The Jenna Arrangement Pt. 07

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Jenna & Tom have their 1st date with an unexpected guest.
4.3k words
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Part 8 of the 29 part series

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

ALL CHARACTERS ARE 18 YEARS OF AGE OR OLDER.

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"We need to talk."

My car speakers clearly picked up the nervousness in Jenna's voice. I was on my way home from work when she called.

"What's going on?" I asked, trying not to let my worst fears get to me. She wasn't about to cancel our date or, worse yet, break off our relationship entirely, was she?

"I have a friend that wants to come with us on Saturday."

It took me several seconds to sort out my mix of relief and surprise before I could respond. "How did this happen?"

There was a pause before Jenna answered, "So... I was showing my friend Trish some of my art sketches since we're both prepping for the nude model project coming up next week, and I...kinda sorta, well...showed her my sketch of you."

My mind flooded with several thousand thoughts at once, but the best reply I could manage was a shaky, "Oh, really?"

"Please, don't be mad," pleaded Jenna. "It was mixed in with my other sketches and I forgot it was in there till she saw it. She was gushing over it, really liked it, and asked me who my model was."

"And how much did you tell her?" I asked, trying to sound calm.

"Oh, everything, of course," replied Jenna.

"Really?" I gasped.

"Of course not, silly," she laughed. "I told her we met at the diner, and how you gave me a ride home during the storm. I told her we spent some time together that night, and we kinda hit it off. I didn't tell her all the details, of course. But I did tell her about how you wound up soaking wet and I needed to wash your clothes and how that led to you modeling for me while we waited for them to dry."

"She must have found that...interesting," I mused.

"Oh, she was concerned about me bringing home a total stranger, let me have an earful about that, and the age difference of course. And I think she suspects I did more than just sketch you," she giggled.

I was silent for a while as I tried to sort this all out. "You're not mad, are you?" Jenna sounded concerned. "I'm really sorry, I guess I shouldn't have told her anything, but I'm not a very good liar and besides, if we're gonna be seen in public together anyway then I don't see much sense in trying to hide you."

"I'm not mad," I said, finally getting my head together, "just surprised I guess. I thought maybe we were sticking to the 'uncle' story or something."

"I thought about that, but it's just too complicated," Jenna sighed. "And besides, I'm an adult, I can see who I wanna see, we're not doing anything wrong, and I don't have to explain myself to anyone."

I could clearly imagine the cute determination on her face to match the tone of her voice. "Hey, Jenna, look, I'm all for it, and I'm thrilled you're not ashamed or embarrassed to be seen with me. I just want you to be sure, because you know how people are. I just don't want you...regretting it, later."

"The only person who could make me regret any of it would be you," she said, matter of factly.

I wasn't quite sure how to take that, so I let it go. Instead, I asked, "So how did she wind up tagging along with us?"

"Well, turns out she was going already. When she found out we were going, she asked if she could get a ride with us. I can tell her no, if you want, but she's gonna be there either way, so..."

"Nah, it's fine. I'm okay with it as long as you are. Although I wasn't really expecting a chaperone," I joked.

"I'm sure she'll give us some space once we get there. Lots of people from school will be there, so hopefully she'll go socialize," said Jenna.

"Well I guess it's settled then. I look forward to meeting her. Oh, and I have an extra floatation tube if she needs one," I said.

"Really? Great! You can come by early if you want. The lake is open the whole day; we could make a day of it." Jenna suggested.

"Sounds good. How 'bout I pick you two up at noon?"

"That would be perfect! Yay! I'm so excited! See you then!"

‐-------------------------------------------------------------

Meeting Trish was a little awkward at first, but thankfully she didn't go out of her way to ask any embarrassing questions, although I did see her arch her eyebrows after Jenna greeted me with a hug and a quick kiss.

It was a beautiful afternoon, and while the movie didn't start until sundown, the girls wanted to get to the lake early so they could spend some time swimming.

We stopped along the way for some snacks and drinks, and while I was hesitant about buying alcohol for two nineteen year old girls, they talked me into getting them a six pack of wine coolers. I figured they couldn't get too drunk off of that. I put them in the cooler along with a few beers for myself.

The lake was already starting to fill up with people as we arrived, but we found a little spot on the beach to set up a blanket and our supplies.

The girls had worn their swimsuits under their clothes, and as they stripped them off, I had to fight my instincts to stare at either of them for too long.

Jenna looked fabulous in her green one piece that almost matched her eyes. The front was modest, fully covering her breasts with only a hint of cleavage. The back was a little more risqué, completely open, highlighting her firm bubble butt. While not exposing a lot of skin, the suit was form fitting and complemented her petite frame nicely.

The best way to describe Trish is that she looked like one of those "geeky" girls you always see in movies before they get their makeover and become a "hottie."

Her shoulder length,curly black hair framed her cherubic face, with black horn rimmed glasses that made her eyes look too big until she took them off.

She was about the same height as Jenna, but stockier. Not fat, or even heavy, really, just...thicker, more curvy when compared to Jenna's thinner frame.

She wore a two piece suit that I couldn't help but grin at when I recognized the blue and white R2-D2 design. I considered making a "these are the Droids you're looking for" joke but thought better of it in case she mistook it for a reference to her breasts, which were much larger than Jenna's.

Trish trotted off towards the water, but Jenna lingered behind, sitting down next to me on the blanket.

"So, what do you think of Trish?" she asked.

"She seems...nice," I replied.

"She's cute, right?" Jenna asked slyly.

"Well, sure, I suppose," I said, not sure what Jenna was fishing for.

"Hey, it's okay. You can look at other women, I don't mind. And you can be honest about it. Do you think she's sexy?" Jenna seemed intent on getting an answer out of me.

So I gave her one. "Yeah, okay, sure. She's a beautiful girl, and sexy in her own way. But not as sexy as you."

Jenna smiled. "Good answer." She gave me a soft, quick kiss, then scampered off towards the water.

I stayed behind to unpack and inflate the floatation tubes. I was already in my swim trunks, and since the sun was warm, I decided to take off my shirt.

The beach was a mix of college kids and families, and glancing around at some of the guys there my age made me feel a little less self conscious about my body and glad that I'd kept up with my workouts. I couldn't compete with some of the young college guys there, but I was certainly in better shape than most of the other older men.

After I inflated the tubes, I cracked open a beer and sat back on the blanket, looking for the girls.

They weren't too far off, swimming and splashing in the water. Jenna looked so happy, and I found myself smiling while watching her youthful exuberance.

Eventually they both made their way back to the beach, and as they left the water, I saw several young men checking them out. One let out a low wolf whistle. Trish looked annoyed, but Jenna just smiled as she walked past, totally ignoring them.

When she got back to our blanket, she bent down to pick up her towel. She bent slowly at the waist, deliberately mooning the young men she knew were still standing not far behind her, staring at her ass.

Her eyes met mine, and she winked. Jenna straightened up, dried herself quickly and wrapped herself in the towel. "Show's over, boys," she whispered, grinning at me.

Our blanket was more than big enough for all three of us, but Jenna sat down very close, nuzzled up to me and kissed me in a way that would dispel any thoughts by onlookers that perhaps I was her father.

I was loving Jenna's pure confidence. She knew those guys were looking, and knew I'd noticed it too. In one swift move she'd simultaneously tortured them while demonstrating she was there with me.

Two of the guys snickered, the wolf whistler just scowled, shaking his head. I had to resist the urge to flip him the finger.

Trish sat across from us on the blanket at a more respectful distance. Her eyebrows were arched again, but this time more amused than judgemental.

"I'd say that was cruel, Jenna, but those assholes deserved that," laughed Trish.

Jenna put on her best innocent "who, me?" face, then laughed as well.

We broke out some snacks and the girls each helped themselves to a wine cooler, and for a while we just lounged in the sun, chatting.

The girls did most of the talking, telling me about how they'd met and their shared classes and about how they hoped they could room together next semester.

Then Trish brought up the art project. "So when is that nude model class happening this week? Friday, right?"

"Wednesday," corrected Jenna.

"Shit!" said Trish. "I was hoping to have more time to prepare. I was thinking about practicing with some pictures from online or something since, unlike you, I don't have a live model handy."

I was grateful that the sun had warmed my skin enough to hopefully hide my flushed cheeks.

"Well, maybe we can figure something out," said Jenna casually, as her arm slipped around me and softly stroked my back.

My brain froze. Did she just volunteer what I think she did?

Before I could untie my tongue enough to chime in, Trish replied, "Well, I could definitely use your help, Jenna. Your sketch was so lifelike. Especially now that I've met Tom in person." Trish turned to me. "You saw it when she was done, right? Do you think it captured the real you?"

Now I have to stress here that there was no sexual innuendo in her voice or in any of the conversation to this point. She was simply an artist discussing art. It's just that the art being discussed happened to predominantly feature my fully erect penis.

"I...I think Jenna did a wonderful, if somewhat generous job," I managed to stumble.

"Well, I hope not TOO generous," quipped Trish.

Jenna grinned slyly. "Oh, not generous at all. My proportions were very...exact."

Jesus. Now they WERE talking about my dick.

Trish arched an eyebrow again, and I could have sworn I saw her eyes glance downwards at my crotch. She opened her mouth as if to reply, but instead just shrugged and sipped her drink.

I was praying for them to change the subject, and it was Jenna who did. "Do you guys smell chicken?"

We did. It was coming from one of the vendor booths, the savory scent of fried chicken that immediately set all our stomachs grumbling despite our light snacking.

I immediately volunteered to go get us some, grateful to have the excuse to break from the girls for a bit and clear my head. Both of them.

While standing in line, a young man approached me. It was the Wolf Whistler. "Hey, I gotta ask. How does an old dude like you score a hot chick like that?"

I looked him dead in the eye. "Well first of all, I don't call them 'chicks' or whistle lewdly at them. Try talking to a woman sometime, let me know how that works out for you."

The father with two kids behind me in line laughed. Wolf Whistler just scowled. "Yeah? Well maybe I will. Maybe I'll go talk to her and convince her to try dating someone who isn't old enough to collect Social Security."

I smiled thinly. "Her name is Jenna. She's an adult and free to talk to whoever she wants. By all means, go talk to her, I don't mind."

Wolf Whistler glared and stalked off. The guy behind me chimed in, "You really gonna let that guy go talk to your girl? You're a braver man than me."

I just shrugged. "She can handle herself."

I couldn't let myself get dragged into feelings of jealousy. Jenna was a beautiful young woman, and she was going to attract the attention of other men. If I let myself get angry or paranoid every time another guy looked at or talked to her, I'd drive myself crazy. I had to trust her.

The line for the chicken was long and it took awhile, but it smelled so worth the wait.

I made my way back slowly, not wanting to spill the food. As I approached I saw Jenna standing face to face with the Wolf Whistler. Trish was standing beside her, and a small crowd had gathered around them.

Jenna looked angry, and their voices were raised, but I couldn't make out what they were saying.

I quickened my pace and was debating about whether to interfere or let Jenna handle him on her own, when Jenna said something sharply to him then turned to walk away. Wolf Whistler put out his hand and grabbed her by the shoulder roughly.

I was about to drop the chicken and run in, but Jenna reacted so quickly I didn't have the chance.

Spinning around with lighting speed, she dropped forward to her knees in the sand, her hands landing at Wolf Whistler's hips, and with one swift yank, pulled his bathing suit down around his ankles.

Time froze for a second and the crowd went silent. Jenna lifted her head, which was waist level with him, and her eyes went wide. She started laughing hysterically.

She was staring at the smallest dick I've ever seen.

Now maybe the water was cold that day; we men all know what that can do. But neither his suit nor his hair looked wet, so I don't think he'd been swimming recently. He didn't appear to even have a shaft, just a tiny little mushroom cap and two small, hairless balls. To make matters worse, the guy was completely shaved, leaving nothing to the imagination.

Jenna fell backwards on her butt, still laughing. Other people in the crowd started laughing as well, including several young women. Trish was still standing there, her hand over her mouth and her eyes wide in surprise.

Wolf Whistler looked confused, then his face dawned with the understanding of what just happened. He made the mistake of trying to take a step backwards, tripped over his own suit, and landed on his back with a thud.

Now the crowd was laughing even louder as he lay in the sand, naked, his tiny penis flopping around like a little goldfish.

His friends were trying to help him to his feet (even they were laughing) when two lake security officials arrived.

"What's going on?" They stopped short when they saw the guy struggling to his feet. His suit had slipped off completely when he toppled over and was still laying in the sand in front of him.

"That little red headed bitch just attacked me!" The Wolf Whistler yelled. He tried lunging at Jenna only to slip and fall to his knees, causing more peels of laughter as his little willy bounced around.

The female security guard, a woman I'd put around her mid-forties, had to cover her mouth to hide her smile.

The male guard was less amused. "Is that true?" he snapped at Jenna. Jenna's face froze, and she could only look up at him from the ground, frightened.

"Excuse me, sir," I said, stepping in, "but that's not what happened. This guy tried to grab her, and she slipped and fell on him, and accidentally pulled his suit down trying to stop her fall."

Trish immediately chimed in, "I saw it too, that's exactly what happened. This guy kept bothering us, wouldn't leave us alone, and when Jenna turned to walk away he grabbed her and she fell."

Several others in the crowd were now nodding or vocally agreeing, supporting my story.

Wolf Whistler was on his feet again, his face flushed red with anger. "That's not true! She did it on purpose!" Suddenly it struck him just how many people were looking at him, and that he was still naked. His little cock began to twitch and in moments he had an erection.

If you could call it that. He was two, maybe three inches if I was being generous.

Many of the women started giggling again, but the male security guard cut it off. "All right, get your shorts back on, Junior, for Christ's sake. This is a family beach. We don't tolerate this kind of behavior here. Time for you to go."

Wolf Whistler awkwardly got dressed, and the two guards escorted him off the beach. "Bye, JUNIOR," a young woman's voice called out, to a round of laughter and applause. Show over, the crowd eventually dispersed.

Jenna was helped back on her feet by Trish, then came running over to me, hugging me so hard I almost dropped our chicken. "That was brilliant, thank you for covering for me," she said.

"You were pretty brilliant yourself," I chuckled. "I only came in at the end so didn't see the whole thing, but I'm willing to bet he deserved that."

"Oh, he did. But I don't wanna talk about him, not worth repeating what he said. And besides, that chicken smells amazing, and I'm starving!" Jenna turned to Trish, waving her over. "Come on! Food's here. Let's eat!"

The chicken was indeed spectacular.

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We laid in the sun for a while, soaking up some rays while digesting our meal. Jenna helped put some sunscreen on my back, then I returned the favor. Although it wasn't really sexual, I did have a moment to think that this was the most I'd ever actually touched her.

Trish eventually went off to find a few of her other friends that had just arrived, giving Jenna and I some alone time.

Jenna wanted to go swimming again, and convinced me to join her. The water was indeed cold, but refreshing after laying in the sun.

After splashing around playfully for a bit, Jenna swam over close and slid her arms around me. "Did you really tell that guy my name, and that he should come talk to me?" she asked suddenly.

"I did," I answered honestly, "although I didn't think he'd actually have the balls."

"Well he barely did," she laughed. "Why did you do that, though? Weren't you worried about him hitting on me?"

I thought about my answer for a few moments before replying. "Jenna, look, guys are gonna hit on you, whether I'm around or not. I can't stress out about that. I trust you. You can talk to other men, you can look at other men, just like you said I could look at other women. Will I feel jealous? I can't promise I won't sometimes. But I also know if I let that kind of thing eat at me, this, whatever this is we have, will never work. So I'm just going to trust you, as I hope you trust me."

Jenna nodded and smiled. "Thank you. I appreciate your trust. And I trust you, too." With that she leaned in close and kissed me.

Up until this moment, our kisses had been romantic, but short. Now though, we were passionate, our tongues slowly dancing together playfully. Jenna threw her arms around my neck and wrapped her legs around my waist. My hands went around her back to support her.

Together we moved a little deeper into the water until we were about chest deep. Jenna and I continued to kiss off and on, breaking occasionally to look around and make sure we weren't being stared at. Normally I'm not a big fan of public displays of affection, but despite other swimmers being around, no one was really paying any attention to us, and as long as we kept it discreet I thought we'd be okay.

I put aside my worries and focused on enjoying being this close to Jenna for the first time. Her little body felt light in my hands, the buoyancy of the water helping support her weight, and my hands felt free to explore her back with light caresses. Her hands moved across my back as well, sending light chills through me. Her touch was lovely.

Djmac1031
Djmac1031
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