Holly Blackmailed

This is a work of complete fiction aided by an imagination you all wish you could have. Hahaha! All characters are fictional. Any resemblance to persons alive or dead is purely coincidental. All incidents described within are fictional.

*****

She gave into the threat again. Again.

Holly had never stopped to count the number of times she'd been forced to fuck some guy while John watched, but it must have been about eight guys. Probably more. There had likely been a handful of guys which she'd been successful in removing from her memory.

Their affair had started about ten years prior. She was married; John was single. They met at work, started flirting, then fucking, then proclamations of love. When John suggested a threesome - "Nothing gay, just me and another guy doing you" - she was hesitant. Very hesitant. But eventually he wore her down.

John had grand ideas about how it would go. Just like a porn scene. Wrong. Holly wasn't a hungry slut like in those videos. And the guy shot his load too quick and then couldn't get it back up.

Consequently, he had to talk her (beg her?) into doing another one. But she refused. More begging did nothing. Holly still refused. More begging. More refusal. More pressure. Still more refusal.

He gave it a rest but his mind never let it go. He thought about it constantly. John loved the idea of watching Holly get fucked by someone she didn't know. She very much had the girl-next-door thing going on. Very attractive, very innocent way about her.

When they first started having sex, Holly had little idea how to give a blowjob. John had to coach her to her current level of awesome oral proficiency. She didn't love sucking cock, not by any means. But John asked for it enough and so Holly gave in. She pretty much had no choice but to be good at it.

She was what John called a "head sucker." Eventually, she became great at deepthroating.

Holly had no idea how to incorporate the use of her hands. It didn't take her long to learn to jerk John's cock while she worked it with her mouth.

Swallowing his cum, that took a little more work but eventually, she got that down, too (pun intended). John will always remember her first mouthful came in a little storage room atop the steps above the payroll department at work. Soon after, he was able to progress to cumming on her pretty face. Again, not her idea; another something she gave into.

It wasn't until Holly started wearing a thong and John seeing how good she looked that he had to have her in the ass. That took a lot of convincing, but, like everything else between them, she finally gave in. Before long, there were occasions when Holly got off taking it in the ass. Few things turned on John more than hearing her say, "Oh! Stick in my ass! I'm going to cum! Stick it in my ass!"

Ultimately, their relationship became one of John gently nudging her into things. Getting his way. It became all about simply wanting to fuck her brains out whenever possible.

Talking Holly into another threesome, however, was a tough go. John was getting nowhere with it. She reminded him of the video he shot during the threesome (again, he talked her into allowing video) and that he could watch it any time he wanted. Constant pressure from him failed. There was to be no second threesome.

Then came a shock John never expected: He busted her cheating on him. The innocent girl next door found a second guy, another co-worker, to cheat on her husband with.

It took John about a half day to realize two things.

First, his innocent girl next door was a slut. And he was turned on by it. He could make this work. Just you wait and see.

More importantly, despite being turned on by the "new" Holly, he was still angry at the betrayal. John wanted revenge. How dare she do this to him? He wanted to take his singular desire to fuck her brains out and get a large measure of revenge at the same time.

His method: "How about I show your husband some of that video of you fucking another guy? Think he'd find that interesting?"

Holly froze at the thought of it. She went into cornered animal mode. She tried to fight back. But he was able to counter everything she threw at him.

It took about a week of going back and forth but Holly knew she was beat. "Go ahead and tell him, I don't care!" gave way to a fear of divorce, her kids knowing what she did, embarrassment. The clincher was John's threat to tell her new lover's wife all about what was going on

John laid it out pretty concisely: "You and another guy. Whatever I say."

And so it began. With the first guy, John had her wear a blindfold. "Just for something different."

John laid out ground rules that would become familiar: "Don't be a lame fuck. Show me that you're into it. If you act like a bitch, then we'll both fuck your brains out and I'll still blow you up to your husband. You want that?"

With that as her motivation, Holly absolutely destroyed that first guy with her mouth. John couldn't believe it. Wearing the blindfold, Holly had no idea what the guy looked like, only that he had a cock slightly bigger than John's and he was vocal.

She put on a cocksucking clinic that amazed John. Holly used perfect combinations of jerking with her hand while she devoured the length of his hard cock, tonguing his balls and ultimately deepthroating him as he shot his load right into her throat. The guy talked to her the entire five minutes he lasted, telling her what to do, encouraging her, guiding her, applauding her, and ending with the announcement that he was about to shoot his load.

"There you go! Keep your mouth on it! Yeah! Take it! I'm gonna cum! Take it! Yeahhhhhhhhh!"

Holly worked the guy over so thoroughly that he couldn't get it up again. So John climbed up on her chest and fucked her mouth while the second guy, limp dick and all, tongued her pussy. John gave her another mouthful for her efforts.

She tried her best to forget the details of the men John had her fuck over the next two years. There was the guy who used the fingertips of his middle fingers to rub his own nipples. Despite Holly's pleas about having to go back to work afterward, he came on Holly's face for the big finish.

John brought back the guy with whom they did the very first threesome and he wore a leather device around his balls, which they thought that was a bit over the top. Nonetheless, there was no cumming early this time. John and Mr. Leather Balls fucked Holly for about an hour before they both finished on her chest.

There was the guy, Brad, who caught Holly off guard with a great mouth. He started with passionate kissing before going down over her throat and to her tits. John could tell by Holly's demeanor that she was entirely turned on by this guy.

When she got on her knees for him, she was not at all intimidated by the biggest cock she'd had so far. About eight inches of a thick, hard cock. Brad didn't last long, pulling out and shooting his load up to her chest and face before they could double her. There was some disappointment, but John was also really turned on at seeing Holly surprised by being turned on herself. Holly refused to admit later, of course, that the guy turned her on.

One guy, Steve, a Hispanic, was only two years older than Holly's oldest son. As usual, John was very direct with his warnings that she be a dynamite fuck and Holly did not disappoint.

John got some great video of her looking up at Steve with her pretty innocent-slutty face while she worked him over expertly with her mouth.

It was for this threesome that, much to Holly's dismay, they worked her into taking them in the ass and pussy at the same time. That hour of fucking ending with Holly cupping her tits, just like John told her, while Steve jerked off on her pretty face.

There was a longer wait before the next threesome. John and Holly still met occasionally for sex but there were no threesomes for about six months.

The drought was broken when John told her that the next threesome would require a blindfold. "No problem," she thought. And there would be ass fucking.

"No way!" Holly said.

"I think you forget the spot you're in, dear Holly. Should we see what your husband thinks about it?"

A week later, remembering all the rules John stipulated, she arrived at the hotel wearing a short skirt and no panties. She took off her top and bra, put on the blindfold and climbed up on the bed.

"I'm ready!" she said as instructed, seemingly to no one.

The man came out of the bathroom finding her blindfolded and up on the bed on all fours, her ass alluringly in the air.

What Holly didn't know is that there was a reason for the blindfold. She knew this man.

Dan co-owned a small business in town with Holly's husband, Tyler. Holly had told John several stories over the years about her dislike for Dan. She just didn't like the guy. She thought he was arrogant, obnoxious and disrespectful to her.

It was no secret to Holly that the feeling was mutual. Dan saw the way Holly treated Tyler in front of others and grew an intense dislike of Holly. Simply put, she was a bitch. After witnessing many of these embarrassing episodes of treating Tyler like shit, Dan simply thought that she needed a good ass fucking to keep her in line. He never told Tyler that but he made it clear to Tyler that he shouldn't stand for that treatment.

The interesting thing about living in a small town is that everybody knows everybody. Not long after John's revenge threesomes of Holly started, he ran into Dan at a local bar. Their meandering discussion turned to Holly and Tyler and after a few drinks, John took the big risk of telling Dan about his affair with Holly.

Over the course of a few more months, John eventually convinced Dan that they could pull off him teaching her a lesson. It was a risk but John convinced Dan that Holly wasn't going to say anything to Tyler. Not with a divorce hanging in the balance. He knew John was right.

Dan agreed to do it but with the caveat that she wear a blindfold and there be no talking. He did not want Holly to know that it was him.

He was in the bathroom nervously awaiting her arrival. When he heard the door to the room open, his heart started racing and he got an erection so strong he was afraid he would cum. With Holly's "I'm ready!" he walked to the bed and quickly got out of his pants. Dan had seen Holly many times over the years, of course, but he had never seen her like this.

He knelt on the bed behind her and flipped her skirt up over her ass. No panties. "Oh man..." he thought.

Dan ran his fingers along her pussy. Clean shaved. "Oh my..."

He leaned forward putting his weight on his right hand and felt her tits. He spit-moistened his fingertips and ran them along her nipples, feeling them harden. He wanted to say something but the no talking stipulation was his own idea. So he stifled his urge to comment on her big tits.

At age 43 and with two kids, Holly's body wasn't what it was at 17, but it was awesome for 43. She worked out regularly, weights and cardio, and her only flaw was the bit of stomach paunch that she couldn't get rid of. And her chest was spectacular.

When she first told John that her chest was a 34FF, he didn't believe her until he saw it listed on her Victoria's Secret bra, which she filled out perfectly. John was always amazed at how perfectly her tits dropped. They weren't saggy like you'd expect from a 43-year old mother of two.

Still leaning over her, Dan mauled her tits with his left hand. His dick now rock hard, he absolutely could not believe that the woman he had grown to dislike so much was right here at his mercy. He guided her left nipple between his index and middle fingers on his left hand, right at the middle knuckles and squeezed.

Not expecting this, Holly's body jerked and she let out an audible breath in surprise. She wanted to tell him, "Not so hard!" but she remembered the no talking rule and was afraid of the consequences if she broke it.

Dan stopped squeezing her nipple and moved his hand to her other nipple, doing the same thing, this time with his thumb and index finger. Expecting it this time, she bit her lip and didn't react. He enjoyed another minute mauling her tits and then lifted himself back up so he was on his knees behind her.

He took his ridiculously hard cock and rubbed the slit of her pussy with it. Holly wasn't wet and Dan's initial reaction was simply to apply some spit. "Oh no. This bitch is getting it the hard way."

His left hand steadying his cock head to her pussy and his right hand on her hip, he thrust forward and pulled her back, entering a couple inches of his average six-inch cock into her. Not wanting to give away anything, he stifled an urge to moan. Holly, doing as she was told, merely bit her lip as he entered her.

Without waiting, he gave another quick hard thrust and buried his cock. This one surprised her and she let out a muffled "Ooof!" Turned on by her noise, Dan quickly held her at both hips and thrust into her hard and fast, pulling her back onto him, her pussy moistening with each thrust.

He mouthed a silent, "Oh my god..." and continued slamming his cock into her. After a good dozen thrusts into her, he gave her right ass cheek a hard slap for good measure. He was going to treat her the way he always thought she deserved to be treated. He couldn't believe he was given the opportunity.

What Dan didn't know - but Holly did - was the other rule John laid out for her. After about two minutes of taking his thrusts into her unwilling pussy, Holly said, "Fuck my ass!"

"There, I said, it," she thought to herself. "As ordered."

Taken off guard, Dan stopped thrusting into her. He felt like asking her to repeat what she'd said but he knew he heard her right.

"Ohhhhh," he thought as he dropped a gob of spit onto the fingers of his left hand, "you want a cock in your ass, bitch? I'll give you an ass fucking."

He slathered up his cock, especially the head, with the spit and rubbed some onto what he hoped was her tight little ass, too. Once everything seemed ready to go, Dan ran the length of his cock along her, like a batter taking warmup swings before the pitcher delivers. Then he guided his cock to her ass and pressed the tip to her. He knew it wouldn't just slide right in, even with the spit he lubed up with.

"Damn," Dan thought as her little hole resisted his entry.

"Maybe the fucker will give up," Holly said to herself hopefully.

He dropped some more spit onto the head of his cock and rubbed it into her. This time with some deft maneuvering, the head slipped in. She jerked forward slightly at the invasion into her ass. Dan moved his cock forward just a bit, kind of testing the water, making sure he was firmly in her. When he realized he was solidly in her ass, he slowly slid more in.

Holly had taken John in her ass probably ten times in the last year or so. She didn't love it, not even close. There were rare times when she got off from it, but it didn't happen anything close to regularly. She didn't think this would be one of those times either. Even the times when she did cum from an ass fucking, it was an intense, quick orgasm and then it hurt having the dick still fucking her ass.

Fortunately, Dan didn't have a big cock so taking him in the ass wasn't a big deal at the moment. She was a little surprised when he slipped it into her but she remained quiet when it happened. She just grit her teeth and put her head down.

Now Dan was going to give Holly what he knew she deserved. He really wished he could ask her what she had in her ass right now but he wanted to remain unknown to her. "You never know what could happen down the road if she knew it was me," he thought.

He grabbed both of her hips and gyrated his hips with his cock now fully in her ass. He loved the idea of his balls slapping up against her empty pussy. He withdrew his cock about halfway and plunged back into her.

"Geezuz... so tight," he thought. "Try not to cum."

He spat down another gob of spit for lubrication and pulled her ass back on him and quickly drove his cock forward.

"Ooofff!" she let out; she couldn't help it. The quickness - the harshness - of the thrust caught her off guard.

Dan started a fast rhythmic pounding of his cock into Holly's ass, her body lurching forward a little bit with each thrust. He used his knees to force her knees apart a little bit more, which stuck her ass up in the air just a tad more. It turned him on even more seeing her ass hiked up like that. Dan swore that it let him drive his cock in even deeper.

Spurred on by the memory of how much of a bitch she was to Tyler, he slapped her ass again in the same spot where his last one left a red mark in roughly the shape of a hand. Then he reached down with his right hand, grabbed her hair, being careful not to upset the blindfold around her head, and jerked her head back.

An "Ow!" escaped her lips followed by an "Oh!" as her body continued to be rocked forward from Dan's thrusts. The sound of his pelvis smacking against her ass filled the room. Dan was dying to ask her how she liked his cock fucking her ass but again stuck to the original plan of silence.

Dan let go of Holly's hair and continued fucking her ass, driving his cock to the hilt each time, adding a little more spit frequently. At one point when he felt an orgasm bubbling up, he stopped thrusting into her and leaned forward again to maul her tits one more time, pinching her left nipple between his thumb and index finger. She jerked her body to the right a little, hoping whoever this was would get the idea and stop. The only stopping Dan did was to jerk her by the hair again, kind of to show her who was in charge. He jerked her head once... and then again.

Holly let out a hissing sound of displeasure, knowing she was breaking the rule, but she couldn't help it.

She welcomed the break her ass was getting but she could have done without what he was doing to her tits. Dan alternated between groping the big chest he had always wondered about and squeezing her nipple between his fingers. Once he felt he could resume without cumming right away, he got back upright and worked the head of his cock up against her tight little hole again. He spit-moistened again and drove forward.

"Mmmfffff!" Holly let out as she felt his cock slide in and his balls slap against her pussy.

With his cock fully buried in Holly's ass, he leaned forward to grab her left wrist. He brought it up behind her back, awkwardly bending her elbow. The move surprised her and she fell a little to her left side.

"Oh! Ow!"

Holding her left wrist in place, he grabbed her right wrist and put it next to her other one. He then moved her wrists up her back a little bit to make it hard for her to move them. With her head now on the mattress looking to the left, and her arms wrenched behind her back, he resumed fucking her ass.

She uttered another muffled, "Ooomf!" on his first thrust and a "Errrr!" on his second. With her head down on the mattress, her ass was now stuck right up in the air. Dan knew he wouldn't last much longer and resumed his rhythmic fucking. Fast, hard thrusts as he held her arms in place.

Holly said "Ow!" a few more times and he took pity on her, releasing her arms. She propped herself back up on her hands and Dan gripped her hips again, gaining leverage with his thrusting. Her body was rocked forward with each thrust and Dan did everything he could not to utter a sound.

He reached his left hand around between her legs and found her clit. He used his middle finger to rub it in circles as he drove his cock in and out of her ass, albeit with a little less force given his hunched over position. Dan then drove two fingers into her pussy and Holly let out another soft "Ooomff!"