Lets Go Shopping

I remember it like it was yesterday, though it has been almost ten years. My first shopping trip with Mistress Kassie. We had been playing for a while on the phone and getting to know each other. Mostly just talking about scenarios of service and crossdressing. One day Mistress said it was time for me to get my first toy.

She wanted me to get a dildo to begin some anal training. So at my first opportunity I drove to an area of town where there were adult stores. I had been in a couple of them before browsing or picking up a magazine. I chose one that was not too big as I was nervous about too many people being around. Let me add that the shopping trip was not going to be just me going in. It was going to be Mistress Kassie on the phone telling the clerk why I was there and asking for some help in picking out the right toy. I was also instructed before hand to make sure I was wearing panties. When I went in there was a female clerk but no other customers. She asked if I needed help and I told her I had someone on the phone who wanted to ask her help. I handed her the phone and as the conversation progressed she began to smile very big. When Mistress was through talking to her she informed me she told the clerk I was there to buy a dildo that I would be using on myself and she agreed to help me pick one out. She also had told the clerk I was wearing panties and was to prove that to her before I could leave the store. We went into a small room where the toys were and she began picking out several. Of course I just wanted to grab the first one and get out of there, but she was getting a kick out of showing me different sizes and styles until we both decided on one. I quickly followed her to the counter and paid, but as I reached out for my package she held it away from me. She reminded me I was to show my panties to her before I could go. Thankfully no one else had come in so I quickly unbuttoned and unzipped my pants and pulled them down slightly so she could see the green thong I was wearing. She laughed hard as she handed me the bag and told me to come back anytime.

And that was just the beginning of what has become many, many shopping trips with Mistress. There have been toy stores and lingerie stores. And almost every time Mistress has talked to the clerks and told them a story. Sometimes it is that I was her boyfriend and she caught me wearing her panties and now I had to buy some of my own. Sometimes it is that she is my MIstress and I am a panty wearing slut. And when the clerk hands the phone back to me Mistress will make me say out loud thank you and that I am Mistress Kassie’s panty slut.

I have shopped at Fredericks and tried on panties, bra and stockings, which I wore out of the store under my clothes, through the mall, to my car, and checked into a hotel. I know someone there in the lobby saw the stockings below the cuff of my pants as I was not wearing socks because I saw her look down and smile.

I have shopped at Lane Bryant where I also wore panties and bra out of the store. And that was a large padded bra that was obvious under my polo shirt.

I have shopped several times at Victorias Secret, where the beautiful clerks sometimes really have fun. Once I even had to ask if I could change in their dressing room. I was allowed to and while I was in there had to call Mistress and play with my cock until I came before leaving the store.

There have been a number of other small lingerie stores or toy stores and for the most part the people have been helpful and understanding.

I am sure there will be many more opportunities like this. I would highly recommend doing a session like this with Mistress Kassie if you think you can handle the public humiliation it sometimes brings. She is the greatest!!!!

Mistress Kassie Dedicated Sissy boy!