“What would be a good first date?” he asked.
I got serious and thought about it for a minute.
“How about I meet her at the football game?”
Both Cindy and Greg shook their heads ‘no.’
“First of all, do you want Jeff and Alan hanging around you? Or better yet, how about her friends?” Greg asked.
“You want the first date to be something where you can get to know each other better. The first date needs to be something that can either be short, if it’s not working out, or can be longer if it is,” Cindy added.
I looked confused. Thankfully, my brother had a solution.
“This was Cindy and my first date: I asked her to Jerry’s Ice Cream after school. It’s right next to the park, so if things are going well you can spend time taking a nice walk.”
Jerry’s was an institution. They have the best ice cream in town.
“I remember that. You kissed me on the bridge and then, well, it was the best first date I’ve ever had.”
“I think I’ve got it,” I said, and then asked her out. “Cindy, would you like to go to Jerry’s and get an ice cream after school on Friday?”
“Why, David, yes I would.”
“Good job, let’s talk about appearance. You need to look like a boy a girl would want to be seen with; no girl wants to be seen kissing some dork. You have to look the part,” Greg said.
That one hurt. What was wrong with what my clothes looked like? Greg could see that he hadn’t worded that quite right.
“I’m not trying to be mean, I’m trying to help,” he said softly.
I just nodded at Greg. Wait a minute, did someone say kissing? If I hadn’t caught it, Mr. Happy sure noticed.
Cindy was pragmatic.
“You need a haircut, and your clothes need a makeover. I’ve only seen you in old jeans and bad t-shirts. No girl wants to be seen with someone who has on an ‘I’m with stupid’ t-shirt.”
Sure enough, it was what I had on, but I didn’t want to be some Ken-doll knockoff either.
“Cindy has volunteered to help you in the next few days to get you looking like someone girls would date,” Greg said.
I was relieved. I wanted to make a good impression. It looked like ‘plan Peggy’ was shaping up. Cindy clapped her hands.
“Goody, I always wanted to make a guy over. Now for your reward: c’mere and kiss me.”
I wasn’t going to pass this up, and I think they were both surprised when I walked up to her and kissed her. The first kiss was gentle and tentative. Okay, give me a break. My brother’s girlfriend was hot, and he was within punching distance; but hell, yes, she was in a silk robe. I reached out, put my hands on her hips and gave her a second kiss. This one had more passion in it and lasted much longer. I slightly parted my lips and I found a tongue in my mouth. I was a little taken aback, but I found I enjoyed it. I decided to give as well as receive. When my tongue snaked into her mouth, Cindy moaned. Her hands went from my chest to the back of my neck.
Her fingers ran through my hair. I felt her melt into my arms and her body mold into mine. She just kind of eased onto me. I knew she could feel my desire press into her, but my mind had short-circuited because her silk robe was almost as good as having her nude in my arms. I felt her firm breasts and hard nipples drill into my chest. My hands found their way to her butt as I pulled her tightly against me. I was lost in the moment.
I heard Greg clear his throat.
“Okay, horndog, I think the lesson’s over for today.”
The best make-out session I’ve ever had was with my brother’s girlfriend while he watched. I prayed he didn’t plan to kill me in my sleep. I’d really forgotten where I was and whom I was with. As I disengaged from Cindy, I noticed that her robe had fallen open to her navel. It barely covered her naughty bits. Okay, she was definitely a 10.
As we parted, we were both aroused. Cindy’s chest was flushed, and she had a predatory look in her eyes. I felt like a little rabbit that was being stalked by a jungle cat. My heart beat like there was a hummingbird trapped in my chest. I broke eye contact with Cindy and looked Greg in the eye. He was trying not to laugh. All I could say was I was sorry.
Cindy smiled at me and I swear she purred.
“No need to be sorry, you come by your kissing talents naturally. If I decide to dump this lug I’ll look you up.”
Damn, Greg was a lucky man. Cindy made no move to cover up as she walked over to Greg.
“I think you need some practice too. Your little brother may be a better kisser than you are.”
Greg growled at her and put a serious lip-lock on her. He teased her.
“You little skank, you’re teasing my poor brother with all your goodies hanging halfway out.”
She squealed as he swatted her butt.
“David, do you feel abused?” she asked.
I laughed as she flashed me her breasts. Greg grinned from ear to ear.
“I’m not sure I can trust you with my little brother.”
She looked at my jeans.
“I’m not so sure he’s little!”
Greg just rolled his eyes. I knew I had nothing to be ashamed of. I wasn’t the biggest guy around, but as far as other freshmen were concerned, I had one of the larger sizes, based on what I saw in gym class.
It was time to go home.
“Thanks for today’s lesson,” I said once we were in the car.
“Okay, here’s this week’s homework. First, you’re going to let Cindy make you over. You do whatever she tells you. And second, you’ll ask someone out for Friday night.”
“Should I ask Peggy?”
“Before you go to the big leagues and ask her out, let’s get you a few training dates,” Greg coached me.
“You’re the boss.”
WHEN WE GOT HOME, DAD was making dinner. Mom was out selling a home. Dad, Greg and I had learned to fend for ourselves, so it was no surprise to see Dad cooking, and it smelled wonderful. Greg and I never told Mom that Dad was a better cook.
“Greg, come make a salad. David, you set the table and get us drinks.”
We quietly fell into our tasks. After I was done, I walked up behind Dad and peeked over his shoulder to see what he was making. It was Salisbury steak with brown gravy and mashed potatoes. It looked like he’d made the mashed potatoes from scratch. He noticed me, turned and gave me a hug and a kiss.
Dad had always kissed us. When Greg turned eleven, it was decided we would no longer be kissed on the lips. Some of Greg’s friends had commented on it. After he hugged me he went over, hugged, and kissed Greg. Dad always made me feel loved. It was just his open, friendly personality. He had a charisma that just seemed to draw people to him, and to like him. Greg had inherited the same thing. I just wished I had half of their charm.
“How was your day at school?” Dad asked me.
Dad and I shared everything, so Greg wasn’t surprised with what followed.
“Today was great. I like all my classes except English; that looks like it might be hard. I got reacquainted with all my friends. Jeff and Alan seem great. The other morning Peggy Pratt got caught in the rain, so I gave her a towel and t-shirt out of my gym bag so she wouldn’t have to be wet all day.”
“I tell you, Dad, David made a lot of enemies yesterday. No one was happy he gave her a dry t-shirt,” Greg said with a chuckle.
We all went to the table and started eating. It felt good to be having our family dinner together where we shared our day. Dad had a big smile on his face too, so I continued.
“That may be, but I’m not too worried about the guys at school. I’ll be worried if the girls are all mad at me.”
“He has nothing to worry about. You should hear what all the girls were saying about him at lunch. ‘Little Dawson grew up over the summer. He was so cute! And did you see his nice butt?’”
I threatened to flick mashed potatoes at Greg.
“Settle down, guys,” Dad warned us.
“After school Greg asked me to help him and Cindy out by sitting for some neighbor kids. In return they’re helping me with my dating skills.”