The Jenna Arrangement

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE.

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Jenna and I spent the rest of that afternoon together. After the seriousness of the earlier conversation, we switched to more light hearted chit chat; favorite movies, music, foods, stuff like that. We had a lot more in common on many of those things than I'd have expected given our age difference. I think a lot of it may have had to do with her father's influences.

We probably could have talked all night, but Jenna got a text message from her roommate saying she was coming home early from her boyfriends. I thought it best that I make my exit before she arrived.

Before I left, I retrieved my phone from my car. We made sure we'd saved each other's phone numbers and exchanged email addresses and social media pages. Jenna even introduced me to Snapchat, an app I'd heard of but never used. She helped me set up an account and added herself as a friend. I was still rather confused by the whole thing, but Jenna promised she'd walk me through it, sending me a test "snap" right then so I could see how to open and view them, etc.

We parted with the promise to get together again soon, hopefully by the next weekend. We also parted with a warm hug, and another soft kiss from Jenna that she allowed me to reciprocate for a few moments before breaking.

I walked to my car with a spring in my step I hadn't had in a long, long time.

Just as I got behind the wheel I heard a notification from my phone. It was another Snapchat from Jenna. Opening it, I saw an adorable picture she'd apparently just taken. It was one of those Selfie style pics young women seem to be masters at. The camera angle was from above looking down, and she was making a cute little kissy face. She'd tied her Stones tee shirt up in a knot, exposing her firm belly and making the shirt form tighter around her small, perky breasts. To top it off, she'd put some silly cat ears and whiskers filter on her face.

I viewed the picture for several seconds, smiling, and then it was gone, as she'd warned me would happen.

"Smart girl," I said, still grinning. "I can't save anything you send me, can I?"

The smile never left my face the whole ride home.

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I spent most of Sunday getting things done around my apartment and running some errands, including restocking my empty refrigerator.

Finally settling in around 10pm, I was about to scroll through my multiple streaming services to find something interesting to watch, when I received a Snapchat from Jenna.

Opening it eagerly, I saw she'd sent another picture. She appeared to be sitting up on her bed. Her hair was pulled back into a short ponytail. She was wearing a tiny white, loose fitting half shirt that clearly showed off her braless, pert little breasts. Her green eyes had a playful glimmer to them, and on her lips, a suggestive smile.

The text with the picture read: "I'm bored. Play with me?"

I felt at once excited and nervous. Excited to hear from her, and to have her send me such a cute, sexy picture. Nervous, because I wasn't quite sure how to proceed. It had been a long time since I'd played the sexting game, if in fact that's even what this was. Maybe she was just teasing me, or testing me.

"Don't overthink this, dumbass," I told myself. "Just roll with it."

My fingers hesitated over the Send Chat section before I finally typed a reply:

Me: "It's a school night, young lady. Shouldn't you be getting ready for bed? 😉"

Several seconds went by, then a new picture popped up. Jenna was now up on her knees on the bed. At this angle I could see the light blue boy shorts she was wearing. Her free arm draped across her firm belly with her hand resting suggestively just over her mound. Her face had a sad, adorable pout. Beneath the picture there was a text.

Jenna: "I'm not sleepy, daddy. I wanna play."

I felt my cock already responding.

"DADDY???" I thought. "Are we role-playing?" Looking back at my first comment, it's not what I'd intended, but I could see how she'd interpreted it that way.

I decided to run with it, but cautiously.

Me: "What would you like to play, princess?"

Shit. Did I really just type "princess?" Isn't that kinda creepy? But I'd already hit Send, no taking it back now.

Several more seconds went by, then another pic. Jenna was now leaning forward, offering me a view down her shirt. Her pale breasts were hanging loose under the fabric and I could almost see where they ended in her nipples, but not quite. She'd also somehow managed to thrust her ass up high enough that I could see the round curves of it, defined nicely by the form fitting boy shorts.

Jenna: "Let's play You Show Me Yours, I'll Show You Mine. 😁"

My erection was full and throbbing now, tenting in the loose fitting cotton shorts I was wearing. On a whim I took a picture of it and sent it along with a caption.

Me: "Is this what you wanted to see, princess?"

Seconds ticked by, then her new pic arrived. Jenna didn't have a lot of cleavage, but what she had was on full display, the camera looking downwards towards them. Her face had that mischievous grin again, with one finger poised teasingly by her lips.

Jenna: "Did I do that? Sorry, daddy."

Me: "Don't be. You know daddy loves looking at you."

Jenna: "Can I see it, daddy?"

Thinking for a moment, I adjusted my shorts enough so that only my tip was poking out, took another pic, and sent it.

Jenna's pic came back; a sad, pouty face.

Jenna: "Daddy! Show me more! 😾"

Me: "I need to see more from you first, princess. That's the game."

There was a long pause in which I worried perhaps I'd asked too much, remembering Jenna's tale about the pushy guys on Omegle. Then Jenna sent another picture.

Her top had been completely removed. Her free hand was pushing her boobs together, covering the nipples in a perfect Hand Bra pose. Goddamn, she was good at this!

Jenna: "You mean like this, daddy?"

Me: "OMG." (Stupid, I know. But it's all I had at the moment.)

Jenna: "Your turn, daddy."

"Shit, I'm terrible at this," I thought. As much as my cock was throbbing, I didn't wanna go straight for the typical dick pic. I wanted to see if I could beat her at her own game.

My mind raced for several moments before coming up with an idea.

I stood up and threw off my clothes. Standing there nude and erect, I moved my phone camera around at several different angles til I got just the right shot.

I worked out pretty regularly and while I wasn't muscle bound, I had some good definition in my abs. Tweaking the angle of the camera just a little more, I managed to take a picture that went from my chest to my lower stomach and abs, where it formed that "V" cut I'd read many women enjoy seeing on a man. The picture cut off at my pubic hair just above my penis. I sent the pic, grinning at my triumph.

Jenna's reply came back seconds later:

"🤤 😜💘 💦"

Me: "Your turn, princess."

A full minute went by. Then another. I was about to reply again to make sure we hadn't been cut off when her picture finally came through.

Jenna, on her knees on the bed, holding her camera above her and to the side, looking directly up into it. Her body was bent forward slightly.

She was completely nude.

Somehow, she'd managed to angle the shot so that I could see her breasts but not exposing the nipples. They were magically just out of view.

She'd removed the boy shorts, and I could see the round curve of the side of her bare ass. Her legs were close enough together to conceal her vagina. She'd managed an absolutely perfect picture of a completely nude woman just barely managing not to expose everything.

Fuck. I was defeated. How do I top that?

Jenna's next message came through: "I'm waiting, daddy."

I had one last idea. I put my free hand over my cock. It fought me as I pushed it downwards, not wanting to bend. Again, after struggling several times to get the right angle, I snapped a pic that showed me nude but just barely covering up my erection with my hand.

Sending it, I waited.

Any hopes I'd had that I'd win this game were dashed when her final pic came in quickly.

Jenna, her legs completely spread. The palm of her hand resting over her mound. Little tufts of red hair poking out from underneath it. Her thumb and pinky extended out to either side. Her other three fingers pointing downwards, just barely covering her slit. It was difficult to tell, but I was pretty sure the tip of her middle finger was penetrating her vagina. I just couldn't actually see it.

My head hung in defeat. But my grin was wide, and my cock was twitching.

Me: "I concede. I know when I'm beaten."

Jenna sent several laughing emojis, then, "Daddy, show me your...🍆"

I knew enough to understand what that meant, and I aimed my camera at my cock. It was standing tall and firm as if posing for the picture. The tip was glistening with precum.

I sent the pic: "All for you, princess."

Jenna sent an array of various emojis; smileys, starry eyes, drooling, hearts, and several I wasn't sure of.

Then she messaged: "You wanna cum for me, daddy?"

"God, yes," was my instant reply.

I saw an icon pop up; Jenna was sending me the live video link. I clicked it to see a close up of her smiling face.

"Hey," I said, a little shakily. I hadn't done video chat in a long time either, and I honestly wasn't sure if we were still role-playing at this point, or dropping that pretext.

I received my answer immediately. "Hey, daddy," said Jenna. "Got you all worked up, huh?"

"You sure did, princess," I said, trying to ease back into the role.

"Show me, daddy," Jenna purred, "show me how turned on I got you."

It took me several tries to find the right camera position so that Jenna could see my cock and my face at the same time.

Her eyes went wide as my cock came into frame. "Wow, it looks so big, daddy," she whispered, playing her role to perfection.

"You want daddy to cum for you, princess?" I asked.

"Yes, daddy," she said softly.

I froze for a moment, trying to figure out the best way to do this. I wound up setting my phone down on the end table next to me, propped up against the lamp, then moved the chair enough so that most of me was in frame, facing the camera, and I could also still see Jenna's face.

So far, that's all Jenna was showing. She appeared to be sitting up now, and still topless. But all I could see below her face was her bare shoulders and a hint of where her freckled cleavage started.

Her eyes stared directly at me through the screen, her innocent yet wicked grin once more lighting up her face.

"Play with it for me, daddy. Jerk it for your princess."

I sat back, took my aching cock in hand, and stroked.

Jenna watched me masturbate in silence, but her eyes and face spoke volumes. She was enjoying her victory, no doubt. Even though I was the "daddy" and she the "princess," she'd still managed to keep complete control of the situation.

I wanted to see more of her, of course. But I wouldn't dream of asking. It would be against the rules. Rules we'd never officially discussed, but I knew instinctively, based on all that had come before.

Feeling a bit dry, (and yet again forgetting to have lube handy) I spit on my palm several times, using it to lubricate my head and shaft.

Jenna grinned. "Bet you wish that was my wet stuff on you, huh daddy?" With that, she held up a hand towards the camera.

I had to lean in to see better. Her fingers were slick and glistening, and as she parted her fingers, I could see a sticky strand of thick liquid strung between them.

Jenna had been touching herself, I realized in astonishment. Touching herself while watching me jerk off to her.

I ran out of words, and could only groan in reply.

Jenna's hand dropped out of sight, and now I was imagining it between her legs, working her wet pussy, fingering and rubbing herself out of my view.

Her face became tense, her eyes fluttered but only rarely strayed from the screen. I could sense more than see her actual movements, only the slight shake of the camera giving away her secrets.

"Daddy," she moaned softly, "I'm gonna cum soon daddy. I want you to cum with me, ok? Please, daddy?"

I sat back again, added more spit to my palm, and furiously continued to jerk.

My hips bucked up from the seat of my chair as I felt my climax approaching. Jenna's eyes went wide as my first blast of cum erupted, then rolled back as her own orgasm took her.

Her moans and squeals echoed from the tiny phone speaker, not quite drowned out by my own growls and grunts.

As I regained my senses, I focused back on Jenna. Her eyes were closed and her face was blissful. I could tell she was still pleasuring herself, riding the waves of a smaller, more subtle orgasm, and I sat silently watching her, allowing her to finish in peace.

Eventually she opened her eyes, and grinned a happy, contented grin at me.

I considered speaking for a moment, but knowing Jenna better now, I remained silent, and waited.

"Wow," she spoke at last. "I'm finally sleepy now, daddy. Thank you for playing with me."

"Any time, princess," I said softly.

Jenna blew me a kiss, and then she was gone.

I sat there in satisfied wonder for a while.

"Don't question it, just enjoy it," I reminded myself.

I was about to get up and clean the mess I'd made when my phone buzzed again; one last message from Jenna.

Jenna: "That was fun. Goodnight, daddy. 😚💖"

Shaking my head, I sighed happily, then replied.

Me: "Goodnight, princess. Sweet dreams."

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Afterwards:

Much like my male protagonist, I am aware of the existence of Snapchat but not entirely familiar with exactly how it works. I knew enough about it's features to understand it's the one Jenna would choose; a way to send and share things without leaving evidence behind.

If I have described some features inaccurately, you can blast me in the comments I suppose. Or, you know, just stop nitpicking and enjoy the story.

For those of you who aren't into the "daddy" thing, fear not. It was a fun role-play for them, but I don't think it's going to become a central theme. Although I can't promise it won't come up again. Jenna is...unpredictable.

Jenna has been, hands down, the funnest character in all of my stories to write so far. I honestly have no idea what she'll do or say next until it happens. I can't wait to see what she has in store for Tom next.

To be continued.