Crossdressing Stories

Boy Disguised as a Girl

Girl in disquise Crossdressing story

Mandy lived two houses away from us when I was growing up. We both were in the same grade and in the same class so we became good friends. Nothing was salacious about our relationship, just two kids growing up having kid fun. Catching frogs, playing catch, watching the clouds drift by, riding our bikes through the neighborhood.

You know kid stuffs. I never really paid attention in how we were dressed except I knew that girls wore dresses and skirts while boys wore tee-shirts and jeans. It must have been about 7th grade when I started to really take notice.

While walking home from school with Mandy one day I just had to ask her, “What is it like to wear a dress?”

She looked at me, “What do you mean?”

“I mean with your legs bare when outside.” I replied. Giggling.

“Silly, you have had on shorts before. I’ve seen you in them. It’s the same thing.”

I stopped for a second, “No Mandy, shorts start mid thigh and everything above is covered, not like a dress where your legs are still bare up to your underwear.”

Mandy just looked at me and didn’t say anything.

The rest of the walk consisted of small talk. We came up to her house first, “Do you want to come in?” She asked. “Sure” I replied and followed her into the house. Her parents were not home for they both had to work so we had the house to ourselves. We put our school bags down and Mandy took me by the hand and said, “Let’s go.” She led me to her room where I’ve been several times before.

Going to her dresser she turned to look at me, “We are about the same height.” and with that she took out a dress and handed it to me.

“Now go into the bathroom and put it on then come back out and let me see.” I didn’t know what to do. Should I do what she said? Was she teasing me? Is this for real? I was in a state of confusion and bewilderment.

Mandy grabbed me, turned me around and ushered me into her bathroom, “Don’t stand, go.” I went into the bathroom and closed the door and stood there with her dress in my hands. “You can’t come out until you put it on” I heard her yell from the other side. So I striped down to my underpants and put the dress on over my head.

Nervously I opened the door to the bedroom where Mandy was standing. I stepped outside and she giggled a bit. “Now turn around, let me see. “ So I turned around in a full circle for her. She had me sit on the bed saying it is “Wrong, wrong, wrong! Take your socks off”. She grabbed one of my legs and yanked the sock off one of my foot, tossed it to the floor and went to her dresser.

As I removed the other sock I looked up and saw her take out a pair of white stocking. She walked over to me and gave them to me, “Now, put them on”. Before I could do anything she stopped me, “Are you wearing boys underpants”? I just looked at her, “Errr ya, I am. After all I am a boy. What do you think I had on”? Mandy went back to her dresser “No, no, no, no! That will never do. No!” With that she took out a pair of pink panties and tossed them to me. “I’m going to turn my back on you.

Take off your underpants and put those on, now.” Mandy had her back to me and I slipped off my underpants and the pink panties on. They felt weird but very comfortable, more so than my own underpants. Mandy turned around and ushered me to put on the stockings.

I’ve seen TV commercials and TV shows with women putting on stockings so I had the idea in how to roll up each leg, insert my foot then pull them on. I had one foot in Mandy piped up, “Careful, don’t put a run into them.” Slowly and carefully I pulled up each leg. They felt so nice and the way they hugged my legs was wonderful.

Mandy watched me in amazement as I pulled up the pantyhose. Then she went to her closet and took out a pair of sandals with a 1″ heel and a strap at back for the heel. “I don’t think any of my other shoes will fit you, but we can adjust the heel strap so you can get into these.“ she said. Mandy then put the sandals on my feet adjusting the strap so my feet would go in them and stay. The heel of my foot did extend a little over the back, but the strap held my foot in place.

Mandy looked at my smiling and said ” One more item.“ She went to her dresser and took something off the top and hid it in her hand then walked over to me. “Now stand still, look straight and relax.” She opened her hand and I saw that she had lipstick there. She put one hand behind my neck and with the other applied the bright red lip stick on my lips.

All kinds of thoughts were racing through my head and I didn’t know where to begin. Mandy finished putting the lipstick on me and then did her own lips as she looked me over. “There, don’t you look pretty” she said. “How is it? Do you like it? “ Nervously I replied ” Well…I…“, I couldn’t answer but deep down inside I felt something so invigorating and wonderful.

I couldn’t put my finger on it, but for some reason it felt right. Mandy locked her arm through mine and took me to the mirror in her room where I saw myself in the dress with bright red lipstick on. “There, now we can be sisters. What should I call you? I can’t use Johnny your boy name. Girls don’t have boy names. I know, you will be ‘Joan’ and that is what I will call you.”

She is going to call me ‘Joan’ I thought to myself. But I’m a boy, not a girl. OK I’m in a dress but I’m still a boy. But wearing the dress did make me feel like a girl. Mandy took me by the hand and brought me into the dining room. My first step in her heels was a bit uneasy but I quickly got used to walking in them.

I really felt weird but nice at the same time. In her dining room was a sliding glass door that led to the back yard deck. I was often invited over for barbecues so I was familiar with her back yard. Mandy opened the doors and turned to me, “Come on Joan, let’s sit outside. Don’t worry, no one will see us.” She was right about that. They had a very high fence around the backyard and plenty of trees lining the parameter. It was so thick and the way the house was situated no one could see into her backyard.

Slowly yet cautiously I stepped out onto the deck. I knew that no one could see us, but there was that air of suspicion. I walked to the railing, overlooking the rest of the yard and turned to Mandy who was grinning ear to ear.

“Well, does this answer your question?” Mandy asked.

“What question.” I replied.

“What does wearing a dress feel like. You silly head.” Mandy said.

I paused for a second before I answered. “Well..“ Before I could finish she interjected, “Bet you like it, don’t you?” Looking at her I said, “I guess. It feels OK.” But deep inside I was thinking how strangely nice it really was. “Oh I know you like it, I just know it. Why don’t we sit down out here and enjoy ourselves.” She said.

So we sat at the table and spent some time engaged in girl talk of all things. Mandy would go on about the other girls in school, dresses, make up and things like that.

After a bit, Mandy got up, “Wait here, I’m going to get us something to drink”. And with that she left to go inside. I sat there admiring my legs seeing how they came out from the bottom of the dress, the shimmering of the stocking and my feet in the heels. It also felt so wonderful and relaxing.

A few minutes later Mandy came back out with two glasses of soda. Thanking her I took a sip. I looked at the glass and there was a bright red lipstick mark that I made. Mandy paid no attention to hers and we just kept on talking. Mandy glanced at her watch, “We have to go inside Joan.

My mom will be here in a little while.” We got up and headed to her room. When we got there I needed to use the bathroom. “Give me a second, I have to pee. “ I went into her bathroom, closed the door and stood in front of the toilet. I lifted the seat like at home, then lifted the front of the dress, pulled down the pantyhose and panties just enough.

Holding the front side of the dress up with one hand and my penis in the other, I had to be very careful not to get any on the dress. I shook off the last few drops, dabbed myself with some toilet paper to be sure there was nothing left, I pulled up the panties and pantyhose. I flushed, washed my hands and stepped out into Mandy’s bedroom where Mandy was waiting for me.

Mandy saw that the toilet seat was up and gave me a stern look. “Girls pee sitting down, not standing up Joan. So when you are dressed like a girl, you have to pee like a girl. OK” Did she say ‘when dressed like a girl, pee like a girl? Does that mean what I think it does? “OK, I’ll remember. “ I said. Mandy took me over to her dresser and gave me a quick tour of what she had in the drawers and then did the same with the closet.

Looking at me she said, “When you come over after school, you can wear anything that you want. Anything. ” A part of me woke up and started to jump for joy. Another part was confused. I simply looked back at her, “OK, that sounds like fun.”

“See, I knew you would enjoy dressing like a girl. We can be sisters when you do. Now quickly get changed I have a few things I need to do.” Mandy then left the bedroom closing the door behind her.

Alone now, I stood in the middle of her room looking at myself in the mirror. Something inside of me was telling me that this is right and meant for me to do. At the same time I was worried what if it was discovered that I liked wearing girls clothes. I didn’t have time to lament on these thoughts so I quickly got back into my regular clothes, washed the lipstick off, put the dress in the closet and under things into the hamper.

Making one last check to see that everything was as it should be I left the room. I went into the dining room and there was Mandy sitting at the table waving me to come over. She emptied both of our book bags so it looked like as if we were studying. She even had two glasses of soda there as well. I sat down at the table where she put my books and studied the glass of soda. Was it the one from before with lipstick on it? I looked closely and didn’t see any. Looking up at Mandy, she simply smiled.

Then we heard the garage door open. Mandy turned to me, “Get studying.” I picked up my English book and began to read. Mandy’s mother came in and saw us. “Hi honey, Hi Johnny. I see the two of are being very studious today.” We both responded back to her as she went into the kitchen. “I better get started on supper before your father gets home.

Are you joining us for dinner Johnny? “ “I wish I could but my mom is expecting me Mrs. Ralston. I better get going.” With that Mandy helped me pack up and saw me to the door. She leaned over to me and whispered, “See you tomorrow sis.” I smiled back at her. We did our normal goodbyes and I went home. The next day in school Mandy came up to me, “Didn’t you have fun yesterday?”

“Strangely I did Mandy. It was really enjoyable. I want to do it again” Smiling Mandy went on, “I’m glad. Today you can try on a few of my skirts. There is one I think will look really good on you.” The rest of the school day was normal. After school Mandy and I walked home together and we spent the rest of the afternoon trying on skirts.

Just about every day after school that became our routine. Going to Mandy’s and dressing like a girl. She worked with me on putting on makeup, walking and sitting like a girl, even picking things up off the floor. It was very enjoyable and refreshing to know that there was a unique part of me that wanted to come out and it certainly did.

About two months later we were sitting in the front room watching TV with me being dressed as Joan. This time I was also wearing a hair wig that Mandy had found in her garage. It was one of her mother’s very old hair wig. She had cleaned it and brushed it very well. When I put the wig on she was really surprised to see how different of a person I looked in it.

She said I really did look like a pretty girl then. When I saw myself in the mirror, I was shocked as her, seeing a nice girl in-front of me. Then we got back to our usual things and we were tired. We had something to eat and then were watching TV. All of a sudden Mandy’s father walked in on us as he came home early. He became cautious when he laid eyes on me.

He was a big man, an ex drill sergeant in the Marines who saw combat. “Well, who is this beautiful lady, Mandy? He asked as he removed his coat. Mandy and I were both shocked and scared at the same time. If he found out that it was me dressed in Mandy’s clothes, he would get very angry. My heart was beating very fast and I was sure Mandy was feeling terrified too. With some courage, Mandy spoke up “Daddy, she is..she is.. my new friend Joan, from school. She is new here and I invited her over.”

“Oh I see! Well you two have fun. I have a lot of work to do.” Mandy’s father then pointed to me and said “Feel yourself at home dear.” And then he went upstairs. Mandy and I both got a bit relieved after that. It was a very close encounter. I was still very nervous and just wanted to run away. But I was also a little proud somehow that Mandy’s father didn’t recognize me at all and thought I was a real girl.

I was still dressed like a girl and in some ways; I could see myself getting excited about it. Mandy then took my hand and we both went into her room. Closing the door behind us, we could hear Mandy’s father talking over the phone.

Mandy was looking very worried and so was I. We could lose our friendship if we were discovered doing something like this. “What should we do Mandy?” I asked. “I am thinking. It was such a close call. I thought we were busted.” She replied nervously.

“Maybe I should just change fast and leave” I said. “No, not till dad is around, you can’t change. If he sees you, we could get into a lot of trouble.” She replied, still a little nervous. “You will have to keep pretending you are a girl.” Then we heard footsteps coming closer to the door. We panicked.

It was her father again. “Hey girls, I have to go to my client’s house right now. There has been an emergency. It might take me an hour before I get home. You girls behave and eat something okay?” Mandy’s father said. We both nodded and in about 5 minutes, he was gone. As soon as Mandy’s father left, I undressed as fast as I could.

Mandy helped me get the makeup off of me. Then I got back into my boy clothes. I felt relaxed now getting back to my normal clothes. I could see Mandy was calmer too. I kissed her cheek and then left. I ran as fast as I could from there to my home. But little did I know that this experience would change me so much later. I was a girl in disguise and even though it was really scary, I liked it.

The End

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  1. Tierna y enternecedora historia, muy emocionante. Realmente me conecte con ella y la disfrute, mil gracias por compartirla

  2. I love your story. That is so sweet how you asked to wear a dress. I had girlfriends but was always cautious about finding a way to confess I wanted to dress. What happened next? Are you and Mandy still girlfriends?

  3. Fabulous story, I would love to live it.

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