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

A Well-Lived Life - Book 9 - Anala

Copyright © 2015-2023 Penguintopia Productions

Chapter 43: Pre-departure Briefings

Coming of Age Sex Story: Chapter 43: Pre-departure Briefings - 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  

June 1984, Milford, Ohio

On Monday morning, Bethany, Josie, Jennifer, Stephanie, Zach and I all went to breakfast. We talked about the wedding and Stephanie filled me in on my mom's reaction.

"At church, she and Dad sat way in the back. You know his opinion of church, so no surprise there. At the reception, I think you saw her leave the room when Jennifer and Josie danced, and she wouldn't come back. It was so stupid because later on, all the bridesmaids danced together, along with a bunch of the younger girls who weren't allowed to bring dates. But you know Mom!"

I sighed, "Sadly."

"She wasn't the only one," Josie said. "I saw quite a few looks of disapproval when we danced and afterwards. And when I kissed Jen, one old biddy gave me the most evil stare."

"Ignore them," I said. "Intolerant people just suck. Let them be uncomfortable. Maybe they'll get a clue!"

"How long is it going to take?" Josie sighed.

"A long time," Bethany said. "I'll bet if it does happen, it'll be when all of our kids are grown, if not longer."

"What? Thirty years? Ugh!"

"That's if you're lucky, Josie," Bethany commiserated. "But you won't find any of that in Steve's house. All you'll find there is love and acceptance. He wouldn't have it any other way."

"Jamal and Jeremiah might have some concerns," I said thoughtfully. "But I'll talk to them before you guys move to Chicago. If they can't accept the two of you, then they can't be part of our group. It really is that simple."

"Even after saying that Jenny had gone to the 'Dark Side' and was 'playing for the other team'?" Josie asked.

"Yes. Remember the context, Josie," I said.

"Josie, Steve's not judging your lifestyle or your sexuality," Bethany said. "He's working through the fact that a girl he loved basically rejected his marriage proposal to marry somebody else. It wouldn't matter if you were a guy or a Martian. In other words, you being a girl has nothing to do with it. Your being the successful suitor does."

"Zach, what's your opinion?" Stephanie asked mischievously.

"Man, I don't even have an opinion!" Zach said. "I didn't even realize until just now! I was too busy paying attention to you last night!"

"As you should have!" Stephanie said primly.

Everyone laughed.

"Still the Princess, Lord High Ruler of the Universe, I see," I said, chuckling.

"Yes!" Stephanie declared, winking at me.

When we finished eating, I took Stephanie aside to say goodbye. With Zach there, we couldn't kiss as we wanted to, but we hugged tightly and we both said that we were looking forward to her visit in July. I asked her about Zach, and she arched her eyebrow and shrugged.

"Going to give him a chance to have the best pussy on the planet, Squirt?" I whispered.

"If so, only after we're together, Big Brother. It'd just be a fun fling, nothing serious."

"You'll spoil him for any other girl, Squirt."

"I tried that with you and it didn't work," she giggled.

"If you weren't my sister, it would have. For sure."

"I love you, Big Brother."

"I love you, Squirt."

We hugged again, and then she and Zach got into her car so she could take him home. Bethany and I dropped Jennifer and Josie at the Spencers' and then went to her house so I could pack my things. Bethany and I kissed fiercely, and she walked me out to my car. I told her I was looking forward to seeing her in August. I reminded her that Sofia and Kara would both be there when she arrived, and my other housemates would trickle in during the week. We kissed again, and I drove back to the Spencers' to pick up Jennifer and Josie for the drive to Chicago.

June 1984, Chicago, Illinois

The drives between Milford and Chicago had become routine, though I wouldn't be making them nearly so often in the future. I took the opportunity of over five hours on the road to raise the issue of our relationship and how it would work. Jennifer, Josie, and I discussed and debated everything, including our ideas for raising a kid. We discussed some practical matters and finally, talked about the commitment ceremony.

"We want to exchange rings," Josie said. "But I'm not sure how that would work. You're going to need to wear your own wedding ring, too."

"What if I wore a matched ring on my right hand?" I said. "The same design as yours, but in a guy's size."

"That would be cool," Josie agreed. "And we'll do this next Summer in Chicago?"

"Sure. When were you thinking of getting pregnant, Jen?"

"In maybe four or five years," Jennifer said thoughtfully. "That lets me graduate and work for a few years. The one thing we haven't talked about is how we handle caring for the kid and working."

"With three professional incomes, we can afford a nanny," I said. "Or we could get an au pair. I can't imagine any of us not working for seven or eight years. And if things work out the way I want them to with my business, I'll mostly work from home for a few years. The house has plenty of room for that. We can turn the study room into the company office at some point."

"What's Elyse going to do?" Jennifer asked.

"I haven't asked, but my guess is the same thing. Whoever my wife is won't have to work unless she wants to. I'll leave that up to her. Obviously, if it's one of the usual suspects, we're talking about a medical doctor, clinical psychologist, teacher, diplomat, or budding programmer. None of those sound like stay-at-home moms to me!"

"And if we all shared one nanny, it'll be pretty inexpensive," Jennifer said, then added mischievously, "If she's young and cute, we might end up with more kids than we bargained for with the stud here hanging around!"

We all laughed. It seemed as if we had a plan, and now it was only a matter of waiting until the girls moved to Chicago. Things were coming together, and so far, it looked like Fate had taken a vacation. I hoped the fickle bitch enjoyed it and decided to stay away forever. But I sure wasn't going to count on it.

At home, the first thing I did after getting the mail was to check to see if there were any messages, but the light on the machine was solid, not blinking. Next, I started some laundry and then walked down to the shop where I'd rented my tuxedos in the past to reserve one for my trip to DC. I walked back home and went through the mail. There were a couple of bills, so I wrote out checks and put them in envelopes for Anala to mail. There was also the 45RPM single from Sofia. I decided to play it.

The song was the type of banal pop that I didn't particularly like, but the tune was catchy nonetheless. I could see how the song could win the Eurovision contest, but I was sure that even the English-language version would get no airplay on American radio stations. When I finished listening to the song, I went up to my room and began packing my bags for my trip. Jennifer and Josie had offered to cook, and I took them up on their offer. Penny arrived with Alice in tow about 5:00pm and once Alice saw that Jennifer and Josie were there, she went back home. Penny barely waited for the door to close before giving me a fierce hug.

"I missed you!" she said.

"I missed you, too, Penny. Dinner's in about an hour. What do you want to do until then?" I asked with a knowing smile.

She flashed me a wicked smile, grabbed my hand, and dragged me up to my room. She shut and locked the door and attacked. For the next forty-five minutes, she alternated between riding me and sixty-nining, ending up with me cumming twice in her tight pussy. After a quick shower, we went downstairs for dinner just as the girls were getting it on the table.

"What time do you have to be home, Penny?" Jennifer asked.

"9:00pm. It's a school night and mom won't let me stay out one second later. She's mean!"

"Yes, your mom is so mean that she lets you come over here and have Steve give you five screaming orgasms!" Jennifer teased.

"At least!" Josie snickered. "We don't know about the quieter ones!"

"Uhm, I guess I was loud," Penny said, blushing.

"Yes," Jennifer said. "But that's OK. Your mom isn't mean. She's just watching out for you. Would you like to talk some more after dinner?"

"I do, but I can't miss saying goodbye properly to Steve!" she giggled.

When we finished dinner, Josie and I offered to clean up so that Jennifer and Penny could talk. Josie and I talked while we worked together in the kitchen.

"Jenny told me about how your first real girlfriend died. I can't even begin to think of what it would be like now, at twenty-one, let alone at fifteen."

"Yeah," I sighed. "It sucked. But Jennifer was there for me. She's always been there for me when it counted."

"Even when she moved away? And decided to go to Stanford?"

"It was her dad that moved the family, not Jennifer. She did her best to help me through it. The Stanford thing, well, in hindsight, I'd say it was a good thing, even though I didn't think so at the time. If Jen had come here, we might have tried to make it work. Can you imagine what would have happened if she'd figured out her sexuality after we'd been married for a few years? Talk about a nightmare!"

"You're pretty philosophical Steve. And in a healthy way. I hadn't really figured out that you saw me as a rival, but I suppose that is what I am. But if I understand correctly, Pete was a rival, too."

"Melanie and I were dating seriously — that is, fucking each other silly — when she met him. So in that way, yes. And I've never, ever stood in their way."

"Jenny says you pushed Melanie to fix things with Pete when they went wrong. Why not keep her for yourself?"

"For the same reason, I'm not fighting you. Pete and Melanie belong together. So do you and Jen."

"Wow! You really believe that?"

"When I saw you two dance, it kind of sealed the idea in my mind, yes."

"When we danced? Not when you watched us make love?"

"I've seen girls who are basically straight do that. Can I ask a question?"

"Sure."

"Jen says she can't be with me without you there. Are you the same way?"

"Yes, but not for the same reason. For me, it's because I promised Jenny that except for the very first time when you and I got to know each other, I'd never have sex when she wasn't there. For her, it's because heterosexual sex scares the hell out of her. Did you know that she won't let me use a dildo or even a vibrator on her, if it goes inside?"

That made me think back to the first penetration that night in Chicago. Maybe that's what I'd detected. It would make sense. It was odd, but then again, everything about the way things were going with Jennifer was a bit odd.

"No! Wow! I mean, she told me that the idea of any dick other than mine in her made her physically ill, but I didn't realize it went that far."

"It's strange. She has crazy, over-the-top, mind-blowing orgasms with you. With me, they're smaller, sweeter, as she calls them. I think I could give her bigger ones, but she doesn't want them. She wants tender and soft."

"So do I," I said.

"What?" Josie asked.

"Didn't Jen tell you? I prefer slow, passionate missionary-style lovemaking to everything else. Sure, threesomes are fun, and playing around is fun, too. But in the end, nothing tops one-on-one lovemaking."

"You are a strange dude. I know I said it before, and I sure don't mean it pejoratively. But most guys would kill for the wild threesomes we've had. If you want, I'll let you and Jenny love like that. She'll want me in the room, maybe even in the bed, but maybe you two need that. I'll ask her, OK?"

"More than OK!" I grinned.

When we finished the dishes, we went to the great room. It turned out that Josie played chess, so we sat down at the board and played a couple of quick games before Jennifer and Penny came to find us about 7:30pm. Penny came and sat in my lap while I finished the game with Josie, and then I led her up to my room.

"Penny, I want to make love to you. This will be the last time for over a month, and so I want to make it perfect. OK?"

"Oh, yes! That's my favorite, too!"

We made love as I'd suggested, with Penny having a dozen orgasms before I pressed deeply into her and came hard, her spasming pussy milking me for every drop I had to give her. We kissed softly for a time, then I led her to the shower and we washed each other, then dried off and went to sit on the loveseat in my bedroom.

"Did you have a good talk with Jennifer?" I asked.

"Yes. We talked about you, mostly. She really loves you. But she can't marry you. I was pretty confused, but she explained it and I asked questions and I think I understand. I just don't get why she likes girls and not boys."

"Why do you like boys, Penny?"

"Because girls are supposed to like boys!" she giggled.

"Well, yes. But you can't tell me why you feel that way, can you? You just know that you do."

"Yes."

"That's how Jennifer and Josie feel. They just know. And there's nothing wrong with that. Would you be upset if you saw them kiss?"

"No, I guess not. But I wouldn't want to do that."

"And Jennifer doesn't want to kiss boys, well, except for me, and that's because I'm very special to her."

"But Josie likes both boys and girls. Jennifer said so."

"Yes. And that's fine, too. Don't let the nuns try to tell you any different."

Penny giggled, "What do they know? How can someone who promises never, ever to have sex teach about sex? That would be like trying to teach math without ever having done a math problem!"

I laughed at her analogy, but it was indeed apt.

"I wouldn't say that to them," I grinned.

"No way! I'd get in trouble for sure. Besides, I don't talk about sex with anyone but your two friends, Jackie and Jennifer. If my mom found out I was doing this, she'd kill me!"

"And me, too!" I added soberly.

"Do you really like doing it with me?"

"Yes, Penny. I do. And do you like doing it with me?"

"Oh yes! When you come back, I'm going to attack you!" she giggled.

"I look forward to it. Let's go find the girls. We can hang out for a bit and then you can go home."

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