Sissy Shopping

Lately my Master demanded a brave proof for my intent to become more sissificated which led us to a city about one and a half hour away from home. It’s a big city, so it’s easy to vanish into thin air among all these folks there, and I was glad John had taken me there and not insisted I should do it in our rather small hometown. The night before he had given me a note on which he had written all the things he wanted me to buy. It said

  1. 1 white bra with lace, convenient size, modest looks
  2. 1 coloured bra with lace, tight-fitting, slutty looks
  3. 1 white panty with lace, convenient size, modest looks
  4. 1 coloured panty with lace, tight-fitting, slutty look
  5. 1 belt, black
  6. 2 pairs of nylons, black
  7. 1 vest, white, modest looks
  8. 1 underskirt, white, modest looks
  9. 1 blouse with lace, white, modest looks
  10. 1 skirt, black, modest looks
  11. 1 blouse, slutty looks
  12. 1 skirt, slutty looks
  13. 1 ball gown, must be very girlish
  14. mascara, lipgloss, eyeshade and rouge in decent colours
  15. lipstick, eyeshade and rouge in slutty colours
  16. 1 package of sanitary towels, normal
  17. 1 package of sanitary towels, incontinence
  18. 1 package of tampons
  19. 1 can of Vaseline

I guess John added item 19 to make it a bit more annoying for me at the cash desk.

The night before our trip I could hardly get to sleep. I was very nervous and kept asking myself how I would perform. We had talked this trip over and over again and we both thought it a good idea to make buying these things a bit of a challenge, besides trying clothes on is always better than just ordering them online. But anyway, I was very excited and nervous. It’s one thing pretending you’re buying a bra for your non-existent girlfriend or having to try things on!

To be honest, my experiences with bras and other women’s underwear are scarce. I have lived together with two women and sometimes I hung up their freshly washed clothes and of course I’ve seen underwear on women, but I have never really tried to open or close a bra, not to speak of any experiences concerning finding out which size I needed.

John had promised me to stay somewhere in the near, but he denied to help me, which made it a bit more embarassing. When I stood in front of all these undies, I did not know which size to choose, so I began with choosing a design. I had the list handy and went it through systematically, always picking what seemed to be the biggest size. For a man, I’m quite slender, but for a woman I guess I’m broad. They had no belt at all, only some corsages with attached suspenders, but they all seemed to be too small. I managed to flit over to the blouses and skirts unmolested, but when I was pondering about the question whether a see-through-blouse would fit Master’s idea of a slutty blouse, I was hit by the shop assistant. I had hoped I could’ve avoided that.

I had thought about how I should best respond to a shop assistant before and had come to the conclusion that telling a lie about my fictional girlfriend would not work out, as I had to try the clothes on. So I had decided to be honest. I told her it was my first time shopping from the women’s department and that I did not know my size. You could tell by the looks in her eyes that she was bewildered, but I guess in a big city people are used to not bother too much about other people’s concerns, at least I hope so. She reacted very professionally for which I was thankful. First, she took me back to the undies and wrapped a measuring tape around my chest. It turned out that I’m at 99 cm. She told me to try bras in size 95 with cups A for small breasts. She said there were even AA cups for very small breasts but obviously not at size 95. She also took others measures to find out which size I’d need for blouses and trousers or skirts. I wanted to thank her and make my way through the department, but obviously she had decided that I needed her help.

I did not know whether to be glad or embarrased, but it turned out she was really helpful. I tried not to let her look at my list, but when she finally did, it turned out she did not speak English. What a relief, as this meant she wouldn’t get to know about the make-up and other things. It was very hard for me to stay calm and serious. I was very excited and could feel the looks of others burning on my skin. I whished Love would have been there with me and it gave me a hard time knowing that he was watching me and pretending not accompanying me.

It did not take too long until I had picked hopefully fitting undies. The assistant suggested I should try them on first before moving over to the other clothes, so I did. When I was in the changing cubicle, I saw how red my face had gotten. First of all I sat down and tried to calm down a bit by focussing on my breath. When I sat there, I thought how odd I felt. I really wanted to be there and I had to admit that I was turned on by the thought of shortly putting on women’s underwear, but simultaneously I felt ashamed and insecure. What a well-known feeling that is.

I undressed and took the first bra of my life. The assistant had advised me how to put it on and I did as she told me. It fitted, although I thought I should find something to stuff it with. The look at myself bewildered me. It was strange and abasing, but nonetheless I felt gorgeous and in a way beautiful and glamourous. I liked it. When I had tried on all the bras and panties and vests, there was still a belt missing, because the corsage did not fit me. I changed again. The shop assistant was waiting for me and I told her that the corsage had not been of my size. She replied that there was another shop in town which might offer what I was looking for.

We went over to the clothes and again she was very helpful, although it was very hard for me to insist wanting to try clothes that looked slutty. She seemed to think of me as a lady LOL During our conversation I saw she realized the ring on my finger and asked myself what she would think of me? A married man who lives out his fantasies without his wife? 🙂 They had a lot of skirts and blouses there which fitted my list, but it was a bit hard to find a gown. Most of them looked ways to noble, more like a wedding dress than an over-girlish ball gown. I guess it would have been easier when we lived in the 80ies! At least the assistant had the idea of looking among the costumes for carnival, but as these were in another department, she sent me to try the skirts and blouses on first.

It turned out my shoulders are a bit too broad for most blouses of my actual women’s size, so that she brought them again one size bigger. Trying the clothes on was not easy. I had a stiffy and was very aroused and I thought she could see it. Women’s clothes are very smooth. Great chance I ruin them within a week 😦 When I had picked the things Master wanted me to buy, I added another skirt and another blouse, just because.

The assistant accompanied me to the carnivals section and they really had a very girlish princess-costume there. It’s pink with ribbons and lace. When I put it on…well, I guess I should not have done, but it just needed some strokes to have me there. When I had clamed down and changed, she took me to the cash desk and we said goodbye and I thanked her for the help. She said, now that I know my sizes, buying clothes the next time will be easier. Yeah, I guess. The looks of the customers around me were embarassing, but when I finally had three bags handed over to me, I thought I could be proud of me.

When I left the shop, Love was waiting in front of it. He smiled and waved a small bag. “I have added a bit on to it. Thought you might like it”. He had bought the corsage which was too small for me and, for God’s sake, a crown made of gold wire and rhinestones. Ugh! He kissed me and I could tell he was very aroused, too. We decided to look for the belt in the other store and they had one which fitted me, although their shop assistant was not as helpful and kind. We had something for lunch and then Love advised me to buy the other things from my list. But buying make-up is not such an effort and I did not need help with it. To be honest, buying tampons and Vaseline at the same time feels ways more uncomfortable than buying a princess-costume.

When we came home, Master wanted me to show what I bought and I made a little fashion show for him, although we did not come very far. I don’t know why but wearing women’s undies is really hot! Now I’m thinking about getting me a pair of shoes, but I guess I’ll have to order them because of my size.


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