Old Man's Last Hurrah (WritesNaughtyStories & JP500)

[jp500]

Old Man's Last Hurrah

• Roleplay between: @jp500 and @WritesNaughtyStories
• Synopsis: This is a roleplay that explores a sexual encounter between an older man and younger woman.
• Original Description: https://ecchidreams.com/roleplayer-services/private-roleplayers-bulletin/old-mans-last-hurrah-r2063/

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

Lily finished her last yoga class for the day, chatting casually with her students as she cleaned up the studio for the night. She stood as tall as many men, and her red hair was tied into a loose ponytail to keep it out of her eyes while teaching. Lily was wearing a sports bra and yoga pants which revealed more than they covered, but Jen hardly noticed - she worked with bodies all day was used to her students watching her. Her body was well toned from her yoga practice and living mindfully.

Putting on an oversized sweater, Lily left the studio and headed to the local café where she liked to go to relax. The café was used as a local hangout for the residents who came to chat, read, play games, and socialize. It mostly attracted a younger crowd, but people of all ages visited. The café was small but cozy with a couch, lounge chair, a few tables, and a bookshelf filled with books and board games. Jen would often cuddle up in the lounge chair with a cup of hot tea, letting herself relax and let go of the day's stresses.

Lily knew most of the locals who came to the café and always had a smile and a few kind words for them. Lately she'd been chatting with Jack, an older man whom she had met. He had taken to walking with her on her way home and his kindness warmed her heart.

Lily walked into the café, smiling and waving at the couple people that greeted her.

Edited July 13, 2021 by jp500
fixed character name to Lily

[WritesNaughtyStories]

Jack gave the young woman a warm smile and stood up. He leaned on his cane and pulled out the chair for Jen, gesturing her towards it. "Nice to see you, Jen. Day treat you well?" he asked, waiting for her to sit before seating himself again. He hung the silver handle of his walking stick over the arm of his chair and waved over the barista - a woman even younger than Jen, but somewhat less charming. It wasn't that she wasn't pleasant, just distant and a bit artificial.

He picked up his partially empty demitasse, "Another for me, please and," he said, turning to Jen, "for you?"

Business had been good to him and his retirement funds were barely dipped into as wise investments stayed just ahead of his moderate spending, so he treated himself to these little kindnesses for his friends.

[jp500]

"Tea please," responded Jen as she beamed a smile at the barista.

"Thank you Jack," she said as she turned her attention to him, lightly touching his arm in greeting before sitting down. "It was a busy but good day. A couple new students came in today which was nice."

"What about you? Any exciting adventures to share?" she asked lightheartedly, her eyes crinkling in a shared joke as she rested her chin in her hands.

[WritesNaughtyStories]

12 minutes ago, jp500 said:

"What about you? Any exciting adventures to share?"

The old man gave an amused grin and a slow shake of his head, "Not unless lunch and bridge with the other fogies over at the men's club counts as an adventure, no." he answered with a playful chuckle. "Have I asked you if you play?" he said, turning the conversation elsewhere.

She was every bit as smart as any of the oldesters and he could use a new partner. Her youth and stunning looks would give him an uneeded advantage over the other retirees at the mne's club, but her smile would certainly brighten the place.

[jp500]

"I never learned," she responded. "My family was big on cribbage - my grandfather taught me. I still have his old board, but haven't found anyone that plays. If you teach me bridge I'll play with you."

Lily smiled at Jack, then straitened as the barista brought their drinks and placed them on the table. Lily smiled at her as she picked up the tea and took a sip.

[WritesNaughtyStories]

Jack's dark blue eyes glinted in the low light as he gave a slight, sideways nod. "The grumpy old bastards are going to say I'm cheating by having you as a partner, you know." He shook his head, "It'll do us all a lot of good to look at something other than our own tired, old faces." He finished with a chuckle and he sipped his espresso.

"The rules are simple enough but it's the language of bidding that's the mark of a true master." He began, losing himself for a moment in the lifelong companion of a subtle, competitive and challenging game. He shook it off quickly, "Another time. I'll grab a pack of cards tomorrow, and if you're still interested I'll teach you."

He set his cup down and patted the table, "But what about you? There must have been some fun adventure at the yoga studio today." He remembered his own decade long flirtation with yoga in the 60's and 70's. He envied her in a way - now she was healthy and flexible, it had been more of a lifestyle choice in '69. He shook off the idle thoughts and gave her a grin, "Hard to believe a yoga instructor is viable employment these days. Glad to see we're making at least a little progress."

[jp500]

"Oh, I do alright," she said, smiling at Jack. "It's seasonal. First few months of the year get busy, but by summer it dries up. I've got enough regulars, and between teaching certifications and renting rooms I can manage the slower times. It's mostly the same routine each day. A couple morning classes, a lunch class, then a couple evening classes. Sometimes I have 20 people show up, sometimes only one or two."

Lily sipped her tea as she thought about Jack doing yoga before she had been born. "You should stop by sometime. Even if you don't join a class, I'd love to see you there. In any case, I'll help you swindle the other players at bridge. You can teach me some tricks and I'll be your secret weapon. I'll even bat my eyes and play innocent."

Lily bats her eyes at Jack, an innocent expression on her face. 

[WritesNaughtyStories]

Jack thought brieflly about stopping by Lily's studio, "Maybe - I can't imagine your students would be too fond of a stuff old man leering at the while they exercised. Guess I'll have to find my Jack LaLanne pants and join a class."

At the mention of swindling the other club members jack laughed aloud, "Hardly necessary. I've beaten them for years with all but the worst partners." He reached in a pocket and retrieved a silver lighter and laid it on the table, "Here's the stakes." He slid it across the table to her. It was unremarkable, a sterling, flip top lighter emblazoned with the club logo. "A new one every year. I have 20 of them or something. It used to be a little cup - like a trophy but some braggart wanted something he could show off around the club, so these are the thing now." He shook his head.

"You just bat your eyes because you're beautiful when you do. That's reason enough." He laughed. He pointed at her tea cup as he reached for the lighter, "Another? Or shall I walk you home?"

[jp500]

Lily laughed lightly at being called beautiful and smiled at Jack. "Home, thank you." 

She stood up, pushing the chair in, then took Jack's arm as they walked out of the café and down the street. She felt comfortable holding his arm as they walked and enjoyed his company. She thought about how nice Jack was to her, and how easy it was to be in his company. He was honest, and that was a rare thing to see. She met many people who put on facades, or tried to be something they weren't. For the most part she didn't mind, everyone walked their own path, but it was refreshing to be around someone that was genuine.

Edited July 13, 2021 by jp500
spelling correction

[WritesNaughtyStories]

Walking with Lily on his arm transported Jack to another time. He was half his age, his beard longer, darker, trimmed less frequently and his gait strong and certain. He looked over and smiled at Lily, "This may, in fact be my favorite part of the day." he said cheerily.

She reminded Jack of no-one, which, after 70 odd years was a refreshing change. His own kids were older than her. Hell, he had grandchildren closer to her age than his kids were. This was nice though, when he looked at them, he saw his wife, their parents, himself and the hundreds of faces that occupied their lives. Lily lived beyond that. His memories were a palace, but one he knew well and had walked the halls of for most of a century.

Lily was a glimpse beyond that. Into a countryside related to his own, but filled with awe at its difference.

Jack glanced at her again, "How is it I'm so lucky as to make this walk so often? There must be some boyfriend - girlfriend, maybe? who would be nearly as thrilled to walk with you?"

[jp500]

"Only you my darling man," Lily said teasingly as she grinned at him, hugged his arm a bit tighter. "When I was younger, I always thought that if the right person entered my life, I'd recognize them. Prince charming or my heroic knight. I had boyfriends, I cared for them, wanted to see them be happy, but love?" She shook her head in the darkness. "I don't think I ever knew what that was. I've dated women too, but it was the same. I enjoyed our time together, but it never quite worked out. "

Lily smiled at Jack and thought about it as they continued to walk down the street. "And now I'm busy with the studio. I meet people everyday and I feel the same compassion towards them as I did towards those I dated.  I used to wonder if something was wrong with me, but now I just accept it. Life is living in the moment, enjoying what is in front of you."

As they reached her apartment, she realized that she did not want the evening to end. She turned to Jack and lightly placed her hand on his chest while still holding his arm.

"Would you join me tonight Jack? For the night?" she asked as she looked into his eyes. "I'd like your company."

[WritesNaughtyStories]

As Lily explained her position on people and relationships, Jack listened quietly. Her experience was very different from hers. He'd met his wife in grade school, they'd dated through middle and high school, married almost right after college. Part of it was that was what was expected, but part of it had been love. When cancer had killed his wife - almost Lily's entire life ago - Jack had been devastated. In time he'd recovered. He'd tried to date but it had always ended much the way Lily's experiences had.

When she'd finished, Jack pursed his lips and took a few steps before he spoke, "You seem happy and content. There's no reason to clutter that if you don't need to. I tried to date a bit after my wife died, but I ended up feeling largely the same way you do."

He looked up and pointed with his walking stick - it made him feel much less elderly and much more distinguished, if he thought of it as a walking stick rather than a cane - "Here we are, home again, home again, jiggedy-jog."

Jack cocked his head to one side and gave Lily a slightly puzzled look. He thought for a second, unsure what the invitation entailed but quickly smiled and nodded, "It would be my great pleasure." The older gentleman replied, inclining his head politely.

He followed Lily in, heart racing in a way it hadn't in years, "This is, I think, a first for me." He said with a friendly smile, "Other than my father-in-law's place and my wife's sorority, I don't think I've ever been invited into a woman's house - I confess I have absolutely no idea what to do," He gave a broad, playful grin, "Unless you want to threaten me about your honor or have me tap a keg - those I know."

 

[jp500]

Lily smiled at Jack, then leaned into him, gently touched his lips with hers. She didn't linger, but stepped away and began walking in front of him, guided him to her front door. She felt sexually energy tingling under her skin as she walked in front of him, one hand stretched behind her holding his hand. She wiggled her butt playfully, the sheer yoga pants and low light not hiding how well toned it was. She gave him a glance over her shoulder that she hoped was mischievous.

She paused at the door, getting the keys, then opened it.

[WritesNaughtyStories]

The kiss was so sudden and brief that Jack half thought he'd imagined it. As Lily walked ahead to the door, clearly sashaying for his benefit the slight doubt vanished. He held his walking stick in front of him and folded both hands over the handle as he looked at Lily and tried to decide what was happening. A part of him knew, but quite a bit more of him assumed he'd misinterpreted something. He looked at the back of his hands and felt a little tremble of excitement.

When Lily pushed the door open Jack tapped his cane once, pulled himself to what remained of his height and followed her. "Here's hoping this is far less disappointing for you than I'm afraid." He said with a playful chuckle as he followed her in.

[jp500]

She closed the door behind them, then turned to Jack. She placed a hand on his chest while her other brushed his tie and looked him in the eyes. 

"It doesn't matter," she said as she kissed him again. She lingered a bit longer, tasting his lips, offering hers to him.

"There's only this moment, here, with me," she whispered to his lips. She wrapped an arm under his jacket, placing a hand on his back as she kissed him again, pulling her body into his. 

Lily was in the moment, being with this man. His scent filled her, and she enjoyed the feeling of her body pressed up against his.

[WritesNaughtyStories]

Jack gave Lily a slight nod and smile to say,  'Touché.' and wrapped one arm around her as she kissed him again. This time he was better prepared and returned the kiss eagerly, enjoying her full, soft lips.

1 hour ago, jp500 said:

"There's only this moment, here, with me,"

"Well, let's enjoy it then, shall we?" he replied with a little more confidence than he felt. She was so much younger than he was and he was so far out of practice. But he held her close, enjoying the press of her feminine form and the scent of her. He raised his hand from her back to brush the hair away from her face. His bright eyes locked on hers and he burned her face into his brain. "You are certainly a beautiful woman, Lily." He leaned on his cane and bent to kiss her again, letting his hand fall to her firm, shapely behind.

He gave tit a playful squeeze and lifted his face from hers, "My - that's quite an ass young lady, do you, by chance, practice yoga?"

[jp500]

Wiggling her butt she said in her most seductive voice, "You'll find out soon." Lily rested her head on his chest, feeling happy.

"Come," she said, breaking away from Jack and guiding him further into the apartment. "I don't have much to drink - water and tea mostly - would you like some?" She pulled off her sweater, placing it with her purse and keys on the table. She seemed to be bouncing around with youthful energy. Wearing a sports bra and yoga pants, she returned to Jack.

"Here, let me take your coat," she said, smiling at Jack as she gently pulled at his tie, trying to see how to undo it. Taking off a man's tie was not something she knew how to do.

[WritesNaughtyStories]

Jack was content to feel Lily wiggle against him, the pressure of her belly against his crotch stirring his aging manhood from a long slumber. When she broke a way he let her go reluctantly but followed, wondering if he'd even be able to get hard. He pushed the thought aside and answered, "Water is fine."

As she lifted her sweater over her head Jack felt himself draw in a surprised breath. Her narrow waist and flat belly rose above her rounded hips, sheathed in the dark, form fitting yoga pants, was a sight he'd never thought of seeing. Her fit body, clothed in form-fitting Lycra® sent him spinning back 50 years or more.

"You look fabulous." Jack said, accepting the drink with an outstretched hand. As she again pressed close, Jack set the glass on a coaster. He unbuttoned his jacket and slipped one arm out of the sleeve before switching the cane to the free hand and shaking off the suit jacket.

As Lily fumbled with the tie Jack fold his hand over hers softly. "Like this." He said, sliding the knot all the way down the back end of the tie. As it slipped free, he gave the knot a tug and it came undone. "There." He said, dropping it on top of her sweater. He leaned the cane against the door frame and pulled Lily close, caressing the bare skin of her back as he did.

Let's hope this is like riding a bicycle." he said, bending to kiss her deeply.

[jp500]

Lily kissed Jack with gentle intensity, her lips tasting him, her tongue teasing. Her arms wrapped around his head as he caressed the bare skin of her back. She leaned her body into his, basking in his warmth, and let her breasts brush against him. Her nipples hardened and she let out a soft sigh. "Take me to the bedroom," she whispered as she continued to kiss his lips and his hand dropped to her ass. A momentary feeling of nervousness swept through her as she whispered the words, but her desire was strong and she wanted to feel this man against her bare skin. She could feel his fingers flexing against the sheer fabric of her pants and she let out another soft sigh of pleasure. A momentary feeling of nervousness swept through her as she whispered the words, but her desire was strong and she wanted to feel this man against her bare skin.

[WritesNaughtyStories]

18 hours ago, jp500 said:

"Take me to the bedroom,"

Jack's breath caught a little at the request. This was, indeed, going where he thought it was and he was both excited and terrified. Lily had probably been in middle school the last time he'd been with a woman. Hell, she'd probably been in college the last time he jerked off more than twice a year.

He swallowed his fear and smiled, "With pleasure." he heard himself say as he pivoted around her and retrieved his walking stick. With his arm wrapped around her waist he pointed down the hall to where he expected the bedroom was. "This way?" He asked and began to walk that way.

He pulled her close as he walked and let his hand explore the feminine curve of her hip as they walked.

[jp500]

Lily's body buzzed with anticipation. Her skin tingled as Jack's hand explored her hip and ass. She was breathing harder and her body felt... desire. need. want. 

As they entered the bedroom, Lily gently pushed Jack to sit on the edge of the bed, then took a step back. Looking at him, she pulled off her pants and panties, then removed her bra. She stood naked in front of Jack, giving him the opportunity to see her fully. Her skin was pale but with the sheen of youthful health. Light tan lines highlighted her small breasts with their nipples erect. Her abs and ass were well toned. Between her legs, her labia extended through a trimmed patch of pubic hair. 

She smiled at Jack, giving him a few poses before approaching the bed. She tried to straddle Jack by sitting on his lap, but they stumbled and she lost her balance. She laughed and swept her legs onto the bed, sitting only inches from Jack, her body facing the side of his. 

Touching his shoulder she asked, "How do you want me Jack?" A glitter of amusement sparkled in her eyes as her other hand touched his thigh.

[WritesNaughtyStories]

Jack leaned back on his hands and watched the impossibly attractive young woman undress. He'd have never imagined he'd be faced with such a beauty, much less so late in life. Not one to be anything but thankful, Jack's dark blue eyes twinkled under his white eyebrows as he enjoyed the show.

His breath was coming quickly and he could feel his old prick swelling further. He was pretty certain he would not be able to muster a full erection, but he was comforted to know he wasn't completely dead yet. At the sight of her bare breasts and stiff nipples, Jack drew in another excited breath and gave a soft moan of anticipation. He wanted to feel the firm, sensitive flesh between his lips, feel her move with pleasure in reaction, hear her sigh softly.

When her underwear came away and he caught sight of her flushed labia peeking out between her sculpted thighs and her dainty pubic triangle the old man sat up, pushing himself up with one arm, and took her bare, slender waist in both hands and guided her towards him.  He bent to draw her erect nipple into his mouth as she moved to straddle him and the couple tumbled to the side.

As she sat up on the bed beside him she asked, "How do you want me Jack?". He lay on his side, looking up at her over her crossed legs and smiled. "Just like that." He answered, pushing her back toward her pillows. He swung his legs around and rolled over. Prone in front of her folded legs, Jack lifted one ankle and pushed it to the side, then urged the other open and wormed his way forward, breathing deeply the scent of her arousal. The delicate pink folds nestled between her legs drew him forward and he brushed them gently with one finger. "Best not rush the old man," he chuckled, planting a kiss at the top of her sex, "who knows what the recovery time is these days."

[jp500]

Lily inhaled with delight as Jack's mouth touched her sex, his beard brushing against her inner thighs. She lifted her knees and spread them wider while lifting her pelvis, resting her feet to the sides to give him better access. Her hands went to his head where she gently ran her fingers through his gray and white hair. It lacked the silkiness she was used to, being stiffer and rougher. She liked how it felt in her fingers and she looked forward to feeling his beard on the rest of her skin.  She smiled at Jack as he started pleasuring her with his mouth.

Edited July 15, 2021 by jp500

[WritesNaughtyStories]

Jack inhaled deeply, relishing the rich, feminine scent of Lily's musk as he gently used his finger to roll one of her lower lips to the side. He pressed his tongue forward at the base of her slippery slit and licked all the way up, shivering with his own arousal as the taste of her filled his awareness. He felt his teeth slip and pressed his lips to the hooded pearl the crowned her dewy, pink flower.

He gazed up over her neatly trimmed pubic hair and saw her smiling back. He gave her a wink, "Least sexy thing ever." he said, smiling as he reached up and pulled his teeth out. He dropped them carelessly to the floor and bent his lowered his lips to Lily's soft sex.

He resumed lapping hungrily at her deliciously aroused cunt as he slid two fingers inside her. He thrust slowly at first as his tongue worked its way from top to bottom and back. He pressed her labia gently between his gums and slurped hungrily at the soft folds before resuming laving her soft, sensitive flesh with his surprisingly agile tongue.

[jp500]

Lily was shocked as Jack removed his dentures, but the feeling of his open mouth and gums was quite nice. Then his fingers penetrated her, and any lingering unease drifted away.  His mouth felt wonderful as he lapped and teased at her, and she couldn't help but think that this was a secret pleasure hidden away by those in the know. I should have discovered this sooner, she thought in wonderment as she let her head fall to the pillow and her back arch, her pussy hungry for more.

As his tongue pleasured her, she grasped her breasts and teased her nipples. Her fingertips left indents in the skin where they dug into the soft flesh of her breast. The start of an orgasm began rocking through her body and she let out a soft moan, almost a whimper. Her hips rocked and he held them firmly under his control. She knew it wouldn't be the last she felt this night. He was good.