Sissy’s Night at the Department Store


My Mistress called me today and told me to pack a bag because we were going on a little trip. I was so excited! I literally danced around my apartment as I packed my things in a small overnight bag. She told me to bring all my makeup and girly things so I can only imagine where we’re going! I made sure that I was ready and dressed in all my sissy boy splendor when she can to pick me up that evening. We were going to have a Sissy’s Night Out!


Surprise From My Mistress


I’ve known my Mistress for many years. I love her totally because she had helped me embrace my sissy side completely and happily celebrate who I really am. So, there I stand waiting to get in her car in my black heels and black mini skirt. Paired with that, I have chosen a pretty sky-blue silk top; I really love going out dressed as a sissy. My makeup skills rivaled those of a professional makeup artist. My attitude is if this is gonna be me, then I’m going to look my best doing it. I like who I have become over the years.


My Mistress arrives to take me on our journey. She is a petite blond bombshell with a perfect spray tan and a body that can attest to many hours in the gym. She smiles a secret smile when I ask her what we’re doing. I can’t hide my surprise when she pulls into the parking lot of a large department store that anchors in the local mall. I look at the small Cartier watch on my wrist and see that it is almost closing time. The parking lot we’re in is nearly deserted. I raise a perfectly arched eyebrow at my Mistress but follow her into the store anyway.


Arrival at the Store


There is a well-dressed woman waiting on us at the door. She introduces herself and ushers us to a secluded corner. She smiles at me warmly and wishes me good luck on my night. What is going on? Again, I look at my Mistress quizzically. She has a huge smile when she tells me that we are going to spend the night in the store and that I can try on anything in the place! I almost swoon at the thought of all these beautiful things for me to do and try. It was going to be a great night! I clap wildly and hug my Mistress. She explains that we have to wait until everyone has left the store before we can wander about by ourselves. So, we follow the store employee who met us at the door to the back where we are left in a small break room. No one questions our presence here. My Mistress has cleverly thought to bring enough food for both of us, so we eat while we wait.


Finally, all is quiet. The woman comes back to the room and says that she’s leaving, and she will lock us in for the night. We are finally free to roam, and try on everything! It’s a crossdressers delight.


Just Like A Woman


So, I find myself in the middle of the store, unsure of where to start. My Mistress suggests that I start with shoes and work my way up. I agree and head for the shoe department. I find two pairs of beautiful shoes with peep toes and wedge heels. After I’ve carefully tried them on and found my size in the back, I stack the boxes on the floor in the middle of the store. This way, I can have everything in order so I can purchase it all first thing in the morning. My credit card’s going to be screaming by the end of it, but I’m worth it, right? This is a once in a lifetime opportunity. So off to the woman’s clothing section I go.


The evening becomes a blur of activity after that. I look at everything and then decide what I should try on. My Mistress follows me around, giving me suggestions and telling me I’m beautiful whenever I try something new. I settle on four new outfits complete with panties, bras and panty hose to go with each set. I get several purses, belts and scarves, as well as several pairs of tights for the winter. I find a red wool pea coat that I must have and leather gloves.


Me and the Make Up Counter


Finally, I arrive at the makeup counter. I’m so excited that I can stand and try on makeup like any other woman that I feel lightheaded. I actually get to pick out the shade of foundation and eye shadow. I choose mascara and moisturizer and blush.


I’m exhausted by the time I’m done at three AM. It was a great night. Now all I could do was go to the furniture section and lie down. Tomorrow I would be able to take it all home and try it on all over again!


Do You Dream Of A Sissy’s Night Out Of Your Own? Call The Sissy Training Mistresses 800.730.3507