My Crossdressing Story: Part 1(Author's note: I am writing this at the age of 27, on Monday 26th March, 2018. While it might seem to be a far-fetched account, what you read is true. Everything happened. While I try to write an unbiased entry of my life, some of what I have written might sound biased. I shall leave you, the reader, to make up your own mind.)
It started when I was eleven years old, my fascination for girl's clothing and crossdressing that is. I remember watching my older sister Katie walk around in skirts, dresses, blouses, all clothing that was infinitely better than anything I wore. It looked nicer, and when I hugged Katie, her clothes felt nicer against my skin, a lot nicer. There were times when I was left on my own in the house; my parents were either at work or out for the afternoon, and my sister was visiting her friends. I had freedom of the house, and since my fascination started, I had only wanted to do one thing: try on my sister's clothing.
Many would have found it weird, an eleven ye
My Crossdressing Story: Part 2I step forward in my life, and a lot had changed. Through secondary school things were a lot more different, and it was really the time in which I was able to shine. I gained an appreciation for theatre and dramatic arts, as well as arts in general and singing.My Crossdressing Story: Part 23 years ago in Introductions & Chapters More Like This
That all came during secondary school. I excelled in drama, music and dance, earning A grades for my final GCSE exams, and that train of education continued to college, again taking up drama, music and dance. I was told I had an exceptional singing voice, and to me, that was the ultimate boost for my self confidence. Many commented on the ability to sing with a falsetto which, when performing in musicals allowed me to perform as either a male or female character. I never admitted it to anyone, but I actually enjoyed playing the female parts more than a male. It wasn't just because of the chance I got to enjoy being dressed as a woman, but it was also down to the fact that I could fool people into believing I was a woman, and not
My Crossdressing Story: Part 3If you were to take this story, and use it as an entry on Wikipedia, I imagine it would serve as a good way of chronicling my life. You would start with the early years, then the college years and the build up to the present, which is effectively what this third and final part of my story is. It's a bit of a shame to see it end, but when you think about it, my story won't end just because I have finished writing, in fact it will carry on. You'll all just have to wait and see how it happens. Who knows, I might get famous and become a highly successful and very talented actor on the stage and silver screen. Be sure to keep an eye out for the name Rain Alexander Edmonds on the big screen and you'll know it's me.My Crossdressing Story: Part 33 years ago in Introductions & Chapters More Like This
University was quite a pleasant experience for me, I had a very good time, passed with flying colours, all right the nine grand bill every year was a bit of a downside, but that was something that could be paid off when I started earning money. I went with what became a tradit
My sisterBefore the story starts lets set the scene. Im teenage boy around 13/14 who is spending the week his sisters house. Jess is 21 and lives alone, she's had her house for a couple of months and its not the first time I've spent time over there with her. We both get along like normal siblings and hardly ever fight...My sister2 years ago in Short Stories More Like This
It was a typical average Monday, it was raining quite heavily outside and I had no intentions of going out for the day. I was watching TV in the living room when my sister came into the room. You could tell by the look on her face that she was bored too and desperately wanted something to do. She sat down on the other sofa and watched Jeremy Kyle whilst playing with her hair. She was sat facing me as she played with her hair, after about 30 minutes or so an idea sparked into her head and she left the room. Soon after I heard her return as she sat just behind me. Jess began to brush my shoulder length hair, I knew what she was doing but didn't really react. The sensation of the
My first time crossdressingHello. 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 goMy first time crossdressing8 years ago in General Fiction More Like This
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
Sissy Shopping StoryOne-Handed Reading: Sissy Shopping Story (TG)Sissy Shopping Story4 years ago in Flash Fiction & Vignettes More Like This
"Can I help you find anything?"
The salesgirl's voice startled me a little. I turned and smiled at her, then held up the two tops I had been debating over, one in each hand.
"Actually, yes, you can," I answered, still smiling. "I can't decide which of these to get. Maybe you can help me decide?" The salesgirl nodded and turned her eyes to the shirt I I held out first.
"This one?" I inquired.
It was a lavender stretch shirt, princess seamed with three-quarter sleeves ending in cute turned back cuffs. I already had one similar to it in white, except this one had the longer, more pointed style of collar.
"Or, this one?" I held the second one out for her to see clearly.
This one was a very cute hot pink knit top in a cotton-lycra blend. Very stretchy and form fitting. It, too, had the popular three-quarter sleeves, but these ended in a one-inch ruffle. The neckline was scooped, though not deeply.
"They are both very contemporary styles, ma'am,
I was forced to wear dress as a girlThis is a true story from when I was 13 years old of when I was forced to wear girls clothing.I was forced to wear dress as a girl3 years ago in Short Stories More Like This
My parents were going away for the weekend, me and my sister spent the weekend at our grandmothers house. My grandma lived alone with her cat and was eager to have us over for a few days. She greeted us at the door with a big hug and lots of love. The day was great we had fun and was looking forward to the rest of the weekend.
When I went to go and have a shower I gave gran my clothes to be washed, half way through having the shower it suddenly dawned on me that I had forgotten to bring the bag of clothes that I'd packed. After having the shower I explained to my gran that I had no clothes with me, and we couldn't go and get the bag because we didn't have any keys to the house. Gran paused for a moment and left to go and get some clothes. After a minute or two she came back, and to my surprise she came back with a frilly girls nightie. (At this time I was really quite happy inside, as I was a
Sleepover Part 1Phil and Jenny are brother and sister, their parents were planning on going away for the weekend leaving them both at home. Jenny is 18 and was left in charge being 3 years older than her brother. Because Jenny didn't want to be bored she had arranged to have a sleepover with her friends.Sleepover Part 12 years ago in Short Stories More Like This
Saturday morning their parents left and won't return until the next day. As the door shut both Phil and Jenny kept to themselves, Phil stayed in his room chatting with friends and playing on his xbox. Jenny took over the living room preparing for her sleepover.
It wasn't until around 7:00 when girls for the sleepover started arriving. Phil didn't take much notice but he was surprised how many times he heard the doorbell ring it must of been atleast ten times. The noise coming from downstairs was almost unbearable, it was constant laughing and Justin Beiber music overpowering his TV. Phil turned up his TV until he couldn't hear it anymore. After 10 minutes or so the noise from downstairs went silent, P
A Girl is Born" finally."A Girl is Born3 years ago in Short Stories More Like This
It was 5:00 P.M., and he knew he had several hours to himself. Quickly, he got into his weekly routine, having done it so many times before that he could finish it rather quickly. Every Saturday, Sam's parents would leave from around 6:00 to 11:00, going out to dinner with some friends. And with his sister, Courtney away at college, he finally had some time alone to be himself, or herself. When his sister left for college, she had so many clothes that she just couldn't bring them all with her. She left a lot of the extra frilly and generally feminine ones at home, along with the extra sets of makeup that she didn't need.
After taking out the wig and breastforms he kept under his bed, Sam quickly leaped to Courtney's room; the faster he could start, the more time he could spend as a girl. He put on one of her pink panties and slid them up. After that, he took a matching bra and strapped it on. Being rather thin, and with the long brown wig, he already looked like a girl
Three Dresses for CharlieThe tires made a dull thunk-thunk noise as they ran across the cobble stone street. The bus looked out of place next to 1800s style shops and houses.Three Dresses for Charlie4 years ago in Short Stories More Like This
Just a few blocks away, the town was more modern, though still well-mannered and quaint. But in the town center, there were no cars, and no modern electronics were visible from the street.
Charles got off the bus behind a load of Japanese tourists. He tried to find his bearings from a local street sign, but it was late in the day and the light was getting dim. He had a hard time reading much of anything. He tried squinting harder, but that didn't help. There was a tap on his shoulder, and he turned around.
"You must be Charles." A young woman said smiling. She wore a very formal ruffled white top with a high collar and a knee-length black skirt. Her auburn hair was done up in sausage curls and had a black bow holding it in back. "Yeah I know. It's some get-up, huh?"
"Yes, Sorry for staring I'm Charles."
"It's okay, I just got the ou
Getting in Her Pants"You lost the bet so you have to do it!" laughed Holly.Getting in Her Pants4 years ago in Flash Fiction & Vignettes More Like This
"Yeah, I only bet because I thought I would win, though," Ash pouted, hoping to wriggle out of his predicament. "I wouldn't have even bet otherwise."
"Well too bad, Ash," Holly said getting mad. "And, just because you are trying to welsh on the bet, I am going to make it harder."
"Noooo!" cried Ash in horror.
"Since you said if you won I had to let you into my pants," the girl went on, "I am still going to do that now that you have lost."
"Hmmm, let's see ..." Holly turned to her dresser and started rummaging through the drawers. "I was just going to make you wear a pair of my jeans before." She continued to poke around the drawers as she talked, looking at one thing, then another, discarding another. "But now, I think my new lace-up jeans and a cute top will be much more fun, don't you?"
She spun around and tossed him the pants she spoke of. They were flared jeans, dark blue denim , very soft and form fitting. There were brown le
She's trying to make me a girlAt school in my maths class my teacher moved everybody around into a seating plan. I was put next to this girl that I don't know at the back of the room. I'm quite a shy and quiet person and she is fairly popular.She's trying to make me a girl2 years ago in Short Stories More Like This
We had to work in pairs for the lesson. We was given a large sheet of paper to do our work on, using one of the markers we we're given she wrote our names at the top of the page. I soon noticed that she had put "Steph & Philippa" in pink marker pen, dotting the 'i's with little hearts. My name is Phil and I'm a boy so I asked her why she put that, she started giggling and told me that she has a friend called Philippa and it was a mistake. She looked as though she was about to cross it out before asking "isn't Phil short for Philippa?", I frowned and said no. Steph replied with "Philippa suits you" and didn't cross it out.
Throughout the class she continued to call me Philippa and when I told her to stop she replied with, " aww don't worry, it's cute, you look like a Philippa"
A Silly BrideHow did it turn into this I thought to myself as the girls that had surrounded me continued their giggling and laughter at my expense. But before we get into my current predicament perhaps I should start at the beginning.A Silly Bride2 years ago in Introductions & Chapters More Like This
My name is Alex, Im 18 years old and I am rather on the smallish side for a boy standing at a mere 5 ft inches. Im also very skinny as I weigh a mere 130 pounds. I have light brown hair that falls a bit past my shoulders and some big green eyes.
I had just finally gotten my own apartment in the city which was convenient because this allowed me to be just a few blocks away from where I worked. I always enjoyed walking to work, because I always liked to see the hustle and bustle of the city streets. One store in particular that always seemed busy was a local bridal store that always had some bride and her entourage trying to find the right wedding dress.
I must admit that the whole process was rather confusing to me. Why people would pay thousand
Three Dresses for Charlie Ep.2Part 2: Skirt ShockedThree Dresses for Charlie Ep.24 years ago in Short Stories More Like This
When Charles woke up the next day everything seemed surreal. He had slept in his boy underwear, and he still felt like a boy, but he saw a black and white maid's dress in the corner that everyone expected him to wear today. He thought it might have just been a strange dream, but his room was different; he walked into the bathroom and found Lilly's things. He spent a long time staring at the dress, wondering if he really had to put it on.
Lilly knocked through the bathroom door, cracked it open, and carefully peeked out, "How's it going in there Charlie?"
"I don't know, I'm just kind of skirt shocked. Does everyone expect me to come out in the dress?"
"We were kind of wondering that ourselves. Kate bet Ms. Hughes twenty dollars against it."
"Is Ms. Hughes going to be mad if I don't?"
"I don't think so. She's been more quiet than usual. How do you feel about it?"
"I keep thinking about all the kids at my old school laughing at me."
"You see any of them in town?"
Short Story 2: SleepoverTimmy's sister was having a few friends over for a sleepover. He didn't like playing with them though, so he stayed in his room. Timmy was 12 years old, but his sister and her friends were 15. Sometimes they liked to gang up on him, so he tried to stay out of there way.Short Story 2: Sleepover3 years ago in Short Stories More Like This
Later that night, after dinner, Timmy was in his room playing with his trucks. His sister Beth came into his room with Brittany, Haley, and Kelly. The four of them were smiling at Timmy.
"What is it?" asked Timmy, looking up from his toy trucks.
"Oh you're right Beth!" exclaimed Brittany. "He'll be perfect!"
Haley and Kelly agreed, and the four teenage girls advanced on Timmy.
"Whoa! Wait! Hey what ware you doing!?"
Each girl grabbed one of Timmy's limbs, and they made their way down the hallway to Beth's room. Once they got inside, things happened very fast. The girls dropped him on the bed and went in different directions, each hurriedly getting ready. Beth locked the door while Brittany set up a chair in the middle o
Sister's Little PrincessSister's Little Princess4 years ago in Short Stories More Like This
Sister's Little Princess
I had always been curious about my sister's bedroom. Whenever her friends came over, they would rush up the stairs and slam the door behind them, engaging in secretive girl business. Whenever I tried to join in, she would defiantly throw me against the wall and declare the place 'off limits' to people such as myself. What kind of person was I?
I was a boy.
Banished from these lands, I would never get to experience such amazing things as make-up, gossip, and whatever girls do that makes them so damn loud and annoying. Day after day, I'd see my sister leave her room, the heavy smell of girl closely following her. We'd make eye contact, and she'd step back and slam her door. Out comes the key, in it goes to the lock. The place was a land of mystery.
A mystery, until today.
After having a generously long bathroom break from my homework, I stepped over to the sink to wash my hands. Through the door, I could hear the muffled sounds of a minor commotion
My first story. Crossdress makeoverIt was my sisters homecoming dance coming up in a couple hours and I had a friend over at my house. We stayed in the basement so they pay no attention. While we were playing NBA 2K11, I heard a bunch of laughter and heard someone call my name. I looked behind me and saw at least 20 girls in short dresses and bear feet. I asked what they were doing and they asked if we wanted to go to homecoming. I asked why and found out the answer. I did not like the answer. I signaled my friend to run but they read the signal and started chasing us. It took only a minute until they caught us and blindfolded us. They just held us for a second until they sat us down in chairs. Then they put duct tape on our mouths. As soon as they duct taped our mouths, I felt my clothes being taken off and I felt like I was being tied to a chair. We were vulnerable. Then I heard the girls laughing hard. They left me tied up naked. Once they were done laughing , I felt the ropes being loosened and me being forced to stMy first story. Crossdress makeover2 years ago in Written Suggestions More Like This
All Dolled UpI was getting bored. Kristen and I were watching a movie at her house. She was enjoying the movie, but I couldn't care less about Brad's latest sex flair. Then she sighed.All Dolled Up4 years ago in Short Stories More Like This
"I just don't understand where this is going."
"Where what is going?"
"Us! Where is this relationship headed? We just watch movies on Friday nights and text. Do you even love me anymore?"
"Of course I love you! Where is this coming from?"
I was getting nervous, I didn't know why she suddenly was in a temper tantrum, but I was afraid it was going to end with the end of our relationship, and I didn't want that.
"Its coming from the fact that we never have any fun! Why don't we have fun like we used to?"
"Well, we can have fun! What do you want to do?"
"I don't know, just something we could both enjoy together!"
"This is obviously coming from somewhere, what is it that you were thinking about?"
"Ok well there is one thing that I wanted to try.... but I'm not gonna tell you what
A week with LouiseSchool was over and it was the summer holidays for 6 weeks. Both of my parents we're going away on holiday by themselves leaving me behind. They had arranged for me to stay with my a friend of my mums for the week. My bags were packed and we set off to her house. It was a 30 minute drive before we arrived at the house, I got out of the door and waved goodbye to my parents as they drove off to begin their holiday.A week with Louise2 years ago in Short Stories More Like This
The very second I saw the car turn around the corner I realised that I left my bag containing all my belongings in the car. I'd of called them to turn around but my phone was also in the bag along with all of my clothes leaving me with nothing but the clothes on my back. I walked upto the door and knocked on. I was greeted by a fairly tall woman in her mid 40's. "Hey I'm Louise you must be Philip". "Yes, it's Phil by the way" I replied. "Well Philip sounds better to me" she responded sharply. And with that I was taken into the house. "This is where you will be staying". I open
My hair was put in pigtailsThis morning at school I was dropped off by my grandparents and it was about 30mins early. I went into tutor and sat at my desk waiting for people to start arriving and school to start. After about 5 mins of sitting on my own 3 girls who were in my class walked in talking to each other, I didn't know them so I just ignored them and continued to wait. Shortly after they approached me and sat around me. "How come your sat on your own" one of the asked, I explained to them why I was in so early. "Aww don't worry we'll play with you" she responded giggling. "Can I brush your hair?" One of them asked. I've got shoulder length hair, I replied no. "Your hairs the same length as mine...it could look cute with a few alterations". Before I had chance to respond the girl sad beside me sat on my lap facing me, she was fairly large and quite heavy so I couldn't move. "Get off!" I shouted but they didn't reply.My hair was put in pigtails2 years ago in Short Stories More Like This
With the girl sat on my lap the other 2 girls started brushing and combing my hair. After
Link's NL: Playing Princess 1The pink door slowly creaked open, a small sliver of light illuminating the pitch-black room as a small head poked in.Link's NL: Playing Princess 14 years ago in General Fiction More Like This
"Good... she's not here..." a young voice muttered to itself as its owner slipped into the room, switching the lights on.
Link, or Young Link as he was sometimes known, grinned upon seeing the large, elaborate room. The huge, fluffy bed was perfectly made, the light from the chandelier above completely showing the pale blue wallpaper and multiple portraits on the wall. A vanity table sat against one wall, while a huge closet comprised the other. A glass door leading out to a balcony was visible on the other end of the room. It was a room fit for a princess, and in fact it was; on the door leading into the room was written the name "Peach" in a feminine cursive.
Link grinned as he shut the door behind him. The second Super Smash Brothers tournament had finished a couple of months ago, and everyone had celebrated another rousing success. Sadly, it also meant the young Hy
A Little Too Curious A Little too CuriousA Little Too Curious2 years ago in Introductions & Chapters More Like This
My name is James and I am 12 years old with longish blonde hair and blue eyes I live with my Mum and Dad plus my two sisters Michelle who is 18 years old and Alice who is 15 years old. We often moved a lot and when we did we mainly moved to little country towns. This resulted in us having to make our own fun as there wasn't a lot of other kids around to play with. Well one day my parents needed to go to the next town over and this left me and my sisters with the house to ourselves as my parents wouldn't be back until tomorrow. Well my parents left leaving me and my sisters to our own devices and pretty soon they left to get some food for dinner. The shops were across town and my sisters decided to walk this gave me about an hour to my self. Normally I would spend this time playing video games or playing ball outside but today was different on my way to my room i passed Alice's room and sitting on her bed was what looked like a mix of pink
Girl's Doll (1) I walked quickly up to the door, excited for my first babysitting job. I knocked quickly and a mom and a dad answered. "Hi Bill, we have to leave, so you showed up right on time." The mom said, and they led me into the living room. "The girls are downstairs, remember to feed them later tonight." The dad said, and they left.Girl's Doll (1)2 years ago in Introductions & Chapters More Like This
At least I didn't have to feed them lunch, it was right after lunchtime then. I walked downstairs to meet the three girls. One looked to be about four, one looked five, and the oldest looked six. "Hi guys, what do you want to do first?" I asked enthusiastically. "I want to play with dolls." The oldest one said, and the other two agreed.
"No way, I don't play with dolls." I said, not necessarily trying to be blunt. "But we want to play with dolls!" The girls whined, and I shook my head. The eyes of the oldest one narrowed. "Get him." I raised an eyebrow, just in time for the three girls to tackle me to the ground.
Link's New Look: Playing Princess 2Link sighed heavily as he wandered through the mansion's halls. It had been three weeks since the whole Peach fiasco, and he was glad to have it over and done with. It seemed the princess had kept her promise and hadn't breathed a word of the events to anyone else, but that didn't mean she let him forget it. Every now and then, she gave a little hint about it such as glancing at him when she was discussing her new dress or complaining about her high heels, all with a knowing smirk.Link's New Look: Playing Princess 23 years ago in General Fiction More Like This
Link didn't care, however; he and all the other smashers were leaving in 3 months so they could prepare for the next tournament, so as long as she didn't tell anyone, the whole thing would just blow over. He smiled as he found the wooden door leading into his room and opened it, but the colour drained from the young Hylian's face as he stepped inside.
Pink. Lots and lots of pink. The walls of his room were now covered in a pale pink wallpaper, with a soft carpet in a darker pink covering the forme