Today is my first post of "experiences of the past". In the last two years with my female friend as my dominant keyholder, I had a lot of exciting, crazy, funny and embarrasing moments. One of them was a very special shopping tour I was sent to. To be exact there were two shopping tours. This post ist about the first one. Also I want to say that I'm really thankful for her enabling this experience.
I hope you will be as excited reading it as I was back then doing it
The evening before
Before everything startet I received clear instructions what I had to to the next morning. I didn't know exactly what would happen and how the whole thing would be. I only knew that I had to take the bus and train in the morning and drive to the next big city to a big shopping mall. Additionally I knew that this would be a special shopping tour for my inner female desires :)
Waking up to a special day
I was very excited and didn't sleep well but I was ready. So I packed everything I needed, a backpack and money, and drove to the shopping mall. In the meantime I got more information via WhatsApp. She said that after arriving I would get the first of five task I had to to. If I did a good job I would get her permission for a full orgasm. I didn't have a orgasm in over 10 days (don't know the exact time), so I was very motivated to do a good job. I had to take photos of every task as a proof. Photos I will post here too. One photo I already used in my introduction post 2 days ago.
The first task - pretty lips
The first task was easy in comparison to the other task but still very exciting and challenging for me. I didn't have any experience like this before.
Visit a store with a lot of make-up. I want you to buy a lipstick you like. But don't just take one lipstick. I want you to test multiple ones on your hand. Feel like a real woman and take your time.
At the first moment I thought something like: "Omg that's exciting am I really gonna do that? I think that's a task I can manage to do." With that thought I went into the store. Luckily it was still early and not many people were there. A few women here and there. I waited until I was alone and undisturbed at the lipstick shelve. I tried a few ones on my hand, but had my favorite right a way. A nice purple one. My heart was racing so I made it fast. While testing I was always looking right and left for no one to see me. It felt akward buying just one lipstick and asked myself what the cashier might think of me. But it could be just a present for my girlfriend, couldn't it?
That was my proof for the first task :)
The second task - something sexy
The first task was exciting and perfect for the beginning. BUT the second task was waaaaay harder. The first moment reading the task I felt like being thrown in cold water. I was really nervous "Am I really gonna do THAT?" and at the same time I was getting aroused.
For the next task you have to visit a store with sexy lingerie for women. Your task is to look for one or multiple bras and panties that you like the most. But just by looking at them you won't see if it matches your body. I want you to take a few sets and go into a fitting room to try them on. Take what you like and buy it.
I read that right and knew I had to do it. I WANTED to do it. And I wanted to make her "proud" doing her task. So I looked for the store and found it. A lot of people were there. Mostly women and when there were men, they were there with their girlfriend. It seemed I was the only solo guy there. I started to look for lingerie I like and fits me always with other persons only a few meters away from me. I felt observed. I felt the heat in my head. The only thing that gave me courage was the thought: "It could be some guy buying lingerie for his girlfriend." If they only knew...
I had problems finding a fitting bra for myself. They were all looking really hot but I needed a small cup with a good girth. None of them were perfect so I started to take a few ones with B and C cup, because obviously girth was the most important thing. Some bras came with matching panties. For some others I choose single panties I liked. Ok... now I had my hands full of lingerie, always trying to hide them, but I was at a point I knew that I couldn't hide it. Now I had only one target. Going into a fitting room as fast as possible without anyone noticing it. That was the second most difficult thing with this task, because there were so MANY women standing in front of the fitting room helping their friends finding the perfect lingerie. I had to wait for the perfect moment, so I was walking around in the store for a few minutes what felt like eternity.
One moment there was only one woman standing in front of the fitting rooms and she seemed to be distracted, so I took my chance and went into one cabin. I felt secure, nobody can see me, all the glances I felt on me before were gone. Time for catching some breath. I knew it wasn't over but first came the calm part. Me trying on different bras and panties and looking in the mirror. I liked what I saw. Trying on panties wasn't perfect because of course I had to try it on over my boxershorts.
Picture in lingerie (NSFW)
Trying on some sexy lingerie :) I bought both as they were push up bras and I liked them.
The most difficult part for this task was about to come - going out of the cabin, alone, definitely looking like a guy and with a hand full of women's lingerie. There was only one way to do this: Fast out and ignoring everything around me :D
That's exactly how I did it. I can't remember if there were other women standing next to me. I just had one target: The checkout. The rest was easy - going to the checkout and paying for my lingerie.
Now I was proud owner of lingerie that I bought myself :)
The third task - something with class
Now that you have the perfect underwear you need something on top of it. I want you to buy a nice dress. Something with class and not looking slutty. Take a few dresses you like and try them on in the fitting room. Buy one of them. Optional: Go out of the cabin with a dress and look into the big mirror.
The store I had to go to has always an extra big mirror outside of the cabins in the fitting room. Luckily it was optional. I was sure I couldn't do this part. Dressed in a dress and showing myself to others? I wasn't ready for that yet.
The main part of the task seemed relatively easy to me after doing task 2. But one thing made it very difficult. Ok I was searching for good looking dresses that fit me. I already had a few. Other women around me didn't bother me that much anymore. As I wanted to go into the fitting room I realized that it was a separated room with a employee waiting at the front. I thought "Ok let's wait until she is away." I was wandering around in the store waiting for a chance but she didn't go away. I was looking for more dresses although I already had everything. I began to sweat as it was hot in the store. It really took about 45 minutes until I had enough courage to just go in, ignore the woman and go into a cabin.
The rest is the same like it task 2. I tried on my dresses. I wasn't perfectly pleased with all of them but there were no more dresses so I took the best one for me at that moment.
I took dress number 4. Was it the best decision?
Going out of the cabin was like in task number 2 - VERY FAST! Buying was again easy.
Task 4 - every woman needs it
The fourth part was buying shoes. Shoes with heels.
For your perfect outfit you also need a pair of high heels. So I want you to look for ones that you like and matches your dress.
Buying high heels was a task I thought would be difficult, as there are no cabins to try them on. But at the same time that was my advantage. I was easily able to take them, walk to a part of the store where no one was and try them on. But first I was searching for high heels in my size (about 44). To my disappointment there wasn't a single one in my size. The biggest size was 42. Woman have small feet :( Ok no suprise but I was hoping for at least one pair in my size. I wanted to do the task so I took one pair with the biggest size. They were at the same time the ones I liked the most. They looked really awesome and I really wished the fit me, even if there wasn't a chance.
Trying them on resulted in not getting my feet in :(
I think these high heels are really beautiful. So sad they weren't made for me.
An alternative task 4
I was reporting that there weren't any shoes for me. So she decided to do an alternative task instead. It was easier than the tasks before. I just had to buy some jewelry for myself. I walked into a small store where you could only buy jewelry. It was a bit strange again to be alone as a men with only woman but I was getting better getting along with these situations. I looked around what I could like and choose a necklace and a bracelett.
You can see the jewelry further down in my post.
Task 5 - a big suprise
Happy about doing 4 out of 5 tasks so far I was excited what the last task would be about.
Good Job! Your shopping tour is FINISHED. You can drive home now. I will talk to you at the evening about your tasks. You might wonder what's up with task 5. You will also see what the last task is about later.
Ok that was a suprise. I thought the last task is also at the shopping mall. I was excited. What would the last task be? I took my buying bags and drove home. I thought a lot about my shopping tour and was proud that I did it. It wasn't easy for me but really exciting, arousing and kind of humiliating. The kind i really like :)
The walk of insight
For the evening my keyholder and creator of my special shopping tour wanted to take a walk with me so we could call each other undisturbed. (we live a few 100 km apart from each other)
She told me that she was really satisfied with my performance doing all task like she demanded. Expect the one optional part in task 2. But that was ok. So it was time to tell me the last part.
Now you have all these sexy clothes but nobody can see it. I want you to make an Instagram account specifically for you as Cassy. We will use it often in the future. For now your task is to make some sexy pictures of you in your new clothes and lingerie.
That was something I really didn't expect but the idea really fascinated me. After the walk I prepared everything and tried to make some sexy photos. It felt good to know that I will show my picture to the public not knowing who would see them.
Picture in lingerie (NSFW)
A few pictures I posted on Instagram.
That was it for the SPECIAL shopping tour. It was a crazy experience for me and I am really happy that I had the possibility to do it. I hope you liked it. I will post every week about something in the past I experienced. For example a year later there was another shopping tour even more crazy!