A little sissy lingerie shopping trip!

Sissy lingerie shopping adventures to start the New Year just right. I took my little sissy sub, Katelyn, out on an adventure around the city. Now, this adventure was a little different from the shopping trip I had with my humiliated sissy slut. That little submissive cross-dresser was always bratty. He frequently tried to get in trouble. However, Katelyn is a perfect little princess who tried on anything I picked out for her. And trust me, I reward my sissy sluts with the best shopping experience they could daydream of!

I knew little naughty Kate had been daydreaming of some red lace lingerie. Thanks to the holidays, I knew it’d be effortless to find her the perfect little outfit. However, I couldn’t just take Kate along to the mall with her still dressed as a guy. No, part of our sissy lingerie shopping trip started with me dressing her up at the start. We’d be walking for quite a while, so rather than get her some heels, I got her a cute little pair of strappy, sparkling sandals. She adored them, showing off her fresh maroon red pedicure. The sandals sparkled and dazzled in the lights. Then I moved on to the outfit itself.

She wore a little maroon dress.

It made our shopping trip much easier if she wore one tiny little slip-on dress. It was the sexiest dress in my closet, too. The fabric held a subtle sparkle, and the top half of the dress tied behind her neck, accentuating her cleavage. The dress fit snug over a little black lace push-up bra that I picked out to lift her boobs even higher. I added some curled clip-in extensions, and my sissy was ready to go. Katelyn was excited and giddy. She practically flew into the car as soon as I grabbed my keys. And so began our sissy lingerie shopping trip.

The first store we hit was Victoria’s Secret. How could we not? Since it’s a little past Christmas, they were filled to the brim with sales, as was the rest of the mall. Katelyn had a field day. She was embarrassed to walk through the store in full cross-dressing attire, so she blushed every time she had to speak to a sales assistant. However, they all spoke to her sweetly and showed her everything she was looking for. We bounced along the store sections, picking out a few lacy thongs and a few skimpy bras. She had her arms full of lingerie to try on by the time we got to the fitting rooms.

She tried on all the thongs first.

And, of course, I walked in with her. It’s not a proper sissy lingerie shopping trip without me properly supervising and checking her out as she tries things on! I even helped her adjust some of the straps and the sizing on some of her lingerie. However, I didn’t know my sissy had brought a surprise for me! As she was changing from one thong to the next, she bent over. Right between Katelyn’s little cheeks and ball sack sat a sparkling red crystal, peeking right out of her ass. The little sissy bitch had followed one of our fetish phone sex stories from the past and worn a little butt plug to her shopping trip!

And to make it naughtier – I could hear it vibrating. Little sissy Katelyn wore a vibrating butt plug on our shopping trip and turned it on when she got into the fitting rooms. She tried on every piece of lingerie I picked out for her, but the fun was far from over. As she bent over the fitting room bench, I came up behind her. I toyed with the little butt plug and tugged on it gently, and Katelyn moaned as quietly as she could. I wanted to press her further. So, I started tugging on the butt plug, then pushing it in. I stroked it in and out of her, stretching her little ass out as we hid away in the room. The little sissy was completely indulging in it.

She was ready to cum.

And she was wearing the brand new thong she’d just picked out from her sissy lingerie shopping trip! She hadn’t even taken it to the front register to buy it. But there she was, bent over the fitting room bench, with a butt plug in her ass, ready to cream her panties. And the adventure was far from others; we had plenty more stores to hit.

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