One last fling

sex stories

Sorry I've been away for so long. I still read the stories almost daily, but I have not been inspired to write another until now. This one is a bit different than my others but I hope you will like it. Thanks, Kind Readers for your personal messages and comments. And now, let's look in on a tired old man on the last night of his life. He's had a fairly good life but now he's alone and sick. Ask yourself…what would you do if you knew you were dying?

James' story

'What in the fuck am I doing out here?' he silently asked himself as he drove through the dark and nearly deserted streets. Then he would remember…one more good fuck and then it's time to end it. 'Damn my memory is going fast' he thought. 'I hope I find one before I completely forget what I'm doing.

James had driven to this secluded but well known part of town for one reason…pussy. He was determined to get some just one more time and if he had to pay for it so what. It wasn't like he would need money in the morning.

The big Mercedes purred quietly as he passed groups of women willing to sell their pleasures for the right price. Most all the girls looked expectantly at the classy car as it moved slowly by. One need only guess that there was a big payday inside that sweet ride. Some girls waved, others called out and a few even flashed their tits as he rolled past. As he passed each little clutch of barely dressed (and barely legal, he guessed) young girls he continually told himself, 'I'll pick up the next nice one I see. Doesn't matter if she's legal…..hell I don't care if she has HIV or AIDS. What is it gonna matter.

At nearly 64, James was alone. He had to remind himself that he had had a fairly good life. After the first failed marriage he had found the love of his life…. a keeper. He was still just twenty-three and she barely nineteen when they met and married. Cheryl had been totally devoted and they had a beautiful daughter early on. James had wanted to name her Cassandra but Cheryl was determined to give her first child a biblical name. A brief argument ensued and they decided to daughter would be called Hope. She was to be their only child. Cheryl developed ovarian cysts after Hope was born which turned malignant while she was still in her mid twenties. A total hysterectomy ended any hope for more kids but James was not upset. He doted on his precious daughter….even spoiled her or so Cheryl complained.

At sixteen Hope started to pull away from her parents as most teens do. Cheryl and James did their best to accept and understand but their efforts only caused her to rebel even more. By seventeen, Hope had dropped out of school and was deeply into drugs. On her eighteenth birthday Hope left home for good. She had taken up with a 'worthless lowlife' as James described him and the two of them had left town. Contact with her worried parents became more infrequent and eventually stopped altogether.

Just two days before his forty-fifth birthday, James received an email from his daughter. It was short, but not too sweet. She wrote that she had given birth to a baby girl. That was it. No clue as to where she was, how she was doing or even the child's name. James and Cheryl shared a bittersweet toast to their new granddaughter and then went quietly to bed.

Less than a month later, Cheryl was again diagnosed with cancer. She fought and James stood by her but the beast was too strong. Cheryl lost her battle and James lost the love of his life…..she was only forty-one.

Sad and single, James poured himself into his work. He had always been successful and Cheryl had insisted that they save. They had been smart in their investments and even Cheryl's huge medical bills hadn't made too big of a dent in their portfolio. James didn't treat himself often, but he did allow himself one luxury…his cars. He bought his first Mercedes three years after Cheryl passed and found that he could trade every two years without affecting his payments. That way he always had a new car without the worries of an older vehicle.

He was on his ninth Mercedes when he was diagnosed with lung cancer. His doctors were not optimistic and he didn't really care. He decided early on that cancer would not take him as it had Cheryl. He would die under his own terms and on his own schedule. To that end he bought a Glock 10, legally registered it and even went so far as to take concealed carry classes. He purchased the smallest box of ammo he could and put the whole ensemble into his nightstand drawer. Then he made his plans. He would go out and get a piece of ass then come home and shoot himself. He figured that at least he would die physically happy. At this point in time that was all he could really hope for. With those thoughts in mind, he had gotten into his fancy car and driven off into the warm Cincinnati night…past the bright lights and into the />
James caught himself daydreaming about the past and nearly didn't see the red light at Fields-Ertel Road. He hit the brakes with little time to spare and had to catch his breath. 'Damn…I keep this up and I won't need the fucking gun', he whispered to himself.

Just off to his right James saw movement in the shadows. As he waited on the traffic light he saw the girl emerge from the darkness. Tall and slender, her shape stood out against the dim light. James could see just enough to know that she was well proportioned. 'This one', he said to himself. 'I want this one'.

Sandy's story

She was a hottie and she knew it. Just seventeen and built like God knows what, she could demand top dollar for her goods. And she did. While the going rate on the street was twenty for a blow job she got fifty. Straight sex was fifty and she easily pulled in a hundred. This was the life! The fact that she enjoyed the company of men for sex was just a bonus. She could jill-off ten times a day and not enjoy it as much as one good old fashioned fuck. Short or long, thin or fat…it didn't matter how the guy's package was constructed. Just as long as he had a cock it was good enough. The fact that she was getting paid for some thing she would do for free was a dream come true.

Her first fuck came when she was just twelve Even though she called him daddy she knew the man that she and her Mom lived with was not her real father, but she didn't care. They let her do what ever she wanted…in fact they rarely knew what she did. Mommy snorted line after line and Dad chugged beer and Jack Daniels from dawn to dusk. After a day of booze and coke they would both settle down (or just pass out) and she could relax. One night everything changed. Mom had passed out and daddy was drunk. She thought she would get some peace and quiet that night but Daddy slipped into her room and, after forcing her to sip some JD herself, he slipped into her pussy. It hurt like a bitch for a few moments then she realized that it was starting to feel good. Great in fact…she loved it! She started to look forward to the nights when Mom would coke herself into oblivion and she and Dad could fuck their collective brains out. Didn't last too long though. Mom woke up and caught them in the act. Damn was she pissed. She took a lamp to Dad's head and he barely got out before she killed him. Mom never seemed like she loved her again. She took care of her, but never smiled or kissed her again. She could feel that the love was gone.

At sixteen, she took to the streets. Mom didn't care what she did or where she went. Now, at just a shade past her seventeenth birthday, she was a girl on her own. She had a nice place, a car she loved and plenty of cash. All for doing what came naturally.

She had just finished blowing a guy in an alley for a quick fifty and had popped a couple of mints as she walked back to the main street. She saw the shiny Merc nearly slide through the intersection and thought to herself what a shame it would be for that nice ride to get cracked up. The windows were tinted so she couldn’t really see who was driving, so she just turned right and started her usual stroll up the street. She knew she looked good…long, shapely lags and natural big tits that bounced unfettered beneath her silk blouse. She had taken less than a dozen steps when the big black car pulled to the curb in front of her. she thought. ‘This could turn into something lucrative’. She moved toward the passenger side as the window slid down. She bent at the waist, stuck her head into the window and put on her best, though slightly crooked smile and said, “you lost Sugar”?

“Not really”, the old man behind the wheel said. “I’m looking for />
“Seems to me that you found someone”, she said in her huskiest voice. (That nearly ALWAYS worked).

“Indeed I have”, the man said. “Would you perhaps need a ride?”

she replied. “Where you headed?”

“I’m heading to my place in West Chester”, he told her.

she said. “I live in North College Hill. I wish I could take a ride in that sweet car of yours, but that is just so far from home for me…. Now maybe if we were on a date or something, I could go with you then you could take me home later. What do you think?”

His eyes brightened as he said “I think that would be a lovely idea, but I get really tired after dates. Maybe I could get you a cab home. I know a really good driver that I trust. He would see that you got home safely”.

Sandy knew many of the cabbies in town and she had fucked or sucked half of them so she wasn’t really concerned about her safety. She’d let the old guy think what he wanted. She would go with this rich old guy, get him off and head home for the day.

She opened the door and climbed into the luxurious car. The old man rolled the window up and started off back toward the outerbelt that everyone called the Circle Freeway. They traveled north onto I-75 for just a few miles and got off in West Chester. Neither one had spoken other than to introduce themselves (first names only) as they zigzagged through the quiet streets of the affluent neighborhoods until they reached a palatial gated community.

Sandy thought to herself as she got a glimpse of the huge estates they were passing. ‘This guy is really loaded. What the fuck is he doing prowling around when he could just order up any piece of ass he wants?’

James pulled the car into his drive, hit the remote and opened the garage. After pulling carefully inside he turned off the car, slowly got out and hurried best he could to Sandy’s door. She let him open it for her and even took his offered hand to assist her as she stood. Together, they walked into the mud room, then the kitchen and finally through the huge living room. Sandy was truly in awe of this home. She had seen them, of course, but had never been inside one so grand. James didn’t hesitate. He led her down the hall and into the master bedroom.

“We need to get the business out of the way first, Baby”, she told him.

“Of course”, James replied. “I’d like for you to spend the rest of the night with me if you are available to do so”.

Ordinarily, Sandy would be a bit apprehensive at this point. Most guys couldn’t meet her price for even half the night. Tonight (actually this morning), she wasn’t worried in the least. This guy had the bucks.

“It’s a thousand for the night”, she told him.

James didn’t blink. He took his wallet from his hip pocket and produced twelve crisp one hundred dollar bills. He handed the stack to Sandy who instantly saw that he had given her too much. she thought. ‘Am I getting an attack of conscience? She started to hand two of the Franklins back, but James told her “I know how much you said but this is what I want to pay. Will you accept it?”

“Of course I will”, Sandy told him.” If this is what you want to pay me”.

“It is”, he replied.

“OK. You get ready and I’ll be right back”, Sandy told him and she stepped into the bathroom.

James quickly took off his clothes and pulled the covers off the bed. He lay down and pulled just the sheet over his body and waited for the girl to return. He heard the toilet flush and the water running in the sink as he checked the nightstand drawer for the Glock. It was right where he had left it…. loaded with one in the chamber and the safety off. Right after she left he would use the gun and be done. Damn, he hadn’t meant to get poetic…he laughed to himself as he heard the water shut off and saw the bathroom door open.

Sandy had slipped into the bathroom with her little purse in hand. She set it on the vanity as she unbuttoned and removed her blouse. She left her black high heels on as she slid her skirt off. She took a moment to check herself out in the full-length mirror. She decided to leave her red satin thong in place until she got into bed with the old man. He might not have enough energy to completely undress her, but all guys loved taking her thong off. ‘Gives ‘em a sense of control’ she thought to herself. Satisfied that she was the hottest thing on two shapely legs she opened the door and walked back into the bedroom.

James was on the bed and under the sheet so she figured he was naked and ready for her. She climbed cat-like onto the bed and he smiled softly at her. Before she even reached him he held out his hand for her to stop.

“Something wrong, Baby?’ she said.

“Not really, but there is something we need to discuss”, he told her.

“Oh”, she said. “What is it?”

James lowered his eyes as he spoke, “In case you haven’t noticed, I’m a bit on the old side”.

He and Sandy both snickered just a little but then he continued. “I can’t really do much anymore. I have arthritis in my knees, arms and, well just about everywhere else. I can still ‘do it’, but I need you on top. Is that OK with you?”

Sandy didn’t really know what to say. She had never been asked before. It took a moment but she told him, love being on top”.

With that settled she curled up next to the man and pulled the sheet down. To say she was pleased would be an understatement. ‘This guy might be old, but he ain’t lacking in the cock department’ she thought to herself. It was true…James had a tool that she actually looked forward to enjoying.

As she pulled down the sheet, James reached for the girl’s panties. ‘Just a thong…I will buy her another one’, he thought. Nice. He hooked his fingers into it and pulled hard to both sides. The brief garment ripped apart with ease. James thought. ‘Now we’re both naked’.

Sandy felt her thong being ripped in half and nearly squealed. Then she thought, matter. I have a dozen more at home’.

James managed to slide his finger just once through Sandy’s slit as she sat up and took his half erect cock into her soft little hands. She pulled ever so gently and felt him grow harder by the second. She could scarcely believe that a man so old could get so hard so fast. James was nearly overcome with lust as he felt his neglected dick respond to Sandy’s gentle touch. The more she tugged, the harder he got and the more he wanted to fulfill his desires with this young beauty.

For the moment, his thoughts of ending it all vanished in wave of carnal pleasure. The way Sandy stroked his cock reminded him so much of the handjobs his loving wife had given him over the years. When the girl bent to take him into her mouth, he swore that he had been transported decades into the past when his sweet wife had wrapped her lips around him. Cheryl had been firm but like the girl was doing now. Not trying to get him off, but just getting him ready for what she had in store for him.

In his excitement he reached for her but found that she had positioned herself in such a way that his hands could only brush her skin. She pulled her mouth off his cock with an audible slurp and told him, ‘Just lay there, Baby. This is what you’re paying me for’.

For the first time since Cheryl had passed, James felt the cum rising from his balls. Good as it felt, he didn’t want his last blast to be in the girl’s mouth. “Sandy, I need to fuck you now. Would you please sit on my cock? I really want to feel your pussy”.

Sandy moaned sweetly as she slowly let his dick slip from her lips then moved her body over him. He hadn’t told her which way to ride, so she decided on reverse cowgirl. She liked this position for two reasons: she could control the penetration and he could enjoy looking at her beautiful ass.

Sandy took his cock in her hand as she lowered herself down. She nearly gasped as it slid in. It really was bigger and harder than she thought a guy this old could be. Truth was, it felt good. James loved it as well. He could feel her silky wet pussy snug around him as he slipped inside her. She was much tighter than he thought she would be. After all, she WAS a hooker. But he loved the way she felt. She began to move her body up and down on him. Every once in a while she would swirl her hips around while she had him buried inside her. She loved it and so did he. It wasn’t long before Sandy felt an orgasm coming over her. ‘Strange. Usually I just fake it for the money. I’m not gonna have to fake it this time’, she thought.

James thought.’ It’s almost over already. Oh />
Sandy was bucking as fast as she could. She could feel the heat flowing from her pussy throughout her entire body and she knew a big one was coming. James closed his eyes as the first rush of orgasm hit him. His entire being was caught up between his hard cock and the soft pussy it was buried in. Sandy’s tits were bouncing so hard that they were nearly hitting her chin every time she drove herself down onto James’ hard cock. She knew she was going to cum hard and she could tell he was right there as well.

They came together. James managed to lift his hips off the bed as Sandy’s cunt clamped around his dick. He shot a solid stream of cum deep into her as she unloaded a quart of her own juices around his cock and onto his belly. As his rush subsided, James smiled and relaxed back onto the bed. He never felt the pain in his chest.

As her orgasm ebbed, Sandy slowed her movements and finally moved so as to let his cock slip from her body. She turned to find James smiling and quiet. Not surprising, he looked as if he were sleeping. Sandy just shook her head. ‘These old farts always conk out after they get their nut. He paid for all night and I guess this was all night to him. Oh />
Sandy got out of the bed quietly and gathered her clothes. She went into the bathroom, peed, washed herself and dressed. James was still conked out flat on his back as she crossed the bedroom. get cold’ she told herself and she pulled the bedclothes over him.

She felt a bit sad leaving him like that, but it was just a job. No matter how much she liked it sometimes, this was her way of life.

Sandy paused in the living room to call a cab. She asked for her favorite driver and found that he was available. She told him where to pick her up and headed for the front door. She never noticed the photos that were placed all around the living room. Pictures of a pretty little girl with her Mom and Dad. Pictures taken years ago. Pictures of a girl that looked a lot like her. She crossed the floor and walked out of her house into the fog of a Cincinnati morning.

story by: George in Cincy

Tags: fiction male/teen female consensual sex death prostitution sex story

Author: George in Cincy

Related sex stories:

  • My voyeurism story

    I looked out on to the balcony where Maddy was laying sunbathing, her top off. On closer inspection I could that she was wriggling in her lounge chair. Her hand was squeezing and pulling her left nipple as her other hand dipped down past the brick work. I'm guessing it was going to work on her little pleasure bud. To say I prefer to play instead of watching is an understatement but...I met Sam a month back and since then...

  • Hot Sex with a Cheating Wife

    I bit her nipples harder than before taking care not to leave marks, and smacked her pussy repeatedly until she wiggled with pleasure, cumming in a wave of ecstasy and delight in one combined motion. I rubbed her clit until the wave ran out. Her eyes looked at me full of want. Did I know it was wrong?  Of course I did.  But I justified to myself like this…‘Would I like someone (more…)

  • Romantic Sex Story

    He nestled his face in my pubic hair and kissed me. It was so hard for me to lay still, my legs involuntarily jerked at my side because of the sweet sensation building in my groin. With his lips at just the right spot and his tongue batting back and forth I arched my back in ecstasy. My husband Dan and I were about to celebrate our fifteenth wedding anniversary, but for some reason he’d been spending all his spare...

  • Lila was so beautiful

    I walked beside the bed where she laid. I kissed her mouth and headed South, kissing her neck and biting it as I followed my want. Her nipples hard were again in my mouth as I sucked on each. I reached down and grab her panties and pulled them off. Just a small patch of pubes right in the center of her mound showed me the way to heaven. I kissed down until I found her hairy spot - this...

  • Sorority hazing

    Hi, I am Jan and now the president of the top sorority on campus, I have to monitor our pledges to make sure they are up to our standards. They have to be great looking and smart. Did I mention that they also have to be a fantastic fuck(both with men and our sisters). This is the story of my pledging. During the first week of pledging about ½ of the pledges either leave on their own or are ask...

Sean shows me how sex should be

My best sex story ever

Wifes first mfm, what a night

Jessica and I

Curious Friend

Leave a Reply

Your email address will not be published. Required fields are marked *