Jeff The Jerk-Off Cowboy

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Young Jeff is a source of much entertainment to local ladies.
2.5k words
4.18
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Part 1 of the 3 part series

Updated 11/02/2022
Created 10/13/2006
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mef
mef
30 Followers

When Jeff Jones was 12 years old he had been a skinny little squirt who girls had laughed at. Now at 18, after 6 years weight training, football and a sudden growth spurt, he was six feet 2 inches of solid muscle. Huge biceps, broad shoulders and massive abs tapered down to a six pack, before thickening out again to two tree-trunk thighs with a solid 9 inch cock between them. His pride and joy, though, was his amazing ass: two high, round and hard cheeks that had already caused the production of several gallons of pussy juice, and featured heavily in the bank of mental images the girls and ladies of the small town of Roxboro called on during bouts of self-abuse.

Jeff knew that girls thought he was hot, and that some of the air-headed little teenagers around town probably whacked off to him - he'd seen them, with pointy little nipples, gawking at his rippling muscles and fat package, had seen them peeking through the fence when he worked out in the garden in just a speedo; but he had no idea he was the jerk-off cowboy of many of the older women he knew: respectable, often married, ladies who were pillars of the local community.

For instance, Mrs Johnson who lived next door, a mother of 3 young girls and (to Jeff) an old lady of 38 had been observing with lecherous pleasure the development of the Jones boy. Though Jeff noticed that she often came out to tend the garden when he was working out outside or sunbathing, it never occurred to him that she was checking him out, letting her eyes slide over the flexing muscles and hoping for a peek at the amazing cheeks. The divorcee would sometimes, if the girls were playing downstairs, sit near her bedroom window with her jeans and panties pooled around her ankles and her fingers sloshing in and out of her thickly bushed vagina, keeping her eyes on the amazing display in the garden and her ear cocked for a sudden scampering of little feet on the stairs.

His mom's best friend Jane was a married mother of 2 aged 40; she had bad teeth and a wicked grin that she often seemed to direct at Jeff, especially when he was wearing very little. She had developed a disturbing habit of bursting in on him in his bedroom and the bathroom - usually with apologies and excuses, but still with that wicked grin. One time he had been working out naked in his room, and, quickly wrapping himself in a robe to go to the bathroom down the hall, he'd bumped into a red-faced Jane who seemed to be pulling up her pants; but he never occurred to him why.

Jeff had a girlfriend of 3 years named Mandy Lewandowsky. Mandy was a pretty scary little fireball, so everyone new not to make a move on Jeff. Mandy was five feet 2 inches with short brown hair; not hot, by any means, and people wondered why Jeff was with her. The truth was that the relationship was perfect cover for both of them: Mandy was a closeted and very frustrated dyke ; and Jeff was.....gay, and equally frustrated. This wasn't the kind of town that either of them could come out in, so jerking off to the internet was the extent of both of their sex lives.

---------

Candy James was 26 and pissed off with life as a 12th grade teacher at Roxboro High School. In fact it was not just the lazy, insolent kids and the fat dyke principal who kept increasing her workload while staring at her tits, it was the boring, piss-ant little town itself.

She'd been desperate to get her first teaching job after graduation and hadn't realized that teacher at a small-town high school would mean that her social life would be reduced to zero. No hot clubs or other meat markets in this little burg, and even if there had been she would have been reported by some busybody to the principal who would have had a pious little talk with her about being 'a model of rectitude to the students', while getting a fucking wide-on at the thought of her in revealing club outfits.

So Candy was bored, pissed off and.... fucking horny. She hadn't gotten laid in 3 months and was practising the sin of Onan more than she had since 9th grade. It didn't help that everywhere she looked there was fine young male flesh - shirtless boys on the sports field, tight asses in the corridor and well-filled packages obscenely displayed by slouched and open-legged young hunks in the classroom. Some days her clit seemed as if it was about to drill a hole in her panties.

She did have a sense of dignity, though, not much of a one, but she did have it. Not only would molesting one of these tasty pieces of beef get her ass fired but she thought it was pretty lame to obsess over school kids. Sometimes though the flesh was weak and she repaired to the faculty bathroom to 'ease her mind' -though for that process she allowed that mind to fill with images of shower scenes, circle-jerks and nude Gym sessions.

The worst offender was Jeff Jones. Dumb as an ox but with an ass that she wanted to bite. Today he was sitting in the front row in a pair of shorts that left little to her fevered imagination. Sometimes she thought that these little fuckers did it deliberately, clit-teasing her knowing that she'd risk getting fired if she made a move.

Jeff was daydreaming about his friend Paul Evans; more specifically, he was running a few minutes of mental video in which Paul soaped up his body in the after-game showers. As his cock hardened and lengthened, he wasn't aware that it was having a similar effect on Ms. James's clit. "Holy fuck, he's getting a hard on! - man what a tube of meat" . She was soaking her panties at a rate of knots and crossed her legs to get a little relief, grinding her lips together, all the time keeping one eye on the show under Jeff's desk.

Jeff was getting more and more exited. As Paul stroked his long, fat tool in his mind, he realized to his horror that he was past the point of no return. He felt his cock lurch and the first spray of thick come hit the inside of his boxers. Candy watched the amazing thrashing dick and then the shocking sight of a wet patch growing on the shorts...

"Oh, fuck he's coming. Fuuckkkaaahh" Candy's womb began to contract as her pussy squirted more juice into the crotch of her panties as she orgasmed.

After a few seconds she looked around to see if anyone had been watching - nope, all still reading their textbooks ..except - fuck, Mandy Lewandowsky was smirking lecherously in her direction.

Mandy winked and licked her lips. "Man, what a horny bitch. She came in her pants looking at Jeff's package - she's probably got a majorly swollen pussy right now" She grinned nastily and filed the image away for her next jerk-off session.

-----

When Jeff got home that afternoon, his mother wasn't alone. A woman of about 25 with greasy brown hair, unhealthy skin, and a smattering of acne around her rather large nose was arguing with her. It took Jeff a few moments to realize that is was his Aunt Amy, his mom's sister. She and his mom had fallen out about 5 years ago and he hadn't seen her since.

"Fuck, is this Jeff? Holy shit!" She said

Amy couldn't believe her eyes. The little dweeb she'd teased mercilessly a few years ago had transformed into the most amazing piece of ass she'd seen in a long time. She let practised eyes roam over the hard and exciting surfaces of male beauty before catching herself, realizing who this was. "For fuck sake, control yourself, Ame" she whispered to herself as she felt an embarrassing moisture soak her thong.

Self-control had always been Amy's problem; a drop-out and drug addict, she'd turned up on her sister's doorstep after she'd blown another job by turning up late and high. Her big sister Joan, 13 years older than her 25, had always been like a mother to her and she was pretty shocked when she said 'not this time'. After an hour of tears and shouting, Joan had agreed she could stay if she cut out the drugs and looked for a job.

"Yeah, Yeah Whatever you say. Please Joan you've gotta let me stay. You know Mom and dad won't let me back in the house'

"I mean it Amy - any more fuck-ups and that's it"

Amy hugged her, amazed that her up-tight sister had said 'fuck'.

Next morning after Joan had gone to work and Jeff to school, Amy decided to have a look around the house before getting dressed and - sigh - looking for another fucking dead end job.

Let's see what you've got hidden, Joanie eh? Nothing. Nothing. Nothing. What's this box under the bed. Now where would it's key be...?

The key was in the bedside cabinet - so fucking easy, sis - Opening the box yielded quite a surprise. Uptight sis had quite a stash of pornos and a few Playgirls as well as a 10 inch life-like dildo. The package said - holy fuck! - 'South of the Border'. A replica Hispanic cock. "You dirty bitch Joanie - we have something in common" Amy thought, as she remembered Raoul from High school and that astonishing piece of meat of his.

Amy paused for a moment - mmm I promised I'd look for a fucking job...

Amy's conscience warred with her cunt until.....the box was dumped in from of the VCR in the living room.

Amy checked out Jeff's room. A dirty jock on the floor drew her attention. "Don't be a fucking perv, Amy"; but it still seemed to find it's way into her pocket along with some weed (score!) and an unmarked Video that looked interesting.

2 Hours later Amy hadn't started to look for work; her no-drug promise had been forgotten about as well as she lazed in the recliner, joint in one hand, the other sliding the dildo into a very wet vagina while watching her sister's 'Hung Studs Jerk Off VI' video. The room stank of pot and pussy.

As the tape ended, Amy spied the unmarked tape from Jeff's room on the table. She got up and exchanged tapes. "What the fuck's this?" She said as it seemed not to be the porno she'd thought it was.

"Hi, I'm Jeff Jones, and this is my audition routine"

"Does Jeff want to be a dancer? Holy shit!"

It became clear just what kind of dancer Jeff wanted to be when he stripped to a tiny thong which showed most of his incredible ass. Amy watched mesmerised and began rubbing her enflamed vagina.

"I fucking shouldn't" She said to herself, just as Jeff began swaying the amazing cheeks at the camera.

Amy lay back and began to really jerk off in earnest, pushing the sweaty jock to her nose with her other hand.

- Jeff had been persuaded by his friend Sarah that a good way of saving money for college was performing at the local Strip Joint which ran a Ladies Night on Tuesdays. He wasn't sure about it as he wasn't sure he wanted a lot of women pawing him but told her that the reason was he didn't want his Mom finding out (as if she would!). He was also pretty surprised that Sarah new about the strip joint. He was always comfortable around Sarah who was short , fat and shaped like a bowling ball. She had never had a boyfriend as far as he knew; she didn't seem interested in sex and was one of the few 12th grade girls who didn't gawp at his body.

Sarah worked on him for a while and even contacted the owner of the club who transferred her to his daughter who ran the ladies nights; she said that if Jeff wanted a job he needed to make an audition video and send it in.

"Look, just set up the camcorder and do it - don't forget you need to be naked with a hard-on at the end"

This hadn't been true but Sarah was looking to improve what was going to be the latest edition to her porn stash...In fact it was better than she hoped when Jeff jerked off at the end when he thought he'd switched off the camera.

Best friend Sarah whacked her pussy till it was raw......

Jeff kept a copy which he hid under his bed and the third (or second, as far as Jeff new), went to Charlene Timmons at the club.

Ms Timmons was 21 and had recently been thrown out of college for cheating in exams and then offering pussy to the dyke in charge of the college's investigation. The lady might have taken her up on it if Charlene hadn't been skinny as a pole with a shock of violent red hair. She had then been given the job of supervising the ladies nights by her disappointed but not surprised daddy and she couldn't believe her fucking luck. She'd spent most of the plane ride home beating off in the tiny toilet imagining being surrounded by hugely-hung studs. Maybe she'd get to audition a few, heh , heh! Maybe they'd offer something in return for the job. Fuck, Yeah!

Such dreams never work out in reality. Charlene found that the job seemed to be entirely paperwork - she often didn't even have time to watch the shows but at least when she did the action was viewable from her private office - frantically pulling up her jeans when her daddy rapped on the door to ask why it was locked.

She was eventually put in charge of auditions and came up with a brilliant plan. Instead of live auditions, she'd asked for videos, videos she could watch in err, private. The guys auditioning quickly realized what the horny little carrot top was up to and got hotter and nastier than they would normally in the hope of getting a job at the largest strip joint in the area. Soon Charlene had a fabulous collection. She jerked off so much she could hardly walk at times - the last time that had happened was when her dad had gotten her a computer at 15 and she discovered Internet porn.

This morning she'd got a new tape through the mail. 'Jeff, aged 18'. Yeah, whatever. Probably 35 and over the hill. She put the tape in the vcr after locking the office door. 20 minutes later an exhausted Charlene was draped across the armchair displaying a sore, gaping pussy, surrounded by thick, wet, orange hair still dripping liquid onto the upholstery. Man! This kid is fucking hired!

"Charlene, why have you got this fuckin' door locked again?"

Her dad pounded the door as Charlene fought to get her panties and jeans up her skinny, white thighs.

END OF PART 1

mef
mef
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