Fact and Fantasy 1: The Shopping Trip
by: Sissy Demi

 

"Can I help you find anything?"

The salesgirl’s voice startled me a little. I turned and smiled at her, then held up the two tops I had been debating over, one in each hand.

"Actually, yes, you can," I answered, still smiling. "I can’t decide which of these to get. Maybe you can help me decide?" The salesgirl nodded and turned her eyes to the shirt I I held out first.

"This one?" I inquired.

It was a lavender stretch shirt, princess seamed with three-quarter sleeves ending in cute turned back cuffs. I already had one similar to it in white, except this one had the longer, more pointed style of collar.

"Or, this one?" I held the second one out for her to see clearly.

This one was a very cute hot pink knit top in a cotton-lycra blend. Very stretchy and form fitting. It, too, had the popular three-quarter sleeves, but these ended in a one-inch ruffle. The neckline was scooped, though not deeply.

"They are both very contemporary styles, ma’am, and either would look fantastic on you!" the salesgirl enthused. I knew she was going to say something like that. I wanted to coax her into doing it so I could drop my surprise on her, see if she really wanted to make a sale or not.

"Oh, it’s not for me," I said, shaking my head. Her eyes got a knowing look, thinking, I’m sure, I was going to say it was for a friend or relative. She was right, but not the way she imagined.

"They’re for my brother."

The salesgirl’s eyes widened in confusion as she turned her head and followed my arm that now pointed at my younger brother standing slightly behind a nearby clothes rack. His face was flushed in humiliation.

"You… You’re going to make him look like… like a girl?" the salesgirl stammered, looking back at me. Her eyes kept darting back to my mortified brother. She looked like she was trying to keep from laughing in shock or amusement.

"No," I answered casually. "He’s going to be dressed like a sissy boy. I want everyone to know that he’s just a boy in girl’s clothes. At least when they see him up close."

My brother turned an even deeper shade of crimson and hung his head in shame. The salesgirl’s head swept back and forth between him and I, trying to figure out if this was a joke being played on her or something for real.

"You’re serious?" she asked. I nodded gravely. "Why are you doing this to him? I mean, did he do something bad to deserve this or what?"

I motioned my brother to come over and stand next to me. He shuffled over, head still bowed. I placed a finger under his chin and forced him to lift his head.

"He is a bully sometimes," I told her. "He doesn’t usually use physical force on anyone, but he seems to dearly enjoy verbally teasing and insulting others. Especially boys who are smaller than him. He calls them ’sissy’ and ’pantywaist’." The salesgirl was nodding in understanding as I spoke. "Even girl’s get unmercifully teased by him; pulling their hair or making fun of what they are wearing. Isn’t that right, Chris?"

I looked hard at my blushing brother. He shrugged a little, but looked even more scared as he saw the salesgirl was glaring at him.

"So, our mother decided he should see how it feels and left it up to me to make sure he does," I looked smug. "This is my solution."

The salesgirl muttered how she couldn’t stand bullies when she was in school and thought this was a great way to get one back, all the while glaring at Chris. She turned to me and said she’d be happy to help. I was relieved, glad she didn’t freak out.

She brought my attention to the clearance sign on the rack I had taken the two tops from. Fifty percent off. She said I could get him both for what I was figuring on paying for one, now. I beamed and thanked her, handing the two tops to Chris to carry.

"We have some really cute skirts I bet he’ll be so embarrassed to wear!" the salesgirl gushed, getting into it. I shook my head, though.

"No. Not right now, anyway. Only girls wear skirts and he isn’t going to be a girl. Just a sissy. I’d like to find him jeans or shorts. Something girlish, though. He’ll only wear skirts for special things." My brother looked sharply at me when I said that. The salesgirl giggled and seemed to think for a moment.

"We have a few things that may be just what you’re looking for," she said brightly.

"Great!" I beamed back. "Tell you what, you find something for him to match the pink top. I want him to try it on before we buy it, if that’s ok?" She said it was fine; no one was using the fitting rooms now so it shouldn‘t be problem.

"Good," I smiled, turning to Chris. "Go try on the pink top and whatever bottoms she hands you. Do you understand?"

He nodded slowly, face still red, and trudged off towards the fitting rooms. The salesgirl, Judy I now noticed her nametag read, turned to me.

"What about a bra to fill it out a little?" She asked.

"No," I chuckled at her enthusiasm. "I want him flat-chested. Fifteen-year-old girls would have some development by now, but like I said, I don’t want him to look totally like a girl. Besides, he’s already wearing a pair of pink satin panties that don’t fit me anymore. You should have heard him holler when I made him put them on before coming here!" We both laughed.

Judy went off to get the item she had in mind for Chris while I rummaged through a few more of the racks, looking for other things for him to wear. A short time later, I had found a couple more outfits I thought would be cute for him and headed towards the fitting rooms.

Judy was waiting outside of them for me. She grinned from ear to ear as I walked up and placed my other selections on the counter.

"I had to help him get dressed in what I picked," she told me, conspiratorially winking. "I saw the panties. Very cute!" She giggled. "Are you ready to see him?"

I smiled and said yes. Judy stuck her head in the archway and called for Chris to come show us his cute new clothes. He came shuffling out, still red in embarrassment and with his head hung low.

"Oh, that’s just adorable on him!" I almost squealed when I saw him. "Excellent choice."

He stood there in the pink knit top. The ruffled sleeves ended just below his elbows. The cotton-lycra clung to him well, seeming to emphasize his very boyish chest, as opposed to enhancing the small breasts a girl his age might have had. The scoop neck made this contrast even more noticeable as well as making his boyish face and hair very obvious.

Judy had even placed two small, pink barrettes in his hair on the left, much like a girl would wear. Yet it did little to make his hairstyle seem very feminine. I loved it. But I loved what else she had picked out for him even more.

It was a pair of dark blue denim capris. The legs ended just at mid calf and had a bright pink flower pattern at the hem, fading upwards for about six inches. The capris looked like they might be a bit stretchy as they were a bit form fitting from his waist to crotch. It made the fact he was a boy even more prominent since no effort had been made by him to hide his genitals. A small, very un-girlish bulge made that all too evident on the flat front. I could see they were back zipped, too.

I looked to Judy and gave her a quick hug.

"That is sooo perfect," I was grinning at how boyishly sissy Chris looked. "I’ll take it! Ring them up with the other stuff, please." Chris’ head snapped to look at the small pile of clothes on the counter, trying to figure out what was up there.

"Go put your sneakers back on, Chris," I told him sweetly. "And, put the clothes you wore before into a bag." His eyes got wide, realizing I wasn’t letting him change out of the cute capris and top outfit.

"After I finish paying Judy, and since you have not given me much trouble so far today, we can go to the arcade so you can play a few games and say hello to your friends before we get you some shoes to go with that!" I smiled as he looked about to faint…

 

fin?-

 

 

 

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© 2001 by Sissy Demi. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.