THE PLACE WAS PACKED. I guess word had gotten out. I went up to the hostess to see how long the wait was. It turned out she was one of the girls Greg had dated. She was two or three years older than Greg. She told me the wait time was forty minutes, so I slipped her a twenty and the forty minutes disappeared.
“Reservation for Dawson!” she proclaimed.
When we got to the table, everyone was curious.
“What did you do?” Cassidy accused me.
“Hey, settle down, you’re with a VIP.”
“I call bullshit,” Jim said.
“All right, you got me. She used to date my brother.”
“That would do it,” Cindy agreed.
“You’re kidding, right? There are two like him? I thought his brother had a steady girl,” Coach Hope said.
“David’s brother, Greg, is a legend. He has dated almost everyone worth dating at Lincoln High,” Jim said. “Now David’s recycling Greg’s old girlfriends.”
I could see Cindy didn’t care for the characterization.
“I like to say that we have excellent taste in women. For example, Cindy is a very special lady. Any boy would be lucky to go out with her.”
Jim blushed.
“This is fascinating. Who else have you both dated?” Coach asked.
“Let’s see. They’ve both dated Jim’s sister, Suzanne,” Cindy said, sending a shot across Jim’s bow.
“Didn’t Greg date Peggy Pratt?” Jim asked.
“Yes, let’s just say there are a handful of special ladies that we’ve both dated,” I said, hopefully ending that discussion.
The waiter took our drink orders, and I ordered a variety of appetizers since no one was sure if it was okay.
I turned to Cindy.
“You want to go with me and meet people?”
“What’s he talking about?” Coach asked.
“David goes around and talks to everyone. I swear he’s going to be a politician someday,” Jim supplied.
“I’ll pass,” Cindy said.
“Do you mind if I go?” Coach asked, surprising me.
“No, not at all.”
We got up and started toward Mona Wingman’s parents. Before we got to their table, I clued Coach in.
“My dad has had Greg and me doing this for years. He says you never know when something like this will pay off. I also try and find parents of people that I’m playing ball with. I brag them up.”
I put on my best smile.
“Hey, Mr. and Mrs. Wingman, I’d like you to meet our new football coach, Tony Hope.”
The last one he handled himself. It was Mr. and Mrs. Sullivan. She was the head of our new booster club. She invited us to sit down and talk. I said I’d go back to our table so they could talk business.
I made it in time to eat some appetizers. Cassidy’s dad was still talking when they came for our entrée orders. I had Cassidy order for her dad. When our steaks came, he was still deep in conversation. I had the waiter offer to serve him at the other table. He went ahead and took his meal there, and luckily they were served shortly after us, so it wasn’t awkward.
All evening the girls seemed to be up to something. Finally, even Jim keyed in on their nervous energy. He has a sister, so he isn’t totally clueless.
“Out with it. You two have been dancing around something all night. What is it?” Jim asked.
They both looked at each other and Cassidy went bright red. I knew it had to be something sexy because Cassidy is usually very confident. That left it up to Cindy to tell us.
“We want to go back to David’s apartment,” she started.
“Ah, no can do. My apartment is off-limits till the end of school, per the ’rents. Let’s just say I’m not inclined to test them yet.”
If ever.
“Then we can go to my pool house,” Cindy offered.
“That’s fine, but there’s more to this,” Jim said, looking at Cassidy.
“I was talking to Cindy and, ahh ... she told me she showed David some stuff ... and I thought ...” Cassidy said just over a whisper.
It took Jim a moment to catch on. I could tell he was going to say HELL NO! I took him to the restroom to talk.
“Before you reject Cassidy’s plan, let me tell you why you might want to consider it. First of all, this is one of the ways Greg taught me. This is no small gift that Cindy’s offering both of you. I would highly recommend it. Also, there will be a rule. This is one that we can both agree on: if either or both of our penises are exposed, they will never enter the other guy’s date. Finally, you and I have seen each other naked numerous times. Neither one of us has anything to be ashamed of.”
“Do you think I should do this?” Jim asked.
“I’ll give you two answers; you have to choose what’s best for you. Doing something new like this is scary. I personally have my doubts about this. The only reason I’m talking to you is because it took a lot of courage for Cassidy to ask us. But if you aren’t sure, then don’t do it.
“The second answer is, why not? You can’t let fear run your life. It’ll make you miss out on experiences that later in life you’ll be kicking yourself over. I’ll bet that you’ll learn something tonight that will serve you the rest of your life, IF you take that chance.
“So, what’s it going to be?” I asked.
“Dude, if it was anyone other than you, I’d be out. I trust you, and I know Cassidy trusts you.”
“All right, let’s go make our dates happy.”
I could tell Cassidy was relieved. Then it hit her: this was happening. I winked at her to let her know it would be okay. We got ready to leave, so I went over to say goodbye to the adults.
“David, I want to thank you for bringing Tony over. He tells me that you’re one of the student organizers that have put everything in motion,” Mrs. Sullivan said.
“Yes, ma’am. Coach Hope has really worked with us, and our parents, to improve things at Lincoln. I truly think we can be a powerhouse in sports, across the board. With the leadership of people like yourself and Coach, we can get this done.”
“Well said, young man,” Mr. Sullivan said.
“Thanks, David. By the way, what are you kids doing now?” Coach asked.
I raised my eyebrows.
“Are you sure you want to ask teenagers what they’re up to?”
“Yes.”
“Okay, you asked for it: We’re going to Cindy’s house for a hot foursome,” I said with a straight face.
“Get out of here. This kid is my worst nightmare,” he told the Sullivans. They broke up laughing. “No, seriously, thanks for the steak and being Cassidy’s friend. Go have fun.”
“Yes, sir.”
I met everyone at the door.
“What did Daddy want?”
“He wanted to know what we’re going to do, so I told him.”
None of them believed me.
CINDY’S POOL HOUSE had a guest room, which is just a normal-size bedroom with king-size bed. Jim and I looked at each other, not really sure what the girls had in mind. Cindy had taken the lead in teaching me, so I hoped she would do the same tonight. I wasn’t disappointed.
“Gentlemen, tonight is about learning. You’ll not be removing your underwear. You will be learning to give your partner pleasure. If that goes well, we’ll see how everything progresses from there.”
She gave us a big smile.
“All right boys, strip.”
Jim and I looked at each other, and he was nervous. I was surprised that I was, too. It wasn’t because I was body-shy, it was because there was a sexual tension in the air. I was nervous this might get out of hand. I liked all three of them and didn’t want to see anyone get hurt. The deciding factor was that I trusted them all. I gave Jim a smile and started to take my clothes off. He followed my lead.
Jim was a good-looking guy. His build was different than mine. Where I was leaner and had more muscle definition, he was solid. He wasn’t overweight but was strong as an ox. The girls appreciated the show. Both Jim and I were obviously aroused. There was no hiding that we’d stretched our boxers.