A Well-Lived Life - Book 2 - Jennifer - Cover

A Well-Lived Life - Book 2 - Jennifer

Copyright © 2015-2023 Penguintopia Productions

Chapter 35: She Had No Idea What She Was Missing

Coming of Age Sex Story: Chapter 35: She Had No Idea What She Was Missing - Following the dramatic end of Book 1, Steve is reeling from the devastating news he and his closest friends received. With their help, he begins to pick up the pieces and come to terms with the heartbreaking aftermath. Even as his body count of girls at Milford Junior and Senior High continues to rise, he develops several relationships that will drastically affect the direction of his life, starts a computer programming business and becomes aware of his little sister’s deepest secret.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   ft/ft   Mult   Teenagers   School  

November 1978

During my usual morning routine of swimming, shower, and breakfast, I mulled over my thoughts from the previous day. I saw three very distinct futures with three very distinct lives. If I had to characterize them simply, Joyce represented stability, Jennifer adventure, and Becky passion. Each girl had a mix of those traits, but each one was dominant in one of them.

I had no doubt that each of them would make a wonderful wife and mother, but each represented a far different life. At fifteen, I had no idea which life I wanted. My parents had an odd relationship that I had never figured out. What I was certain of was that I would never be anything like them.

In fact, if I was going to be like anyone, it would be Melanie’s parents. They were the most accepting, open-minded, loving parents I knew. What concerned me there was that even with that, Melanie had tried to kill herself. I had a terrible relationship with my mom and the thought had never crossed my mind. It made no sense.

My mind having gone to the Spencers, I remembered that if all went well, Melanie would come home later in the day and Jennifer and I would spend Sunday with her. I had let Beth know that was likely, and I’d call her if that didn’t happen. I still hadn’t heard from Doctor Grossi, but I assumed he would call soon.

Dad dropped me at work and would pick me up later when I called him. As soon as I walked in, I was instantly occupied with tasks that didn’t allow me to think too much. Andreas had me doing a complete inventory and preparing the order sheets for our suppliers. Once I finished that, I started putting together the lunch orders for delivery. The weather wasn’t very good, so Kim would make the deliveries because she could drive. When she got back, I got my lunch and sat down to eat.

“No girls today?” Kim observed.

“No girls. Just you!” I teased.

She stuck her tongue out at me.

“Don’t stick it out unless you plan to use it!”

“Give me a chance and I will,” she offered suggestively.

That was seriously differen from how she’d said it in the past. I realized that my tomboy friend had turned into an actual girl! She still had her frizzy perm, but now had a figure. I suddenly saw her in a new light.

“If you’re serious, next Saturday after work.”

“You’re on!” she said as she went back to work.

The dynamic between us had just seriously changed. I didn’t think she was thinking about playing catch or baseball, though the base metaphor might apply.

During the afternoon, I restocked the display cases and ran the register. That gave me more time to think. Jennifer, Joyce, or Becky. Which future did I want? Did I know? Was I willing to foreclose any of them? I realized I had made Becky not just a remote possibility, but an actual consideration. I wondered if I could have a closer relationship with her without all the old issues rearing their heads. I had Jennifer’s permission to have sex with Becky. I was sure I didn’t have her permission to become involved with Becky. I was sure of one thing, though, and that was that Becky and I needed to talk.

Those thoughts swirled in my mind. I kept coming back to needing to explore all the options. To find out what I really wanted. That’s part of what being a teenager was. Figuring out what you wanted to do with your life; figuring out what you needed from life. I was pretty sure my career was with computers, with or without the relationship with Don Joseph. Beyond that, I didn’t know.

It occurred to me that if I had to decide right now, without any further input, I’d probably chose stability over passion and adventure. After the insane events of the past eighteen months, of the wild roller-coaster ride that I had been on that had brought me to soaring heights and plunged me into murky depths, stability seemed the best choice.

I also realized that of all my relationships, the one with Joyce was the calmest and least prone to wild swings. It was the most comfortable as well. I had a visceral reaction to the notion that Jennifer might have sex with someone, but had reacted quite differently with the revelation that Joyce had actually had sex with someone.

Of the three, Joyce made the fewest demands on me and set the fewest restrictions. Unlike Becky and Jennifer, she came with no pre-conceived notion of a relationship. She basically let it define itself. She was comfortable with it. She let things flow, accepting that in the end, Fate would bring us to the right place.

I shocked myself by mentally placing Joyce ahead of Jennifer as the most likely life partner. Her approach had been subtle. It didn’t seem like a conscious plan, but rather just who she was. She took her time, got to know me, and then simply started taking care of me before we even got beyond kissing.

I wasn’t making any kind of final decision. I still had to finish High School, including a year away, and go to college. A lot could happen in that time. I wondered now if I was wise to have promised Jennifer a promise ring. Did I want to shut out those options before I had to? It was more than a year away, so I didn’t have to deal with it now.

I looked at the clock and realized the day was almost over. I quickly finished my tasks and just before 4:00pm, I prepared a couple of sandwiches, grabbed a couple of bags of chips and four Cokes, and packed them up. At 4:00pm, I finished up and went outside to wait for Kathy. Kim got in her car and drove away.

About 4:10pm a car drove into the lot, stopped and Kathy got out, carrying a gym bag. She walked over to where I was sitting.

“Hi!” she said. “I Love the fedora.”

“Hi! Thanks.”

She just looked at me expectantly. I got up and motioned for her to follow me.

“Where to?” she asked.

“Someplace we can sit and talk in private.”

“Talk?” she smirked.

“Yes, talk.”

She had a confused look on her face, but said nothing. We walked towards the apartment building and when we came to the lobby door, she stopped.

“Where are you taking me?” she asked, a bit nervously.

“My boss has an apartment that he doesn’t use very often. I have a key. We can talk and eat and nobody will bother us.”

“OK, I guess,” she tentatively agreed.

We went in and went upstairs and I let her into the apartment. I slipped off my shoes and then put the food in the fridge, then turned on the radio and sat down at the couch. Kathy came and sat on the couch, but not close.

“What’s going on?” she asked. “I thought this was about sex.”

“It is. But not sex like you have; sex like I have. And that starts with talking.”

“I don’t get it.”

“I know. That’s the point, isn’t it? Tell me what happened at your party.”

“I offered to have sex with you, you started, then got mad and told me to get dressed. You said that you had better sex jerking off than I was offering,” she said, her brow furrowing as some anger crept in, remembering that moment.

“Yes, that’s basically it. But you were just lying there, not enjoying it, not doing anything.”

“So? The guys just do their thing and they’re happy. Nobody ever treated me like you did!”

“That’s because what you offered wasn’t even remotely like what I think sex is. Sex isn’t about just putting a penis in a vagina and ejaculating.”

She giggled, “Uhm, yeah, it is. That’s how it works.”

“Kathy, you and I kissed. Do you think that kiss was the same as the one Bethany and I shared?”

“I guess not.”

“You and I have had mutual crushes for over two years, and our kiss was, well, average at best. Bethany and I were never in love, aren’t even seeing each other, and our kiss had way more passion. Should that be the case?”

“No, I guess not.”

“I offered to show you what it can actually be like. What it should be like. But you have to want it.”

“I’m here, aren’t I?”

“That’s true. And I have to say this presents an odd situation for me. You see, for sex, I only really get pleasure out of pleasing my partner. That’s where my focus is. That’s why I stopped at your party. I saw that I wasn’t going to get any kind of fulfillment from it. I know I hurt you by saying it, but it was true — it was almost like I was masturbating.

“The dilemma is this — if you really want to know what it’s about, you have to focus only on your own pleasure. Pretty much the opposite of what I usually would tell someone. If we’re going to do this, that’s what I want you to do. Just focus on your own pleasure. I’ll focus on your pleasure as well. I’m pretty sure you’ll see the difference.”

“But guys don’t care. They just want to get off.”

“Then you are with the wrong guys. You said you never had an orgasm with a guy. I assume you’ve had at least one, though.”

She giggled, “Yes.”

“OK. So you can have them.”

“All that stuff you said during the ‘Truth or Dare’ game, and afterwards, is that really all true?”

“Yes,” I said. “I’ve been with fourteen girls — I should have said thirteen at the party, I miscounted. You were technically the fourteenth, but I’m not sure what we did really counted. I’ve had a threesome and a foursome. I’ve done just about anything you can imagine. And I have never, ever failed to bring a girl to orgasm at least once.”

“Wow. I never suspected any of that. I guess nobody did, given the reactions.”

“That’s because I don’t talk about it. With the exception of Jennifer and my friend Melanie, who know everything, I’m pretty circumspect. I never, ever talk about this stuff with my guy friends and I never brag. Ever. Any rumors you hear are from girls, Kathy, not guys.”

“I never believed the rumors. I guess they are true.”

“Yeah. So, back to your problem. When you mess around, do you do anything more than what we did? Or is that usually what you do?”

“That’s usually it — just kissing, then he does it and we’re done.”

“You have no idea what you’ve been missing.”

“Katy told me that, but I always thought she was just trying to make it sound like her boyfriend was really good.”

“Well, Jennifer and Bethany told you the same thing, didn’t they?”

“Yes.”

“Before we move forward, there are some ground rules. First, you know Jennifer and I are pretty serious, so no matter what happens today, this is a one-time thing. Second, we do things my way. If you want to stop, we’ll stop, but that means we’re done. Third and last, you have to be honest and open about everything we do.”

“Jennifer warned me about the one-time thing. Yeah, fine.”

“Let’s eat first, OK?”

I got the food out of the fridge and we sat down to eat. We didn’t say much while we ate, but we did talk a bit about school. She hadn’t got her driving license as yet, because she hadn’t finished Driver’s Ed. I told her that I hadn’t decided if I was going to bother getting mine because I’d be going to Sweden for a year. That led to a discussion of my plans for the exchange program.

When we finished, she excused herself to use the bathroom, taking her gym bag with her. A couple of minutes later, she came out, and I started chuckling. Kathy was wearing her red and white Milford Eagles cheerleader’s uniform!

“Jennifer put you up to that, didn’t she?”

“Yes! She said it would turn you on.”

Jennifer was right. I had dropped that hint, hoping it would happen. I needed it, because despite having a two-year crush on Kathy, what happened at her party had really turned me off. As cute as she was, as much as I liked the shocking red pubic hair, I had developed a really negative picture of sex with her in my mind since the party. I also realized that had ended my crush on her as well. My fantasies about her had basically been crushed by that one incident.

It also dawned on me that Jennifer realized all of that. She also knew that the fantasies and crush might be revived if this turned out well. That’s why she put the ‘one time’ restriction in place. It kept everything safe.

I got up and took Kathy’s hand and led her to the couch. I took both her hands and looked into her eyes.

“Kathy, remember, do this because you want to, not because the guy wants you to. Let him know by everything you do that you want it at least as much as he does, OK?”

Without waiting for an answer, I pulled her into a cherry-flavored kiss — she had clearly put on lip gloss. Our lips parted, and we began chasing each other’s tongues. This kiss seemed better than the ones at her house. I broke the kiss and planted a few small kisses on her neck and then returned to our previous French kissing. We kissed for another few minutes until she broke the kiss.

She had a somewhat confused look on her face and I realized she wondered why I wasn’t escalating! It dawned on me that one of her problems was that she rushed right to screwing. Basically, a few kisses, a quick grab of her naked breast and she was naked on the couch and I was in her. I had some fault in that, but I should have slowed things down. I absolutely needed to take my time now.

“Another important thing,” I said. “Sex is about the journey, not the destination. We know where it ends up, but getting there is all the fun! Let’s just keep kissing for a bit, OK? We have plenty of time to screw as many times as we want.”

She just stared at me and I pulled her back to me and we continued to kiss. After several minutes, I began running my hands over her back, and occasionally over her skirt-clad butt. Her kisses were becoming more passionate and her pulse had picked-up a bit. I slowly moved my hand up her side and then cupped her breast through her sweater. The thick material made it hard to feel her nipple, though I was sure it was hard.

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