Study Buddy Pt. 04

"Look, I still care about you. I want you to get your relationship with Brian working better. That's still part of the win win win that we agreed to. Amy said she was surprised that I was still trying to help instead of running away. I guess I'm still trying to help. If it gets weird we can make a different decision."

She had to go so she could be home for Heather. My head was spinning from our conversation. I decided to call monk.

I explained things and tried to explain my feelings. He listened carefully then said something profound.

"Rob, you've always been different. The way you fall for girls is not like other guys our age. Now you have older women falling out of trees wanting to be with you. If you do something like this it has to be on your terms. You're not in it just for sex. You need more from them. You can't give yourself to them without there being an emotional connection and some commitment. I'm not saying you need to marry them, but don't sacrifice your integrity for sex. You'll feel cheap. It'll make you miserable. You'll hate yourself and them after. Ok?"

"Thanks. That really hits me deeply. I appreciate it."

I was really knocked on my ass by his statement. How the hell did he know me so well? I had a lot to think about.

Sandy and I caught up after class on Friday.

"Brian and I met with Amy last evening. Surprisingly, he is pretty ok with you babysitting. He remembered how you treated Heather before. Amy told him that you would be a good reminder to him that he needed to meet my needs. She also told him how amazing it was that you ended the experiment the way you did, that you had kept your integrity and you cared about his wife as much as he did. Brian cried. He said that it embarrassed him that you did a better job of caring for me than he did. I know it really hurt him to admit that. It was really beautiful. So can you babysit tomorrow at 6? And if you and Heather get along well, would you be willing to do it overnight?" Sandy asked hopefully.

"Tomorrow for sure. I'm open to the other, but let's not rush, ok?"

"Cool. Now I have other news. Amy is absolutely into you. She admitted to getting turned on and when she met you she was really blown away. Would you consider meeting her to explore possibilities?" She asked.

"I have thought about it. You know me. I have emotional conditions that have to be met. I've realized that I'm really not interested in a purely physical relationship. I don't think I need the deep connection that you and I formed, but I think I need the possibility of that depth. What made our physical relationship potent was the depth of trust and the sometimes unspoken, unrecognized desire we had to be coupled, mated, permanent. Does that make sense?" I shared.

"Yes," she gasped, "it makes me horny just to hear you say it."

"That's exactly what I mean. Without that, I'm not sure I can be with someone without it feeling cheap and ultimately hating myself. You've taught me a lot. But I have learned more about what makes me tick than either of us planned on. Do you think Amy would be up for that, to meet my emotional conditions?"

"Honestly, I don't know. If she is anything like me, that will make you more attractive, almost irresistible. But she may not be open to that. You'll have to talk to her," she shared.

She handed me Amy's business card.

"It's funny. She said that my personality was too intense for girls my age, but that it was like catnip for you and even her. I guess I'll have to find out." I said, "I guess I'll see you tomorrow at 6."

"Yeah. Hey I just thought of something. It's like a cliche that the husband fantasizes about fucking the teenage babysitter. We won't have that problem. The wife on the other hand," she said with a wicked smile.

"Has already had the best role play sex in the history of the universe with the babysitter. Now go and get ready to fuck Brian into the mattress," I teased.

"You're no fun. But you are totally my best friend. I can trust you to keep me straight with Brian. Thanks for that," She was crying so I gave her a hug. It felt really good.

The next day I was nervous about babysitting. I had never actually done it before. I called Michelle and asked her if she could give me some tips. She invited me over to talk about it.

"So who are you sitting for and how old is the kid?" she asked.

"Remember I told you about the older married friend I was infatuated with? It's her six year old daughter."

"Seriously, are you still infatuated with her?" She asked

"No. Things got seriously out of hand but now we're just friends. She needs to get with her husband, he's been neglecting her. I'm just helping out."

"Did you... And her..," She made a gesture by sticking one index finger through a circle made by fingers on the other hand.

"I need you to keep this confidential, ok. But yes."

"And now you're going to meet her family?" Her eyes were wide.

"I met them before. Her husband gave her permission to... you know. Their daughter is precocious."

"So you and her... And he was ok with it... Wow. And now you're what, like her side piece... And babysitter? That's seriously fucked up," She was shocked.

"No. She wanted to help me with my Carol problem. She did. But our thing is over, but she and Brian realized they had issues that they had to work through and so I'm helping them. As a friend of the family."

"Ok. Not really buying it, but here's what you need to know. Find out what games she likes to play. Keep her mind occupied. Run around outside so she gets tired and read to her at bed time. She's gonna ask you a million questions cuz you're new. Call me if you have a problem. I'm doing homework tonight." She was a good friend.

"Thanks, that was super helpful."

"Ok, now that's out of the way. I have some serious questions. I assume that you are no longer a virgin?" She asked.

"That is accurate."

"How deep were your feelings for her? I know you, so don't fucking lie," She looked into my eyes.

"It was intense. On both sides. I had to stop it. I wanted forever. That was not our agreement."

"Holy shit. How many times were you together?"

"Three. Dinner dates and then after."

"You got to forever in three dates? God, Rob. How was the sex?"

"Michelle, it was incredible, but only because of the depth of trust and emotional connection. On our first date it was just teasing, foreplay and oral. But it was so intimate and loving that I can't describe. I loved exploring her body and making her come with my mouth. I loved holding her and caressing her and falling asleep in her arms and waking up together and sharing together. It wasn't just physical," I explained.

"That's one hell of a first date. When did you lose your virginity?"

"Second date. She showed me basic positions. Missionary, ankles on shoulders, girl on top, doggie. She had seven orgasms."

Michelle's eyes were wide. I could see her nipples poking through her top.

"Seven? How many did you have?" Her voice was different, lower, husky.

"Four. Plus one in the shower. Yeah."

"I'm almost afraid to ask about your third date," She said

I told her in very gory details about our third date. I told her all the things we said to each other. I told her how hard it was for me to play the dominant role for Sandy to make her fantasy happen. Then I told her how after I realized that my feelings for her had gotten too deep so I stopped our relationship.

"Rob. That's amazing. So dirty and sexy. I have zero feelings for you, but my nipples are hard and my pussy is completely wet right now. I'm gonna grab my vibrator as soon as you leave. I can't believe you wanted to stop."

"I didn't want to, but I wanted her forever and that simply wasn't an option. So now we're just friends. Which is really cool. We can tell each other anything."

"And your Carol problem? Solved?"

"I think so. But I know what I want more now. Not sure Carol would have worked. I think that her teasing me while going out with someone else was an indication that she wasn't ready for the kind of connection I was looking for. Make sense?"

"Totally. So what now?" She asked.

"I have one possibility. I think it's a long shot, but I can easily wait for what I want. I'm in no hurry."

"You seem really happy. Confident. Like you're the same Rob, but different. It's really cool. I'm happy for you. You deserved better than the way Carol treated you. I'm glad you figured that out."

"Thanks. And thanks for the babysitting tips."

I went back to my room and showered and got ready to go to Sandy's.

I got to the house about ten minutes early and rang the bell. Brian answered with a smile and invited me in.

"Sandy will be ready in a few and will go over stuff with you for Heather. Did you really tell her to fuck me into the mattress yesterday?" He asked.

"Yeah why?"

"Nothing, just thanks is all. I know this is weird. But I really appreciate you, ya know."

"You guys have really helped me. I'm happy to return the favor. You both took a huge risk. Shit, it almost blew up. But now I hope things are good. I know they are for me. I hope you two can really relax and enjoy each other tonight. I'll hold the fort," I shared.

We high fived. I knew things were going to be ok.

Sandy walked in and asked, "what was that all about?"

"Just guy stuff," I responded. Brian smiled.

She walked me though dinner and bedtime for Heather and said they would probably be very late so I could crash in the spare bedroom. She walked me down to the family room where Heather was watching TV. They said goodbye to us and left.

Heather and I had a good time. We played Sorry and Connect Four. We ate the dinner Sandy had prepared. We played outside until it started to get dark. Then we watched TV for a while until it was Heather's bed time. As she got in her pajamas she wanted to talk.

"You're mommy's Saturday friend, but mommy said you're going to be my babysitter now. That her and daddy are going to go out more," She said

"I think that is true," I said.

"Daddy was sad. He and mommy went to see a counselor. Is something wrong?" She asked.

"Do you ever have a bad habit, like sucking your thumb or picking your nose?" I asked.

She nodded.

"Sometimes mommy and daddy have bad habits in how they treat each other. They needed to have a counselor help them break the bad habits. Now they are going out with each other. That's a good habit that will make them happy. Does that make sense?"

"I think so. Will you lie in my bed and read to me like daddy does?"

I think I read three books before she finally fell asleep. I went back out to watch TV. I fell asleep on the couch. At midnight I got up and went to the spare room, took my shoes off and laid down.

I was awakened with a soft kiss on my cheek.

"We're finally home. I had a great time. I'm so happy. Thanks for watching Heather. Did she give you any trouble?"

I sat up and started to put my shoes on. I told her no, then I told her about the bedtime conversation.

"You handled that well. I told you you'd make a good daddy."

We walked to the front of the house. Brian was there. He looked exhausted. I gave him a high five.

"Way to go you two!" I said as I walked through the front door. It was six in the morning.

On Monday after class I hung out with Sandy. She was still happy from her date.

"You seem really happy. I gather things really went well Saturday," I said

"Rob, I feel wanted and desired by Brian like I haven't felt since Heather was born. I didn't realize how far we let things slip. I'm really hopeful that we have righted the ship. So yeah. Things are great. Have you called Amy yet?"

"Not yet. Why?" I asked.

"Nothing. I just want you to have something, I guess."

"I'll call her, but honestly I do have something. I have myself, in a way I never really have before. And you did that for me. So don't worry. I'm better than I've been in a long time."

We talked for a while. After we parted company I called Amy.

"Amy, this is Rob. Are you up for having coffee with me sometime this week?"

"Of course. I really didn't think you'd call me. I am pleasantly surprised. Can you meet tomorrow at 4 in the afternoon?" She asked.

"Sure. Does Helmut's Alpine kitchen work?"

"Yeah. I love that place. See you then." She said as she rang off.

As I pulled into the parking lot a thought came unbidden into my mind. This was the first time that I felt like I was meeting a girl on my own terms. I knew there would be no room for playing games. Either it would work and go forward or we would both walk away. Is this the way adults start relationships? I felt really good.

I was seated in a booth with a view of the entrance. Amy walked in and I waved her over. As she sat down I looked at her for the first time as a potential mate. She was beautiful. Blond hair, blue eyes, full lips, she was not as tall as Sandy, but she was curvy and sexy in a different way. She looked like she was in her early thirties.

"Hi Amy, I'm glad we could do this. How has your day gone so far?"

"It's been busy. Non-stop actually, so I'm glad to have a break."

The waitress arrived with a pot of coffee and menus. I poured a cup for each of us and sat back.

She seemed a little nervous.

"Amy I'm gonna get right to the point," I said, "Sandy told me that you were into me and that I should call you. I'm telling you now that I'm interested in you and want to see if we can have something together. I find you attractive. You're beautiful, smart, powerful and sexy. The thing is I'm not really interested in something primarily physical. I've learned from my time with Sandy that it's the trust and the emotional connection that creates the passion, at least for me.

What I'd like to do is spend time with you. Get to know you. Learn to care for you as a person before there is any thought of the physical component of a relationship. I don't think I am ready to think of a forever partner, even though that is where my heart went with Sandy. I want to learn to be for you, like I was for Sandy, but in a more controlled and responsible way.

Would you consider exploring these possibilities with me as a friend and maybe a lover?"

"Wow. Talk about laying your cards on the table. Let me be equally candid. I'm definitely into you. Even more now after what you said. It's like you have emerged from your ordeal with Sandy as an even more intense but much more confident and powerful man. I was very turned on during our counseling session, to the point where I made some very unprofessional comments. Surprisingly you handled those without reacting which made me curious. I've talked with Sandy about my attraction to you. It's not purely physical, but you are gorgeous. I desperately want the emotional connection too, but it scares me.

Here's what I need to confess. I'm probably older than you think, I'm 42. My son is a year older than you. I'm damaged goods. I'm still struggling with issues after my divorce. You'll see it as soon as we start talking. I'm afraid that you won't be able to handle it. Trust is going to be hard for me.

If you're willing to put up with my baggage then we might be able to have something that isn't purely physical. I'm willing to give it a shot if you are," She said.

"Cool. Listening to you, I realized that I'm attracted to your brokenness, not afraid of it. It means that there is more I can give you if I figure out how. I don't really care about your age. Amy, I'm still learning who I really am. I think I'd really like to give it a shot."

"So what do we do next?" She asked...