It’s been a few years now, to be exact my first Sissy shopping experience was in 2017. For me, it was extremely exciting because not only did I have to just buy women’s clothes, but I was also lightly dressed as a Sissy in the process. That was very embarrassing at the time and correspondingly exciting. I received the exact instructions live from my boss. I’d like to tell you exactly how that went down in this post.
My outfit as Sissy
It wasn’t a full Sissy outfit, as it was also my first time alone on a Sissy shopping trip in a large well-attended mall. But maybe that made it even more embarrassing, since I was clearly supposed to be a male with some “weird” adornments on.
What did I have to wear? Under my T-shirt I had a large push-up bra on, which clearly stood out. My lips were made up with a light lipstick. The worst part of the whole thing was my big red round clip earrings and my red pearl necklace that I was supposed to wear. On my wrist I wore a red bracelet.
That was it. I looked striking. Too striking for a low heartbeat.
Tasks from my boss
I had already received the instructions on what to wear and how to get started a few days before the start. How the Sissy shopping tour itself should proceed was unknown to me. I was to receive one task after completing the previous task.
I did not arrive in this Sissy outfit but had everything in a backpack. In the men’s restroom at the mall, I prepared and got ready.
I can say that I was so incredibly excited at that time. There was a cleaning lady at the entrance with her money basket. She had seen me go in and would see me go out looking different.
So the whole thing took over 20 minutes before I dared to come out with my pearl necklace and earrings. The cleaning lady was still in the same place, but I didn’t look at her anymore and just wanted to get out quickly.
But now I was standing in the middle of the mall with a lot of strange people.
Buying lipstick from an amused saleswoman
The first task was relatively simple. I should choose and buy a nice lipstick. Not far away was also the perfect store for this. It was still early and overall not that busy. There were two female sales assistants in this store and no other customers. I still tried to hide from them as long as possible, at least my jewelry and bulge of the T-shirt. However, I had to go to the checkout at some point after I found a good lipstick. So I gathered my courage and thought to myself, I have to do it anyway, there’s no point in playing hide and seek here forever now.
I don’t know exactly what the young saleswoman was thinking when I approached her, but I could definitely tell she was smirking, but remained professional. Oh man, that was embarrassing, I wanted to complete the payment process as quickly as possible and get out without letting my perceived embarrassment show.
In hindsight, I find the reaction of the saleswoman exciting.
I was already warmed up a bit now and had grown into the situation. The excitement was still enormously high, but I could control it better. My next task should then be to buy myself beautiful jewelry. Whether necklace, rings, bracelet or earrings. These jewelry stores are always relatively small. I felt so incredibly watched. Permanent.
I couldn’t get a clear head at all, but still tried to concentrate and find suitable jewelry for me as Sissy rather quickly than slowly.
I managed to do that quickly and the checkout process with a middle-aged lady was also completely professional. She didn’t take any notice of my appearance, which gave me confidence for my further Sissy shopping adventure.
Buying clothes for a Sissy
Now the tension increased because it became more demanding. With my gained self-confidence, I dared to tackle the task. In a big clothing store I was supposed to buy some nice clothes. I remember very well how I looked for clothes in the store for ages and just couldn’t get up the courage to go into the changing rooms with them. Again and again, the fear was too strong and I made another round on the fake search for more dresses, although I actually already held everything I needed in my hand. There were several varieties of possible Sissy dresses. I didn’t find them all particularly good, but suitable. But I was not allowed to buy them without trying them on, that was part of the task.
Sometime after what felt like half an hour I took enough courage and went into the changing rooms at the fastest pace, past the lady who was keeping an eye on things there.
Phew… I had made it and was now at least somewhat protected behind a curtain. My pulse could go down a little bit. Now I tried on my dresses and took pictures as proof of all tasks.
I chose the dress on the bottom right (I know, a terrible choice) and left the others in the dressing room. As quickly and quietly as I could, I got out of the dressing room and went to the checkout quickly this time.
The whole thing was quite exhausting, because the pulse was permanently high. The payment went without any particular incident and so this task was also completed.
Now it was time for a lunch break and I had earned it. Meanwhile, there were several bags in my luggage with nice Sissy yield. I had already gotten used to my own embarrassing appearance, but mentally it was still a constant companion of my excitement.
Even lunch was a small task. I was supposed to buy something delicious and then consume it with relish. I had no way of hiding myself. To make it easier for myself, I just always tried not to notice people around me.
For dinner I had a stuffed burrito with salmon.
Buying lingerie with a special experience
After that something special was supposed to happen. The task was that I buy ladies lingerie. Beautiful bras, panties and pantyhose or just what else hot stuff there is. At one point I was supposed to look at myself in the big mirror outside the dressing rooms while wearing something revealing.
Buying Sissy lingerie itself was a challenging task. I looked around the store and what can I say. It was a dream, I felt comfortable. All this beautiful lingerie for women that I would love to wear myself.
But after a short time something unbelievable happened. One of the saleswomen approached me. She asked me what I was looking for. I had not expected that. My heart was beating so fast, but I didn’t let it show. I knew this was the moment when I might get some counseling. I told her the truth, at least part of it. I told her, that I was looking for bras but do not really know what size I need.
The advice in the lingerie store
The saleswoman was middle aged, helpful and friendly. Really professional, although she would have a funny story to tell tonight about someone who wanted to buy ladies lingerie and wore flashy earrings and a pearl necklace.
The advice of the lady went so far that she brought me possible bras in the changing room. I could not believe what was actually happening at that moment. I was standing in the dressing room waiting for bras. While the lady was away, I quickly took photos as proof.
When I was all done, I even picked out some pantyhose. I just felt very comfortable, as comfortable as one could feel in this situation.
I had not fulfilled the set task 100%, because I had not looked at myself in the large mirror. But there was also no mirror. But the experience with the consultation was enough for my boss to let that count as well.
Searching for high heels
Now I was equipped with almost everything and I was already longing a little for the end. That was enough excitement for at least a week. But it was not over yet. I should look for high heels. It was clear that it would be difficult to find such shoes in my size (11 male). Therefore, it would also be enough for me to try on the largest possible..
So I went to my last adventure of the Sissy shopping tour. There were unfortunately as expected not many high heels and the largest were just size 43. From the looks of it, they looked great, exactly what I wanted. So I took them and looked for a place as unobserved as possible to try on the heels. Quickly I shot evidence pictures and hid the shoes. I did not dare to put them back where I had them from.
The relief came and the tension fell off me. I was happy, left the store and also as soon as possible the mall. In a suitable place, I immediately took off all my jewelry and also removed my bra from under my T-shirtI quickly wiped off the lipstick and all the tension went away.
My boss was extremely pleased with my Sissy shopping trip because I had done everything well and the tasks had worked well. The experience with the consultation was again something very special and unexpected.
You want to experience the same?
You can also experience this quite easily by simply trying to complete the tasks in exactly the same way as I did back then. Maybe something unexpected will happen during your personal Sissy shopping tour? Here are all the tasks for you to do step by step.
Pack a backpack with a lipstick, push-up bra, earrings, necklace and bracelet. Go to a mall and put on everything from your backpack in the restroom.
First task: Try several lipsticks on the backside of your hand and then pick the most beautiful one. Buy it.
Second task: Go to a jewelry store and buy at least one piece of jewelry for yourself as Sissy.
Third task: Get yourself a nice little dress. To do this, you choose several dresses that you like and could fit. Then you try on each dress in the dressing room and buy at least the most beautiful of them.
Fourth task: Lunch break! Find something tasty and eat it where other people can see you.
Fifth task: Go to a store for sexy lingerie. There you buy a nice set, consisting of bra and panties. You are welcome to buy more. Really let off steam. A Sissy feels most comfortable with lingerie. You should try on the sets in the changing room before you buy them. Let yourself be advised by a saleswoman, if they appeal to you.
Sixth task: Get yourself some high heels. If you can’t find any in your size, you have to at least try some on.