A Well-Lived Life - Book 5 - Stephanie - Cover

A Well-Lived Life - Book 5 - Stephanie

Copyright © 2015-2023 Penguintopia Productions

Chapter 31: Starting Over From Scratch, Part II

Coming of Age Sex Story: Chapter 31: Starting Over From Scratch, Part II - 2015 Clitorides Best Incest Story Winner! Relationships forged in battle are among the strongest bonds two people can have. In Steve and Stephanie's case, they've been battling their deranged mother together for years! From simple things like swimming together each morning, cooking meals together, double dating, and entertaining friends together, more than one person in their circle has commented it's almost like they're married.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Mult   Teenagers   Incest   Brother   Sister   First  

August 1981, Milford, Ohio

The kiss with Jennifer reminded me most of my kisses with Kathy. Kathy and I loved each other, but not the way I loved Kara or Bethany. She sighed when we broke the kiss and I saw a tear trickle down her face. I used my thumb to wipe it away. I wasn’t sure if it was from being happy, from the emotional situation in general, from the missing connection, or some combination of those.

“Thank you,” she said.

“You’re welcome,” I replied softly.

“Steve,” she said, looking directly into my eyes, “do you want to come upstairs with me?”

“Are you sure about that? It is our first date.”

“I know. That isn’t normal for me, but it feels right. I have to be honest with you. I’m not a virgin. I’ve been with two other guys. The first one was just once, and it was terrible. The second one was with the most amazing, attentive lover any girl could have.”

“I’m not sure I can measure up to that standard. Are you really sure you want to be with me that way? It is our first date, after all.”

“Yes. That’s what I want. I guess you have some experience?”

“I do.”

“Then come upstairs with me,” she whispered.

I set my bottle down, took her hand, and she led me up the stairs. She took me into her room and shut the door. She turned to face me and I took her into my arms. We exchanged a soft kiss, and I let her go. I realized that she had a ribbon in her hair, just like the first time we’d made love. I couldn’t remember the color, but I wondered if it was the same one.

I pulled the ribbon from her hair, letting her ponytail cascade around her shoulders. Her strawberry blonde hair was still intoxicating. Her green eyes still threatened to pierce my soul. My fingers went to the buttons on her blouse and I unbuttoned them one by one. I helped her remove it and I hung it on the back of the chair. I was shocked to see what I was sure was the light blue bra from four years ago!

I reached around for the clasp and released her bra. She shrugged the straps off her shoulders and let it fall into my hands. It joined the blouse on the back of the chair. Her breasts were just as I had remembered them. I took my finger and traced around the pink areolae and she shook a little bit. Small goose bumps appeared on her breasts, competing with her hardening nipples.

I looked Jennifer directly in the eye and put my hand on the button of her jeans. I had to make sure she was still OK with this. Seeing nothing but love in her eyes, I undid the button and pulled down the zipper. I put my hands on the small of her back, then pushed them down inside her panties, and cupped her butt. I pulled her to me and gave her a deep French kiss.

In one movement, I had her jeans and panties around her ankles. I knelt down to help her step out of them, my eyes exactly at the level of her wispy, strawberry blonde pubic hair and puffy labia, clearly wet with excitement. Just a touch of my lips to the top of her labia caused her to shudder. The jeans and panties stayed on the floor.

“You’re beautiful, Jennifer,” I breathed, repeating what I had told her that first time.

I stood up and kissed her again. Jennifer’s hands went to my polo, and she slowly began to unbutton it. She pulled it over my head and laid it across the back of the chair with her blouse and bra. She unbuckled my belt, unbuttoned my slacks, and then unzipped them. Like I had done for her, she pushed my slacks and underwear down together and I stepped out of them.

She put her hand on my rock-hard dick and squeezed. “It’s nice and big,” she whispered.

Letting go of my dick, Jennifer took my hand and led me to the bed, turned down the covers and climbed in. I followed her, and she pulled the covers up over us. We were side by side, facing each other, but I just waited.

Then it hit me, I had better be damn sure she was still on the Pill. I didn’t see her acting like Becky, but in her emotional state, something as simple as missing a day or two could lead to disaster.

“What about birth control, Jennifer? I have rubbers.”

“I’m on the Pill. I know it’s our first date, but I hope you trust me enough to believe that.”

And that was the question. It was a hell of a trust, but it would show Jennifer that I could trust her again. Not enough to think about a relationship, but enough to believe that she wasn’t trying to trick or trap me. I nudged her to her back and gently got on top of her, her breasts and my dick crushed between us. We kissed, and she wrapped her legs around my calves, just below my knee.

“Be gentle, Steve. It’s been a year since I last made love with someone,” she whispered in my ear.

I moved a bit so that the tip of my dick was against her labia and pressed forward. She was soaking wet and because she wasn’t a virgin, there was no resistance. She was tight, but that didn’t prevent me from sliding all the way in with a single stroke. It was as I remembered — she fit me like a glove. Not too tight, with just enough pressure and oh so silky smooth.

“Ahhh!” she gasped. “That feels so good.”

I started moving and despite not having felt the connection, Jennifer perfectly matched my movements and we were perfectly in sync, just as we always had been. When I went harder, so did she. When I slowed, so did she. I found it interesting that our bodies could still talk to each other just as they had done before, and now, without feeling the connection.

Jennifer had asked me to be gentle, which really didn’t surprise me, given that was how our very first lovemaking session had been. I alternated between slower and faster, harder and softer, but never pounding. I moved side to side and every few strokes, I kept our pubic bones in contact and used my hips to flex my dick. I felt the small spasms as she had her first orgasm.

“It’s wonderful, Steve!” she gasped.

I kissed her and continued to vary my strokes. After about five minutes, she squeezed me tight.

“I’m close!” she gasped.

No variation now, just sliding in and out. She wrapped her legs around my thighs and ground her clit into me. She groaned. It was not like the first time when she had screamed, loud and primal. But the orgasm was just as intense as I remembered. Her pussy started spasming, alternately clamping and releasing. I timed my thrusts to move when she was loose, and to be still when she was tight. She squeezed me hard, grunting and groaning. Suddenly I was there right with her, blasting her full of cum. Jet after jet.

When my orgasm finished, I returned to a slow, steady rhythm. She spread her legs even wider and rested her heels on my butt. I kissed her between panting breaths. She pulled me tight to her and mashed her clit hard into me.

She groaned and shook again. I kept thrusting as her orgasm washed over her. When she finally relaxed, I kissed her gently. She hugged me and we lay there, catching our breath. My erection subsided and eventually slipped from her sopping pussy on its own accord.

Jennifer patted my butt, and I got the hint to roll off her. She turned and put her head on my chest. I wrapped my arm around her and cuddled her. We lay together for about ten minutes.

“Will you stay the night?” she asked.

“Of course,” I said.

“It was a wonderful first date. The best I’ve ever had. And you are the best I’ve ever had!”

“It was wonderful!” I said, pulling her tight.

She fell asleep quickly, and I lay there, lost in my thoughts. My first impression had been correct. Sex with Jennifer now felt very much like sex with Kathy. It was, for lack of a better word, comfortable. That eased my mind a bit because I could tell Kara she had nothing to worry about. For sure, Jennifer and I were on a new path, a new journey, but I didn’t have the same feelings I’d had for her. I was pretty sure that’s what had happened to the connection.

The physical, emotional, mental, and even spiritual components of my relationships dictated the intensity of the connection. It had been strongest with Stephanie, though it had peaked and fallen rapidly. With Kara, like Birgit, it was intense and growing. Through that one special night with Karin in Stockholm, I’d had a semblance of what might have been. Jennifer, before the deceptions, and Karin were close, but couldn’t approach the others. Bethany and Pia were next, but not nearly as strong.

I felt pretty good about things, which, of course, concerned me. My history said that just when I thought everything was going well, something would muck it up. I’d be leaving for Chicago in four days, but that was more than enough time for something, anything, to bring my world crashing down around me. It wasn’t a premonition, more like resignation. I knew I’d have to get past that feeling if I wanted my life to be happy. I eventually fell asleep with all of these things going through my mind.

I awoke early the next morning with Jennifer’s naked body against mine. Even though my bladder was protesting, I didn’t want her to wake up with me, not in the bed. She and I needed to have a long talk, without the fiction of the first date that we had used to get to this point. Of course, I had told her that it really wasn’t fiction, but that didn’t remove the need to talk. Jennifer stirred about twenty minutes later.

“Hi,” she said with a smile, snuggling close.

“Hi. How are you feeling?” I asked.

“I’m fine,” she sighed. “But I had nothing to lose. How are you?”

“I’m OK. We do need to talk, but I’m sure you realized that.”

“Yes. What time is it?”

“Just before 6:00am. We can talk before breakfast. Let me go use the bathroom and I’ll be right back.”

“I need it as well,” she said.

I got up and put on my robe. Jennifer did the same thing, and I suppressed a chuckle when she followed me. I lifted the seat and urinated, then flushed the toilet and lowered the seat. Jennifer sat down and relieved herself. We both washed our hands and went back to the bedroom. We kept our robes on but sat on the bed, leaning against the headboard.

“Thank you for trusting me enough to make love to me, Steve.”

“I think it was the idea of the first date that made it possible. I noticed you were completely honest about your history. Are you turning over a new leaf?”

“Yes. With you, I have to be a completely open book. Nothing held back. Ever. I know that has to be the case if I want to be your friend, much less anything else.”

“What was that tear about?”

“I was so happy you kissed me that I couldn’t help it. I just wish I’d been as honest with you during our Freshman year as I was last night.”

“That was interesting. So, I have to ask, how did I measure up against that amazing, attentive lover?” I said with a grin.

“Oh, you did fine,” she giggled. “But you know what? That previous guy? He was nothing like you. In fact, despite being an awesome lover, he was a real jerk at times.”

That last part was delivered without a smile or any indication that she was teasing. Of course, she was right.

“Really?”

“Yes. Very often, he was a needy, whiny, angst-ridden, drama-filled, self-centered prick,” Jennifer said seriously.

Which, I could admit now, was true. Bethany and Joyce had tried to tell me in their own way, but I hadn’t listened.

“And I’m not those things?” I asked gently.

“I don’t think so. Dropping all the pretense, you aren’t the same person I knew in August of last year. I think Kara’s been good for you, very good. And, don’t take this the wrong way, but losing to her is fine. Anyone who can make the radical changes in you that she has deserves you, Steve.”

“Are you foreclosing a future with me, Jennifer?” I asked, making sure I kept my voice neutral.

“Oh no, not at all. I think you’ve closed that door, though maybe, just maybe, I have a toe keeping it from slamming shut. What I’m saying is that I can see why you feel the way you do and how good she is for you. It was something I could never do for you because I lied and hid things from you from the beginning, and I guess that made me act irrationally.”

I smiled, “You know what? All of this, all the stuff that happened with you and me, with us, all of it, proves Birgit was right. She knew exactly what she was doing, and she was exactly right. I’m just sad she didn’t live to see it.”

“What do you mean?” Jennifer asked.

“She told me that I had to live my life and, in effect, grow up before we could have a relationship like she wanted to have with me. If I had simply slapped a coat of shellac on my eighth grade self, where would I be? Certainly not here, where you could call my old self a selfish prick and I could agree with you.”

“Actually, I called you a needy, whiny, angst-ridden, drama-filled, self-centered prick,” she giggled.

“Yes, you did. And, may I say, that you were a dishonest, lying, phony bitch?”

“Yes, you may, because it’s true. I was. Not any more, Steve. Not after these last few days.”

“The girl I saw last night, the girl I went on a first date with and made love with, was a very different girl than the one who went to Seattle a year ago. In fact, she’s a very different girl than the one who smugly told me that she’d lied to me for months.”

“And do you know why that is?” she asked. “It’s because you cared enough for me to want to help me.”

“I do care. But you know things have changed dramatically since you left.”

“I know,” she said sadly,” but I also know that if we had continued the way we were, it would have ended in disaster at some point. The nightmare would have been to have faked it long enough to get married and have kids. Then what? No. What happened was for the best. I see that now.”

“Wow, Jennifer, this is a pleasant surprise.”

“For me too,” she said. “Last night was like making love, really making love, for the very first time. I was open and honest and you knew who I was and I knew who you were. I mean, clearly, we weren’t virgins, but there was something different about sex with you last night. It actually meant more to me than any time we did it before.”

“I think that’s because of the honesty. It makes all the difference in the world.”

“I guess that’s it. It certainly wasn’t the ‘connection’ because I didn’t feel that. That made me sad, but then I realized that after everything I had done to you, there was no way it could be there.”

“It wasn’t just you, Jen. I did a lot of bad things to you. I never, ever put you first, to the exclusion of all others. I was trying to have my cake and eat it, too. But forget all that. It’s in the past now. As for the present, I want you to think about the last couple of days. Think carefully now. Is the connection truly gone? Or just different?

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