Forced To Dress As A Girl

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Forced To Dress As A Girl

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My sister dressed me up as a girl for Halloween

My name is James. When I was in high school, I started getting fascinated by girl’s school uniform that girls in my school wore. I often fantasized myself dressed as a girl and coming to school as a cute girl.
I have an older sister who is 3 years older than me. She and I are very close and we share almost everything with each other. One day, when mom & dad weren’t around, I asked my sister if she could keep a secret, to which she replied that she would.



I was nervous to speak at first but I finally told her that I kept having an urge to dress up as a girl and feel what its like. I could tell she was pretty surprised by what I said. After some minutes of silence, she asked me if I was joking? But I told her it was the truth.
She then asked me if I was gay? I said I wasn’t really attracted to boys but I just wanted to dress up as a girl and feel cute. She asked if I had dressed up in girls clothes before and I said no. My sister then opened her wardrobe and took out few of her old dresses. I started feeling quite nervous while she was taking out those dresses.
My sister then handed over some of her dresses to me. She asked me to try these on and show her how I looked. I took the dresses and gave her a hug. She smiled and I went to my room to change. I felt a burst of excitement that I had never felt before. I removed all my clothes and decided to wear a white floral dress first. I put them on and immediately I fell in love with how nice it felt to wear a dress.



I looked in the mirror and I couldn’t stop admiring the dress and myself. If only I had long hair, I knew I could really look like a girl. Then I heard my sister calling me and I got very nervous with the thought of walking in front of her while wearing her dress. I slowly walked out of my room and everything felt so different when wearing that dress. I hesitated for a bit to enter my sister’s room but she kept calling me.
When I finally walked in, she looked at me from top to bottom and said not bad, the dress fits you pretty nicely. I blushed. She asked me to come near and showed me a zip at the side of the dress. She pulled it up and it felt like a perfect fit. I just loved how the dress felt in my body.
To my delight, my sister told me I could keep those dresses and wear them whenever I liked. She shocked me by saying that in the coming weekend she would take me shopping for some girly clothes and accessories. I felt very lucky to have such an understanding sister.



Over the next few weeks, my sister got me a new dress, a padded bra and a pair of white stockings. She would give me makeovers and give me tips to present myself more like a girl. We would hang out a lot together and check out women magazines, talk about fashion and other girly things.
It was two weeks before Halloween, my sister had a crazy idea to dress me up as a girl for Halloween and show our parents and few friends. I was spooked by the idea and told her I was just too afraid if they will not like it. My sister convinced me that nothing bad will happen and it will be fun. I finally agreed and she made a plan for Halloween where we would both dress as glamorous Victoria Secrets models. It did sound very exciting.
On the next week, my sister brought me a blonde wig and a pair of black heels. She showed me how to put the hair wig on and when I wore it, she was as surprised as I was with my transformation. She told me I really looked like a girl now.



I realized having long nice hair could instantly make a person look more feminine and pretty. I now looked more feminine in every outfit than before with the hair wig on. I started styling the hair wig to match my face and after some practice, I was able to style the wig better. Every night when everybody was asleep, I would get dressed and also practice walking in heels and work on my feminine manners & postures.
When Halloween arrived, I was super excited. My sister and I started getting ready in her room. I was about to receive a complete makeover by her. She told me how much she liked giving me makeovers and felt like I was her little sister that she never had. I blushed and gave her a big hug.
Then she showed me two dresses and told me to choose one. Both were mini-dress, one was purple and the other was black. I picked the black and she said she would wear the purple one then . I went inside the bathroom and removed all of my clothes. Then, I put on the padded bra and panties, nude sheer pantyhose and the black dress & black heels. I loved how the dress hugged tight around my body and it felt so feminine wearing them.
Lastly, I put on the hair wig last and styled it. I was so happy to see my reflection in the mirror. I felt cute and beautiful. I couldn’t stop blushing. I stepped out and my sister was so pleased with how I looked and kept teasing me. She said now guys would be hitting on me and girls would be so jealous of my looks. I couldn’t stop smiling.



After my sister finished getting ready, she started to do my makeup. She moisturized my face, then applied some foundation and smoothen it out with a makeup sponge. After that, she applied some concealer cream and matched the complexion overall. She then did my eyes and put on eye liner, mascara and some eye shadow.
She also brushed my eyebrows and highlighted the shape with an eyebrow pencil. And lastly, applied a matt pink lipstick on my lips. I loved how girly I looked with the makeup on. I thanked my sister for such a wonderful experience. She told me it was just the beginning. We took a couple of selfies and videos and it was so much fun.
Then she told me it was time to go downstairs and show our parents. I started getting nervous again but my sister took me downstairs to show our parents. I could feel my heart beating so much faster and I was so nervous.
When mom and dad saw me, they were completely amazed how good I looked as a girl and couldn’t believe it. Everyone laughed and my sister kept teasing me. We had some drinks and snacks. I was still a bit uncomfortable but I was glad mom and dad took it pretty well.
Suddenly, my sister told mom & dad that she and I were about to go meet some of her friends and hang out. I was shocked. I didn’t know she had a plan to go outside. I was just too shy & scared to go outside and let other people see me as a girl. I refused but my sister was not taking no for an answer.



She made me get up and as we walked towards the door, I begged her not to take me and meet her friends. She said she knew I would be scared for the first time to go out in public dressed as a girl but this would be a great chance for me to finally feel like a girl . I understood what was trying to say and agreed to go out.
She handed me an eye mask and told me to put them on. She said it will make me feel more comfortable and it did. Now, I had more chance to not get recognized by people whom I didn’t want to see me dressed as a girl. We walked out of the house and it was like I was going out for the first time. There was this huge rush inside my mind and body, I felt so exposed and vulnerable.
Taking the first few steps were very scary but having my sister with me started giving me more confidence. That evening, I meet some of her friends and she introduced me as her cousin from another town, everybody was so nice. We walked around the town and we all had a great time. One of my most amazing experience in my crossdressing journey.
Unbelievable story!! Worth the wait, however all I would add is that the sister should at some point humiliate him or tell him to show her friends his panties embarrassing him hehe
What a lovely story. I wish I had a big sister to dress me up and make me feel so girly xx
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Screwed the Bet, Forced to Cross Dress
Hi, um… I have a small problem. My name is Tom. I’m 18 and I, um, made a bet that the Michigan Wolverines were going to beat the Tennessee Volunteers in football.
Well, it got out of hand and I either pay $250 all around or live like a woman for a week- panties, bra, makeup… the whole thing. I don’t have $500 so I’ll go with the woman thing. I need advice. I’m not asking friends because I want to keep it between us three guys. Please help me. – Dragged to Drag (Franklin, TN)
Sweetness, there are two things you must keep in mind:
1) The only sure thing is that most bets have a 50-50 chance of losing . If you are not prepared to be on the wrong side, don’t bet in the first place. 2) There’s nothing uglier than a macho man dressed in drag.
The only advice I have is find a sister, best girl, or any other female with a sense of humor and borrow some clothes. No one said you need to look like a femme fatal – jeans and a t-shirt, some lipstick, and goop in your hair will suffice. Any tranny will tell you that Payless goes all the way up to a size 13 in women’s shoes… find something you can walk in!
Then it’s your decision to either stay in the house all week and watch daytime TV where you can listen to more fools in a similar predicament to yours or go out and have fun with it! At least you’ll have a zany story to tell your kids down the road.
Hope you’re not pulling my leg with this email, or I’ll have to tell my local she-male, Helga and the Angry Twelve Inch.
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Going to Wedding as a Girl with my Best Friend

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
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