The Bet - Chapter 44 (Sunday – week 7 Part 6 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 6 of 9)

Ray pulled his big Cadillac into one of the empty parking places as close as he could get to the stairs. “I guess this is it,” he said to Derek as he looked up at the apartments above. “Somehow I was expecting something a bit nicer since she’s supposed to be a lawyer.”
Derek wasn’t really the least bit interested. He wasn’t looking forward to this “date” at all. “Who cares,” he replied.
“Certainly not me,” Ray returned brightly.
They got out of the car, but before going upstairs, Ray opened the back door and pulled out a bunch of flowers along with a small white box.
“I still can’t believe you actually bought her flowers!” Derek said as Ray pushed the car door closed the again with his leg. “And what’s that, chocolates or something?”
Ray just smiled. “Or something.” He suddenly looked like he had a small problem. “Oh hey,” he said. “Can you hold this for a moment so I can lock the car?” He handed Derek the box while he pulled his keys out and locked the car. Derek tried to hand him back the box, but Ray asked him to please hold it for him till he could give Mel the flowers. Thinking nothing of it, Derek carried the box upstairs with him. He stood back while Ray knocked on the door. He really wasn’t looking forward this!

“I’ll bet that’s the guys now!” Mel said as she quickly removed the robe she had covered her dress with to keep it clean.
She took one more look at Sissy, then she smiled at Sandy who had been standing in the background watching. “Well don’t just stand there Sissy, our dates are waiting!”
Nearly shaking with dread, Chad went to the door and opened it… and got a bit of a shock. Ray was standing there, holding a bunch of flowers!
Ray was a bit surprised to see Sissy at the door. He had been expecting Mel to open it. “Uh… Is Mel here?” he asked as he stared somewhat surprised at Sissy. He was mostly surprised because Sissy looked – pretty good!
Chad started to curtsey automatically, and stopped himself halfway through. “Of course,” he replied as he stood back out of the way to let the guys in. Derek just stared at Chad as he followed Ray through the doorway. The problem was that Chad couldn’t tell anything from the look on Derek’s face. Derek didn’t smile, but at least he didn’t frown either. Finally, he saw Derek nod a bit and Chad felt a wave of relief.
“Are those for me?” Mel’s excited voice cut through the room as she saw the flowers in Ray’s hand.
“Of course,” Ray replied. “Beautiful flowers for a beautiful lady.” He bowed slightly as he held them out for Mel to take.
“Oh brother!” Sandy muttered half under her breath as she rolled her eyes.
As Mel took the flowers, she tried remember any date bringing her flowers before – and the only one she could think of was for her senior prom in high school – and that was a corsage. “They’re beautiful! Thank you.” She sniffed at the flowers. “And they smell so nice!”
Derek started to hand Ray the small white box he was still carrying. But Ray just looked at him like he didn’t understand. “What are you giving that to me for?” Ray said. “You brought that for Sissy.”
Now it was Derek’s turn to be confused. “But…”
“Just give it to her,” Ray encouraged as he pointed toward Sissy. “You don’t need my permission.
Confused, Derek automatically turned toward where he thought Sissy was standing, but Sissy had moved closer now so he could see the flowers that Mel had gotten. As Derek turned, the box hit Sissy’s arm and nearly fell out of his hand. “Oh! I’m sorry,” he said automatically.
Chad’s knees felt like they were buckling. “That’s… for me?”
Derek, still confused, started to turn back toward Ray.
“Just give it to her,” Ray said. “You brought it.”
“But I…”
“You brought something for me?” Chad asked, still trying to figure things out too.
“Um… I guess so,” Derek replied with more than a bit of annoyance. He handed the box to Sissy, then he looked back at Ray quizzically, but also with a bit of menace on his face.
Chad took the box and opened it. And got another shock. Inside, he saw a small grouping of white flowers. He removed them from the box and realized they were attached to a plastic armband. “Oh my God!” he exclaimed. “It’s a…”
“You brought her a wrist corsage!” Mel exclaimed. “How sweet!”
“But I didn’t…” Derek tried to say again.
“Well don’t just stand there, put it on her,” Mel coaxed.
“But…” Derek gave up and looked angrily at Ray again for a moment – who was smiling back broadly. Then he grabbed the flowers from Sissy. Sissy, his knees definitely shaking now, held out his left wrist and Derek pulled the plastic band wide and slipped it over Sissy’s arm. The minute he did so, a small click sounded from a few feet away as Ray quickly took a picture with his cell phone. As fast as he had pulled it out, Ray had his cell phone put away again and out of sight.
Chad stared at the flowers attached to his wrist – not believing that it had just happened. He felt so funny inside about it. Humiliated, yet… something else too. “Th… Thank you,” he stammered. Then, catching a glimpse of Mel out of the corner of his eye, he dropped a very nice curtsey and repeated, “Thank you.” When he stood up again, he noticed that Mel was smiling broader than before. Whew! He had found a way to get past that one!
“Why don’t I put those in water for you,” Sandy offered as she took the flowers from Mel. “You guys just go and have a good time tonight.”
Ray smiled broadly at Sandy. “Another beautiful lady in the apartment. I may have to think about moving here.”
Sandy rolled her eyes again. It looked like Mel was right about this guy. “Don’t bother,” she replied. “I’m spoken for.”
Ray just shrugged his shoulders as if he didn’t really care about that at all.
“You guys just go!” Sandy said, trying to ignore him. “You’re probably going to be late for dinner.”
“Good idea,” Mel replied as she headed toward the door. She glanced again up at Ray. He had brought her flowers, and she knew without a doubt that he had “arranged” for Derek to give the wrist corsage to Sissy. As she walked outside, she was reconsidering her feelings about Ray. He might be a two-timing sleaze, but he was also without a doubt very handsome. And after seeing how he had just manipulated Derek, she had a feeling that he might be more fun than she originally thought!
As Ray followed her through the door, he was immensely proud of himself for setting up Derek to give Sissy the flowers like he did. And seeing how Mel was dressed tonight, he was more determined than ever to get her alone in a “more intimate” setting.
As Sissy walked out behind Ray, he was still trying to come to grips with getting the flowers – and he still couldn’t believe he was about to go out on a date – with a guy! Derek no less! How was he supposed to do this?
And as Derek walked out, he berated himself for being such a sap and a pushover that he let Ray get him into this position in the first place! He just thanked his lucky stars that Sissy looked fairly good tonight – almost surprisingly so. At least he wasn’t dressed like a hooker again!

Mel sat with Ray in the front seat of his car while Derek and Sissy sat in the back – together. As Ray pulled the car out of the apartment project and into traffic, Derek said softly to Sissy, “Thanks for at least looking decent tonight. I appreciate it.”
“No problem,” Sissy replied, just as softly. “Actually, I’m much happier dressing like this than what I wore to the poker game.”
Derek grunted. “If nobody looks too closely, they might even think I’m out with a real woman tonight.”
Chad blushed. “Thanks,” he replied. “I’ll still be happier when it’s over.”
“Me too!”

The restaurant Ray drove them to was one of the nicer, more expensive restaurants in the city. “Isn’t this a bit much for just a dinner and movie date?” Mel asked as he parked his car.
“Not really,” Ray replied. “Besides, with the way you’re dressed, I figured you probably didn’t want to go to a movie anyway. From here we can go to a nice club somewhere and really enjoy ourselves.”
“Not on you life!” Derek called from the back. “I’m not going clubbing with Sissy as my date!”
“Now, now, be kind,” Ray replied. “I think Sissy looks pretty good tonight too.”
“Then you date him!”
“Ah, ah! A bet’s a bet! And you lost! Besides, I’m looking forward to showing off what a super dish Mel is.”
“No club!” Derek repeated firmly. “I want a nice, quiet, dark, movie theater!”
Mel put her hand on Ray’s arm. “I think it would be better if we all just went to a movie tonight like we planned. That’s all this bet was for. Maybe next time we can go somewhere else.”
“We can let Derek and Sissy go to the movie while we go someplace better,” Ray suggested to her.
Mel shook her head. She knew it was better tonight if she kept an eye on Sissy the whole time. Besides, she had some tiny little “plans” for him tonight. “Not tonight. Just a movie and that’s it.”
Ray was clearly disappointed. “Well, you went to a lot of trouble getting all dressed up just for a movie. I didn’t want to waste it.”
Mel smiled. “Think of it as giving you a reason to ask me out again.”
Ray smiled. “Now you’re talking!”
A small unintelligible grumble was heard out of Derek from the backseat.

Chad felt strange as he walked beside Derek, behind Mel and Ray, toward the door to the restaurant. His very high heels made a loud distinct clicking sound with every step he took – a lighter, more noticeable sound than Mel’s shoes made. The wrist corsage felt strange on his left arm. He had to be very aware of the flowers sticking up from it so he didn’t hurt them. His new clutch also felt strange in his other hand. It kept brushing the full skirt of his blue dress as he walked. Did he look enough like a woman tonight? Silly question. It didn’t really matter. Mel would make him go through this no matter what!
For the first time since before the guys arrived, he thought about his diapers. He had been so preoccupied that he hadn’t been noticing if he was wetting himself or not. He knew he had to be. He was sure his diapers were probably fairly wet already, but the huge bulk of all three diapers made it hard to tell anything at all. It was just another little something he would have to worry about later.
Since Sissy and Derek hung back a bit, behind Ray and Mel, the hostess didn’t really notice Sissy all that much when they walked in. As they were being led to their table, Mel noticed something that might be helpful, the waiters were going around and automatically refilling all the iced-tea glasses. She hung back a bit so she could whisper to Sissy. “Order the iced tea with your meal tonight!”
The table was square and Mel and Sissy wound up sitting across from each other. Chad was glad because it meant that Mel wouldn’t be able to lean over and whisper any more little commands to him. When the waiter came by with the menus, Ray ordered a glass of wine for everyone. Sissy looked questioningly at Mel, but Mel only brightened at the wine suggestion and said it sounded great. Sissy wasn’t sure, but he thought he heard Derek softly grumble again.
As they looked over their menus and waited for the wine, Sissy and Derek were both quiet, but Ray talked animatedly with Mel. If Chad didn’t know better, the way Ray was acting, he and Derek might not have even been there. The wine arrived, was approved by Ray, and was poured for everyone. They each took a small sip before the waiter began asking for their orders. There had been a lot of really interesting entries on the menu – all of them extremely high priced – and Sissy had been planning on ordering one of the steaks. Something like that to chew would have tasted great. He might not be able to finish it all, but it still sounded good.
The waiter started with Mel, who surprisingly ordered only one of the exotic dinner salads on the menu along with a cup of coffee. “That’s all you want?” Ray asked with some surprise. “You can have anything you want.”
Mel shook her head. “I still have to watch my figure,” she replied. Then she looked straight at Sissy as she added, “Everything on the menu sounds so good, and also so fattening!” Ray only chuckled, and said nothing else about it, but since she had been looking straight at Sissy when she said it, Sissy got the message clearly.
The waiter moved on to Sissy next, and for the first time looked at him more closely. It took him two seconds for his brain to register that there was something different about her. A moment later, total realization set in, and once he noticed it, he couldn’t help not seeing Sissy as a man dressed up like a woman. All further pretense went totally out the window when Sissy opened his mouth and spoke in his “girly” voice. Sissy ordered the same thing that Mel was having, except as Mel had dictated, he got iced tea instead of coffee. When he was done ordering, Sissy saw the waiter just staring at him for a moment. Un-approvingly? He wasn’t sure, but that’s the impression he got. Fortunately, the waiter moved on to Derek next and didn’t say anything else.
When the waiter left, Mel and Ray continued to talk while Sissy and Derek just listened. A few times, Derek and Sissy looked at each other, both of them silently acknowledging the awkwardness of the situation. Sissy kept sipping at his wine to help pass the time. As he did so, he couldn’t help but notice the red lipstick stain on the rim of his glass. Each time he picked it up, he tried to drink from the same spot so as not to spread the stain any further.
A few minutes after the waiter left, unexpected music filled the room. From where they all sat, they could just see two musicians up on a stage providing soft entertaining music. There was a woman playing an electronic keyboard, and a man with her who was accompanying her with a string bass. They both sang and together and they sounded surprisingly good. Sissy was glad to see the musicians. It gave him something else to concentrate on instead of the strange situation he was in. Not only that, but maybe everyone else in the restaurant would be paying more attention to the musicians too – and less attention to him. After a few minutes, Sissy noticed one of the couples closer to the musicians get up from their table and start dancing. He smiled. How nice. They were quickly joined by another couple from another table.
Sissy’s glass of wine was about three quarters done when he saw Mel looking at him again. Ray was talking and Mel appeared to be listening, but Sissy saw her rest her elbows on the table and her chin in her hands for a moment. Ray obviously thought nothing of it. But when Mel began tapping her finger against her own lips while looking at Sissy, Sissy got the message. Even sitting across the table from him, she was finding little ways to give him orders! He opened his purse and pulled out his compact and checked his face in the mirror. He decided everything still looked good, including his lipstick, so he put the compact away again. He saw Mel smile briefly at him. As far as he could tell, Derek hardly noticed – or at least he made no reaction. And Ray was still talking to Mel and probably never even saw him do it. Sissy picked up his wine glass and emptied it!
“Shall we dance?”
Mel was startled by the sudden suggestion. “Here? Now?”
“Why not?” Ray replied. “There’s plenty of room in front of where the band is playing.”
Mel looked and saw three or four couples dancing now. “Why not?” she suddenly decided and got up from her seat.
Sissy saw Ray look briefly back at Derek as if taunting him. Derek’s face didn’t look all that happy about it as he watched them heading toward the music. They were alone in the restaurant – together. Awkward! Awkward! Awkward!
Not wanting to watch Ray dancing with Mel, which would only be like him rubbing things in, Derek looked away from the dancers, which really left him only Sissy to look at.
“So far, so good,” Sissy said, trying to fill the awkward silence.
Derek grunted, but nodded his head. “Yeah, so far.”
Wanting to continue the conversation, Sissy added, “It’s a nice place. I’ve never been here before.”
Derek shrugged. “I’ve been a few times, but it’s been a while.”
Sissy didn’t know why, but he suddenly thought about Robin. Obviously, she hadn’t told anyone yet – or at least the word hadn’t gotten to Derek yet. “I’m more worried about tomorrow,” he said.
“Tomorrow?”
“At work. What’s everyone going to be saying?”
For the first time, Derek smiled. “I’m not going to have to worry about that, because I’m not going to be there. I’ll be flying out early tomorrow morning.”
“You’re lucky!”
Derek nodded. “About that anyway.”
“I’ll have to put up with all the women asking me tons of dumb questions.”
“You’re the one who wanted to be a woman! Don’t complain to me about that!”
Chad considered telling him how wrong he was, but all he could really do in the situation was to smile and say, “I guess your right.”
“You are getting better at it,” Derek said.
Chad felt himself blushing slightly. “Thanks. I’m trying.”
“But you’ve still got a long way to go!”
That kind of knocked the wind out of Chad a little. “Like I said, I’m trying.”
As they talked, they didn’t see Ray and Mel coming back from the dance floor and stopping a short distance away. Ray pulled out his cell phone again and took another quick picture as Mel giggled.
Derek and Sissy were saved from further conversation as Mel and Ray came back and sat down again. And once again Ray dominated the conversation – with Mel. Two minutes later, Mel was tapping her lips and Chad had to check his makeup again. Nothing had changed! How could it?