The Jenna Arrangement Pt. 13

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Tom & Jenna discuss their future, and their fantasies.
5.5k words
4.78
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14

Part 14 of the 29 part series

Updated 03/16/2024
Created 08/22/2021
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Djmac1031
Djmac1031
846 Followers

FORWARD

Chapter 12 ended with our happy couple making love for the first time and confessing their love to each other.

Chapter 13 picks up shortly after.

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

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I came back to the bedroom after using the bathroom and freshening up a bit to find Jenna sitting up in my bed, writing in a thick, red covered notebook.

She looked so beautiful with the sheets pulled up to her stomach, leaving her naked breasts exposed. I felt myself wanting her again, despite having just cleaned up from our first love making. Although I'd probably still need a little more recovery time.

Jenna looked up from her writing and smiled. "Oh hey. Almost done, gimme just a minute."

She finished scrawling a few more lines and then closed the notebook. "My diary," she explained upon noting my curious look.

"Ah. Anything good in there about me?" I asked.

"Maybe," she grinned.

I slid into bed next to her, just as naked as she was. Her warmth was comforting. It had been far too long since I'd had a woman I actually cared for in my bed.

We kissed for a few moments, her lips soft and supple. I was already feeling a stirring between my legs despite having just cum maybe fifteen minutes ago. I couldn't remember the last time a woman had turned me on so much as to be this excited again so quickly. It had certainly been awhile.

Still, I didn't want to rush things. She might need some downtime after her own marathon of orgasms. And I wasn't fully functional just yet anyway. Close, but not quite.

So instead of trying to take things further, I asked about the diary. "So what else is in there? All your deepest, darkest secrets, desires and fantasies?"

"Don't tease," she shoved me playfully. She then turned slightly more serious. "I started the diary after dad died. A way to keep my memories of him alive by writing them down. From there it's just, you know, somewhere to gather my thoughts and feelings and keep a journal of special moments and stuff."

"So you were writing about tonight?" I asked.

"Well, duh," she giggled. "After all, it was definitely a special moment." Her eyes lit up lovingly as she kissed me again.

"Well, I'm honored that you considered it special enough to warrant an entry," I smiled.

"Oh you're in there quite a bit, actually. You can read it if you want," Jenna offered.

"That's okay," I declined, "I think some things should remain private. That's for you, not me."

Jenna nodded appreciatively. "I suppose so. Although I have no real secrets anyway. There may be a few things in there I haven't told you, but nothing I wouldn't be willing to tell you."

"Anything juicy?" I joked.

"Oh, you want juicy, huh?" Jenna smirked. "Okay then, let me think...ah! Okay, here's one: Trish and I masturbated together once."

My jaw dropped. "Really???"

Jenna laughed. "Yes, really. We'd been cock teasing guys on Omegle for a while. We were both pretty high. And pretty horny."

"How far did you two go?" I asked excitedly.

"Settle down, cowboy," Jenna laughed. "All we did was masturbate. No lesbian stuff. Well, okay, we were making out earlier, but that was for Omegle. We just took out our vibrators and got ourselves off. "

My eyes started to glaze over, imagining the scene, and more. Jenna turned my face towards hers. "You're fantasizing about it already, aren't you?"

I chuckled as I came back to reality. "Guilty. Sorry. But you know I'd have loved to have seen that."

"Oh I'm sure," Jenna said. "What else were you imagining? Trish and I going down on each other? A threesome? A double blowjob?"

I suddenly felt a bit flustered. "Look, I'm sorry, I shouldn't be thinking about your best friend like that, it was just..."

Jenna cut me off. "Hey, relax. It's okay. I'm not upset by it. I have my fantasies, too. I think it's healthy to talk about them."

I breathed a sigh of relief. "Thank you. It's not like I actually expect that kind of thing to happen. But, you know..."

Jenna grinned. "Yeah, I know. You're a guy. You can't help thinking about it. But hey, who knows? Some fantasies can come true, if everyone is...agreeable to them." I looked at her, surprised.

"I'm not making any promises here," she cautioned. "Just saying I'm...open minded enough to talk about them."

"Fair enough," I said. "Is that the kind of thing you fantasize about as well?"

"Not until recently. Trish is my best friend, and of course now I have you. Two people in my life I love and care about and feel comfortable with. So, yeah, sure. The fantasy has at least crossed my mind."

I was intrigued by the possibilities, to say the least, and by her candid openness.

"I get we're just...talking, here, not actually planning anything," I started, "but I just want to make something clear. I'm not looking for another woman. Trish is a nice girl, and sure, I find her attractive. But I don't have any feelings for her. I love you, and I'm more than happy with just you. And I'd never want you to think I'd be unhappy with what we have, just me and you."

Jenna smiled warmly. "Thank you. But you think too much. I'm not worried about any of that. You've never given me a reason to. If anything, I've been the one encouraging things with Trish. Letting her tease you, letting you jerk off for her, I've been...enjoying it. And I'm discovering that I don't find the idea of sharing her with you, and you with her...objectionable."

"That's...interesting to hear," I said neutrally. "I suppose in the spirit of honesty here, I'll admit that I'd be open to sharing more experiences with Trish, but only in whatever way you feel comfortable, and with the understanding that nothing happens without everyone's full consent and comfort."

Jenna again nodded. "Of course. And don't forget that includes your comfort levels, as well as Trish's. I'm honestly not sure how far she'd be into taking things either. But I can tell you she's not interested in you as anything more than a friend, with a few benefits, granted. We've already talked about it a little bit, after that fiasco with Michelle walking in. Trish made it very clear to me she's not interested in interfering or inserting herself in our relationship. She's open to having some fun, but told me she has absolutely no intentions of trying to divide us."

"Good," I said, "as long as everyone is clear on where we all stand."

"I know I am," said Jenna. "Trust me, I've thought about all this a lot lately the last few weeks, especially as things have escalated. I don't know how far I'd be willing to take it all just yet. But I have a kinky side, too, it turns out. And I've been having fun exploring my fantasies, and my boundaries."

"What other fantasies do you have?" I asked. "Things you've thought about exploring? Even if only in your imagination."

Jenna hesitated as if unsure how to answer. "Hey, it's just me. And we're just talking. No judgment here," I assured her.

Jenna sighed. "Okay, why not? So you know how you like to be naked in front of women, right? And you know I enjoy getting guys off letting them look at me. I was tempted several times to show more of my body to the guys on Omegle, but my fear they'd somehow be able to capture the image or video and put it online kept me from doing it.

"But I've fantasized about being naked in a crowd, or in a room full of men, or on a nude beach or something. Showing off my body, knowing I was turning guys on, looking at me. Not letting them touch me, or fuck me. Just...exposing myself, knowing they were looking, getting excited. Kinda like what I did to you yesterday. Although of course, I did wind up having sex with you."

Jenna looked at me to get my reaction. "That's actually a pretty normal fantasy," I said. "Everyone wants to be the object of desire sometimes. And in a safe environment, it could be very erotic, and empowering. And it's not exactly an impossible fantasy to fulfill, you know. I could think of at least a few ways."

Jenna looked surprised. "You're saying I should try and make that happen?"

I smiled warmly. "I'm saying that if that's something you truly wanted, we could find a way to make it happen. You've made it happen for me, so of course I'd be open to making it happen for you."

"Wouldn't you get jealous of other men, you know, looking at me? Getting turned on, seeing me naked?"

I thought for a moment before replying, "I'm gonna be honest in saying I'm not really comfortable with the idea of sharing you with another man. A double standard, perhaps, given your consideration of sharing me with Trish in more than just a visual way."

"I'm not at all interested in having sex with other men," Jenna interjected. "The threesome idea with you and Trish is one thing, but I have zero interest in fucking other people, especially strangers."

"Well, if we're talking simply about letting other men see you, get off to you," I continued, "I don't have any objections to that. Most men want other men to desire the woman they're with. It's an ego thing in a way. 'Yeah, you can look, but she's going home with me.' That kind of thing."

"I get that," said Jenna. "Us women do it too. I really did get off on letting Trish see your cock, knowing she couldn't have it but I could."

I laughed. "Yeah, you get it alright."

Jenna seemed contemplative. "What are you thinking?" I asked.

"What would you think about me," Jenna paused, hesitant, "starting an Only Fans page?"

"Are we talking seriously, or still fantasy here?" I asked.

"Seriously," said Jenna. "I've been considering it for a while now."

I was quiet for a few moments, sorting my thoughts on this new surprise.

"Don't be afraid to be honest," said Jenna. "If you're against it, I need to know."

"Well, there's a lot to unpack with that," I began, "but let's start with the fact that if you're seeking my permission, you don't need it. You're an adult, and free to make your own choices. Let me ask you this. Why exactly are you considering it?"

"Well, there's the obvious part," answered Jenna, "I could use the money. I barely make anything at the diner, and it's exhausting juggling shifts after classes all day. I know...someone...who has an Only Fans account, and she makes really great money at it, just for posting sexy pics and little video clips."

I wondered for a moment who exactly it was she was talking about, but seeing as Jenna didn't volunteer a name, I decided not to pry.

"What about your privacy?" I asked. "Do you have concerns about people recognizing you, about possible repercussions from it?"

"I do," said Jenna, "believe me I've considered that. But lots of women on there don't show their face, or their full face. And you can also block people from the area you live in from even seeing your account. So with some care, you can stay pretty anonymous."

"Well, it seems like you've done your homework there, that's good," I said. "Last question, I suppose. How far would you be taking things? Just sexy pics? Full nudes?"

"I...I don't know, exactly," said Jenna. "I was thinking I could start simple and see how it went. Mi...my friend...suggested simple, sexy lingerie pics and partial nudes to start, then let the guys who sign up pay extra if they want...well, more."

Jenna looked at me, her eyes tense. "So...so what do you think? Honestly?"

I thought about the pics Jenna had sent me on Snapchat awhile back, about how cute and sexy they were, about how damn good she was at posing and teasing. I thought about her posting them for other men to see. I thought about them paying her for the privilege of seeing her naked so they could jerk off to her.

And my cock throbbed at the idea.

Jenna spotted the bulge under the sheets and grinned. "Is that my answer?"

I laughed. "I suppose so. Like I said, you don't need my permission, nor my approval. But if you're seeking it, you have it."

Jenna's face lit up. "Thank you. I appreciate that I don't NEED your approval, but it is important to me to have your support."

Jenna's hand went to my thigh, slowly moving its way upwards. "So you like the idea of other men seeing me naked? Getting hard for me like you do?" she purred in my ear.

"I...guess I do," I said, my breathing already getting heavier with anticipation as her hand inched closer to my now fully erect cock.

"I'll have to interact with them online, at least in comments. Flirt with them, tease them, make them wanna tip me. They may wanna send me dick pics. You're okay with that?" Her fingers were now tickling my balls.

I shuddered with pleasure. "You're gonna make a ton of money at it, darlin'. They won't be able to resist you."

Jenna nibbled my earlobe, then whispered in my ear, "They won't get to fuck me, though. They can look, but never touch."

Jenna swung herself up, straddling my lap. I could feel her heat radiating from between her legs, her feminine scent now strong in the air. "This is only for you."

Jenna reached down, guided my tip between her petals, and slid down on me in one smooth motion.

"Wait," I gasped. "What about a condom?"

Jenna, who'd already begun bucking herself on me, paused a moment, considering, then began humping me again. "I'm on the pill," she said, panting softly, "and my period is due in a day or two. I think it's an acceptable risk. I just wanna feel you inside me."

I objected no further, and instead simply enjoyed the incredible feeling of Jenna's slick, warm, sheath sliding along my shaft, completely unobstructed for the first time. Dear God, she was tight.

Our love making was slow and unhurried. We continued talking as she rode me, her arms around my neck, her eyes locked with mine.

"You said you could think of other ways to show me off," said Jenna, her voice low and sultry. "What did you have in mind?"

"There are...adult clubs. Swingers clubs. Some couples go to hook up with other people, some just go to watch. You can...fuck in front of other people. Or watch them fucking." I was struggling to speak as Jenna rocked up and down on me. "You could...walk around in lingerie, or...fully naked...if you wanted. Everyone could...see you, but no one would...touch you...without your permission."

"That...sounds...fucking hot," gasped Jenna, as her hips rocked even faster. "You'd let me...walk around naked...in a room full of strangers?"

"If...if you wanted it, yes," I groaned. "It would be such a turn on. Watching the other men look at you. Admiring you. Wanting you."

"And knowing only you could have me," purred Jenna. "I could...suck your cock, while they all watched. Wishing they were you. You could...cum...all over my little face...mark me as yours...oh, fuck, I love it, oh ffffff!!!"

Jenna's cunt spasmed, gripping me like a vice as she came. But she never stopped riding me, working to draw out my climax as well.

My cock was swelling and straining, close to release but not quite able to cross the threshold. Perhaps because I'd already cum not that long ago.

Jenna sensed my struggle. "You okay?"

"Yeah," I gasped, "just...I'm so close, but it may be...too soon...since last time. Can't...quite...get there."

Jenna took my face in her hands and turned on her innocent little princess voice. "You like that idea, daddy? Of me sucking you off in public? Of you cumming all over your little princess while they watched?"

"Yes, oh fuck yes," I groaned almost painfully.

Jenna jumped up off my lap, leaving my cock slick with her fresh cream, and dropped to her knees beside the bed.

"Get up, daddy," she pleaded. "Get up and cum on your little princess. I need it daddy, please?"

I was on my feet in an instant, my cock inches above her adorable, sweet little pouting lips, and I began to jerk myself madly.

"Yes, that's it, daddy, jerk it for me, cum for me!" Her green eyes met mine, and she turned her face upwards, waiting.

I howled as my cum finally blasted free, splattering across her face and neck, streaming down her chest and into her cleavage.

Jenna's fingers traced her lovely face, smearing my spunk around, smiling. Her eye contact sent shivers through me. Her gaze was somehow intense, warm, caring, lustful and happy all at once. It was the look every man wants from his woman, but very rarely gets.

I pulled Jenna to her feet and kissed her deeply. I could taste my own cum on her lips, but didn't care. When a woman is that hot and passionate about letting you cum on her face, you wouldn't object to it either, I promise you.

We finally fell over together on the bed, once again exhausted and sticky from our exertions. We lay quietly for a while, sharing intimacy as well as body heat.

I felt Jenna moving beside me and lifted my head to find her slowly smearing the rest of my cum around her face and chest.

"Do you want a washcloth?" I asked.

"No, not just yet," she said. "I'll wash my face later, but for now, I'm...enjoying the smell of you on me."

She noted my surprised expression and gave me a bemused smile. "I told you there were a lot of kinky things you didn't know about me yet. And you're not the only one that gets off on the smell of sex, ya know."

"I gotta ask," I said, "do you actually enjoy me cumming on your face, or did you just let me do it because you knew it would get me over the edge?"

"Both," she said, without hesitation. "That first time I let you, in my kitchen, it was mostly because I knew you'd enjoy it. I wanted to shock you a little, give you something hot and sexy to think about after.

"I'd had a dream about you before we reconnected. In the dream, you were masturbating for me again, but this time I was naked and masturbating, too. And I let you cum on my face.

"So I decided to make that dream happen. I did it for you, and for me, and I really wound up enjoying it. I had a little orgasm right then, and had to masturbate in the shower after, I was so turned on."

I chuckled softly. "Yeah, I kinda...heard you. Didn't mean to eavesdrop, but I was putting the clothes in the dryer. I didn't linger, though. I wanted to respect your privacy."

Jenna blushed a little, but laughed. "It's okay. It's not like I tried to be quiet. Anyway, this time, you were enjoying the fantasy we were talking about, but I could tell you were struggling to cum. So I figured that would help, plus I was fantasizing about it too."

"It really did help," I grinned. "Plus, when you do that cute little 'princess' thing..."

Jenna giggled. "You like that, huh? I do, too, sometimes. It's...fun."

"You don't find calling me 'daddy' weird?"

Jenna sat up. "No. Why, do you? I thought you liked it."

"I do," I said, "it's just one of those things that can be a little...I dunno, strange. The incestuous implications."

Jenna frowned at me. "You really do overthink things sometimes. You're not my dad. I don't think of you as my dad. I'm not thinking of my dad when I do it. And I'm not acting like some underage fantasy daughter. It's a bit of kinky role-play, nothing more, okay?"

"Of course, sorry, I wasn't trying to imply any of that, just..." I trailed off, feeling a bit embarrassed.

Jenna's face softened. "Do you enjoy it?" she asked simply.

"Yes."

Jenna kissed my cheek. "Then shut up, stop feeling guilty about your kinks, and let yourself have fun."

I sighed. "Sorry, old habits. My ex always made me feel guilty just for asking for sex, let alone trying to spice things up a little."

"I'm not your ex," said Jenna kindly, "and I'm learning to put my negative past aside and explore my kinks without fear or guilt, too. And I'm looking forward to exploring it with you. But we can't be second guessing ourselves. I don't know if we'll make every fantasy we talk about actually happen, or if we'll even want to. But the things we know we both enjoy, we can embrace them, knowing we're both into it and open about it, okay?"

Djmac1031
Djmac1031
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