A Flirting Workshop with My Sister

* * * *

I thought about what Katharine had said while the girls talked in the kitchen. I felt like a big reason why I had burned out on hookups was that I could never drop my mask during them. After the weekend was over, we'd go back to being fellow students. I would have never cried over Mr. Buttons during a hookup for fear that the story would have been shared with every pre-med student. I couldn't even say which pre-med guys I didn't like because the girl I was hooking up with could be hooking up with them the next weekend.

I thought about my talk with Giselle and how she had torn a hole in my heart. I realized it was because I missed having a girlfriend that I was very close to, who'd tell me that everything's okay when I'm down. There were so many times when I was down, but I always hid that from everyone. So many times when I questioned if I wanted to keep doing pre-med, or if all the sacrifice would be worth it in the end. Z was the only person around whom I let my mask down, and then I let it down only so far.

* * * *

The second round was much like the first. Same order, same conversations. There were a lot of minor changes though. The girls complimented me more. When Laurie talked to me, she said, "I like guys with integrity" and "Guys who everyone respects really appeal to me." Giselle said something similar, "I much prefer to date someone who's a dog lover." When she said, "I'd love to go along when a guy takes his dog on a long walk," I was tempted to say, "I'll be taking Bart for a long walk tomorrow night." What Katharine taught them wasn't a straight out "I like you", but I as a guy couldn't help connecting the dots while giving the girl plausible deniability. If I rejected Laurie's advances to me (the likely outcome), there'd be no loss of face, as she never came right out and said she liked me.

Valerie started doing something similar. Again, she stood closer to me than the other girls and did little things to emphasize that she was braless. At one point, she said, "I'd like to go for long walks with a guy who's keeping in shape. Like you." She then twisted while lifting her nightshirt to show me a butt cheek. "I want to keep this firm."

I laughed, turned to Katharine, and said, "She's being so over the top that if we had been alone, I would have thought seriously about testing how firm her glute is."

Katharine made an unhappy face and then stepped forward. "Valerie, what I'm trying to teach here is how to use your conversation skills and your body language to grab a guy's attention. Once you have his attention, he's going to check out your physical assets." Katharine moved next to me and turned so she could talk to both Valerie and the other girls. "But this brings up an important point. A guy should never touch your breasts, butt, or crotch without your permission. There is nothing that you can wear, say, or do that makes it okay for him to do so. But guys will still do it. And when they do it, it's really important to take control of the situation immediately. Valerie, go back in line." Valerie moved back in line and Katharine moved to where she had been standing. "Eli, when I say what Valerie said, I want you to test how firm my glute is."

Holy shit! Katharine was asking me to squeeze her ass? Good god! How many guys in my high school had dreamed of doing that?

"I'd like to go for long walks with a guy like you who's keeping in shape." She did the same twisting and lifting of her nightshirt. "I want to keep this nice and firm."

I reached forward and gave her butt -- that I had lusted for mightily a little earlier -- a good squeeze.

Katharine grabbed my hand and pushed it away firmly while saying in an even tone, "Eli, I'm not ready to let you do that. Maybe someday when I know you better, but today is not that day. I'll let you know when I want you to do that." She didn't step back, but instead firmly stood her ground. "How did that make you feel?"

I thought for a moment about the impact of her words on me. "That I had done wrong; that I had overstepped. You still liked me, and if I did the smart thing and apologized, there was a chance you'd give me permission someday to do that."

"Great. That's what I'm hoping for." She turned to the girls. "And that's the response you should get. If the guy gets angry or starts blaming you for his actions, get out of there. If you think you can safely run out of the room, run. If you don't, do something like this." Katharine turned back to me. "Oh, Eli." Katharine moved closer to me. "Don't get angry." She suddenly jerked up her knee, stopping just short of my crotch. She turned back to the girls. "Do that and then get the hell out of there, and don't feel guilty about it. You're keeping him from doing anything worse." Katharine turned back to me. "Let's do that again."

Did Katharine just ask me to squeeze her ass again? Had I won the fucking lottery?

Katharine said her line, I grabbed a nice amount of ass, and then she pushed my hand away again while repeating her line. She turned to the girls and said, "Don't push the hand too hard or too far away. Push it just far enough away to make your point. Most of the gropes I get are not straight grabs like Eli did. The guy slides by me and gropes as he goes. Or he'll put his arm around my waist as a friendly side hug and then drop down for a squeeze. Sometimes I let gropes go, but I hate it when I do because I feel that encourages more gropes. When I do react, I try to make it not be a big deal; just me conversationally letting the guy know that he overstepped. Don't give the groper a chance to play the victim, which he will probably do if you overreact." Katharine turned to me. "Let's do the same thing, except this time grab my boob."

Jesus Christ! Was today my lucky day or what?

"Katharine, I've always found you so attractive." And I gave her tit a squeeze with my right hand.

Katharine smiled at me while grabbing my right wrist with both hands and bringing it down close to my side. "Eli, I'm glad you find me attractive, but I'm not ready for that step. Maybe some other day. I'll let you know when I am." Katharine turned to the girls and said, "If any guy does that to you, it's uncalled for, and he should permanently go on your Jerk list. But it's important to keep calm. Seize control of the situation, let him know what he did was inappropriate but don't do anything that will cause him to panic or overreact." Katharine took a step forward. "This is very important. As this is a safe space tonight, I'd suggest you let Eli touch you inappropriately during your next talk with him so you can practice how to react in such a situation. I can understand if you don't want to, but I feel like I should give you the opportunity."

Really? Katharine was trying to convince the girls to let me cop a feel?

Giselle said, "I've been groped enough times that I don't need the practice, but, Valerie and Laurie, what Katharine said is so important to learn, and I'd recommend you practice how to deal with this type of situation if you haven't before."

There was silence for a few moments, and then Laurie said, "I had something like that happen to me once, and I really mishandled it. I let the guy get away with it and afterward blamed myself. I'd like to practice taking control of such a situation."

Valerie said, "I'd be fine with practicing with Eli. I'd like to do our talk again, and we can do it then." She resumed her spot in front of the pool table.

"Eli, don't do it when Valerie is expecting it," said Katharine. "Catch her by surprise."

I nodded. I stepped out of my usual spot and said, "I'd like to make one thing clear - no kneeing me in the crotch. I don't want to be doing the rest of this workshop in falsetto."

The girls laughed as I returned to my usual position.

Valerie restarted our conversation, and I said what I had said before. About fifteen seconds before Valerie got to where she had shown me her glute, I reached out and squeezed her tit, which had been tempting me all evening by bouncing around in front of my face. Valerie froze for a few seconds, and then she grabbed my hand and pulled it away while saying something akin to what Katharine had said. And then she continued on with our conversation normally.

Valerie moved back in line, and Z moved opposite of me. I knew she'd demonstrate what the other girls were to try for the next round.

"Eli, I was thinking of watching a movie tomorrow. What movies have you seen recently, and what did you think of them?"

I started talking about the movies I had gone to see in the theater last summer. I didn't think the movies we had watched on movie night counted for what she was asking. As we talked, Z went into the full flirting mode she did with "her guys". She cocked her head cutely as she listened to me, she played with her hair, she touched me frequently as we talked, she even threw in a double entendre. I was feeling for the first time her ability to turn the minds of guys into mush. Even though I knew Z didn't mean it, even though Z was my sister and therefore off-limits, it was getting to me.

At some point, I had a horrible thought. Katharine had asked me to grope the girls to give them experience in handling being groped. She didn't mean for me to grope Z, did she? She hadn't asked Z if she wanted me to grope her or not. But Katharine hadn't asked the other girls either. They had responded, and Z hadn't. Z didn't want me to grope her, right? She was my sister, and I shouldn't grope her, right? But the more she flirted with me, the more I wanted to reach out and squeeze one of her tits.

Thankfully, Katharine put an end to Z's flirting. Katharine said to the girls, "I feel all of you made a lot of progress from the first round. Let's go in the kitchen and talk some more." As she herded the girls into the kitchen, Katharine threw me an over-the-shoulder wink and then swung her hips wildly as she finished her walk into the kitchen. Man, she knew how to press my buttons while keeping it fun.

* * * *

I looked up from my book to see Valerie enter the playroom. I stood up, pointed, and said, "The bathroom is over there."

"I came out here to talk to you. First off, this has been a lot of fun, and you've been great. I wanted to thank you for letting me know I had gone too far. My dad is the associate pastor at First Baptist. My parents have never let me have a chance to not walk the walk if you catch my drift. The only dates I've been on have been chaperoned group dates. No way could I have gone to Victoria's Secret with the rest of the girls. I had a boyfriend for six months, and we did almost nothing."

Valerie stepped right next to me and smiled at me. I was a little surprised but decided to see what happened. She gave me a short kiss on the lips, and then she leaned into me. My arms seemed to naturally wrap around her. She put her head on my shoulder. I had never hugged a girl this tall before.

Valerie said, "Okay, now we've done more than my boyfriend and I ever did." I expected Valerie to pull out of arms, but she kept her head on my shoulder. "Like I said, all my experience with boys has been in very controlled circumstances. Knowing that whatever I did tonight wouldn't get back to my parents, I decided to have a bunch of fun that I can't normally. And I went a little too wild."

Damn, she felt good in my arms. "Well, after tonight you'll have a better gauge of what you can and can't do."

"True. The biggest revelation tonight for me has been Katharine showing us how to handle being groped. I've always been told that I should always dress conservatively, or some guy will grab my butt, and I'll be traumatized. That if I flirted, some guy might grab my boobs, and I'd be scarred for life. Katharine saying that being groped is unpleasant but something that I can handle when it happens was a huge shock to me. It was also shocking to me that Giselle had been groped a lot. If there's anyone who's not led a guy on, it's Giselle. But it wasn't this horrible, life-shattering experience for her either."

For someone without a lot of experience, she certainly knew how to make an impression on a guy. Her unbounded tits were pressed firmly into my chest. For like the hundredth time tonight, I was hard. "I know this will sound crazy, but I want you to grope me every time we have a conversation. Squeeze my butt. Grab both of my boobs. Catch me by surprise. I want you to help me overcome my fear of being groped. Because if I don't overcome that fear, I'll never put to use what Katharine is teaching us." Valerie pulled out of my arms, took a step back, and looked me in the eye. "Will you do that for me?"

It would be tough to say no to almost any request. But to grope her? "Sure."

"Thanks. I'll tell everyone what I told you." Valerie turned and walked toward the kitchen. She stopped and turned back toward me. "Besides, I like you groping me." And then she walked back into the kitchen.

* * * *

The third round started like the first round. This time, Laurie asked me about Mr. Buttons. Laurie's family had a rescue greyhound, whom Laurie missed a lot while at college. We alternated telling dog stories, so I had time to recover my composure after each Mr. Buttons story. She seemed on much surer footing talking about dogs. The main difference this time was her touching me with her finger every so often to get my attention or reinforce her point. I was enjoying this conversation so much more that I hated to interrupt it by groping her. I went ahead and grabbed her tit as gently as I could. It took her a moment to react. "Eli, we're friends," she said as she took my hand. She sounded very disappointed in me. "That's not something a friend should do. You've really hurt my feelings. Please never do that again. But we're still friends." I felt terrible for what I had done. She resumed the conversation, but I was rattled.

When Katharine called time, I said, "I'm sorry, Laurie. I didn't know it'd bother you that much."

"Oh, don't worry about it," Laurie said, smiling at me. "This time didn't bother me. It was the first time that bothered me. I didn't say anything that time. It feels good to have said something this time."

Giselle moved opposite of me. Giselle asked me about the difference between fantasy and science fiction. She had read The Chronicles of Narnia and The Lord of the Rings series. Her knowledge of science fiction was basically Star Wars. I explained what I thought the difference was between fantasy and science fiction, and the type of science fiction I liked. She was much more comfortable this time initiating and controlling the conversation. It was still a huge battle for me to not stare at her tits. It was a good conversation. When she said, "I like spending an evening with my guy reading on the couch," I wanted to volunteer to come over to her house with my book the next night. Would I talk to her again after tonight?

Then it was Valerie's turn. "Hi, Eli."

I felt she had cheated by getting a bonus flirting session while everyone else was in the kitchen. I decided to make this one a challenge. "Not right now, Valerie." I put my hands to my head. "I've got so much homework to do."

A confused look came over Valerie's face. She kept on her script. "I wanted to tell you how much--"

"I don't want to talk. I'm buried right now. I've got three tests when I get back to school."

Valerie stood there with her mouth open. She turned to Katharine, who leaped into action. "I'm sorry to hear that. You're really tense, right?"

I watched Katharine grab one of the straight-back chairs. I said, "Yeah. I've got so much homework to do." I couldn't keep up my conversation. Katharine put the chair in front of me so that it faced me. What was she up to?

"Sit down for a minute. Let me see what I can do about that tension."

I sat down on the chair facing its back with the girls beyond. As soon as I sat down, Katharine began kneading my back muscles. "Oh, I can feel that tension." She pressed a couple of spots, and relief flowed through my back. I guessed that reading my book hunched over had caused my back to stiffen. Katharine's fingers were like magic; they seemed to know where every stiff spot was and just the right amount of pressure to relax it.

Katharine said to the girls, "When you go to talk to a guy, you should have a script of what to say in your head. But pay attention to how he reacts. When you're flirting, the message you're trying to deliver is that you will meet all his needs if he can win your heart." Katharine's fingers continued to work their magic. I could feel myself getting floppy. "What I've been teaching you is how to be his cheerleader. Once you've got his attention, it's easy to convince him that you're his sex goddess - Giselle asked me to not teach about that. But sometimes, what the guy wants is a mother. Some guys, if you tell him that you'll give him a massage like this every time he comes home, and then you'll serve him a home-cooked meal, he's thinking about marriage." The girls laughed. "It's important to figure out quickly what needs are most important to him. For Eli, I think that while sex and cheerleading are important, being his best friend would be the most important thing." My jaw dropped. How did she figure that out? And it was right on the money. "I'm a rotten best friend and a terrible mother, so I know to put off guys who are looking for those two things, even if they think I'm the woman of their dreams." Katharine gave my shoulders a final squeeze. "Feel better?"

"I do. Thanks."

"Now, let Valerie practice what she's learned."

I stood up and moved into position. Valerie's nipples were still poking out proudly. She said, "As I was saying, I've always admired your T-shirt collection." Half of my t-shirts had astronomy stuff on them, and the other half were from places I had been. I was wearing a black shirt with a drawing of Saturn on it and Saturn facts beneath the drawing. I talked about my shirt and other shirts I particularly liked. I had the suspicion that Valerie hadn't known me from Adam in high school, so hadn't admired my T-shirt collection, but she was faking it very well.

At one point, I said, "I like your nightshirt. The material is attractive and looks comfortable." I pointed at her chest. "What's that?"

Valerie looked down at her shirt. I brought both my hands up and went for her tits. With both thumbs, I played with her big, protruding nipples that had been driving me nuts all night. Valerie grabbed my hands and pushed them down while giving her little speech. When she was done, she gave me a big grin. Once again, I was hard. Valerie resumed her conversation, and, eventually, Katharine said, "Stop".

Z came out to demonstrate for the next round. As Z had seemed to go all out last time, I wondered what she'd do this time. This time, Z asked me about good restaurants close to campus. She kept the flirting down to the level of the second round, but this time she told me what she was looking for in dates or a relationship as she flirted with me. "When I'm out on a date, I prefer eating somewhere fun instead of fancy." "Once I have a boyfriend, I'd let him pick the restaurant we'd go to." "I like to share meals on a date, so I like that they have several items that would appeal to both me and the guy I'm with." "I'm the type of girl who likes to pay her share when we go out, which would be a good thing at a restaurant that expensive."

When Z was done, Katharine started herding the girls toward the kitchen. Valerie was the last one to move. She caught my eye and then puffed out her chest, flaunting her still-hard nipples. She gave me a grin and walked toward the kitchen. Again, Katharine gave me an over-the-shoulder wink just before she disappeared. I picked up my book, but I was in no mood to read.