The Jenna Arrangement Pt. 16

She was trying to play it cool, but I could tell she was hiding her anger. Which I found odd, considering her admission that she was going to end it anyway. Maybe she just didn't like being dumped first.

Jenna took Michelle's hand. "Well, it still sucks that you had a bad night. If you need an ear, I'm here for you, okay?"

Michelle smiled thinly. "I'm fine. But thank you. I'll be over it by the morning. And free and single all summer. Which is what I wanted anyway."

Jenna nodded and decided to leave it at that.

Trish broke the awkward silence. "I really should get going."

Jenna and I walked her to the door. Trish put her bag down then hugged us both. "Thanks again," she said softly, "I really enjoyed that."

Jenna and I returned her hug and kissed her on her cheeks. "You're very welcome," Jenna whispered. "Hopefully we can do it again sometime."

Trish gave a smile that said she'd like that, then picked up her bag and headed out. "Text me when you get home!" Jenna called after her. Trish turned and waved. "I will!"

I debated on whether I should stay. I wanted to remain with Jenna, of course. But maybe Michelle wanted some privacy.

Michelle answered my question for me. "Are you staying again tonight, Tommy?"

"I was hoping to, but only if it's not an inconvenience," I replied.

"No problem at all," said Michelle. "As long as you two don't keep me up ALL night."

We wound up ordering a pizza, and after eating, we decided to take Michelle up on her offer to discuss Only Fans.

Michelle filled us in on everything. She explained how she fully protected her privacy by blocking any areas around the country and world where she didn't want her account available. She also explained how you could offer a monthly subscription or sell content on an individual basis, or both.

"I post regular nudes and lingerie pics along with short little video clips on my subscription feed," she said, "then offer longer, more explicit videos for sale at higher prices. That's where the real money is."

"Just how...explicit, do you get?" Jenna asked.

"Depends," Michelle shrugged, "in the subscription feed, I tend to go back and forth between teasing partial nudes and full nudity. But on the pay videos I'll do more, of course. Masturbation, usually with various toys, sometimes some role-play stuff or jerk off encouragement clips, you know, play to my audience. I've even shot a couple of videos with Dave, handjobs and blowjobs usually. No full sex."

I was struggling to stay casual and focused as Michelle continued to openly discuss how she'd often shoot several nude or nearly nude clips and photos per day, then post them throughout the week, and how she regularly filmed herself masturbating. The mental images of her flashed through my mind despite my best efforts to chase them away.

Michelle must have seen something in my face, because she broke into a wide smile. "I can send you a link, if Jenna approves. I have this entire state blocked, but I could make a special exception for you, maybe even give you a discount," she winked.

I had no idea if she was serious or simply teasing me, and decided it best not to pursue it for the moment, especially after spotting how uncomfortable Jenna seemed.

So instead I changed gears. "If you don't mind me asking, how much money can you make doing this?"

"Well, it depends," Michelle answered, "it takes awhile to build a following. And you have to do a lot of self promotion. Reddit, Tim Tok, Instagram. Build followings there and lure them in. Then it depends on how much you charge per month for a subscription, how many extras you sell, whether you do Special Requests, and so on. But don't expect to get rich from it right away. Took me several months before I really got things rolling. But right now, I average about three hundred a week."

"Really? I'd actually expected it would be a lot more," said Jenna.

Michelle shrugged. "It could be, maybe, if I put more work into it or sold more hard core content. I hear of some content creators making thousands a week, but most really only average a few hundred a month, so I'm doing pretty well all things considered. Enough to pay my bills and start a little savings account. I doubt I'll do it forever, just to get me through college. Then I'm planning on working for my family's restaurant business."

"Well, it's certainly a lot to think about," Jenna said.

Michelle nodded. "In the end, how far you go with it will be up to you...both of you, I guess. You decide how far you're willing to go, how much you're willing to show. I wouldn't count on getting rich from it, but I'm willing to bet you'll make way more than you ever could busting your ass at that diner."

"Just one last thing to keep in mind," she continued. "Most guys, especially your Only Fans subscribers, will be pretty nice. They're paying for it, obviously, so they'll be respectful in their interactions, although some of them can be a little creepy. But you can always block anyone who gets out of control. It's the guys on the other social media sites you use to promote yourself that you have to worry about. They can get pretty ugly. You'll need a thick skin. You can block them as well, of course, but still, it can get...hurtful. Assholes calling you a whore and a skank and preaching at you about how you have 'no self respect.' Meanwhile they're all probably typing one handed."

I shook my head sadly. "I don't understand men like that. "

"They're a very vocal minority," sighed Michelle. "Most of the guys I chat with are very nice. They wanna chat, they wanna flirt, they wanna feel appreciated. And I give them that. The more you interact with them, the more you'll retain their business. But you have to set limits, of course. Oh, and I hope you don't mind, but just be prepared, because Jenna is gonna get a LOT of dick pics, and a lot of guys wanting to sext with her."

"Jenna and I discussed that a little," I said. "And I'm okay with it, I get it's part of the deal. We both know she's not gonna do anymore than flirt and play. It's not like she'd actually be having sex with any of them. And I can get into the idea of guys looking but being unable to touch."

Michelle smiled. "You seem to be pretty understanding about it all, that will certainly help. Hell, even Dave used to get off on the idea a little. I'd sometimes let him read some of my sext chats or comments. I'm sure plenty of guys couldn't handle that. But as long as you two communicate about it, you'll be fine. Hey, maybe you can even help her create her content; take her pics and videos, maybe even make a few videos together, depending on what you're comfortable with."

"I suppose that's something else we can discuss," said Jenna. "Thanks for talking to us about this, Michelle. It's been very helpful."

"No problem," Michelle said. "And you can always come to me if you have any other questions as you go. Maybe I can even help promote your page on mine when you're ready."

"Speaking of which," she continued, standing with a stretch, "I gotta go sort through some pics and get a post up for tonight, then respond to a few messages and stuff. Again, full warning, it's easy but time consuming, you're gonna be working at it pretty much every day."

Michelle went off to her room, leaving Jenna and I alone in the living room. Jenna looked deep in thought.

"What's on your mind?" I asked.

Jenna sighed. "Just thinking hard about this Only Fans thing. Part of me is very excited by it, but it's also very intimidating. And I still worry about how you'll handle it, with me having to, well, flirt and be sexy with other guys for money. That you'll think less of me for it."

I put my arm around her, comforting her. "Jenna, do you think less of me for what I've done with Trish? Or for looking at your other friends and finding them attractive? For being aroused by them?"

"No, of course not," said Jenna.

"Then why do you think I would hold you to a different standard? And unlike what we've done with Trish, you're not actually looking to do anything physically with these men. I know you enjoy teasing guys and having them get off to you. And I accept that. Hell, how could I not, when it's what brought us together in the first place? Yes, you needed the money, but you also wanted to see if you could get me off like you did with guys on Omegle. This really isn't all that different. You're doing it for money, sure. But that doesn't mean you can't have some fun with it either."

"In fact," I continued, "I think there'd be a really good market for what you like to do. You wouldn't have to do hard core stuff if you didn't want to, but I'm sure there's lots of men like me who'd enjoy interacting with a young woman like you online, letting you tease and titillate them into getting off virtually."

"I suppose you're right," said Jenna. "I just worry you'd start thinking I was a slut."

"God, I hate that fucking word," I grumbled. "And I hate the double standard that makes women ashamed to embrace their sexuality. Look, you're always telling me not to overthink things. If this is something you want and will actually enjoy, then go for it. I'll embrace it wholeheartedly, just as you've done with my little kinks."

"Thank you," said Jenna, "you have no idea how much that means to me. I suppose I'll start slowly and see how it goes. I'll have plenty of time at home this summer to set up the accounts I need and start building a following. Maybe you can even help me with ideas, or give me feedback on what you think is working or isn't."

"I'd be happy to help in any way you'd like," I smiled. "It'll help keep things fun and fresh with us too. I think I'll really enjoy watching all the guys drooling over you, darlin'. It would really get my motor running."

Jenna snuggled into me. "I certainly hope so. Speaking of, think your motor's had enough time to recharge? Thinking about all this has gotten me pretty excited."

"I think there's still some fuel left in the tank," I grinned. Taking her by the hand, I led her to her bedroom.

We made love quietly, trying to keep our promise to Michelle not to disturb her. But as we did, we embraced the fantasy of Jenna sharing herself online.

"You're so beautiful, so sexy," I said softly as Jenna rode me Cowgirl style, "just think how fucking hard and horny you're going to get all those guys; teasing them with your sexy body, arousing them with your dirty talk, encouraging them to get off to you, to cum just for you."

"God I'm getting so wet just thinking about it," Jenna moaned. "I love being a little cock tease, getting them hard, knowing they're hard for me. Asking them to send me pics of their hard cocks, showing me how aroused they are for me. You know I'm gonna want to fuck you a lot, right?"

"Oh, I'm counting on it," I laughed.

Jenna rode me to several orgasms before finally slipping off of me, exhausted. "Would you do me a favor?" she asked as she caught her breath.

"Of course. Anything you want."

Jenna slid off the bed and got on her knees on the floor. "I want to watch you jerk off and finish on me. I love watching you stroke your dick for me."

Without a word, I stood before her. I pulled the condom off of my still throbbing erection and immediately began to masturbate directly over her face. "Is this what you want, princess? To watch me stroke my hard cock for you? To know you get me so fucking turned on that I can't help but touch it, jerk it, make it cum just for you?"

"Yes, daddy," Jenna purred. "Jerk it for me. Show me how much you love me."

It struck me then just how much I truly did love her. Not just because she was currently naked, on her knees before me, begging me to jerk off on her. But because of how open, accepting, and giving she was.

I thought back to our first meeting; just two strangers exploring their own fantasies. And now here we were, lovers who'd freely embraced each other's kinks.

That first time I could only fantasize about fucking her, or even just seeing her naked. We'd gone so much further since then, further than I'd dared even dream when I got her first email reply to my ad.

And here we were, bringing it back around to our basic desires: my enjoyment of being watched, her enjoyment of watching.

So I jerked off for her as she knelt before me, her emerald eyes gazing up expectantly as her hand explored the folds of her womanhood, delighting in the simple pleasure of masturbating together.

"Cum for me, daddy. Don't hold it back. I love making you cum, love the feel of it on my skin. When you cum on me, it's gonna make me cum, too. I want you to know that. I want you to cum knowing how fucking hot it's gonna make me, how I'm gonna gush from it. All because of you, my love. Now, do it. Give it to me."

From any other woman, those words would have sounded like lines from a cheesy porn script. But not from Jenna. Her voice was pure seduction. I knew, and felt, that she meant every word, not just saying what she thought I'd like to hear to feed my ego. She was genuinely enjoying this, and I believed her when she said my cumming on her would push her over the edge of pleasure.

And that knowledge made it impossible to deny her. Why would I want to?

Jenna's face flushed a bright red as my first spurts of cum landed on her cheeks and nose, the next blast splashing across her parted lips, her tongue already lapping at it between her squeals of delight as she rocked on her knees, her body trembling in orgasmic bliss.

I ran my fingers across her face, scooping up my cum and guiding it to her mouth. The look in her eyes as she eagerly slurped it off my fingers sent such a thrill of excitement through me that, despite it's slow deflation, my cock managed to squeeze out yet another dollop of spunk.

Jenna eyed it hungrily and in a flash, licked it from my sensitive tip. "Fuck," I gasped, "do you have any idea how fucking hot that was?"

Jenna smiled playfully. "I guess I really am becoming a little cum slut," she giggled as she stood. Then, giving me a sticky kiss, "but only for you, daddy."

We held each other quietly for a few moments, then collapsed on the bed. For a while we simply lay there; me smelling Jenna's scent on my fingers, her lazily smearing the drops of cum that had splattered on her chest around, rubbing it into her skin.

"Let me go get you something to clean up with," I offered.

Jenna smiled, "No, it's okay. This is our last night together for awhile. I want to sleep with your scent all over me."

She looked a little sad. "I'm really going to miss this. Miss you."

I wrapped her in my arms. "I'll miss you, too. But we'll get through it."

Jenna broke my embrace after a few moments and sat up, looking down at me. "So what are you going to do all summer while I'm gone?"

I shrugged. "Dunno. Same thing I always do, I guess. Work, go to the gym. Eat, sleep. Video chat with you every night."

"I want you to go out and have some fun," she said firmly. "I don't want you sitting home every weekend. Find yourself something to do, okay?"

"I'll try," I smiled.

"You could spend time with Trish if you wanted," Jenna offered.

"What do you mean? I thought she was going home, too."

"Oh, she is," Jenna explained, "but her parents' place isn't far from here at all. So if you two wanted to hang out together, keep each other company, I wouldn't mind."

"Jenna, I wouldn't want to, well...DO things with Trish unless you were involved." I said.

Jenna laughed. "I didn't mean THOSE kinds of things. I meant go to a movie, or spend a day at the lake again or something."

"Although," she continued, "if you two decided you wanted to...take things further, I'd be okay with that, too."

That caught me by surprise. "Jenna, I thought we agreed that anything we did with Trish, we'd share together."

"We did," Jenna agreed, "but I've been thinking about it, about her. Maybe a threesome is too intimidating for her first time. Maybe she'd be more comfortable if it was just you and her."

"I don't know, Jenna. That's assuming she wants her first time to be with me; she may not even really want that. But would it make her any more comfortable sleeping with her best friend's man while you're not around?"

"Well, maybe I could watch," Jenna smiled suggestively.

I shook my head, laughing softly. "God, every time I think you can't surprise me anymore, you do it again. But again, you're assuming Trish would actually want this. Plus there's the added pressure of me being her first."

"Do you care about her?" Jenna asked.

"You know I do."

"Then I can't think of a better man to give her her first full sexual experience. I know you'd treat her just as well, as caring, as you treated me our first time."

"Of course I would, but..." I paused, not knowing what else to say. I'd never thought I'd find myself in a position where I'd be discussing the possibility of taking the virginity of my girlfriend's best friend.

Jenna smiled again. "Look, I'm not saying you HAVE to do it. I'm simply giving you permission if it happens. And I'll tell Trish the same thing. If it's something she decides she wants, and you want it as well, I want you to understand I have no reservations about it. It would make me happy. And I need you to understand and believe that, okay?"

I sighed and smiled. "Okay. I believe you. And maybe I will make some plans to see Trish this summer if she wants. But I'm not going to actively pursue her sexually. I don't want to pressure her, and neither should you."

"Of course not," Jenna agreed. "We'll leave it up to her."

***

The next morning was a flurry of activity. I went and picked up some breakfast and coffee while Jenna and Michelle started the final clean out of the dorm apartment.

Trish was already there when I got back, sitting at the kitchen table, talking with Jenna. They both gave me a mischievous smile as I approached them, putting the food down. "Sorry, am I interrupting something?"

"Not really," said Jenna. "We were just discussing a little...arrangement for the summer."

From the blush on Trish's face, my guess was their "arrangement" had something to do with the conversation Jenna and I had last night about my spending time with Trish this summer while Jenna was away. Michelle came in just then to join us for breakfast, so I didn't pursue it further.

After eating I pitched in to help the ladies with the last of the cleaning and packing.

I loaded up my car with the boxes Jenna had asked me to store for her, then helped pile her remaining few boxes and cases by the front door.

Michelle, who had the longest trip ahead, had a delivery service come pick up her boxes, then shortly after, an Uber arrived to take her to the airport.

After some hugs and tearful goodbyes with Jenna and Trish, she turned to me. "Guess I won't see you again til fall, but I have your number; I'll text you a few links if you're interested in 'seeing' me," she winked.

I wasn't quite sure what she meant, but I had a suspicion it had to do with her Only Fans page. I'd have to talk to Jenna about that later, as I wasn't really sure how comfortable she'd be with the idea of me viewing Michelle's nude pictures and videos.

Jenna stood beside me and sighed as we watched Michelle's ride pull away. "I guess this is it. My mom just texted, she'll be here in about twenty minutes."

"I should probably get going then," I said reluctantly. It felt silly and slightly infuriating to have to hide from her mother, but I also fully understood the utter awkwardness of the situation.

Jenna threw her arms around me and began to cry. "I'm really going to miss you."

"I know," I said, trying to comfort her as best I could.

Trish stood off to the side, looking rather forlorn herself. Jenna and I waved her in and she joined us in a group hug. "We'll all stay in touch, right?"