I could see him trembling slightly as I got into his car … he looked so sweet, so nervous, afraid to look me straight in the eye. I slip into the passenger seat and smiled warmly at him and knew that this was going to be fun. He wanted to go shopping for sexy lingerie and other than tormenting and teasing sweet submissives, shopping with sweet little cross dressing panty boys was right up there with my favorite pastimes .

“Hello Stephanie, are you ready to go shopping dear?” He stutters ever so slightly, “Yes, Mistress. Thank you.” “Good but I want there to be no mistake that you are my slave while we shop for your pretty new clothes, lean toward me dear.” He leans forward and I slip a leather collar around his throat and fasten it securely. “Now, that’s better, very good.” I told him to start the car and directed him to an adult themed lingerie shop I know a few minutes away. Much to my dismay we found that the store was already closed when we arrived but luckily I know the area well and direct him to the closest shopping mall. I straighten my leather skirt and adjust my black seamed nylons as we exit the car and notice more than a few heads turn as we walk into the busy shopping mall. I tell him to remove his coat so that the collar is plainly visible and strut through the mall with him toward my favorite store… Victoria’s Secret.

God, how I love to be surrounded by silky lacy things!! I flit from rack to rack looking at all the lovely things, waiting for something special to grab my attention. Ahhh yes, silky black tap pants, with sexy little slits on the side. Mmm yes these will do nicely. I have Stephanie stand up straight as I hold them against him, trying to judge his size. The sales girl nervously approaches and asks hesitantly if she can help me. “Do these come just a little larger hon? I am not quite sure they will fit.” (LOL Body by Victoria wasn’t expecting this guy builtlike a football player). She stammers a little and blushes, saying she isn’t sure, so I ask her sweetly to go check for me. I glance at Stephanie and notice a bright blush creep across his cheeks. He looks so lovely in pink and it makes me think of how nicely his other cheeks will look in pink. I pat him on the cheek and smile wickedly at him. He shifts nervously as the salesgirl returns and apologizes that that is the largest size they carry. “Hmm OK fine, well then let’s see if they fit dear. Come along.” We all walk toward the fitting rooms and the salesgirl fumbles her keys as she unlocks the door. He slips inside with the tap pants while I wait just outside the door.

A few moments later I call out, “How are you doing dear?” “They fit fine Mistress.” “Well, then open the door and let me see!” He opens the door and I see him standing there wearing only the silky black shorts, his very hard cock visibly straining at the thin material. “Excellent, dear now come along. we have much more to do.” I allow him to shut the door and get back into his clothing as I peek around at other things in the store, looking for something sweet to go with his new silky goodies.

He comes out quickly and is still flushed as I lead him to the stocking rack and look him up and down appraising his size. “Mmmmm yes definitely black thigh highs, but seams or no, that is the question.” I ponder this important decision as he nervously glances around the store to see if anyone is watching him and then looks back to me for reassurance. “Seams I think, they look so sexy with high heels, don’t you think luv?” “Yes, Mistress,” he stutters very softly and continues looking down. “Good, now I don’t think they are going to have much here in the way of camisoles to fit you baby, you are so broad across the chest you know.” “Yes, Mistress,” almost in a whisper. “Don’t worry, I have an idea for that. Come now, let’s pay for your new pretty things, we have another store to hit.”

We go to the register and I notice the look on the cashiers face then look at my little sissy and smile, he is looking down at his feet again and blushing incredibly and looking deliciously vulnerable. I can almost taste his humiliation and it is so sweet. She asks us if we would like to open a Victoria’s Secret credit account and I smile… “Maybe next time, I have a feeling we may be shopping here a lot, don’t you dear?” “Ummm yes, Mistress, thank you.”

He pays for his sweet new things and we leave the store. We stroll through the mall and can’t help but notice people staring at us as we pass. He blushes and looks nervous and I delight in his embarrassment and open his shirt collar wider so his collar is plainly visible. I want there to be no mistake that he belongs totally to me. We continue to the other end of the mall where Lane Bryant’s is located. We get a similar reaction there from the sales girls; surprised disbelief mixed with amusement. I strut through with Stephie and straight to the back of the store where the lingerie is located.

Thanking God silently for larger size shops, I find a rack with some lovely, and large silky slips. A sweet satiny purple one catches my eye and I pull it off the rack and hold it closely against Stephie’s body. The thin spaghetti straps hang from my fingertips as I dangle the silky material in front of his body looking to see how far down it reaches. I am pleased to see it barely covers his crotch area. I move around behind it holding it against his back and whisper to him about how much I will enjoy flipping it up over his ass so I can spank him. His eyes shift nervously around the store, trying to see who is watching as I size him up for the pretty top. I glance over to see a salesgirl pretending to straighten things on a rack while trying to appear not to be watching. I meet her eyes and smile brightly.

Turning my attention back to my sweet sissy, I tell him to hold the pretty purple slip while I go on searching the racks for sweet sexy things for my little slave to wear. I spy a very lacy black and red camisole and tell Stephie to hold it up against his body. I step back to look at it and him, picturing it on him wearing that, his new seemed hose and black pumps. I day dream just a moment picturing him dressed like that, cuffed and spread eagle tied with his hands high over head and his ass vulnerable and exposed, just waiting for me to have my way with him. He sees the evil smile on my face and blushes again, so sweetly, like an innocent child, defenseless and deliciously easy to violate. I lick my lips and smile at him, softer and playfully. There will be time for that later but now we must get back to the task at hand.

I like it baby, but the purple is nice too. Which do you prefer dear?” He searches my eyes briefly for a sign that I wish him to choose one over the other but finds none. He holds the purple one up and says softly, “I like this one Mistress.” “Then the purple slip it is then dear.” I take the red and black one back from him and place it on the rack, then move toward the back wall where the garter belts are hanging. I choose a large black one and hold it against his hips to make sure it is large enough to fit him properly. I see that it is and I hand it to him and tell him to but that as well. We head to the register and the salesgirl greets us with a nervous smile and asks if that will be all. “Yes thank you, that is it for today.” She rings up our purchases and hands me the bag, which I pass directly to Stephanie with a smile. As we leave the store I glance over my shoulder to see the sales girls giggling and whispering to themselves and then I look at Stephie and smile brightly.

“Well baby, now I want to see you in your pretty new things. Go to the men’s room and slip them on for me.:” He looked up at me with a panicked expression and stuttered questioningly, “Mistress, may I put them on under my regular clothes?” I stop and smile considering for a moment, after all he does have this wonderful full length coat, I could make him come out in just the lingerie and button his coat but that might be just a bit too much for our first shopping trip together. “Yes, baby… go ahead put your regular clothes on over. He sighed audibly and thanked me and scurried off to the bathroom while I took a seat in the food court area to wait for him. A moments later he returned with the most beautiful expression on his face, he glowed from within. I smile warmly at him and kissed his cheek. “OK baby, let’s head home now.”We continue out of the mall to the parking lot and get into his car. We sit in the car a moment and I tell him to remove his regular clothes and let me see him in all the new things. He blushes so sweetly and looks absolutely delightful.

“Did you have fun dear?” I ask him “Oh yes Mistress!! Thank you so much, that was wonderful!” “Well then,” I exclaim, “I think that I should have you thank me properly. Come here and kiss my feet baby.” I smile wickedly and get out of the car and stand behind his car in the open parking lot. He had the look of a frightened rabbit as he quickly got out of the car and scanned it for people walking around. He dropped to his knees in front of me and I slide my nails across his back feeling the silky texture of the lingerie. He moans slightly as he bends further down to kiss my boots. “You are such a sweet little slut Stephie, now get back in the car before you catch cold.” I get back in with him and kiss him very softly on the cheek. “I want you to take me back home then go home yourself and write me an email about this experience before you satisfy yourself, do you understand?” “Oh yes Ma’am, thank you Mistress.” Stephie did as he/she was told and his assignment is listed on my “Testimonials” page. We have had many other exciting adventures together, perhaps next time I will write about her “Quest’. Now that was a lovely adventure… but I will leave that for another day!