That Summer

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Bad Billy is sentenced to summer on the farm.
  • June 2001 monthly contest
15.7k words
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rgjohn
rgjohn
11,555 Followers

* * * Chapter 1

It seemed to 18-year-old Billy Mayfair that he had been on this bus forever already, yet he was not even half way there. It was a long trip from Fresno, California to South Dakota, especially on a bus.

Billy looked out of the window, contemplating how he had ended up on this bus to nowhere. He had been out with several of his friends after high school graduation, looking for some fun. The BMW was just sitting there, keys in the ignition, waiting for someone to drive it away. Billy didn't want to do it but his friends called him a coward. Well, they didn't get five miles before the cops caught them.

His mom had been mortified; her son was a criminal. She and the Judge agreed that Billy needed a change of scenery. The Judge gave Bill a choice, go to jail or work for a friend of his mother on her farm in South Dakota for the summer. Even for an eighteen-year-old, that was a 'no-brainer'.

Jess Morgan, his mom's best friend had married a man and moved to a farm in central South Dakota. Then she had lost her husband suddenly last year, leaving her with over a hundred acres of farmland and a lot of bills. Still, Jess was not the kind of woman that gave up easily; she was determined to make it on her own.

Billy barely remembered Jess; he had not seen her in years. His mom said he had always called her Aunt Jess because she had treated him so well. He was certain that she would be some dried up old hag, maybe even 40 years old. He was beginning to think that jail might have been a better choice. How was he going to make it through an entire summer in the middle of nowhere? He wasn't even sure there was running water on her farm.

He was dozing when the bus stopped in Salt Lake City. A few people got on, but the bus was far from full when it pulled out of the station.

A woman in a business suit sat down in the window seat across the isle from Billy. He paid little attention to her, preferring to sleep, hoping that when he woke up that this trip would have just been a bad dream.

An hour or so later he was jarred awake by a yell from across the isle.

"Goddamn it!"

Billy jumped, startled. He saw the woman across the isle sitting there with a portable PC on her lap and looking at the screen in frustration. Billy saw her slam the top down and sit back sighing.

"Problem with your PC? Billy asked.

"I'm sorry, I didn't mean to wake you. I think the hard drive just crashed, I hate these things. Now I don't know what I a going to do. I took this damn bus so I could work on my presentation and now I'm not sure I can even get the program back up. I'm in big trouble."

"Maybe I can help, I'm pretty good with those things," Billy said with a big smile, desperate for something to distract him.

"Oh God, could you look at it? I would be forever in you debt," the woman said, her eyes lighting up.

"Sure, bring it over here."

The grateful women got up and brought her PC over, sitting in the seat next to Billy.

Billy could see that she was a very attractive lady, maybe 35 years old. She had on a pretty blue suit with a short skirt, matching vest and a white frilly blouse underneath. Billy noticed her legs as soon as she sat next to him, far too old for him, but not bad.

Billy handed the woman the CD player he had been holding on his lap and took her PC. He opened it and quickly brought up the operating system. He could see her watching him with apprehension as his fingers worked the keyboard. Ten minutes later, he had her program back up and running.

"There, you should be fine now."

"Oh wonderful, you are a life saver. I know very little about these things. Thank you very much. I'm sorry, I am being rude, my name is Jill Madison," she said holding out her hand.

"I'm Billy Mayfair," Billy said, taking her hand.

"Very nice to meet you Billy Mayfair. Where are you going?"

"Podunk South Dakota, to stay with a friend of my mom's for the summer," Billy said sarcastically.

"Oh it can't be that bad," Jill said, turning toward Billy and bring her legs up onto the seat.

Billy did not miss the flash of thigh as she adjusted her position.

"Oh, it is that bad," Billy said using her words. How would you like to live on a farm for the whole summer with cows and pigs and stuff? I'm not sure that they even have inside toilets, let alone something like a movie theater."

"Well, maybe you are right after all, you're screwed," Jill said laughing.

Billy laughed too, enjoying this lady's company.

"What kind of music do you like?" Jill asked, holding up his CD player.

"Just about anything as long as it is not old folks stuff. I have a CD from Bare Naked Ladies in there, would you like to listen?"

"Great, I love Bare Naked Ladies," Jill said, putting the headphones on.

Jill listened to several songs before taking the headphones off and handing them back to Billy. "Thanks, that's a great CD."

As Jill moved her legs again, Billy heard something snap. It sounded like a rubber band.

"Damn," Jill said, looking down at her thighs. "I hate that," she said, reaching for her garter strap, which had slipped loose.

Billy sat wide-eyed as Jill reached under her skirt and pulled the strap down and attempted to reattach it. Billy felt his mouth go dry as he saw Jill's hands working under her skirt.

"Sorry, but I hate pantyhose. Unfortunately, it's really hard sometimes to keep these things hooked," Jill said, still unable to fix it.

Billy was getting quite a show as this sophisticated lady tried to adjust her nylons.

"Shit, nothing is going right for me today, it's broken," Jill said, looking at Billy. "Are you good at fixing these things too?" she said, holding the broken clasp in her hand and smiling. She knew that he could see directly up her skirt.

Billy looked up to see her smiling at him. He felt his face flush.

"Well, I can't go around with one garter strap broken all day, I guess I'll have to take them off," Jill said as she reached under her skirt, unhooked the clasp and began to roll one nylon down her thigh.

Billy felt his cock begin to lengthen in his pants as he watched this stranger take her nylons off right in front of him. By the time she had both nylons off, Billy had had quite a show. He even knew the color of her panties now. He had to hold his CD player over his lap to cover his raging hardon.

"Do you have a girlfriend that you are leaving back home?"

"Yea, sort of."

"I'll bet that's going to be'hard' on you being way out there without a girlfriend," Jill said, emphasizing the word hard. Jill looked down at Billy's pants and could plainly see that he was excited. She reached over and placed her hand on the thigh of the startled young man, leaning close to him.

"Now, let's see how I can help you," Jill said looking around to make sure no one had moved close to them. "It seems that you have your own operating system problem here," she said, placing her hand directly on the bulge in the young man's pants.

Billy thought he was going to pass out. Sure he had fooled around with Kelly a little but this was a woman, not a fifteen-year-old girl. He was paralyzed with fear and excitement as he watched the woman's manicured fingers begin to open his belt and pull down the zipper.

"Oh my," Jill said, as Billy's cock sprang out, surprised to see that he wasn't wearing any underwear. Jill's hand went to the throbbing shaft wrapping her fingers around it. She slowly moved her hand up and down, bringing a moan from the excited young man.

It wasn't an overly large cock yet but it was well shaped with a nice purple head.

Jill continued to move her hand up and down, bringing another moan from Billy. Jill didn't normally do something like this. She wasn't sure what had gotten into her today. Maybe it was because he was so cute and he had practically saved her job.

Billy watched in amazement as Jill began to increase the speed of her hand. He saw her squeeze his cock, forcing the clear juice from the slit in the head and using it to lubricate her hand. He looked at Jill and saw that her face was a mask of concentration, her lips slightly open, breathing through her mouth. Billy was trying to hold back, to make it last but he couldn't take much of this; after all, he was only 18 years old and a virgin.

Jill felt Billy's cock throb and pulse, swelling in her hand. She brought her other hand over and began to lightly squeeze his balls until she felt them tighten up. She knew from experience that he was ready to come. Jill moaned as she felt her young friend tense, his hips lifting slightly from the seat. A tremor went through her as she watched the head of his cock swell and begin to spit white cream out of the slit with great force.

"That's it, that's it, cum, squirt out all that sweet juice," Jill whispered, feeling her pussy spasm in excitement.

Billy's cock throbbed again and again, squirting his juice until it was in a puddle on his stomach and coating the woman's fist.

Jill squeezed the last bit of cum out of his shaft and looked up at Billy's amazed face.

"Well, is that a good enough pay back?"

"Uh, uh, yea...thanks," Billy stuttered, his face turning red, not knowing what to say to a stranger that had just given him a hand job. This was only the second hand job Billy had ever had. The first was from a girl in the ninth grade but it was nothing like this.

"You are quite welcome sweetheart. Now what are we going to do to clean up the mess you made?"

Billy shrugged his shoulders.

"Well, since you seem to have lost your underwear, your pants are going to be a sloppy mess," Jill said, pausing to think. A smile came to her face.

"I guess that I will just have to give you mine."

Billy watched as Jill lifted her ass from the seat and pulled her skirt up. She grabbed her pink panties and pulled them down. Billy felt his cock twitch again as Jill flashed him her pussy.

"Here," Jill said, using the panties to wipe up the cum on his stomach, then clean off her hand. When his discharge was mostly absorbed into the panties, Jill handed the sticky cloth to Billy.

Billy looked at the panties and back at the woman at a loss for words. Thankfully he felt the bus come to a stop.

"Well, this is my stop, thanks again sweetheart," Jill said, bending over to give Billy a quick kiss on the lips. She smiled at the stunned boy, picked up her PC and was gone.

Billy couldn't believe that he had just gotten a hand job from a complete stranger, a gorgeous woman. Yet he sat there with his pants open and her panties in his hand as proof.

* * * Chapter 2

The bus crossed the South Dakota State line at three in the afternoon. There were still two hundred miles left to go; this was going to be even worse then he had thought.

Billy listened to his CD, watching out the window at the wide-open spaces. He never thought there was this much uninhabited space in the entire country, let alone South Dakota. There were cattle farms, cornfields, and wheat fields but very little in the way of civilization.

The sun was just going down when the bus pulled into the town of Fort Pierce, South Dakota. As Billy stepped off the bus, he stretched, looking around for his mom's friend. He was not even sure what she looked like.

Suddenly he heard someone say "Billy?"

"Yes,...Aunt Jess?" Billy said, looking at a woman walking up to him in a cowboy hat and boots.

"My but you have grown," Jess said, putting her arms around him for hug.

She was nothing like Billy thought. He had expected a tired old woman; what he saw was very pretty and trim woman in tight jeans, boots and a western shirt. Billy felt her full breasts push into him as she prolonged the hug. For an old lady she was pretty sexy.

"Let's get going, we still have an hour and a half drive."

Billy groaned.

"Aunt Jess can we get something to eat first?"

"I'm sorry, sure, what would you like?"

"Anything."

"By the way, you don't have to call me Aunt Jess, that was a long time ago."

"I don't mind that, my mom said you were like an Aunt to me."

"Whatever you want sweety," Jess said with a smile to the cute young man.

Billy got his bag and followed her to the pickup truck. It was not a bad position walking behind Jess; she filled out those jeans very well.

They stopped at a small diner about ten miles outside of town for dinner.

"Well, tell me about yourself young man," Sally said after they had ordered.

Billy looked across the table at Jess. She had taken off her cowboy hat and revealed pretty blond hair that came to her shoulders. Her eyes were a piercing blue. Billy thought that she looked somewhat like the actress Bo Derek. Maybe this was not going to be such a bad summer after all, he thought.

"Aunt Jess, I didn't really steal that car. It was just some of the guys I run around with, having fun."

"I'm not here to judge you Billy, I am just thrilled that you're here. It has been very difficult for me since John died," Jess said, her pretty blue eyes tearing up. "The farm is so big and needs a lot of work. I tried to hire some immigrant workers, but they were just not reliable, plus I really don't have the money. Now it's just me and you of course, for the summer."

"Aunt Jess, I don't know a thing about farming, I'm a city kid. Hell, if you have a computer, I can do wonders with that."

"Well, I do have a computer but other things need fixing more. Don't worry, I will teach you all you need to know about farming," Jess said, reaching over to pat Billy's hand. "We had better get going...here, you can drive," Jess said, tossing him the keys.

"Really, you are willing to take you life into your own hands with a kid who also happens to be on the FBI's ten most wanted?"

"I'm sure I'll be safe," she answered her face lighting up with a smile.

Billy already liked Jess.

An hour and a half-later Jess jumped out to open the gate to her farm. Billy drove the pickup through the gate letting Jess get back in. It was another half mile to the large old farmhouse.

"Billy, you will be staying in the room over the barn," Jess said pointing to a large structure. "It is a little messy but you will have more privacy there, if that's okay?"

"Sure Aunt Jess, I can sleep almost anywhere," Billy said following his Jess into the house.

"I will fix up the sofa for you tonight and then we can fix your room up tomorrow. I'm going to take a bath now. I'll try to not use all the hot water. I need a new hot water heater also."

"Thanks Aunt Jess, give me a yell when you are done. By the way where is the TV?"

"We don't have one."

"Oh my God," Billy said under his breath.

A half-hour later, Jess called down and said the bathroom was free.

Billy went up the stairs searching for the bathroom. He turned left and took two steps before he stopped. The door to Jess's room was left open a crack. He knew he shouldn't look but he couldn't help himself, stepping toward the cracked door. He sucked in his breath when he saw that she was bending over a dresser drawer getting out her nightclothes. Her ass was facing directly at Billy. Her white panties were stretched tight across her ass cheeks, outlining her well-shaped ass. Billy could even see the pouch of her pussy bulging between her legs.

Suddenly she stood up holding her nightgown. Billy barely got out of the way before she turned around.

Jess saw something out of the corner of her eye in the mirror on the dresser. She realized that she needed to close the doors now that she had a guest. There was a man in the house for the first time in over a year.

Billy hurried down the hall, hoping he would find the bathroom quickly. Two doors down, he saw the open bathroom door and hurried in, closing it behind him. He breathed a sigh of relief.

"God, she is my mom's best friend, I must be nuts," he thought.

The bathroom was old and small, with a big Victorian tub against one wall.

Billy started the water and sat on the toilet to take off his shoes and socks. He saw something on the floor near the hamper, he reached over and picked it up. His heartbeat increased when he saw that it was a pair of Jess's panties. She must have missed the hamper.

With the panties in his hand, Billy sat back down on the toilet. He was in a battle with himself, an angel on one shoulder and Satan on the other. Satan won; Billy brought the soiled panties to his nose, breathing in the sent of her. He moaned as his cock grew to full erection.

The tub was rapidly filling with almost warm water.

Billy laid the panties down on the toilet seat and stripped. He got in the tub lying back, his hard cock sticking above the water line. He looked at the panties laying arms reach away. He controlled himself, quickly washing and getting out of the now cold water.

When he was dressed again, he picked up the panties, intending to put them in the hamper. Instead, he put them in his pocket. There was another pair in there already.

He was sitting on the sofa when Jess came down. She was wearing a fairly well worn flannel nightgown.

"I'll get some sheets, there are pillows in that closet."

When the sofa was made, Jess said good night and went up to bed.

Billy stripped to his shorts and got under the covers. He lay there for awhile, trying to get to sleep. Finally, he reached over and pulled the two pair of panties from his jeans pocket. He dropped the pink pair to the floor and held the other pair to his nose. With his other hand, he began to masturbate, running his hand up and down his hard cock with increasing speed. As he neared his climax, he brought Jess's panties to his hard cock and covered the head. He moaned and began to squirt cum into the crotch of her panties.

Exhausted from his long day, Billy fell asleep, the hand holding the now sticky panties dropped to the floor.

The following morning, Jess was up before dawn as usual. She tried to be quiet as she walked by the sleeping boy. She stopped short, looking on the floor next to the sofa. It looked like there were two pair of panties lying there. She reached down and picked them up. One pair was definitely the panties that she had worn yesterday, the other pair she did not recognize.

She dropped the pink pair back to the floor and walked quickly to the kitchen with the other. When she closed the door, she leaned against it and sighed. She looked at the still damp panties. Billy had obviously jerked off into them; the crotch was still very wet. She felt a thrill run through her and her pussy lips began to swell.

"Control yourself," she whispered.

John, her late husband had a panty fetish and she had always indulged him. He loved for her to wear them all day and then masturbate in them before she took them off and gave them to him.

She allowed herself a moment to remember her husband.

John had loved everything about Jess. He especially liked her pussy.

Her pussy had always embarrassed Jess; the clit was quite large and her inner lips were overly large and would protrude even when she was not excited. When she got excited, both the clit and the lips would grow to twice their normal size.

In high school, she was always embarrassed when she had shorts on, fearing that people would notice her lips. She also kept her pussy shaved, pubic hair made the problem worse.

After they were married, John had convinced her that her pussy and clit were beautiful. He even had her start wearing tight shorts and jeans again.

Jess shook her head, trying to focus; she didn't like to dwell on the past.

Jess, still leaning against the door, began to raise her nightgown, unable to stop herself. She brought the damp panties to her already swollen pussy lips. Her legs began to shake as she rubbed the material against her protruding clit. She opened the panties so that the area wet with Billy's sperm was touching her tender lips. In seconds, her body shook in climax, forcing her to stifle a moan.

rgjohn
rgjohn
11,555 Followers