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literature
My first time crossdressing
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Hello. This is my first crossdressing story. It’s from a first person POV, and it’s fictional but there are some aspects of my experience, I just changed the names to protect the innocent. Now here we go
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Greetings! My name is James, just James for now. I live in a home with my parents in New York. I’m age 17 and I have an older Sister, Sara, who is three years older then me. Oh, and did I mention that I’m a crossdresser? I guess I should start from the beginning.
Well, it all started a few years ago, when I was 15. The date escapes me, but it was the few days that were after my Sister’s Sweet 16th party; we held it at a fancy Hotel and it was themed to one of her favorite movies: Cinderella. Sara wore an elegant blue gown, just like Cinderella and her long dark brown hair, similar to mine, was in a very festive knot. She usually has it loose all the time, but during the party, she decided on a knot. Well, the few days later in question, was a Saturday and she was working on a final project for her salon school. Ever since she was younger, Sara wanted to grow up as a hair-stylist. Her final project involved a hairstyle she would use on a dummy plaster head. This is where I came in. I was in the other room, watching cartoons until I finally got bored. Mom and Dad left the house to go shopping and they wouldn’t be back until later, leaving me and my sister alone for the day. I when into Sara’s room and saw her doing her project, but I was hoping that she could stop for a little while.
“Hey, Sara, do you think you can put that head away for a minute and do something with me?” I asked, slightly bored.
“No, James, I have to finish this thing otherwise I won’t get a passing grade.” She said in a frustrating tone.
I then said in an annoyed tone, “Come on, I’m bored.”
“Why don’t you read a book?” She asked hopefully.
I replied, “Because I’m trying to reduce my boredom.”
“James, I really can’t talk right now. This hairstyle has to be perfect to pass the grade.”
I finally gave up on her. “Fine, I’ll just do something by myself”, and left to go to my room.
When I entered my room, I when through my junk drawer/underwear drawer, all the stuff I collect over the years ended up in this drawer. I searched and pulled out my blue hand ball. I began playing hand ball and used the wall in front of me to hurl the ball. I was playing for 5 minutes straight, all without missing the ball, back in school I was the handball champ. It was after the 5 minutes, while I was completely focused on the game, my sister came charging in.
“CUT THAT OUT, ALREADY!” She shouted.
Her shout made me lose my focus and caused me to hit the ball as hard as I could. The ball ricocheted off the wall and I had to duck because it was moving so fast. The ball bounced off the wall behind me was heading towards Sara. She ducked and the ball bounced off the wall and into my sister’s room. Because her room was right across from me and the door was at an angle, the mall made its way in and hit the plaster head she was working on. We both gasped as the head began to tumble and fall off the Vanity Mirror it was on. I closed my eyes as I heard the crash.
“My head!” Sara shouted.
I opened my eyes and sees that the hair fell off of the head, since it was a wig, and the head’s top was chipped off.
Sara was upset. “Look what you did!”
I replied “‘what I did?’ Everything was fine until you barged in and made me lose my focus.”
Sara picked up the head and looked at me angrily, “Look at this thing! It’s totaled.”
“Oh come on, now, it’s not that bad. I’m sure we can re-glue the top and it’ll be as good as new” I said encouraging.
“By the time it’s fixed, I won’t have time to finish. And I can’t do it tomorrow, I’m hosting my slumber party “
That’s right, I almost forgot. Sara invited a few of her friends for a slumber party tomorrow. Now I started to feel bad, I never meant to do this to her.
“I’m sorry, Sara. Is there anything I can do to help?” I asked.
She was looking at the head, then the picked up the wig that was on it, and then she looked at me. After a moment a two she began smiling, which scared me a bit because it looked a bit evil.
“Well, I suppose you can help me. But you must stay to your word” she said.
I gulped, “Uh… Yes, I give you my word.”
“What I need is a head to continue my work, and while I wait for the glue to dry, I can use the wig on your head” she said just after she smiled evilly at me.
“What?!”
“You said you’d do anything for me.”
I sighed. “I guess I did say that.” I paused before I replied, “Ok, you can use my head.”
“Terrific.”
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A few minutes later, I was standing outside my sister’s room. She was setting things up and fixing the head as I waited. How did I get myself into this mess? Well, at lease it was just my head she needed, it’s not like she was gonna-
“James, I’m ready for you.”
My thoughts were derailed as I entered Sara’s room. She has set a chair in front of the mirror for me. Perfect, now I have to watch myself while she worked.
“Ok, let’s get this over with.” I said.
“Hold on”, she said. “Before we can begin, I need you to wear this”
She held in front of me her blue Sweet 16 gown. I looked in horror as I saw the dress. She expected me to wear her dress as she worked on the wig? Oh, hell no!
“Wait one moment!” I yelled, “I never agreed to-“
“Oh, I know,” she interrupted me, “this is just a little punishment for breaking my head in the first place. Of course, we can just forget about it and I tell mom and dad you broke my head, and they’d ground you for it.”
“You’re blackmailing me?” I asked in fear.
“‘Blackmail’ is such an ugly word” she answered, “I prefer ‘Extortion’, the X makes it sound cool.”
I growled under my breath, and then I sighed. She would have this on me until mom and dad got home. I gave up “… Ok, Sara. I’ll do it. I’ll wear the dress.”
“Splendid, now take off your shirt and pants.”
I couldn’t believe this as I began to undress myself. She held the dress and opened the back as I finished. I took the dress from her and I began to step into it, feeling the soft lace and the smoothness of the material gave me Goosebumps. I pulled it up to my chest and she began to zip me up, since I was younger then her, the gown fit like a glove. I started to blush in embarrassment as I walked to the chair, feeling the dress swish as I walked. She then placed the wig, which was the same color as my hair, on my head. I recently got a haircut, so the wig fit well into place. I stared at my reflection in the mirror, with the wig and dress on me; I actually looked like a girl.
“Now my little sister,” She giggled, “Let’s do your hair.”
I just stared and waited as she began working on the wig and talking about how pretty I looked. I was too shocked to do or say anything. It was an hour later that she had finally finished. She had the hair held up and into a stylish ponytail, with a few messy strains around my face.
“There, all done.” She said finally. “What do you think? Do you like it?”
I gave no reply at first. I just got up and looked at the full length mirror she had by the door. I looked at myself, or rather the girl I see in front of me. I turned to the side. Held my hips with my hands and lifted the dress up a bit. I finally spoke.
“You spend the last hour humiliating me, making me wear your dress and turned me into your little practice dummy, and then you ask me if I like it?”
There was anger in my voice as my sister looked at me, wondering what I was gonna say next.
“No, I don't like it!” I paused for a moment, then I said in a somewhat happy tone, “I Love it!”
Sara looked completely shocked at what I said. “You… what?”
“I love it. At first I didn’t like it. But after I saw myself dolled up like this, I loved it. The dress, the wig, the way I look like a real girl, I though I would hate it, but this dress feels so good on me.”
“You… really like it?” Sara asked in a somewhat surprised tone.
“Yes. In fact, it makes me wonder how it would look and feel if I was all girl. the shoes, the make-up…” I giggled in excitement. “You gotta do more on me. Give me a complete makeover!”
Sara looked at me, thinking, “Well…” She pauses, and then she giggled. “Ok, I’ll do it. I’ve always wanted a little sister. Ok, get back into the chair. I’ll give you your makeover.”
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So for the next hour, we began my complete makeover. I took off the dress because she wanted me to wear her bra and panties, which I agreed to wear. She put stockings on my legs and fitted her high heeled shoes on me. I put back on the dress and wig and started with the make-up. She put on purple me eye shadow, light foundation, pink nail-polish, blush and pink lipstick. I got up and began dancing and walking all around; Sara taught me how to walk in heels, I also spun around, feeling the dress lift up as I spun. I lifted my gown as I curtsied and I loved every minute of it. As we had our fun, I heard a car entering the driveway, it was mom and dad. They were home.
“Oh-no,” Sara said, “Mom and dad are home. Quick, get out of that dress.”
I got scared as I started to take off all of the female clothing I had on, including the wig.
“I’ll take care of this; you go in the bathroom and wash all that make-up off.”
She passes me Nail-Polish remover and I hurried off to the bathroom. I locked the door and I started the shower to get the make-up and Nail polish off. My parents came home as I was in the shower, they had all sorts of packages from the store they when too.
“Hi, mommy, daddy.” Mi sister said as she welcomed our parents in.
“Hi, Sara,” said mom, “Where’s your brother?”
“He’s in the shower”, Sara answered.
It was around that time I got out of the shower in a towel, the make-up and nail-polish, all off of me.
“Hi, mom.” I said.
“Hi, sweetie” said mom. “Did you have a good day while we were gone?” she asked.
And I answered, “Yeah, mom, I did have a good day.” I sent a secret smile at Sara and she just giggled silently.
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There goes my first story. Please tell me what you thought of it. Thank you.
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Greetings! My name is James, just James for now. I live in a home with my parents in New York. I’m age 17 and I have an older Sister, Sara, who is three years older then me. Oh, and did I mention that I’m a crossdresser? I guess I should start from the beginning.
Well, it all started a few years ago, when I was 15. The date escapes me, but it was the few days that were after my Sister’s Sweet 16th party; we held it at a fancy Hotel and it was themed to one of her favorite movies: Cinderella. Sara wore an elegant blue gown, just like Cinderella and her long dark brown hair, similar to mine, was in a very festive knot. She usually has it loose all the time, but during the party, she decided on a knot. Well, the few days later in question, was a Saturday and she was working on a final project for her salon school. Ever since she was younger, Sara wanted to grow up as a hair-stylist. Her final project involved a hairstyle she would use on a dummy plaster head. This is where I came in. I was in the other room, watching cartoons until I finally got bored. Mom and Dad left the house to go shopping and they wouldn’t be back until later, leaving me and my sister alone for the day. I when into Sara’s room and saw her doing her project, but I was hoping that she could stop for a little while.
“Hey, Sara, do you think you can put that head away for a minute and do something with me?” I asked, slightly bored.
“No, James, I have to finish this thing otherwise I won’t get a passing grade.” She said in a frustrating tone.
I then said in an annoyed tone, “Come on, I’m bored.”
“Why don’t you read a book?” She asked hopefully.
I replied, “Because I’m trying to reduce my boredom.”
“James, I really can’t talk right now. This hairstyle has to be perfect to pass the grade.”
I finally gave up on her. “Fine, I’ll just do something by myself”, and left to go to my room.
When I entered my room, I when through my junk drawer/underwear drawer, all the stuff I collect over the years ended up in this drawer. I searched and pulled out my blue hand ball. I began playing hand ball and used the wall in front of me to hurl the ball. I was playing for 5 minutes straight, all without missing the ball, back in school I was the handball champ. It was after the 5 minutes, while I was completely focused on the game, my sister came charging in.
“CUT THAT OUT, ALREADY!” She shouted.
Her shout made me lose my focus and caused me to hit the ball as hard as I could. The ball ricocheted off the wall and I had to duck because it was moving so fast. The ball bounced off the wall behind me was heading towards Sara. She ducked and the ball bounced off the wall and into my sister’s room. Because her room was right across from me and the door was at an angle, the mall made its way in and hit the plaster head she was working on. We both gasped as the head began to tumble and fall off the Vanity Mirror it was on. I closed my eyes as I heard the crash.
“My head!” Sara shouted.
I opened my eyes and sees that the hair fell off of the head, since it was a wig, and the head’s top was chipped off.
Sara was upset. “Look what you did!”
I replied “‘what I did?’ Everything was fine until you barged in and made me lose my focus.”
Sara picked up the head and looked at me angrily, “Look at this thing! It’s totaled.”
“Oh come on, now, it’s not that bad. I’m sure we can re-glue the top and it’ll be as good as new” I said encouraging.
“By the time it’s fixed, I won’t have time to finish. And I can’t do it tomorrow, I’m hosting my slumber party “
That’s right, I almost forgot. Sara invited a few of her friends for a slumber party tomorrow. Now I started to feel bad, I never meant to do this to her.
“I’m sorry, Sara. Is there anything I can do to help?” I asked.
She was looking at the head, then the picked up the wig that was on it, and then she looked at me. After a moment a two she began smiling, which scared me a bit because it looked a bit evil.
“Well, I suppose you can help me. But you must stay to your word” she said.
I gulped, “Uh… Yes, I give you my word.”
“What I need is a head to continue my work, and while I wait for the glue to dry, I can use the wig on your head” she said just after she smiled evilly at me.
“What?!”
“You said you’d do anything for me.”
I sighed. “I guess I did say that.” I paused before I replied, “Ok, you can use my head.”
“Terrific.”
---------------------------
A few minutes later, I was standing outside my sister’s room. She was setting things up and fixing the head as I waited. How did I get myself into this mess? Well, at lease it was just my head she needed, it’s not like she was gonna-
“James, I’m ready for you.”
My thoughts were derailed as I entered Sara’s room. She has set a chair in front of the mirror for me. Perfect, now I have to watch myself while she worked.
“Ok, let’s get this over with.” I said.
“Hold on”, she said. “Before we can begin, I need you to wear this”
She held in front of me her blue Sweet 16 gown. I looked in horror as I saw the dress. She expected me to wear her dress as she worked on the wig? Oh, hell no!
“Wait one moment!” I yelled, “I never agreed to-“
“Oh, I know,” she interrupted me, “this is just a little punishment for breaking my head in the first place. Of course, we can just forget about it and I tell mom and dad you broke my head, and they’d ground you for it.”
“You’re blackmailing me?” I asked in fear.
“‘Blackmail’ is such an ugly word” she answered, “I prefer ‘Extortion’, the X makes it sound cool.”
I growled under my breath, and then I sighed. She would have this on me until mom and dad got home. I gave up “… Ok, Sara. I’ll do it. I’ll wear the dress.”
“Splendid, now take off your shirt and pants.”
I couldn’t believe this as I began to undress myself. She held the dress and opened the back as I finished. I took the dress from her and I began to step into it, feeling the soft lace and the smoothness of the material gave me Goosebumps. I pulled it up to my chest and she began to zip me up, since I was younger then her, the gown fit like a glove. I started to blush in embarrassment as I walked to the chair, feeling the dress swish as I walked. She then placed the wig, which was the same color as my hair, on my head. I recently got a haircut, so the wig fit well into place. I stared at my reflection in the mirror, with the wig and dress on me; I actually looked like a girl.
“Now my little sister,” She giggled, “Let’s do your hair.”
I just stared and waited as she began working on the wig and talking about how pretty I looked. I was too shocked to do or say anything. It was an hour later that she had finally finished. She had the hair held up and into a stylish ponytail, with a few messy strains around my face.
“There, all done.” She said finally. “What do you think? Do you like it?”
I gave no reply at first. I just got up and looked at the full length mirror she had by the door. I looked at myself, or rather the girl I see in front of me. I turned to the side. Held my hips with my hands and lifted the dress up a bit. I finally spoke.
“You spend the last hour humiliating me, making me wear your dress and turned me into your little practice dummy, and then you ask me if I like it?”
There was anger in my voice as my sister looked at me, wondering what I was gonna say next.
“No, I don't like it!” I paused for a moment, then I said in a somewhat happy tone, “I Love it!”
Sara looked completely shocked at what I said. “You… what?”
“I love it. At first I didn’t like it. But after I saw myself dolled up like this, I loved it. The dress, the wig, the way I look like a real girl, I though I would hate it, but this dress feels so good on me.”
“You… really like it?” Sara asked in a somewhat surprised tone.
“Yes. In fact, it makes me wonder how it would look and feel if I was all girl. the shoes, the make-up…” I giggled in excitement. “You gotta do more on me. Give me a complete makeover!”
Sara looked at me, thinking, “Well…” She pauses, and then she giggled. “Ok, I’ll do it. I’ve always wanted a little sister. Ok, get back into the chair. I’ll give you your makeover.”
---------------------------------------
So for the next hour, we began my complete makeover. I took off the dress because she wanted me to wear her bra and panties, which I agreed to wear. She put stockings on my legs and fitted her high heeled shoes on me. I put back on the dress and wig and started with the make-up. She put on purple me eye shadow, light foundation, pink nail-polish, blush and pink lipstick. I got up and began dancing and walking all around; Sara taught me how to walk in heels, I also spun around, feeling the dress lift up as I spun. I lifted my gown as I curtsied and I loved every minute of it. As we had our fun, I heard a car entering the driveway, it was mom and dad. They were home.
“Oh-no,” Sara said, “Mom and dad are home. Quick, get out of that dress.”
I got scared as I started to take off all of the female clothing I had on, including the wig.
“I’ll take care of this; you go in the bathroom and wash all that make-up off.”
She passes me Nail-Polish remover and I hurried off to the bathroom. I locked the door and I started the shower to get the make-up and Nail polish off. My parents came home as I was in the shower, they had all sorts of packages from the store they when too.
“Hi, mommy, daddy.” Mi sister said as she welcomed our parents in.
“Hi, Sara,” said mom, “Where’s your brother?”
“He’s in the shower”, Sara answered.
It was around that time I got out of the shower in a towel, the make-up and nail-polish, all off of me.
“Hi, mom.” I said.
“Hi, sweetie” said mom. “Did you have a good day while we were gone?” she asked.
And I answered, “Yeah, mom, I did have a good day.” I sent a secret smile at Sara and she just giggled silently.
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There goes my first story. Please tell me what you thought of it. Thank you.
The story of a young boy and his first time in a dress. Please leave a comment
Comments106
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Overall Vision Originality Technique ImpactThere is a clear sense of roughness in this author’s writing style. Further practice and rigorous proofreading will iron out those wrinkles in the future, I believe. However, some plot points may cause the reader to scratch their head in confusion. For example, James mentions in the first paragraph that Sara, his sister, is three years older than him. However, in the very next paragraph James says that his cross-dressing began when he was 15, and it happened a few days after Sara’s 16th birthday party. Also, how does a princess dress for a 16 year old girl fit a 15 year old boy like a glove?
The biggest problem is not with plot holes, however, but the characters. At the beginning the reader knows very little about James or Sara, and both characters go on to do very strange things. Sara dresses James up in her clothes and James finds out that he loves it. This isn’t in itself a problem (stories with strange plot points are often the most interesting ones), but the reader has no idea why either character would behave this way. What happens in the story then ends up seeming random and contrived. Characters need to have their personalities established early in the story so that the reader can understand why they do the things they do. Perhaps James has loved feminine clothing all of his life, or perhaps Sara enjoys humiliating her brother. Either could be right in the context of the story, but without any clue in the text the reader has no way of knowing that. In a story which is most of the action is James and Sara interacting with each other, the lack of developed characters makes for a rather confusing read.
The strongest aspect of the story is something that is unfortunately glossed over: the clothing and makeup. As a reader I am repeatedly drawn to the second paragraph where the author describes Sara’s birthday party, her dress, and her hair style. When the dress reappears the description of James putting it on is quite evocative. He puts it on, describing the feel of the fabric, the swish of the skirt, and a blush of embarrassment. Here James’s character starts to come alive as the reader gets insight into his mind. There was the possibility of using this style of writing to describe putting on the makeup, lingerie, and shoes, but these activities were only glanced over.
I look forward to a continuation of this story in which these two characters have further familial adventures in fashion, and where the reader will be treated to the author’s vivid descriptions of cross-dressing to a greater degree.