The Jenna Arrangement Pt. 27

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

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"Hey darlin', how are you feeling?"

Jenna smiled up at Tom from the bed. "Oh, hey! Didn't hear you come in. I'm feeling better, thanks. How was your day?"

"Oh, you know. The usual indentured servitude." Tom moved from the doorway to the bed. With an exhausted sigh, he plopped down beside her. "What'cha been up to?"

"Not much. Been responding to some messages on Only Fans, although it's been really tough to be 'flirty' today; my cramps have made it hard to feel sexy."

"Hey, you're always sexy to me," he grinned, kissing her cheek.

"Even when I've been a bum, lounging on the bed all day in sweatpants with a heating pad?"

"Oh, especially then."

"Liar."

They lay together, snuggled close. "I'm gonna miss this when I go back to school next week," Jenna sighed.

"We'll still see each other every weekend," Tom assured her, "and it's not like you'll be a million miles away. I know you'll be busy, but if we plan ahead, we can make time during the week, too. Even if it's just dinner or a movie or something. And of course we can Skype anytime."

"I know," said Jenna, "but still; it's been... really nice, staying here with you."

Tired as he was, Tom felt his pulse quicken as Jenna kissed him, but reigned in his passion. The first few days of Jenna's period were always hard on her, and he knew she wouldn't be up for much more than some cuddling for the time being.

"Think I'll take a shower."

After his shower, he made them a simple dinner. Later, they settled in to watch some TV. They decided on a show they'd both heard good things about, The Queen's Gambit.

"She looks a little bit like you," Tom told Jenna, referring to the main character.

Jenna blushed. "Oh,stop. She's so much prettier than me. Her eyes are amazing."

"Not as amazing as yours. And she's obviously not a real redhead. Yours is much more natural. Have I ever told you how much I love it?"

"Several times," Jenna smiled. "But thank you. I always hated it when I was a kid. It was curlier then; didn't straighten out more til my teens. Everyone picked on me for it. Called me 'Little Orphan Annie.' But I'm happy with it now. Although I have often wondered what I'd look like as a blonde."

"I'd never ask you to change your hair color.I love it, and you, just the way you are. But if you ever decided to dye it, I'd certainly be curious to see how it came out."

"Maybe one day, we'll see."

By 9pm, Jenna was yawning. "I'm sorry, but my cramps are killing me tonight. I think I'm just gonna take some Midol and go to bed."

"Do you mind if I watch another episode?" Tom asked. "Or do you want me to wait for you?"

"Nah, it's fine. I'll catch up tomorrow while you're at work."

After a goodnight kiss, Jenna went off to the bedroom, closing the door behind her.

Tom continued to watch TV. About thirty minutes into the next episode, his phone chirped with a text message alert.

"Who could be texting me this late?" he wondered.

To his surprise, the message was from Michelle.

"Hey, Tommy! Long time no see. I just wanted to finally send you the link to my Only Fans. I know I promised I'd send it ages ago. Sorry I forgot. Link attached. Once you log in, message me there and I can approve your access. Hope you enjoy it! 😉 💋"

Tom was stunned. He remembered the conversation they'd had about it just before she left college for the summer break, but had long since figured she'd just been teasing him since she'd never actually sent it.

He contemplated what he should do. He knew Jenna already had access to Michelle's account and had been using it as inspiration to create her own content.

What he didn't know was how Jenna would feel about HIM viewing it. She'd never volunteered to show him any of it, and he'd never asked.

Michelle was her friend and roommate. Would it upset Jenna for him to accept Michelle's offer to view her nude pictures and videos?

Jenna hadn't minded at all when he'd been naked in front of Michelle and her other friends at the birthday party, and had even encouraged some flirtatious contact between him and the other young ladies there, including Michelle, who'd at one point given his stiff cock a quick, firm stroke.

And of course Michelle, while not naked, had been walking around the entire evening in nothing but some very sheer, sexy lingerie.

If Jenna had no problem with that, why would she take issue with him looking at her online content?

He thought about asking her first. But Jenna was probably already asleep. He could wait until morning of course, talk to her about it then.

But it had been a few days now since they'd last had sex, and Trish was spending the last week before school started with her parents, although she'd promised to come over again on the weekend.

Since Jenna had moved in, he really hadn't needed to masturbate often. Even during the times Jenna was on her period, she'd often taken care of him in other ways.

Still, he hadn't cum in a few days, and he couldn't deny the prospect of seeing Michelle fully nude appealed to him.

Eventually, his lust won out over his reservations.

He texted Michelle back. "Great to hear from you. Hope your summer has been great. Thanks for the link. I'll log in now and message you there."

He'd already had an account set up to view Jenna's content. So Michelle's link took him directly to her account.

After another quick message to Michelle, the subscription status changed, and within moments he had access.

He quickly scanned her profile intro:

"Hey guys! I'm Michelle! I'm a 21 year old college student of Filipino descent. I've got long, dark hair, big, full, natural breasts, and an ass you could bounce a quarter off of.

"I absolutely LOVE sex, and I'm not shy about it! So go ahead, tell me all your kinkiest desires. I'll make them cum true. 😉 🍆💦

"Check my menu for prices on custom requests and remember: take good care of me, and I'll take good care of you."

Beneath her intro was a picture; Michelle, posed in front of what appeared to be the windows of a building, a cityscape he couldn't identify reflected in the glass behind her.

Surprisingly, she was fully clothed. Her hair flowed past her shoulders, blown slightly by a breeze.

Her pink belly shirt conformed to the luscious curves of her breasts, while her tight black yoga pants hugged every inch of her wide hips and long, toned legs.

Scrolling, he next found a series of still photos. Tom recognized the pink lingerie outfit as the same one Michelle had worn the night of Jenna's birthday party.

Unlike that evening, though, he was now privy to much more than a few quick glimpses of her more intimate areas.

Each picture was more revealing, more tantalizing than the previous.

Breasts half exposed, then fully revealed.

Panties, snug and tight over feminine curves and folds before being first pulled aside, then off to expose her full glory.

"Jesus." His cock already swelling in his sweatpants, he freed it with a quick tug. It sprung loose gratefully and within moments expanded to its full length.

He considered getting the lube, but it was in the bedroom, and he didn't want to disturb Jenna.

So instead he spit on his palm and began to stroke as he browsed more of Michelle's content.

He alternated between short video clips and the still photos, lingering over one set in particular that featured a close up shot of her wearing only a black G-string that looked a lot like the one he'd spotted in her laundry basket the night of the party.

He'd resisted the temptation to smell them that night, caked as they were in her cream. But he could not now help but stare at the large wet spot on the panties that barely covered her dark vulva and thick labia and wonder if it was the same pair.

Scrolling further, he was delighted to find a video clip of her in the same G-string, rubbing herself over it as she moaned. Tom watched in delight as her juices gushed, the wet spot slowly spreading and glistening.

Unfortunately, that clip was short. After watching it on repeat a few times, he decided to look for something longer.

He scrolled through several, trying to decide what to watch next before finding one with the intriguing title of: "JOI - Show Me Yours, I'll Show You Mine."

He clicked on it eagerly.

The video opened to a shot of Michelle laying on her bed. She wore a blue and white striped body dress with a low, swooping neckline that displayed plenty of her ample cleavage, with a hemline that ended just below her hips.

She smiled at the camera. "I wanna play a game with you..."

Tom paused the video. He wanted to be able to turn the volume up, but was afraid Jenna might hear it.

Quickly, he rummaged through the drawer of his end table and found his headphones. After connecting them, he shucked his pants off completely and settled back on the couch.

He started the video over.

"I wanna play a game with you. Don't worry, you'll like this game, I promise. It's called You Show Me Yours, I'll Show You Mine.

"It's real simple: take your cock out, do everything I say, and if you're a Good Boy, I'll show you what's under this dress."

Tom was already naked from the waist down of course, but played along in his imagination.

Michelle was still talking in the video. "Oh, my! So excited for me already! Now, don't touch it just yet. Not until I tell you to."

Tom reluctantly let go. His cock twitched in protest.

With a sexy smile, Michelle tugged at the shoulder straps to her dress. Her breasts slipped free, quickly covered by her hands. She juggled them playfully, then squeezed them together tightly. "Okay, you can start jerking. Slowly. Imagine your hard cock sliding between these luscious firm tits."

Tom began to stroke, matching her movements as she bounced her breasts up and down. As much as he loved Jenna's petite breasts, they weren't quite big enough for a good tit-job.

Trish's were. Tom made a mental note to see if she'd be up for it when she joined them again this weekend.

He continued to stroke himself in time to Michelle's coaching and movements, but froze as a shadow moved across the floor.

Looking up, he saw Jenna, standing at the hall entry to the living room.

"Enjoying yourself, cowboy?"

Startled, Tom dropped his phone. His face flushed a deep red as he pulled off the headphones. "Shit! Sorry! I was just... just..."

Jenna's grin widened, her eyes twinkling with mirth. "Oh, it's obvious what you were doing. No need to explain. But you coulda asked, ya know. I might have helped you out."

"I'm sorry, darlin'. You weren't feeling well; didn't wanna bother you. Thought you just wanted to rest."

Jenna shrugged. "I am feeling rather icky. But I couldn't sleep. Came out here to see if you wanted to come snuggle. But apparently you have other things on your mind."

Tom shrugged sheepishly, his tongue firmly tied at the moment.

Jenna moved to sit beside him. "Watching anything interesting?"

Before he could react, she reached out and picked up his phone.

On the screen, the video was still playing, Michelle's dress now hiked up to expose an almost microscopic white thong.

Tom froze, tense, awaiting her reaction.

Jenna's eyes went wide with surprise.

Then she smiled. "Ah, she finally got around to sending you that link, eh?"

"Um, yeah." Tom somehow found his voice. "Just... just tonight in fact. I was gonna tell you, but I thought you were sleeping. You... you don't mind, do you?"

Jenna looked at him and laughed. "Mind? Why would I mind? I was the one that reminded her to send it to you."

Tom's jaw dropped. "Really?"

"Of course. Figured you'd need something to watch since I won't be around as often."

Tom had to chuckle. "And you didn't think I'd just be satisfied watching your content?"

"Oh, come on. Every man needs a little variety now and then. Wouldn't want you getting bored with me now, would I?"

"Bored with you? Never."

Jenna leaned in and kissed him. "You're sweet. I think I'll keep you. Now, finish up what you were doing so we can go to bed."

"You're gonna stay?"

"Unless you'd rather be alone with my roomie," Jenna winked.

"No," Tom grinned. "Please, stay. You know I like it when you watch."

"Do you? I had NO idea," Jenna rolled her eyes sarcastically.

Moving closer, Jenna held the phone so they both could see, leaving Tom's hands free to take care of business.

On screen, Michelle was now silently rubbing herself over the thong.

"Disconnect the headphones," said Jenna, "I wanna hear, too."

"What? Oh, right. Sure."

Michelle's moans now came through the phone speakers. "Oh, yes, baby! Jerk it, just like that! Stroke that big cock for me."

Jenna smirked. "Better do as she says, cowboy. You're falling behind."

Tom took a moment to meet her bright green eyes, and appreciate both the humor and love he found there.

Taking his cock in hand, he quickly brought it back to full erection.

It felt a little strange at first, watching Jenna's friend and roommate masturbating while Jenna sat right beside him.

But he couldn't deny it was also incredibly arousing.

Jenna rested her head on his shoulder, watching both him and the video.

Her voice was soft and sultry in his ear. "She's pretty hot, huh? Look how wet she is. She certainly doesn't fake it, does she? Bet you'd just love to smell her, taste her, wouldn't you?"

Tom was already panting heavily. "Oh, fuck yes!"

"Do you wanna fuck her?"

Tom hesitated only a moment before replying. Earlier in their relationship, he would have felt uncomfortable admitting such a thing to her. But he knew her well enough now, trusted her, and understood her trust in him.

Jenna would never goad him, push him into saying something as a test. This was a fantasy, her way of having fun, of getting him excited, nothing more.

"God yes I wanna fuck her! I'd fuck her so hard, so good."

"I know you would," Jenna purred. "I wanna fuck her too. She looks so delicious. I just wanna eat her up."

Vivid images of Jenna prone between Michelle's wide open legs flashed through his mind. Jenna's tongue, dancing over Michelle's swollen clit as her cries grew louder and her orgasm approached.

It wasn't just his imagination.

In the video, Michelle was indeed getting louder. "Oh, fuck! So close, so close! Cum with me, baby! Shoot that hot load for me! Oh, yes, yes, yesssss!"

"You heard the lady," Jenna intoned. "Cum for her."

Tom rocked back on the couch, almost howling as his climax hit.

Hot spunk sprayed in random directions, several drops hitting the screen. A single drop ran down directly between Michelle's splayed legs.

Tom continued to tremble as he squeezed out the last few spurts, finally letting go of his messy cock with a satisfied sigh.

"Oh, Good Boy." Michelle was now sitting up on her bed, smiling into the camera. "Hope you enjoyed yourself, sweetie. I know I did."

With a wink and a wave, the screen went black.

"Good boy, indeed." Jenna kissed his cheek. "Such a mess, though. Wait here, I'll get you something to clean up."

Jenna returned from the bathroom with a warm washcloth and, to his surprise, knelt before him to clean him up. She took her time, caressing his still semi erect cock and sticky balls.

Despite having just cum, Tom felt himself swell at her touch.

Jenna felt it too. "You really are worked up, aren't you? Think you can save it for me? I really do need to get some sleep."

"Of course, darlin'."

Standing, Tom helped her up from the floor. She slipped naturally into his arms and eagerly returned his kiss.

Taking him by the hand, she led him to the bedroom.

Together they snuggled, Tom now dressed in his shorts, Jenna in her sweatpants and white tank top.

He kissed her cheek tenderly. "Thanks for helping me out tonight, princess."

"Of course," Jenna yawned. "Sorry I couldn't do more. But I promise to make it up to you this weekend. Don't forget, Trish is coming over. We can make our last weekend together before school starts a memorable one."

Again Tom felt his heart race at the thought, but quelled his desire. "I look forward to it. Now, get some sleep, hun. Love you."

Jenna was already snoring.

Tom smiled as he settled beside her.

He didn't need to hear it back.

He knew she loved him too.

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AUTHORS AFTERWARDS

So this is short. And hopefully sweet.

There's a reason for that.

It's been awhile since I've written a chapter for this series, and I needed to recapture the intimacy and connection between the two of them.

And I thought the best way to do that was bring it back around to where it started, but with a totally different dynamic now between them, and a different twist.

If you read the Summary I published recently on this series, you know I'm still considering its future and how long it continues.

For now, just know that I still have a few ideas left for this series, these characters.

Your continued support is, as always, much appreciated. And your feedback and comments are most welcome.