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

A Well-Lived Life - Book 9 - Anala

Copyright © 2015-2023 Penguintopia Productions

Chapter 17: Surprise!

Coming of Age Sex Story: Chapter 17: Surprise! - 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  

February/March, 1984, Chicago, Illinois

After talking to my dad, I called Jennifer, but Josie answered the phone.

"She's been walking on air since she came back to Stanford. Are you THAT good?" she teased.

"I think it's a bit more complicated than just knowing how to give her an endless string of orgasms!" I chuckled.

"Oh, I know. So you'd be cool with us being a couple and Jennifer being your occasional lover?"

"Isn't that how it is now?" I asked. "The question in my mind is if I'm going to marry and settle down, so to speak. Jennifer doesn't think that I should."

"No, she certainly doesn't," Josie said. "She's a complicated woman. She's just walking into the room now. I'm looking forward to seeing you at the wedding!"

"Me too, Josie. Thanks."

"Hi, Steve!" Jen said when she came on the line. "How are things?"

"You know me; they only get crazier every day!"

"What now? Did something happen with Penny?"

"That's moving slowly as I said it would. She's ready to climb the walls, but that's normal. It's my brother. He managed to get himself arrested again."

"You knew that was going to happen."

"Well, I guess I thought there was a good chance. It's just strange to talk to my dad about it openly."

"Your mom must have lost her mind!"

"Close, I guess. She's taking some mild sedatives, but when the Milford Advertiser hits the streets tomorrow, it'll get worse, I'm sure. All her friends and all the people at church will know."

"That's a good thing. He's a pervert and needs to be off the streets."

"My dad is hoping for a short sentence and then mandated psychological counseling. I suspect, given the money he has at his disposal, that's what will happen. If it does, then Jeff misses maybe one semester at Bowling Green. I honestly think he'll do it again and a third time is surely going to put him in jail for a long time. One thing is sure; I'll never ever let him near any kids of mine!"

"Nobody should. Talk to Bethany, but I don't think those things are really curable, just controllable. And the person has to want to control them. It doesn't seem like he can. I mean, if you got arrested for something, would you do it again?"

"Hell no. Of course, my goal is to never get arrested!" I chuckled.

"Same here. Though given my choice in partners, I have to stay out of like half the states where having sex with Josie would be illegal. Hell, there are a dozen states where my vibrator is illegal. And Elyse's toys would get her in serious trouble in places like Alabama, Texas, or Georgia."

"What the hell? Seriously? Do people not have better things to do than worry about who's having sex with whom and how they're doing it?"

"You mean like your mom?" Jennifer asked.

"Yeah, yeah, I know," I sighed. "But really?"

"Steve, think about your Calvinist acquaintances. They fear, more than anything, that somewhere, someone is having fun, and they are bound and determined to stop it."

I laughed, "Kent van der Meer. And look where that got him."

"Yeah. Speaking of him, how's Kara doing?"

"I guess you can say that she's doing well. I saw her when I was in Milford to see Joyce. She's not making any play for me, or anything like that, if that's what you're worried about."

"I'm not worried. If she ever does make a play for you, it'll be on terms you can accept. She won't even try otherwise."

"You mean a group situation?"

"She has to know by now that your future is most likely not going to be monogamous. I know you don't believe that just yet, and it's remotely possible that you never will, but tell me, do any of the girls except Karin think that's going to happen?"

"Funnily enough, the Swedish girls — Sofia and Tina — would probably tend to agree with Karin. But the main girls here? They all agree with you. And so does Stephanie."

Jennifer laughed, "Of course she does. She has her own dog in this hunt, as you well know."

"Two dogs, Jen. You AND me."

"It's too bad one of you wasn't adopted. Then you could just do what you both want and nobody could stop you."

"Well, given that both she and I have my mom's traits, and Jeff looks like my dad, I'd say there's little chance of that being true. And honestly, at this point, my dad would have told me. Or my mom would have used it against me in some way."

"True. You've been talking with Anala about your struggle on this issue, right?"

"It's a constant topic of discussion. I have time to figure it out. It's not like anyone is itching to get married immediately. Elyse and Bethany are both going to be working on their Master's degrees. Sofia has eight years of school and then her internship. Anala already made it clear that she just wants me as a lover and kindred spirit until she's ready to marry and have kids, and all that changes at that point is the lover part. And you, well, you told me what you want, and it fits."

"That's all true. Remember when I pushed back about the promise ring? Now do you understand why I did that?"

"Yes, I do. Though I'm not sure that you knew exactly why you were doing it. You didn't know who you were at that point any more than I knew who I was."

"We were pretty young," Jennifer said. "That was before you went to Sweden, so we were what, sixteen?"

"We're still pretty young, when you think about it. I'm not even 21 yet!"

"True, but you're going to have one hell of a birthday present if what I surmise about your little friend is correct!"

"Mmmmm, could be!" I chuckled in my best Bugs Bunny voice.

"She's going to fuck you within an inch of your life, Steve, and you know it!" Jennifer said with a laugh. "That's why you're taking it slowly. It's like the world's longest fuse on an atomic bomb."

"Maybe, Jen! We'll see."

We talked for a few more minutes to catch up on how we were doing in school and other stuff that was going on, then said our goodbyes. We didn't finish the call by saying that we loved each other — that was assumed at this point. The question was only what we were going to do about it going forward. And the answer to that was much further down the path than either of us could see at the moment. Our paths would converge at Pete and Melanie's wedding and then diverge for a time before school ended. After that, well, I had no clue.

I sat back in my chair and put my feet up on my desk and closed my eyes. Things had become complicated for my sister and I wasn't there to help her day to day. On the plus side, I'd see her in two weeks. She'd have either Trish or Shelly with her, and neither of them would make an issue of her sleeping with me. I'd have to remember to tell Penny that I wouldn't be available during Spring Break. That would bug her, but I wasn't going to take time away from my little sister.

All the craziness had kept me from paying much attention to the Olympics, which were in full swing. The Russians won the ice hockey gold medal, redeeming themselves for their embarrassing loss to the United States in 1980. That had worked out very well for me, not just in terms of being happy about the result of the game!

The two weeks seemed to fly by. School was in full-swing, and the program for the scale was keeping me busy at work. At home, things went along as they usually had. Jackie and Elyse would occasionally show up at my door at bedtime, and Anala was with me on Friday nights. Our friends were at the house on the weekends as usual, and Pete dropped in both Sunday afternoons. The only real change was moving forward with Penny.

On Wednesday of the first week, instead of working on the computer, I took Penny up to my room and we sat on the couch and made out and I cupped her breast while we kissed. After about ten minutes, Penny broke the kiss.

"Would you touch me, please?" she asked breathlessly.

"Yes," I said gently. "Would you let me see your breasts?"

"If I do, would you kiss them?" she whispered.

I nodded, "Yes, Penny. I'd love to kiss your breasts!"

Penny pulled her sweater over her head without any hesitation, revealing a lacy, lavender-colored bra. I didn't recall ever telling her that purple was my favorite color, which made it even more exciting. Penny reached around behind her back, then looked up at me and stared me in the eyes. She unhooked her bra, shrugged the straps fall from her shoulders, and let it fall into her lap. I looked down and saw two perfectly firm, perfectly round, small breasts.

"You're beautiful!" I whispered.

She smiled and looked expectantly at me. I leaned forward and kissed her softly on the lips, then lowered my head so that I could flick her left nipple with my tongue. Penny squealed in delight at the contact. I moved slightly and did the same thing to her right nipple, then latched onto it with my mouth and sucked gently.

"Ohhhhh!" Penny moaned.

I opened my mouth and took more of her small breast in, lashing her rock-hard nipple with my tongue. Penny put her hands on the back of my head and held me tightly while I enjoyed the slightly salty taste of her skin. She was squirming a bit, which told me that she was at least as excited as I was about what we were doing. I switched breasts and ran my hand along the inside of Penny's thigh, being careful not to venture too high. Penny lifted her butt in an attempt to get my finger to touch her in her most secret place, albeit outside her jeans.

"Please," she begged hoarsely.

I slowly slid my hand along the inside of her jean-covered thigh and pressed gently along the seam of her jeans. Penny jumped a bit and then moaned softly. I increased the pressure slightly and slid my finger up and down along the seam. Penny's moans grew louder and suddenly she arched her back hard and groaned. She'd just had her first orgasm from a guy, and perhaps her first one ever. I released her breast, sat up and kissed her, and pulled her to me.

Penny was shaking and breathing hard, and I cuddled her while she calmed down and regained control of her breathing. I remembered what Jennifer had said and was pretty sure now that she was right about what my birthday was going to be like. The question in my mind was how far to take things before April 22nd. We could take things right up to the limit, including oral sex, before then, or save that for the day. I'd have to think further about it.

"Wow," she said when she'd calmed down a bit. "That felt SOOO good!"

I wasn't beyond a bit of teasing, of course.

"If you thought that was good, wait until you feel my tongue there!" I grinned.

"Oh God," she gasped. "I might die! My boobs were tingling so much I could barely stand it!"

"But what a way to die!" I chuckled.

"Can I touch you?" she asked.

"Next time, Penny. Next Wednesday. On Saturday, we need to stick to computers, given all we're doing is making out tonight."

"Can I see it, too?" she whispered.

"If you want," I said.

"Yeah," she sighed. "I want you to take me to bed right now, but I know you won't."

"On our birthday, Penny. It'll be worth the wait."

She sighed again and snuggled close. We kissed some more and eventually she put her bra and sweater back on and I walked her to the foyer so she could put her coat on to walk home.

"Purple is my favorite color," I said, kissing her goodnight.

"Good to know!" she giggled, and walked out the door.

On Sunday, I made my usual phone calls and talked to my sister about her trip. Everything was set, and she said that she was bringing Trish again. She told me that Trish had a steady boyfriend and understood that meant that she was off-limits. They would drive up early on Saturday morning.

I also talked to Kara and Bethany. Bethany was going to drive down on Friday night and stay over, then head to Milford on Saturday. I reminded her that Anala would be at the house on Friday as well, and Bethany said that was good because she wanted to talk with her some more. My call to Kara was similar to my previous ones, where we talked about what was going on in our lives and it seemed to me that she was making slow but steady progress. She asked if I was coming home for Spring Break and I told her that I wasn't.

The Wednesday before Spring Break, Penny and I once again went up to my room rather than to the study to work on computers. I reminded her as we walked up the stairs that we wouldn't be able to get together until after Spring Break. She pouted, but didn't complain. When we got to my room, she wasted no time and as soon as my door was closed, she had her sweater and bra off and sat on the love seat with a big smile.

"Show me, please!" she whispered.

I smiled and stood in front of her and pulled down my sweat pants and underwear. Given the lack of preliminaries, I wasn't hard, but Penny's eyes still grew wide.

"It's small!" she said.

I chuckled, "That's probably not the best thing to say to a guy, Penny!"

"I meant it's not like, big, like the health book talked about."

"That's easily solved," I said, sitting down next to her. "Give me your hand."

I took her hand and helped her grasp me and slowly stroke me until I was rock hard.

"Oh wow! Now it's huge!" she gasped.

I chuckled, "Saying THAT to a guy is a good thing. But it's about average size, I guess."

"You've measured?" she asked, now gently stroking me on her own.

I laughed, "No. One of my friends once told me that I was slightly bigger than average. I have no idea if that's true or not."

"And this will fit in me?" Penny asked, showing her first apprehension.

"Yes, it will. Remember, babies come out the same way, and they fit!"

She giggled, "Oh, duh! I'm a dope!"

"No, you're not," I reassured her. "You're just inexperienced. It's OK."

"If I keep doing this, will stuff come out?" she asked as she gently stroked me.

"Yes, Penny, if you keep doing that, I'll ejaculate and sperm will come out."

"Cool! Can I?" she asked.

"Yes," I said softly.

I leaned back and let her gently stroke me for several minutes. I warned her just before I was about to cum and she watched intently as jets of sperm erupted from my dick and landed on my sweatshirt and in my lap, and coated her hand.

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