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

A Well-Lived Life - Book 9 - Anala

Copyright © 2015-2023 Penguintopia Productions

Chapter 31: A Well-Lived Life?, Part II

Coming of Age Sex Story: Chapter 31: A Well-Lived Life?, Part II - 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  

April, 1984, Chicago Illinois

"So what are you going to do about Becky?" Elyse asked.

"I have no idea," I replied, managing not to sigh. "I have to think more about it. I'm supposed to have lunch with her next Saturday. Then I won't see her at least until after exams. I'll have to figure out what to do at that point. Honestly, as I think about it, my first impulse is to do nothing and keep the status quo. I think it might be too late to resurrect things, and doing so would, at a minimum, destroy my relationship with Jennifer, piss off Bethany, and result in my death by choking on my severed dick at the hands of my sister."

Both girls laughed and Elyse said, "That might be a deterrent!"

I wanted to sit in the sauna, and when I said I was headed there, both girls decided to come with me. We followed the weekday rules and sat naked, fairly close together, on the top bench. The girls knew my routine, and stayed quiet so that the heat and steam could work their magic on me. When we finished, I was surprised to see both girls follow me into my bedroom. They joined me in the shower and worked together to wash me with soap, then toweled me dry. They led to me to bed and snuggled close to me, their naked bodies pressed against mine. I smiled as I fell asleep, thinking about the intimacy we were sharing — an intimacy that neither included, nor needed, sex.

I woke before the girls and maneuvered out of bed, doing my best not to disturb them. Neither of them had class until later, so I went into the bathroom to shower, then quietly dressed and went down to eat breakfast. It was early, so I ate alone, then headed to IIT to pick up Dave and drive out to the suburbs for work. I turned on WBBM Newsradio to listen to the news, and in the hopes that Dave wouldn't want to talk the whole way. I was pretty sure that he noticed that I was preoccupied but he didn't say anything.

At lunch Dave finally asked what was bugging me. I told him it was just an issue between Anala and me and we were working on it. He didn't know all the nuances and issues of my relationship with her, so it didn't make sense to try to describe it in any detail. Fortunately, Dave just nodded soberly and finished his lunch. Guys didn't seem to need to talk as much, and right now, that was just what I needed.

I arrived at home late as usual on Tuesday, and decided on a sauna. I smiled when a few minutes after I'd gone in, Jackie and Elyse joined me. They sat quietly and when it was time to get out, they repeated what they'd done the night before. It was comforting to have both girls with me, and once again, I felt true intimacy, something that I hadn't had enough of. While I lay there with my eyes closed, holding lithe young bodies to me, I reevaluated my relationships.

I thought about true intimacy, as Anala called it, and wondered who I'd actually achieved that with. Melanie once, but no longer. Bethany. Stephanie. Elyse. Sofia. Anala. Jennifer and I were working on it, but the lies of the past had prevented it until recently. That was really it. Jackie was developing, but she'd be moving on very soon. There were others, like Debbie V that I'd been close to, but hadn't been with long enough to get to that point.

Four big names floated around in my head — Kara, Tatyana, Stephie, and Becky. With each of them, I'd moved past just superficiality and into something deeper. But none of those four had come close to what Bethany and I or Anala and I had achieved. Stephie had moved on to Red, someone she'd achieved that intimacy with long before she met me. Kara's meltdown shattered what we had and I wasn't sure that it could be rebuilt, even if I wanted to, and that was an open question. Tatyana had tossed a monkey wrench into the works with her thoughts of changing her plans. The intimacy that she and I shared was very different from with any of the others. With Becky, I was confused as hell.

One other name popped into my head unbidden — Penny. I'd spent most of the last year getting to know her. What was interesting was that, unlike Kara, Becky, or Stephie, it wasn't just a long seduction. That had been the furthest thing from my mind until the girls pointed it out to me. She was the youngest of the girls by far, even younger than Tina Hoff, who was now nearly seventeen. Any future with Penny would be much further down the road. But I was WAY ahead of myself.

I eventually fell asleep, comforted by the girls in bed with me. They were both still with me when I woke on Wednesday morning, It was warm enough for me to run, so I got out of bed and put on my sweat pants and sweat shirt, then laced up my sneakers and headed out to run. When I came back, the girls were out of bed and joined me for breakfast after I took my shower.

"I changed the sheets," Jackie said. "I wouldn't want Penny to smell other girls in your bed."

"Thanks. I'm still conflicted about everything," I sighed.

"Do you remember how Anala told you to be decisive with Penny? You need to be that way tonight. Don't get all morose or introspective. She is NOT a mistake, and if you tell her or imply to her that she is, you'll crush her."

"I know. I'll work on my attitude today. I promise."

"Good," Jackie said. "Now eat. We cooked for you, for once."

I smiled and sat down to eat my pancakes and bacon.

"Steve," Elyse said. "Jackie and I had a long talk before you arrived home last night. We decided that there's something you need and we want to help you."

"What?" I asked.

"When you're ready, the two of us are going to fuck your brains out. Together."

"I don't know if that's a good idea, or if it's what I really need," I said.

"Have I steered you wrong?" Elyse asked. "Has Jackie ever done anything to hurt you?"

"No," I said.

"Good. Then you let us know when. But not tonight. You need to focus on Penny, just as Jackie said. If you decide to end it with her, it has to be down the road and you have to work towards that. Got it?"

I nodded thoughtfully, "Yes."

Later that afternoon, after I arrived home from school, I wrote in my journal, once again trying to sort out my feelings. I wrote a couple of pages, then turned on the IBM PC to try to finish the work for the unions. I was happy when I finished just in time to make dinner. I had some testing to do, but that was all. I could drop the disks off on Friday after class.

Penny arrived after dinner as usual, and it was immediately clear that she was in a foul mood. We went up to my room and when I tried to kiss her she turned her face away.

"What's wrong, Penny?" I asked.

"I got my period!" she groused. "I wanted to fuck, but now we can't!"

I sat on the loveseat and patted the cushion next to me. Penny sat next to me, her arms crossed and her visage cloudy.

"Penelope Margaret O'Neil. This is NOT the end of the world! First of all, how do you feel?"

"Fine. I was a bit uncomfortable on Monday but last night I was fine. Well, until I got my stupid period!"

"Most girls are happy when they get their period after the first time they have sex, Penny. It means that they aren't pregnant."

"I'm on the Pill! I don't need a stupid period to make it so you don't want me!"

"What are you talking about? Of course I want you!" I said.

"Mary says her boyfriend won't touch her when it's that time of the month. He calls it 'on the rag' and treats her like she has some kind of disease!"

"He's a moron. Come sit in my lap."

"Why? We can't do it!" she whined.

I pulled her to me and she reluctantly sat in my lap with her arms around my neck.

"First of all, you do not have a disease. It's just a natural process. Secondly, we could do it. It would just be really messy. And you know what? If you want to, I will and I don't care how messy it is. I'll put a large towel on the bed so we don't stain the sheets. Or we could do it in the shower or bathtub. We just have to make sure your hair is dry before you go home."

"Really?" she perked up.

"Really. I will do anything you want, Penny. Anything."

"Yes! Take me to bed and fuck me, please!" she giggled.

We stood up and I went to the bathroom and got a large, soft towel to spread on the bed. After I'd arranged it, Penny and I kissed and undressed each other. I picked her up and put her on the bed, making sure to position her butt on the towel. I kissed her lips, then planted a kiss on each nipple. I had an idea that would make a point with her. I kissed my way down to her mons.

"No! Gross! Don't!" she protested.

"Shh! I know what I'm doing!"

I very carefully kissed her and gently sucked her clit into my mouth. I was able to do that without getting a mouthful of her menstrual blood and she bucked and writhed as I did it. I had never had sex with a girl on her period before, so I wasn't sure about lubrication. I decided that I'd rather be safe than sorry, so I got my lube from the drawer and spread it on my dick.

"What's that?" Penny asked.

"Lubricant. I'm not sure how slippery you'll be!" I grinned.

"Just get it in me!" she giggled.

I wasn't going to make her wait. I got between her legs, positioned myself and with the help of the lube, buried myself deep into her in one strong thrust.

"Oh!" she moaned.

She wrapped her legs around me and I began slowly thrusting in and out. It felt somewhat different, and I attributed that to the mix of blood, the lubricant, and her natural lubrication. I leaned down to kiss Penny and I thought she was going to swallow my tongue. She sucked hard, and began humping hard against me. I began moving faster and Penny groaned into my mouth and I felt spasms in her pussy signaling her first orgasm. She broke the kiss.

"Fuck me!" she gasped, humping even harder.

I thrust harder and faster than I had Sunday night and Penny met every stroke by firmly pushing her hips up to meet me. A second orgasm overtook her and she groaned loudly and began wildly humping. I matched her movements and pounded in and out of her. Penny wasn't able to catch her breath and was gasping each time I slammed deep into her. The extra lube made it easy to move even in her tight tunnel.

Suddenly Penny squeezed me tightly with her arms and legs and held her breath. I continued thrusting hard and a few seconds later she let out a loud groan and her body shook hard. The tight squeezes of her pussy pulled me along with her and after two more thrusts I pushed all the way in and came hard, filling Penny with cum. I collapsed on her, crushing her small body into the bed.

Penny's breathing was ragged, and her heart was pounding, but she gently ground her clit against me, trying to give herself another orgasm. I pushed my hips forward so that my pubic bone would apply more pressure and a minute later I was rewarded with a series of small spasms around my dick. Penny blew out a long breath, then resumed her grinding. All told, she managed to give herself four small orgasms before she relaxed.

"Thank you," she gasped.

"You're welcome. Let me know when you're ready to get up."

"Never!" she giggled. "We can stay here and fuck. Your friends can bring us food!"

I chuckled, "Your mom and dad might come looking for you."

"They would. Bummer!"

"It's OK, Penny. We have to go to school, and I have to work, too."

"You'd rather do that than fuck all the time?" she giggled.

"Uh, no. But it IS kind of necessary so I can get my degree and pay the bills!"

"Was it OK for you? You came, but did it feel OK?"

"Absolutely!" I said.

"I bet it's a mess! I felt a lot of stuff run out of me when I had that huge orgasm."

"Want me to get up so you can see?"

"Yeah," she said.

I got up and she propped herself. There was a huge red stain on the towel, plus all over her thighs, my dick, and my thighs. There was even some blood in her pubic hair and on my stomach.

"Gross! What a mess!" she giggled.

"Let's get cleaned up," I said.

"Only once?" she asked with a silly smile.

"You had eight orgasms, you little vixen! How many do you need?"

"All of them!" she giggled. "But I guess we need to clean up the mess. Does Jackie or Elyse have a hair dryer?"

Out of the mouths of babes!

"I know Elyse does. Let's clean up and then I can get it from her."

We went into the shower and washed off the mix of cum, lube, menstrual blood, and Penny's juices. We hugged and kissed throughout the process, making it take a lot longer than had we just washed. When we got out, I carefully dried Penny and then myself. She went and got her purse and replaced the pad in her panties, then we got dressed. I went to Elyse and asked to borrow her hair dryer. She laughed and told me to get it from her bathroom.

Penny used the hair dryer, sprayed on her body spray, and then we sat on the loveseat together, cuddling until it was time for her to go home. I grabbed the towel from the bed, along with some other laundry and took it downstairs when we went. I tossed it in the washing machine, then walked Penny to the door and watched her scamper next door. She turned and blew me a kiss, which I caught and pressed to my lips, and then we both went inside.

Jackie stopped me as I headed to the kitchen to make some tea.

"She looked like she was in a foul mood when she got here, but she looked quite happy when she left. What happened?"

"I fucked her silly, that's what happened!" I grinned. "Her pissy attitude was because she got her period last night and she thought I wouldn't do it with her. It seems her friend's boyfriend treats her friend like she has the plague when she has her period."

Jackie laughed, "That must have been a world-class mess! You really take the cake, Steve. When I told you that you should have sex with her, I didn't mean during her period!"

"Other than being messy, it was fine!" I lowered my voice, "Heck, I even sucked her clit for a bit!"

Jackie's eyes went wide, "You know that 99.99 percent of guys wouldn't go anywhere near a bloody vagina. You, on the other hand, just take it in stride!"

"Can we talk about this morning?" I asked.

She nodded. I made some tea and we went into my study. I shut the door and we sat down. I poured tea for both of us and took a few sips.

"You're OK with having sex with me, even after the revelation about my sister?"

"Who knows? I've learned a lot from you about not judging and not applying external ideas of right and wrong. I admit I was grossed out and the entire idea struck me as repulsive. Then when Elyse made the comment about not abandoning you, I realized that I couldn't just walk away, even if I didn't want to have sex. I talked to her a lot last night.

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