The Jenna Arrangement Pt. 04

Authors Forward: There's a lot of exposition in this chapter. And a lot of dialog. I tried to make it flow as naturally as I could. I'm still new at this, so forgive me where I fall short.

While there are references to sexual situations, there's no actual sex in this chapter. But I needed to get to some backstory before being able to move these characters forward. If you've been following this story so far, I appreciate your support and patience.

ALL CHARACTERS ARE 18 YEARS OF AGE OR OLDER.

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Jenna broke the silence. "So I guess we should probably talk now."

I hesitated before replying. "Ok, but before this gets too heavy or anything, let me just say that wherever this ends up, it's been a lot of fun and I have no regrets. And I'm not looking for some kind of commitment here or anything."

"I have no regrets either," Jenna smiled, "and I appreciate that. I think it'll help you understand...this...if you understand me a little better."

I sat back and nodded, allowing Jenna to gather her thoughts.

"I was a bit of a late bloomer," she began, "I was always the freckled little mousy girl none of the boys ever paid attention to. I didn't start dating until I was a junior in high school. The guy I lost my virginity to dumped me the next day, told me I was a 'lousy lay,' can you imagine that? My first time, and...well, I'm sure you can understand what that did to my self esteem. I dated a few other guys, briefly, never going very far. The second guy I ever slept with was...better. He was a nice guy, I thought we were in love. But he broke up with me too, told me he was too young to be tied down to one woman, and with him going off to a completely different college, he wanted to see other girls.

I haven't dated anyone since then. When I came here, I decided I wanted to focus on my studies, and my art, and not get caught up in the party scene or chasing boys. Don't get me wrong; I'm no prude. I actually have a very high sex drive. I've just been satisfying it in...other ways."

Jenna paused, flushing a bit as if embarrassed. I tried to lighten the mood. "Hey, sometimes we all have to make due with what we have in...hand."

Jenna rolled her eyes. "Not one of your better ones," she groaned, but still couldn't suppress her smile.

"I watched a lot of porn," Jenna continued, "although I found most of it very unrealistic, at least from my limited experience. But I found some amateur ones I liked, and they...taught me a lot.

I also discovered something called CFNM, you've probably heard of it, right?"

"Yeah," I replied, "I'm...familiar with it."

She laughed. "I suppose you are. Then I don't have to go into too much detail there I guess. Most of them are all pretty much the same, although I preferred the ones where the women weren't being mean or abusing the guy, that never appealed to me. I much preferred the ones where the woman teased the guy, getting him all hot and bothered, but kept most of her clothes on while he, you know..." her hand made the universal gesture for jerking off.

Now she was making me laugh. "Yeah I've seen all the basic variations. Most of them are pretty fake, or start out good but wind up with them just turning into a standard porn."

She smiled knowingly. "Yeah, I almost always turned those off once they started fucking. Depending on my mood of course."

Despite having just masturbated not long ago, I still felt a bit flushed and aroused, sitting around with this lovely young woman, casually discussing our mutual tastes in porn. But I also remembered she was trying to explain herself as well, so I tried to focus more on the meaning behind her stories.

Jenna continued, "I think what appealed to me most about those kinds of videos, at least the good ones, was they were kind of empowering to the women. They were the object of his pleasure, sure, but they usually had some form of control over it, and didn't have to do anything unless they wanted to. It was very different from the situations I had dealt with, the guys I'd been with, you know, pressuring me." Jenna paused here with a slight frown.

Understanding, but not really knowing what to say, I just nodded sympathetically. She smiled again at that, then continued.

"I also discovered Omegle. I'm sure you're familiar with that as well? The one where you're supposed to 'chat with strangers,' but it's really just filled with random guys trying to flash their dicks."

I hesitated before answering, "Yeah, I'm...familiar, And I'll admit, I was one of those random guys. But only a few times. It really never paid off, and I was also starting to feel creepy about it. Like a dirty old man."

She nodded. "I guess I sorta understand the appeal for men, if not condone the methods. I suppose you never came across me on cam though, because I...I probably would have stayed and watched."

My eyes went wide with surprise. She blushed, then explained, "I found a certain...appeal...in it. The idea that I could help pleasure a man without really having to DO anything. I NEVER showed my face, or got naked, or anything like that at all. But I found that if I showed enough of my body, usually my boobs under a shirt like the one I was wearing earlier, and no bra, the guys would of course immediately whip their dicks out if not already jerking them. They always seemed surprised when I didn't click off their cam immediately.

How long I watched them depended on how nice they were. They almost always asked me to flash them, or show my face, or masturbate with them, and when I always refused, some would get mad, say rude things. I dumped their cam right away.

But most were nice, said they understood, and just asked if they could cum for me. Those guys I stayed with, and I encouraged them. Sometimes I'd wiggle my boobs or lean in to show them some cleavage, or spin around so they could see my butt if they asked, but always clothed. And never my full face. They were always complimentary, telling me how beautiful and sexy I was, and after they came they'd always thank me. It...really helped my self esteem.

I'd spend an hour, maybe two some nights, just scrolling random cams, helping guys get off. They'd never last more than 5 minutes, most of them took a minute or less. I learned a LOT about penis shapes and sizes, a lot more realistic than the massive ones you'd always see in porn.

Looks didn't matter so much to me as their attitude, and while there were a lot of young, hot guys, there were plenty of older men too, all shapes and sizes. The young studs were always the cocky ones, and I'd leave a lot of them disappointed, pretending to go along with them for a bit before suddenly cutting them off.

The older guys were almost always the more respectful ones. They just seemed appreciative that I was watching and happy with whatever I would give them." She paused for a moment to sip her water.

"I can't speak for all men," I said, "but for most guys, when we hit middle age, we start to understand we're never gonna be able to go back and be with young women like we used to; we kinda become invisible to the younger generation. And it can be rather...depressing. So yeah we're usually very appreciative if any pretty young thing even gives us a look," I finished with a half hearted laugh.

Jenna grinned. "You'd probably be very surprised at how many women my age find older men attractive. They're certainly more mature."

"I guess," I shrugged. "I've never been much of a Ladies Man anyway, now or when I was younger. If women of any age are coming on to me, I am apparently missing the clues."

"I've noticed that," she said with a wink. My eyebrows raised in surprise, and she laughed. "Yeah you're clueless alright," she giggled.

Before I could say more, she continued her story, "So anyway, I suppose you're thinking all of that explains why I answered your ad. But that's not exactly it. Your ad wasn't very specific at all, and the only reason I answered it was because I needed the cash. I figured I'd respond, you'd send back some request for sex, I'd ignore it, and that would be that.

But then your reply detailed what you wanted, and yeah, it did remind me of the guys from the webcams. I figured, how terrible could it be? I've done it countless times on cam, this would just be in person. Of course, I was terrified, because unlike doing it online, I'd actually have to meet you face to face, be somewhere alone with you, and obviously I knew how risky that was. You could have been a rapist, or serial killer, or sex trafficker for all I knew."

"Then I opened the picture you attached..." Jenna stopped here, reluctant to go on, then gathered her courage. "...and you reminded me of my dad."

My jaw dropped, stunned. Jenna saw my look and quickly continued, "Now don't get any weird ideas. I was never, EVER sexually attracted to my dad. And he never molested me or anything like that.

I loved my dad, he was the world to me. But I could tell as I got older that things weren't good between him and my mom. She always seemed to be upset at him about something, always putting him down, always bitching about how he wasn't a good provider and what a struggle it was for us. Keep in mind, we weren't poor. We had a nice house, I never seemed to want for anything. I had nice if not expensive clothes. I had video games and my own TV. My mother always had a new car every two years, while my dad drove the same old truck to work year after year. We went on nice vacations, and my mother was constantly going to the salon to get her hair or nails or whatever done. But she never seemed happy with any of it, and would always complain to my dad about how all her friends were much better off, going on expensive cruises or European vacations, or how much bigger their houses were or how much better their furniture was.

It was wearing him down, I could tell. But he always had a smile and a kind word for me, no matter how exhausted he was when he got home from work. And when he discovered I had some art talent, he was the one that encouraged it and kept me in any art supplies I needed. My mother barely endured it, calling it a 'waste of time.'" Jenna paused, on the verge of tears.

"That must have been...very hard on you," I said softly.

Jenna composed herself, then continued, "Yeah, but for the most part, I was happy growing up. At least until my parents sat me down shortly after I turned 12 to tell me they were getting a divorce.

I never knew the exact reason why. I don't think my father cheated on her, but if he did, I suppose I couldn't blame him. She was...still is...a real bitch.

Mom got custody, but I saw my dad every weekend. He was struggling with finding a new place, paying alimony and child support, and I knew he was picking up extra hours at work, pulling double shifts sometimes, to make ends meet.

But he never missed a weekend, and he always had something special planned, even if it was a simple day at the park or zoo, where I could bring my sketchbook along and practice drawing the scenery, or animals, or whatever. One day we went to the lake and we just sat there for hours while I drew. I still have those sketches somewhere," she sighed wistfully.

She sat quiet for a moment, her face sad, her eyes watery. "Two years after the divorce, we found out he had colon cancer. Six months later, he was gone."

Unable to hold them back any longer, Jenna burst into tears. I went over to her, put my arm around her shoulder, and hugged her as best I could. "I'm so sorry for your loss," was all I could manage. I held her quietly while she cried. Not knowing what else to say, I went to go find her a box of tissues, which she accepted gratefully.

After I'd settled back on the couch and she'd composed herself again, she continued her story.

"He had a life insurance policy, and it was a good one, fortunately. Enough to help mom pay off some bills. A little nest egg for me, not a huge amount but enough to help me get started with a life after college. I was supposed to get it when I turned 18, but my mom somehow arranged things so she has control of it until I turn 21. She can't actually spend it, thank god, or it would probably be gone already. She can dole out small amounts to me if I request it, but fighting with her over it tooth and nail isn't even worth the effort anymore. My scholarship pays for my classes, the rest I pay for mostly myself. When I'm 21 I'll get my money and be done with her." There was a hint of anger in her voice as she finished.

The silence sat heavily for a few moments. "Well," I said, "at least you seem to know what you want from your future, and will have a good foundation to start it. Your dad would be proud of you, I think."

She looked up at me with a sad smile. "I hope so," she sighed. "Sorry if I'm hitting you with all of this, but I wanted you to understand where I'm coming from."

"It's ok, I'm glad you're telling me this. I feel like I understand you better," I replied kindly.

She sat up straighter and smiled again, seeming to find her cheer. "Thanks. I guess I just need to explain a few last things though."

I nodded, urging her to continue. She gathered herself and began again.

"I didn't know for sure I'd say yes to your proposal until after we'd met and chatted a bit at the coffee shop. Like I said, your pictures reminded me of my dad, but that didn't really mean anything. You don't even really LOOK like him, just, I dunno...certain features I guess. Maybe I'll show you a picture of him later, you can decide. It's not really important anyway. What was important was, after talking with you, you reminded me of dad in other ways.

You were polite, kind, caring, a good listener. But you tensed up any time we talked about your past. When you mentioned your divorce, I saw the same sadness I used to see in dad's eyes when he thought I wasn't looking. I could tell you'd been through...something. Something you didn't really wanna talk about. Something that had hurt you, but you'd come through it."

She looked at my face with a sad smile. "When I asked about your past relationships, you had the same look you have now, a look that says you really don't want to talk about it. And it's ok, we don't have to, not now. Maybe when you're ready one day. I just wanted you to understand that that's what ultimately made me say yes; because I felt...not sympathetic, exactly, maybe empathetic? I dunno, I just know you reminded me of my dad after the divorce and I felt like I at least understood your strange request a little better. Does that make any sense?"

"I suppose it does," I said.

We sat quietly for a while, allowing me time to absorb everything she'd told me. A question popped into my head, one I found myself hesitant to ask. "At the end, earlier, when you let me...you know..." I couldn't bring myself to finish the thought.

"Cum on my face?" Jenna finished for me. "Oh, that was just...spontaneous. I'd never had a guy do that before, saw it in porn a lot, looked like fun, so I figured why not?" Her face was a mix of flushed embarrassment and happy pride that somehow made her even more adorable, especially when my mind flashed back to that same face covered in my semen not too long ago.

"Did you enjoy it?" She asked with a grin. "Well, um, duh, yeah," I said. "Good," she replied, "I did too. I've heard a lot of women say that kind of thing is degrading, and I suppose it could be in certain situations. But I actually found it...empowering. If a little messy," she finished with a laugh. It was nice to see her mood lightening again after the more serious discussions earlier.

"I've never actually had the guts to ask a woman to do that before," I said, "and no one ever offered to let me...until today. So thank you for that."

"You're welcome," she said, "maybe we can do it again sometime."

"So..so there'll be a next time?" I asked, hopefully. "I mean, I guess I'm still not sure what this is between us now, and we don't have to figure that all out just yet. But I do know I'd like to...see you again. In whatever way you're comfortable with."

She stretched a bit in her chair. "I'd like to see you again too. I don't know what to call this exactly either, although I suppose we can at least call each other friends at this point, right?" I nodded in agreement.

"As for the rest of it," she continued, "I suppose we can figure that out as we go. But for now, I guess we can just call it..."

Jenna paused for a moment, then finished with an echo of the words I'd used on our first meeting, "...a mutually beneficial arrangement. "

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Afterwards:

I've gotten mixed feedback as to how this story should progress. Some want it to stay within the confines of CFNM, others want to see it go beyond that.

My goal is to find a good balance. Obviously this is a fantasy story, but I've approached it as realistically as possible. I don't think it would be "realistic" for them to be fucking by the next chapter, but I also don't think it would be "realistic" for them to go several more chapters never touching each other. At some point their...arrangement...will involve more than just watching each other from across the room.

Now that we've gotten inside Jenna's head a bit, I think things will start moving a little faster.

Feedback, as usual, is welcome.

To be continued...