Dear Auntie Helga,
On Saturday I was told I would be going shopping with a specified list of tasks to do while there by my Mistress Amber. I did not look forward to this at all because I have not been out hardly at all either dressed or or partially dressed and I was extremely apprehensive about it but as a sissy I have no choice but to comply with my Mistress Amber's wishes. On the morning of the shopping trip I had to pluck my eyebrows into a thin line and accent them with an eyeliner pencil and also apply mascara to my lashes, I was almost in tears having to do this because it definitely brought attention to anyone that looked closely at my eyebrows and lashes.
Then I was dressed in panties, stockings, garter belt and a pair of skinny jeans that were definitely feminine by the embroidery and the embellished belt that I had to wear with it. Then I had to don a bra and a white , almost see through blouse. I was not allowed to zip up my coat past my breastbone so if anyone was to look very hard at all they would see that I had a bra on.
My feelings were absolutely devastated about this outfit. I then had to apply two coats of bright red nail polish to my fingernails which stood out terribly. When we got to the mall I had to make two rounds of it before I could commence my tasks, with my hands visible at all times. The first task was to buy a white clutch bag and a powder compact but I had to go to at least three stores first before purchasing one. After the purchase I transferred all my money and phone into it. I left the store with the new clutch in the shopping bag and proceeded to my next task.
Before going into jewelry store to buy a medallion to be engraved on one side with "sissymaid andrea" and on the other with "Property of Mistress Amber", and a chain for it to hang on, I had to take out my compact and check my appearance which drew some amused looks from some passersby and I thought I heard a couple of giggles as well. I was so nervous walking into the store. At the counter the sales girl who waited on me was rather amused by my request, She was in her late thirties probably and asked if it was for me to which I had to reply "yes it is". she then asked if I was a sissy and I told her I was a sissy in training right now, she gave me a knowing smile and said "how sweet, bet you will make a very cute sissy with your pretty nails and all". At that point I could have gone through the floor and my knees became a bit weak, I was totally embarrassed by the time I left the jewelry store.
Then it was on to the drug store to purchase two packs of "super" tampons, I didn't know why I need those till later but the girl at the cash register looked at my nails and I am sure she noticed the mascara and plucked eyebrows although she did not say anything but I was never the less falling deeper into despair as I had to go to a lingerie store next. Once again taking out my compact to check my appearance before entering I meekly went into the store and a young girl in her twenties at most asked to help me. This was my most humiliating experience so far as I had to tell her I wanted a bra and panty set in pink and bright red. She then proceeded to show me every bra in store it seemed and I was ready to just get something and go.
The sales girl asked what size and if it was for me and I replied that yes it was that I was a sissymaid in training, she said "Oh how sweet, we will find you a cute set to wear". She even held them up to me in front of a mirror and I noticed a few women glancing at me and a few wry smiles which I am sure had me turning red in the face. When we picked out my lingerie she also commented on my pretty red nails and asked if I kept them polished all the time. Another moment I could have gone through the floor as I told her not all the time but a lot, but when my Mistress required me to.
Then I had to get 4 pairs of black stockings and of course she asked me again if they were for me, she was enjoying my humiliation a lot. After paying for the items she told me to come back and she would be pleased to help me with more sissy items when I was ready for some more stuff. I replied thank you and I would and hurriedly left the store. Then I went off to the department store to purchase lipstick. Once again I had to check my appearance with my compact and entered the store with an increasing amount of dread. This time it was an older lady and when I told her I needed some lipstick to match my nails she said "Oh my aren't you the cutest thing", I thanked her and told her I needed lipstick because I was a sissymaid in training and my Mistress required me to look pretty when serving her. She replied that I would most certainly make a pretty sissymaid and she would love to see me all made up. After recommending a very glossy bright red lipstick I had her to recommend some lipstick in a color that matches my skin tone.
She also told me the best way to apply lipstick and offered to demonstrate. I was instructed by Mistress Amber to let them show me if they offered. She applied it to my lips to my surprise, I certainly was not expecting that, She also sold me a lip liner pencil to go with it. When she was done she said my lips were so pretty that they would be hard for someone to resist at which point I almost lost it but said "Thank you". My last items were to purchase false eyelashes there.
Then I had to go to a perfume counter in the store and once again tell the sales girl I was a sissymaid in training and I needed some perfume. She picked out a fragrance called Gucci Bloom, and said it was appropriate for a sissy like me. I have never been so embarrassed and humiliated in my life. She then proceeded to apply it quite liberally on me before asking what kind of training I was doing. I replied that I was my Mistresse's sissymaid and did all the housework and other tasks she assigned, then she floored me when she said she had heard of that and a lot of Mistresses put their sissies in chastity.
I must have had an obviously chastised look on my face since she said your Mistress must believe in it too. I replied as required that yes she did. She thought that it was a fascinating concept and asked me how long I had been in chastity and was it full time. I replied it had been quite a few months and yes it was 24/7 chastity. She said oh you poor thing but I guess as a sissy you do not really need that anyways do you, I replied no ma'am I do not get to use it at all. she said it was probably for the best anyway and wished me a good day and to come back to see her sometime. I proceeded to hurry out of the store and to the parking lot to return home.
After returning home I was subjected to 25 strokes of the paddle, followed by 50 strokes of the belt for not holding my clutch after I got it. It was not supposed to be put back in the shopping bag. I am grateful to Mistress Amber for this exercise and she has informed me that the end goal is for me to go out fully dressed and be acceptable so as to not embarrass myself or my Mistress. I am sure there is another trip to the mall in store for me and I am anxiously looking forward to it.
Thank you for your letter Sissymaid Andrea, I'm sure this must have been a humiliating experience for you but like many other things sissies do it involves being in embarrassing situations, these are all meant to help you to become comfortable being in public to do your Mistress's bidding, shopping, dry cleaning and such and in time you will relax and feel more comfortable with witnesses knowledge of you being a sissy.