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

A Well-Lived Life - Book 9 - Anala

Copyright © 2015-2023 Penguintopia Productions

Chapter 66: Halloween Surprises, Part III

Coming of Age Sex Story: Chapter 66: Halloween Surprises, Part III - 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  

October, 1984, Chicago, Illinois

Bethany was right — I did have some very surprising things happen in my life. And they never seemed to stop. On the other hand, Fate seemed to have taken a holiday, and I was just fine with that. If she never came back, I'd be a very happy man. And given how things were going, I was pretty happy overall.

I walked out the back door and down the brick path to the back door of the coach house. I knocked and Patience opened the door to let me in. As was usually the case, lunch was on the table waiting, so we sat down to eat.

"That was a great party last night," Patience said.

"I agree," I said with a smile. "I think it went pretty well, if I do say so myself, and of course, I do!"

"It didn't seem like a college party," Prudence said. "No drunken frat boys, nobody throwing up in the toilet, nobody making out in the corner, nothing broken, no pot, and no police!"

"Except for the making out part, I can do without all of those. So," I said with a smirk, "was there any significance to who was the good witch and who was the bad witch?"

"No," Patience laughed, "we can both be bad or good."

"At the same time!" Prudence added with a smirk.

"I'd love to test that theory," I declared with a grin.

"I bet you would!" Prudence replied. "We've done pretty much everything together since we were little, even losing our virginity on the same night when we were seventeen. It was pretty much at the same time, though in different rooms. But sex is one thing we've never done together."

"All teasing aside," I said. "If you're not comfortable, just say so and I'll drop the entire subject."

"I don't think it's a comfort issue, I think it's a courage issue," Prudence said. "Plus the whole issue of exactly what you're looking for."

"You mean as in a relationship? I'll be blunt. If anything happens, it's just going to be for fun. I'm not in the market for a girlfriend. Or two," I said with a smile.

"With a house full of girls?" Asked with a soft laugh. "I can't imagine that you would be!"

"Everyone thinks that, but the reality isn't even close to the fantasy. Julia is engaged; Katy is dating seriously; Jackie moved out to live with her boyfriend; Cindi is dating seriously. The girl who's visiting, Bethany, is the one I'm most serious with. The girl who would be the love of my life is in California. And, it turns out, she decided to play for the other team."

"The other team?" Prudence asked, arching an eyebrow.

"She's lesbian. She and her partner will be moving into the coach house next Summer. She and I are still close, but she'd marry Josie if the government would allow her to."

"How the heck did she become the love of your life if she likes girls?" Prudence asked.

"She was seriously confused as a teenager, trying to understand why she was attracted to girls. She had serious problems with every guy she tried to be with except me, and well, we had more problems than you can shake a stick at. But I stuck with her and did my best to support her."

"You seem to have quite the complicated life," she said.

"You don't know the half of it! A girl I was madly in love with and wanted a future with died in an accident at age fifteen. And that was just the start of the complications."

"Holy crap! You're serious about that? This isn't some lame attempt to get laid by plucking our heartstrings?"

"As a heart attack," I said. "I visit her gravesite when I travel to Sweden. That's where she was from, and I've been there four times. The first time was for a year as an exchange student."

"And that's when you met her?" Prudence asked.

"No. She was an exchange student in my Junior High School. She died after she went home. I visited her family when I went there and put flowers on her grave."

"We grew up in a small town in the far western suburbs. About the only exciting thing that ever happened was losing our virginities on the night of our Senior Prom! We had nice, boring lives. Heck, neither of us had what you would call a steady boyfriend until the middle of Senior year."

"And now?" I asked.

"One joined the Army; the other went to Texas to work construction with his uncle. We've both dated guys from UofC, but nothing serious. Well, you know, fooling around, but not like we're steady with anyone."

"So you DO fool around!" I grinned.

We finished our lunch, and the twins cleared the plates from the table and put them in the sink. The coach house didn't have a built-in dishwasher, and a quick assessment of the kitchen showed that there wasn't really room to install one without losing all-important cupboard space.

"Of course we do!" Prudence said. "That isn't the question here. The question is, do we fool around together with you?"

"I vote yes," I chuckled.

"One yes vote! But I believe that it takes three," she said. "I don't think majority rules works here."

"No, it can't," I agreed with sincerity. "It has to be unanimous. What's YOUR vote?"

"We've debated this back and forth for weeks," Patience said. "We've never shared a guy, even one at a time. And we're not sure about having sex in front of each other, either."

"Then your votes would be 'no'," I said.

"You would think so, except that it seems exciting and daring!" Prudence said. "I want to try it so I vote 'yes'!"

I kept my expression as neutral, waiting to see what the other twin said.

"Oh sure, put it all on me," Patience said. "That's not fair!"

"You can say 'no' and I absolutely won't be upset," I said. "Please don't do something you aren't comfortable doing."

She sighed, "You're cute. You have dreamy eyes. You're in good shape. You seem like a really nice guy. If you tried to pick me up at a party, you'd have a pretty good shot of getting lucky. Heck, if you asked me right now, I'd probably take you up to my room for some fun. But I don't think I can have a threesome with you two."

"Probably, Sis? You know you want him! Just take him upstairs for fifteen minutes, do the deed, and then I can have my turn."

I chuckled. "Fifteen minutes? I won't have even gotten past using my tongue at that point! As for doing the deed, that's twenty minutes by itself!"

"If you aren't full of crap, then I want to go first!" Prudence laughed. "You'd eat me that long? And you can screw that long?"

I nodded.

"And you have rubbers with you?" she asked.

I nodded again. She got up from the table, took my hand, and practically dragged me up the stairs to her room. We locked lips and quickly removed each other's clothes. She pulled down the bedspread and got into bed and I looked over her sexy body — long legs, small, firm breasts topped by hard pink nipples, a flat stomach, a neatly trimmed triangle of dark pubic hair, and plump labia. I wasted no more time and got into bed with her and lavished attention on her breasts. After a few minutes, I kissed my way down to her mons, and then slowly pressed my tongue between her labia.

Prudence had a musky smell, with a hint of strawberry, which was likely from her soap. As promised, I spent the next fifteen minutes with my tongue in and around her pussy. She only had one orgasm, but it was huge, causing her entire body to shake as she pulled my head against her and bucked her hips.

I got up and retrieved a rubber from my pants pocket and ripped open the package. Prudence watched as I rolled it on and smiled as I climbed into bed.

"I like it on top," she said.

I turned to my back, and she swiftly mounted me and began slowly riding me, moving her hips back and forth and raising and lowering herself, seeking her pleasure, while I ran my thumbs over her nipples. A few minutes later, I saw the door to the room open a bit, and Patience slipped quietly into the room. She put her finger to her lips and watched her sister and me screw.

I tried to keep a straight face when I saw Patience slide her hand into her jeans and begin fingering herself. It was clear that she was excited, and I wondered if she'd work up the courage to join us. I saw her face contort and assumed that she'd just rubbed herself to an orgasm; an idea confirmed when she groaned softly. Prudence snapped her head around and saw her sister and laughed.

"Well, don't just stand there, silly!" she giggled.

"What do I do?"

"Get your clothes off and come straddle my face," I offered.

She nodded and quickly stripped down, revealing a body that was nearly identical to her sister's, though she appeared to have slightly larger breasts. She walked over to the bed and tentatively climbed in, kneeling with one knee on each side of my head. I grasped her hips and pulled gently, causing her to lower her already dripping pussy to my lips. I thrust my tongue into her and she bucked and a squeak escaped from her lips.

"Oh!" she gasped a few seconds later.

Both girls had an orgasm about five minutes later, and then a second one a few minutes after that. My release followed, and I filled the rubber with cum, groaning into Patience's pussy. The girls climbed off of me and sat on the bed cross-legged, smiling at me. I got up, walked to the desk, removed the rubber, and wrapped it in a tissue I took from a box on the desk. I dropped it into the trashcan next to the desk.

"I see you changed your mind," I said to Patience.

"I was outside the door listening, and I was curious, so I looked in. It looked so hot that I wanted to watch, and well, you saw what happened."

"I did. I'm glad you decided to join us!"

"Me too!" her sister said.

"How long before we can do that again? I mean, with me getting what my sister had?"

"Twenty minutes or so, at most," I replied.

And so it was that twenty minutes later they'd switched positions. While Prudence had been slow and deliberate when she rode me, Patience was anything but — she was energetic and wild, and rode me hard. I was really glad that I'd already cum once, as the combination of her actions and her sister's pussy on my face were enough to bring me right to the edge. I managed to hold out, so that Patience got her twenty minutes, but just barely.

After I disposed of the second rubber, I maneuvered the girls into my usual cuddling position and held them to me. They were certainly a lot of fun, and I absolutely wouldn't mind a repeat if they were so inclined.

"Are you both OK?" I asked after a few minutes of silence.

"More than OK!" Prudence said. "That was better than anything I've ever done!"

"Yeah, I'm OK," Patience said, but she didn't sound nearly as enthusiastic.

I stayed in bed with the girls for about twenty minutes, then got up and used the shower. They showered after I did, one at a time, and when we were all dressed, I kissed them both and headed back to the main house. Our usual Sunday gathering had been canceled for today, so only my housemates and Bethany were around. I found Bethany and Kara sitting in the Indian room, talking.

"Hey," I said.

"I'd say somebody had a good time," Kara smirked.

"Oh?" I asked.

She doubled over laughing, and it dawned on me. I had wet hair! I started laughing as well.

"What's so funny?" Bethany asked.

"An inside joke, though I thought I had shared it with you. Kara's mom discovered that we were intimate because Kara came home with wet hair and smelling of different soap."

"Oops!" Bethany giggled. "I guess you had a good time."

"I did, but I'm not sure that it will happen again. The dynamic felt a bit odd. We'll see what happens. Did you two have a good talk?"

"Yes, we did," Bethany said. "Would you take a walk with me?"

"Of course," I said.

We got up and went out the front door and started walking north on Woodlawn. I took Bethany's hand in mine and she smiled.

"Do you remember our first walk? The first time I held your hand, and you hugged me?"

"Absolutely. You were shaking like a leaf! But you got over it."

"I was scared out of my mind. I knew exactly where it would lead if I hugged you; what my body wanted. And that scared the hell out of me. But you loved me and helped me get to the point where I no longer worry about what happened when I was thirteen."

"I'm glad I could help you," I said.

"For a High School guy, you were amazing. Hell, for any age. I knew, back then, what I wanted from you, and it wasn't just you taking my cherry."

"I'm glad to see that you've come around to my way of thinking!"

"Yes, and it's something I'm going to use with the partners of rape victims in the future, who might be in that same circumstance. I'm glad I found you."

"I'm glad you found me, too. I guess we can thank Jennifer for that."

"And Kathy, for not scooping you up when she had the chance!"

"I suppose so. My life would have been very, very different if Kathy and I had gotten together in eighth grade."

"Yes. And hers as well. You two would be planning a wedding now, having never, ever been with anyone else. And she'd never have shaved her pubic hair!" Bethany teased.

"Don't remind me! If my instincts are correct, twenty years from now, she and I will be in that sauna and she'll STILL be shaved and teasing me about it. I may have to have Kurt meet with an unfortunate accident. He's committed a crime against humanity!"

"You don't complain about my shaved mons, Mr. Adams!"

"Sorry, but that red pubic hair was just a sight to behold. I guess I'm a sucker for redheads."

"Strawberry blondes come first in your book, and you know it! Speaking of which, how are you doing regarding Jennifer?"

"I'm at peace with it. I don't have much of a choice, but, as people keep pointing out, it's not like I've lost her."

"No, it's not. Is she coming to visit in December?"

"That's the plan, yes. Just her so we can have some time together. But we won't make love. She can't, not without Josie here."

"If you want my amateur-professional opinion, you need to be prepared for her to put a stop to your sexual relationship as soon as she gets pregnant. Her aversion to penetrative sex is pretty strong, if what you're telling me is correct. I'm pretty sure that there's something in her past that you and I don't know about. Something that despite her honesty with you, she still hasn't told you."

"I'm afraid that you're right, and I'm afraid to find out. But I suspect at some point I will."

"Just love her, Steve," Bethany said softly. "At this point, there's nothing she could reveal that would change your relationship, and she'll need you to be strong. She may not have even told Josie about it. Maybe not even her therapist."

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