The Jenna Arrangement Pt. 13

I smiled and hugged her still sweaty body closer to mine. "For someone so young, you have a really mature outlook on all of this."

Jenna shrugged. "I don't know about that. But I do know that what happened with my dad taught me that life is too short to live it unfulfilled. I don't wanna look back and regret things undone because I was too afraid to try."

Jenna's words made me reflect on my own life at the moment. Stuck in a job I didn't like all that much, alone and until recently friendless, afraid to go out and try something new, or get close to anyone. Maybe it was time I stopped living in fear, too, and started making some changes.

Jenna broke my train of thought by pecking me on the cheek before climbing out of bed. "Gotta go pee again; I always seem to have to pee after sex. Guess I'll wash my face, too, so I don't stain your pillow case," she giggled.

Watching her naked ass recede from view as she left the room made me wish I was a much younger man, with the energy to take her one more time. But twice in one night, plus our masturbation session this morning, was not too shabby I suppose, although it left me now utterly spent, even a little sore. Worth it, though, no complaints.

I was once again contemplating what changes lay ahead for both of us when Jenna returned from the bathroom. Her face was scrubbed free of both my cum and the makeup she'd been wearing earlier, leaving her freckled young face fresh and radiant. She climbed back into bed and once again shared her warmth with me, snuggling up close.

"Looks like something's on your mind," she said. "Wanna share?"

"Just thinking about the future," I said. "Mine, and yours. What do you want to do after college?"

Jenna thought for a few moments. "I want to work as an illustrator. Maybe for books, or storyboards for films. I think I'd find that more creative and fulfilling than, say, advertising or something. There's some internships I'm gonna try out for next year with some local graphic design companies, get some field experience. It's another reason I've considered Only Fans; that will take a lot of my time and they don't pay. I'm also adding some computer courses, learning how to render 3D art and things like that. After school I'll start submitting my portfolio to various places and see what happens."

I felt a mix of emotions at that moment. Jenna had such a bright future ahead of her, and I was happy for her. But I also understood clearly that it was going to be difficult for me to remain in it for long.

Jenna sensed my feelings. "Hey, I know what you're thinking. But can we just be happy together while it lasts?"

"Of course," I nodded, "I knew what I was getting myself into. And I know it may not work out for us in the end. I'm a realist. The last thing I'd want to do is hold you back from your dreams and future for my own selfish needs."

"You're not being selfish," Jenna chided me gently. "We didn't expect or plan this. Look, let's be honest; neither of us went into this expecting to 'catch feelings,' we both were just looking for a fun sexual outlet. But here we are.

"I do love you, care about you, very much. And I'd never want to hurt you. How this all works out for both of us depends on so many things, I can't even fathom them all. I just know that, right here and now, I want you in my life. The rest will sort itself out over time."

Jenna snuggled into me, kissing me yet again. "Let's enjoy what we have, and be happy for it."

"I can do that," I sighed contentedly.

"I'm thinking about going back to school," I confessed suddenly. Jenna gave me a surprised smile. "Really? What for?"

"I...haven't decided yet," I replied. "I'm a little too old I think to start career hunting again, and while my job isn't all that fulfilling, it pays well enough and I have some seniority there. But maybe I can learn something I can use as either a part time thing or at least a hobby. I'm really not sure of anything yet, just thinking about it."

"Self improvement is always a good goal," said Jenna. "If I can help with that in any way, let me know." I nodded gratefully. "I will, thank you."

Jenna ran her hands lightly through my chest hair. "So, besides a threesome, what other fantasies do you have? Even your craziest, something you know would never really happen?"

I laughed softly. "How much time do ya got? Okay, here's one: in reality, I'm not really an orgy guy. I don't think I could handle it. But have you ever seen those videos with the male strippers, dancing around the room naked at an all female party, with a bunch of women jerking or blowing them? I've fantasized about being one of those guys, having dozens of women in one night touching and sucking my cock."

"Yeah, I've seen them," said Jenna. "I've fantasized about attending one of those, being a woman in the crowd. In my fantasy, sometimes I'd suck them off, but usually I'd get off more on the idea of them just cumming on me. I'd never do it in real life, though. Although I suppose I could enjoy just watching."

"Have you ever heard of a CFNM party?" I asked. "Those ones where the women basically just gather for a social type thing but have a naked man, or several naked men, acting as servers and waiters? Not actually having sex with them or anything, maybe only going as far as touching them a bit, but otherwise it's strictly just to look."

"Yeah I've heard of that too," smiled Jenna. "That sounds more my speed. Some male strippers flailing their cocks in my face isn't all that appealing, but watching a guy walk around naked in a room full of women, looking at him, knowing he wants us to touch him but we probably won't...yeah, that could be...fun."

"Well you've already done that sorta thing with me several times already," I joked. Jenna laughed in response, "I suppose I have, haven't I?"

"So what else besides CFNM stuff gets you off?" Jenna asked. "When you're surfing porn to jack off to, what's the craziest stuff that gets you going?"

I had to think for several moments. It felt almost odd to be discussing these things; none of the women I'd been with in the past seemed the least bit interested in talking about it. It was the stuff most men kept private, and most women didn't want to know. But Jenna was so casually open about it all that I felt comfortable enough to confess things I'd normally never say.

"I like those videos of the women in those private rooms at some whorehouse or whatever it is. Guys come in and fuck them through holes in the wall. They can wander around and fuck random pussy. Have you seen those?"

"I have," she said, "always wondered where the hell those places were. Probably somewhere in Europe."

"Probably," I agreed. "The idea of anonymous, disconnected sex like that can be appealing as a fantasy; like having sex with a pussy with no body, no person attached you have to worry about."

Jenna nodded. "I feel the same way about glory hole videos. Girls sucking a totally anonymous dick. Complete, unattached sex. Fun to get off to. But I could never actually do it. Far too impersonal. And risky."

I nodded in agreement. "I suppose, for me, I can't say I'd never try something like that, just for the experience. But yeah, I've learned I much prefer some kind of personal connection, even when it comes to casual sex. We don't have to be 'In Love,' but it's better with someone you at least like and care about."

"Like Trish?" Jenna asked.

"Well, I suppose. I mean I still don't know her well, and I don't feel drawn to her like I do with you. I suppose we have connected on some level, at least as friends. But I don't think I'd be interested in having a full blown relationship with her. Even if I'd met her before you. And any...sexual interest...I may have in her stems more from what we're sharing, what you've allowed me to share, and because you might enjoy sharing me with her, than any real desire to have sex with another woman besides you."

Jenna started laughing softly. "What? Did I say something funny?" I asked.

"No, it's just...that may be the strangest thing a guy has ever said to me. You basically just said you wanna have sex with my best friend because you'd think it could make me happy. And you might be right," Jenna laughed again.

"I'm not sure that's exactly what I said," I chuckled. "Again, right now this is all just fantasy talk. I have no expectations or demands to make anything like that happen. If we never did another sexual thing with Trish I'd be perfectly okay with it. You've already allowed me to explore so many of my fantasies, and I'll be forever grateful for that. Anything that does happen from here on out would be up to you. Well, the both of you, I suppose."

Jenna leaned up and kissed me. "I get you. And we'll see what happens." She yawned, then lay her head back down on my shoulder. "We can talk about it more another time. Getting kinda sleepy."

I kissed her forehead softly. "Get some sleep, darlin'. Love you."

"Love you too," she said sleepily, and I watched her soft eyes slowly close as she drifted off.

I gently freed myself from her embrace long enough to pull the covers up over her sleeping, naked form, then snuggled up beside her.

Not long after, sleep took me as well.

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AUTHORS AFTERWARDS

Having things happen in stories is a lot easier to write than writing WHY things happen.

I could just have written a chapter about a threesome with Tom, Jenna & Trish. Or a chapter about them going to a swingers club. Or both.

And I may still. But discussing fantasies (and their boundaries) is the first step to making them actually happen. And creating a scenario that makes these fantasies at least more plausible, if not entirely realistic, is more interesting to me than simply writing a new sexual situation every chapter. (Although I still managed to incorporate some sex and role-play into it anyway LOL.)

Hopefully, you found it interesting as well.

I put this in the Exhibitionist / Voyeur category despite nothing like that actually happening in the story because they discuss it heavily; what their fantasies are, and ways of exploring them.

Moving forward, these themes will continue to be a major focus of the story. Although not the ONLY themes.

Last note: I fully realize I made it a point for Jenna to stress the use of condoms in the last chapter, only to have her impulsively jump on him without one here.

But she had a valid excuse, and in the end, she still wound up pulling him out to finish on her, not in her. I don't think that was accidental. Jenna knows what she's doing.

To be continued.