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SISSY BOY AT MILITARY SCHOOL CHAPTER 3 - EARLY ACCESS
🕑 Added 2022-12-27 12:00:02 +0000 UTCWell, Julia chose her outfit for the play and she was really happy about it and so was I. She was even more beautiful in the princess dress and I guess that I already couldn´t have a bigger crush on her. She was so pretty in the dress and she saw how I was blushing when I was looking at her. And maybe that wasn´t bad at all. She knows that I like her … she must know now because she saw how I was looking at her while she was putting on her costume for the school play. But we were going to reverse our roles because now she will be the one who is watching me trying on my costume for the school play… and of course… I will have to wear a maid costume and I just can´t even imagine how am I going to do it. But for her… for Julia… I am willing to do absolutely anything… I really wish to be her boyfriend and this was kind of the best opportunity I have ever had. We are already spending so much time together and this “stupid” school play was another reason to hang out. But of course… there was a cost… I had to play Julia´s maid and I will have to wear a costume of a maid and I was pretty nervous about it. You can only imagine how I felt when Julia said that she was happy with her costume and that it was time for me to choose my maid costume. Fortunately, there was a really nice shop assistant which helped Julia to choose her princess dress and now… she is going to help me to choose my maid costume. I was really nervous and I even started to shiver a little bit. The shop assistant saw how much nervous I was and even Julia stroked my cheek and assured me that everything will be alright.
“Don´t worry about anything, Ben! It is just a costume and once you stop being nervous, you will actually enjoy it! I was nervous as well at first and in the end… I enjoyed trying dresses on!” told Julia, but there was one big difference. She was trying on dresses and she usually wears dresses, but I am not usually wearing a maid uniform… It will be all new to me and I was really nervous.
“Yeah… I am actually trying to enjoy it, but you know… I am really nervous! I just… I have never worn such a thing as a maid uniform!” I said quite aloud and our shop assistant heard that. She came to me and she said:
“No worries, young man! I will help you with everything and you will be a formidable maid! I assure you!” she smiled at me… Well… I wasn´t sure if I wanted to hear something like that… But I obviously didn´t have much choice. I just nodded and I followed the shop assistant to the section where we're uniforms and stuff like that. And then I saw it… I saw the number of maid costumes and I almost fainted. There were so many of them and even in different colours. We came there and the shop assistant asked me:
“So, which colour would you like to try on?”
But even before I could say anything, Julia giggled and she answered instead of me:
“I believe that in the script for a play is a pink and white maid costume!” she said and she was obviously enjoying it so much. Well… there was no worse combination than a pink and white colour. It just can´t get more feminine.
“Of course, we have plenty of them!” answered the shop assistant and then she added: “Of course, in order to wear the maid costume right, you need good underwear and we are selling here some pieces. So… for the pink maid costume, I would recommend you these pink satin panties and a pink lacy bra! And of course, you will need to wear pink nylon tights, but I guess that I don´t even have to say it. It should be a matter of course!”
Matter of course? I almost fainted again when she named all of the things I will have to put on my body. How could this happen to me? Am I dreaming? I guess I am not… and there I was… The shop assistant handed me pink satin panties and a pink lacy bra and she told me to put them on. I had to go to the cabin and I really put the panties on… I had quite a problem with the bra because I had no idea how to put it on…
“Hey… Julia… please come and help me!” I cried out from the cabin and Julia immediately came to me and she helped me to zip the bra on my back. Then she giggled a bit when she saw me in the pink panties and in a pink bra…
“You look really lovely, my sweet Ben!” she said when she looked at me and she just couldn´t help laughing. But I am not even surprised… who wouldn´t laugh. I mean… Look at me! A boy who is just in pink satin panties and a pink lacy bra… That was laughable! But I have to admit one thing. I was actually surprised at how much comfortable these pink satin panties were. It was so smooth and a lot comfier than my reg boy underwear. But I couldn´t say the same thing about my bra… It was so strange and different feeling to have a bra around my chest and it was creating such a strange pressure around my chest. But I guess that I will have to get used to it because I will spend a lot of time in this costume from now on.
Well… the next thing to put on was the pink nylon tights and I again needed help from Julia. The nylon tights were just so fragile and I was afraid to put it on. I didn´t want to make a hole in it. Fortunately, Julia was really so nice to me and she helped me to put it on my legs and OMG… again… it was such a strange feeling. But I can´t say that it was a bad feeling… Maybe… I was about to like it… like feminine clothes because… why not… it is just so comfy and even adorable.
“So… what do you think?” I asked Julia after she helped me with nylon tights. She looked at me and I could see her amused face.
“I think you are the most adorable boy I have ever seen!” she said and it was kind of surprising. I had no idea that one must wear feminine clothes to be adorable. But she didn´t say it as a joke, she really meant it and I liked the way she said it.
“Do you really think so? What is so adorable about me right now?” I asked her.
“Well… just look at yourself! A boy wearing pink panties and a bra with pink nylon tights… I mean… What could be even more adorable than this?” giggled Julia and she said that I just need the pink maid dress in order to make it perfect. And she was right. I still didn´t try the most important part of my costume… the maid dress. And Julia made me wear the most feminine one… pink and white maid dress. But why not… I will look like a girl anyway and the colour of the dress does not really matter anymore.
The shop assistant brought us several types of maid dresses and it was kind of embarrassing to just look at the dresses. It was so feminine and I was blushing so much. The first one was a bit short dress, but it was frilly a lot which was even more embarrassing for me, but Julia told me that I have to try on every single piece in order to decide which one is the best. So there was no other choice but to obey her and I put on the dress. Julia again helped me to zip the dress on my back and then she giggled and told me:
“Pose for me in this dress! I like it so much!”
I had no idea how to pose, but I tried several poses just for fun. And Julia liked it so much that she asked me:
“Ben… you are such an adorable boy! I love it! Pleaseee, may I take some pictures of you in this dress? Pleaseeee, I won´t show it to anybody… just for me!” she almost begged me and back then… I was too naive and I just answered:
“No problem, shall I pose again for you?”
“Yes, please!” she giggled and she started to take a lot of pictures of me in the pink maid dress. And this was just the first dress I put on… And you just have no idea how many maid dresses I had to try on my body. It was like 20 and I was really tired after the last one. But we had our favourite one. It was a pink maid dress which was a bit tight and short, but it was made from a silky material and it was just so cute and really comfortable for me. I tried it several times and of course … Julia took several pictures of me in the dress. Even the shop assistant agreed with our choice and she said that the dress is perfectly fitting my boyish body, which was a bit embarrassing, but it was the truth.
So it was done… we just chose our costumes for our school play and I have to buy the underwear and the bra with nylon tights. But I was actually quite happy to buy it because it was really comfortable to wear except for the bra… but I hoped that I would get used to it.
After I chose the maid dress, I wanted to change back into my clothes, but Julia came to me and she whispered in my ear:
“Please… stay in the panties and the bra… it will be fun! Just for the rest of the day!”
“What? Why?” I giggled and I just didn´t understand it.
“Just stay in the feminine underwear and text me in the evening how did you enjoy wearing it! Please… will you do it for me?” she said and she made those puppy eyes and I just couldn´t say no to her. I just couldn´t.
“Ehm… I mean… Okay! I will text you my experience!” I said and I really kept the bra and panties on. Julia giggled and she kissed me on my cheek. And there… it all started… my highs and lows… it all started with this kiss…
