Jay's Milf

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!

***

It was with a sense of dread, that Julie drove home. Her normal workday was a half-day at the office, the rest either from home or on the road, so being out of touch was not unusual, and right now she truly regretted it. On her way home, she had gotten a text from her tormentor. 'You'll make time 2-5PM' was all it said.

The houses were just far away enough from each other, that Jay did not hear her car pull in at her house, but he was sure she was there. She was nothing, if not a creature of promptness and habit. After a quick test of the pinhole cameras and other hidden gear he had set up, and knowing she had been home for a bit, he texted her at 1:45pm, and said simply, 'Come over'.

He chuckled at her reply 'over there?' to which he in turn responded, 'No, the Fucking courthouse. Here NOW. Do as told'.

At exactly two o'clock, Jay saw a shadow at the side porch. Opening the door, he could sense the attitude in the air. "Come in," he said, with a knowing smile.

Julie was not one to be bossed about by any man, much less one young enough to be her kid. On the other hand, she could not piss him off either. "Look, Jay, I've thought about this and I'm not--"

"WOMAN," Jay responded firmly, cutting her off. Then, in a calmer tone, said, "Look, Julie, if you don't like this arrangement, then you feel free to end it. I'll send off the info I have to your husband, along with a contact I have at the local paper, and also to a few reporters at two of the local TV stations, and you can take your chances. I'm sure nothing will come of it." He ended it with a sneer.

Seeing her hang her head, Jay countered, "Here's how it is. I am stuck here for the next week or so, then I am outta here, so tell you what. You just do what I want, when I want, as I want, like yesterday, and when I'm gone, I turn it all over to you to destroy. I'm out of your life, forever."

Julie had at least a window, an end point that she could see, and that was better than nothing. She allowed herself to be led upstairs, and in the process, just sort of numbed out. Damn kid was saying something about the house, hell, she didn't know or care. Would have been different were she single or in a bad marriage, but neither was the case, and the thought of having to suck dick again just mortified her. But she tuned in when she realized they were making their way to his room.

Jay led his little prize into his room. It was, actually, a rather unremarkable room. "I know," he said. "As soon as I got ready to move out for school, they turned MY room into a home office, so I have this guest room, but it's not too bad." The room had a twin-size bed with lattice head and foot boards, that sported extended balusters, and a matching solid-oak dresser, that was actually quite nice. Off to the side of that, was a gaming console, flat screen, and a chair. Seeing the look on her face, Jay sat in the chair across from the bed, and positioning her in front of him, he sat in the gaming chair. As he did so, he discreetly bumped a remote, he had concealed under the chair. Keeping eye contact, Jay said quietly, "Remember Julie, I keep my bargains, and the bargain I made is one-plus week of 'fun', hmm?" Seeing her give an almost imperceptible nod, he smiled, "Okay, Julie...good. Today is going to be very different from yesterday, you'll see. Let's start by having you undress, down to your underwear, right here in front of me. Now get started."

Julie had to admit that, were it her husband, or rather were it done another way, it would have been sweet, the way she was swept up the stairs, and spoken to in such a calming voice. It was not how she was used to being treated. No...it was that she was being forced, that is what it was. Be that as it may, she knew she had to go with it; so, she maintained her composure. Looking over the boy, as though he were not there, she unbuttoned her pants, then untucked her shirt, and pulled it over her head, to reveal a soft cotton bra with a light floral print. She accepted his hand, as she stepped out of her shoes--how odd it was, that he was being nice about this--keeping her steady. She really didn't mind, as he turned her, so that she showed off her behind as she lowered her pants, then stepped out of them.

She kept herself mentally 'separated' as the boy guided her, and then, she did basically the same for him. He was obviously working out, and was on the verge of getting a great bod. Still some pudge, but not bad, really. She was thankful that he did not have her linger at his waist, as she knelt and removed his boxers. The kid did have a decent-sized dick, and she figured that was what today would be about. Again, she kept that distance, as she felt him remove the last bits of clothing from her, and they both stood naked. Julie's gym time meant she knew she had a great body for a woman of her age, and by the angle of his stiffy, she figured he knew it, too.

In Basic Philosophy, Jay had learned that all people were naturally submissive, and by taking his 'air of aggression', Jay was finding this to be the case. "On the bed, on your back, across the middle," he said, in a blunt, matter-of-fact manner, and liked that she naturally did it. Shifting a standing mirror to the far side of the bed, Jay then took a robe sash from under the bed, and using a simple knot from his Boy Scout days, wrapped Julie's hands together at the wrists. "Don't worry..." Jay said, with a sly grin, pulled her hands back and over her head, and quickly tied them off. She was then, where he wanted her--lying across the bed, her calves and feet hanging off the edge, unable to touch the floor.

Julie had a small panic attack, as she was tied to the bed. She and David had done this before and she liked it, but this was not David, and she was not expecting 'The Kid' to do this. Julie closed her eyes, and tried to relax, and she admitted to herself that it helped that he was now very gently touching her, running his fingers along her thighs, her sides, her shoulders, in an almost-tickling fashion. She did admit it felt good, and she liked that he did this with her breasts, squeezing and lightly tugging her nipples, something her husband never did. Again, were the situation different, she would be into this, and Julie was pushing that feeling out of her mind, when Jay spoke.

"Well, Pet," Jay cooed softly, "I have to say, this is one sexy body..." As he said that, he added some light kisses. Her erect nipples had not escaped his eye, so Jay took a moment to take one in his mouth. He heard her gasp, as he enjoyed suckling it for a moment, teasing it with his tongue, then he released it, and stood, noting her eyes popped open, watching him. Jay smiled widely, and said, "Well, Pet, yesterday was most assuredly about me and my fun, but today, well...it's still my fun," and Jay removed a Hitachi wand from his dresser. "But, I'm gonna have it with your body." Waving the Hitachi, he added, "Like the new toy, Toy?"

'OH, SHIT' Julie thought. While she had accepted that she was going to have to let him violate her, she had promised herself that she was not going to cum for the kid...and now this. She then realized she had truly underestimated him. The only thing she could do, was to look at Jay, who she was now thinking of as the kid 'The Kid', and with a pleading look said, "Jay..."

Jay still held a second sash, and this one he used to tie her leg just above the knee opposite him, then tied that to the footboard. Ignoring her pleading look, Jay said, "Pet...yesterday, we got to see my orgasm. Now, I want to see yours." Giving her a tug towards him, pulling the tied leg away, and kneeling at the edge of the bed, Jay had a fully-unobstructed view of her pussy. Flipping on the Hitachi, Jay ran his finger smoothly and lightly up the inside of her thigh, then across and through her pubic hair, the Hitachi in the other hand following along. Making eye contact, he smiled and cooed, "Now, I want my Pet to enjoy this..." and taking the Hitachi, he touched it to the base of her pussy and moved it up towards her clit. Reaching that, he began a series of slow, light circles. The effect was not long in coming.

Julie's senses were peaked by the application of the Hitachi, despite her best efforts not to be. The tease along her thighs and through her pubes was erotic, and she felt herself tense. 'Damn that kid's hide,' she thought, then pushed it out of her head. She tugged her leg against the binds, but they held, and he had a firm grasp on her 'free' leg. It oddly excited her? Then, it was time and she gasped hard, as she felt it touch her vagina; in fact, it made her grunt. Then, the feel of it moving up made her squirm; her body was beginning to 'flow' against her will--pulling against her bound arms, only made it worse...and excited her at the same time.

"Nuh--NO!" she found herself saying, "J-Jay..please..."

Jay smiled wickedly and raised his head just a bit, looking down at his Toy. Julie Bagwell's body was reacting to the stimulus now, and a forced orgasm was inevitable, it was all biology then, and he knew it. Continuing to make those circles, he noticed that the wand had a 'wet' sound at the bottom, and at her clit, Julie was furrowing her brow and emitting whimpering sounds. She had her chin tucked, and her eyes closed, but still, he could see her body tensing and releasing as he worked up and down...up and down. Her mouth was open and she was panting, too. As if to emphasize who was in control, Jay abruptly pulled the wand away. Seeing her eyes fly open, Jay grinned, flashing his teeth...and started the whole process over again. She was at his mercy, and Jay was in no mood to show mercy. After all, they had at least two hours yet.

Julie was fighting her body's responses, but it was a losing battle. 'DAMN HIM,' she thought, would it be different if he hadn't actually been caring and sweet? 'Damn this kid.' She wanted to remain 'pure' to her husband, but this felt so good. Her eyes were clamped shut, but damn the feeling of the Hitachi on her was just too much. 'How did he know she had one of her own? He couldn't--who is making that noise?' she thought, only to realize it was HER. She was, at first, making a whimpering sound, but it had become a moan.

"Ohhhh...GAH..." she uttered. The start and stop was only making it worse, and when she pulled against her bonds, it was that much more of a turn-on. She was panting and moaning loudly--no, she couldn't take it. When Julie heard her own wetness on the wand, she surrendered, and trying vainly to tuck in, she finally released her orgasm, accentuated with a deep, "Aaah--Uugghhh..." And ending with a whimper.

It was over, The Kid had won. She, at last, opened her eyes, panting heavily. Looking down, she could see her chest heaving, sweat on her breasts. She looked at her tormentor with burning anger. 'You won. Damn, you,' she thought, 'but it's over.' His dick was erect and looked to be red, and she knew what was next. It was only then that she felt his hand slide up and take her breast in hand, then he lowered his mouth to suckle it. In her heightened state, it felt great, and she tried to push that aside...it was only then she realized, to her shock, it was not over, NOT at all.

Seeing her try to 'hide' her orgasm just made Jay realize that this was something he had to push through, just as he had read; so pushing through was exactly what he planned to do there. Her nipple was instantly hard in his mouth, so he knew he was onto something, he just had to see where it would go. Setting the wand aside, Jay returned to lightly tracing Julie's body. "Now, Julie, that was good...very good," he said through his evil grin. "But, not good enough. So, we're going to do it again." Seeing her eyes widen, Jay slid his fingers along the inside of her thigh, lightly touching her vaginal lips, causing Julie to gasp. "That's right, I want a second orgasm, and for this one, Pet, I want to hear you scream, got that?" Jay flipped on the wand, but left it where it was. Instead, he slid his fingers inside Julie, right over her sensitive lips. Hearing her groan and protest, he responded the best way possible--he plunged his face directly on to her hot, sensitive, totally-soaked cunt.

When Julie heard 'Again', she was without thought or words. Julie had never had anyone try to garner more than one orgasm out of her--she wasn't even sure if she could do it; yet, there she was. She had expected to have to accept his dick, but in response, before she really had time to process the info, her body tensed as a pair of fingers pushed past her labia, her sensitive lips, and deep inside her. It caused her to groan loudly, and she felt her thighs naturally 'open' to the fingers, her body was fully betraying her! Just when she was about to protest, The Kid plunged his face onto her. As she felt his fingers expand inside her, The Kid used his tongue to make one looong LICK up her labia, to which she cried aloud, and just as with her nipples, The Kid took her clit into her mouth and suckled it. THAT caused her to arch her back, pushing her breasts towards the ceiling, and pull HARD against her bonds. An absolute yell came from deep in her lungs, and again her thighs opened, wanting more.

The fingers were pumping in and out of her; The Kid was holding her pussy in his mouth, and she was a writhing, moaning mess. A bit ago the hand not inside her had pulled away, and was holding her hips still. Then, she heard it, it was another buzz. Looking down, she saw Jay smiling at her, his mouth and face wet, and not all of it was sweat. He was holding a pink, vibrating 'egg' on a cord. Julie tried to put her hand down as to indicate 'no', but he smiled, suckled one of his fingers, and with that, she felt the vibrating egg enter her body. With a "N-No--oh! Ahhh..." she felt it enter her and again, those lovely fingers pushed it deep into her, guiding the egg. Julie was gasping and panting; she looked to the side, and saw her face in the mirror. It was totally soaked in sweat, and wracked with LUST. Although her clit had been initially numb, that was long gone, and she could now feel it. Yes, that was it, a giant, massive wave building within her. Part of her felt shame; her body was betraying her--and at the touch of another man. But a bigger part, the part taking over, was all about the 'wave'. She WAS multi-orgasmic, and what's more, she was about to, and did not want to stop it.

'Damn, she tastes great,' Jay thought. This woman was about a fifteen on a ten-scale, and Jay was getting ready to make her cum a second time. Jay didn't really have much experience with intercourse, but his 'head game was on point,' as one former girlfriend had told him. That, plus the knowledge that this was the only time he would get THIS opportunity in his life, fucking a model-quality woman of this caliber, meant he had to make the most of this opportunity while it lasted. When Jay had his fingers inside her, he expanded and wriggled them, and when he was slow-pumping, his fingers were together on entry, expand, twist, and withdraw, then repeat. And boy, was it ever working. Guiding that electric egg in was just the next step, and he could tell she was about to do it again. For someone so reluctant, she was certainly getting into it, so he kept at it. Again, her hips were starting to make that odd little 'tuck' from earlier, and her breath was shorter. Yeah, she was close. With one final LICK he put his fingers together and, lifting up a bit, at last made eye contact with his fuck-toy. She had that lost, pleading look again, but this time, tinged with lust--she had to be on the edge. His fingers picked up the rhythm to a furious pace, and he cooed, "Cum, Julie...CUM..." and THAT did it.

Jay was honestly surprised, as Julie Bagwell pulled HARD against her bonds, and arching her back to its fullest, she raised her hips in a yoga 'bridge-like' position, but with it, she emanated a piercing, wailing scream. "AAAHHH, JAAAY! -- OH, GAAAHHH...!" then fell back to the bed, a heaping, twitching mess. Jay knew that 'aftershock' twitch thing meant he had maxed her out, as it were--too bad, as he had yet to get off. Or...perhaps too good.

Jay told her how good that was, as he eased the egg out. He also untied her, and rolled her onto her tummy. He took several minutes to rub her shoulders and biceps, having spent nearly an hour restrained like that. Kissing her lightly down her back, Jay stopped and rubbed her sexy ass. His toy was laying there panting, almost wheezing. "Now, Pet..." Jay said softly, "You didn't know you were 'multi' did you?" he asked. Running his hand across her butt, he ever so gently tugged it open, so he could see her dull pink pussy, and added, "Now, this space at the top of your legs, that makes this little window? Day-umm....I love that, and..." And as he said that, he rubbed a little deeper, almost at her vaginal opening said, "I am going to have that," and as he said it, he rolled her gently onto her back. "Right now..."

Standing at the edge of the bed, he lifted her hips and pulled her to the edge, and lifting her ankles to touch his chest, he placed the head of his large, throbbing dick so that his head was just rubbing her pubes, then gave it a few 'taps' on her clit, which made her whimper. Guiding it down, parting her labia, he looked up, had solid eye contact, and whispered, "My turn," and pushed slowly into her, watching her face change, as her incredibly-hot wetness opened to accept him.

Julie, she was no expert, but she found Jay's dick to be neither the largest nor the smallest she'd had, but--DAY-UM--his presentation was on point! Her pussy was incredibly sensitive, and she was still coming down off the high of a second orgasm, but The Kid, damn his hide, DID manage to push all the right buttons. He could have just flopped her over on her stomach and pounded her out, but the way he took that bit of time before made all the difference. The part about keeping eye contact didn't hurt a bit, either.

Now she was on her back, and her ankles on The Kid's shoulders, and his very satisfying dick was sliding in and out of her. The Kid had long since won this round, she was totally submissive to him; yet, she was still super-sensitive. She was moaning because The Kid would thrust into her, then do this 'grind' thing, that would make her moan, then go back to thrusting, then grinding. With each hand squeezing a breast, she was really enjoying the ride...'Holy Shit', she thought, 'a third time?' She wasn't sure if that was really possible, and so as The Kid was thrusting into her, she put her hand on his stomach and said, "Jay, softer...Not, ah, so damn, ah, hard...ah, soft... er..."

To that, The Kid changed up his game. Grabbing an ankle in each hand, he stretched her legs wide apart, her legs outstretched as far as possible, and this just served to rub her sensitive pussy lips on him even more.

"UGGHH!" she called out.

The Kid smiled, resumed his merciless pounding, and Julie's face was red and grimaced; with each thrust, as he pushed into her, she tucked her chin and whimpered loudly. His speed was really picking up, she really hoped he was close.

"UUGGHH, JAAAY! UUGGHH--DAMN-- JAAAY!" she yelled, she felt like she was going to cum a third time, and then was nearly crying.

Then, it was Jay's turn to lose it, and he surely was. Fucking this gorgeous woman's cunt until she was screaming his name while red-faced, all from his pumping, pushed him over the edge. He should have lasted longer, but it was no use. He was there, he was going over the edge. Pulling himself out at the last possible moment, he proceeded to let his balls dump several thick, gooey ropes of ejaculate on Julie's pubic hair, breasts and stomach. It was a fine sight, covering her like that...A tiny bit might have gotten in her hair; to Jay, it felt like it shot out hard enough to chip the paint off the walls.