Shopping for & Wearing a Dress by sophie

Dress Shopping Following a discussion, Mistress Magick agreed that I should wear a dress and make up while I wrote my lines for getting distracted while panty shopping.

I started looking on the internet at sites for some of the local women's clothes shops. I looked at New Look, George, Peacocks and Select - all inexpensive high street [UK retail chain] stores. I sent Mistress Magick some examples of what I was thinking of buying [short, flirty tea dresses, including the dress at right], and she commented on which ones she likely best and why.

On Saturday morning, I went to a shopping centre that I knew would not be busy but has a few inexpensive women’s clothes shops. As I parked the car my usual nervousness started:  Will I be seen by anybody who knows me? Will I find something suitable and will it fit?

I went into the shopping area and came to the first shop, New Look. I walked in and did my usual scan to see if I knew anyone. There were a few customers and all were ladies. There wasn’t anybody who I recognised so I started looking at the dresses on the rails. The shop was only small and, as I walked around looking at the size labels on the dresses, I wondered what the ladies were thinking. Were they picturing me in the dress I was holding, looking like a pretty sissy? I saw a couple of dresses that I liked and would have bought one of them, but they didn't have them in my size.

I left the shop and went into the next one, Peacocks. This shop was larger than the first and had more items. There were a few ladies shopping close by, but thankfully no one I recognised. I started browsing, but I didn’t see anything l liked so it was off to the third shop.

I had never heard of this shop, Interncional, so had no idea of what they sold. Once again a quick look around to see who was in the shop - it looked safe so I started looking. As I was the only man in the shop, I probably stuck out, but I kept looking at the dresses. I could not see anything like I had originally planned and discussed with Mistress Magick, but I did see a white dress with black spots and a big bow on the neck line of the dress. It looked nice and pretty, so I went over and hoped that they had my size. Luckily, they did so I picked it off the rail and went towards the tills.

Next to the till, they had some makeup items so I picked some pinkish lipstick, nail varnish and eyeliner. When choosing the makeup, I just went for pinkish colours and black for the eyeliner, but I did try to match up the lipstick and nail varnish. At this point, the lady at the till politely asked if I was okay and if wanted any help to which I replied that I was okay and placed the items on the desk. The lady smiled and scanned my items, said the amount, took my money and said goodbye. I left the shop feeling pleased with my purchases! I was going to head home but then realised that I should get mascara and eye shadow, so I went into another shop, Superdrug.

I made my way to the makeup and started looking. A couple of ladies were also looking at the displays, and I’m sure they must have wondered why a man was looking at mascara and eye shadow. There were many items and I didn't really know much about what I was looking at, so I just picked up what I thought was reasonable - black mascara and some brownish eye shadow - and went over to the till. Once again, the cashier told me the total amount and took my money. Unfortunately, it wasn’t until after I got home that I thought that maybe I should have gotten pinkish eye shadow to go with the lipstick and nail varnish.

When I got home I went into the bedroom, undressed and put on my panties that I had purchased for my previous assignment. I slipped the dress on. It seemed to fit, and I felt pleased that I had got my size right! I then found how difficult it is to fasten the zip at the back! After a bit of a struggle, I managed it.

I looked in the mirror and could see the pretty bow on the dress and my legs. The dress was above the knee and felt short, perhaps because men are usually taller than women. It felt as though the back of the dress wasn't covering my bottom and panties, so I turned around and looked over my shoulder in the mirror. It looked as though it was covering them, but not by much! I quite liked that feeling - a shameful but sexy; I can imagine a lady perhaps teasing a boy by giving him glimpses of her panties.

I was starting to feel girly and submissive because I was humiliated, in a dress and panties and now about to put on some make up. I first tried to put on eyeliner: I attempted to draw a line around the top and bottom of my eye line. It was hard as I kept on thinking I was going to poke my eye. It didn't seem very noticeable so I now tried the mascara. This didn't go to well either. Like the eyeliner, I kept on thinking I was going to poke my eye, my hand was not steady and I ended up making a mess of it. Next was the eye shadow, this time the trouble was I couldn't keep my eye lid closed, so I had to pull and hold it down with my finger and ended up with mascara on my finger. After I applied the eye shadow, it did look different but again it was not really that noticeable - perhaps a brighter colour would have been better. I then tried the lipstick. This was easier to put on. The colour was not a bright as I thought but was visible and make my lips feel softer and moist. Finally, I decided to paint both my fingers and toes with the nail varnish. Whilst easier then the eye makeup, I still found it difficult and ended up getting it on the skin around the nail. I also made the mistake of picking things up before the varnish had dried and made a mess of some of my nails.

[NOTE: I normally would have had sophie do lessons in each type of makeup and it's application, but she was so eager that I allowed her to go ahead and give things a try. I plan to give her lessons, beginning with nail polish application. I loved seeing the polish on her nails as she was writing her lines and hope she'll have private time to practice it soon.  ~M]

I felt excited now as I was doing something that ladies would do, looking at themselves in a mirror checking how they looked. So all dressed up, I went to write my lines. As I sat down in my chair, the dress would rise up so I was sitting on my panties an unusual feeling as I am only used to wearing trousers. I had to pull the dress down to cover myself. I felt shameful even though I was alone in the house because I thought if I saw a lady do this I would definitely look. Even after pulling my dress down, I still felt exposed - it would be easier in my dress to touch myself. As I leaned forward to write, I could see the bow on my dress and my painted nails.

Once I completed my lines, I remained dressed up and went to get a drink, as I drank from the glass I realised that there was a lipstick mark on the rim of the glass. When I walked the bottom of the dress slightly flapped, accentuating the feeling of an exposed bottom, and my pink toe nails looked strange, like they belonged to someone else. Every time I sat down, I would have to rearrange my dress as my panties would be exposed, tightly covering my bottom and holding my package, with lace trim around my legs and waist. It then dawned on me that ladies sit with their legs crossed so that is what I did. Once again I liked the feeling of being made to behave like a lady.

At the end of the night I went to remove my makeup and have a shower, I came to remove my dress and unzipped the back, I got aroused, as I imagined removing a ladies dress to reveal her sexy lingerie, as my dress and panties fell to the floor they each brushed my package and I was aroused and lost control of myself and could not stop myself from ejaculating, once I had finished I was disappointed with myself as part of my punishment was to suffer the no touching rule and now I had been relieved.

[I haven't yet punished sophie for cumming without permission - I think partially because I am delighted that she was so excited by everything that she simply couldn't control herself! Instead, we have worked on her control and are continuing her chastity training.]
I found this part of my punishment to be effective as it forced me to do things that ladies do, which I find embarrassing, humiliating but exciting at the same time. Finding myself worrying about my dress being too short when as a naughty boy I like ladies wearing dresses that are short, I was now getting a taste of what it is like for ladies. When it comes to shopping, I find I have two different kind of nervousness: One is being terrified of someone I know seeing me. The other is what other people who I don’t know think of a seeing a man like me shopping for ladies' things. This is mainly a worry that gives me my submissive buzz, and I kind of enjoyed it, depending on the kind of attention I was getting.

I have a lot to learn about women’s clothes and makeup, so I can look pretty and be girly for Mistress Magick.

Photos:
Select Fashion Ruffled Tea Dress: http://www.selectfashion.co.uk/clothing/s033-0402-22_blk-white.html
Internacionale: http://www.internacionale.co.uk/promotions