Jay's MILF Ch. 01

Hello to all! All characters in this story are fictional, and are over the age of 18. This is a story about Blackmail so if that isn't you thing, click away now! Otherwise, I hope you enjoy!

PS - The expert editing on this was done by Kenji Sato, please consider him for all such work!

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Jay Fortson was home hanging out, waiting for a few weeks until his freshman classes would begin at the local university. He had just come in from his daily run, and was getting a drink from the refrigerator. Jay stood six feet six inches in height, with short, blond, shaggy hair; Jay was just too clumsy and slow to play sports. But since graduating, he had really been improving his health, and was now much thinner and leaner. Though he would usually go to the family beach house for a few weeks of fun before school started, a week plus was all that was left; so for the moment, he was basically stuck sitting at home alone, as his parents were doctors at the local hospital. All was quiet, until yesterday.

Yesterday, while sitting at home, Jay noticed someone moving across his backyard. This neighborhood was a gated community, so thinking them to be a burglar or the like, Jay went to confront....only to see him enter the backdoor of his neighbors' home. Jay's parents were neighbors with David and Julie Bagwell, a local pair of very successful realtors. They had their own realty office, and Jay normally worked odd jobs for them during the summer. Julie Bagwell was a tough person to work for, always giving Jay 'shit' jobs and the like, so seeing a man who was in no way similar to David Bagwell had him wondering. As Jay looked out a side window, he saw that Mrs. Bagwell opened the back door for the man...and she was wearing just a thin bit of lingerie!

Jay knew Julie Bagwell to be close to forty, if not a year or so over, basically twice his age. She was about five feet six inches in height, and quite the MILF. She had raven-black hair and a lithe petite frame, showing her Italian ancestry. Jay was so shocked to see this, he had simply allowed the door to close, and then slipped across. Thank goodness the latest iPhone had a better telephoto lens, as Jay was able to get some good footage of Julie on all fours in her den, a visibly-darker man behind her, pounding away. Her husband, David, was a pale-skinned man and was nothing like this guy. After maybe a minute, he stopped the recording, as he had all he needed. Relocating back inside to an upstairs window, David caught the guy on film just a minute or so later, walking stagger-legged across the two backyards, then getting into a blue sedan with a county government sticker on the door, on the road behind their two houses, and driving off.

The next day, Jay really smiled as he tromped down the stairs. He had managed to get a few good stills of Julie and print them, along with a thumb drive and a note, containing only his cell number. Jay knew from her routine, that Julie would come home every day at about one o'clock, enter the side door inside the garage, and then work from her home office. As the garage door had been left up, Jay simply walked over and hung the envelope on the door knob, went home, and waited.

Jay was in the shower, only having recently come back from his daily run, when heard his cell phone ring. He smiled, and allowed it to go to voicemail, which he had changed due to this situation, and continued to shower, being careful to give his 'junk' a second soaping. Jay's cock was partially hard at the thought of fucking this total MILF. Even though his body was far from perfect, Jay had had a few couple of girlfriends, so he had some sexual experience. But neither were anywhere close to Mrs. Bagwell in looks. She was damned gorgeous, and he intended to make the most of this opportunity.

As he toweled off, Jay smiled. He got at least two calls as he was finishing his shower, and his text 'ding' sounded, as he hung his towel and walked to his phone. Looking at the clock, he saw she was right on time. Picking up the phone, he looked at the text and listened to his voicemails. As expected, they were from a woman who was angry at being caught, and clearly in a panic.

The text of 'WHAT DO YOU WANT' in all caps really confirmed it.

Responding, Jay texted, 'Someone has been really naughty, and WE are going to have to figure out what WE are going to do about it.'

Upon seeing 'SHOW YOURSELF' when Mrs. Bagwell responded, Jay laughed out loud.

He knew on Mondays, Mr. Bagwell came home early, as opposed to five or six o'clock, so he still had time to set a few rules...combined with some fun. Taking a second set of the info he hung on her door, Jay strode out in great confidence. It was only Monday, after all, and Jay's week was really shaping up.

Julie Bagwell was a woman who had it all, or so she thought. She and her husband had what was, far and away, the most successful privately-owned real estate firm in the area. She was on charity boards, and served on a financial governance board for the county--she was a woman on the move. People jumped at the mention of her name, and she liked having power.

So when she opened the big manila envelope, the color immediately drained from her face. She was so shocked, she actually called out--thankfully, she was at home alone. Panic filled her mind. Julie had worked hard to craft her position of power, and she knew that if word of this got out, she would be immediately off the governance board, a position she had obtained by fucking Derek Bell, the man in these pics. This governance board was to be her centerpiece to making the jump to politics, so it was with a shaky, if not panicked hand, that she dialed the number.

Two calls later, and the asshole wasn't answering. 'Fucking typical', she thought, and, taking a deep breath, she calmed herself. 'It's just a question of money,' she told herself. Going to the back office that she had set up, she reached into the extreme rear of one of the filing cabinets, and fished out a fat, stuffed envelope, overflowing in cash. Dave, Julie's husband, never used this office, so Julie had taken it over more than a year ago. "Damn," she said aloud, "breaking into one of my caches." Just then, she got a text, and her blood went red, angry at this person trying to blackmail her. "WHAT DO YOU WANT" she texted. The response only made her more angry. Her nails made audible sounds, as she pounded out, 'SHOW YOURSELF' and waited for a response. It was not long in coming

By his nature, Jay was not normally a guy that exuded confidence, but this was different. Jay had this woman dead-to-rights. So he knew he had only to go over there like he owned that shit, and she'd back down. Mr. Bagwell was known in the community as a man of character, so he was sure that worst-case scenario was that Julie's actions would get her divorced, disgraced, and down-trodden, and he was sure she'd never go for that. He just had to take the air of aggression, something she would not expect, and it would all go down fine.

Jay saw Mrs. Bagwell's expression go blank as he walked into the garage, and held up the large envelope, as he hit the close button on the garage door. He smiled, seeing her jaw literally drop. With a confident air, Jay swung the door open and walked in, spilling his copies on the kitchen island for Mrs. Bagwell's review.

He simply looked at her, and said, "Yeah...it's me."

Without waiting for her response, Jay walked right past her, and to the refrigerator. Opening it like it was his, he looked around, wanting a beer. "Yeah, Mrs. Bagwell, I gotta say, you sure fucked up. I mean BIG time." Seeing one, he grabbed it and swung the door shut. She was still looking at him in shocked disbelief, so he continued. "Now, if MISTER Bagwell sees those," he said, gesturing towards the prints on the counter as he cracked open the beer, "well, let's just say that divorce is very much in your future. I'd HATE to see that happen to such a nice couple," and took a loud sip, as he reclined on a barstool.

Julie was beyond floored, and just did not know what to say. She had figured it was maybe another realtor, or some sleazy private eye--but the kid next door? What's more, the kid showed up like he owned the place, clearly underage and drinking a beer...her beer!

"What the HELL do you think you're doing?" Julie exclaimed

"Why, I'm just settling in," Jay replied flatly. "Look, I know you think I'm just the kid next door, the one you use for shit-jobs, but I also know what I've got here...This could ruin you, MRS. Bagwell..."

Julie blinked. Damn kid was smarter than she gave him credit for. "Umm...Look, Jay...You-uh...you're right, but we can fix this, I've got cash--"

"No, I'm afraid that just will not do it..." Jay said, as he cut her off, "I'm fine on the cash front," and smiled.

"Well, umm... Uh--okay," Julie responded timidly. "Jay," she said, as she opened the envelope, "it's several thou--"

"I said NO," Jay said forcefully, "but I have got something in mind."

'Oh SHIT' Julie thought, and held out the cash. "But Jay..." she said, as her voice trailed.

Swatting the envelope onto the counter, Jay said, "NO." Then added, "You THINK I'm an easy buy-off? You're wrong." With that, he popped his half-hard dick, out of his pants. Seeing Mrs. Bagwell's eyes pop out, he quickly said, "This is what I want, and for the next week plus, while I'm still here, you're going to get to know this part of me real well..."

Seeing her start to step back, Jay grabbed her wrist and said, "Look woman, you leave, you walk away from THIS," Jay said, shaking his dick for effect, "and you walk away from all you have worked for." And with that, Jay shifted a bit, his pecker stiffer.

Julie was at a total loss; she did not know what to do...so she stood there, literally frozen.

It was working, Jay thought, she was doing exactly what he wanted, this whole confidence thing was by no means bullshit! Tugging her wrist, she took a step closer, and he placed her hand on his stiff cock. "So here's what you are going to--ahh--do," Jay said. "You are going to get to know this part of me, and I am going to get to know you, reeeeal well..." Jay noticed that Julie naturally started to stroke his dick, and it certainly felt good. "Yesss..." he cooed, "you just do that..." and kept eye contact with this woman, as she stroked his throbbing cock. He noticed she seemed to naturally give it a bit of a 'squeeze.' No girl had ever done that, and he liked it.

Julie just stood there, but her mind was racing 'WTF are you doing!!!' said part of her, while the other half of her was just going with it. Julie knew, all too well, what was at stake here, and it was a lot more than just giving the boy next door a hand job. Well, he was technically a young man, as she knew him to be eighteen, exactly half her age, plus a year or two--ahem. She noticed that for a kid, his cock was not bad, and she found herself giving it a natural squeeze. 'Damn that's firm,' she thought, then actually shook her head at the thought. Just as she was getting ready to speed up and get this over with, he pulled her hand off. 'Wha--???' then realized what was going on.

"Oh shit," she grumbled

"Oh shit, indeed," Jay replied, as he removed her hand from his now-fully-erect member, and walked over to the couch, his boner flopping, taking his beer with him. Setting the beer on the end table, Jay dropped his pants, and looked at his watch. "Well, MRS. Julie," he said, as he had a seat, "your hubby gets home early today, so you'd best get over here and get that mouth to work. I'd HATE for him to find out about your cheating ways..."

If there was one thing Julie Bagwell hated, it was giving oral sex. Actually, Julie had grown up quite the prude, and while her husband had opened her to many new sexual experiences, holding one in her mouth, much less getting a mouth or throat full, was NOT her cup of tea. She had heard that the roads to power took you to some unexpected places, but she never imagined this.

Her husband was only her third real sex partner, besides a few one night stands in college, and Derek, the man that this damn-kid caught her with, was the first man she'd EVER done anything like that with. At first, it seemed exciting, but Derek was a decade older than her, and really, it was over before it began; she was just starting to push back into him, and suddenly Derek had whipped out and squirted himself on her butt cheek. It got her on the coveted governance board, but she should have known things couldn't go THAT easy.

Julie walked over, kind of stilted, and kneeling, said in a meek voice, "But...Jay..."

"But nothing," Jay snapped back. "You're gonna suck this off, and thank me for it." He smiled, as he watched her bend to his will. "You made a mistake, and now you will pay the price." As she knelt in front of him, Jay added, "Let's get that shirt off, too; I want to see those knockers." As if to emphasize it, Jay slumped on the couch, serving his dick right up in front of her.

With a look that was similar to having to take bad medicine, Julie numbly pulled the shirt over her head. She was wearing a simple, cotton bra and her C-cup breasts with ample, dark areolas were clearly visible. At his gesture, she shuffled forward on her knees. The feel of the young man's hands squeezing her breasts and giving her nipples a tug, would have been welcomed, were they her husband's hands, but they weren't. She looked down at the large cock in her hand, and taking a deep breath, she exhaled, opened her mouth, and leaned forward, taking the first bit of him into her mouth. At least he smelled freshly showered, she thought.

Although she clearly did not want to have anything to do with a blowjob, she took to it pretty well, Jay thought. Jay had always 'lucked out' on the side of females that did not do oral, and today was the same, although he had to say that seeing this gorgeous woman with her lips locked on his Gila-Monster, was more than he could have hoped for. After about three good head bobs, she released it, and looked at him with pleading eyes. Jay instinctively moved his hand to the back of her head, but she really didn't require prompting; instead, opening her mouth, and keeping eye contact, held the shaft as she rubbed the underside of his head on her tongue, and that elicited a smiling groan.

Jay had read and watched enough porn to know what throat-fucking was. He had to admit, she was gorgeous, by far the best he'd ever had, and with only the slightest nudge, she took him back into her mouth again, this time adding suction. Jay groaned loudly at the feel of her lips moving up and down his shaft; it was incredible, and Jay narrowed his eyes, as he tried to hold on and make that feeling last.

Julie realized that now this kid was searching for the back of her throat. She knew there was no way she was going to take a blast of his goo without throwing up all over him and her leather couch, but she tried to relax, and just let things roll. Actually, it was almost as though this was all some kind of bad dream, and not really happening. She knew that if she just hung on and bought time, she'd figure a way out of this, and make this damn kid pay. But for now, her mouth would have to be what 'bought time.' Knowing that his head back in that soft part of her throat would make him blow, she had to do something, so she released and brought her mouth off him. She could feel his hand on the back of her head, so she turned her head sideways and, taking the side of his shaft onto her lips, she ran them down the length of him, then slowly back up, and took him back into her mouth again. Knowing he would try to go back to her throat, she did it again, hoping to excite him into cumming and getting out of this, if only for the moment.

Jay should really have kept his head about him and just enjoyed the moment. He knew she was clearly doing what needed to be done to get it over with, and he didn't blame her a bit. But he was enjoying having this woman, easily a fifteen on a ten-scale, blowing him. Like it or not, she was sucking him so hard, his knees could not have wrinkles. Twice, he had worked the head of his dick back into the soft area of her throat, and twice she had moved it out and licked his shaft. That part really did it for him. Had he been able to hold it in the back of her throat, he could have face pumped her for a long time, but the combination of her beauty, his success, and the moment, was catching up to him.

Julie could feel his dick starting to 'twitch' and already, he leaked some salty pre-cum, which had its own taste. She hated this, but even so, she had to admit the kid had a large piece of meat, and she was surprised she hadn't gagged on it sooner. When he had it in the back of her throat that last time, she felt some pre-cum leak, and started gagging just a bit. Were she not worried about her house, she would gladly have vomited on him, the smug little son of a bitch. His hips were pumping now, and she had to get him out of her mouth. She knew it wouldn't be much longer.

Jay let her take it into her mouth, then gripped the back of her neck. His dick was stuck in her cheek, pushing it out. That plus the drool on her chin was quite a sight. She looked really stressed, and that last time in her throat, she was starting to make gagging noises. While that excited him all the more, he figured she would barf or some stupid shit like that, if he throat-blasted her. She had a few fingers around the base, and was jacking him too, and that was just too-too much. Jay knew the hubby would home soon; so, as his hips began to convulse and pump, right on the edge of control (okay, a bit over it), he relaxed his grip. She immediately pulled him out...and then Jay held her fast, and promptly shot his wad on her face. Jay got her upper lip, nose, cheek, then streamed it off into her hair. Letting it drip down, he got her neck and upper chest for good measure, and smiled. Like it or not, she was then, clearly marked.

With a deep breath, Jay stood up, albeit a bit shaky. Already, she was wiping her face and coughing, no doubt cursing him under her breath, too. As he packed his wet junk away, he zipped up, and looked down at her, grinning. "Whelp, looks like we're off to a good start," he said.

Grabbing her shirt, Julie spat into it, and coughed. "Asshole...!" she said. Getting up, she then grumbled angrily, "You'd best forget about ever do--"

With a wave of his hand Jay interrupted her, speaking loudly, "SHUT UP, WOMAN," he replied. "While I'm here for the next week or so, we'll be doing what I want, when I want, as I want, for however long I want, got it?" Stepping across to the patio door, he then added, "Unless, you want to throw your life away. Your choice. But remember, my way is temporary, yours is permanent." Glancing out through the front room, "Good thing you got me off when you did, looks like Daddy's home. I'll be in touch." Jay burst out laughing, as Julie's eyes went wide. Just then, the garage door began opening, and Jay saw Julie running for the counter and the stairs.

Stepping casually out the patio door, Jay waited until he heard Mr. Bagwell heading up the stairs, calling for his wife. Jay then sauntered over to the low spot in the fence and hopped over, wondering if Julie was up there hiding and brushing her teeth. He was hardly in his house when his Mom pulled into the drive, as well. Jay was a decent cook and had promised Mom, so he went to wash up and then make dinner. After all, it would give him time to plan...and he had some really good ideas.

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