SALESWOMAN FOR MY MOTHER - CHAPTER 4

Yeah… it was too late for everything. I was going through my punishment and it was really terrible. I felt so embarrassed and guilty. I know and I admit that I was behaving like a stupid spoiled child and I knew that I was so wrong. But Lilly and my mother prepared such a hard punishment. It was really tough to be dressing up in front of Lilly in all feminine clothes and this kind of stuff. And of course… the last piece she brought me was a red short dress with pink nylon tights. I thought that wearing panties and a bra would be enough but it obviously wasn´t. But the red dress and the pink nylon tights… it looked really so feminine and I had a feeling that if I would put it on that I would feel like a girl… so much… All my masculinity would be gone because how could a boy feel like a boy while he is wearing so feminine clothes?

There was no chance of feeling masculine and I almost started crying in front of Lilly. I mean… she was a very good girl and she was kind. But she wanted to teach me that lesson because she thought that it will help me a lot if I would undergo this punishment and she was probably right because after this… I will never ever treat any person like I treated Lilly at first… Never… because I want never ever get into a situation like this! Never! This was too humiliating and I don´t want to go through this again.

“Come on, Peter… don´t look so scared! It is only a red short dress! It won´t bite!” Lilly giggled when she saw me just standing there. I was almost unable to move… to even put the dress on.

“Lilly… I mean… it is all so much feminine… I still want to be a boy, you get it? If I put on all this feminine stuff on my body… I won´t feel like a boy anymore!” I protested.

“Oh… don´t worry! It won´t be that bad! I am sure that you will still feel like a boy there will be a huge difference! You will know how girls feel in their clothes and you obviously need to know this! But I explained this to you before! Now… As I said… put on the dress! I want to see you in the dress and one of us must be behind the counter and serving our customers!” Lilly told me.

“Well… it can´t be me, Lilly… I definitely can´t go there dressed like this… just look at me… everybody would see that I am just a boy wearing a red short dress! Please… don´t make me do it, Lilly… please… I beg you! I will be a good boy here in the warehouse and I will do all the paperwork and all the stuff in here… but please… don´t make me talk to our customers…” I begged her.

“Peter… you don´t have to worry about it… when you put the red dress on… I will bring the blonde wig and I will put makeup on your face so nobody will ever recognize that you are a boy! Do you get it?

“Whaaat? Are you serious? The wig? The makeup? But no… you just can´t do it! Please… don´t do this… Isn´t feminine clothes enough? Isn´t this already a huge punishment?” I asked her.

“Oh no… we are just in the beginning, Peter! Now… enough talks and put on already the red dress so I can continue with the makeover!” she added and her voice became really strict. And I had to obey her because it would take only one phone call from her to my mother and my mother would leave me here to work for the rest of the year and I just couldn´t imagine that. I couldn´t imagine being here longer than a month! And even the month will be too long for me.

“Okay… okay… I will put the dress on… just pleaseee… don´t laugh at me…. the laughing makes me feel even more embarrassed!” I said. Lilly looked at me and said:

“Embarrassed? Again? Why would you feel embarrassed?” she asked me.

“Well… because I am a boy and I have to wear these feminine clothes! That´s why I feel embarrassed! Isn´t this quite obvious?” I answered and I almost got angry. She was telling how important it is to know how girls feel but she also had no idea how boys feel when they are forced to wear feminine clothes! She has no idea… But Lilly again looked at me and said:

“No… it isn´t obvious, Peter. And you definitely shouldn´t be ashamed of wearing feminine clothes! But we talked about this before! Women aren´t embarrassed as well when they are wearing jeans and shirts… so you shouldn´t be ashamed of wearing dresses and feminine clothes in general. You are ashamed because you think that men are more important than women and you think that women are weak! And that is why you feel embarrassed while wearing our pretty feminine clothes! But I am sure that you will eventually adore and love it because you will find out that our feminine clothes are far more comfortable and prettier than your clothes!”

“Okay… I guess that we will have a very different opinion about this… but okay… I get it… I know you want me to have this punishment and I know that you can call my mom and tell her that I don´t obey and she would order me to stay here for another month at the very least… so okay… I am already dressing up!” I said and took the short red dress into my hands. I stepped into it and Lilly helped me to zip it on my back… suddenly… I felt… really different. It was such a strange feeling to be wearing a dress. It was for the first time in my life… But I have to say that it wasn´t actually that bad. As Lilly said… the dress was really comfortable… In the end… it was quite okay to wear it but… I just couldn´t imagine myself in the shop… Customers just can´t see me like this.

“Wow… I didn´t expect you to be so pretty in the red dress! It looks really good on you! I think that it is good that we chose the red dress. The yellow one would be good as well but this will make you even more feminine which is our goal!” she giggled. “And tell me… how do you feel? Do you like your new dress?” she asked.

“Ehm… to be honest… I didn´t expect this feeling! I mean… it is for the first time for me… I have never worn any feminine dresses so I had no idea what it feels like to wear a feminine dress. But you were right. It is quite comfortable!” I answered.

“You see? I told you! I told you that! I told you that you will actually like wearing it! I am so glad you love it! I am so glad!” Lilly giggled. “And… since you fell in love with our pretty feminine clothes… you must have makeup on your face because it will make you so much more beautiful! I know it! You are already so much cute but the makeup will just boost it!” she giggled and she brought her makeup tools. And when she started to unpack it… I thought that I would faint because it looked like a makeup army… She had so many things in her makeup bag and I had no idea how are all these things were even called.

“Wait… Lilly… isn´t this… isn´t this probably too much? I think that it won´t be needed!” I tried to save my skin from the tons of makeup.

“Nonsense, my dear… you will definitely need a lot of makeup because we just have to hide every single masculine part of your face and it won´t be easy at all!” she said and added: “Well… we will start with the makeup foundation… I am gonna put two or three layers because it will be needed!” she said and started applying makeup to my face. I had to be steady and I wasn´t even allowed to move my head. But I got it… it had to perfect and again… I just had to obey because otherwise…. I would spend the rest of my life here as a shop assistant and as a woman and I definitely didn´t want it.

“Well… I think that we are finished!” said Lilly and it made me quite happy because I hoped that it is all done.

“Finally… so…can I start working?” I asked her. Lilly started to laugh so much that she even couldn´t answer my question. I didn´t get what was so funny… I asked her several times why she was laughing that much but she didn´t answer me because she was still laughing so much. It took her a few minutes to calm down and then she finally answered:

“Oh, Peter… my dear… we are finished just with the foundation… the makeup is really a long journey to go! This was just the first step… you know?” she answered.

“The first step? But it took you almost half an hour to make the first step!” I cried out.

“Yeah… that´s why I tried to rush you into the dressing up. The makeup will just take its time! You can´t rush it otherwise… it wouldn´t look good at all!” she said.

“So… we are not finished… I guess!” I said with a sad voice.

“No… we are not… but be happy about it… you can enjoy more and more moments like a girl and it is a huge privilege for you!” she giggled.

Well… I had no idea what was the privilege… being just totally crossdressed and almost feminized. But I had to pretend that I was happy because she still could call my mom. So I was sitting there and waiting for more and more makeup… and it came…