Our First Sissy Shopping Trip

You are required to meet me at the mall coffee shop at noon. Sharp. I won’t tolerate lateness or excuses. I don’t care that this is intimidating or difficult for you. You will fetch me a 12 ounce latte from the counter along with a decaffeinated coffee for yourself. (You’re already nervous and I won’t abide any more jitters.) I will slowly sip my coffee, check my email, and generally do whatever suits me best while you wait. You’ll be getting more and more anxious, not knowing where I will take you next or what I will force you to do.

Eventually, I will finish my coffee and whisk you off to the shoe department of Nordstrom. Even though you will be dressed entirely as a man, I will take you to the women’s section and flag down a sales woman. You will have to remove your shoes and step on the cold, metal, Brannock device. She’ll measure each foot (dragging it out with a knowing look at me), because people’s feet aren’t always the same size. You’ll have to remove your socks and put on little nylon footies. I’ll point to a pair of shiny black pumps with 3 inch heels. She will go to the back and get them in your (larger than the average woman’s) size. You will have to roll up your pants and walk back and forth in front of us. Her hand will go over her mouth to hide her smile and stifle her giggle, but if you could lift your head from the shame, you would see the laughter in her eyes. Your boy shoes will go into the box and you’ll have to wear your new pumps. Her smirk will last all the way through your purchase as she runs your credit card through the reader. 

Next I’ll lead you on a search for the perfect little black dress (a staple in every woman’s wardrobe). My fingers will run through the racks of dresses until they come to rest on just the right one, sized up for your physique. Your shame will grow even further as I hold it against your body to judge the look and possible fit. You’ll feel the eyes of other customers on you while we shop. I’ll send you to the dressing room and you’ll have to face the woman at the front handing you a tag with a “1” on it and unlock the door of your stall. Her eyebrows will rise and she will choke back her laughter. I’ll stand near the entrance and yell back that you have to come out and model the dress for me. You will have to walk with one foot in front of the other, swaying your hips and holding one hand out to look as feminine as possible. 

“Your underwear is showing through and ruining the lines.” After purchasing the dress we’ll proceed to the lingerie department in your pumps and boy clothes. First I will grab a pair of sheer, black stockings with a seam up the back. Then I’ll finger my way through the bins and hangers, picking up various pairs of panties and holding them up against your hips. “Hmmm…no. Yes. Maybe…” Finally I will settle on 3 pairs. No reputable store allows you to try on panties, but there will be no doubt who these are for as you buy them. The woman ringing you up will draw the process out as long as possible as a line forms behind us, offering you a store credit card, explaining the discount you’ll receive today if you only sign up. I will smile slyly at you the entire time, letting you soak in mortification. 

Finally, we will finish your purchase. After we buy makeup and a wig, you’ll have everything you need to dress up for a night on the town. Everyone will stare at you. Won’t that be fun?

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