The Jenna Arrangement Pt. 22

Story Info
Tom, Jenna & Trish reunite for fun night out, then in.
5k words
4.8
7.9k
11

Part 23 of the 29 part series

Updated 03/16/2024
Created 08/22/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Djmac1031
Djmac1031
831 Followers

FORWARD

So for the first time in this series, it will be told in Third Person. I hope for regular readers the change won't be a distracting one.

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

----------------------------------------------------

"This is gonna be awesome!"

Jenna kicked back in her lawn chair, enjoying the warm August evening, bubbling over with excitement.

She'd finally received her trust fund money a few weeks ago, and while she'd promised herself not to splurge too often, she wanted to treat the two most special people in her life to a fun night out. When she found out Weezer, Fallout Boy and Green Day were coming to town, she'd immediately convinced both of them to let her buy the tickets.

Tom and Trish sat in their own chairs nearby as the sun slowly sank in the horizon. The concert wasn't due to start for another hour, but they'd arrived early so they could tailgate in the stadium parking lot before the show.

Tom was of course sipping an ice cold beer, and while neither of the ladies were legally old enough to drink, (Jenna having just turned twenty and Trish with her own twentieth birthday coming up,) they'd once again managed to convince Tom to purchase some wine coolers for them.

Tom knew the girls well enough not to worry that they'd overindulge and cause an issue, and with the parking lot packed with thousands of people, almost all of them indulging in alcohol or other forms of recreational stimulants, he doubted they'd even be noticed.

The girls were also smoking a little weed in vape form, taking discreet hits in between sipping their drinks. Tom, however, refrained. Somewhere in his late thirties, marijuana stopped doing anything for him except make him sleepy and paranoid.

As he watched his two young companions chatting excitedly together, he couldn't help but think how lucky he was.

The girls had decided to glam themselves up for the concert. Jenna's natural auburn hair was now streaked with a rainbow of bright colors, (easily washed out, she'd assured him,) while Trish had opted for simple white stripes to highlight her long, black curls.

They'd also glammed up their makeup, using brighter shades than usual, yet still tasteful enough to not look clownish.

At some point over the summer, Trish had gotten contacts, allowing her to now truly show off her beautiful brown eyes and thick lashes.

But it was their outfits that truly excited Tom the most. They'd gone shopping the other day and picked out matching black lycra skirts that were shorter and tighter than anything he'd ever seen either of them wear before. Around their waists they were matching black leather belts with silver studs.

Their legs were covered in black fishnet stockings; on their feet they wore black pumps with lattice cut outs that they both swore were more comfortable than they appeared.

Then there were the tops. This is where they differed, but only slightly. Jenna had taken an old white tank top of Toms and cut off the lower half at the midriff. She'd also ripped the neckline down the middle, leaving her wearing more of a tattered rag that barely covered her small, pert breasts. As usual, she'd forgone a bra, and even now Tom could catch a glimpse of her boobs from the side through the loose, open sleeves, depending on how she moved or bent.

Her Alexandrite gemstone necklace sparkled red in the fading sunlight, the chain dangling just above her freckled cleavage.

Trish's top was only slightly more sensible; a snug, short sleeved deep V-neck crop top with a cross wrapped tie up front that barely contained her ample breasts. Like Jenna's, it was white. And also like Jenna, she wasn't wearing a bra. Her dark nipples stood out quite well under the fabric.

Tom, never much of a fashion mogul, had opted for a much simpler outfit: jeans, sneakers, and a vintage Pink Floyd tee shirt he'd kept for years that finally fit him again now that he'd lost a few pounds.

He couldn't help but notice the stares the girls would get from men passing by, or the funny looks he'd receive as well. Most of them probably thought they were there with their father, which was fine with him. Whatever kept them from coming over and hitting on them.

Jenna stood and went to the cooler. "One more drink, then we should probably head inside."

As she bent over to pull out a bottle, her skirt rode up, revealing the tiny, black G-string she wore under it that left her ass cheeks entirely exposed and only barely covered her other bits.

"Hey, toss me one," called Trish, and as Tom glanced her way, he saw her cross her legs, revealing a matching G-string.

"Jesus," he thought, shaking his head with a grin.

He sat back and drained his beer, looking up at the setting sun and again wondered how he'd gotten so lucky.

Clouds were rolling in, filtering the remaining sunlight with a reddish-orange hue. The forecast called for a mostly clear night with potential rain showers moving through, but they hoped it would pass them by.

"May as well get me a fresh one too, darlin'," he called to Jenna. She brought it to him with a smile and as she leaned over to kiss him, he again caught a glimpse of her tiny tits under her barely there shirt.

"You planning on flashing the entire crowd tonight?" he grinned up at her.

"No," Jenna winked. "Just you."

----------------------------------------------------

Their seats weren't bad for a last minute purchase, on the lower level off to the left of the stage.

Weezer opened the show, and they found their seats just as the band took the stage. Fallout Boy would be the second act, with Green Day closing the night.

The girls were huge fans of all three bands. Tom knew both Weezer and Green Day very well, but was less familiar with Fallout Boy, knowing only a couple of their hits. But he liked what he heard.

The rain started coming down near the end of Weezer's set, and by the time they'd finished, the drizzle had become a downpour. It only lasted several minutes, but long enough to thoroughly soak the audience, including Jenna and Trish, their already revealing tops now rendered all but see-through.

Neither seemed to care and, to be fair, there were a LOT of wet tee-shirts by that point, and more than a few pointy, chilled nipples.

Despite the rain, they enjoyed themselves. Jenna and Trish had been dancing as Weezer played, water running down their faces, smearing their mascara, and they again drew more than a few stares when they pulled Tom up out of his seat between them during the last song, "Buddy Holly," playfully wiggling and gyrating, rubbing their rain-soaked breasts against him or grinding their asses to his crotch.

During the intermission, they decided to get out of the rain and headed for the concession stands inside.

Tom stood in line for a beer and some snacks while the ladies went to the restroom to clean up.

By the time they made it back to their seats, the rain had stopped. The night was still warm enough that they weren't chilly, but the humidity that hung in the air made drying out difficult.

Still, the girls had managed to clean up most of the makeup that had been ruined by the rain. Tom noted with some amusement that Jenna's white tank top was now almost a tie dye, stained with the multiple hues of hair coloring she had used.

She saw his look and laughed. "See? Told ya it washes right out."

Then the lights went down and Fallout Boy took the stage.

They were pretty good, Tom thought, but it was Green Day that truly stole the show that night, with hit after energetic hit.

The rain started again about halfway through their set, but only a light mist. Again, no one cared, the energy in the place more than enough to keep them all warm.

They closed the show with "Good Riddance (Time Of Your Life)" and the girls again surrounded Tom on both sides, gently swaying and singing along with the sixty thousand others in attendance.

"What a great night," Jenna exclaimed as the song ended and the lights came up. She grabbed Tom and pulled him to her, kissing him deeply.

Trish was still on his other arm, and when he came up for air, she moved in, kissing him just as passionately as Jenna looked on with a smile. Then she leaned back in and now both girls were kissing him. And then each other.

"Hell yeah, great fucking night," Tom agreed once the ladies had finally released him from their lip locks. He smiled down at the young couple a row in front of them, the guy looking at the girls with a mix of awe and surprise, his girlfriend looking at him with a curious grin. She was more than a bit wet herself, her concert tee clinging to her shapely body.

"I think she likes you," Jenna whispered in his ear. She always managed to catch him looking.

"Yeah, well, having two gorgeous women on my arms must be up-ing my hotness factor," he laughed.

"Maybe," winked Jenna. Then, softly, "She's got a great ass, too. Check it out."

Tom turned to watch the couple as they made their way out of the seats and the girl did indeed have a wonderful ass, wrapped snugly in form fitting yoga pants with no visible panty lines.

"Very nice," he agreed, "but not nearly as hot as either of you." Sliding his hands down, they found their way under each ladies skirt, gripping their butt cheeks with a light squeeze. Jenna and Trish both squealed in mock annoyance, their eyes and laughter betraying their true emotions.

"Hey! Save it 'til we get home, cowboy," Jenna smirked.

-----------------------------------------------------

The ladies were still a bundle of energy on the ride home. Tom had sobered up earlier (Jenna and Trish had drunk most of his last beer) and was feeling pretty good, all things considered. He'd taken the day off of work and the girls had let him sleep in this morning, so he'd been well rested. And tomorrow was Saturday, so he didn't have to worry about getting up early.

Traffic was heavy, but lightened up once they got out of the city, and they made good time getting home.

Tom had no sooner closed the front door when the girls started stripping. "I've been dying to get out of these wet clothes," Jenna said with a relieved sigh.

"You and me both," Trish laughed.

In moments, both were completely nude.

Although it wasn't the first time seeing either of them naked, or even the first time seeing them naked together, Tom still felt the rush all heterosexual men feel at the sight of two attractive young women so completely revealed. His blood warmed as he admired their curves, despite his damp chill.

He blinked as their wet clothes hit the floor, realizing something was missing.

"Where...what happened to your panties?" Tom asked, utterly shocked to realize they were nowhere to be seen when the girls had removed their skirts.

"Took them off in the ladies room," answered Jenna, pulling hers out of her bag. "Have you ever worn a wet G-string? Not fun!"

Tom's imagination ran wild, thinking of both girls dancing wildly all night beside him with nothing on under those micro skirts, and what kind of view anyone in the rows below them must have had if they'd happened to have turned and looked up.

"Dibs on the first shower!" Trish yelled, streaking down the hall to the bathroom.

"Don't you dare use all the hot water!" Jenna called after her as the door slammed.

Turning, she saw Tommy still standing by the front door, looking slightly dazed. "What?"

"Nothing," he chuckled, "just...still surprised by you two sometimes."

Jenna giggled, her smile quickly turning to concern. "You're still all wet, too. Come on, off with them before you get sick!"

"I'll undress in the bedroom, thanks," he insisted.

Jenna followed him into the room, throwing herself down on the bed as Tommy peeled off his wet clothes. He debated getting completely naked, but his boxers were still dry, so he left them on for the moment.

"Getting shy on me all of a sudden?" Jenna teased.

"No," he shrugged, "just...still not sure about it with Trish here."

They hadn't seen Trish for several weeks, ever since she'd stayed over a few days after they'd picked up Jenna from her mother's.

Tom had let the ladies use the bed while he'd slept on the couch. Jenna had still been down about what had happened and Trish had been there to support her. There had been no fooling around between the three of them then, and Tom certainly hadn't expected anything.

The next few weeks had been busy, so they hadn't reunited again until yesterday when Trish came over via Uber to go on a shopping trip with Jenna to get their outfits for the concert.

Trish had been affectionate and friendly of course, but there'd been no hints about anything sexual happening, and when Tom again suggested he'd take the couch last night, neither of the girls had objected.

"It's nothing she hasn't seen before," Jenna reminded him.

"I know, but...I just don't wanna assume anything, ya know?"

"I get it," said Jenna. "Always the gentleman, you are. And I love that about you. But you get in your head too much."

"Yeah, probably," he shrugged. "But this whole...openness thing...is still kinda new to me. And Trish and I technically aren't a couple. So I'll leave it up to her. If she wants to, well, see me walking around naked, she'll let me know."

Jenna smiled. "Yeah, you're probably right."

Trish returned to the bedroom several minutes later to find her friends relaxing together on the bed. Tossing her towel aside, she went to her suitcase and began rummaging for her sleepwear.

As she bent over she heard a giggle and, looking up, saw Jenna, now sprawled on her belly facing the foot of the bed, her legs kicking playfully in the air. She was still naked, her adorable bare bottom facing Tommy, who was propped up on the headboard, staring wide eyed with his arms folded not quite casually over his lap.

"What?" snipped Trish.

Jenna laughed again, looking back over her shoulder at Tommy. "Guess that answers your question, huh?"

Trish shook her head and smirked. "Men and their boners." She returned to digging through her clothes, slipping on a pair of terry cloth shorts and an oversized night shirt.

Jenna had already scampered off the bed to go take her shower. Trish took her spot, plunking herself down next to Tommy. "What question?"

"Nothing, forget it," he chuckled.

"No, seriously, tell me," she insisted.

"Fine," he sighed. "It's just I was worried about whether or not you were still comfortable about me walking around naked, and then you came in and just dropped your towel."

Trish laughed loudly. "Oh God, you're too funny! After everything we've been through???"

Tom flushed a bit in embarrassment but managed to laugh at himself. "I know, I know."

Trish kissed his cheek. "Look, I appreciate you being thoughtful. I really do. But I think we should be beyond being embarrassed or weirded out by seeing each other naked by this point, don't you?"

She tugged at his arms playfully. "So stop trying to hide your boner around me, Big Guy!"

"Hey!" Tom objected with a laugh. They wrestled together on the bed, Trish giggling hysterically as he half heartedly fought off her attempts to strip off his boxers.

"You two starting without me?"

Jenna stood in the doorway, wearing nothing but a smile and a towel around her damp hair.

"Just trying to free the Big Guy from his sudden case of shyness," Trish grinned.

"I can help with that!" Jenna sprang forward with a leap onto the bed, and soon Tom was powerless to keep the two hyper young women from pulling off his last article of clothing.

His erection bounced to-and-fro as the girls pinned him down. "Men and their boners," Trish repeated, arching her brow with a wry grin.

Jenna leaned in to kiss him, then stopped. "You smell," she said, wrinkling her nose. "Go get your shower, sweaty man."

Tom reluctantly freed himself from the ladies' grip and made his way dazedly to the bathroom.

The girls dried their hair while he showered, and when he returned he found them both dressed for bed, Jenna now in her blue boy shorts and a cute white camisole.

"How was your shower?"

Tom eyed Jenna with a smirk. "Lukewarm. And I think a clown melted in my bathtub."

"Oops," she giggled. "Forgot to rinse it after washing out the last of my hair dye. Sorry!"

"No worries," he smiled. "I took care of it."

Tom pulled his bath towel from around his waist and threw it casually over his shoulder as he strolled to his dresser, his now only semi erect cock swinging with each step.

The girls watched him from the bed as he pulled his baggy gym shorts from the drawer. "You won't need those," Jenna piped up.

"Yeah I will," he said. "It's kinda weird sleeping naked on the couch."

"Then don't sleep on the couch," grinned Trish.

Tom froze, looking at both of them intently. "Really?"

"Yes, really," they said together.

"Fine," he shrugged, trying to still play it casual despite his rapidly increasing heart rate. His cock betrayed him of course, once again beginning to rise to full mast.

As he climbed into bed between them, Jenna stretched herself with a loud yawn. "I'm so tired. Wore myself out with all that dancing. I'm gonna sleep like a rock tonight."

"Me too," Trish said, echoing her yawn.

The girls leaned in, kissing him on each cheek. "Well, goodnight." They both rolled over and Jenna reached out, turning off the light.

The room was dark, lit now only by the moonlight streaming in through the window.

Tom lay there, snug between his two female companions, staring up at the ceiling in confusion with a disappointed look and a reluctantly fading erection. The girls were already snoring softly beside him. "Ah well," he thought. "Maybe next time."

Jenna rolled over, grumbling sleepily under her breath, her arm flopping across his chest as she settled in beside him.

Moments later, Trish turned as well, her hand landing on his stomach.

Tom lay still, tense, unsure of what was happening, until both hands started moving slowly over his torso, coming together at his midsection.

Then, ever so slowly, they began to slide downwards.

"What the...?"

"Surprise!" they chimed, sitting up with a start. "You really didn't think we were just gonna roll over and go to sleep, did you?" Jenna giggled as she flipped on the light.

"You...you set me up! You little teasers!"

"Oh, come on. Just admit we got you good," Trish snickered.

"That you did."

The girls were still holding hands, just above his pubic bone. His cock was already beginning to stir again as they moved in unison over it.

Tommy threw back the covers so he could watch as both girls began stroking his rapidly swelling shaft, bringing him back to full erection in seconds, their soft warm bodies snuggled close as they took turns kissing him.

"When did you ladies plan this?"

"While you were in the shower," Jenna grinned.

Tom rolled over, reaching out for her, but she pushed him back gently. "Relax. Just lay back. This is just for you. We've got something...special in mind."

His confused grin quickly changed to excited anticipation as the girls began kissing their way down his bare chest and stomach.

Moving down by his legs, they continued torturing him, Trish's long dark locks running over his skin as she kissed her way along his hip bone, Jenna's auburn hair tickling his balls as she kissed his inner thigh.

Their lips worked over him, moving slowly closer to his now maddeningly hard cock.

Jenna took his throbbing shaft in her grip, then pointed it towards Trish. "You're our guest here, so you first."

Trish's dark brown eyes met Tommy's with a bright twinkle. "Hang on a sec; took my contacts out before my shower, can't see a thing without my glasses."

She jumped up and grabbed them from the nightstand, then resumed her position. "There, much better," she grinned. "Plus, I may need eye protection."

Djmac1031
Djmac1031
831 Followers
12