A Flirting Workshop with My Sister

I sighed. As much as I wanted a girlfriend, I couldn't see it happening anytime soon.

* * * *

I got back home at 10:15. The shirt I was wearing was appropriate for playing with Bart and taking him for a long walk, but I thought I should change into something nicer for the flirting workshop. I slipped in the back door and checked out the living room. No one was there. When you came out of the kitchen into the living room, to the right was what was supposed to be a formal dining room and was now Mom's teleworking office. That was where the girls were going to sleep. It was clear. I couldn't hear anyone, but Z had told me that they would be in the kitchen when I got home. Mom and Dad had gone to bed at ten as they always do when the next day was a workday. I walked around the edge of the living room and walked through what we called the 'back hallway' but was actually a narrow space between the stairs and the living room wall. I came to the stairs up to the second floor where Z and I had our bedrooms. I looked up and saw a wondrous sight.

Two girls were two-thirds up the flight of stairs, facing upwards. Both were wearing short shirts and thong panties that left most of their marvelous asses exposed.

Katharine said something upwards in a quiet voice that I couldn't make out. I guessed that Katharine was trying to keep my parents from hearing what she said.

I heard a voice that I didn't recognize answered back quietly, "Look, tonight's top secret." It was a struggle to make out the words. "Not a word of this is to get back to my mom and dad, right?"

I didn't catch Katharine's reply.

"Then I want to go braless," continued the quiet voice from above. "I've never gone braless around a guy before."

Katharine was wearing a pink nightshirt and white thong panties. Her long, straight brown hair reached almost to her waist. The other girl had to be Laurie as Giselle was short and a redhead, and this girl had short blond hair and was about Katharine's height. She was wearing a teal nightshirt and her thong panties were black with a white stripe on top. Her hand was on her hip, and I could see her bright pink nail polish. Z and my female classmates didn't wear nail polish, so I liked the novelty of seeing it.

Katharine said quite a bit to the girl upstairs. Laurie continued to stand quietly on the right side of the stairs, looking up with her hand on the banister. She and Katharine had very nice legs; smooth and firm. Her legs were a little thinner than Katharine's.

Katharine and the girl upstairs continued talking. I stopped paying attention to their conservation, somewhat because I could barely hear only half of it, but mostly because I was focused on the two gorgeous butts in front of me. I found this view of Katharine and Laurie incredibly hot. I really wanted to push both over, pull down their thongs, and fuck them right there. I had a major woodie.

I eventually decided I was pressing my luck and moved away from the stairs. I retraced my steps and slipped out the back door. I waited until 10:30 and re-entered. This time, I headed straight toward the kitchen. Z was standing guard in front of the doorway to the kitchen, and -- in a major surprise to me -- she was wearing a teal nightshirt. She hadn't...no, Laurie had to also be wearing a teal nightshirt.

Z said to me, "Go to the playroom," and then said to the kitchen, "Eli is here." I noticed her fingernails were bright pink. I moved to the playroom.

Katharine came out of the kitchen, followed by the other three girls. She led everyone to the playroom.

"Hi, Eli," Katharine said in her trademark half-sultry tone she used for greetings. In a normal tone, she said, "Let me introduce everyone." As Katharine introduced me to everyone, I couldn't help noticing that the five girls were all wearing the same style of nightshirt -- a V-neck top, a tapered middle, and a slightly flared bottom that ended a few inches below their crotch. All of the girls looked hot in the nightshirts. The color was different for each girl, so only Z had a teal nightshirt. All of the girls had their nails painted bright pink.

Katharine noticed me looking at the nightshirts. "I had a bunch of Victoria's Secret gift cards, so I decided to spend some of them. We went to Victoria's Secret this afternoon."

Several girls giggled. Valerie said unhappily, "I didn't get to go." By this time, I had placed Valerie as the girl upstairs that Katharine had been talking to.

"But you gave me your measurements," said Katharine, "so I got you your nightshirt." Katharine then chuckled at nothing obvious. Was she chuckling about buying all the girls thong panties as well?

Katharine saved me from thinking more about that by reciting the rules for tonight, and then she said to Z, "Tell us about Eli."

Z smiled at me as she moved next to me. My returning smile was a little forced as I was feeling guilty for the impure thoughts I had had about my sister ten minutes ago. But I hadn't known it was her!

"Eli is a sophomore pre-med student at our state's premier public university. With his grades so far, he's on the path to making it to med school. He spends most of his time studying. On Friday and Saturday nights, he and a few of his friends watch old action movies, making fun of the plot holes and the bad acting. When he was young, he wanted to be an astronaut. He started an astronomy club in high school and was president all four years. He is a dog person, and last year when we had to put our dog to sleep, he came home from school to be there and cried while he held Mr. Buttons in his arms that last time. When he has free time, he reads non-fiction or science fiction."

Z looked at Katharine, who said, "That should be enough. But you left out one thing -- Eli's unattached. He hasn't dated anyone this school year." Katharine looked at me. "Is there anything you don't want to be asked about?"

I thought for a moment. "Not really."

Z said, "Don't ask him about pre-med or how he likes his classes. He doesn't want to talk about school while he's on vacation."

Katharine nodded. She turned toward Z, and it was like some secret message went between them. Z stepped forward as Katharine said to the other girls, "Z will demonstrate what you should try to do in the first round." Katharine then said to me, "Stand in front of the pool table." I moved in front of the narrow end. Z moved to the other side of the pool table and turned to face me. I backed up to the other edge of the pool table. Katharine formed the girls into a line. The pool table provided a backdrop to our little stage, with the other girls facing us as our audience. Katharine was off to the right of the line, about halfway between the line and Z, allowing her to keep an eye on everyone. She said to Z, "Start."

"Hey, Eli," Z said in a warm, friendly tone. She looked me directly in the eye and smiled broadly. "Katharine and I were talking about going somewhere for Spring Break. Somewhere far from here. What's the farthest you've gone for a vacation?"

"Stop!", said Katharine. She said to the line of girls, "Z didn't just blurt out her conversation-starting question. She set it up so that asking it would seem natural. She also didn't ask about Eli's favorite vacation. Asking about what is your favorite something is not a good conversation starter as typically most people don't have a clear favorite. The farthest Eli has gone has a clear answer that Eli should know off the top of his head." Katharine looked back at me. "Continue as if I didn't interrupt you."

Now that Katharine had pointed out how good of a job Z had done with her conversation, I was impressed. I suspected I seriously underestimated the amount of skill it took to be a good flirter.

I faced Z again and got back into a conversational pose. "Orlando. We went to Disney World when I was six and when I was eleven."

"Do you remember much from the first trip?"

"Some." I laughed. "I mainly remember how annoying my little sister was. She always wanted to go to character meet-and-greets, and I wanted to go on the rides."

"What were the rides you went on?" Z wisely sidestepped my criticism of her.

I talked about the rides I had enjoyed the most when I was six. I didn't think about that Disney World trip very often, instead thinking of the trip when I was older. Z had a certain innocence as she talked to me like she had never been to Disney World before and my adventures there were something novel and exciting for her. She kept me pulling out memories.

Katharine suddenly said, "That's enough." She turned to the girls in line. "Does that give you an idea of what I'm asking you to do?" The girls all nodded their heads. "Let's go into the kitchen and brainstorm plans for you." Katharine turned to me. "Go play some pool. We'll be back in a little while."

* * * *

Once the girls were gone, I sat down in one of the straight-back chairs along the wall and read. The playroom felt unusually empty; it was not a room I had ever read in. It was a room for having fun in. Z and I had kept our toys in the playroom when we were kids. Z had had an elaborate mini-kitchen when she was a little girl. As we got older and stopped playing with toys, Dad bought a pool table. He and I had played a lot of pool this weekend. Sometimes Mom and/or Z would join in. Despite Katharine's suggestion, I didn't play pool now -- I didn't want the sound drawing Mom or Dad out of their bedroom.

Lots of laughter was coming from the kitchen. After ten or fifteen minutes, the girls came out with Katharine in the lead. She said to me, "Each girl will talk to you for five minutes. Let them drive the conversation. Let them ask the questions and discuss what they want to discuss. This is about them practicing flirting with you. And remember the rules."

Laurie stepped forward and moved to the far side of the pool table. She was short -- maybe 5'4" -- and had blond hair, a shade or two darker than Z's. Her nightshirt was a light purple, which didn't do much for her. She said, "Hey, Eli. There was something I always wondered about you. You took classes from your dad, right?"

"A class every year."

"You got great grades in those classes, right?"

"Yes."

As I was much taller than Laurie, I had to look down to talk to her. The V-neck of her nightshirt showed a lot of chest skin. She wasn't well-endowed, but it was like her tits were calling to me: Look at us! Check us out!

"I never heard anyone accuse your dad of favoring you. If anything, he was harder on you than anyone else. You earned those grades by working hard." No one had ever mentioned this to me. I had to admit it made me feel good. "What was it like to be taught by your dad?"

I talked about what it was like to be taught by my dad. Laurie talked about taking an intro science class from him and how she liked him as a teacher. We talked about his teaching style. The whole time, I kept thinking: Don't stare at her boobs. Don't stare at her boobs. Then, mercifully, time was up. A pleasant conversation. If it had happened at a party, I would have enjoyed it, but not enough that I'd seek to have another one-on-one conversation with her later.

Laurie joined the line and Giselle took the spot opposite of me. Her red hair tumbled down in curls onto her shoulders. She was very curvy, which the nightshirt brought out. Still, her face was her best feature, and her black nightshirt put the focus on that. She had a dimple in each cheek, lots of freckles, and looked 15 instead of 18. She had such an air of wholesome cuteness about her. She was quite short, a couple of inches shorter than Laurie, so I got a good look down into the V-cut of her nightshirt and enjoyed the view. Don't stare at her boobs. Don't stare at her boobs.

"Hi, Eli."

"Hi, Giselle."

"You know, I don't think I've ever talked with you before." Giselle seemed uncomfortable. Was she shy?

"I don't remember having talked with you, either."

I waited for Giselle to say the next thing. I wanted to fill the silence in the conversation, but I remembered that Katharine wanted me to let the girl drive the conversation.

Giselle asked timidly, "What was the breed of your dog?"

"He was a mutt. My parents got him at the pound. He was about the size of a German shepherd."

"We have two dogs. Dachshunds. They're lots of fun."

I was tempted to ask about her dogs, but I knew that wasn't my role. Giselle finally asked, "What was your favorite thing to do with your dog?"

"To take him with me when I went to look at the stars. My dad and I would go someplace well away from buildings, so there wouldn't be any light. He loved exploring new places."

Giselle smiled. "Did he bark and jump around?"

I laughed at the memory. "Oh, yes. And he would race around whatever field we were set up in, smelling this tree and that rock."

Giselle's eyes lit up. She was amazingly cute. She straightened her back, and her big tits seemed to swell. Don't stare at her boobs. Don't stare at her boobs. "Did you take him on hikes or long walks?"

She got me telling Mr. Buttons story after Mr. Buttons story. Then I started feeling my eyes getting wet. Soon, tears were streaming down my cheeks. I had to stop. "I'm sorry. I still miss Mr. Buttons."

Giselle took a few steps forward and hugged me. "It's okay. It's perfectly understandable that you'd still miss a dog that you loved."

Tears kept pouring down my face. I was embarrassed about crying in front of so many people. "It was his time. He was in such pain at the end. He was a great dog, but it's time for me to let him go."

Giselle continued hugging me, pressing her head into my chest. "But you should never let go of his memories. He's still alive in your heart, and he's still bringing you joy."

I patted Giselle lightly to express my thanks for her support. She held onto me, giving me time to stop crying. After a while, she looked up at me to see how I was doing. She smiled at me and asked, "Feeling better?"

"Yeah. I'm sorry I interrupted your flirting practice."

"Don't think anything of it." She hugged me harder, putting her head against my chest. I wrapped my arms around her back. "A guy being honestly emotional really appeals to me. If you went to the same college as me, I'd definitely be looking to get to know you better." Giselle leaned back to look up at me. "That, and you're good-looking, and several of my friends tell me you're a very nice guy." She smiled at me, which tore a hole through my heart. "I think I've done enough flirting for now."

Giselle moved back into line. Katharine wiggled her finger at me and said gently, almost mockingly, "Remember the rules. You aren't supposed to hug anyone."

I smiled at the ridiculousness of her comment. "Okay. I'll do better from now on."

Giselle called out, "I liked the hug!" The girls behind Katharine laughed.

I wiped my eyes with my shirt sleeve. I took a deep breath and said to Katharine, "I'm ready for Valerie."

Katharine said to Valerie, "You go."

Valerie moved opposite of me, doing a jump stop into place. She was tall, only two or three inches shorter than my six feet. The gray of her nightshirt suited her -- she was a big, tough girl. She had short dark brown hair. With me looking straight into her face, I hoped I wouldn't be tempted to look at her boobs. But she was definitely braless; her good-sized tits wobbled against the material of her nightshirt. And her nipples were sticking out like gumdrop candies. Was she cold? She might be that cold if we were in a meat locker. I was more distracted by her tits than Giselle's.

"Hey, Eli," she said confidently. "I hear you wanted to be an astronaut when you were little. Are you still thinking of doing it once you become a doctor?"

"I've looked into it. I'd love to be an astronaut, but I'll have a boatload of debt once I get out of residency."

"What kind of physical shape would you have to be in to become an astronaut?"

We talked about what it would take for me to qualify for astronaut training. She stood closer to me than the other two girls had; kind of on the edge of socially acceptable closeness. More enjoyable than talking with Laurie, but not as enjoyable as talking with Giselle.

Katharine ended my conversation with Valerie and moved to the other end of the pool table. "Hi, Eli."

I couldn't help smiling at Katharine. I liked her. "Hi, Katharine."

"I wanted to thank you for making the time to do this workshop. I'm sure you're crazy busy with your studies and probably brought a ton of homework home with you."

"Not a ton, but I do have homework this week."

Katharine moved closer to me. "It's kind of inspiring to me that somebody I've known for years, the son of one of my school teachers, is going to be a doctor someday. I'm sure you'll be a great doctor. I love how humble and grounded you are, even though you'll be making a lot of money in the not-too-distant future."

I hadn't been expecting this kind of praise. I looked down and shuffled my feet. "Thanks."

Katharine grabbed my upper arm and turned me toward the other girls. "That's how I typically flirt with a guy. I pump up his ego." Katharine let go of my arm and stepped forward. "The thing with that type of flirting is that I learned nothing about Eli. We all wear masks, and I played to Eli's mask as a pre-med student from my hometown. I stayed behind my mask the whole time. That leads to very shallow relationships. Which is fine for me, as I love shallow, disposable relationships." Katharine gestured toward Giselle. "But I don't think that's what you want." Giselle nodded. "So, what I'm trying to teach tonight is to use flirting techniques to get the guy to lower his defenses, and then to use conversational skills to get behind his mask." The girls nodded. "I've learned more about Eli during this round than I've learned in years of flirting with him." Katharine moved to her normal spot while beckoning Z to come forward. "Z will demonstrate what you're to try for in the next round."

Z moved into position. "You've told me that you went on a ski trip with some friends last Christmas break. Where did you go?"

I started talking about my ski trip with Tracie and some of her friends. As I considered a lot that happened on the trip to be personal, I was far less open this time. But Z was able to keep the conversation going. Z was more animated this turn as she listened and talked, giving a stronger impression that she enjoyed talking to me. When I talked about skiing with one of Tracie's friends for a few runs, Z said, "I like a guy who can make friends so quickly." When I talked about snow tubing, Z said, "I'd love to go tubing like that sometime." The way she said that sounded like it was a big hint for me to ask her tubing sometime. When I talked about us playing games in our rooms as we couldn't go to a bar, Z said, "I'd be fine on passing up the bar too but would have preferred a long walk through the snow." Again, it sounded like a hint to ask her to go for a long walk through the snow sometime.

It was weird talking to Z like this, as a potential date instead of as a sister. I started looking at Z that way. With her blue eyes and blond hair, she was just as pretty as Katharine and Giselle. She was an odd mix of shy innocence and Katharine's flirty brazenness. She was letting me know she wanted to go for a long walk at night sometimes with me, but, unlike Katherine, she didn't have any experience going for a long walk at night with a guy.

Katharine ended our conversation with a simple, "Thanks, Eli. You were quite the gentleman. We're going to the kitchen and talk things over. Stay here. When we come out again, you'll have the exact same conversations. Please try to act like you did the first time." Katharine turned toward the girls and shooed them toward the kitchen. She asked me over her shoulder, "Do you know what a gentleman is?" When I didn't answer, she added, "Someone who tries to not be obvious when he stares at a girl's boobs." All of the girls laughed. Katharine winked at me. I could feel my face get hot. I was sure I was bright red.