of the friends were already there and they greeted us with a smile. We then had good breakfast and went back to get ready for the ceremony.

I got a shower first, shaved any body and facial hair i had left and then moisturized my whole body.  Then blow dried my hair . Then, I put on a fresh pair of white bra and knicker that I had brought online. Then, I put on a bath robe and get my makeup and hair ready first before putting on the dress. Amy helped me with curling my hair and setting them up properly. I could do the makeup myself so I dolled myself up trying my best not to over do my makeup. After I was finished, I felt beautiful looking in the mirror. And with the wavy curled hair, I looked so feminine and gorgeous. Then, I put on a naked sheer pantyhose and then my beautiful bride’s maid dress.  I felt great and full of emotion. lastly, I slipped on a pair of white 2 and half inch pumps. It was going to be a long day so I had to go easy on the heel size.

I stood in-front of the mirror and twirled and danced around. Amy was laughing the whole time.

Amy got ready too and she looked great. She didn’t like to wear makeup that much and didn’t have much interest on dressing up. But for this wedding, she for a bit more dolled up than usually. Maybe it was my influence on her, I kept thinking.

We took tons of photos and videos and then stepped outside. People had started to arriving and there were a lot of new faces.

Since dressing up in public, I had realized that people would stare or look at girls much more than boys. It is just how things work. So, I was somewhat used to see people checking me out.  In fact, I enjoyed it. I loved how people would react to me as a girl. But this wedding was turning out be a little tricky. I had never got so much stare and people checking me out. I was feeling a strong presence of  attention from other people and it made me nervous. But I tried to keep my cool and Amy was also there to support me. I slowly got the hang of it and Amy also admitted that I was getting a lot of stares because I looked really beautiful.

“I think you will be making a lot of fans tonight Julie. I can already notice that the groom’s friends are checking you out like vulture” Amy said with a wink.

“I am getting a little nervous with all the staring Amy. Please don’t leave my side.”. I said looking around.

“Don’t worry dear. You will be fine. Just look at you. You look so cute in that dress and you are definitely the prettiest girl here in the wedding. Just be yourself allright.” Amy said looking at me.

I nodded. The wedding ceremony started and I tried to do what Amy had said. I started to feel a lot better as the wedding carried out. I felt like a beautiful girl spreading her wings of freedom.

The ceremony was finished after the next 3 hours and it was time for the celebration party. I meet more new people and most of them complimented me on how lovely I looked.  I felt really great with those compliments especially when guys complimented me.

The party and ceremony was taking place in the front of the house. As the party went on, Amy left me to talk with some of her friends. I felt I needed to pee so I decided to go inside the house from the back. There was a garden and there were less people there. So, I went inside, peed and came out of the house. As i was walking in the garden back to the party, a good looking guy approached me suddenly. He appeared be one of the groom’s friend. He talked about the party and few things about his friend who got married. I could see he was trying to impress me with jokes and hitting on me. It did feel nice to get hit on. I blushed. He kept talking and he was very smooth.

I started talking back a little and he was quite patient to let me talk.  I felt comfortable talking with him and we started talking about more personal things. He came a little closer and I could feel my whole body tingling. I wasn’t attracted to guys at all but this time, I could see myself getting pulled by his charm. I felt aroused and I could sense he was too. I had no intention of sharing to him that I was actually a guy and wanted to see where the moment would take us both. I was loving getting swayed in romance with him.

He then finally grabbed my hand and we stood there holding hands for sometime. My whole body was tingling and my heart was starting to beat a bit faster. He came even more close and suddenly, he grabbed me from behind and hugged me tightly. I was completely under his spell. I tried to make him let go of me but he was holding me firmly and I didn’t resist enough because somehow I wanted it too. I wanted to know how it felt and everything. He then kissed on my  cheeks and on my neck. I was just standing there giving him all the control. Then he turned me around and looked me in my eyes and told me I looked so beautiful. I blushed and kept looking down. Then slowly his face came closer to my face and he started to kiss me on my lips. His hands were touching my hips and I couldn’t hold back so I started hugging him back.

Suddenly someone screamed my name and I finally got a better hold of myself and the situation. It was Amy calling from the front, she had seen me with the guys kissing. I felt embarrassed. Amy came up to us and looked me in the eyes with anger.

“What are you doing?” Amy spoke. ” I have been looking all over for you.”

I didn’t know what to say. Then Amy took my hand and asked the guy to excuse us. We then walked up to the front where the party was going. Amy scolded me for behaving so cheaply and told me the guy could have taken advantage of me easily. I was embarrassed with my behavior and I apologized to Amy. She was angry for sometime but she cooled off and I took lot of caution to stay away from guys that night. But in the back of my mind, I couldn’t stop thinking about how I made out with a guy. This has been an amazing roller coaster ride that I will never forget in my life.

The party was great. We had lots of fun and made so many new friends. We slept there that night and left the next afternoon. It was an adventure of lifetime and there were many more adventures to come in my life. I was sure of it.


PART 2 coming soon.

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  1. Oh! If only I could be a bridesmaid, at a wedding! And be hit upon by one of the groom,s friends. That would make my feminine day perfect! Who knows, maybe one day I too will become a bride! How wonderful that would be!
    Feminine Forever,
    Miss Roxanne Lanyon
    (A Feminine Guy in Skirts)

  2. I am 69 and crossdressed since I was 8, I’ve always had female friends but the regret I’ve never been invited to be a bridesmaid, it is a deep longing of mine.

  3. As a boy growing up with a twin sister,i was always in awe of sis being a ‘girly’ girl and see her wearing her girly dresses and clothes and on laundry day,seeing her cute,freshly washed panties in the laundry basket.As we got older, and became teenagers,i was really wanting to understand what it was like being a ‘girl’! Then when we were 15,we finially made our First Holy Communions in the class of 2nd graders.I wore my dark colored suit and ty and in order to fit in with the little girls,was dressed in a poofy,short sleeve,knee length communion dress and veil with lace anklets and white maryjane shoes and under her dress mom did a cloth diaper and plastic pants and tee shirt on her just like the little girls all wore.I was stunned by how cute and dainty and little girlish sis looked in her outfit and mom lifted up sis’s dress and showed me the diaper and plastic pants and sis looked like a baby with them on! Later that week,i came home from school and mom was out shopping and sis was at a friends house.Her entire FHC outfit was still in her room so i went in,took off my clothes and put her entire outfit on and pretended i was a girl and loved it! After that i got into crossdressing more and more with her clothes!

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