The Jenna Arrangement Pt. 17

FORWARD:

With Jenna now home, we shift focus and continue the story from her point of view. As with the prequel chapter, it is told through entries in her diary.

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

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Sunday 5/30/21

Well, I'm home for the summer. And it's already been an excruciating experience.

Mom showed up with her boyfriend along for the ride. Just what I needed, to be stuck in the car for four hours with the asshole who spent the entire Christmas break leering at me every time he came to visit.

Worse yet, apparently he's moved in with Mom for the summer!

His name is Richard Goatz, but purposely goes by Dick. Not Richard, not Rich, not Rick.

Dick Goatz. Seriously.

I shouldn't be surprised Mom is still seeing this guy. He has money; runs his own law firm or something. He recently sold his house and is having a new one built. Until it's finished, he'll be living here.

So now I'm stuck with him around.

It wouldn't be so bad if he wasn't such a complete creepazoid. Every time he looks at me I feel like he's trying to see through my clothes.

Maybe it's just my imagination. Or maybe, subconsciously, I just don't like seeing Mom with another man.

They seem happy enough together, so I guess I'll try and be happy for her. But knowing Mom the way I do, this relationship probably has more to do with the size of his bank account than the size of his...no, I won't go there. I don't want to be cruel. I just know that ever since Dad died, Mom has been looking for someone else to take care of her and keep her in the lifestyle she's become accustomed to. And I know she can't have much of the insurance money left.

But I'll try my best not to be judgemental.

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Monday 5/31/21

Spent most of the afternoon setting up my social media accounts to start promoting myself and build a following for Only Fans.

I had to create all new accounts of course; I don't want my friends and family on my personal pages to see the content I'm gonna be posting.

I'll just need to be REALLY careful not to mix up my accounts when I log in. That could be embarrassing.

I haven't actually created any content yet. I'm still debating on whether to show my face. Or how much more I'll show. I can't go naked on some of these other apps anyway, but it's still kinda scary to put myself out there.

It's also rather exciting though.

I'm gonna reach out to Michelle again, pick her brain on the best way to get started. I may also just practice taking some sexy shots and send them to Tommy, get his opinion. I'm sure he'll appreciate them LOL.

I miss him already. He should be home from work by now. I'm gonna send him something sexy, just to let him know I'm thinking about him. Maybe he'll be up for a video chat later.

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Friday 6/04/21

So after spending some time talking with Michelle, then Tommy, I've decided how to move forward with my Only Fans.

I've decided I'm only going to allow my accounts to be viewed by countries outside the U.S. It's going to limit my customer base BUT it will ensure I won't run into privacy or employment issues in the future.

It also makes me more confident about my decision to show my face. Michelle said it will help me make more money, and Tommy confirmed that most guys prefer to see the woman's face.

Tommy has been very supportive and helpful with all of this. And he's actually come up with a really good idea.

Since I'm still unsure of just how hard-core I'll go, he's encouraged me to play to my strengths. I enjoy teasing guys, getting them worked up, and getting them to masturbate for me. So Tommy has suggested that I make Jerk Off Instruction / Encouragement type videos.

Even if I decide not to get fully naked in my content, I can create scenarios and scenes that encourage my audience to play with me. He said if the men watching my videos believe that I'm actually getting off on knowing they're masturbating to me, they'll be more than happy to do it, even if I'm not fully naked.

Michelle also had several great suggestions.

The first was to create two different accounts; one a free account, where I would post sexy but not fully nude content, allowing guys tp see me and provide a hint of what they'll get on my main page to encourage them to subscribe.

Another idea was to offer custom video requests (for a price, of course) where I use the customer's name, speak to them directly, and perhaps show more. I'll have to think about that.

Her third idea is one I definitely will do. She suggested offering free "dick ratings," encouraging new subscribers to send me dick pics or even video clips of them cumming for me. She said I can always charge for the ratings later as my page grows, but it's a great way to draw in subscribers because guys love sending dick pics.

I like that idea. Even if they're not the best looking guys or biggest dicks. I always enjoyed getting men aroused for me on Omegle, and now I can charge them for it, so it's a win / win.

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Saturday 6/05/21

It's already getting creepy around here.

Woke up having to pee, but Dick was in the shower. So I waited in my room until I heard him leave the bathroom, then waited a full minute more to make sure he was gone.

But when I opened my door, there he was, standing in the hallway wearing nothing but a towel, like he was waiting for me to come out or something.

If I'd known he was there I'd have made sure to put on some shorts. My nightshirt was more than long enough to cover my panties, but still, the way he looked at me made me feel naked.

Later, this afternoon, I decided to spend some time out by the pool. Mom went out shopping or something, but Dick was still here. I caught him several times looking at me through the patio doors.

I totally regretted wearing my bikini. I just wanted to work on my tan a bit. I'm used to guys looking at me, especially at the beach or something, but he was just so damn obvious about it.

But it got worse when he decided to join me. Wearing a Speedo.

I don't like body shaming, but frankly I think Speedos look ridiculous even on muscular men. And Dick doesn't fit that category.

There's only one reason men wear that ridiculous bathing suit: to draw attention to their dicks. And from what I saw, (despite my best efforts not to) Dick doesn't have much of one.

"It's such a beautiful day, you've certainly got the right idea. Mind if I join you?"

I did mind. But I was polite and just shrugged, then tried to ignore him when he took the chair right beside me and oiled up his hairy body.

"My new house will have a much larger pool," he bragged. "You'll have to come visit when it's done. It will have its own bath house, and the yard is so private you could sunbathe nude if you wished; I certainly plan on doing so myself."

Just the thought of it made me gag. Not taking my lack of response as a sign, he kept right on talking. "I often sunbathe nude on the beaches in Europe when I travel. They're far less uptight and repressed about nudity than us Americans. Your mother and I are planning a vacation overseas in the fall. Too bad you'll be back at school; I'd love to take you to the beaches there."

"I bet you would," I grumbled. I'd had enough. I made an excuse about having things to do and got the hell out of there.

As I headed to the bathroom to shower, I noticed as I passed my bedroom that the door was open a crack. I was pretty sure I'd closed it before I went outside.

After my shower, I went back to my room, and that's when I discovered that my panties were missing.

I'd taken them off and put them right on the top of my hamper in the closet this morning. When I went to throw my swimsuit in there, they were gone.

I sorted through all the clothes, just to be sure, but there was no sign of them.

I'm livid, but don't know what to do. If I confront Dick about it, he'll just deny it of course. But there is no other explanation. He snuck into my room and stole my panties!

I could go to my mom, but I doubt she'll believe me.

I'm going to have to think this over carefully.

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Sunday 6/06/21

I finally managed to get Mom alone for a few minutes this morning and told her my suspicions about Dick stealing my panties.

She was PISSED. But not at him. She accused me of lying and worse, of being jealous! "You just don't like seeing me happy, do you?" she accused. "Can't stand the idea of me having someone besides your father!"

I've been in my bedroom crying ever since. To make matters worse, Dick is out by the pool again in that stupid Speedo.

I've only been home three days, but I already feel trapped here. I should have taken Tommy up on his offer to stay with him.

I want to talk to him about this, but I don't want him to worry about me. I'll have to deal with this on my own, for now.

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Monday 6/07/21

Finally had the place to myself for the day! Dick went back to work and Mom was out doing...well, whatever it is she does all day.

Since I had some privacy, I decided to work on content for my social media apps and Only Fans.

Going through my wardrobe has made me realize just how few truly sexy items I own. I'm certainly going to have to invest in more lingerie as this gets going, as well as a decent stand for my phone to shoot videos, and some better lighting. But one thing at a time, I guess. For now, I'll just have to make do.

I decided on my pink crop top and matching panties to start. The same outfit I wore for Tommy after our first date at the lake.

I took a bunch of selfies in various poses. I was nervous at first, but started getting into it after a while, thinking about how I was going to be showing these online to complete strangers. It's frightening, yet also really arousing at the same time.

Then I changed into my "Yes, Daddy?" romper and took a bunch more. It's more cute than it is SEXY, really, but it has that "innocent yet naughty" thing going for it.

Looking through my first few pics, I realized just how small my boobs look in photos. I started playing with my nipples to get them to pop more in the photos. They got hard within moments.

I set the timer on my camera to take a picture every ten seconds, then set it up carefully on my night stand.

This left my hands free, and I started caressing my body over the romper, grabbing and squeezing my breasts, running my hands across my belly then down between my legs, over my now tingling pussy.

I tried to maintain eye contact with the camera as I teased myself, making pouty or kissy faces sometimes.

I imagined Tommy was on the other end, watching me, and that really helped get me in the mood.

I sat back and opened my legs, still aiming at the camera. The romper had ridden up my slit and now showed a very clear cameltoe, outlining my pussy perfectly. I let the camera take a few pics then pulled the crotch of it up even tighter, exposing swollen pink vulva on both sides. There was also a small wet spot forming clearly on the thin white fabric still covering my labia and vaginal opening.

After a few more pics, I moved to my hands and knees and aimed my ass towards the camera. I wiggled my butt and teased myself as the camera clicked, not really sure how the pictures were coming out, but I'd sort through them later.

I was close to cumming already but wanted to hold off on it, because I had an idea that I felt I was now ready to try.

I wanted to shoot my first full videos.

After rearranging the camera again and setting it to video mode, I got out the new vibrating wand Michelle had given me and placed it to the side, just off camera.

I sat facing the camera and looked at myself in it. My cheeks were already slightly rosy and my hair a bit disheveled from everything I'd been doing so far, but I decided it was the right look for what I wanted to do.

Scooting forward just a little more, I took a deep breath, let it out, and tried to relax. But my hand still trembled a little as I reached forward to hit Record.

I sat back and repositioned myself, counted to three silently, then began:

"Hi guys, I'm Jenna..."

I realized my mistake right away. I'm not going to use my REAL name of course. I'd decided to go with my middle name instead. I had to start over:

"Hi, guys, I'm Robin. Thank you so much for checking out my Only Fans. I wanted to tell you a little bit about me, and let you know what you can expect to find on my pages.

"I'm nineteen, turning twenty soon, and in college. I'm also an artist, and a bit of a geek. Being honest, I'm really nervous. This is my very first video. But I'm also really excited to share it with you. I love the idea of you watching me, getting excited for me. Turning you on turns me on, so much.

"If you're watching this, you've already subscribed to my free page. On it, I'll post regular fun, sexy selfies and video clips."

I turned on what Tommy calls my "princess" voice and slowly started running my hands over my body as I continued: "We can have lots of flirty, sexy fun together."

I reached over and grabbed the wand. Turning it on, I ran it back and forth between my already swollen nipples, leaning forward to give the camera a closer view of them pushing up through the fabric.

"If you love a good tease, I'm definitely your girl," I purred.

Slowly I ran the vibrating wand down my stomach, pausing over my pubic mound. Moving in closer still as I ran the wand around, I could see, faintly, the shadow of my thin red hairs, the romper conforming snug against my mons, highlighting it's rounded curve.

I was already moaning as I sat back again and moved the wand still lower, over my clit, which was just off camera. I squealed with pleasure as the vibrations shook through me.

Recovering my breath, I continued my little monolog:

"Can you tell how turned on I'm getting? I hope so. I'm so fucking horny right now. I can't wait to cum for you. If you really wanna see more, you can purchase the rest of this video for a ten dollar tip, or, better yet, subscribe to my pay account in the link below for just five dollars a month. You'll get the rest of this video immediately, and more just like it every week. Plus we can chat and flirt together. I really wanna..."

I squealed again uncontrollably as the vibrator continued it's relentless stimulation. My face flushed as I giggled with laughter. "I really wanna get off with you. Can't you tell? I'm already so wet. You wanna see it, don't you? You wanna cum with me, right? Subscribe right now, and you can. I promise I'll make it worth it."

I gave the camera my sexiest look, held my pose for several seconds, then reached over to stop the camera.

I caught my breath for a few moments before starting again. This would now be the video they had to subscribe or tip to see:

"Thank you so much for subscribing. I'm so happy to see you here. Did my intro video tease you that much? I promised you more, didn't I?"

It felt a little odd, talking to a camera. So I tried to imagine I was talking directly to Tommy, to use him as my inspiration and put on a show the way I would if he were watching.

"Sit back and relax. It's just you and me now. No stress, no distractions."

Easing myself back on the bed, I parted my legs slowly as I continued: "I promised to show you just how turned on I was, didn't I?"

I could see myself on the screen. My romper was still snug up against my pussy, the outline of it clearly defined by the wetness that had soaked into the fabric, making it even more see through.

I ran my fingers over myself slowly. "See how wet I am already? And I only just started. But I need you to play with me. Go ahead, take your cock out for me. I want you to stroke it, to play with it, while I play with myself."

I couldn't believe how much I was getting into it. I rubbed my pussy faster, my juices seeping out of it. Seeing myself in the camera made it even more exciting, knowing men would be watching this, watching me touch myself while they jerked off.

Suddenly my hips were shaking as I had my first orgasm. I had to struggle to keep myself in frame as I gasped, squirmed and squealed.

I slid my fingers under the gusset of the romper, coming away with strands of my gooey drippings that I held out towards the camera. "Fuck, I came so hard already, just knowing you were watching me. Look how creamy you made me!"

I sucked my cream off my fingers, slurping loudly and running my tongue around them like I was teasing a cock. "Mmmm, wish you could taste this. It's so good."

Feeling bold, I grabbed the wand and turned it back on, aiming it over my clit. "I'm not done yet. I need to cum again, and I want you to cum with me, okay? I want you to stroke yourself however you like, whatever makes you feel best. But don't cum til I do, okay? I'll tell you when, I promise."

Holding the wand over my clit, I pinched and twisted my nipples with my free hand, keeping as much eye contact with the camera as I could as I wantonly masturbated for my future audience.

I kept thinking of Tommy, and tried to look at my camera the way I would at him.

My breath was hitching as I gasped from the building pleasure, making it difficult to speak, but I continued as best I could:

"You're getting...harder, aren't you? I know you are. That excites me, so much. So...so much. Fuck, my pussy is aching just thinking about your throbbing cock."

I had a sudden flash of an idea:

"I wanna see your cock. Take a picture of it, right now, and send it to me. I don't care what size it is, I love all shapes and sizes. I wanna see how hard you are for me, right...now!"

The vibrator was sending intense waves through my clit that reverberated through my body. I was shivering with excitement.

Emboldened, I unsnapped the crotch of the romper and pulled it away, exposing my pussy fully.

"That's what you wanted to see, right? My pretty pink pussy? My natural red bush?"

I scooted closer and spread my labia open, just in time for a fresh glob of cream to push its way out and slowly drip down the crack of my ass.

I kept the wand on my clit, but now my other hand was rubbing my pussy lips, smacking at them, spreading them open, giving my voyeuristic audience a full view.

My legs started to shake as my orgasm built up within me.

"I'm so close now...so close. Are you gonna... cum with me? Keep jerking it for me, don't stop...don't stop. Yes, that's it, I know you're close too...oh, fuck, here it comes, oh fffffff...."

My orgasm hit hard, rocking me uncontrollably. I forgot all about the camera as my eyes rolled back and my body shook. Unable to hold myself up any longer, I collapsed back on the bed, gasping for air as my body continued to tremble in orgasmic waves.

I lay there quietly for a few moments, catching my breath. Then I remembered the camera was still recording.

I sat up. With an embarrassed giggle, I addressed the camera one last time:

"Whew. Wow. That was fucking amazing. I hope you came as hard as I did. Don't forget to send me your dick pics, I want to see them. I promise I'll respond back as soon as I can and tell you what I think of them, okay? And I promise we'll do this again real soon. See you then."

I paused for a few seconds, then stopped the recording.

I couldn't believe what I'd just done. Or how hard it had made me cum.

Now the real question is: will I be brave enough to actually post it?

It's going to take me some time to edit the clips. Perhaps after, I'll send them to Tommy and see what he thinks. I really didn't plan on being that brazen. That said, it felt natural and right. I hope he thinks so, too.