Every Little Bit Helps

Jack tried not to grimace as he took the sheaf of letters which seemed to always be mostly bills out of his mailbox cubby and found that today all the letters were bills, most of them marked as late or overdue.

"Hello Jack," Linda, an older woman who had the apartment below Jack's that he'd been on friendly terms with since he had moved in said as she walked up, "How are you doing?"

"Oh, I'm fine," Jack lied smoothly with a smile before tipping the letters in his hand with their red scarlet stamps of OVERDUE up to his chest when he saw Linda's eyes glance down.

"I had heard that the Portland Grill had closed," Linda said with a sympathetic smile, "I hope you were able to find something to get by."

Jack adjusted his mask unconsciously while he gave a shrug, "I've been running deliveries on my bike around town," Jack replied, "It's not what I made, but every little bit helps as long as they don't shut down takeout orders as well."

Linda nodded and opened her own cubby to pull out what looked to be two or three junk mail flyers before snapping it closed.

"Well, if you ever need a little extra money I'm sure I could find something for you to do," Linda said with a smile.

Jack laughed and shook his head, "I don't think twenty dollars to mow the grass would do much anymore, and besides the apartment complex keeps the grass mowed anyway."

"I guess they do, don't they," Linda replied and then gave Jack an odd, intense look, "But I still think I could find something that you could take care of for a bit more than twenty dollars.

"I might be able to go as much as thirty!"

"I'll keep that in mind, Mrs. Samuels," Jack said with another laugh and friendly nod before starting back to his apartment.

An hour later he was still sitting at his kitchen table going through all the bills again for the tenth time. He was already late on rent, had missed a car payment or three, and had said fuck it to his student loans almost a year ago and he still couldn't afford to get groceries this week.

As he stared down at all the bills Linda's off hand comment of finding an odd job for him to do kept resurfacing in his mind. Hell, even fifty bucks would help if it meant he could run by the grocery store, and like he had said to Linda earlier, every little bit helped.

Jack finally got up and slipped his Teva's on before walking downstairs to Linda's apartment. It was only a few moments from the time Jack knocked until Linda opened the door wearing a two piece black bathing suite and a light blue sarong coverup.

"Oh, hi Jack, you caught me just as I was getting ready to go to the pool," Linda said cheerfully.

"Hey, Mrs. Samuels," Jack said and tried not to openly stare.

Jack had noticed Linda before at the pool several times, and even though she had to be in her mid sixties she still got more than a few appreciative looks with her long, slim frame, dark brown hair that cascaded down past her shoulders, and uniform caramel tan. Even Linda's breasts were a firm C cup that Jack always suspected had more to do with modern surgery than good genetics.

"Ummm, I was actually wondering if you still might have an odd job or two for me if you were serious," Jack said after swallowing what little of his pride he still had.

"Well, first, you can start by calling me Linda," Linda replied tartly before giving Jack a more appreciative look himself, "Have you ever given massages before?"

"Massages?" jack asked in surprise, "I've... No, I've never given a massage."

"In your entire life?" Linda scoffed, "You mean you've never given a girlfriend a massage?"

"Well, yea, of course, but not a stranger," Jack replied.

"Am I a stranger?" Linda asked with a smirk.

"You know what I mean," Jack said, "And I don't think a massage would really be ok with all the Covid rules and stuff."

"I'm sure you wouldn't want to piss off Kate Brown, now would you," Linda said after looking at Jack with another smirk.

"I'm sorry, who?" Jack asked in confusion.

Linda sighed and shook her head before smiling.

"Well, Covid or not, if you want an extra job then how about you come back at two," Linda said with a smile, "I'll be back from the pool and you can give me a massage."

"I... ahhh..." Jack stammered.

"How about a hundred dollars for an hour?" Linda added, "A professional massage would cost more, but you already let it slip that you're not a professional. Who knows, It might not be too horrible a way to spend an hour for either one of us I would think."

Jack's mouth which had been hanging open in shock snapped closed at the mention of one hundred dollars. In all honesty Jack did enjoy giving massages with his past girlfriends, but that was generally because of where they tended to lead which would not be happening in this case.

"So?" Linda asked as her sarong slipped open.

Jack wasn't sure if Linda was intentionally flashing him but with her standing five foot six and his height of a little over six feet he found he had a perfect view between Linda's cleavage with her bra top bikini.

"Ahh, I think I could do that," Jack finally replied and looked up to meet Linda's twinkling eyes.

Blue eyes with a darker edge around her pupil which he had never noticed before.

"Perfect!" Linda said with a huge smile, "I can't wait!

"Don't worry about bringing anything with you, I have some booda butter that I absolutely adore," Linda added after a moment and reached out to pluck at Jack's dark gray t shirt with the Molon Labe motto emblazoned on the front, "Just do me a huge favor and take a shower first?"

"Sure, no problem," Jack said in a rush before Linda smiled up at him.

"I'll see you back here at two then," Linda said before waiving and closing the door.

Jack rushed upstairs even though he had an hour and a half before he had to be back, hastily grabbing a bite to eat before jumping in the shower. As soon as he got out he toweled off and quickly selected a pair of athletic shorts with one of his more tight fitting Under Armor shirts. He even attempted to run a comb through his scruffy mop of dirty blond hair that he hadn't bothered... or been allowed to get cut since all the rules took effect.

A quick glance in the mirror and Jack thought he was ready to start his new career as a masseuse, the last eight months of nonstop biking to deliver to go orders having slimmed him down while the extra time he got to spend working out in his apartment had filled out his chest as well.

He shook his head at the thought that there were at least a few good things that had come from being locked down. When five minutes to two arrived Jack took a final glance in the mirror and headed downstairs surprised at how nervous he was feeling.

"Well, hello," Linda said after only a second or two of Jack knocking on her door, "Come on in!"

Jack smiled at Linda who was only wearing her bikini with her hair still damp from the pool and stepped inside. A curious glance around showed that Linda's apartment was identical in layout to Jack's own, but instead of his amalgamation of mismatched furniture piled high with books and random nick knacks Linda's was clean and bright with color coordinated light tan furniture and an almost spartan look with a few decorations and hanging paintings.

"I took a little time to get things ready for you," Linda confessed as she walked towards the hallway and what Jack knew was the bedroom, "The booda butter should be nice and warm by now."

Jack kicked his Teva's off and tried not to stare at Linda's butt or the way her bikini had ridden up between her ass cheeks as she led the way down the hall and into her bedroom. The covers had already been pulled back on a queen size bed and a pleasant coconut smell filled the air. Every one of the blinds were drawn up to let in a flood of bright sunlight to shine off the white sheets that Linda had spread over the bed.

"Here's the warmer," Linda said as she indicated a heated bowl sitting on the nightstand next to the bed that was giving off the pleasant coconut aroma, "So, are we ready?"

"Whenever you'd like to start," Jack replied with a grin.

Linda smiled and then turned her back to Jack, "Untie me?"

Jack's eyes widened in surprise but after only a moment's hesitation he reached out to pull the draw on the bow knot of Linda's bikini top which she slipped off and tossed onto the floor. Linda stepped towards the bed and then untied the side of her bikini briefs which fell around her feet before she climbed up onto the bed and lay face down.

"Are you going to start?" Linda asked after several moments of Jack only staring at Linda lying naked on the bed in front of him.

Jack jumped as if he had been pinched and walked quickly over to the heated bowl to dip his fingers into the fragrant oil and then jerked his hand back in surprise. The oil wasn't hot enough to burn but was much warmer than Jack had expected. Jack cupped his hand and dipped back into the oil and then began to let it dribble from his palm onto Linda's back. Linda sighed in pleasure and moved her arms up and turned her head so that her cheek was resting on her fingertips.

"I adore a massage after sunning at the pool," Linda confessed as Jack moved his hand to let the droplets of oil land from between Linda's shoulder blades all the way down to just above the crease of her butt cheeks, "With all this silliness I haven't been able to have one in ages!"

"We all have to be careful," Jack said as he reached down and ran his hands slowly up from the small of Linda's back to her neck and then down again.

"Jack, I'm sixty eight years old," Linda said as Jack began to massage her shoulders, "I think it's a bit ridiculous to be so afraid of dying that I have to give up living the remaining few years I may have left on this earth!"

Jack bit back anything more and dipped his fingers into the hot oil before dripping it over Linda's upper arms. As he kneaded her deltoid and biceps he could better notice the signs of her age, her skin a little looser than any of his past girlfriends with a fine network of barely noticeable wrinkles. Jack worked his way back from her arms to her neck and after a few minutes down to between her shoulder blades.

"You're doing wonderfully," Linda sighed when Jack reached her lower back.

"Thank you," Jack replied as he glanced down between Linda's slightly parted legs.

Jack was surprised to see that Linda was completely shaved with her inner lips just visible between her sex, the sight causing him to feel a stir as he began to swell.

"I do like giving massages," Jack admitted as he worked his way down and began to work on each of Linda's butt cheeks, "But I've only given them to my ex girlfriends before."

"Lucky girls," Linda said softly, "Did they enjoy your hands as much as I am?"

Jack laughed and moved down to the back of Linda's legs, dribbling hot oil from her ass down to the back of her knee.

"Maybe a bit more," Jack said, "Since they were my girlfriends and I could do whatever I liked with them!"

"There's no reason to be shy, Jack," Linda said with a glance back towards him, "I have absolutely no problem with you doing whatever you like with me either."

Jack's hands froze for several moments until Linda helpfully spread her legs a little farther apart, Jack's eyes drawn up to her pussy and her inner lips which were now completely visible with her mound parted. Jack bit his lip as he stared at Linda's full, long lips, her hood still concealing her clit and let his fingers begin to knead Linda's inner thigh.

"Mmmmm," Linda sighed as she lifted her hips slightly and spread her legs just a little wider.

Jack bit his lip as he realized exactly what Linda wanted while wondering how far he should go. For a moment he wondered if this had been her idea of a little extra work the entire time before realizing that he honestly didn't care, that he was going to enjoy himself and that he was going to tease her as much as he could too.

After a quick reach down below the waist of his athletic shorts to rearrange his now full erection he massaged up Linda's inner thigh until his fingers were working her pelvic floor along the swell of her mound without ever touching her sex. Linda moaned, her hips moving slowly in time with Jack's hands until he stepped back to get more of the hot oil. He started working on Linda's other leg, kneading and massaging down to the back of her knee before slowly working up her inner thigh to her pelvic floor, his fingers working deep into her flesh along the crease of her thigh and mound while she moved her hips. After working her inner thigh Jack decided to test just how far Linda would let him go and began to use his thumbs to squeeze and massage up and down her mound before finally using just his fingertips to massage Linda's inner lips.

It took only a moment for Jack to find the hard nub of her clit beneath her hood while still gently massaging along the outside of her lips without parting them to explore further. Linda's hips were gently rocking in time with Jack's fingers and he could see the moisture that had nothing to do with the massage oil building up as well. With a wicked grin Jack dipped his fingers in the hot oil and then moved down the bed to begin massaging her calves and ankles.

"Ohhh!" Linda cried plaintively, her hips still rocking as Jack continued his massage her ankles.

After finishing both of Linda's lower legs Jack began to dribble the hot oil onto the sole of Linda's right foot, the sudden sting causing her foot to jerk a little before Jack took it in his hand.

"Do you get regular pedicures?" Jack asked as his fingers slipped between each of Linda's toes, "Your feet are beautiful and very soft."

"Mmmmm, thank you, I used to," Linda sighed, "I use a pumice stone to scrub my feet and lots of moisturizing lotion for now with everything closed down."

Jack finished Linda's right foot and repeated the entire process with her left. As Jack again massaged between each of Linda's toes she raised her right foot up so that the tips of her toes grazed his erection through the thin fabric of his shorts. Without pausing with his massage Jack moved forward enough so that Linda's toes were pressed firmly against his shaft.

"I think you might be enjoying this as much as I am," Linda sighed as she began to move her toes up and down Jack's length.

"You could say that," Jack replied and continued to work on Linda's left foot a bit longer than he had planned as she caught the waistband of his shorts with the toes of her right and tried to pull them down.

After a moment of letting her try to lower his shorts on her own Jack couldn't wait and reached down to slip his athletic shorts oer his hips so that they fell around his feet. As soon as he had himself exposed he took both of Linda's feet in his hands and guiding them down to his erection. Linda's toes flexed around his shaft as he pressed her feet together around his dick, his hips thrusting slowly between her soft, slippery soles before using his hands to spread her legs wide apart.

Jack began to massage his way up between Linda's legs again, his fingers squeezing her calves before beginning to knead her thighs. It was obvious how willing Linda was with only a glance at the moisture dripping in clear threads from her inner lips and leaving a damp spot on the sheets beneath her mound as she raised her hips up to meet him, but he still had no intention of giving her what she wanted, at least not yet.

Jack again used his thumbs to run up and down Linda's mound while squeezing them together, her juices flowing out of her body in a steady stream with the added pressure while her hips rocked with her need. As Linda's moans became more intense he even pinched and pulled her labia with his fingertips, massaging and stretching each before pulling them apart so that he could see the tinder pink flesh of her vulva.

"Ohhhh, Jack!" Linda moaned as he knelt between her legs.

Linda's hips were now raised almost a foot off the bed with her back arched, her nectar coating her lips, mound and her lower belly. Jack moved forward slightly and took his dick in hand so that he could use the tip of his glans to run gently up and down between Linda's wet folds.

"Is this what you want?" Jack asked huskily as he let his glans slip just a little inside of her vulva.

"Oh, yes," Linda moaned, her hands gripping the bed sheet on either side of her head as she moaned into the mattress, "Ohhhhh, please!"

Jack smiled and pulled out to run the tip of his dick up and down between Linda's lips again and then suddenly plunged just an inch into Linda's shaking body before pulling out once more.

"Do you think I should?" Jack asked as he rubbed the head of his dick on Linda's now exposed clit.

"Ohhhh, don't tease!" Linda moaned, "Don't fucking tease! Just plllllllease Jack, fuck me!"

Jack placed the tip of his dick against Linda's vulva and then stayed motionless until the moment he felt her thrust her hips back towards him and pulled back without letting himself slip any deeper into her body.

"You do feel good," Jack confessed, "So hot and wet."

Jack kept his dick pressed against Linda's opening, but every time she pushed back to force him inside of her he'd pull back but not quite as quickly which let his dick slip deeper into her body before he pulled away.

"Oohh, don't tease!" Linda cried out as her body trembled.

Jack reached out to take Linda's hips in his hands with his dick still pressed against her vulva and then quickly and smoothly thrust into her body until his lower stomach slapped wetly against her ass. Linda's hips bucked back as Jack held his length buried inside of her until just as suddenly pulling out of her and climbing off the bed.

"What...?" Linda asked breathlessly as her entire body trembled.

Jack reached up to pull his shirt off so that he wast as naked as Linda before smiling down at her.

"We still need to finish your massage," Jack explained, "Roll over for me."

Linda looked up while biting her lip and then finally rolled over, Jack again taken with how beautiful she was even in her sixties. As soon as Linda was settled Jack dipped his fingers into the hot oil before letting it drip onto her breasts, his fingers lingering so that droplets of the hot, stinging oil landed on each of her nipples. Linda cried out and arched her back Jack reaching down to twist and pinch both of her hard nipples before smoothing the massage oil into her soft breasts.

Jack smiled as he massaged Linda's breasts and looked up to catch her eyes.

"I thought you might have had a little help, but these are all yours, aren't they?" Jack said.

"All natural," Linda sighed while nibbling on her lower lip, "I hope you approve?"

Jack smiled and used both of his hands to squeeze and twist both of her breasts at the same time while bending down to suckle her nipples, pulling away with an audible pop.

"I love them," Jack admitted and then went back for more oil.

Jack again took his time, massaging Linda's arms and shoulders before moving down to her breasts and stomach. When Linda reached out and took his length in her hand he only moved a little closer to the side of the bed so that she had an easier time reaching him. It was Jack's turn to moan as Linda's hand stroked his length as he worked on her upper thighs, his fingers straying occasionally to stroke along the crease of her sex and her exposed labia without delving any deeper.

"That feels good, but I have to move down," Jack said apologetically when he finally had to pull away to massage Linda's lower legs and feet.

Linda only watched, her chest heaving as Jack finally finished the slow, deliberate massage of both of her legs and feet before gently spreading her legs apart.

"I want you," Linda breathed as Jack worked his way up her inner thighs, "I want you inside of me."