The Jenna Arrangement

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

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Tom awoke to the sound of rain on his bedroom window and the smell of frying bacon and fresh coffee wafting in from the kitchen.

His two young companions had, as usual, woken up before him. Checking the clock, it was just before noon.

He got out of bed with a stretch and a yawn. Looking down, he realized he was still naked from the night before.

He smiled at the memory of Jenna and Trish sharing his cock as they gave him the first double blowjob of his life. His cock, already in Morning Wood mode, gave a little twitch at the recollection.

Bending, he reached for the gym shorts he usually bummed around the house in, then paused.

"Do I have to get dressed?" he thought. Last night the ladies had made it pretty clear they were more than comfortable with casual nudity; they'd both stripped off their clothing and dumped them on the living room floor after getting home from the concert, and later had playfully chided him for keeping his boxers on.

Dropping the shorts, he decided to test things out. He saw no reason why either would object to him staying naked.

"Guess I'll find out," he chuckled to himself. "But first, I gotta pee."

After using the bathroom, and giving himself a quick wipe down with a warm washcloth after discovering some sticky leftovers from last night's orgasm, he walked casually into the kitchen, completely nude.

"Good morning, ladies," he said nonchalantly as he strolled past them to the counter to pour himself a cup of coffee from the fresh pot the girls had made.

Trish was at the stove. Looking over her shoulder, she grinned widely when she saw him. "Good morning indeed!"

Jenna was at the kitchen table, looking at her phone. She too turned around as he passed behind her, eyes bulging in surprise and a look of merriment on her face. "Good morning," she managed, barely containing her sudden giggle fit.

"Good morning, Tommy," Michelle's voice came from the phone. "You look...well."

Tom froze in his tracks. "Oh, shit."

All three girls burst out in laughter. He turned slowly to see Jenna, still sitting in her chair, still holding her phone up. Michelle was on the screen, waving at him. "Slept late, huh? Did Jenna and Trish keep you...UP, all night?"

Tom blushed furiously and moved to try and get himself off camera. "Hey Michelle, so sorry! Didn't know you were on video chat."

"Sure you didn't," she winked, still giggling. "Always going out of your way to flash me, aren't you?"

"I'm...gonna go get dressed now," he replied sheepishly.

"Oh, don't bother on my account," smirked Michelle. "We were just finishing up anyway."

Tom caught Jenna's eye to gauge her reaction. All he saw was sheer amusement at the situation he'd inadvertently put himself in.

With a shrug and still slightly embarrassed smile, he turned and went back to fixing his coffee, now very conscious of the fact that Michelle might still be looking at his ass.

"So anyway," Michelle said, returning to her conversation with Jenna, "look them over and feel free to steal any ideas for yourself. We all 'borrow' each other's material anyway. I can give you any pointers on making them too, if you need."

"Thanks Michelle, I'll definitely do that and be in touch again soon," said Jenna.

"You can share them with Tommy, too, if you want. I don't mind," said Michelle.

"Share what?" Tom asked, now intrigued as to what exactly it was they were talking about.

"Michelle gave me access to her Only Fans page," explained Jenna. "I was looking for some inspiration for content on mine so she suggested checking out hers."

Tom thought back to a conversation they'd had the weekend school ended when Michelle had teased sending him a link to her Only Fans content, but she never had.

He was actually relieved about it, only because he wasn't sure how Jenna would feel about the idea of him checking out nude photos and videos of her friend and roommate.

He was very curious now if Jenna would indeed deem to share it with him at some point, or choose not to include him when she went through it for ideas. He'd leave it up to her, he supposed. While he'd be more than happy to see Michelle naked, he didn't want to if there was any indication that it would make Jenna uncomfortable.

Tom tried to sound casual in his reply. "Well I'm sure that'll be a big help for you."

"Okay, I gotta run," Michelle chirped. "Love you, Jenna! Love you, Trish! Tommy, it was nice...seeing you! Bye!"

Jenna put down her phone with a smirk. "Sorry, darlin'," Tom shrugged. "I honestly had no clue."

"It's fine," said Jenna. "Sit, eat."

Trish joined them, bringing a plate of fresh bacon and eggs.

After the embarrassment of walking in on the video call, Tom was feeling much more self conscious about his nudity, but it faded quickly as they dug into their late breakfast. Neither Jenna nor Trish so much as mentioned it again, nor seemed the least bit phased by it.

The girls were still dressed in the outfits they'd slept in last night, and while nothing spectacularly revealing, both still looked adorably sexy. Even with their hair a "bed head" mess.

They also looked slightly bummed. "Well, there goes our plans to go to the lake today," Trish sighed as a thunder clap boomed outside. The rain was coming down light but steady.

"Dammit. Bought those new bathing suits for nothing," grumbled Jenna.

"I've got an idea," Tom offered. "My gym has an indoor pool. We could go hang out there for the afternoon."

"Really?" they chimed.

"Sure," he shrugged. "I'm allowed one guest for sure, but I think for a small extra fee I can bring two."

"That sounds great!" Jenna beamed. "How soon can we go?"

"As soon as you're ready," he said.

The girls jumped up excitedly, each giving him a hug before racing off to the bedroom to change.

While each hug had been brief, their warm bodies so close against him reminded him again of his nudity and how exciting it had been to have spent breakfast so casually naked around two beautiful young women.

Tom slightly regretted making the offer to go out now, only because it meant he finally had to get dressed. But he also knew there'd be plenty of opportunities for them to play together and, after last night, knew Trish was becoming more and more comfortable with her role in the relationship between the three of them and that things could very well escalate even more in the near future.

So he would be patient, as he'd always been. It had served him well so far.

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Jenna and Trish sat poolside, their legs dangling in the water.

They had joined Tom in working out for a while before leaving him to hit the pool. While it was nice, it wasn't like the lake, where they would have been able to soak up the sun and fresh air. Still, they had fun swimming, and while their new swimsuits were relatively modest, they enjoyed the attention of the men around them desperately trying to look without being obvious about it.

Jenna had become much more comfortable in her body over the past several months. Trish, however, was still feeling somewhat insecure. Reaching down, she pinched at her rounded belly. "I really do need to lose some weight," she sighed. "I'm getting fat."

"Oh, stop it," Jenna snapped, not unkindly. "A few extra pounds is not FAT. I think you're beautiful just the way you are, and so does Tommy."

Trish gave a half smile. "Thanks."

"You know, this isn't all that far from campus," Jenna remarked. "Maybe we should look into getting a membership ourselves. We could come after classes and on the weekends."

"That would be fun," said Trish. "I wouldn't mind getting a little exercise."

"Plus there's a lot of cute guys here," Jenna offered suggestively.

"Yeah, I suppose," Trish sighed, not sounding convinced.

Jenna sensed her disillusionment but decided to let it go for the moment. Instead she changed the subject. "Hey, would you do me a favor? Could you take a few pics of me in this suit? I wanna put them up on Insta."

"Sure," Trish shrugged.

Jenna handed Trish her phone and they spent the next few minutes taking photos; Jenna smiling and striking poses while Trish clicked away. Jenna could feel the eyes of the men in the area watching but mostly tuned them out.

When they finished they sat back down at the edge of the pool, Jenna scrolling through her photos and posting the best of them to Instagram.

"These came out great, thanks," she said. Suddenly feeling mischievous, she glanced around the pool.

While there were several men milling around, both in and out of the water, none were looking in her direction, at least not directly.

Opening her camera, she pointed it down at her lap and, after another quick look around, lifted the seam of her bottoms to reveal her recently trimmed red bush. She snapped a quick few pictures then returned her suit to normal.

Trish was the only one close enough to see it. "Feeling a little risqué, eh?" she smirked.

"Just need some Only Fans material," Jenna grinned. "Would you help me take a few more?"

"What'd you have in mind?" asked Trish, curious.

Jenna leaned in and explained softly. Trish's face twisted in a wry smirk as she slipped into the waist deep water, careful to keep Jenna's phone high and dry as she stood in front of her, blocking the view of the two men having their own conversation on the other side of the pool.

Both the ladies looked around again to make sure no one was directly paying attention to them. When they were sure the coast was clear, Trish quickly aimed the phone at Jenna. "Okay, make it quick," she whispered.

Jenna reached down and pulled her bottoms aside, exposing her fiery pubes and pink slit.

Trish snapped several quick pics before Jenna readjusted her suit. After another quick glance around, Jenna pulled her top aside, exposing first her left nipple, then her right as Trish again took photos.

"Here, let me see," Jenna giggled, reaching for her phone. "Perfect. Just revealing enough. Gonna post them right now!"

Trish pulled herself back up out of the water and again sat beside Jenna as she posted her pictures to Only Fans. "How's it been going so far?" Trish asked, "been making any money?"

"It's doing okay," Jenna answered. "I've gotten several more subscribers since Michelle helped promote my page, and a few tips here and there. Not making enough to live off of just yet, but I've only just started really."

"And Tommy's been okay with it?" Trish asked.

"Oh yeah, he's been great about it. Even helped me take some pictures, too!" Jenna showed her the pictures they'd taken that night at the rest stop on their way back from their meeting with their lawyer.

Trish's eyebrows arched in surprise. "Wow! Look at you, getting all daring and stuff!"

Jenna laughed. "Hey, public content gets a good response, gotta give'em what they want, right?"

"Speaking of daring," Trish continued, her face becoming pensive, "is that offer to, you know...be with Tommy...still available? Because I've been thinking about it a lot and I've decided I...I want to."

"Really?" Jenna beamed. "Of course it's still available! What made you decide that you want to?"

Trish sighed. "Lots of reasons, really. Some of it I'd rather wait to talk about til we get home, when I can tell both of you."

Jenna took her hand. "Well as long as you're comfortable, I'm happy for you. And excited! I know Tommy will make it a truly memorable experience for you."

Trish looked at her friend quizzically. "How can you be so open about sharing your boyfriend with another woman? I'm not complaining, mind you. But I need to understand how you're so sure about it."

Jenna thought for a moment. "I honestly don't have a simple answer. If you'd have asked me several months ago, before I met Tommy, if I'd be into the idea, I'd have laughed."

Jenna gripped Trish's hand tighter. "Maybe I'm just starting to see love, and sex, in a different way. A way that's not exactly traditional. And I think you can love more than one person, and be open to sharing that love."

"Really? That's...great to hear," said Trish. She debated on how much more she wanted to say, but was saved from having to decide when Tom finally showed up, joining them. "Having fun, ladies?"

"In more ways than one," Jenna winked.

"Oh, really?"

Jenna showed Tom the pictures she'd just posted, to his obvious delight. "Wow! Can't leave you two alone for a minute without you getting up to mischief," he laughed.

"Well there's more mischief to be had when we get home," Jenna purred, giving him a sultry look.

"Hey, I'm ready to go wherever you two are," grinned Tom.

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The rain had stopped by the time they got home. After showering and a meal, Trish invited Tom and Jenna to sit with her in the living room.

"So I've been wanting to talk to both of you for a while now," she started, "and I already talked to Jenna a little about this. But I've decided I'd really be open to the idea of continuing this further with our...physical relationship."

"Really? What brought this on?" Tom asked, echoing Jenna's earlier question.

"Well I guess I should start by telling you guys that I was dating someone the past couple of weeks." Noting their surprise. Trish quickly corrected herself. "Well, not really DATING. I only saw him a couple of times."

"He was this guy I knew back in high school, Kenny McKnight. His parents know my parents, that kinda thing. I always thought he was cute but he was dating Gina Greentree through most of high school and he barely knew I existed.

"Anyway, my parents had a party a few weeks ago and he showed up with his parents. We spent most of the night hanging out and talking since we were pretty much the only two people there our age. He's home from college as well, single now, and...by the end of the night we were making out a little. Nothing crazy, but it was...nice."

Trish paused, sighing a bit before continuing. "We arranged to get together again the next weekend, go out to dinner, just us. See if it clicked, ya know?

"The first red flag was how he treated the staff there; he got visibly upset when the wait for our table took longer than they originally told us. Then he made a point of stressing separate checks when our waiter took our order. Not that I expected him to pay for everything, but it's just the way he did it. He actually said 'you're probably going to order more than me so it's only fair.' Like I was gonna order the whole menu or something.

"Then he called our server a fag after he walked away, and when I called him out on it, he blew it off, said he was just 'joking.'

"I don't know why I stayed; I guess I didn't wanna make a scene and we'd already ordered the food. But the conversation went downhill from there. He started going on and on about politics, and we didn't agree on anything.

"By the time we'd finished eating, I couldn't wait to get out of there. So when the waiter asked if we wanted dessert, Kenny acted all surprised when I declined. 'You sure? You seem like a girl who likes her desserts.' I couldn't believe it. Fucking asshole. Again he tries to play it off as a joke, gets mad at ME for being 'so uptight.'"

Trish's eyes were watery as she finished her story. "So anyway, obviously it didn't work out. And it left me in a bit of a funk. But it also left me thinking about, and missing, the two of you."

Tom sighed. "I'm really sorry that guy was such an asshole. You don't deserve that. And I really hope someday you find someone who treats you the way you deserve."

Wiping her eyes, Trish looked up at her friends and smiled. "Thank you. But in a way, I feel I already have. This experience made me realize how much I care about both of you. And how much I enjoy sharing in the relationship you two have, in all the ways you've included me, not just sexually but...everything. I don't know if I'm explaining this right, it's very confusing, but..."

Jenna broke in, "I think I get it. You feel like you're part of something special with us. And I'm glad you feel that way, Trish. Because you are. I'm pretty sure Tommy would agree, we're both really happy to have you be a part of our relationship."

Tom nodded. "Absolutely. All the sex stuff aside, I'm really glad you and Jenna are such good friends. And I'm glad we're friends, too, Trish."

Trish smiled nervously. "That's just it, though. I'm beginning to think of you, BOTH of you, as more than just 'friends.'

"Don't get me wrong; I'm not looking to steal either of you away from each other. But...oh, fuck it. I'm just gonna say it. I love you. Both of you."

Silence hung in the air for a few moments. Then Jenna threw her arms around her friend. "I love you too, Trish. You know I do."

Tom sat silent, stunned by the revelation and trying to work out what exactly it all meant. Finally he found his voice. "Trish, you know I care about you, very much. We've talked before about different types of 'love,' and how there are various layers to it all. I guess my question is, when you say 'love,' are you looking for more than just the friendship we have, or...?"

Trish let out a soft laugh. "I honestly don't know. This is all very new to me. I just know I wanna be...closer...to both of you, in, well, whatever ways you'll let me."

Jenna smiled, hugging Trish even closer. "I think I understand. I told you earlier I didn't mind sharing you. And it's not just sexually. I like that he makes you as happy as he makes me."

Jenna turned to Tom. "I can already tell you're over thinking all of this, so I'm just gonna make it clear. Don't. Don't worry about saying the wrong thing, or how you think it might upset me. Just be honest, be real. Tell us what you're thinking. What you're feeling."

Tom swallowed hard, trying to find his voice. Finally it came back to him. "I guess I'm just trying to understand what we're talking about here. Jenna. You know I love you. And Trish, I suppose I love you too, although in a different way. I've been careful to keep our boundaries within our friendship, but if we're talking about expanding that, I..."

He paused, the girls sitting silent, letting him collect his thoughts. "I've...not had the best of luck when it comes to relationships," he finally continued, "and I've been told I'm...closed off, emotionally."

"That's bullshit," Jenna interjected. "You've been very open with me."

Tom shrugged. "I've grown over the years, I suppose; learned from my mistakes. And I've started to forgive myself for my failures, and also understand they weren't entirely my fault. But..."

Again he paused, looking at them. "I love both of you, I truly do. But it's hard enough being in a relationship with one person. I have no idea how to go about it with two at the same time. I'm afraid I'll screw it up, make one of you feel jealous, or lesser somehow, or..."

"Let me stop you there," Trish cut in. "I'm not looking for a 'traditional relationship' from this, nor am I expecting equal partnership with Jenna. I love and respect you both enough not to try and interfere with that. I just wanted to make it clear before we take any of this any further that I see it as a little bit more than Friends With Benefits, too."

The room fell quiet again as everyone took a collective breath to process everything.

It was Jenna who spoke next. "Look, I don't think we have to put an exact label on things right now, do we? We all love each other, care about each other, and as long as we're all open and honest about our feelings we'll be okay. We can just accept it for what it is right now and see where it takes us, right?"

Tom and Trish nodded in agreement. "I'll do my best," said Tom, "just promise me, both of you, that if I screw something up, or hurt one or both of you somehow, that you'll let me know right away. I don't want either of you to feel neglected or left out, and if you do, just tell me, okay? Otherwise this will never work."