A Well-Lived Life 2 - Book 5 - Michelle - Cover

A Well-Lived Life 2 - Book 5 - Michelle

Copyright © 2015-2023 Penguintopia Productions

Chapter 36: Jill and Keisha

Coming of Age Sex Story: Chapter 36: Jill and Keisha - This is the continuation of the story told in "A Well-Lived Life 2", Book 4. If you haven't read the entire 10 book "A Well-Lived Life" and the first four books of "A Well-Lived Life 2" you'll have some difficulty following the story. This is a dialog driven story. The author was voted 'Author of the Year' and 'Best New Author' in the 2015 Clitorides Awards, and 'Author of the Year' in 2017.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Workplace   Polygamy/Polyamory   First   Slow  

December 19, 1991, Chicago, Illinois

“What time will you be in?” Elyse smirked.

“By noon. Nobody is supposed to be here before then.”

“Have fun!”

“Have a good morning at work!”

She left and I went to find Kara who didn’t teach on Thursday mornings.

“Be careful, Snuggle Bear. She could change her mind.”

“I will. Are you grading finals today?”

“No, lab notebooks. Finals are tomorrow for my Freshman chemistry class. Where are you going to be?”

“Probably one of the guest rooms,” I said. “I don’t want to advertise to the kids that she’s here.”

“But Keisha is coming over on Saturday evening.”

“Yes. We’ll work it out. That’s when she could get away. She said she had a date.”

“That is true!” Kara giggled. “But I bet her parents wouldn’t approve!”

“Neither did your dad!” I grinned.

“Yes, well, I had different ideas!”

“No kidding!”

I wasn’t surprised when Jill showed up nearly ten minutes early, nervously excited. She was wearing tight blue jeans, a parka, scarf, heavy mittens and a wool cap.

“It’s cold!” she said, shivering.

“Come in!” I offered and helped her remove her winter outerwear.

“Can I get you some hot chocolate?” I asked.

“Yes!”

We went to the kitchen and I fixed hot chocolate for both of us. I decided we’d start in the ‘Indian’ room. Kara was in the study sitting at my desk to grade papers, instead of the ‘Indian’ room where she usually worked. I shut the door behind us and turned on some music.

“Here?” she asked.

“I figured we’d drink our hot chocolate. But it’s up to you. A bed or here. Whatever you want.”

“I’m not sure. I’ve never done it before!”

I smiled, “I know. Will you tell me what you want to do?”

“You know, the usual stuff!” she giggled, then sipped her chocolate.

“I assume you’ve had sex ed,” I said.

“Duh!” Jill said with a small laugh. “Of course! And girls talk, too. So like I know about stuff.”

“Good! But it’s better if we talk about it first. That way there are no surprises.”

“Uhm, sure, I guess,” she said, nervously sipping from her mug.

I waited to see what she would do or say. After a moment, I could tell she was trying to screw up her courage. She sipped her hot chocolate a few times.

“I, uh, want you to, uhm, use your mouth. And then, you know, put your thing in me.”

“I’d love to do that!” I smiled.

“If you, uhm, er, want, I could suck on you.”

“I’d like that too!”

More nervous sips of from her mug.

“Two of my friends said it hurt really bad, but one other one said it didn’t.”

“Were they seventeen? Or younger?” I asked.

“The one who said it didn’t hurt was seventeen. The other two were fourteen and fifteen. Does that matter?”

“It can. But don’t worry about it! I promise to make you feel REALLY good!”

“Like when you kissed me?” she sighed.

“Yes. Only way better!”

“What do I do?” she said, almost in a whisper, into her mug.

“Put your mug down, and come sit in my lap,” I said.

Jill set her mug on the low table and came to sit in my lap. I helped her snuggle with her head on my shoulder.

“Just relax.”

I gently ran my hands over her back and her firm butt and she sighed deeply. I slid a hand to her hip, then up her side, ending with my palm cupping her soft breast through her fuzzy sweater and bra. She lifted her head and looked me deep in the eyes, then leaned forward to kiss me. This time, her full lips parted and her tongue met mine, and we began the slow, sensual journey that had but one destination. I took my time working towards that destination, and it was nearly an hour, and two orgasms from my tongue, before I was naked, kneeling between her legs, with my glans against her labia.

“Please,” she begged, “I’m ready!”

I pressed forward, meeting only the slightest resistance, burying myself in her tight confines.

“Ungh!” she groaned.

I leaned down and kissed her, letting her taste her tangy juices that coated my lips and face. I lowered my body onto hers and she instinctively wrapped her arms and legs around me.

“You OK?” I asked.

“It didn’t hurt!” she whispered. “Make me feel like you did before!”

I began with gentle thrusts, which she tentatively met by flexing her hips, and she quickly understood the rhythm.

“Oh God,” she gasped. “Please! Please!”

“Please what,” I whispered.

“Make me feel good, Mr. Adams!” she gasped.

There was something undeniably erotic and sexy about the babysitter calling me that, and I wasn’t about to correct her!

“You can use the words I taught you,” I grunted.

“Make me cum, Mr. Adams!” she gasped. “Fuck me, Mr. Adams!”

I almost came as those words reached my ears. I had her very close now and she was alternating gasping and begging.

“Fuck me, Mr. Adams!” Gasp. “Make me cum!” Gasp. “Fuck me, Mr. Adams!” Gasp.

The orgasm she had seemed to cause her to short circuit. Her liquid brown eyes became blank, her body tensed and then shook hard, and she groaned loudly into my mouth as I French kissed her deeply. She was on autopilot at that point, humping hard against me as the spasms of her orgasm massaged my dick. When the orgasm passed, she relaxed, not quite limp, but her eyes were closed. Her hips moved rhythmically with mine and two minutes later she steeled herself again, and had another crushing orgasm. During the third one, I pushed deeply inside her and groaned into her mouth as my own orgasm overtook me.

I simply lay still, my head on one of the floor pillows next to hers, panting and recovering. When I began to deflate, I pulled out, rolled on my back, and pulled Jill to me.

“Are you doing OK?” I asked about ten minutes later.

“Oh God! Yes! Can we do it again?”

“Yes, if you want to.”

“Do you want me to suck on you?” she whispered.

“Only if you want to,” I said.

“You made me feel good with your mouth! I want to do the same thing! Is it OK, Mr. Adams?”

I groaned, “Yes, it’s OK.”

“Uh, what do I do when you cum?”

“It’s up to you,” I said.

“I, uhm, don’t know.”

“I’ll tell you when it’s going to happen and then you can stop and I can fuck you and cum, or you can let me cum in your mouth. You decide.”

She slid down and grasped me with her hand. I propped myself on my elbows and watched as she tentatively licked me, then opened those fantastic, full, ruby lips and began sucking on my glans. I became rock-hard immediately and she experimented with licking, and sucking me.

“Am I doing it right, Mr. Adams?” she giggled.

“Oh, yes,” I sighed.

She smiled and took me back into her mouth. I marveled at those lips that encased my shaft and enjoyed the tongue that bathed my glans. She began bobbing and the pressure grew to the point where I was getting very close.

“Jill, I’m going to cum soon,” I gasped.

She released me.

“I want you to cum in my mouth, Mr. Adams!” she whispered.

She took me immediately back in her mouth, which was a good thing, because I groaned and exploded almost immediately. She choked a bit as the first and second spurts filled her mouth. She reflex-swallowed just as the third spurt started, and then swallowed again after each remaining spurt. She kept sucking and licking until she was sure I was done.

“Did I do good?” she asked.

I pulled her up and fiercely kissed her, my tongue probing deep into her mouth. We kissed for a couple of minutes, before I pulled her into my usual cuddle position.

“You did fantastic,” I said. “How come you’re calling me ‘Mr. Adams’?”

“‘Cause it’s naughty!” she giggled. “You know, the babysitter seducing the dad!”

I chuckled. “What made you think of that?”

“A movie I saw! I thought of you when I watched it!”

“When was this?”

“Right after the first time I babysat! And you liked it? I mean the sex?”

“It was fantastic! As soon as I’m ready, I want to do it again, if you do.”

“Yes!” she giggled. “How many more times?”

“Well, I have to be in the office at noon, so two, I think. That gives us time to shower. I can’t have you going home smelling like sex!”

“Shower? Like together?”

“Yes.”

“Oh God, yes!” she sighed, then giggled. “Mr. Adams!”

We lay together for about twenty minutes before I knew I was ready to go again.

“I’m ready if you are,” I said.

“Yes!”

“What do you want?”

“Lick me and make me cum, Mr. Adams! Then fuck me!”

I chuckled and complied. The third and final time, she was on top, and rode me to our mutual orgasms. When we finished, I helped her wrap a towel around her, and I did the same, and we went to the basement. The small shower was perfect, because our bodies were mostly pressed together the entire time. I helped her wash and she helped me, then we dried off and went back upstairs. We dressed and I lit some incense, and then I walked her to the front door. I helped her into her winter gear, and as I was about to open the door she grabbed me and gave me a tremendous French kiss.

“Could we do this again sometime?” she asked quietly.

“You would have to ask Doctor Jessica and Kara,” I said. “But like we talked about, I can’t be your boyfriend.”

“I know, but I like being the naughty babysitter fucking the dad!” she giggled.

“I’ve created a monster,” I chuckled. “You do need to find a guy your age.”

“I promise! But I think I need one more lesson to make sure I know how to do it right!”

“Not nervous anymore?” I grinned.

“Are you kidding? No way, Mr. Adams! I’d do this all day and all night with you if you want!”

I gave her a quick kiss, we hugged, and she went on her way. I went back to the Indian room and cleaned up, taking the towels and blankets to the laundry.

“Have fun?” Kara asked, coming into the kitchen.

“She’s hooked,” I chuckled.

“Another A+ performance!”

“She might come ask you and Jessica for one more time. She really got off on the idea of being the naughty babysitter fucking the dad!”

Kara laughed, “That nervous little girl?”

“Not anymore!” I grinned.

“And let me guess, you loved the idea of fucking the babysitter?”

“I almost came instantly when she begged ‘Fuck me, Mr. Adams’!”

“Hmm. Sounds like we need to do some more role playing! Like with the hair dye. Maybe we do that again and pretend to be young girls for you!”

“Not too young, Kara,” I said.

“No, of course not. Sixteen or seventeen. We could do that, I think. You know, the girl who flirts with the older guy and lets him seduce her. I bet it would be fun!”

“Maybe! But now I need to get to the office. Everyone will start arriving soon. I’ll be home about 5:00pm to get ready for dinner. Jess will come home about then. She got someone to cover the last hour of her shift. Remember, she took her car today.”

“Yes! See you at 5:00pm!”

I kissed Kara and headed to the office. I had only been sitting down for a few minutes when my dad came in. After I greeted him, we went to the small conference room for privacy.

“Jamie told me they’re in contact and BLS is playing coy, but it’s clear they’re interested.”

“They’ll try to get as much as they can, obviously.”

“And we’ll try to pay as little as we can,” I grinned. “I know how this works. At some point, we’ll have to do some ‘due diligence’, but Jamie suggested we hire a third party to do it so as not to give anything away to the staff.”

“That makes sense. It’ll cost you some money.”

“I know somebody at Arthur Andersen who might be able to help us get a good deal,” I grinned.

“Speaking of your sister, I get the idea that things are kind of cold between you two. And not like when she was angry. Something else happened.”

“I’d say it’s because she moved in with Ed and is working hard on that relationship, which is exactly what I want her to do and what I advised her to do. I told her she had to go to Ed for anything she needed, and if he felt my input was needed, then she could come to me.”

“That’s kind of harsh, don’t you think?” my dad asked.

“It’s more or less what I did with Bethany and Stephie, and it worked out just fine. Well, in terms of keeping our relationships proper and me not interfering in their marriages.”

“You think that’s where this is headed?”

It had better be, I thought. Otherwise, things were going to spiral out of control and go straight to hell.

“I’d bet on it. It’s about a sure thing as you can find. She could blow it, but I don’t think so. He’s the right man for her, Dad, I’m sure of it.”

“And that business with the law?”

“It’s obvious he was cleared given that the City of Chicago did a background check and he passed it. I think that was just being in the wrong place at the wrong time. You know I worked for Joyce’s grandfather for a couple of years. Ed just happened to be in a place where an armed robbery took place. It could have happened to me, too. And I’ll point out that Stephanie still has that misdemeanor arrest and court supervision for another year or so. Ed has a clean record!”

My dad nodded, “Good point.”

“How are your hips?” I asked.

“Why?”

“I thought we might take a walk.”

He smiled and followed me out of the office. As we left, I saw Barbara and her team coming up the walk. We exchanged greetings and they went in while my dad and I walked down Hyde Park Boulevard.

“So who the heck is Louis B. Hanal?” I asked.

“My alias in Cuba. Back then, they often just changed your last name because it made it easier if someone called out your name. It’s too easy to get caught by either responding to the wrong name or not responding to the right name. And because almost nothing was computerized, you could never really track somebody’s past.”

“So how did they turn up those records?”

My dad laughed, “Social Security! I’m not quite sure how it happened, but there must be some record at the Social Security Administration linking my records. There’s not supposed to be. The Navy Department properly changed everything, but it looks as if Social Security didn’t. A certain government agency called the FBI and warned them off. They won’t ask again. That said, they did figure out that Joyce is 100% Italian.”

“Great,” I sighed.

“She got a call from them earlier in the week. I believe the term she used was ‘pound sand’, and she turned half-a-dozen lawyers loose on them.”

I laughed, “That would be Joyce. She keeps her books and records pretty much the same way we do. They can audit her and they won’t find anything more than they did here - a minor bookkeeping error that translated into us owing the government about $400.”

“I bet Elyse was kicking herself.”

“For three days, before I finally told her to dock her own bonus $400 if she was so damned guilty about it. She relaxed after that. It really was just a simple mistake. Bruce missed it as well, and so did the auditors. But not the IRS!”

“They had to find SOMETHING, Son. Be glad it was that instead of them finding some technical error and trying to really nail you.”

“So, about this Cuba thing? When do I get to hear the story?”

“Legally? 1995. I’m in good enough health I think I’ll wait, if that’s OK with you.”

“The last thing I need is MORE trouble with the government. Follow your rules. What about World War II?”

“It’s hard to tell that without getting into the OSS stuff.”

“Got it. I guess I’ll be patient! How are things otherwise?”

“I’m doing some consulting for Roto-Rooter on restructuring in Cincinnati.”

“Your old competitors?”

“Who ELSE do you go to? I kicked their butts from the Ohio River to Dayton and back!”

“True!”

“How are things with your wives?”

“Jess is really struggling with the stress of work and family. But it’s to be expected, according to Al Barton.”

“He’s a good man. I guess he’s like a substitute father for her.”

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