The Jenna Arrangement Pt. 00 - Prequel and Recap

I still feel a little bad about giving him nothing but a silly looking pink Snuggie to cover up with while I washed his clothes.

Or at least attempted to wash them. The power went out before they'd finished.

I apologized to him about never responding to his attempts to contact me again and explained why. He took it pretty well and seemed to understand.

We'd both had our showers before we lost power, and although I had plenty of clean clothes of course, I wound up staying naked under my bathrobe. I told myself I was just being comfortable, but I knew he must be thinking about what I was, or wasn't, wearing under it.

Still, he never made a move on me, or even hinted at anything, despite me having teased him a few times.

I found myself wondering about what was under the Snuggie and if he was already hard beneath it and just hiding it well.

I decided I needed to find out. I asked him to pose naked for me so I could practice my sketching. The look on his face was priceless; a mix of shock and excitement.

He actually didn't get a full erection until about halfway through my drawing. Even in the dim candle light I could see his excitement. My pussy was getting so wet as I sketched his beautiful cock. I could barely contain myself, although I played it very casually.

By the time I finished the sketch, I couldn't take it anymore. I gave him permission to jerk off for me again, and wound up masturbating myself while I watched him!

I couldn't believe I was being so brazen. I hid myself in the shadows so he couldn't actually see me...or at least, I was pretty sure he couldn't see me. I kept wondering how much he could see, or if everything I was doing was left only to his imagination. I'm sure he could at least hear how wet I was. And my moaning.

It was such a fucking turn on! I came within minutes. So did he, of course.

I felt a wave of embarrassment after, though. I don't know why we feel guilty about masturbating; repressive society ingrains it in us I guess. Although it wasn't guilt about the act itself so much as doing it so wantonly like that in front of someone still essentially a stranger.

We quickly cleaned up, and I let him spend the night in the spare bedroom.

I was so wound up with a mix of emotions that I couldn't sleep. I was both ashamed and embarrassed by what I had done, and yet incredibly aroused and empowered by it. Arousal won out and I wound up masturbating again, thinking about him watching me, and fell asleep quickly afterwards.

I woke up before him the next morning. The power was back on and I was starting the laundry when he walked out of the bedroom, completely naked and with a massive morning erection.

There was something so erotic about it that I decided I didn't want him to cover up, and I told him he could stay naked as long as he wanted. I was dressed of course, although my outfit was a bit skimpy.

He wound up staying naked throughout breakfast, his cock fluctuating between fully hard and only semi erect. Even semi aroused, his cock looked so tempting. He was trying so hard to be cool and casual about it, but I could tell he desperately wanted some kind of release. His eyes were all over me as he helped me clean up after, and at one point his fully erect cock brushed up against my bare stomach. It was like an electric shock went through me, and my clit was throbbing. He wanted me so badly, and I was getting off on it.

He wound up masturbating for me again, but this time I actively teased and tortured him, getting him to confess his carnal desires while I deliberately teased him with my fully clothed body.

I was reveling in the feeling of control over him, and I was so fucking hot that I didn't even think twice when I decided to let him cum on my face.

I literally had an orgasm right there as his hot spunk splattered all over me. It was an absolute feeling of empowerment to have caused that much desire and pleasure without having laid even a finger on him. I even tasted his spunk, something I'd never done. I was so in the moment I didn't even hesitate. The taste was better than I expected, but it wasn't even about that really. I knew doing it would shock and please him. What I didn't know was how much I got off on it too. I liked being a little cum slut. Maybe I watch too much porn LOL.

I quickly went off and masturbated in the shower, cumming several times.

After his shower, we both got dressed and wound up having a long talk.

Well, I did most of the talking, telling him a lot about my past; my bad experiences with my former boyfriends, and about my dad and what he had to deal with after the divorce, and how he reminded me of my dad and that was part of why I felt drawn to him.

I still don't know exactly what this THING is we have. I'm not looking for a boyfriend, but if I were going to see anyone on a casual basis, it would be him. Despite the age difference, we have a lot in common, and I do find him very attractive; both physically and as a person. He's kind, sweet, funny, caring and most of all, respectful. He's agreed to take things slowly and just roll with things as they happen.

Before he left, we swapped contact info, and I even set him up with Snapchat. He was clueless about it, but figured it out pretty quick.

I miss him already. Just thinking about what's happened the past two days has gotten me so worked up. I don't know just how far I'm actually willing to go with him yet. All I know is that it's been too damn long since I've had any kind of sexual outlet besides porn, Omegle, and Old Faithful.

And he makes me feel good about myself while letting me explore my own little kinks at my own pace without judgment or demands.

I wonder if he's thinking about me right now. I wish he could see me, sitting here on my bed in my tiny little half shirt and boy shorts. I bet he'd get a hard-on again.

I think I'll send him a picture on Snapchat. See what happens.

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Tuesday 5/11/21

We made plans for this weekend to go see Jaws at the lake! I'm very excited, yet also nervous.

Not about going out with him in public. I'm beyond being worried about what other people think. It's just been a long time since I've gone on a date. If that's what this is. I can't actually think of a better word for it anyway. Should be a lot of fun. My dad loved that movie, but I was always too afraid to watch it with him. Hopefully it won't freak me out too much.

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Wednesday 5/12/21

Tommy stopped by the diner tonight for dinner. It was so sweet how he texted me first to make sure I was okay with it.

I was actually more than okay with it. I've been a bundle of sexual energy ever since our weekend together, and our Snapchat Sunday night (which was fucking hot, BTW) only made it worse.

I honestly don't know what came over me. All he did was show up and eat. I think it was when he slipped and called me "princess," and it got me thinking about the role-play fun we had on Snapchat. It made me feel...tingly.

I managed to sneak away to the bathroom for a few minutes. Not the ideal scenario to take care of my sudden need, granted. But at that point I didn't care. I just needed to cum, badly.

My panties were already soaked, and I started to think how much Tommy would enjoy smelling them. The thought of his nose buried in them made me even hotter.

That's when I decided to take a few naughty pictures for him. And then my hand was in my panties, rubbing myself like a woman possessed. I had to stifle my squeals when I came, not wanting the entire diner to hear me.

I was a gooey mess when I was done, and I made sure to catch every drop of it in my already soaked panties. Then I peeled them off and shoved them in my skirt pocket. I found a bag for them in the kitchen and slipped them to Tommy just before he left. I think it really confused him when I told him it was "dessert." I made him wait til he got home to open the bag.

Work got busy after that, so I didn't have time to check the pictures I'd told him to send me. But I could imagine them; his big, hard cock, all aroused and excited from smelling my sticky wet panties. I had to push those thoughts from my mind to get through the rest of my shift, since I didn't want to be serving customers in an aroused state. Especially since I was no longer wearing panties. I felt so slutty. And it felt amazing.

Tommy texted me, offering me a ride home. I get the feeling he really just wanted to see me again after my little surprise treat, and I almost took him up on it. But I wasn't sure what his expectations were and I didn't want to lead him on; I'm enjoying our fun, but not ready to go too far just yet. I decided the walk would help clear my head.

I was exhausted by the time I got home, but still, I couldn't wait to check out his pictures. And they didn't disappoint.

He sent me several, including pics of him smelling AND tasting them. But the one that truly got me going was the one of his cock posed over my panties like he was imagining fucking me in them.

I texted him to thank him for the pics, then gave myself a quick but satisfying orgasm.

Been a long day, but certainly ended on a high point. I'll sleep well tonight.

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Thursday 5/13/21

Trish discovered my little secret relationship by accident. We were talking about the upcoming nude art project for class, and going through my sketches when she spotted the one I did of Tommy. I'd forgotten it was in there.

She grilled me with all kinds of questions: Who was this guy? How did I meet him? And how did he wind up modeling naked for me?

I told her parts of the truth, but not everything, although I was tempted to. She really let me have it about bringing a stranger home, and was more than a little concerned about the age difference.

But she also seemed, well, almost jealous. She kept gushing about the sketch, especially about how hard I'd drawn his dick. Pretty sure she suspects that, at the very least, I didn't leave him with a case of blue balls. We used to joke and kid about all the guys we'd gotten to jack off for us on Omegle, but I also know she got off on it, too.

She wants to come with us to the lake on Saturday. Not sure if she's curious about Tom, or just wants to protect me, or both.

I'll have to call Tommy about it tonight. I hope he won't be upset about it.

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Saturday 5/15/21

What an amazing day! I feel like I'm floating right now, I'm so happy.

Our day together at the lake was perfect. Well, almost perfect. There was one asshole who started harassing me about being there with my "grandpa," and when I told him to piss off and tried to get away from him, he grabbed me.

I made him pay for that mistake. I pantsed the little prick. And I do mean LITTLE. The jerk was hung like a raisin, LOL.

It almost got me thrown out of the lake. Luckily some quick thinking by Tommy saved me there. My hero!

Speaking of Tommy: We had a few really intimate moments together at the lake. We wound up kissing, like REALLY kissing, while swimming.

Okay, yeah, we did more than just kiss, too. But can I help it if I turn him on so much he gets a boner even in cold water?

I still can't believe how turned on I got grinding up against his cock in the water. I don't think anyone noticed us, even when I came. But I almost wanted them to.

I felt bad leaving him with such a raging hard-on, and later I tried to give him a handjob during the movie, but he stopped me. I was kinda bummed about it, it would have been fun. But I guess I understand. He was worried about people noticing. Plus I suppose it would have been...messy.

It was the second time I blue balled him though. Although I definitely made it up to him when we got home!

He came out of the shower to find me wearing only a little pink crop top and panties. He must have really liked it, judging by how fast his beautiful cock got hard for me!

I wasn't ready to go all the way just yet, (although I must admit, it's been tempting) but I gave him a really slow, sensual handjob. He's very modest about his size, but, while he's no porn star, he really does have a nice sized cock. I couldn't even fit it in both hands!

I was feeling particularly bold, and decided to finish him off by grinding my pussy over his cock.

His hands felt so fucking good on my body! Especially when he sucked my nipples! I came twice myself. I almost let him finger me; I thought he might try, but he respected my boundaries and instead just put his hand over mine as I rubbed my clit.

Oh, and he almost fingered my ass, well, more like just brushed over it with his fingers. It sent a shock through my body. I've never done any anal stuff, so I didn't realize how sensitive I was there. We may have to explore that area more some time.

We had a really nice chat afterwards, and I found out a little more about what makes him tick. And his past. He's had a rough go of it with past relationships. Which I can certainly relate to. Maybe that's why we seem to gel so well.

He got a bit emotional at the end, even cried a little. It was so sweet.

I was so tempted to ask him to spend the night and just cuddle with him til the sun came up. I probably should have. Next time, maybe.

Hang on, phone call.

***

That was Trish. I'd promised her earlier I'd coach her for the art project, and she actually just asked if I could convince Tommy to pose nude for us tomorrow!

I honestly can't tell if she's really that worried about her art skills or is just looking for an excuse to see him naked in person.

The strange thing is: I wouldn't mind. Is that weird? Most girls would probably freak out at the idea of their BFF seeing their boyfriend naked. (IS Tommy my boyfriend now? I guess he must be at this point. It's weird to consider, but I can't think of a better word for it.)

But not only am I not upset by the idea...it actually kinda fucking turns me on!

I'll have to call Tommy in the morning, see if I can talk him into it. I'm sure I can. After all, isn't that his fetish? He enjoyed it with me, I'm sure he'd want to do it with Trish, too. Although he may be afraid to admit that to me. Probably think I'd get jealous.

I'm curious about that myself. Right now, thinking about it, I think it could be fun and sexy. But what if I wind up getting upset by it? If he gets an erection around Trish, will I get jealous? Wondering if he wants to fuck her instead of me?

I'll sleep on it and figure it out tomorrow.

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Sunday 5/16/21

Well, I really went and fucked up this time!

Things started out great; I'd convinced Tommy to come over and model nude for Trish and I. We were all having fun with it, too. Trish had been playing it cool, but I think she was enjoying seeing Tommy naked, especially after I teased him into getting a hard-on, as much as I was enjoying showing him off.

And I wound up not feeling jealous at all.

Instead, I was happy and excited for Tommy, knowing he was getting a chance to enjoy being exposed to another woman like that, and I was also happy that Trish really seemed to be into it too. And I found myself really fucking turned on by letting my best friend see my man's sexy naked body and luscious dick.

Then I took it too far. Maybe it was all the wine, I don't know. But that's no excuse.

Michelle texted me, telling me she'd be home in a few minutes. I thought it would be funny, and exciting, for her to walk in on him while he was masturbating, and show my man off to another woman. So I ignored her text and instead encouraged Tommy to keep going. I figured he'd get off on it too, right?

Wow, was I wrong! She was pissed when she walked in! And worse, so was Tommy! He drove off in a rage.

I suppose I can't blame him. If he'd have set me up to have one of his friends walk in while I was naked without my knowledge, I'd be pretty upset too.

I feel fucking terrible about it. I just hope they can both forgive me.

****

Had a talk with Michelle and just got off the phone with Tommy. Things have calmed down and both of them have accepted my apology.

Still, I feel nauseous. I didn't realize how much I enjoy having Tommy in my life until I almost blew it.

I love that we've both been able to open each other up to exploring our desires, and he's always been so caring and patient, even when I've been a total cock tease.

I guess I'm starting to admit to myself that I have a kinky side, and it's been incredible sharing it with him. Plus, on the non sexual end, we just seem to get along and share other common interests, despite the age difference.

I've always found older guys attractive, and Tommy is certainly more mature than all the guys my age. I can't seem to meet even one who isn't a complete douchebag, although, to be honest, I haven't really tried since Jim dumped me last summer.

Is this gonna be just a fling? I can't imagine it being a long term relationship. It would certainly be...complicated.

My mother would have a fit. God, I hope that's not why I'm seeing him, just to spite her. That would be terribly unfair to him.

No, that's not it. I have...feelings for him. Maybe even love him. Not in that "'til death do us part" sense, no, God no! I'm way too young to be thinking about marriage! I have career plans and life goals that certainly don't involve settling down and starting a family.

But I care for him. A lot. I just hope I didn't hurt him with my stupidity.

We both agreed a little space right now will be good, but he's agreed to get together again soon to talk more. I'll at least sleep a bit better now.

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Wednesday 5/19/21

The nude art project was today. I think I did really well on it.

It wasn't as weird as I thought it might be. And certainly not erotic AT ALL.

The model was okay looking I guess. Not a bad body. I heard a couple of girls giggle when he disrobed; I guess my "practice" sessions with Tommy made me more ready for it.

But there was no sexual energy like there was with Tommy. And certainly no erection nor cumshots!

The only arousal I got from it was thinking about how I'd rather be sketching Tommy's long, beautiful cock than this guy's shrunken, flaccid one. I had to chase that thought away quickly to focus on my work.

Speaking of Tommy, he texted me earlier, wishing me luck on the project. Gonna give him a quick call to fill him in before I gotta leave for work.

I'm really beginning to hate working at the diner. Not the place itself, or my boss. But it's just becoming exhausting, and the pay isn't all that great.

I'll be quitting for the summer break anyway, I suppose. But I seriously have to find something better to earn money next semester.

Mom still refuses to help me out. You'd think having a new boyfriend would help chill her out, but nope. She's still as uptight as ever. I'm really not looking forward to going home this summer. Especially if he's gonna be around.

I've been thinking more seriously about Only Fans again. I suppose what I need to decide is just how comfortable I am showing off my body to a bunch of strangers for money. And whether I can safely protect my identity. I'll have to talk with Michelle about how she handles it when I get a chance.

Shit, getting late! Gotta go. More on that later.

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Friday 5/21/21

Quick entry; Tommy is on his way over. We're gonna go out, get some food and talk.

I've missed him this week. And I really wanna make it up to him somehow.

We won't have any privacy here for the time being with Michelle around. I'm seriously considering suggesting going back to his place.