Luggage Lost Sissy Found

Dear Diary,

It’s November 2nd and this is your Princess Molly (haha you wish I was yours)!  Cassidy and I are in one of my favorite places. We arrived last night only to discover that our luggage was lagging behind. Luckily, Cassidy had reminded me to pack a set of shorts and a tank as well as some panties into my carry-on, along with my laptop. But still….we had no other clothes for the foreseeable future so you know what that means, don’t you? We went shopping!

We decided that since shopping takes so much energy that we would grab some breakfast and try to find the nearest mall. As luck would have it our waiter was a cute sissy with the best southern accent. This girlie gurl had no problem telling us all the best places to go and what would look the best on us.  Cassidy and I had so much fun talking that we invited the sissy waiter to come with us on our shopping trip. So we sat, drank coffee and chatted for the hour it took for the breakfast shift to be over and off we went with our newest girly friend in tow!

Dress Her Up, I’ll Take Her

Now as all of you know, we love to dress up sissies! We had a plan to really go over the top with our sissy and throw in just a little sissy humiliation to be naughty! You know we just can’t be totally nice. It would ruin our reputation, Diary!

We started our teasing tour in a coastal town that has a large shopping mall. Cassidy and I decided our excursion would begin at one of the big anchor stores at one end of the mall and we would work our way down to the smaller boutique like shops. By the time we entered the department store, we had talked to our sissy friend and come up with  a fun plan that would work. The sissy was literally shaking with excitement.  He was tall and kinda pretty and used to passing in most situations. The three of us walked around the store, looking for the best clothes for her to walk the mall in with us. Cassidy found this gorgeous blue dress and then I discovered the greatest peep toed shoes to go with it. We bought all the necessary stuff to make it an entire outfit, had her try it all on and then paid for all of the items.

Our Day with a  Slutty Sissy

We needed him to get into these great clothes so a quick stop and sneaking into the ladies room was in order.  After she was totally dressed to the nines and stowing the old clothes in the shopping bags, we went to crawl the mall. We had so much fun buying new clothes. We both got new bikinis in complementary colors of course, each of us got a black one and then I picked a white one too and Cass found a sexy red one. Our friend the sissy had a blast too, until we passed a mirror and Cassidy pointed and laughed at her reflection, I looked and giggled too.  It’s not that there was anything really wrong with the way she looked, except that she wasn’t a she!  She was a he all dressed up in a dress and heels!

After some pointing and our sissy blushing wildly, we stopped a couple of guys and asked them if they were up for some fun!  The sissy was only a little upset with our laughter, mostly he enjoyed it and meeting the guys really made him happy!   Especially when they sat at the nearest coffee shop with us and told us they were up for anything.  So, was our slutty sissy and we happily kept watch, giggling the whole time while sissy sucked some cock and showed off her new panties in the bathroom!

I’m not sure what happened after that, because the hotel called us to say that the airline had delivered our bags.  We were thrilled and thought nothing of leaving the sissy and her new friends there in the bathroom having all kinds of fun!  We’ll have to watch the news tonight and see if they got caught!

Well, Diary, it’s late and I’m tired and as they say, “Tomorrow is another day…” of teasing, that is.