The Bet
by Karen Singer
Chapter 36 (Saturday – week 5 Part 5 of 8)
Mel was ready and waiting for him when he knocked. She grabbed her purse, and his diaper bag and opened the door. She was immediately greeted by him with his usual curtsey. She smiled and simply pushed past him.
Chad was a bit nervous about going to the mall. The last time he was there was when she had dressed him up in one of his super sissy dresses and made him act like a super sissy inside. So embarrassing! Would anyone remember him from that? Quite possibly! Since he was still recognizable as a man wearing women’s clothes, he figured that it would be very easy for anyone to make the association. Not a good thing as far as he was concerned!
Mel parked the car. Chad hesitated a moment before getting out, as if he was trying to find the courage within himself to go into the mall again, but he delayed only for a moment. Then he followed Mel inside where she handed him his own diaper bag to carry so she wouldn’t have to lug it around.
Whenever he had been out with her before, dressed in his maid’s uniform, it was obvious to everyone that he was her servant. Now, strangely, she was walking beside him and chatting with him about things she saw in the display windows as if he was her best girlfriend. It seemed so strange. He often didn’t know how to properly reply to her comments but fortunately, she didn’t seem to mind the times when he said nothing.
She led him into many stores, always telling him to look to see if there was anything he wanted to buy for himself. But Chad wasn’t really interested in looking at anything for himself. He did get the “privilege” of holding her purse often while she tried on different outfits. Somehow, dressed as he was, holding her purse didn’t seem to matter much at all.
When they finally got to the department store where he had bought his makeup, Mel again teased him about asking for another makeup demonstration, but again Chad politely refused. He did have to ask for all the makeup items he needed in his stupid sissy voice though – since Mel was standing right next to him – which gave the makeup girl quite a shock at first, then sent her into fits of laughter. Embarrassing! But fortunately, Mel didn’t make him do anything else there to embarrass him further.
It wasn’t till they left the store and headed out into the mall area that Mel paused and stopped. There was a store stuck in the corner, just off of the entrance to the department store that had been there a very long time. But it was one of those stores that she had never bothered with before, so she barely ever noticed it. But now… now it sparked not only interest, but also, fantasies! Much to Chad’s horror, she headed straight for it.
The dancewear shop that they entered wasn’t huge, space wise, but the store was so packed with display racks that it was hard to move without constantly brushing against something. The moment they entered, Chad started to hang back neat the entrance. Horrible visions of her sending him to work in a pink ballet outfit were constantly running through his mind.
Mel walked right up to the woman behind the counter. “May I help you?” the woman asked politely.
Mel smiled. “I’d like an outfit for…” She looked around for Sissy, but he wasn’t there. She finally spotted him half hidden by one of the racks near the door. “Sissy! Get over here!”
Chad hated it, but he grudgingly moved toward the counter.
Mel returned her gaze back to the saleswoman. “I need it for… her!”
The woman looked Chad over carefully. Her surprise showed obviously in her eyes. “You’re serious?” she asked Mel.
“Of course,” Mel replied, slightly put off. Chad lowered his embarrassed gaze down to the floor, searching for that hole that never appeared to swallow him up.
The saleswoman finally shrugged and replied. “What exactly did you have in mind?”
Mel smiled again, wickedly, but she smiled. I think a pink leotard, white tights, a white tutu, and pink toe-shoes.
The woman looked at her for a moment to take it all in. “Okay, she finally said. “The tights are the easiest.” She moved out from behind the counter and went directly to a display rack against one of the walls. “How many pairs?” she asked.
“Just one, for now,” Mel replied.
The saleswoman looked at Chad once again to gauge his size, then selected a package of white tights in his size from the rack which she handed to Mel. “Now, as to the leotard…” She led the way to a rack of them in all different colors. “Let’s just get the style you’d like first. I’ve probably got the color in the back somewhere.”
Mel picked out a fairly simple leotard with a scooped neck and short sleeves. After glancing quickly at Sissy again, the saleswoman excused herself and went to the back room where she found one in pink and brought it out. “That’s the easy part,” she said to Mel as she handed the leotard over. “Now, what style tutu?”
“What’s available?” Mel asked. “I’d really like something that is wide, but not too long.”
“Classic or pancake style?” the woman asked.
Mel thought about that for a moment. “Probably pancake,” she replied. “Do you have any that I can see?”
Chad suddenly didn’t have a clue as to what they were talking about. The woman led them back up to the counter where she opened a book and started going through the pictures with Mel. Mel quickly pointed to one of the pictures. “That! That’s exactly what I’m looking for.”
The saleswoman smiled. “In white, I think you said?”
Mel nodded. “Definitely in white.”
The woman returned to the back room. She was gone a while, then she came back again. “I’m sorry,” she said as she returned. “But we’ve sold out of everything we had in that style. We should be getting some in next week or the week after if you’d like to check back then. Of course, we can always order you one if you like.”
Mel considered it, but decided to delay her decision. “How about the pink toe shoes?”
The saleswoman again looked at Sissy. “What size shoe do you take?”
“Ladies size nine,” Mel replied for him.
Chad winced. Size nine was fine, he could wear shoes in that size, but they were tight.
The woman went back to the back room again. When she returned, she was once again empty handed. “It seems were out of those too,” she apologized. “I’m afraid the dance schools all have their recitals this time of year and we’ve been selling out of some things as fast as we can get them in.”
“In that case, order a pair for me… the tutu too.”
Words that Chad very much didn’t want to hear. He could already see her dropping him off at work in the outfit and stranding him there. And curiously, for the first time in a while, he was aware of how sexually arousing the concept was… not that his main sexual member was even capable of reacting to it anymore.
“You’ll have to pay in advance, I’m afraid,” the woman said to Mel.
“No problem. That should be fine.” She turned to Sissy. “Get over here and pay for all this stuff. It’s all for you anyway.”
Chad was forced to pay for everything, but Mel gave the woman her own phone number and address so that she could pick the missing items up when they arrived.
Feeling slightly disappointed that she couldn’t get everything now, but still very happy and excited about what was soon in the future, Mel led the way back out of the store. Chad now had another bag to carry along with his bag full of makeup, his purse, and his diaper bag. Mel seemed happier than she had been all day.
Chad was more worried than ever! “Mistress,” he said in his best sissy voice. “I thought I’ve done everything you wanted. And now you’re still going to send me to work in the ballet outfit?”
Mel was amused. “I haven’t decided yet,” she told him. “Yes, you’ve done everything I’ve asked, but I can’t very well decide to send you like that in the future if we don’t have the outfit first.” She decided to let him stew on that thought for a bit. Besides, it was true!
But Chad’s fears were only partially allayed. No, she wasn’t planning on sending him to work that way… yet. But there was still the future to worry about.
A little while later, Chad checked his watch. His two hour time limit was quickly drawing nearer. He was very wet, but not yet wet enough for his diaper to be leaking any time soon. “Mistress,” he said in his sissy voice. “Maybe it would be a good idea if we went home soon. My two hour limit is almost up.”
“Are you leaking yet?” Mel asked, not even bothering to look away from the display window she was staring into.
“Not yet, Mistress. But something to drink would be a big help. I haven’t had anything in quite a while now.”
Mel realized that it was true. She wasn’t really helping matters by ignoring that fact. And keeping him wetting had to be her first priority. “Let’s stop and get a drink first,” she suggested.
Chad would have been a lot happier if they had just gone home first. A short while later, he was sipping on a very large soft drink while Mel continued shopping. Not being able to carry the drink into the stores, Chad was forced to stay out in the mall area while Mel went inside. During one of her trips into a store, he took the opportunity to sit on a bench and take the strain off of his tired and aching toes.
“Didn’t I see you here last week… doing some kind of dance and singing some crazy song?” a voice from nearby asked.
Chad, horrified, turned and saw an older man sitting on the next bench looking at him. He realized that the area he was sitting in was the same area he had “performed” in when Mel had brought him here in his super sissy dress.
But when Chad had turned to look at the man, the man definitely recognized him. “That was you!” the man added with a slight laugh. “You were wearing some crazy outfit too. I got a real kick out of it!”
“Uh… Thanks,” Chad answered, not knowing what else to say. “I’m glad you enjoyed it.”
“Most interesting thing I’ve seen here in ages!” the man replied. “Are you going to do it again?”
“I hope not!” Chad stated, fervently hoping that it would be true.
“Pity,” the man said. “I rather enjoyed it.”
Unfortunately, that was the point where Mel walked up. “Enjoyed what?” she asked.
“His little show last week,” the man replied.
“We’re glad you enjoyed it,” Mel said to him with a broad smile on her face. “We’re considering doing it again, only maybe something better next time.”
The man’s face showed his complete interest. “When?” he asked anxiously.
Mel shook her head. “I don’t know yet. “We haven’t decided.”
“Well, I’m here most days about this time,” the man replied. “Got nothing better to do, just getting out of the house for some exercise and people watching. I hope you do it while I’m here!”
Mel smiled at him. “We’ll try.”
Chad was beside himself. Do it again? Something better? Where was that tidal wave that was supposed to come through and wash everything away?
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