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

A Well-Lived Life - Book 8 - Stephie

Copyright © 2015-2023 Penguintopia Productions

Chapter 17: A New Start

Coming of Age Sex Story: Chapter 17: A New Start - 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  

March, 1983, Chicago, Illinois

We chatted amiably for the forty-five minute drive to the apartment. I found out that Rosie was the oldest of three kids, the other two being boys, and that she'd graduated near the top of her class. She'd dated some in High School and had gone to both her Junior and Senior Proms, but with a different guy friend each time. She had taken some ballet when she was little, but quit once puberty started and her body shape didn't work. She rode horses and enjoyed riding, though she rode English where all my experience was Western.

"You ride?" she asked, perking up and sounding normal for the first time.

"I did. I learned when I was six and rode up until after I turned fifteen, but I haven't been riding in the last four or five years. I'd love to go again."

"There's a stable out in Naperville where I ride sometimes. Maybe you can come along!"

"If they have Western tack, sure. I've never ridden English."

"They do. I'm one of the few who rides English. I jump a little, but mostly I was learning to show when I was back home."

"That's cool."

"That's how I met my first real boyfriend. I was twelve, and he was thirteen. We met at the stable. It's not like we could do much, but we kissed and stuff. Then he met a girl who had a way better body and dumped me."

I shook my head, "Guys who only go for looks are not cool in my book."

"And you don't? Becky is really gorgeous! And so was that Indian girl at the party."

"There's more to it than just good looks. First of all, my type is not the ample-chested, airhead cheerleader. I prefer cute to pretty, and you're cute," I said.

"Me? But I'm flat-chested and dumpy!" she said.

"You have a cute face, nice eyes, and I like your hair. As for the other stuff, as long as all the parts are in the right places and work, I won't complain!" I said with a smile.

"You really mean that? I mean, there were guys back home that would go out with me, but it felt like they were doing me a favor and expected something in return."

"That's the lowest of the low," I said with disgust. "Guys like that give all guys a bad name. I never make any assumptions about anything. Ever. And that includes what's going to happen this evening."

"What?!" she exclaimed, a confused look on her face. "I asked you to take me upstairs at the fraternity house and then asked you to take me home with you!"

"You did. And all that means to me is you wanted to go to my room or to my apartment. Nothing more. Sure, lots of guys would assume that meant you wanted to have sex, but not me. The thought would cross my mind, obviously, but I would never assume that to be true."

"You're strange, you know that?" Rosie said.

"Yes, I've been told that before. And there's a very good reason. My best friend, a girl I've known now for almost six years, was raped when she was thirteen when she left a party by a boy who offered her a ride home. She taught me about consent and never making any assumptions. It's good advice and I follow it as best I can."

"Guys get mad if you don't do things with them! They call you a tease and complain that it's not fair if you don't give them 'relief'." She made air quotes when she said the last word.

"What's not fair is them assuming that taking you out means that they are entitled to a kiss, let alone anything else! Those guys are «некультурный», as my Russian friend would say — uncultured, uncivilized barbarians. Those are the kind of guys that give all of us a bad name."

"You have a Russian friend? That's cool!"

"Actually, several. I also have quite a few Swedish friends, because I lived there for a year. And a good friend from Spain that hangs out with us on the weekend."

"Us?" she asked.

"My roommates and friends," I said.

"Oh. Are they home?" she asked.

"Not until tomorrow. There's nobody at my place now."

"Why did you live in Sweden? Was your family there?"

"No, I was an exchange student for a year. I've been back once and I'm going again this Summer for a friend's wedding."

"Cool! Are you in it?"

"Yep," I replied. "I'm the Best Man."

We talked about my year in Sweden until we pulled up in front of the apartment building. Rosie commented about how nice it looked, and when we went inside, she was even more impressed. I took off my shoes by the door and she followed suit.

"You're nineteen and you have a nice place like this? That's amazing! And this is your stuff? All the computers and the stereo and the TV and the tape player thingy?" she spoke quickly and nervously.

"Yes," I said. "I do have a couple of roommates, but it's almost all my stuff. Elyse's stuff is in her room, though the computer in her room is mine, too."

"Elyse? Your roommate is a girl? But you said roommates. Isn't this a two-bedroom apartment?"

"Yes," I said. "Elyse has her own room, but Stephie shares one with me."

"Hang on!" she said, sounding exasperated and upset, and putting her hands on her hips. "After everything you said, you're cheating on a girl?! Really?!"

"Relax, please. I'm not cheating on anyone. I don't have a steady girlfriend."

"But you're living with a girl, well, two girls!" she protested.

"Yes, I am. And I just came home from visiting a girl in Boston. I'm not tied down to anybody. And Stephie won't be angry with me if this leads to anything."

"You're not just feeding me a line?" she asked, backing up a bit from where she had been standing next to me.

"No, I'm not feeding you a line. Everything I've told you is true," I said, then stepped back, turning. "Can you wait just a minute? I need to call my friend in Boston and tell her I arrived home safely."

"Sure," she said.

I went to my room and called Tatyana to let her know I was home safe. We talked for just a moment and then I went back to be with Rosie.

"Are you some kind of Casanova?" Rosie asked.

"A womanizer? I don't think so, but I guess I'm not the one to judge that."

"That's the popular idea of Casanova, but not really what he was about. He had lots of women, but he liked the chase. And he would rescue damsels in distress, and then, when they were grateful, he'd seduce them. Eventually, he'd claim he was unworthy and marry them off to worthy men, then move on."

I chuckled, "Melanie, Kathy, Mary, and Katt."

"Huh?" Rosie asked.

"Four girls that I dated that I fixed up with other guys!"

She laughed, "So it fits. Have you read any of Histoire de ma vie?"

"Uh, no. Should I check it out from the library?"

Rosie laughed again, "If you have a couple of years to read it. It's over 4,500 pages! I only read small parts of it for an honors literature class my Senior year of High School. Anyway, Casanova isn't anything like the popular idea of him."

"You seem more relaxed," I said with a smile. "That's a good thing."

"Well, talking literature, or horses, is relaxing for me, and I guess I feel comfortable with you," she laughed. "Do you have anything to drink?"

"Coke, Dr Pepper, 7-Up, and Root Beer," I said.

She laughed again, "Uhm, I meant like a drink! You know, like vodka or something."

I nodded, "Vodka, bourbon, sloe gin, red and white wine, and regular gin."

"I'd like a sloe screw," she smirked. "But I'll settle for a Bourbon and Coke."

I laughed, then poured a shot of bourbon into a lowball glass, added a couple of ice cubes and then filled the glass with Coke. I poured myself a neat bourbon and took the drink to Rosie, indicating she should sit on the couch. She took the glass and sat down. She took a big gulp, but then sipped slowly. I turned on the stereo and then sat down on the other end of the couch.

"Rosie, why are you here?" I asked.

She took another big gulp of her drink, looked down, then up at me and smirked, "A slow screw, like I said before! I want to get laid."

Well, that was direct and to the point. I was no longer so sure that she was a virgin, in fact, the things she had said sounded like she had 'put out' for some of the guys who expected her to. Asking her that question wasn't really appropriate, at least not as a direct question. Of course, if I did as she wanted, I'd find out soon enough, or perhaps not, because of the horseback riding. But it didn't really matter much, and I'd deal with that when and if I needed to.

I said 'if' to myself because I wasn't sure yet that it was the right thing to do. Yes, she'd clearly stated what she wanted, but I wanted to make sure this wasn't going to end with her deciding it was a mistake, or worse, thinking that she and I could have some kind of relationship. And that gave me pause as well, given the guys who she'd been out with that had basically used her. It was that last thought that really gave me pause.

Rosie looked at me with an odd combination of desire, nervousness, awe, and fear.

"I'm a bit concerned," I said gently. "You know I can't offer you a relationship, and I'm afraid you might regret it or feel used afterwards, especially with what you said about those guys with whom you went out."

"But I asked you," she protested softly. "You didn't ask me."

She nervously downed the rest of her drink. I wasn't going to give her another one, because I didn't want her judgment clouded.

"That's true, but sometimes people do things they aren't sure about, or even if they are, later regret it. You also told me about guys who used you, expecting you to have sex with them."

"But you weren't expecting me to have sex with you! Even when I asked you to take me to your room or bring me here last Friday!" she said, obviously concerned that I might reject her. "I just want to get laid, Steve!"

"If you're absolutely sure, then slide closer to me," I said.

She set her empty glass down on a coaster on the table and slid next to me. I set my glass down next to hers and before I knew what was happening, she had me in a lip-lock, forcing her tongue into my mouth. A couple of seconds later she shifted and threw a leg over me and was kneeling, straddling me, kissing me hard. I overcame my shock and put my arms around her and pulled her against me. Rosie moaned softly and then broke the kiss, gasping.

She pulled her sweater over her head and threw it on the floor, then once again engaged me in a fierce French kiss. All the signs of nervousness were gone, replaced by some sort of primal, carnal desire. She scooted forward and ground her pelvis against me, and moaned softly once again. Her fingers went to the buttons of my polo shirt and when she'd unbuttoned them, she broke the kiss and swiftly pulled the shirt over my head. It joined her sweater on the floor next to the couch.

She kissed me again, and I took the hint and unbuttoned her blouse. She quickly shrugged it off, revealing a pink lace bra covering her very small breasts. She didn't wait for me to move, but quickly unhooked her bra and pulled the straps from her shoulders, tossing it on the floor. She finally broke the kiss again, gasping for air while continuing to grind against me.

"Birth control?" I gasped, reeling from her aggressiveness.

"I'm on the Pill!" she said, sliding off me onto the floor.

She unbuckled my belt, unbuttoned my slacks, pulled down the zipper, and then hooked her fingers in my underwear. I took the hint and lifted my butt from the cushion and she pulled my pants and underwear down in a quick motion. She stood up and unbuttoned her jeans and then pulled them and her pink lace panties down and stepped out of them. She urged me to scoot forward and straddled me again, wrapping her legs around me. She pressed her body hard against me, trapping my dick between us, her small breasts mashed into my chest. She kissed me again, and used her tongue to explore every inch of my mouth as she ground her soft, blonde pubic hair against my raging erection.

I was sure now that I'd been wrong about her being a virgin. She might have been shy and nervous at the party, and even when talking about it, but she kissed like someone who'd kissed quite a lot and she'd said that guys had expected sex from her. She rose up, grasped my dick, and rubbed my glans along her moist labia. Without warning, she pushed down hard and groaned into my mouth as half my length went into her. I thought I felt a hymen give way, but it had to be my imagination. She rose up again a bit and pushed down hard, fully embedding me in her very tight, very hot tunnel.

I put my arms around her and held her tight as we kissed furiously and she began moving back and forth and grinding against me. Rosie moaned constantly as she began moving faster, humping as hard as she could in our position. I held her tightly and let her build her orgasm, which came perhaps a minute later. Rosie's body shook, her pussy tightened further around my shaft, she broke the kiss and screamed.

With her orgasm barely over, I held her tightly, stood up, and then laid her on the floor without my dick moving from her steaming folds. I propped myself on my hands and began slowly thrusting in and out, then sped up as she matched my strokes by raising her hips. A minute or so of urgent thrusting brought Rosie to her second orgasm, though this time she simply groaned. When it passed, she begged, "More!" as she gasped for breath.

We continued for another ten minutes, with Rosie constantly begging for more. After her fifth orgasm, I slammed hard and deep and fired several strong spurts of cum into the depths of her pussy. Rosie ground her clit against me through my orgasm and when my own orgasm passed, I bent down to kiss her softly — the first soft kiss we'd exchanged. I gently pulled out of her and rolled on to my back next to her.

"Thanks," she whispered. "That was amazing!"

"It certainly was! I was surprised," I said, still catching my breath. "But if that's what you needed, that's fine."

"Can we do it again?" she asked.

"Sure, I just need a bit of time to recover. What time do you need to get back to the dorm?"

"I brought my toothbrush and clean underwear. I hope you'll let me stay the night. I just need to be back by noon."

I chuckled to myself, thinking just how silly I'd been to think this girl was a virgin. I had equated shyness with inexperience and misjudged the entire situation. The rest of the night was going to be a lot of fun. Once again, I'd found a girl who was overlooked by most guys because of her personality and her body. I was pretty sure that losing a bit of weight would change all that, but it wasn't the time to suggest that.

"I need a glass of water," I said, wiping sweat from my brow.

"Me too," she agreed.

I went to the kitchen and brought back two glasses of ice water, and handed one to Rosie, and we both drank some.

"Talk about the best possible first time!" she exclaimed.

That was a real surprise, and maybe I had felt something give way, but I didn't see any blood.

"Rosie, why didn't you say something?" I asked.

"I told you why I came here! I wanted to get laid! I thought you'd realized that!"

I chuckled, "I thought I did, but then after everything you said, and then the way you behaved, I figured that I'd made a bad assumption."

"I was so nervous that I decided I would just do it and not think about it! If I hadn't, I might never have been able to do it. Guys in High School wanted it, but I was so nervous that I couldn't. I kissed a lot, and I gave some handjobs, but that's it. They never wanted anything but for me to make them cum, so I did."

I nodded, "Are you feeling OK?"

"Yeah, it didn't hurt like some girls said, and I didn't bleed, and, well, oh, wow! I've rubbed myself to orgasms until I was almost raw, but they were nothing like those! Can I have more?" she asked, tilting her head and smiling coquettishly.

"Sure," I said. "As much as you want. Well, within the physical limits of what I can do, but I think I can provide!" I said, sticking out my tongue and wiggling it.

"Oh! Nobody's ever done that to me! My best friend in High School said her boyfriend did it to her once, and she thought she'd die!"

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