A Flirting Workshop with My Sister

* * * *

As I sat in the chair, I kept chuckling about Valerie - her innocent eagerness, her wanting to be bad now that she could do so without it getting back to her parents. Her conversations hadn't been very interesting, so I had no interest in her beyond making out. But making out was fun.

I had to admit that the flirting workshop so far was a lot more fun than I had thought it would be. I felt like I had gotten to know Giselle, Valerie, and Laurie much faster than I normally would, and I liked all three of them. I had flirted with Katharine a lot over the years, and she was taking that flirting to another level. I still couldn't believe that I had groped her ass and boob. She was coming on to me much more than she ever had before. But I had the feeling she was just yanking my chain. Maybe she was upping the level of flirting as a way of thanking me for going along so well with the flirting workshop?

But as much fun as the workshop had been, it was becoming repetitive. Hopefully not too many more rounds.

* * * *

The girls came out, and Laurie assumed the position. What she slipped into her conversation was that she wanted a guy who would do fun things with her like go to the movies and play party video games. Giselle was up and what she wanted was a guy who wants a long-term relationship where he spends a lot of time hanging out with her. I wasn't surprised. Valerie wanted a guy to have fun with while keeping their relationship secret from her parents. Valerie's "fun" to me had little in common with Laurie's "fun". The one big change in behavior was the girls did things with the hair as they talked to me; fluffing their hair, running their hands through the hair, tossing their hair, playing with the hair, chewing their hair.

When Valerie and I were talking, I went to grab her ass. She saw it coming and twisted slightly so I could get a better angle. She did her speech and then continued on. I peeked at the girls to see what they thought of us. I could see Z standing behind the rest of the girls with her arms crossed. She looked very unhappy.

When Valerie was done, Z didn't give a demonstration this time. The girls went back into the kitchen, and I closed my eyes and relaxed. I was worn down and wanted to regain my energy for the next round. I let my thoughts drift for a while, and they kept coming back to the image of Katharine and Z on the stairs. To get that off my mind, I considered the girls in the workshop. Laurie was nice but didn't excite me. Valerie made me feel guilty. Showing a sheltered virgin the joy of earthly pleasures was very appealing, but we had nothing in common besides the desire to make out madly, and I didn't want to be the guy who goes as far as he can with a girl and then leaves with no intention of seeing her again. I liked Giselle. I felt like she was the opposite of Katharine; someone who didn't have much of a mask. But I didn't see anything happening between us. I had the feeling that she was looking for strictly a long-term relationship, so she'd pass on me. She was more of a nice fantasy than a serious interest.

And then there was Katharine. My, oh my, Katharine. I had a major crush on her my senior year of high school. Her every visit to our house had been sweet torture. I had kept waiting for her to give me a sign that she was interested in me, that I wasn't just the guy she flirted with before she started studying with Z. But she never did. This evening reminded me why I had always been in lust with her. She was the same as she had always been - gorgeous with this immense presence. I was happy to spend time with her again. But I no longer had a crush on her. I thought about why. What I eventually came up with was Katharine hadn't changed, but I had. I was no longer a small-town boy enraptured with one of the prettiest girls in school. I was a pre-med major now. Pre-med was my universe. I spent almost all of my time in my pre-med classes, studying for my pre-med classes, or talking with my pre-med friends about our pre-med classes. Katharine wasn't a part of my pre-med universe, so she didn't fit into my life. Her beauty and presence didn't touch me anymore; there was now a distance between us that hadn't been there in high school. She was now akin to an actress on a movie screen; I admired her beauty and presence but knew it wasn't for me.

Also, she had said a couple of things that made it clear she wasn't the type of girl I wanted to date. Despite the years of us flirting, I didn't know much about her beyond she was an expert at pushing my buttons. Tonight, she had come across as so smart, so knowledgeable. Then I remembered Z telling me that if she were to date one of my friends, they'd be disappointed with her as they only saw what she wanted to show them and not the real her. Would Katharine keep her mask up if we were to date this week? Probably, I realized. Suddenly, dating Katharine was much less appealing. If anything were to happen between us, it'd be a shallow bit of frolicking. Still, it'd probably be damn awesome shallow frolicking.

How would this workshop change my relationship with Katharine? I saw her regularly because she was Z's best friend. I couldn't picture her acting significantly different than she always had. She'd return to being someone I enjoyed flirting with, to being my favorite sex fantasy, and to being someone I'd never seriously consider as a girlfriend.

What about Z? If she wasn't my sister, where would she fit in compared with the other girls? I had a more complete relationship with Z. Katharine had been totally right when she said that sex and cheerleading were important to me, but being my best friend was the most important thing to me. Z was already filling the female best friend role. We talked a lot about school and my friends. She was good friends with my best friends. She had all the traits I admired in a woman - attractive, smart, hardworking, and excelling in a difficult academic field. She spent enough time with pre-meds to understand the pre-med life and to talk the pre-med talk, but she wasn't feeling the pressures that pre-meds felt. She was enjoying excelling in her classes and shared that joy with me and my friends. And if she hit a little hiccup, she wouldn't crash and burn in Engineering. She'll be there for the distance. She's the one female I'd feel safe building my life around, even if it was a modest sibling relationship.

I was still shaken by how much I had wanted her when she was on the stairs. Had my subconscious known it was Z? Had I been lusting for my sister for a while, and because I could justify not recognizing her my mind went wild with sexual fantasies about her?

Would this workshop change my relationship with Z? I had been impressed by her performance. She had demonstrated a conversational agility I hadn't known she possessed. I hadn't looked to her for an interesting conversation, but I would now. This workshop would give us a special memory, an additional bond, and a pleasant secret to re-share. I could see us discussing it in the future when it was only the two of us, comparing things that just happened to what happened during the workshop. This workshop really opened my eyes to what an attractive woman Z was.

I really liked my sister. I was glad she spent a lot of time with me and my friends so far this year. I almost wished Z wasn't my sister.

* * * *

Katharine led the girls out, saying, "Last round. Each conversation will be ten minutes. Each girl will use both topics she discussed with you earlier and in general use everything they've learned tonight."

Discussing the same things over again didn't make for the most stimulating conversation, but it was interesting to see the improvement in their flirting. Surprisingly, Laurie was the best flirter of the three. Giselle was the one I wanted to date the most, primarily because of how cute and sexy she was. I didn't try to grope Valerie this time. I didn't think I could surprise her, and the recollection of the unhappy Z deterred me.

And then it was over. Katharine said, "Each girl would like to thank you, Eli."

The girls were in a line, so I stood in front of Laurie. She said, "Thanks Eli for a great evening." She gave me a brief, friendly hug. "I really enjoyed talking with you."

"I enjoyed talking with you too. It was good to get to know you."

I moved in front of Giselle. She hugged me right away. "Thanks for doing this. This did wonders for my confidence. And it was a blast."

"I had a blast talking with you." Giselle ended the hug and stepped back.

I moved in front of Valerie. She said, "My eighteenth birthday was two weeks ago, and this was the best birthday present ever." She hugged me and said quietly to me, "I'd love to see you some more this week."

"You were a lot of fun to talk with." Valerie stepped back into line.

I said to the three girls. "Thanks for being such pleasant company. This has been the most enjoyable evening I've had in a long, long time." I turned to Katharine, who had moved next to me. "And thanks for asking me to participate."

"Let me thank you for doing such a great job." Katharine kissed me, her warm lips pressing firmly against mine. My arms automatically went around her. After a few moments, she pushed her tongue against my lip and then gently into my mouth. I was too surprised and overwhelmed to do anything. Katharine pulled her tongue back, held the kiss for a second more, and stepped back, leaving me partially stunned. She smiled at me and said, "We're going to keep talking down here. Go up to bed."

I nodded, shook my head to clear it, and walked over to the stairs. I gave everyone a final wave goodbye and headed up.

Once in my room, I got naked. I grabbed some baby lotion and a tissue and started stroking my mostly hard cock. It quickly reached full attention and stroking it felt much better than normal. I thought over the things that happened tonight, and I came quickly. The thing I was thinking about as I came was Katharine and Z on the stairs.

* * * *

My alarm went off at seven the next morning. I could have slept later, but I had promised my parents I'd help make breakfast. I got dressed and headed downstairs.

When I moved off the stairs, I could see my parents cooking in the kitchen and the five girls slowly waking up in Mom's office. They were all dressed in nightshirts that were much longer, looser, and thicker than what they had worn last night. I decided to cut off Valerie from trying anymore to get me to ask her out. I walked over to where Valerie, Laurie, and Giselle were lying on the floor, got down on my haunches, and said, "Katharine asked me to participate in her workshop to make a special evening for Giselle. She didn't do it so I could hit on any of you. I feel like you all made yourselves vulnerable to me last night, and for me to try to go out with one of you would be taking advantage of that. So, I won't ask for anyone's phone number nor will I give out mine. Thanks again for a fantastic time."

I got up before they could react and joined my parents in the kitchen. They were cooking scrambled eggs and bacon. I took over the cooking, so they could eat. Once my parents finished eating, they took off. The girls came in and took over the dining room table. Valerie looked unhappy. Katharine gave me a sly grin and a wink. I served them eggs and bacon. I then cooked an omelet and ate it next to the stove. During that time, I'd occasionally make eye contact with one of the girls. They always smiled at me and returned to their conversation. The flirting workshop was already a happy secret; a pleasant memory that was never to be discussed.

This story was written by 8letters and published on Literotica

* * * *

At nine, I came down the stairs. Katharine was at the door, talking with Z. A quick check revealed she was the last girl to leave. Katharine gave me a quick wave, said goodbye to Z, and then was out the door.

I said to Z, "You don't have to go over to the Harringtons'. I'll take care of everything."

"No. I want to go."

"Okay. Change and we'll go."

We got in my car and drove over. I asked Z, "How much sleep did you get last night?"

"None. All of us girls talked for a while, and then Katharine and I talked after the rest went to sleep. I'll crash when we get back."

"What did everyone think of the workshop?"

"They loved it. Giselle was feeling lost at college, a small-town girl at a big school. Like me, she's having a tough time making friends. And then her long-time boyfriend dumped her. She was feeling down, and now she feels much better." I was glad to hear that. "Valerie was very disappointed when you announced you wouldn't date anyone. She had already talked with Giselle about providing cover when she spent time with you."

I wasn't too surprised by that. Had I made the right decision? I thought so.

"Last night, the other girls talked about what they are looking for in a boyfriend. What are you looking for?"

Z took a big breath. "I'm like Katharine in some ways but not in others. Katharine wants a boyfriend who'll let her do whatever she wants and who trusts her to make things okay. I'm very much like that. I feel like I'm growing a lot at college, and a large part of that is because Katharine talks me into doing things I'm uncomfortable doing. My social skills and self-confidence have improved dramatically. I want the freedom to keep doing new things, to change and grow."

"Okay."

"I can tell you're interested in Katharine. If you dated her, could you handle allowing her to do whatever she wants?"

I thought for a bit. "I like Katharine, but I don't see us dating. There isn't enough time for us to date now. When Dad gets off work Wednesday, we'll be spending the rest of our time home with family. That means I'd have at most two and a half days to be with Katharine. And then I'll be back at college with finals coming up soon."

"If you had a chance at dating someone like Katharine at college, could you handle allowing her to do whatever she wants?"

I frowned. "There's no one like Katharine. Everyone is unique, and she's more unique than most." I thought for a bit. "But I can see letting my girlfriend at college do whatever she wants to a certain degree. I spend so much of my time studying that she'll have to have a life of her own. But when it comes to the weekend, I'd expect to be her top priority, and she'd be mine."

Z nodded. "Katharine doesn't want a serious relationship. She's not looking to fall deeply in love or be heavily committed. When it stops being fun with a guy, she moves on to the next. I convinced her that when she got to college to slow down, date a few guys to figure out who she wants to commit to, and then try to make that relationship work. Now she's dating three guys at the same time while flirting with a few more."

I laughed. "She's repeatedly punching the 'dating three guys at once' square on her lifetime achievement card. Very impressive."

"I think she's much happier just dating. She likes having fun with lots of different guys. I'm the complete opposite of that. If I date a guy, I want us to fall quickly in love and to be totally committed to each other. Where are you on that scale?"

"I'm at the same end as you." Thinking of Katharine made me shake my head. "It's so surprising to me that you're best friends. I see you and Giselle as having more in common."

"When I was struggling, Katharine saw in me what I could be. No one else did. And she helped me become the person I want to be. We forged a bond over the last year that I'll never have with anyone else. I can tell Katharine anything, and she can tell me anything. No judgment, only support."

"Wow. That's great. I've never felt like that with any of my male friends." But that didn't answer my question. "But what do you have in common? What do you talk about?"

"Boys." Z laughed. "I've been raised to be a good girl. If I was best friends with Giselle, we'd have pleasant conversations about how our very proper relationships were going. But Katharine knows I have a bad girl streak in me. So, my talks with Katharine about boys are completely different from what I'd have with Giselle. Katharine is always telling me about what bad things she's doing with boys, and she's always pushing me to do crazy things."

"And you do the crazy things."

"Yeah. It's like when Katharine dares me to do it, I can't resist the dare." She thought for a moment. "Doing the crazy things makes me feel so alive. But Katharine has to dare me. If I were to do a crazy thing on my own, I'd just feel stupid." Z suddenly changed the topic. "Why not go out with Valerie? You don't have anything planned for the next few days, and she seemed totally up for a brief, hot fling."

"Because I'm looking for something long-term. I'm looking for something where I could be me. With Valerie, it'd be all about making out, and, as Katharine said, I'm looking much more for a best friend." I had another thought. "I think we'd both be disappointed if we dated. I don't see us having that much in common, and the date wouldn't live up to the magic of last night. This way, we'll always have what might have been. Same for Giselle and Laurie." I thought about Z and my friends. "I can see now why you don't want to date Dimitri, Rob, or Landon. You've had enough fun with them that there's a certain magic in those relationships, but it's so hard to have a happy romance when you're pre-med, so you'd be disappointed if you actually dated them."

Z's phone played its message-received music. Z picked it up and read the message. "It's from Katharine. Giselle is very glad you told Valerie you wouldn't date her as she was very uncomfortable about Valerie pressing her to provide cover."

"Okay. That's good. I liked Giselle, and I'd rather make her happy over Valerie. I was impressed at how she handled my crying over Mr. Buttons."

"Giselle is a super-nice person."

Z told me Giselle stories until we arrived at the Harringtons' house. They had a ten-foot fence around their big backyard and an eight-foot gate in their driveway. I pulled into their driveway, pushed the remote to make the gate open, and then drove around to the back and parked outside of their garage. We got out and walked around the corner to their covered porch, which was thirty feet wide and twenty feet deep. The right side of the porch had a door that led into the kitchen. The middle was patio furniture. On the left was a hot tub. To the left of the hot tub was a door to the master bedroom.

I had spent many an evening on this porch. Dr. Harrington's youngest son Rand was my age. We had been on lots of sports teams together when we were young. During those years, my family had regularly come over, and Dr. Harrington would grill us dinner while Rand and I had taken turns throwing a tennis ball for Bart to fetch. During my high school years, I had continued to visit regularly. Rand and I would talk about being pre-med majors and eventually doctors. Rand was now studying pre-med at a prestigious private university.

I said to Z, "Dr. Harrington is why I'm going to be a doctor."

"Did he say something that inspired you to be a doctor?"

I smirked. "Actually, he tried to talk me out of going pre-med. Mom arranged the talk. He told me that its long hours, insurance companies make your life hell, and the money isn't what people think because of all the debt racked up in getting through college and med school."

"So, what was it if it wasn't something he said?"

Z unlocked the kitchen door, and Bart came charging out. As Bart was twelve, his charge wasn't as fast as it used to be. He went straight to me, and I started petting him. "Who's the good boy? Who's the good boy?"

As I was petting Bart, Z went into the house. I'd spend the stay in the backyard with Bart as Z took care of everything in the house. I knew she'd disarm the alarm, mix some meds into Bart's dog food, set that down for him, and then go water some plants.