New adventure

I left here wearing pink bra, breast forms, pink stockings, black garter belt, pink ruffled sissy panties, two sissy anklets, corset, Barbie watch, 3 sissy bracelets, a man's shirt tucked into the panties, and khakis with black flats.

My first stop was McDonalds where I ordered a sandwich and drink and then sat at table where I had to put on my pink leather dog collar with 3 sissy hearts and long press-on nails with pink tips. Fortunately no one seemed to notice.

Next stop was Lane Bryant at South County mall. The clerk remembered me and said that you have not been here in a while. I told her that mistress had not sent me recently. She just smiled. I told her I needed a new short dress or skirt and it could not be any longer than knee length. She could only find one to try and it ended up being to small and too long. I then when out to the car where I had to change into the short dress I bought a couple of month ago at Dots. I it barely covers the stocking tops. I stopped at For Lovers Only, an adult lingerie and novelty store, and had to purchase my first butt plug. I bought a medium size butt plug that was 5 inches long and 1.75 inches in diameter at its widest point and put it in my pink clutch purse that I was carrying.

The next stop was the Dots store that I have had to go to the last couple of times. I had to get a dress or skirt. Mistress was still angry that I did not come home with a dress when she sent me 10 days ago. The lining of the only short plus size dress they had then was several inches shorter than the thin dress and my stocking tops and garters were very obvious. When I got home, she said she did not care. This time I knew I had better come home with something whether it was appropriate or not. I looked at the clearance plus size garments and did not find the dress anymore. All three clerks offered to help me. Two of them started looking for dresses that were knee length or less. They found two possible dresses. I went to try them on. When I first entered the dressing room, I took my dress off, pulled my panties down and had to sit on the butt plug to insert it into my sissy pussy. It was the first time anything but the tampons I wear during my monthly period had been in my sissy pussy. It was very uncomfortable. I pulled the sissy panties up and tried on the two dresses. One, a white one, looked awful on me but the flowery one did not look too bad and was clearly above the knees but if I was careful covered the stocking tops. The lining if pulled down properly was only a couple of inches from the bottom of the dress. The garters and stocking tops although noticeable if one was looking did not stand out like in the dress I did not buy last time.

I came out of the dressing room wearing the flowery dress and walking a little different due to the butt plug in my sissy pussy. I asked the clerk if I could pay for and wear the dress out of the store. She got a pair of scissors and cut off the tag and left it on the counter for the other clerk. The other clerk was checking out another customer, a very attractive blonde woman. She helped her and asked her to sample several perfumes. It took several minutes and the blonde kept looking my way and smiled. Finally she finished with that sale and started on mine. She said, I don’t suppose you want to sample the perfumes, do you?” I told her not this time. As I was paying for the dress the clerk said, “That pink necklace matches your dress.” I thanked her and told her that mistress says I have to always wear it when I am out so that everyone knows my status.

I then went next door to Payless Shoes where they have been very nice before. A clerk who helped me last time came over and welcomed me and asked to help. She looked at my heels and said that they were her favorite shoes. I told her that they were mine also and that I had bought them there a year ago. She pointed out the 11W and 12W shoes and left me to look around. The other two younger clerks, in their 20s, came by and offered to help. They both seemed to stare but were very helpful. One spent some time admiring my collar and asked about the tags. I told her that mistress got them for me. She said it was very nice. She had me sit as she tried two pairs of shoes on me. She noticed and commented on the lacy tops of my pink stockings. It was uncomfortable sitting on the hard stool with the butt plug in place. Unfortunately, they did not having any pink shoes which is what mistress wants me to get. She did offer that they received shipments on Tuesday and Thursdays and that I should come back and check in.

Shopping Trip

Mistress sent me out on another shopping adventure again last Thursday. I was wearing the usual pink ruffled sissy, black garter belt, black stockings, sissy anklets, corset, pink bra, and breastforms. I wore Mary Jane’s with 3 inch heels, thin white crop pants, pink peasant top, pink dog collar with sissy dog tags, pink press-on nails, and a pink Barbie watch. You can easily see the pink panties and black garter belt and stockings thru the top and pants.

I was sent to a Dot’s store in Maplewood. It was the first time I had been there. Mistress had been in and had seen a thin frilly pink top and a couple of flowery short dresses that she wanted me to buy.

The two clerks were not very friendly. They seemed to ignore me but offered to help others. When I asked for help with finding a size they did help and when I had pick out 2 dresses and the pink top to try on, one of the did become helpful. She led me to the dressing room and after she opened the dressing room door, she looked closely at my neck and asked what the necklace said. I had to explain that it was a dog collar that mistress made me wear and that the tags said, “Owned by Diane”, “Diane’s Sissy”, and “Wendesis”. I told her that was my name. She just responded “Oh.” The top fit fine but the dresses, although very cute, were two sizes smaller than I usually wear and as a result too short. They did not cover my stocking tops at all. I purchased the top and asked if I could change into it to wear. I put it back on and the clerk help remove the tags for me. I left the store and went to the car where I removed the pants and put on a short black skirt. Here are pictures of the new sissy top and my stocking top and pink nails.



I then drove thru McDonalds with my skirt pulled up and purchased a soda.

It was then across the river to the Hustler Club. I went into Boutique/Video Arcade and bought a wristband to go into the arcade to watch videos in the booths. I walked around for a few minutes before I walked into a booth. Mistress had told me to leave the door ajar for at least ten seconds before I closed it. I watched a shemale video and then left the booth to walk around again. There were about 10 men wandering around but thankfully none seemed interested in me. After watching another video, I left and drove to Wiseguys Gentlemens Club.

When I walked in there seemed to be more dancers than men. Several of the ladies said hi to me and Autumn came rushing over and gave me a big hug and kiss. She said she had had a bad day and seeing me really cheered her up. We went to the bar and bought me a Shirley Temple and she got a shot. We then went and at a table and talked, held hands and rubbed legs. She is always so nice to me. At 1:30, I had to excuse myself and tell her that it was time for me to change my tampon. It had been four hours and I am not allowed to miss by more than 10 minutes. I went into the men’s room and changed my tampon and returned to Autumn. She suggested a private dance. I asked how much and she said $30. I only had $25 left and she said she would do it for me. We went into the backroom and she gave me a private although she never really touched my crotch and I did leave very unsatisfied. Next time I am sent there, I will tell her that if she is not going to help me cum, then I would rather tip her to just sit and talk for a long time rather than have a one song private with little stimulation.

When I returned home, Mistress Diane, Alicia, and Cindy were there. I do to describe in detail the entire trip while I was masturbating for them. After I came I had to clean up the mess with my tongue while continuing to stroke for 20 more minutes. They just laughed at my futile efforts to get my "little sissy clit" hard again.