Windy and Warm

Story Info
A busker meets a homeless woman.
3.1k words
4.64
48k
56
14
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
riverboy
riverboy
4,576 Followers

A young musician named Rich left his shabby, low-rent apartment at dusk with a beat up guitar case. He climbed into his rusty old Chevy van, and the tired engine sprung to life, making a racket and vibrating badly. Rich shook his head waiting for some of the noise to go away when the oil warmed up a bit. He knew the engine was running on borrowed time.

He drove from the neighborhood he lived in — made up of paint pealing duplexes mixed with a few boarded up crack-houses — to a hip, rejuvenated part of downtown, where the streets were lined with the latest restaurants, good bars, and trendy boutiques. The old van rattled and banged over pot-holes — an old blanket he had hung from the ceiling behind the seats to keep the heat in the cab in the winter did little to tone down the road noise echoing around the back cargo space.

He drove a van because he was the leader of a rock band that played bars on the weekends and a few weeknights. He and the boys needed it to haul their gear around to the gigs, but every time he drove it he dreamed of sitting behind the wheel of a sports car.

He turned a corner and crossed some ancient railroad tracks which always threatened to shake the old van to pieces, and parked the rusty white beast. It was a long walk to where he was headed, but paying for parking closer in was a non-starter on his budget. He grabbed the guitar case and walked, hoping to get a good corner to play on this warm summer night.

Rich was a busker when he had free time. He loved doing it — not only was he entertaining people and supplementing his meager income with the money people tossed in his guitar case, it was also great practice, a place to try out new songs and new techniques. He also met a lot of folks and made some connections for his regular band gig.

He was early enough on this particular evening to get a good corner — competition between buskers on warm summer nights could be fierce. He took out his old beat-up acoustic guitar, strapped it on, and settled in for a long night of playing and singing. He was a good entertainer — vital for making good money on the street — and as a small crowd gathered he told stories about the songs and some good jokes to keep everybody happy. This was a pretty good night for a Wednesday, and he made almost sixty dollars by nights end.

One of his regular audience members was a homeless woman known as Windy. She never told anyone her real name or where she was from.

Just about every time he busked, no matter where in the city, she seemed to appear, although sometimes just for a minute or two. Before he found out her name — from a soup kitchen volunteer he overheard talking to her one night — she seemed to him like a ghost... a spirit of the night. One night she was even dressed in a dirty old white wedding dress, which with her haunting tired eyes made her even more ghost-like. That night she just drifted down the street, glancing at him sideways, and disappeared around a corner.

Windy's real name is Katherine Jane Ross, and she's the daughter of a bank executive. She's thirty-six years old, and she's been homeless for five years, staying alive by instinct, with occasional help from the kindness of strangers, some friends in the homeless community, and even though she hates doing it, the local Rescue Mission when the temperature gets sub-arctic on certain winter nights. A relationship went bad when she was thirty-one, and she was left physically beaten, bruised and nearly penniless. Her man had disappeared with everything, and she couldn't face her family with the news because they had told her all along it would happen. So she left. She had just enough money for a bus ticket to New York City, and she found herself part of a large homeless community there. When some friends died in an ugly way she left the big city behind, hitchhiking her way back to the small rust-belt city she was born in, giving blow-jobs to disgusting men to get rides. When she got back here she swore she'd never touch a man again.

She lives, at least for now, in a ramshackle shelter made up of old pieces of plywood she stole from a construction site. It's held together with duct tape and old rotting rope. There are a few other homeless folks living near her — a little 'village' in the scrubby brush out behind an empty factory building, the same old building where Rich parked his van when he busked, which is how Windy first saw him. The members of her 'village' are very wary when a vehicle shows up at the derelict factory, and she had watched him when he first parked there, and followed him as he walked to his corner and pulled out his guitar and played. She had a crush on him immediately — Rich was a good looking musician after all, even if he was a little younger than her.

Windy's heart beat fast the night Rich first spoke to her. She had wanted to talk to him for a while, but the art of conversation had faded from her brain, and years of homelessness had left her a mostly silent person when she was wandering through the real world. She loved standing at the back of the crowd on a busy night, listening to his stories and his songs, and watching the way the crowd responded to him and laughed at his jokes, but getting up close was too much for her, and if it was a slow night with just a few people around she would just breeze by without stopping. She usually couldn't help herself and would do it two or three times a night, and one night she timed it wrong and he finished a song just as she was approaching. His little audience turned and walked away and it was just the two of them as she passed. She was looking at the ground and moving fast, hoping to escape, when Rich spoke up.

"Hi beautiful. How's it goin' tonight?"

She stopped dead in her tracks, looked him in the eye, and scurried off into the darkness. Around the corner she stopped and took a deep breath, surprised at how his simple words had affected her. Her heart was racing, and she was scolding herself for being an idiot, just like a teenaged girl would do.

The words 'hi beautiful' echoed in Windy's head for a week, and she kept a close eye on the trash filled parking lot where Rich parked his van. Finally, after she was sure he would never come back, the rusty white van rattled over the railroad tracks and parked. Rich got out with his guitar case and started walking toward downtown. Then he paused.

"You can walk with me you know, I won't bite," he said loudly toward the back of the parking lot.

Windy was shocked by his words. She didn't like it when people knew more about her than she wanted them to know, and a wave of anger washed over her. He walked away as she cooled down, but she didn't know quite how to handle the situation.

It was a busy weekend night. Rich didn't have a gig with his band due to a scheduling error, so he was looking forward to a good night to fill his wallet and keep gas in the van. The crowd was big and boisterous due to a big sports event that emptied onto the street, and it turned out to be the best night of busking Rich had ever had. Windy had gotten over her misplaced anger, and was enjoying herself buried deep in the back of the big group watching Rich perform when she was once again shocked by his words.

"I'd like to dedicate this next song to my biggest fan," Rich said in his loud busker voice. "She's here watching me most nights, and I just want to tell her how much I appreciate her and that I wish her all the best in life. Life's short, and we need to enjoy each others company. She's a pretty girl, so, this one's for her."

He looked right at Windy through a gap in the crowd and smiled as he started singing the old pop song from the sixties "I'm a girl watcher," and the boisterous crowd sang along. He had thought about singing the old chestnut "Windy," but thought she'd be uncomfortable being called-out so specifically. As Rich sang she smiled and bit her lip, and tears welled in her tired eyes. It was the highest moment of happy emotion she'd felt in years, and she snuck away when the song ended during the applause.

———————

"Thank you... for the song," Windy said, startling Rich as he walked passed the dark empty factory back to his van at the end on the night. She was sitting on the ground, leaning back against a graffiti covered brick wall in the dark, barely lit by a crescent moon.

"Hey!" Rich said with a big smile. "How's it goin' tonight?"

Rich sat down with her, happy to finally get to know this mysterious woman. They talked like old friends — easy, flowing conversation that Windy didn't even realize she was capable of. She told him about the long, wild hair she used to have that gave her nickname, the struggles to keep warm in the winter, the pleasures of warm food, the homeless friends she had made, and the joy his music brought her. Rich took out his guitar and played for - he played "Windy" this time - and it was so wonderful she laughed. She laughed! It was the first time in...well... forever it seemed. She had chuckled at her friends jokes, but a real live laugh — that was new and special, and Rich could sense it.

"What do you say we go get some breakfast," Rich said as the night wore on. "I hit the jackpot tonight with that big crowd. I'm buying."

Windy was reluctant — she hadn't been anywhere to eat other than a soup kitchen for years, and she was sure she smelled bad and looked worse. But she couldn't say no to the charming Rich, and with some trepidation she climbed into his van and they went to an all night diner. Windy led them to a corner booth way in the back, and they feasted on big omelets stuffed with vegetables and cheese, home fries, fresh fruit, coffee, fruit juice, chocolate milk... the works. The sixty-year-old waitress was a gem, and she made Windy feel right at home. The eastern sky was brightening when they got in the van and it rumbled to life.

"You know," Rich said, "I only live about two miles from here. It's a shitty apartment, but it's got a good shower and a soft bed."

Windy was overcome with emotion she didn't know what to do with.

"You don't want me..." she said quietly, her voice trailing off.

"I wouldn't have offered if I didn't," Rich said.

"Maybe just a shower," Windy said after a long pause, looking deep into Rich's soft blue eyes.

———————

Windy emerged from Rich's worn out old bathroom wearing a terrycloth bathrobe Rich's mother had given him for Christmas. She was toweling off her wet hair, and trying to make sense of all the conflicting emotions rattling around in her head.

"You know that old saying 'you clean up nice'? It's usually just a cliche, but in this case it really fits," Rich laughed.

"Ha!" Windy said. "I bet you have no idea how good that shower felt. Have you ever been dirty for months at a time?"

"I love being dirty," Rich said with a wink.

"I'm not the girl for you Rich," Windy said. She was secretly hoping he wouldn't buy it, and sexual urges were welling up in her in a way that surprised her. "I'm a mess. You don't need me in your life."

"This isn't about need, this is about want. Do you have any idea how attractive you are?" Rich said as he walked toward her, and he kissed her.

Windy's head just about exploded. The man of her dreams had his warm lips pressed against hers, his soft tongue delicately beginning an exploration of her mouth, and a growing bulge in his pants pressed against her body. What was happening? How did she get here? And why did she care? Just go with it, she told herself, and her tongue slid into Rich's mouth as her arms encircled him.

Rich's strong arms felt good holding her, and she reveled in the sensuality of his kiss. He deftly flicked the tie and Windy's robe opened as his hands slid down to her ass and he pulled her tight against him. The feeling of his rock hard bulge against her warm, clean pussy sent her head spinning wildly, and her hands started groping, searching for things she had long ago decided she didn't want to find. How can one simple man change me so completely, she thought. And then, when her hand felt the heat radiating through the crotch of his faded jeans, she decided to not think anymore, just do.

She dropped her robe and helped him quickly strip, and they tumbled into bed. The softness of it astonished her, and she moaned just from the feeling of the mattress and sheet beneath her naked body. The luxurious feeling was amplified when Rich started kissing every inch of her body, his warm hands sliding ever so softly over her, leaving a trail of goosebumps behind.

"You're gonna drive me wild!" she said as she lay spread-eagle with eyes closed, and quiet moaning laughter burbled from her smiling mouth.

Rich felt the electricity coming off her goosebump covered skin, and heat radiated into the palms of his hands and his lips. His kisses reached her tits — lovely large orbs oozing slightly off the sides of her chest, heaving with her sharp breaths. He licked her nipple and she groaned, and then he took the firm rubberiness of its tip between his teeth and sucked it in. It tasted clean and sweet, and Windy whimpered as her body writhed on the soft bed.

As Rich suckled her tits his hand roamed, and soon it found the soft bushy hair hiding her prize. She was a natural blonde, and hadn't shaved in years, and his hand explored the thick bush and down onto the top of her inner thighs. Her legs spread at his touch, and he was astonished at the amount of pure heat radiating off of her.

Rich wasted no time kissing his way down her body, and his tongue lapped up the glistening moisture on Windy's pussy lips. He slid his tongue inside and her freshly cleaned pussy, perfumed with his soap, tasted sweeter than honey.

"Oh God!" Windy yelled out when he had his whole mouth on her, suckling the lips and folds and gently rubbing her clit with his upper lip.

Her hands were back above her head, clinging to the tarnished brass headboard. Windy had never felt sexual stimulation like this before. Her sex life, back when she had one, was nothing special, and these sensations with Rich were better than anything she could ever have imagined. She lay there thinking, 'yes, now I know what all the fuss is about. Sex really can be mind-blowing.'

While her mind was spinning out of control Rich had positioned himself between her legs and was looking at her lovingly.

"I'm clean," Windy said, wondering if he had paused thinking about disease or some such thing.

Rich shook his head. "You're perfect," he said, and he pushed his steel hard cock into her.

Windy's hands came off the headboard and slapped down hard on the sides of the mattress, clutching at the sheets. Her back arched and she let out a wail as he entered her. She felt Rich's cock slide in, and then pull out. There was a slight pause and she almost screamed at him to ram it home, but then she felt it slide in again, deep this time, filling her with warmth and energy, nearly nuclear in its power. Her head was up off the bed, looking deep into Rich's eyes, her mouth open, breathing hard. Her chest heaved high with each thrust of his cock, until instinct took over and their bodies melded together into a single rocking entity. Windy's eyes rolled back in her head and she was flying. She flew through blackness and into bright light, feeling simultaneously like a feather on the breeze and a bullet rocketing through space. She exhaled sharply three times, with quick deep breaths between, the sensation building quickly, and the forth time she lost her mind. It flew out of her head, bounced off the walls like a rubber ball, and oozed back in through her scull, just in time. At least that's what it felt like to her.

Rich was overtaken by a feeling of rightness. That feeling you get when whatever it is 'out there' aligns. The incredible heat of Windy's pussy as he entered her, the look on her sweet face as she felt him deep inside, the way their bodies joined together in perfect motion, and the deep orgasm Windy obviously felt at the exact time his head was lost in the ether — there was a rightness about it all. He pulled out at the last minute and came hard. Ribbons of hot semen splashed on Windy's belly, and both of them moaned deeply.

The whole night felt right to him — sitting in the dark at the old factory with Windy, eating and laughing at the diner. He knew he was hooked deep, and hoped she was too.

"You know you're not homeless anymore, right?" he said to her. "This is your bed now."

Windy smiled, and with tears in her eyes she rolled her sticky body over on top of him, and she kissed the soft sheets. "This is my bed," she said, and she kissed Rich. "And this is my man."

riverboy
riverboy
4,576 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
14 Comments
woodrangewoodrange5 months ago

njce simple feel good story.really enjoyed it thank you

wmjm54wmjm545 months ago

Nice heartwarming story. Thanks.

Rancher46Rancher46about 2 years ago

Lovely story but was two short in duration as it needed more. A second chapter would be nice.

Diecast1Diecast1about 2 years ago

Lovely story. Thank you. AAAAAA++++++

TSreaderTSreaderabout 8 years ago
Very sweet!

And so many possibilities with this story!

Show More
Share this Story

Similar Stories

Irish Eyes His love was betrayed, what next.in Romance
Sales Team Desperate woman tries to pay back man who saves her.in Romance
Charity Begins Next Door Life isn't fair. So when you fight back, fight dirty.in Romance
Aiding and Abetting The good guys don't always finish last.in Romance
Hero's Reward One brave deed holds the key to unlocking a scarred heart.in Romance
More Stories