A Well-Lived Life - Book 8 - Stephie - Cover

A Well-Lived Life - Book 8 - Stephie

Copyright © 2015-2023 Penguintopia Productions

Chapter 40: Surprising Developments, Part II

Coming of Age Sex Story: Chapter 40: Surprising Developments, Part II - This is the continuation of the story told in "Book 7 - Kara II". If you haven't read Books 1 through 7, then you'll have some difficulty following the story. I strongly encourage you to read those before you begin this eighth book. Like the other books in this series, there is a lot of dialogue and introspection. There is also a lot of sex. Book 8 has 82 chapters and about 455,000 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  

July, 1983, Chicago, Illinois

After I arrived home, I thought back over the time I'd spent with Carla. She seemed like a really nice girl, but one that was totally out of her element. She'd taken a pretty big risk in coming to my house alone and hadn't been prepared for the situation she'd encountered. I put the card on my desk without deciding if I'd call her or not. I was going to be pretty busy over the next few weeks, and then Stephie would arrive.

I decided to write a bit in my journal before turning in for bed. Anala was going to join me on Sunday evening for dinner and I wanted to have my thoughts in order before she arrived. My conversations with Jennifer had given me more to think about, and trying to put everything together was difficult. The one thing that kept coming back to me was that Jennifer had basically implied that I'd only ever be happy in some kind of group situation. History seemed to be bearing her out, but I still wasn't sure that it was the right long-term approach.

That brought me back to social norms and whether or not I was conditioned to think that one-man, one-woman was the only possible way forward. I'd joked with my dad about it, and he'd said that he didn't think it could work out, but now I wondered about that. I also wondered what Anala would have to say about it. I suspected that her views on duty, social norms, tradition, and her generally conservative views would result in outright rejection of the idea, but she'd surprised me before.

I finally shut the computer down just before midnight and headed to bed. I fell asleep almost right away and awoke refreshed early the next morning. I ran, practiced my kata, showered, and then called Karin. We had a good talk and spent longer on the phone than we had in over a year. When I hung up, I realized that was the first REAL conversation I'd had with Karin by phone since before her 'emergency' trip to Milford two years before.

Just before 8:00am, I left the house and walked to the bakery where I was meeting Candace. When I arrived, I looked in through the windows and didn't see her, so I stood outside to wait. About five minutes later, I saw her walking down Hyde Park Boulevard, and realized that she'd taken the El. Given that she lived in Bridgeport, that actually made sense, because it was a relatively short walk at both ends.

When she reached the bakery, she said hello and gave me a quick peck on the cheek. We went inside and we each got a toasted bagel with cream cheese and a coffee, then sat down at a small table by the plate-glass window at the front of the bakery.

"So," Candace said, "you're interested in a piece of Candy?"

I chuckled, "You are pretty damn forward!"

"Forward? That was tame compared to offering to show you my real hair color! Or did you think I was just going to show you and then button up and go home?" she said with a saucy wink.

"That wasn't a complaint, it was just an observation!" I said with a grin, taking a bite of my bagel.

"So, are we going to do this?" Candace asked, licking some cream cheese from her bagel and holding it on the tip of her tongue.

I laughed, "I guess that depends on what 'this' is!"

"Are you dense or just messing with me?" she asked, licking more cream cheese off the bagel in a very suggestive manner.

I smirked, "Let's just assume I'm dense! I'm not, but for the sake of argument, let's say I am."

She laughed, "You are anything but dense. You know damn well what I want. Or wasn't the cream cheese on my tongue enough of a hint!"

"I just thought you liked cream cheese!" I grinned.

Candace shook her head, "You are impossible! But I love it."

"I don't know. You're awfully old for me!" I teased.

"Six years? Really?" she asked with a smile.

"Actually, yes. I tend to stick with girls right around my age or younger. I've only been with a girl more than two years older than me once, and that was my first. She was just a bit younger than you are now."

"Jesus. How old were you?"

"Fourteen!" I grinned.

"Holy smokes! I was seventeen! Well, technically, because it was the night before my eighteenth birthday. I decided I didn't want to turn eighteen as a virgin."

"And how did that go?" I smirked.

"Eh, it was OK. It was uncomfortable, but he did manage to make me cum, but with his mouth and fingers, not his dick. He didn't last very long. The next time was way better."

"The only reason I lasted more than five seconds that first time was because she gave me a blowjob first. Well, that's only technically true. Does it count as a blowjob if you cum the second your dick is in her mouth?" I grinned.

"Good question. I assume you don't have that problem now?" she smirked, taking a bite of her bagel.

"You assume correctly. Can I ask why you're interested in me?"

"You're cool, your friends seem to like you a lot, you tip well, you're pretty decent looking, and you flirt. Why the hell not? I'm not tied down to anyone and I like sex. Is that a problem?"

"Oh no, not at all. I happen to like it as well. I'm just cautious, that's all."

"It's not like I haven't seen you a lot. Every week you came in for lunch with that Becky girl, who, by the way, is madly in love with you, if you didn't know it."

"Oh, I know it. Becky and I have a history. A long one that goes back to when we were fourteen. Saying that it's complicated is a massive understatement."

"She's your ex? Why do you hang out with her so much?"

"I suppose you could call her my ex, but it's even more complicated than that. At this point, she and I have some business stuff we do together, and she's helped me out in some sticky situations. We're just friends, nothing more."

"She looks like she'd be a handful in bed. Was it really that bad? I think she'd do anything you asked her to!"

"Yes, it was that bad; the relationship, I mean. It took years for us to even become friends again. Let's drop it. She's not why we're here today."

"True!" Candy smirked. "I mean, unless threesomes are your thing!"

I laughed, "I've been known to participate in the past, though only two girls at once is kind of tame."

"Bullshit!" she exclaimed. "Now you're just spouting BS and it's obvious."

I finished my bagel and took a drink of coffee before I responded.

"You'll find I don't BS about sex. I don't HAVE to! I've been with three girls at once, AND on one occasion, had five different girls the same night."

Candace just stared at me. I'd shocked her with that one and left her speechless. At least for a minute. She finished her bagel and drained her coffee cup.

"Well, if that's not bullshit, then we're wasting valuable time here!" she declared.

It was time to make a decision. So far, everything we'd said could be chalked up to harmless teasing. The question was, did I want to play around with Candace or not? She certainly didn't appear to be looking for anything other than a fun romp, and she was cute, like Katy had said the previous Fall. She absolutely had the body-type I liked and her personality bordered on crazy. And she looked like she'd be a fun sex partner.

Candace would be the epitome of a dalliance, as I'd called them back in High School. As long as she was OK with that, then I didn't see why I shouldn't just have a bit of fun. Jennifer certainly would say it was OK, though Anala might object on philosophical grounds, but I'd worry about that when I talked to her at dinner. I wouldn't give her details, but I would discuss what Jennifer had said. And Stephie's main concern was always what the girl meant, and because this was just for fun, she wouldn't have a problem with it either.

With my mind made up, I finished my coffee and motioned to get up to leave. Candace followed me out onto Hyde Park Boulevard and we walked towards Woodlawn.

"I didn't know there were any apartments on Woodlawn," Candace said.

"There aren't. We're going to my house," I said.

"Isn't renting a house here expensive?" she asked. "Even in Bridgeport it's not cheap. It has to be insane in Hyde Park!"

"I didn't say the house I was renting, I said my house," I said with a grin.

"Wait, aren't you from Ohio?"

"More or less. I was born in California, but my parents live in Ohio, which is where I went to High School."

"Then how do you have a house?"

"I bought it with my dad in April," I said as I turned to walk up the steps.

"No fucking way! You live HERE?"

"Yes, I do."

"Holy shit! Do you live alone?"

"Right now, yes, but once everyone comes back for school, I'll have five housemates who are renting rooms, along with my friend Stephie, plus some friends who'll visit most weekends."

I unlocked the door and let her in. She stopped dead in her tracks, looking around.

"Come on, I'll give you the full tour," I said.

I decided to do my best to shock her, so we took the elevator up to the attic room.

"A fucking elevator?"

"Well, no. Just a regular elevator, though I suppose it could be used for fucking," I smirked.

She laughed. I took her through the complete tour from attic to basement, ending standing next to the pool table.

"You wouldn't happen to be looking for a wife, mistress, or full-time lover, would you? To live in a house like this, I'd do anything!"

I chuckled, "I thought that was already on the table! Something about offering me a piece of candy and making sure I had a sweet tooth!"

"What kind of candy do you like?" she asked with a smirk.

There was only one thing to say, and it was the answer I'd saved for the question I was sure she'd ask.

"An all-day sucker!"

She burst out laughing, "You've been waiting all morning to say that, haven't you?"

"I have," I said with a silly grin. "And once you started teasing me with the cream cheese, I figured that was the best possible answer."

"That was a bit blatant, wasn't it?"

"No more than offering to show me your true hair color!"

"Well, let's go up to your room and play!"

"Birth control?" I asked.

"I hope to hell you have rubbers after all that teasing!"

"I do indeed!" I said, taking her hand and leading her up two flights of stairs and to my room.

As soon as we were in my room, she grabbed me and kissed me hard, pressing her tongue into my mouth. We fumbled with each other's clothes, quickly getting naked. She broke the kiss.

"Told you it was black!" she declared, taking a step back so I could look.

She did indeed have a tangle of black pubic hair. In fact, she was one of the hairiest girls I'd ever seen. She looked like the picture of Demi Moore that I'd seen in Penthouse a few years earlier; though Candace's bleached blonde hair that framed her face was quite the contrast.

"You did!" I grinned.

She gently pushed me back towards the bed and I climbed in, and moved so my head was on the pillow. Candace got into bed next to me and surprised me by quickly engulfing my dick, her lips touching my pubic hair. She released me and looked up at me.

"Like that?" she asked with a sly smile.

"What do you think?" I smirked.

Candace took me all the way in again, then began slowly sliding her tongue around as she moved up and down, fully taking me into her mouth each time. After a few minutes, she began twisting her head as she moved up and down, making the pleasure even more intense. She lightly raked her fingernails across my ball sack, causing me to thrust my hips slightly. The combined sensations of her tongue, lips, and fingernails brought me quickly to the point of no return.

Candace sensed my impending orgasm and rose up so that only my glans was in her mouth. With one hand, she stroked my shaft and the other she ran her fingernails over my balls. A swirl of her tongue and a soft suck caused me to fire a jet of cum into her mouth. She swirled her tongue faster, stroked me harder, and continued sucking as I spurted into her mouth.

When the last spurt had fired, she slowly released me and opened her mouth to show me the accumulated cum. She deliberately swallowed, ran her tongue over her lips and then smacked them. She smiled at me and put her head on my stomach. She watched my dick deflate and then began kissing my stomach, moving up to kiss my chest and lick my nipples. I groaned softly from the pleasure which caused her to re-double her efforts. She spent a good ten minutes kissing my chest and stomach before she gently sucked me hard again.

"Rubbers?" she asked.

"In the nightstand drawer," I said, pointing.

She opened the drawer and laughed.

She held up the tube of cherry lube.

"Naughty boy! And what is THIS for?" she smirked.

"Let me show you!" I grinned, grabbing the tube from her hands.

I pulled her to me, kissed her and then rolled her onto her stomach, positioning a pillow under her. I quickly spread the lube on my dick, then between her cheeks. I was pretty sure from her comment that she'd done this before. She didn't protest when I put my dick against her rear entrance and began pushing into her. She groaned and grunted as I worked myself into her tight butt.

When I was completely in, I leaned over and whispered, "That's what it's for!"

I began slowly stroking in and out, and Candace slipped her hand under her stomach and began rubbing her clit. After a minute, she begged me to go harder and then even harder still.

"Fuck me hard, Steve!" she groaned as I felt her muscles tighten as her first orgasm hit her.

I continued moving in and out as she rubbed herself to a second orgasm, which caused her muscles to clench tight and pushed me over the edge. I pushed all the way in as cum exploded from my dick into her butt. When our orgasms passed, I gently withdrew and went to the bathroom to wash up. After making sure I was completely clean, I went back to the bed and helped her turn over.

I kissed her softly on the lips, then quickly moved to begin licking and sucking her nipples. She moaned softly when I released one to switch to the other, then again when released the second one to kiss my way down to her mons. She smelled wonderful, but the thicket of pubic hair made it difficult to find her labia. I did find it and got a good taste of her sweet juices.

"Ahh! I hope you like licking candy!" she gasped.

I did indeed like the taste, but her pubic hair really got in the way. It was nice to nuzzle my nose in, but not so nice on my tongue when I searched for her clit. I found it and began gently sucking and licking. She bucked a bit, then using both hands, pulled my face hard to her crotch. Almost immediately, she moaned and bucked and had an orgasm. Sadly, it just didn't do anything for me to have a mouthful of hair, so I moved up and grabbed a rubber from the drawer.

I ripped open the package, rolled it on, and quickly buried myself in Candace. She wrapped her legs tight around me and we quickly built a fast, hard rhythm, kissing deeply as we pounded against each other. More than ten minutes later, with both of us gasping and sweaty, she came for a third and final time and I filled the rubber with cum. I grasped the rubber, pulled out, and got out of bed to dispose of it.

"Better than I expected!" Candace said when I got back into bed next to her.

"You had doubts?" I grinned.

"Hey, sex is like snow. You never know how many inches you're going to get or how long it's going to last!"

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