A Well-Lived Life - Book 9 - Anala - Cover

A Well-Lived Life - Book 9 - Anala

Copyright © 2015-2023 Penguintopia Productions

Chapter 40: Josie the Pussycat

Coming of Age Sex Story: Chapter 40: Josie the Pussycat - This is the continuation of the story told in "Book 8 - Stephie". If you haven't read Books 1 through 8, then you'll have some difficulty following the story. I strongly encourage you to read those before you begin this ninth book. Like the other books in this series, there is a lot of dialogue and introspection. There is also a lot of sex. Book 9 has 82 chapters and about 448,000 words. It's a lengthy read. I hope you'll stick with it!

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Mult   School   Incest   Brother   Sister   First   Slow  

May-June, 1984, Chicago, Illinois

The rest of the week flew by. I worked all three days, Jackie visited on Wednesday night, and to my surprise, Penny decided to talk with Jackie instead of asking me to take her to my room. When Penny left, Jackie explained that Penny had asked her a bunch of difficult questions about love and relationships and that she'd done her best to answer. She felt Penny was trying to work out for herself what it meant to be with me and, at the moment, had no idea, but was going to enjoy the sex until she figured it out.

Anala stayed over on Friday, as usual, and stayed on Saturday morning so that Penny could stay with me without her mom hanging around. Anala and I talked more about Becky, Penny, and the other girls, and I felt I was making some progress. The talk with her helped me to order my thoughts for my appointment with Doctor Alborg and for my talks with Jennifer, who was arriving on Monday, which was just two days away.

On Saturday evening, I talked to Bethany and my little sister and then called Jennifer to confirm her arrival time on Monday. I was pleased that I'd have enough time to see Doctor Alborg and then head to the airport.

On Sunday morning, I called Karin and Sofia, and then headed out to Sandwich to make three jumps with Wally. He suggested that if I was serious about continuing, I should look at getting licensed and buying my own gear. He also suggested that I subscribe to Parachutist and Skydiving magazines. I let him know that I'd be gone for over a month traveling, but that I'd be back in late July.

When I got back home, I made a quick grocery list and went out to Jewel to shop. At home, I changed the sheets on Elyse's bed, because she'd given me permission to let Jennifer and Josie use her room, rather than having to sleep in one of the guest rooms. I did some final cleaning and then sat in the backyard with my pipe and a glass of bourbon. Penny saw me over the fence and asked if she could come over. I told her to ask her mom, and she got permission to sit in the backyard with me.

"Is everything OK, Penny?" I asked.

"I guess. Jackie is really nice, and she tried to explain stuff to me. It's just kind of hard for me, I guess."

"Why is that?"

"Well, I always thought that you were supposed to be with one person, you know, for life, but it doesn't seem like you're going to do that."

"I don't know, really. Can I ask about your mom and dad?"

"Oh, sorry, I meant like one person at a time. You know, you get married to a person and you're with only that person until you get divorced or they die."

"That's what a lot of people think. I'm not sure that I agree."

"I guess not, given you want to have babies with Jennifer and Elyse."

"Jackie told you about Elyse?"

"Yes. She thought I knew already. Please don't get mad at her."

"I won't. It's OK for Jackie to tell you anything she thinks you need to know. How come you just talked to her on Wednesday instead of being with me?"

"That wasn't my plan! I just had so many questions that by the time I remembered I wanted to make love, it was too late!"

I chuckled, "That's OK. We don't have to do it every time. Sometimes it's just good to talk."

"When is Jennifer going to be here?"

"Tomorrow afternoon. Ask your mom if you can come to dinner on Tuesday. Just tell your mom that my friends from California will be here and if she wants to meet them, it's OK."

"I can do that?" she asked.

"Of course. I think you'll like Jennifer. And she's moving to Chicago in a year."

Penny sighed, "This is so weird."

"I know it's confusing, and I care a lot about you. But I don't want you to get the wrong idea about me. If you want to be part of my life, these are all things you need to know and deal with."

"Jackie told me that it's going to be hard and that I'm going to be confused. But I like being with you and I like your friends. And I like what you do with me. Is being an adult always this hard?"

"Harder," I said.

"That sucks," she sighed.

"It sure does."

I finished my pipe and my drink and then I went inside after Penny went home. I wrote in my journal and then headed to bed, anticipating seeing Jennifer and meeting Josie for the first time.

Monday flew by quickly and I found myself sitting in Doctor Alborg's office almost before I knew it. He asked a question, and I answered, and it rocked him back in his chair.

"How many girls have you been with?"

"About sixty, I guess."

"Sixty? And how many of those ended well?"

"Nearly all of them. I'm either friends with, or were friends with them when I last saw them. Several of them are living with me and a couple more are going to live with me starting in the Fall."

"I don't usually say this to my patients, and I beg your forgiveness in advance, but that sounds like bullshit to me."

"Doctor Alborg, I can give you a list along with phone numbers, or even introduce you to some of the girls. My most important girls, the ones closest to me, know all about the other girls."

"I'm not sure how you've managed that," he said, still sounding unconvinced. "Let's talk more about your relationships."

I spent the rest of the session talking to him about Jennifer, Bethany, Joyce, Karin, and Kara. He took lots of notes and on a number of occasions just shook his head, usually in response to some boneheaded thing that I'd done that the girls more or less glossed over. When we got to the end of our time, he put his pencil down and looked at me.

"I'd say that these girls enabled you by not holding you to some kind of standard, and that let you more or less slide on things that should have blown apart your relationships and taught you valuable life lessons. There's some key piece missing here that I can't quite put my finger on. We're out of time, but next time we will dig deeper into your relationship with your mom."

"If you remember, that's going to be in July, because I'm going to Ohio on Wednesday and then to Sweden right after I come back from Ohio. July 16th is the next Monday that I'll be here."

"OK. I do have a note to that effect. You don't seem to be having any day-to-day existential issues, so it shouldn't be a big deal. I'll see you in a month."

I left his office, walked home, and immediately got into my car to head to O'Hare. I parked in the short-term lot as I usually did and went into the terminal. As I walked towards the gate, I saw that the arrival board indicated that the flight was on time. I sat down with the latest copy of Byte magazine and read while I waited for the flight to arrive. About five minutes past the scheduled arrival time, the jet taxied to the ramp, and the engines were shutdown. The Jetway was extended and a couple of minutes later, passengers began to file out of the door.

I waited expectantly for Jennifer and a few minutes later caught a glimpse of her strawberry blonde hair, though my sight of her was mostly blocked by a tall, heavyset gentleman walking in front of her. I walked as close to the door as I could get and when she stepped through, I pulled her into my arms and hugged her tight. We kissed deeply, and I heard Josie's voice.

"Break it up, you two! Or get a room!"

I broke the kiss and looked over to where the voice had come from and almost fell over. Jennifer steadied me and started laughing while I did a double-take. They say in the world that there is a «doppelgänger» for everyone, but Josie's likeness was uncanny. She was, unbelievably, the spitting image of my little sister, right down to hairstyle, and the freckles on her face. From a distance, I wouldn't have been able to tell the two of them apart.

"What the fuck?" I finally stammered.

"Now you see why I wouldn't tell you?" Jennifer said. "Close your mouth, Steve. And then say hi."

I shook my head, blinked hard, then mumbled "Hi" to Josie.

"That's it? That's the greeting I get after all this build up? Lame!" she laughed.

She stepped up and hugged me and gave me a quick kiss on the lips. I was still in shock as we walked to the baggage claim to get their bags.

"How do you think I felt when I first saw her on campus?" Jennifer said. "I saw her across the quad and called out your sister's name! She didn't turn to look, so I walked over and only when I got right up to her did I realize it wasn't Stephanie. I told her what was going on, that I'd thought she was my ex-boyfriend's sister and my occasional lover."

"And I, of course, immediately concluded that she was bi-sexual, so I asked her on a date!" Josie smirked. "And the rest is history."

"Well, there was quite a bit more talking, but in the end, here we are!" Jennifer added.

"I don't even know what to say," I stammered, still not recovered from the shock.

"Now THERE'S a first!" Jennifer teased. "Relax, Steve. Think of how much fun this could be at the wedding!"

"Holy crap!" I said, laughing. "Talk about freaking people out!"

"Yeah," Jennifer smirked.

Their bags arrived fairly quickly, and we took them out to the car. Because the temperature was in the low 80s, I asked Jennifer to help me remove the T-tops and then we all got in for the drive to Hyde Park. When we pulled up in front of the house, it was Josie's turn to be flabbergasted. It turned out that Jennifer hadn't told her about the house and when we went inside, each room amazed her more than the previous one. The elevator literally made her stop dead in her tracks.

"Are you fucking kidding me? An elevator? Jennifer, maybe you should rethink things! If he can afford a house with an elevator, maybe you should think about marrying him!"

"Are you kidding?" Jennifer giggled. "Why buy the cow when I can get the milk for free!"

"Bitch!" I said, but I laughed.

"You know I'm teasing, Steve. But Josie, it's true. I don't have to make a commitment like that to Steve for him to share this with me. It's just his nature. When you meet his housemates, ask them, they'll tell you."

We finished the tour in the basement and I thought Josie's eyes would pop out of their sockets when she saw the sauna and the whirlpool.

"We are SO using this while we're here!" she declared.

"House rules are you have to be naked," I said.

"Everywhere? Or just in the sauna?" Josie smirked.

"Down girl!" Jennifer exclaimed. "I don't want to have to tickle you into submission in the first fifteen minutes!"

"Steve, you wouldn't let her do that to me, would you?" Josie said in a simpering, sexy voice.

"No," I said.

Josie smiled.

"I'd help her!" I added.

"Hah!" Jennifer declared triumphantly.

"This is going to be an interesting week," Josie laughed. "What are the sleeping arrangements?"

"I presumed nothing, so I have you two set up in Elyse's room. It's the big one right across the hall from the master bedroom."

"You were right, Jenny," Josie said with a smile. "He's handsome, he does have dreamy eyes, and he's a gentleman. The only question left is whether he's as good as you say he is!"

"Take him up to his room and find out, Jos. I'm not kidding."

"Whoa!" I exclaimed. "Slow down, girls. I need to get to know Josie a bit more, and some things have changed, Jen. We should talk. But let's have dinner first."

A look passed between Jennifer and Josie, but I wasn't sure exactly what it meant because I didn't know Josie that well. We went to the backyard so that I could start the charcoal in the grill, then went to the kitchen so I could prep the steaks and corn on the cob. About thirty minutes later, we were eating the steaks, corn on the cob, and coleslaw at the table on the patio.

"He can cook, too? Damn!" Josie said after sampling the food that I'd prepared.

"Yeah, and not just on the grill, either. He's a damned good cook. He also cleans, does dishes, does laundry, and otherwise is going to make an excellent partner for somebody someday!" Jennifer said with a smile.

I suppressed a sigh. She was making a point, and I understood it. I just didn't like it. I let the comment go and changed the subject.

"Jen, Penny is coming to dinner tomorrow night, and then we leave for Milford on Wednesday. I assume nothing has changed and you two are staying at Melanie's?"

"Yep. Sorry to kick you out of your room, but I can't imagine that you're too upset about sleeping with Bethany."

"No," I grinned. "You know damned well I'm not! Heck, you're the one who initially fixed me up with her all those years ago."

"True. What is it now, seven years?" Jennifer asked.

"Freshman year. It seems like forever now."

"Who's Penny?" Josie asked.

"My neighbor," I replied. "I've been teaching her computers for about a year."

Jennifer smirked because she knew that more was going on, but when she didn't say anything, I assumed that she hadn't told Josie about Penny and me. We finished eating and after we cleaned up, Jennifer asked if I wanted to talk.

"That's probably a good idea. Josie, you're free to go anywhere in the house except the girls' bedrooms. There are computers, cable TV, the stereo, a bunch of books, and you saw the pool table. Just make yourself at home. Jen and I are going to go for a walk."

"OK," she said, giving Jennifer a quick kiss before we left the house.

Jennifer took my hand in hers as we walked along Woodlawn Avenue. We'd gone a few blocks before she asked what I wanted to talk about and what had changed.

"For the last month, with one exception, I haven't had sex with anyone except Penny, despite several offers."

"Really? What's going on?"

"A lot. I'm back in therapy again, and I've been working through a lot of issues with help from Jackie and Anala. To be honest, I wasn't sure I was going to be with you when you came here."

"What?!" she gasped, a sudden angry, puzzled frown clouding her face. "You better start explaining."

"It's a bunch of things, but mostly it comes down to a completely empty feeling about sex due to some less than satisfactory results."

"Bad sex? You?"

"Not physically, no. You know I'm pretty good at that, and I guess you've been bragging to Josie about it. Just the way things turned out. The real catalyst was a couple of 'Kellie Linden' situations, plus the mess with Joyce and Connie, and a singularly unsatisfying couple of trysts with other girls. I guess I'm just burned out that way.

"Anala felt I was trying to drown myself in sex to avoid dealing with a certain situation, and Bethany agreed. My solution to that was to have Anala move in with me, but that backfired and really upset some of the girls, especially Penny. I changed that, but then I just felt like I couldn't sleep with anyone. Jackie convinced me that if I stopped being with Penny, I might really hurt her because she's so young and might not understand."

"What 'certain situation' are you referring to?"

I sighed, "Jennifer, I love you. More than anything. I didn't break my promise to you, but it has to do with Becky."

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