Crossdressing Halloween Story
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Crossdressing Halloween Story
Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
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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His Halloween in Her Dress: A Halloween Crossdressing Story Kindle Edition
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When Steve tried to cheer up his housemate Rachael on Halloween, he didn't expect to be wearing the dress and stockings she'd borrowed for a Halloween party. Soon, Steve is 'Stephanie', and helping chaperone Rachael's younger brother and sister in a dress that leaves very little to the imagination, much to the pleasure of all the dads and teenaged boys on their trick or treating route! Once away from her family, Steve is flung in to a party he didn't expect, as a girl. All the strangers seem to think he's a natural woman, but someone he knows doesn't appreciate his get up and decides to out him to the men he's dancing with. As the night draws on, Steve finds himself comforted by his friend Justin, who far from being put off by his pretty outfit, thinks he makes a very sexy woman indeed. As Steve realises how feminine he's become over the evening, will he submit to his girlish side, or run back to the girl he loves? His Halloween in Her Dress is a short story of 11,000 words, full of cross dressing, experimentation, and unexpected sex. It is suitable for adults only. This story also appears in the collection Dressed and Loving It , a bundle of 5 adult crossdressing stories available for Kindle now.
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B00P0HGR7S Publication date
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October 29, 2014 Language
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627 KB Simultaneous device usage
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4.7 out of 5 stars
12 ratings
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Penny Walloon continues to write great stories. University student dresses up as a slutty girl for Halloween. Turns out he looks enough like a girl to fool his girlfriend's father and her brother and sister. After trick or treat girl and boy go to a Halloween party, drugs and alcohol fuel the party and girl passes out. Boy is almost outed by a homophobe,, but he is saved by a young man who is attracted to him. Our hero takes care of his saviour's needs and story ends with all going home. Very sexy story with lots of kissing and dancing. Well written story.
I liked this story. It was so cute and not very explicit, which I enjoyed. Steve becomes Stephanie for Halloween and he passes brilliantly as a girl. I would love a second story with Justin and Steve, to see where their relationship and Steve's cross-dressing could go.
I already reviewed this but being I read it two more time since then I'll do it again. This was the best Halloween story I have ever read and I have read quit a few. The writing is excellent so easy to read the writer should be given a well deserved pat on the back what a great story. I just wish one thing I wish I was him. Great job buy it you will love it like I did. Is there going to be part 2??
I enjoyed this story a lot, I just wish that it kept going!
5.0 out of 5 stars
More a treat than a trick!!!
Although quite a quick read I really enjoyed how this story developed. Much more enjoyable and interesting than many of the typical cross dressing stories. Quite subtly got across the emotional changes which cross dressing can make. The characters also seemed a bit more realistic. Recommended
This was a good read shame that it was a little too short. Would like to have a part two.
5.0 out of 5 stars
Sexy first time
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I love writing tales about love... Slightly kinky love :-) By day I'm sealed in an oppressive '70s office building and like to let my mind wander to more... interesting things. By night... well, what I do with my hubby, my stockings, and a half gallon bottle of baby oil is our own business.
When not being bothered by my shiny suited boss, I like to sneak in a little writing time at work. When I get involved, sometimes I forget about the phone. Sorry about that. One day I hope to be a full time author and leave the fluorescent
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