Nyland and Pamela (A chapter from "Helping Out")

[TiredFingers]

Nyland and Pamela

(A chapter from "Helping Out")

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(OOC thread for profiles and more.)
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Explanation: This is a conversation/interaction primarily between two characters from the roleplay, "Helping Out". We are writing this here because it is easier, to both write and read. This 1x1 left the main thread from here. When we close this 1x1, we will take you right back there.

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Nyland Cahn, at the Northend "Squatters" Camp with Pamela King (Map link -- NSC is at the very top)

A bit after noon, Sunday, March 22, 2025

Nyland heard footsteps approaching and turned to find Pamela King approaching. He'd actually expected someone from the neighborhood to come up and ask him what Deputy Evans had wanted. Curiosity was the only thing in overabundance in the squatters' camp.

She greeted him simply, "Hey."

"Hey," Nyland returned.

"Hey, I saw that cop hand you something," Pamela said. "I don't suppose it was for Roxanne's."

"Yeah, they are," he answered.

He'd already shoved them down into a pants pocket but now took them back out. Nyland knew what she wanted: a free dinner. He didn't blame her. Nyland's life sucked, and sometimes he went without three meals a day. Sometimes, he went without two. And yet, he was sure that he lived better than Pamela did on the average.

He also knew what she'd do for a free dinner, and as if she was reading his mind, Pamela said, "I thought maybe ... you know ... after we had come fun in my trailer ... you could take me to lunch."

"No," he responded without hesitation. Then, seeing her reaction, Nyland clarified, "You don't have to do that, Pam. I'll take you to dinner." He looked at his watch, then corrected, "Dinner. And you don't have to ... you know..."

He looked down her frontside, not necessarily to ogle her but to indicate that he understood what she was offering. Still, it was a nice view. Pam had a nice shape to her, with nothing particularly outstanding about her but with everything put together and stripped naked, still very nice. She was what Nyland's father would have called a real woman, and not some airbrushed lingerie model.

Nyland had seriously enjoyed his time as Pamela's lover, but shit happens, and they'd gone their separate ways. Well, except for back when he was dealing small quantities of week, coke, meth, and smack and she'd suck his cock for a night's worth of whichever she'd needed at the time. But he didn't do that anymore, which meant that she didn't. Well, except for right now. Nyland was torn about whether or not he should be relieved that she was willing to give him a blowjob for actual food rather than dope.

"That okay?" he asked. He hoped he hadn't offended Pamela. Maybe she'd just wanted to get fucked for fuck's sake, and asking to join him for dinner had been incidental.

 

[CutiePie1997]

Nyland responded to Pamela's offer of sex for dinner with a quick, "No."

He would in a moment become concerned that he'd offended her, but really, he'd only disappointed her. Just as he suspected, she wasn't eating regularly. She hadn't had a fully nutritious meal since yesterday about this same time. Dinner last night had been a bowl of cereal without milk. This morning she'd had donuts, milk, and coffee courtesy of one of the support groups at a Toland church. Her stomach was growling now just at the thought of laying her hands on one of the little scraps of paper that Nyland held in his hands.

He added, though, "You don't have to do that, Pam. I'll take you to dinner." He checked the time and corrected, "Lunch. And you don't have to ... you know..."

Nyland didn't have to look Pamela up and down for her to understand what he meant. He asked, "That okay?"

"Perfect," she said, her smile widening. She asked with a bit too much eagerness, "Now?" She looked down at her blouse, which was actually a ratty old tank top. Her nipples, hardened by the March chill, showed so conspicuously that she said, "I should put on something else and hide these things."

If Nyland confirmed that they were going now, Pamela would go change, maybe touch up her hair, and be back in just a couple of minutes.

 

[TiredFingers]

"Now?" Pamela asked when Nyland said they should go to lunch right away. She looked to her blouse, through which her nipples were well displayed. "I should put on something else and hide these things."

"If you want," he said, smiling devilishly. He laughed. "No, yeah, you probably should. I'll wait."

He watched as she hurried back to her trailer. He liked watching her from behind. She had this wonderful, pear-shaped ass that swayed and rocked with every step. Nyland often found himself wishing that he was still fucking Pamela. But they'd been going nowhere, and slowly over their time together, their time in bed had become more of a transaction than a relationship. Progressively, he'd given her more and more things of a financial nature as Pamela had given him of a sexual one.

As Pamela changed and gussied herself up, Nyland took a short walk to Ginger's. Like many if not most of the residents of Northend, Ginger had lived and worked in Toland before her slide into homelessness. She was doing better than most of her neighbors, though, with two part-time, minimum wage jobs, a nice 2002 22-foot Airstream trailer, and a minivan that ran more often than not.

But Ginger wasn't above a little wheeling and dealing, though, so when Nyland got to her space, he flashed one of the dinner coupons as he asked if he would borrow her car. He smiled, saying, "I got a date."

Ginger congratulated him without asking with whom the date was, thinking it wasn't her business. She handed over the keys but only after he agreed to two of the coupons. She pointed an extended finger at him, saying, "Don't wreck it! And gas it up. I filled it this morning."

He thanked her, waited for Pamela, then headed for Roxanne's.

 

[CutiePie1997]

Pamela was surprised when she left her own trailer house to find Nyland waving her over toward Ginger's Airstream. She headed that way, learning that he'd traded some of his certificates for borrowing the woman's rig for the afternoon. Pamela wanted to remind him that she'd offered him the service of her mouth for some of the coupons and would have been happy to ride to Roxanne's in his old box van or even walk the ten blocks. But she didn't. He was feeding her for free, so why mess with that.

Walking into the cafe, Pamela made a quick scan of who was here for a meal. Most of Toland's population had no idea who she was, despite her having lived in the town all her life. It was those who recognized her that she didn't care to see here. Some of them knew of her issues with drugs and unemployment. Some knew she was homeless, or what the media was nowadays calling unhoused. Whatever. She was living in a trailer house with no electricity in a condemned portion of a dying town. Without the responsibilities that most of the normal, good, decent people had, sometimes Pamela wondered if maybe she was the lucky one.

She didn't see anyone of consequence here tonight, which left her at ease. They found a booth and got their menus from the waitress, a teen named Betty. Pamela knew there was some sort of relationship between Betty and Roxanne's owner, Dick Donner, but she didn't know what it was.

When Nyland showed the girl the certificates for a free dinner, Pamela's first thought was to lean in toward the girl and whisper, "Don't worry, you're not gonna get stiffed on the tip."

Many times, people using the certificates for free meals often didn't tip or tipped poorly. Pamela knew this firsthand, as there had been times when she had had one of the coupons but didn't have any cash for the tip. And Pamela had heard that Betty worked for just tips since Dick couldn't afford to put her on payroll, what with taxes, workers comp, social security, and everything else that came with a job like this.

Ironically, Betty smiled, pointed to the number 15 that had been hand-written in the corner of the certificate, and responded, "Don't worry about it. Whoever bought this for you paid the tip, too. You're covered." Then, smiling wider, she added before taking the order, "But thank you so much for thinking of me."

Pamela looked to Nyland, to whom the coupon had been given, and said, "Why don't you order first."

It might have looked like she was simply being polite, but Pamela had an ulterior motive. By hearing what Nyland ordered and casually checking the prices on the menu, she could order something a bit pricier if there was a dollar or two left over. Pamela was good and quick with math, which came in handy at times like this.

 

[TiredFingers]

Nyland hadn't considered the tip yet because, obviously, they hadn't even ordered yet, so it was to be a while before it would be necessary. He did have cash in his pocket, but he was still happy when Betty explained that the tip had already been paid.

Pamela told Nyland, "Why don't you order first."

"Sure, um," he responded, again not considering the why behind Pamela's directive. He glanced at the certificate sitting on their table, did the math, and knew he had $15 to spend on himself, leaving the other half to his date. It didn't matter, though, because Nyland had his favorite foods, and price wasn't an issue in this case. "I'll have the grilled cheese with ham on wheat and a slice of whatever the berry pie is today. Just water to drink, please. Tap is fine, with ice."

Rounding up the prices on the menu, Nyland knew that that ran about $12, leaving a bit left over for Pamela to use. He handed Betty the menu, looked to his former lover, and asked, "What looks good to you?" He leaned in closer and said softly, "I have some cash in my pocket, in case something a bit more pricy looks particularly delicious today."

 

[CutiePie1997]

As Nyland ordered, Pamela inconspicuously looked at what he'd chosen, did the math, too, and realized that her date had left her $18.40 cents, plus or minus a couple of pennies. That pleased her, because she knew what she wanted. Nyland told her, "I have some cash in my pocket, in case something a bit more pricy looks particularly delicious today."

"No, that's fine," she said, "I already know what I want." To the waitress, Pamela said, "I'll have the meatloaf, a baked potato, a small green salad, first, please, if that's okay, with Thousand Island on the side, and a slice of the sweet potato pie." She ran the numbers through her head quickly, then added with a smile, "And a glass of milk and a slice of pie for Khan here."

If she was correct, there would be thirty or forty cents left over when the tab came to them. Pamela help but think that if she'd so quickly and skillfully calculated the toll that drug addiction would have played on her life, maybe she wouldn't be living in an Airstream in an abandoned portion of the city, offering blowjobs in exchange for dinner.

The waitress took Nyland's pie order, assuming he gave one, and wandered off. Pamela smiled happily to her date, tickled with how things were going. She asked him about his salvage work recently and whether it was making him any money. Over the years since Toland Corporation Inc went down, most of what was worth salvaging had already been. The campus had gone later, though, and still had plenty of stuff to collect.

They would chat about this and that until their meals came, and then it was mostly just about getting down as many calories as possible before their stomachs were full. Pamela ate the portions that wouldn't keep well when she took them home in a doggy bag.

Only after they'd begun eating, with a bit more enthusiasm than the typical diner, did Pamela first notice that the pair had the attention of some of the other diners. Both Nyland and Pamela had dressed in their best for dinner out in public, but still some might understand that the pair were from the Northend.

Pamela suddenly felt very self-conscious, and her happy mood began to fade a bit. She hated what had come of her life, but what was she to do about it? There was no work in Toland, and she couldn't afford to leave it any more than stay.

Of course, she had no idea what was in store for her and others in the days, weeks, months, and possibly years to come due to the arrival of the very generous and very sympathetic Viola Dean.

 

[TiredFingers]

Nyland didn't take any undue notice of Pamela's order being specific to the value of their gift certificate. He smiled when she finished with, "...and a slice of pie for Khan here."

"I already ordered pie," he pointed out, adding, "But I'll take two of'em."

She asked him about his salvage work, which brought Nyland back to the reality of their situations. "Yeah, the campus is still providing some salvage. We're not supposed to be up there, but..."

He let the thought go. Nyland had never considered himself a criminal, even after he'd started trespassing on some of the abandoned properties and collecting steel, wire, and more. He never trespassed on occupied properties or under-construction houses. That was a quick ticket to prison. Not jail. Real prison.

The meal was incredible, as it always was. Nyland ate here more often than did some of the residents from the Northend. He was a live for the day kind of guy. He spent two or three days filling his truck and trailer with scrap, ran it to the recycler, came back to Toland, and spent what he had. There was always something he needed, be it food, gasoline, tools, condoms, whatever.

Nyland usually kept a little nest egg, $100 generally. He did all he could not to break into it. If he had to work more hours on more days, he did. If he was flush, he took time off. There'd been times, though, that he'd gone hungry not to tap into that money.

Nyland didn't notice that he and Pamela were attracting any undue attention. He didn't care what people thought of him as much as she did. He never had. It seemed to make life easier.

They finished their dessert, and even though Betty had said that the tip was already covered, Nyland left a five-dollar bill under the sugar dispenser. They headed out, but instead of returning to Northend, Nyland pointed the minivan eastward. He told her, "I told Ginger we might not have her car back until after dark. So, I thought maybe we'd go out to Viz Rock and watch the sun go down."

They drove east out of Toland to Vizcaino Park. Once upon a time, it had been a popular County Park with picnicking, camping, and fishing on both the river and in a pond that had been there. There had been a boat ramp and dock until the Vizcaino River shifted during the same rain event and flood that had ruined Northend. The flood had filled the pond with polluted sludge, destroying the fishing.

When the County began cutting its Parks & Recreation budget, the Viz was the first park to get the ax. It had a gate across the entrance, but the lock didn't work and could be jiggled open. All you had to do if you wanted to get in was pull the lock, open the gate, drive through, close the gate, and not be conspicuous. No headlights, no blaring stereos, no fireworks, etc.

Nyland did just that, and a couple of minutes later they were parked at their destination. Viz Rock was a 30-foot-high cliff that had been carved by the river over tens or maybe even hundreds of thousands of years. Kids and young adults had been coming up here to park and make out and fuck for decades. The first time Nyland and Pamela had fucked was up here. It had been great.

By the time they finished lunch, go to the park, and found a parking space looking west over the city, the sun was just minutes from touching the distant horizon. Nyland sighed, pleased, saying with a sincere tone, "I love this place."

 

[CutiePie1997]

"I told Ginger we might not have her car back until after dark," Nyland told Pamela. He followed up with, "So, I thought maybe we'd go out to Viz Rock and watch the sun go down."

She laughed loudly, but then asked quietly, "We're gonna go out and park like a couple of teenagers?"

It was just a dozen minutes or so later than they were getting out of the minivan and standing on the cliff, looking out over Toland. It was a beautiful view, one that each of them had enjoyed often, together and with others as well. Or at the least, Pamela had. She'd necked and fucked up her far too many times to count, both before and after they'd gated the entrance to the park. Had Nyland? She didn't know, and she certainly wasn't going to ask.

The only time up here that Pamela cared to remember was the first time she'd been here with Nyland. They'd been up here in her former vehicle, an old beat up 1972 Datsun 240Z, a car that was definitely not made for sexual encounters. And they'd made it work and work well. He'd driven her to three orgasms before the nipping at her flesh by mosquitoes had finally drawn their fun to a close. It was a night she would never forget, both for the pleasure and the little bumps all over her ass and legs the next day.

Nyland sighed, saying, "I love this place."

"Me, too," Pamela said, moving over close to him. She took his arm and pulled it around her, laying his hand on her shoulder. She ordered softly, "Keep me warm. It's cold."

They stood there together and waited in the deepening cold until the sun had reached the horizon, finally sinking behind it. Pamela would have been happy to stand right there until the night sky had gone totally dark, and the stars had come out, but the temperature plummeted rapidly, and she just couldn't take it anymore.

She turned and hurried for the minivan, turning over the key and turning the heat to full before Nyland had even retaken his seat. If he reached for the gear shift, she would reach for his hand and stop him. Either way, she would tell him, "I know you said that I don't have to ... you know ... to have you take me to dinner. But ... what if I wanted to ... you know..."

She smiled wide, reached to her bosom, and let a button free to ensure that he knew what you know meant as she finished, "...just 'cause I wanted you?"

 

[TiredFingers]

Nyland watched Pamela unfasten the topmost of her fastened blouse buttons as she hinted at the reason for doing to. She asked if they could have sex, "...just 'cause I wanted you?"

A smile widened his lips as he looked to her bosom, then looked back up. He'd hoped that maybe Pamela might be interested in fooling around, but if she hadn't been, he would have been okay with that, too. But he'd been serious when he'd told her that dinner hadn't been dependent upon her providing service to his cock.

He looked to the middle seat of Ginger's minivan, then back to Pamela. He joked, "It's a little roomier than your Datsun was."

Laughing, he turned and squeezed between the two seats to get to the next one back. He used his toes to push off his shoes, then quickly unfastened his belt and pants and pushed them down his legs and past his socked feet. Nyland didn't see any reason for wasting time with romance or seduction as they both knew exactly what they wanted.

 

[CutiePie1997]

"It's a little roomier than your Datsun was," Nyland said about Ginger's minivan.

Pamela watched the man hurriedly move back to the middle seat. As he was undressing there, she was doing the same up front. she lost her shoes, her pants, her blouse, her bra, her panties. By the time she herself headed into the van's middle section, Pamela was wearing nothing more than a pair of socks and a smile.

She reached down into Nyland's groin, clutched his cock, and stroked it until it was the rock-hard piece of meat she'd loved riding back in the day. She put the condom package she'd pulled from her pocket earlier in between her teeth and ripped it open. A moment later, using skilled fingers, she had it unrolled down the length of Nyland's cock.

"I've missed you," she told him as she moved up into his lap. She grasped the back of the seat and pulled herself closer to him, commanding, "Put me in you."

A moment later, she was lowering herself upon his cock, letting out a great gasp of delight at the feel of his thickness penetrating her. Pamela had been with a lot of men over a lot of years, but none of them had filled her up the way The Khan had. He had by far the most girthy cock ever to enter her, something that in all honesty she had actually missed since they'd gone their separate ways.

As she began bouncing in his lap, Pamela knew it would be long before she cried out in ecstasy.

 

[TiredFingers]

Nyland laughed at the sight of Pamela coming from the front seat to the middle one in nothing more than a pair of socks. She wasn't the most beautiful or sexiest woman he'd ever seen naked. She carried a few more pounds than the fashion magazines and TikTok videos said a woman of her height should be. And sure, her tits sagged a bit. And no, her belly wasn't the flattest or her waist a magnificent hourglass.

But she was still looked good, and it was an absolute joy seeing her crawl into his lap naked, reaching for his cock and wrapping it with a condom. She told him, "I've missed you."

"I've missed you, too," Nyland returned, grasping her face in his hands and kissing her passionately. She told him, "Put me in you."

"Anything you want," he responded obediently. He grasped her hips, maneuvered each of them, and found her hole with a Look, mom, no hands skill. A moment later, she lowered at the same time that he thrusted upwards. Pamela gasped as half of Nyland's thick cock rammed inside of her.

He didn't have the longest cock in the world, just a bit more than the 5.3 inch average that the internet claimed adult males enjoyed. But his girth measured two and a half inches across. That was diameter, equating to a circumference of more than his length. He'd had women in the past ask him to stop after he'd put the whole monster thickness in them. He'd even had one laugh and declare, You ain't putting that thing in me, fuck!

But Pamela had always like it, and now as they started fucking hard and fast, his thickness quickly had her crying out in joy. It had been a while since he'd last been inside a woman, so unfortunately it wasn't long before he grunted out loudly as his balls began filling the condom. He didn't stop helping Pamela up and down in his lap, though, until she finally gave the audible and visual cues of having enjoyed her own orgasm.

Nyland pulled her against him, enjoying the heat of her against him. They simply remained there for the longest time, feeling each other's heart beats, listening to each other's deep breathing. He caressed his hands up and down her backside, from neck to ass cheeks.

"That was incredible," he told her. He moved her upper half back, kissed her, caressed and softly groped a tit, and told her with a sincere voice, "I wish we were still lovers sometimes. I ... I know why it fell apart, though."

The two of them had had two issues between them: his lack of productive employment to support them, and her addiction to illicit drugs. Until they found a way to get pass both of these issues, they'd never be a couple again.

"We should go, before the Sheriff comes and tickets us and confiscate Ginger's car," Nyland said. He helped Pamela out of lap, pulled a tissue from the box in a pocket on the back of the driver's seat, and reached to pull the condom from his slowly shriking cock. His eyes suddenly swelled, and he groaned, "Oh, fuck."

When Pamela looked to him, Nyland pulled the broken condom from his cock, showed the dripping thing to her, and asked, "Where are you in your cycle?"

 

[CutiePie1997]

Pamela kept bouncing in Nyland's lap after he'd cum, orgasming herself less than a minute later, as he was still coming down from his peak. She collapsed into him, enjoying the moment.

"That was incredible," he told her. "I wish we were still lovers sometimes. I ... I know why it fell apart, though."

She knew the issues too: his unemployment, her drug use. She returned the compliment, "It was great. Thanks. You do things for me no one else can, Khan."

"We should go," he said, "before the Sheriff comes and tickets us and confiscate Ginger's car."

Pamela reluctantly dismounted Nyland's cock and pulled some of the tissues to wipe up the mess coming out of her pussy. Then, Nyland groaned, "Oh, fuck."

She looked to his face, then to the hand holding up the condom. One look, even in just the moonlight, told her that it had broken. He asked, "Where are you in your cycle?"

"Not where you would prefer I was," she told him. She thought for a moment, saying, "Don't worry about it. I'll get Plan B."

She cleaned up and dressed, her mind on how fucked up her life would be with a baby. "We should go, like you said."

 

[TiredFingers]

"Don't worry about it," Pamela said when they realized that Nyland's little swimmers were probably engaged in the water portion of the Ironman in a race to get to the finish line: her egg. She told him, "I'll get Plan B."

"I'll pay for it," he said without hesitation. He had no idea how much it was, but it had to be cheaper than raising a kid, right?

Pamela responded to his offer, then said, "We should go, like you said."

Nyland dressed, hopped back into the front seat, and headed back down for the park's exit. He got them out the gate, closed it behind them with the broken lock, and headed them back toward the Northend. When they stopped in front of Pamela's trailer, they settled on whether Nyland would drive to Magnus or Carlson Creek in the morning to get what she needed or whether she would do it herself.

"I'm sorry this happened," Nyland told her with a sincere tone. "I had fun tonight. I've always had fun with you. I'm sorry again, that it ended this way."

If there was nothing more to discuss, Nyland would return Ginger's minivan to its spot, and put the keys where she'd told him to hide them. If there was more to discuss, he'd stick around.

 

[TiredFingers]

OOC: Okay, so for the current writers and any readers we have, two things:

• First, we lost CutiePie1997, due to a computer malfunction. (It's nipple was revealed. That's a Janet Jackson reference for you readers who are too young and shouldn't be reading Literotica anyway. ) So, Pamela will become a secondary NPC-like character shared by Alice2015 and myself from this point forward.
• Second, this post ends this 1x1 side thread. We take you back to where we left the main thread so that you restart reading there where you left off, right here.