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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

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.


“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.”


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.
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
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There 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.
What do you think?
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wendykhill2001 Featured By Owner Dec 6, 2013
wonderfull just loved it more please
flirty-fiona Featured By Owner Nov 19, 2013  Hobbyist Artist
what a lovely story and so good to see how much you injoyed being a girl for a day
eleanorawesome Featured By Owner Oct 27, 2013
artViewer012 Featured By Owner Aug 22, 2013  Hobbyist General Artist
Honestly..... I loved it! Being a crossdresser myself I understand the rush as you realize the fabric feels amazing on your skin. However I will say that I also agree with the thought that describing the feeling of putting on the shoes and lingerie would bring this story up just a little more. As for the story over all I feel it was put together decently just a few more descriptive phrases and I would love it that much more.
ShitAlwaysHappens Featured By Owner Jun 30, 2013  Hobbyist Artist
And I always wondered how it would feel to be a boy and crossdress... :'D
aaronjohn1 Featured By Owner Mar 5, 2013  Hobbyist Digital Artist
I loved it.
embarresedboy3 Featured By Owner Dec 21, 2012  Student
in that case, did sara pass her test thing?
PrincessJessica Featured By Owner Dec 21, 2012
yes she did :)
embarresedboy3 Featured By Owner Dec 20, 2012  Student
i love it but is true or is it fictional?
PrincessJessica Featured By Owner Dec 21, 2012
it's somewhat true. my siste made me wear her dress, but the circumstances might have been exaggerated for laughs
joanmoan1980 Featured By Owner Oct 15, 2012
It is a good story but you do need to proof read more. Also try to add more details about the clothes and all of the makeup.
Pseudowitch Featured By Owner Sep 13, 2012
Minor errors aside, it's a good story with a lot of potential. Perhaps you can type a 'chapter two' where Sara's friends meet her new 'sister'.
Comodine Featured By Owner Sep 7, 2012  Hobbyist General Artist
It is practice makes perfect.

About the plot early is loaded with unnecessary detail if you subsequently ignores the real trigger-TG/CD
Many boys have similar experience (not exactly the same one) by sister,aunt,grandmother, cousin a.s.e... and are no more crossdresser

to be continued...


W. !:
Maybe 'cause English is my fourth language I don't understand the subtleties of your text, so SORRY if I hit you

girlymario3 Featured By Owner Jul 29, 2012
To start off, I want to thank you for adding me to your deviantWATCH list, this was a good story. Too bad I'm only doing one last journal before I give up on getting comments on my journals, it will either be a review of Medabots Rokusho and Metabee versions, a Medabots fanfic, or just a list of my favorite Medabots and Medals, one thing is for sure though it will be Medabots related. There will be a message at the end of it.
ArtistYOU Featured By Owner Jul 17, 2012  Student Artist
Haha, thats nice.
Itachis-killer Featured By Owner May 13, 2012  Hobbyist Photographer
This is Brillient, you have got me a little bit jealous because your sister would do this to you and my sister won't which is what I think but I'm pretty confinced that she wouldn't. I could could try and tell my mum that I wear her cloths but that may take a while.
Cartoonlover2011 Featured By Owner Apr 29, 2012  Student Artist
HEY THAT HAPPENED TO ME TOO!!! but i was with my cousin who's 4 years older than me when she stayed for the weekend and my parents where off to a business trip and my older brother went to his school trip for three days and my sister went to her friends house for a slumber party as well,and my cousin who's a girl dress me up in her clothes,were the same height and weight as me despite bieng older than me i dressed in her red gown and red matching shoes with pink lipstick and red eyeliner I called myself Miss. Red
Dinodragon9000 Featured By Owner Mar 9, 2012
And my last coment I liked it its was actually pretty funny. <3
Dinodragon9000 Featured By Owner Mar 9, 2012
To be honest I would've taken the grounding
Dinodragon9000 Featured By Owner Mar 9, 2012
So wait if u were 15 when ur sister was 16 then how can she be 6 years older then u now
PrincessJessica Featured By Owner Mar 10, 2012
that might have been a typo
Left4fail Featured By Owner Feb 26, 2012  Hobbyist Artist
I love this. It bring back memories of the first time I crossdressed... the difference is that I was the only one involved. Mine was very different. It started with an odd dream one night then the next when no one was home i snuck into my sister's room and actually wore her prom was blue and had sequence on the front of it. anywho it was anazing and I can't stop doing it.
11thdr Featured By Owner Feb 24, 2012
I am very sad theses days because so many people hate me on this forum!
Gypa Featured By Owner Oct 29, 2011
To bad it was mostly fictional, would have made better read if it was real.
dawnvanore Featured By Owner Sep 28, 2011
I thought it ws very well written. The young man seemmed to be smitten with things girly. Loved it!
thetwilightknight Featured By Owner Aug 22, 2011  Hobbyist Traditional Artist
whats it like to crossdress? i have always been curious about crossdressing never tryed it but would like to some day.
PrincessJessica Featured By Owner Aug 22, 2011
well, to me, I jut love the feel of wearing a dress, the material is very smooth sometimes and you just feel like a different person, and it's a good feeling
thetwilightknight Featured By Owner Aug 27, 2011  Hobbyist Traditional Artist
I might just have to try it than ^_^
Gypa Featured By Owner Nov 3, 2011
And did you try it?
jungle-king Featured By Owner Aug 5, 2011
love it
sesshomaruxxx Featured By Owner Jul 27, 2011
great job
Scumdog47 Featured By Owner Apr 23, 2011
For a first story this is quite well written.

I have little or no experience of crossdressing literature so I can't make any judgement on how it compares to other works.

PrincessJessica Featured By Owner Apr 23, 2011
well, thanks. i like all comments/reviews :)
Scumdog47 Featured By Owner Apr 23, 2011
No problem. :)
I'll mail you the link to my own fanfic pronto. :)
JoNaYaOi Featured By Owner Feb 13, 2011  Professional Interface Designer
ashketchum95 Featured By Owner Feb 3, 2011
i love this story you should do a sququel
Yasuna7suzumi Featured By Owner Feb 2, 2011  Hobbyist Artist
Wl i'll write no critique 'll sy it's pretty good ando complaints
Yasuna7suzumi Featured By Owner Jan 30, 2011  Hobbyist Artist
My god this is tru if it is how sad that i truly eny is story blast i still do it privately
Pirate-King-SYR Featured By Owner Jan 11, 2011
Writing is pretty good and it's an interesting short story. I think any girl with brothers has tried to fix her brothers' hair or put makeup on them! Usually much to their disdain ^^;
deepa20 Featured By Owner Dec 26, 2010
nice story :)
ArcaninTheDarkElf Featured By Owner Sep 2, 2010
Awwww :aww:, what a cute story!
I wish that this could happen to me. I'm a in-the-closet crossdresser. My parents hate that stuff!

anyways: Your story is awesome! I really liked it ^^
Your sister sounds like an amazing person. You are soooo lucky.
I would've been sent to the psycho-house if my sister knew! :'(
impact358 Featured By Owner Aug 13, 2010
Nice i like this story i like it alot.

I have a request can you make a sequel of this for halloween?
Undertaker972 Featured By Owner Aug 4, 2010
wow i wish i had an older sister like you. all i have is an older brother who may kill me if he found out that i like crossdressing :( my parents arent much better, since ive been caught twice already, once dressed up, once i left something out and both times my mom was pissed and wondered if i was gay
PrincessJessica Featured By Owner Aug 4, 2010
sorry to hear about that
Undertaker972 Featured By Owner Aug 4, 2010
thank you for that no one even knows im on this site. i have my own laptop so they have no clue
PrincessJessica Featured By Owner Aug 4, 2010
well, that's good
Blufire1992 Featured By Owner Jul 2, 2010  Student Writer
I faved this story... I find it quite funny
GenshiScottKashmir Featured By Owner Jun 10, 2010
“‘"Blackmail’ is such an ugly word” she answered, “I prefer ‘Extortion’, the X makes it sound cool.”" You got that from Futurama, didn't you? Lol. Anyway, great story, but quotes would make it a bit easier to read.
PrincessJessica Featured By Owner Jun 10, 2010
huh? but it IS in quotes.

and yes, I took that from futurama
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