The Jenna Arrangement Pt 00 Prequel And Recap

Author's Forward:

If you haven't yet read the first twelve chapters of The Jenna Arrangement, I highly recommend you do so first before reading this installment. They're all pretty short, if you're new to the series, just FYI.

This "Special Edition" chapter features some prequel events as well as a recap of the story so far, but told from Jenna's point of view. We'll talk more on this afterwards.

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE OR OLDER.

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Friday 9/12/20

So my first official week as a college student is under my belt. Not too crazy, mostly just orientations so far. My art teacher, Ms. Jenkins, seems pretty nice. I'm hoping to learn a lot from her.

Met my roommates this week of course. It's kinda crazy, going from being an only child living at home with mom to living with three strangers all around my own age.

I don't think it will be too terrible of an adjustment; they all seem very nice, and, so far at least, aren't complete slobs. So that's a good start.

Michelle is the oldest, just turned 21. Leana is 20, and Shiane is 19, like me.

Hopefully we all get along.

They've already invited me to a party tonight. They wanna go "meet some man meat," as Michelle so crudely put it.

I passed. I'm still feeling the sting of Jim dumping me. I mean I suppose it was unrealistic to expect we'd stay together, given we're both attending different schools, but it was the way he did it. He basically admitted he just wanted to play the field and bang other women and not be tied down in a long distance relationship.

Whatever. Good luck to any girl stupid enough to hook up with him. Hope she has fresh batteries in her vibrator, because she'll need it after he's done.

Speaking of vibrators, I'm hoping mine isn't dead, now that I think about it. I have the place to myself while my roomies are out. Why the hell not, I guess.

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Tuesday 9/29/20

Start my first shift at the diner tonight. Not a glorious job, and it's gonna be tricky working evenings after classes all day. But they're pretty flexible with the schedule. Money won't be great, but it'll be better than nothing I suppose, especially since getting mom to contribute anything is getting ridiculous. I hate having to beg for my own money.

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Wednesday 10/07/21

Made a new friend today. Well, we've sorta known each other since school started; she's in my art class. But we only really just started talking today. She complimented my drawing and we started talking about art and influences and we wound up having a lot in common. Wound up having lunch with her.

Trish is a little brash, but not in a mean way. She's also pretty talented. We're going to help each other out on projects and stuff; it'll be nice to have a partner. Her dorm is just around the corner, so hopefully we can hang out often. Not that I don't like my roommates, but they're still more acquaintances than friends, ya know? Michelle is the only one who seems to make any effort to be friendly. I hardly ever even see Leanna or Shiane.

Trish wants to maybe hang out this weekend. Not sure what we'll do but I'm looking forward to it anyway.

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Friday 10/30/31

So I'm alone again tonight. All the girls went to a Halloween party. I was tempted to go, actually. Even Trish went.

But instead I decided to just stay home. Michelle left me some wine, so there's that. I've already had two glasses LOL.

Guess it's time to fire up Old Faithful and see if there's any good porn to watch.

***

I can't believe what I just did.

So I couldn't find any interesting porn to watch, and wound up going on Omegle.

Part of it was sheer boredom; I thought maybe I'd actually find someone interesting to talk to.

It was nothing but a dickfest, of course. But I found myself actually WATCHING guys jerking off! I just thought it was funny at first; when they realized I was an actual live female they'd immediately start begging me to strip for them. I may be drunk, but I'm not THAT drunk! I'd get them all excited, thinking I was gonna watch and flash them, then click off their cams.

Then there was this one guy, an older man. He didn't have his dick out right away, but asked me very nicely if he could show it to me, if I could just stay and watch him.

So I agreed. I wouldn't let him see my face except for my mouth, but he never asked me to show him anything. He just took his already hard dick out and started stroking.

I gotta admit, it was kinda hot. He wasn't all that great looking, and his dick wasn't very big. But he was so nice and respectful, kept telling me how beautiful I was, and kept thanking me for watching him.

I wound up showing him a little cleavage, and when he was about to cum, I leaned in, opened up my mouth and stuck out my tongue. He shot right away at that, spunk everywhere. I even licked my lips like I was tasting it.

He thanked me again and I blew him a kiss, and he was gone.

I wound up watching four other guys, just the nice ones, before I finally clicked off and grabbed my vibrator.

I came several times, thinking about how I helped those guys get off without even having to touch them. Something very empowering about that.

Kinky? Maybe. Weird? Definitely. But it may be my new favorite way to get my kicks, LOL.

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Saturday 10/31/21

So my roomies decided to continue the Halloween festivities here tonight with another party. Oh joy. I used to LOVE Halloween. I dunno what happened.

I hung out long enough to be sociable, and okay, I've had a few drinks.

But now I'm alone in my room while both Michelle and Shiane are getting pounded by their new boyfriends. Jesus, they're loud.

I suppose it could be hot if I found either of those guys the least bit attractive. But I'm actually thinking more about Michelle. I'm not a lesbian, or even bi-sexual, but if I were ever going to experiment (and isn't your college years the time you're supposed to experiment?) with a woman it'd be her. Or Trish. Probably more so with Trish, I'm at least closer with her.

But no, what am I thinking? Guess it's the wine and sounds of sex echoing around the place.

Maybe I'll go on Omegle for a while. May as well, everyone else is getting off, why not me?

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Friday 11/13/21

Trish is spending the night; everyone else is out with their boyfriends, so it was just us.

We got into the wine, and smoked some weed Trish brought. She suggested watching some porn, which was fun for a bit. Then I suggested Omegle and wound up confessing what I liked to do to guys there.

She seemed to like the idea, and soon enough we were cock teasing multiple guys in a row.

We got a little carried away; wound up making out and feeling each other up a bit. But it was all in fun. And we kept our clothes on LOL.

It was a little weird, kissing a girl. But like Katy Perry sang, I liked it!

Afterwards, we wound up doing something unexpected. Both of us were pretty horny, and pretty high. Trish pulled her little Pocket Rocket out of her purse, telling me how she always had the best orgasms when she was high and hinting how she wanted to masturbate.

I wound up introducing her to Old Faithful, and next thing you know, we're masturbating side by side on my bed.

It was a little awkward at first, but the more I got into it, the hotter it was. Maybe I have an inner lesbian just waiting to break free. Or maybe I was just REALLY stoned. We didn't touch each other or anything, it was more of just a "I'll do me, you do you" thing.

We both came pretty quick, then threw our clothes back on just in time for my roomies to come home.

Trish is currently passed out next to me; Michelle is currently banging her boyfriend again. I'm not gonna get much sleep tonight I think.

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Monday 01/04/21

God I'm glad to be back at the dorm! Spending the holidays with mom wound up being torture.

She's got another new boyfriend, and already I hate him. Creep couldn't keep his eyes off of me. Mom was her usual, bitchy self, of course.

I gave her a drawing I did of her and dad from one of their wedding photos. She gave me a Visa gift card for 50 bucks. Merry fucking Christmas.

Anyway, looking forward to seeing Trish again, I've missed her. Maybe she'll come over this week and watch guys on Omegle with me again. I gotta admit that was fun. And hot.

Speaking of; I probably shouldn't stay up too late, but I'm thinking I may need a little personal time before bed. Let's see if I can make a few guys cum.

I wonder if someone can become addicted to cock watching?

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Sunday 2/21/21

I saw the strangest ad on the campus personals page today. Some guy looking for an "erotic fantasy" with a college girl, willing to pay two hundred dollars cash, yet claiming he doesn't want sex.

As much as I could use the cash, (mom's still being her usual tight ass self about giving me my own trust fund money) I'm sure it's gotta be either a scam or some pervert who'll want me to fuck him.

Still, I'm tempted to answer it. My shifts at the diner have been sporadic at best, and even on a good night I don't make much, and I really need to get those books for art class.

The ad said to email for more details. I guess I can create a burner email account to use just to see, if for no other reason than to satisfy my...curiosity.

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Monday 2/22/21

So I answered that ad and got a reply back almost immediately. He claims he just wants to jerk off in front of me. Says I don't have to touch him or get naked or do anything but watch.

I find that all very hard to believe for the money he's offering. Still, if he's legit, it would be the easiest pay I've ever earned. And it's not like I haven't watched guys masturbate for me before. Of course, there's a big difference between teasing guys online on Omegle and actually meeting a total stranger in person. The guy could be any kind of awful sex predator.

He looks pretty normal in the picture he sent me, though. Pretty handsome too, for an older guy. He also kinda reminds me of my dad, which is sorta weird, but not entirely off-putting.

I must be crazy for actually considering this. I need some time to think it over.

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Thursday/25/21

I can't believe it, but I actually agreed to meet this guy tomorrow at the coffee house.

I still haven't fully committed to going through with it, but he's at least promised to buy me a meal while we discuss the details. I guess it can't hurt to meet him in a public place, right? And if he turns out to be a total creep, I can just bail.

He really doesn't LOOK like a creep, though. He sent me a second picture, and he's really a decent looking guy. Very normal looking. I know, I know, that doesn't mean anything of course. I'm sure the women Ted Bundy killed thought he looked pretty normal when they first met him.

What the fuck am I doing? Do I need the money this bad? Well, yes. But I'd be lying if I said I wasn't at least a little...curious. I've never seen a guy masturbate in person before, just online and in porn. I can't help but wonder if I'll get as turned on from it as I do watching guys on Omegle.

I still often wonder why that gets me so hot. Part of it is the ego boost I suppose, knowing these guys think I'm sexy enough to want to get off to. And the control; I can get them to cum for me without ever even getting naked, let alone having to touch them.

I don't know. Maybe it's just been too long since I've done anything adventurous. Because unless this guy turns out to be a total freak show, I'm seriously considering going through with it.

Guess I'll find out tomorrow.

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Friday 2/26/21

I'm an absolute basket case right now, but I want to try and write this all down while it's still fresh.

I went through with it!

I met Tom (guess after what happened I should at least use his name haha) at the coffee house as planned. I'm not sure why exactly, but after talking for a while I just started to feel comfortable with him. So strange how he reminds me of my dad. But he's also really attractive. That's not creepy, is it?

He seemed very, well, NORMAL. He did seem somewhat sad, although he tried to hide it.

I get the feeling he's had a rough time with his past relationships, and again it made me think of how dad was after the divorce. And I think that's what made me agree to it.

I brought him home. Impulsive and dangerous, I know, but I felt safer here than going to his place or some hotel room. And I had my pepper spray, just in case.

It was a little awkward, taking his money. I still felt like a prostitute, even though I wasn't going to actually fuck him.

It wasn't until he started to undress that it became real for me. Up until that moment, it was just a bit of fantasy.

And then he was naked. And I'm just sitting there, staring at an absolutely gorgeous cock.

I thought it would be like on Omegle; I've seen all shapes and sizes there and frankly, a dick is a dick, right?

But seeing Tom's in person, literally growing for me right before my eyes...it was both intimidating and thrilling.

I sat there across from him and watched him jerk off while he looked at me with his beautiful hazel eyes and tried to pretend I was so cool and casual; meanwhile my heart was pounding a mile a minute. And not from fear.

I even gave him my panties! Well, sold them to him actually.

I almost didn't, despite the deal we'd made for an extra hundred. Not because I was losing my nerve, but because I wasn't sure I wanted him to be able to tell how fucking AROUSED I was getting.

That's the scariest part: I truly didn't expect to get that turned on.

It wasn't just his cock, although, truth be told, he has a really nice one.

It was the way he looked at me while he touched himself. He openly admitted to finding me attractive, but he wasn't looking at me like I was just a piece of meat or something. He looked at me like he cared about how I was feeling and what I was thinking. And he went out of his way to make me feel comfortable and relaxed.

He was kind, and respectful, and never attempted anything beyond what we'd agreed upon. It reminded me of that first guy I let jerk off for me on Omegle. Except Tom was live and in person. And had a much nicer dick!

God, I must have sounded silly to him when I started comparing the size of his dick to others like I've had some vast experience with them before and not just a few sticky, unsatisfying fumblings with guys who wound up only using me to get off. I don't know why I said all that shit; I guess maybe I wanted him to think I was more experienced than I am.

My panties were soaked by the time I handed them to him. Which I kinda freaked out about a little; I was petrified he might think I smelled bad. Especially being this close to my period!

He seemed to really enjoy them though, even put them over his face, which was pretty funny.

I almost came myself, watching him cum. I had to struggle not to squirm in my chair.

When he left, I ran back to my room and masturbated furiously, and I couldn't...still can't...get the image of his cum erupting all over himself as his intense eyes looked at me out of my mind.

I wanted to fuck him in that moment. I wanted to go over and lick his hot cum off his cock and stomach. I wanted to pull my skirt up and push his face into my dripping pussy.

And that terrifies me.

I told him we could do it again before he left, I even hinted I might be willing to do it for free, I was that turned on.

What the hell am I thinking???

Am I really considering doing that again? Maybe doing more than just watch?

Why do I want to see this guy masturbate to me again so fucking badly???

I just let a complete stranger get his rocks off in front of me! I let him PAY me to do it! And I wanted...I WANT...MORE.

I don't know what to do.

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Saturday 2/27/21

I've deleted his emails, blocked him, and locked myself out of my burner account. That way I can't be tempted again. It was too dangerous, too crazy. I was foolish to do it.

It's not him I don't trust. It's me. I don't trust myself to behave if we get together again.

Better to just forget about it.

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Sunday 4/02/21

I dreamt about Tom last night, that guy I had the little "arrangement" with.

I dreamt about him masturbating for me, his thick, beautiful cock throbbing while his gaze lingered on me. Only this time, I was naked too, and fingering myself furiously. I woke up just as he came all over my face.

My panties were soaked. I spent the next hour with my vibrator and some CFNM videos, although none of them were doing it for me and I kept visualizing the dream instead.

I thought about going on Omegle and finding a random guy to jerk off for me, but after having Tom do it in person, it's just not the same now.

I wish I hadn't deleted his contact info. And I feel bad I didn't even tell him why.

But what's done is done I guess.

I wish I had at least taken a picture of his dick, though. Or asked him to email me one.

I wish we could do it one more time. Although I couldn't take his money again, no matter how badly I might need it. It made me feel too much like a hooker. Which I'm not against, no judgment, ya know? But it's not for me.

Although I have been seriously thinking about starting an Only Fans page. Michelle has one, and makes some great money at it. I don't know that I'm brave enough for that though. And yet I was brave (stupid?) enough to bring a stranger home to get naked for me. Go figure.

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Wednesday 4/12/21

I've been doing some research on the whole CFNM thing. Apparently it's a much more common fetish than I thought. For women as well as the men.

I know I enjoy the feeling of control I get on Omegle; a feeling I never had with the guys I was involved with.

I can decide who I wanna watch, how long, and how much I want to tease them. And I can stop things at any time if I feel uncomfortable.

I wish I'd had the opportunity to explore that more with Tom. While he was pretty much in control during our...arrangement...I never got the feeling of being out of control. He allowed me the freedom to interact only as much as I was comfortable with. I kinda wonder now what I'd have done if I was a little bolder.

I wonder if he'd let me have complete control. Let me tease him, guide him, direct him, like those guys on Omegle.

I don't want him to just jerk off for me again. I want him to know I like it.

Jesus, I never realized I was this kinky. I'm kinda liking it. Too bad I'll probably never see him again, dammit.

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Sunday 5/9/21

Okay, a lot to unpack here!

I met Tom again! Totally out of the blue, he showed up at the diner Friday night!

I literally dropped my order pad when I realized it was him. I thought maybe he'd tracked me down somehow, but from his reaction it seemed he had no idea I'd be there.

He was very cool towards me, playing it casual. Which in a way I was grateful for. I'm glad he didn't try to make a scene while I was working.

Long story short, he wound up giving me a ride home during a freak rain storm. We both got totally soaked, and I wound up inviting him in to dry off and wait out the storm.

We were both so filthy after falling in the mud we had to strip off our clothes right at the door. He was such a gentleman, respectfully looking away while I undressed. Although a little part of me wanted him to peek. I know I did when he was undressing.