The Jenna Arrangement: A Summary

The Jenna Arrangement: Past, Present & Future

Before we begin: This isn't a new chapter in the series, or a story at all, really, at least not in the sense most of you are looking for.

If you're looking for an erotic story, or you've never read my series The Jenna Arrangement, you can go back to browsing.

For those of you still here, I wanted to just talk a little about the series; where it came from, where it's gone, and where it might be headed.

I originally published The first chapter of The Jenna Arrangement to LE on 08/22/2021.

As of this writing, it is now 05/14/2023. The Jenna Arrangement (TJA) is currently at 26 chapters and a prequel.

Spoilers may apply if you have yet to read them all.

THE BEGINNING:

TJA was only the third story I ever wrote. It started from a simple enough fantasy premise: an older guy pays a young college girl to watch him masturbate.

I suppose it won't surprise any of you to learn the male lead "Tom" is loosely supposed to be a version of me.

Jenna, on the other hand, is completely fictional. She's not based on anyone I know personally.

The CFNM fantasy is one of my particular favorites, and isn't all that uncommon, really.

It's something I've always wanted to do, but have not, at least not the way it happens in the story.

Writing it as a fantasy, I needed a simple way to make it happen that at least felt plausible.

So I came up with the idea of Tom placing an ad. I didn't know who would respond initially, only that

I didn't want her to be overly sexual, or overly experienced. Somebody who probably would never have responded except she needed the money.

Jenna was born from that. Her character came naturally, easily. Beautiful, but not a Supermodel. Adventurous, but cautious. Shy, but playful.

The story was short, simple, and sweet.

I posted it as "Part 1" despite the fact that I had absolutely no idea how it would continue, only that I'd enjoyed these characters so much, I definitely wanted to write more about them.

And the overwhelmingly positive response I got from readers only reinforced that.

The problem I then faced was: How to continue?

I'd written myself into a certain corner with part 1. I'd established Tom as an average guy, not rich. So he wouldn't be able to afford to pay Jenna frequently for a repeat of their little "arrangement."

And while I was still getting to know Jenna, I knew her well enough to understand she wasn't the type that was just going to hop in bed with him immediately.

Plus, there was the problem of how to progress things between them besides him just repeatedly paying her to show up and watch him. Yet I was looking to write something that stuck, more or less, to the CFNM / voyeur / exhibitionist themes of part 1.

Part 2 came from me writing around those problems, finding a way to connect them and continue their relationship while doing away with the "pay to play" aspect.

I still have to laugh at my apology in the forward about it taking too long to get to the sexy stuff. At the time, I had no real grasp on how long a story should or shouldn't be, or what reader expectations might be.

I fully expected the comments section to be filled with complaints about "Nothing really happens til the end."

Instead, readers absolutely loved it. And apparently I'd struck a chord with the CFNM crowd, who, turns out, were in no rush at all to see Jenna and Tom just jump straight into a full fledged sexual relationship.

I know authors are supposed to write for themselves, not the readers. That said, reader feedback did influence how I continued.

Part 3 originally featured Jenna dropping to her knees to give Tom a blowjob, then jumping onto his lap to fuck him right there in the kitchen.

It was a very hot sex scene. Yet, it was completely wrong, completely out of character for Jenna. It felt rushed, forced, and I scrapped it in favor of having her simply up her teasing game.

And again, the readers agreed. While there was some debate between readers about whether things should progress physically between them or stay strictly CFNM, everyone agreed my "slow burn" approach was working.

I decided I needed to find a balance between the two ideas; I definitely wanted them to grow beyond just watching each other, but I also didn't want to rush it, nor turn it into JUST another story about two people eventually having sex.

I knew what Tom was getting out of this "arrangement," but I needed to figure out what Jenna was getting from it.

Part 4 let me get inside her head, to understand her motivation in all this.

And once I had that, I finally understood what the series needed to be.

While the story had started out as Tom's fantasy, Jenna herself quickly became the driving force.

She was the one who now dictated what would happen, how far they would go, and how fast.

She was the one that initiated their Snapchat role-play, the one that gave Tom her panties at the diner.

It was her idea to go on their first date at the lake, to take their relationship public.

And it was Jenna who initiated the teasing at the lake, and the fun they had back at her place afterwards.

And of course it was her idea to have Tom pose nude for her and Trish.

Despite the story being an obvious fantasy, I tried to keep it grounded in reality as best I could.

Which is why Jenna's roommate Michelle freaked out when she walked in on Tom masturbating for Jenna and Trish in part 9.

I caught some flack for that, but I think it allowed for a more realistic approach to the way I introduced her, and provided a way into Tom and Jenna's conversations about consent and boundaries as they explored their mutual kinks further.

Part 11, "Jenna Flips The Script," was probably my favorite chapter to write. I'd been wanting to write a scene where she was the one walking around naked for some time, but I had to build up to it in a way that felt natural for her character.

And as I mentioned in the Afterwards, the scene where Tom & Jenna play while Trish watches on the phone happened spontaneously, no planning on that at all.

Eventually of course, all that build up led to part 12, where Tom and Jenna make love for the first time.

I seriously did consider ending the series at that point. I never had a true End Game in mind for the series, (still don't,) and it could have been a nice, sweet place to leave them; happy and in love.

But I was still really enjoying this world I'd built, and the characters I'd created, especially Jenna.

So much so that I wrote the "Part 00: Prequel And Recap" story simply because I thought it would be great to hear the story told from Jenna's point of view.

It really gave me a fresh perspective on things. Although I will say it was an interesting challenge to go back and assign actual dates and days that fit for each previous chapter to make sure my time-line was correct.

Again, that could have been the finale. The final word on the story, from Jenna herself.

But then the idea for the Girls Night CFNM party came to me; Tom's ultimate fantasy come true. So of course I had to write it.

But I still had other adventures in mind for them. I began to see it as a serialized story; each chapter a new adventure; a way to build the world, the characters and the story but not really heading to some Ultimate Conclusion.

Still, I did have a few plot points to address: Jenna was a college student, and where was she going to go for the summer?

I'd given her some backstory with her mother and this was as good a time as any to flesh that out.

My original intention on sending her home was to simply write a few more virtual encounters between them; masturbating together on Snapchat or whatever.

But I'd already done that in part 5 and I didn't really want to repeat myself.

I'd also set up the possibility of Tom and Trish having sex with Jenna's permission while she was away, but, as I mentioned in an Afterwards, I quickly dismissed that idea, as I simply couldn't see it happening without Jenna present and sharing in it.

And so I sent Jenna home, only to have her run into her mom's creepy ass boyfriend.

Several readers were less than happy with that twist. And some were apparently confused by the notion that Jenna was upset that Dick was stealing her panties.

I'm not sure how the idea that he never asked for consent and invaded her personal space and privacy was "confusing." So I guess I have to spell it out here:

If you think it's okay to sneak into a young woman's bedroom and smell her worn panties without her permission, you're wrong. Sorry, not sorry. You just are.

The whole incident, and her mother's reaction, went far darker than I'd originally expected.

But in the end, it reunited Jenna with Tom and allowed me to explore the possibilities of them living together. It also set things up to allow Jenna to delve deeper into her own exhibitionist tendencies with her Only Fans account.

And of course to eventually get Trish in bed with, not just Tom, but Jenna as well.

That also necessitated the change of storytelling perspective from 1st Person to 3rd Person. So that I could not only get into Tom's head, but Jenna and Trish as well.

From there, it's been a series of short, fun little adventures, all exploring themes of voyeurism and exhibitionism.

THE FUTURE

I've obviously slowed down on writing new chapters for TJA over the past few months. There are several reasons; writing other stories mainly.

But also because I want to keep TJA fresh, and not simply rehash past stories or sexual exploits.

And so coming up with new, unique things for them to explore together will take more time and imagination.

Jenna is not a swinger. She's made that very clear to me. Other than her sharing herself with both Tom and Trish, she's not going to be moving on to orgies or sex with random partners.

I've been hinting for a long time about the roommate Michelle becoming more involved, but I honestly don't see her joining our happy trio fully. Although I do have a fun idea for her that would take things back to the original premise of the series in a way.

I have thought about just how long the series can continue. And of course I worry about dragging it out so long it becomes an empty shell of its former self.

I suppose at some point I'll have to conclude it. Although I'm honestly not sure how.

I don't want to break them up. But I'm not sure how I feel about a "they get married and live happily ever after" ending either.

The cold, hard reality of the story would be that Jenna graduates college and focuses on her career and her life, and that she and Tom would eventually drift apart.

The happier ending of course is "love finds a way" and they somehow make it work. And this is a fantasy series, so why not a Happy Ending?

If I could go back and change anything, I would have made Tom younger. I think it would make them staying together more believable. Not to say that there aren't couples with vast age differences that can and have made it work.

My other option is to simply leave it open ended. To write their adventures as they come to me, and not worry about summing it all up to some Grand Conclusion.

It could be like a comic book in that sense, or a soap opera series.

I'd be curious to hear from you readers your thoughts on their future; where you see them headed, or what the conclusion might be, if any.

No, I'm not asking you to write it FOR me. And don't be offended if I don't agree with your thoughts at all.

You might want to see Jenna in a gangbang, fucking all kinds of random guys or women, or both at the same time. And while you're free to imagine that, I can't stop you, I can say that's not the goal and never has been for this series.

I have, however, hinted about the possibility of visiting a swingers club. Tom and Jenna discussed it awhile back as a fantasy.

I will tell you that if / when that happens, it wouldn't be to hook up with random partners, but to explore their mutual fetish of watching and being watched.

That might be the perfect final story; Jenna embracing her inner exhibitionist fully and having sex with Tom, and perhaps Trish, in front of an audience.

In closing, I really would just like to thank you, the loyal reader.

I've gotten so much incredible feedback from readers, in public comments and private messages, telling me how much they love Jenna and look forward to her new adventures.

And I can't express enough how much that means to me; that Jenna is as alive and real for you as she is for me. So thank you.

Especially if you're still reading this. Because it means you still care about her as much as I do.

I wish I could promise a new chapter every week, or even every month.

What I will promise is this: If I decide to simply end it, I'll do my best to let you know.