MILFY, Chocolate and Friends

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Jilly's careless email lands her in trouble.
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Silfy69
Silfy69
218 Followers

Routine. It was always a hard thing for Jilly to stick to. She had, she realised, always sought out 'the next thing', never able to settle on something, with something or with someone.

She had been seeing her well endowed Big Black Cock lover for a few months. Through their love-making, he had taken her to places that she hadn't ever dared believe could possibly exist in this human world. His cock had been so huge that, had it attached itself to her in the dead of night, she'd have sworn it belonged to an extra terrestrial rapist.

Over this period she had sucked, ridden and generally man-handled his cock with lust and with a ferocity she'd never known before, never tiring of watching it grow in her hands, of watching his cum spraying her body or feeling his hot seed spilling into every available orifice, hot and sticky.

Every time was breathtaking. Every time she would cum hard, desperate, marvelling at his chiselled body, his iron buttocks and his ram rod cock.

They'd experimented a lot and though Chocolate (her lover's pseudonym - his real name was Daniel) was a little trepidatious at times, particularly when she'd suggested wearing a strap on and fucking HIS arse for a change, they had both at least tried everything that the other had suggested (or more accurately for Jilly, she had just allowed her muscular lover to manhandle her into impossible positions or had done her best to take as much of his cock in her mouth as was humanly possible.)

He was an animal in the bedroom, throwing her around like a rag-doll, her tiny frame straining every sinew as she struggled to cope with his onslaught. She had loved it all.

But there was something missing.

Whereas they were as one in the bedroom, they were different everywhere else.

There was the obvious age gap which seemed to bother Jilly more than Daniel. He would have been happy to parade her in town, dressed in her shortest outfit and highest heels. He loved the thought of pimping her out, knowing that she'd return to him after a night out, ready to be hammered again and again; to 'punish her' for daring to be chatted up by other blokes. For Jilly, the age gap wasn't about insecurity but probably came from her strict upbringing. It wasn't 'right' to have a young man as one's partner. And it CERTAINLY wasn't right to have a young, black man. Her mother would turn in her grave.

Jilly wasn't racist; far from it. In fact, she had developed such an acute taste for black men that she could have been accused of inverted racism as her white male partners couldn't hope to compete against King-Dong-Daniel.

But there was also a social gap. Again, this didn't matter when they were fucking, but increasingly there were times in between where they'd talk and Jilly's acute sense of 'wrong-doing' would raise its head. They didn't understand one another's popular references as they were from two different generations. Jilly accepted that they were fuck-buddies but something was troubling her and she knew what it probably was.

Routine.

When she'd first met him, he had left her battered and bruised with the sheer ferocity of his attentions. His powers of recovery had been incredible and she'd lapped it up, delighted with her new, black toy boy. At that time she felt that 'routine' was a word that would never be used to describe their physical relationship as he took her to ever higher peaks. But she now felt it keenly. It wasn't boredom, it was routine. There was no danger anymore. They knew each other well enough to know which buttons to press but sometimes she felt she needed to be challenged NOT to orgasm by being roughly fumbled with rather than Daniel's expert touch. She knew that sounded ridiculous and she genuinely started to wonder whether there was something wrong with her; that she'd never truly be happy or satisfied. Like a drug addict, she'd always be looking for the next hit. She knew what had gone wrong. Availability. Daniel was always available. If she called or emailed, he'd be at her door within the hour, his cock hard and ready. If he'd been a little more untouchable...

Jilly did have someone in whom she confided everything. It was an old boyfriend who she had loved deeply. His situation - married - meant that he was unavailable from one six month period to the next. If she thought about him and about their love making, he wasn't as athletic as Daniel or as well endowed but the difference was...something. An 'X' Factor. Perhaps that was what love was but she'd dismiss her emotion as being too sentimental. Besides, he was unavailable (and that, she thought, was what made him so attractive.) Her life would be spent seeking out physical pleasures and she'd forget anything more meaningful. She was Jilly. And she did as she pleased.

However, they emailed constantly and he loved to hear of her sexual exploits. She had regaled him with many, if not all, of her moments with Daniel. Her old boyfriend loved photographing her and had been there at Jilly and Daniel's first meeting, snapping 'the chase' and posting the pictures for her and him to drool over.

After a few months of her relationship with Daniel, she decided to pour her heart out to her old boyfriend. She didn't like to burden him with anything preferring to play the part of the cock hungry seductress, but she wrote to him and told him her feelings.

Dear X

I'm feeling a little lost at the moment. As you know, my pussy has been constantly bruised and puffy with the onslaught of my young admirer! (Still got it!) As I've said before, he's very eager and very athletic and he's constantly 'down to fuck' (as the modern parlance would have it!) He can go for hours (and as you know, I just love to be desired and fucked for hours.) In fact, the more familiar I become to him, the longer he can go. And it only takes a small amount of teasing and he's ready again. Oh to be young again, eh?

But X, I'm starting to get a little jaded about the whole thing. He's very good at what he does but a) there's nothing more going on up top (at least, not that I've seen) and b) the urgency and danger of the first time has never been matched. It's as though I'm looking to be taken outside of my comfort zone; scared even. I know, I'm weird! LOL! I'm thinking of letting him go but his cock is good and I fear I'd miss it, but by the same token I'm not sure having a monster cock is enough for this MILF!!

He's quite a sweet boy, but he doesn't have your class, intelligence or understanding of the finer things. His brain is his cock and his cock is his brain! I remember telling him that he, like most men of his age, were dogs and that women merely had to throw them a stick for them to come running. I fear that was truer than I really thought.

The message went on to talk about other things that her and her forbidden boyfriend had shared over the years, including reminiscing about a threesome they'd once had, a swingers' party they'd attended and other defining moments of their affair.

Jilly was thinking about Daniel as she wrote it, wondering if things would have been different had she been born later; nearer to his age or whether they were just incompatible.

Absently, she began to fill out the 'Send To' box and was so distracted with her thoughts that she typed in Daniel's email, quickly clicking on the auto-completed name that appeared and without batting an eyelid, pressed 'send'.

She shut her laptop and went to pull on her gym gear to work off her frustrations at her lunchtime workout class, not yet realising that she'd unleashed a chain of events that would take her very MUCH out of her comfort zone.

*********

Ping!

Daniel 'Chocolate Blue Eyez' smiled as he looked down at his phone. The first few lines showed that this was a message from his MILF lover, a woman who loved to fuck and who had a bottomless pit of filth in her mind when it came to getting more black cock.

He was out of the office, on his lunch break. He found a bench. It wasn't sunny but it was warm enough to sit out.

He opened the email and started to read.

Daniel read the email through, slowing down as she realised what was being said; staring at his phone in growing disbelief and a steadily boiling sense of anger.

"Fucking Bitch!" He said, loud enough to be chastised by a passing OAP.

He looked around seeing nothing but red mist.

She had shouted and screamed as he'd fucked her. She'd said he was the greatest thing to have happened to her and that his cock was a work of art. She'd even taken time to photograph it, telling him she wanted to get a print of it for her wall. But that, it appeared, was the beginning and end of it, wasn't it? He was the archetypal 'piece of black meat'. As far as she was concerned he was good for three things and they were all sex!

She'd said she wanted to keep her private life separate from her social life so she'd resisted his idea to go out and about in town. He'd assumed it was the age thing. It now appeared it was the social class thing; the intelligence thing; the black thing. On the one hand he was 'best in show', on the other he was scum.

"Fucking, fucking Bitch!!" He said again.

He stewed all afternoon at his office, not knowing what to do. He'd decided not to respond with a terse email as he fully expected a grovelling apology when she realised her mistake but none came. That evening, he went home and went straight to the gym, taking out his frustrations and anger on the machines. His friends were there and noticed his workout intensity.

"Whoah!! You look like you're planning on bursting your vest open like the Hulk, D-Boy!" Said one, a fellow muscleman named Denny.

Denny had been a gym goer since before Daniel had started and was built the way proper bodybuilders were meant to look. He was rippled and veiny and had shaved his head some months before to add to his own bodybuilding mystique. Denny was adamant that he didn't take steroids but his wide eyed aggression betrayed his abuse of 'sports' medication'. If the conversation ever turned in a direction that Denny didn't like, everyone at the gym knew that it was best to back down or steer the conversation away. Ironically, thought Daniel, Denny was the type of guy that his MILFY would go for and yet even he had to admit that Denny was also the kind of guy she'd described in her condescending email (no'... class, intelligence or understanding...') This got Daniel mad all over again.

"Yeah, I'm feeling a bit tense, Den. Fucking women!"

Daniel had only made very indirect reference to his MILF mistress. He'd told 'the guys' about an insatiable woman he was seeing just for fun. He knew they'd been jealous but as with all blokes, they didn't want to appear too interested, or more correctly, wanted to appear as sexually virulent as each other. Now that Daniel thought about it, they probably didn't believe this woman existed.

Another of their gang came over and they nodded a greeting.

Rick was a white guy from Eastern Europe; Poland, Daniel remembered. Tall (6ft 5inches) and muscular, he was an imposing figure and had a strong jawline. He was okay-looking in a very dangerous way. Daniel was always careful not to give too much away in front of Rick as he didn't completely trust him or his morals even though it had been Rick who had helped his 'wood' the first time he'd met with his Milfy.

Rick, as with Denny, had shaved his head but his hair seemed to grow back so quickly that he always seemed to have a five o'clock shadow. He wore loose vest tops and he clearly kept his chest closely shaved too. Daniel assumed that all the guys at the gym had groomed themselves everywhere. Daniel had anyway. It was the porno thing. There weren't any porno stars, male or female, with public hair anymore, and every man at the gym, whether he knew it or not, believed he was capable of being a porn star.

"Dan's having trouble with a girl, Rick!" said Denny.

"Slap her shit up. Tell her we fucking come and fuck her fucking shit up if she don't fucking get it right yes?"

Rick's pigeon English made him sound like a character from a sitcom, but no one dared laugh at his sparkling turn of phrase in case he unleashed his bubbling, testosterone fuelled, East European temper.

"Rick's right. Bitches need to be fucking shown who's fucking boss."

"She fuck you up? If you don't fucking care for bitch, we fucking arrive as riot squad and fuck her shit up, you understand? One in here, one in here and one in her mouth. She won't scream with cock in mouth, yes?"

Daniel smiled, lost for a moment in the thought of 'fucking her shit up.'

"You know lads. I think you may be on to something!"

Over the course of the next 40 minutes, they trained hard but they plotted harder.

***********

It was a day and a half since the email had arrived and Jilly the MILF and Daniel hadn't been in contact.

An email arrived from Daniel/Chocolate, suggesting that he would come round for an evening of debauched sexual activity.

Usually, Daniel would text her when he was close by and she would leave the front door unlatched. He would come in and find her, sprawled on the bed, usually dressed in a rip-able item of clothing and high heels and they would go at it hammer and tongs for an hour or two (or three) after which Daniel would let himself out and his Milfy would shower and asses the damage to her bruised orifices.

However, Chocolate Blue Eyez had sent a text and an email saying that he wanted to recreate a little more of their first encounter. He told her he wanted to see her on the road so that it would feel more like he was a Black Stud who had spotted a 'victim' on the street and was going to get his kicks from a MILF slut, regardless. Jilly responded enthusiastically, liking the idea of changing things a little to keep their sexual encounters fresh. Plus she loved showing off her body. She loved watching the men's eyes visually devouring her curves.

'Go in to the park via the middle gate, come down the hill to the pond area. Walk once around the pond once and then exit the via the corner gate and then walk back up your road. I'll be somewhere on that route. It'll be fun to see you strutting and to see what anyone else makes of my slut Milfy! Oh, and leave the fucking dog at home!!'

As the early evening approached, there was more than a frisson of excitement from Jilly. She pulled on a tiny, black thong. Holstered her perfect breasts into a triple boost bra. Shimmied into a stretch, fake-leather mini skirt that skimmed the bottom of here ass and pulled on a thin, tight, pale, powder blue t shirt. She admired herself, marvelling at her silhouette. She had to confess she was very lucky to possess such a body. Lastly, she stepped into platform (hooker) sandals with a 'fuck me' ankle strap. She walked downstairs and her dog knew that she was dressed for a walk and lazily harrumphed himself to his feet, standing patiently, waiting for his collar to be clipped to her lead but she walked past, lost in lustful thoughts.

She looked at her watch. It was time.

She opened the door and stepped out into the cool evening air. She thought about getting a jacket but thought she looked a little more 'hooker-like' without so decided to put up with being slightly chilled (she smiled as she thought of how warmed up she'd soon get.)

She clomped down the stone steps, onto the gravel and carefully picked her way across until she reached the path. Turning left, she walked up the road for a few yards and then crossed so that she was now walking parallel to the perimeter of the park, up a fairly challenging incline.

After another forty or fifty yards, she reached the gate and went inside. Some dog walkers were around but not many and the ones who were there (thankfully, none she recognised) looked at her disdainfully, almost tutting at her overt outfit. Dusk had arrived and no one, not even Jilly, wanted to be in the park after dark. But she knew her walk through the park would be swift, four minutes at the most.

The path to the giant pond descended quite quickly and she knew that in her heels she'd struggle to walk so she went a little further into the park and found steps.

She clomped down the three sets of five or six wide, stone steps until she reached the basin of the park. The pond was in front of her, it's ornate, iron railings standing proud.

She caught movement to her left and saw a black man she didn't recognise, sitting on a bench. As their eyes met, he leaned forward and she was reminded of a hyena, sniffing the air as it searches for a fresh kill. He was clearly a body builder of the large, muscle variety. Bald and stocky but powerful looking. He stood up and without embarrassment started to follow her.

Jilly became aware of the shortness of her skirt and the height of her heels. The message her whole clothing ensemble sent out was, "I'm up for sex. I'm down to fuck. Approach me if you've got what it takes.'

She looked around and saw another man on the other side of the pond, sitting on a bench, watching. He was too far away to gauge his age. Her eyes were not sharp enough to make out features but she knew he wasn't Daniel. Though he was sitting and was in fashionable, baggy clothes, she could see that he was a man-mountain.

But Jilly was on a mission and had had clear instructions from her BBC lover. She reached the side of the pond, aware that the large black man was behind her. She walked (strutted) around the perimeter of the large pond, determined to follow her lover's instructions.

When she was a quarter of the way around, she glanced back and was aware that her first pursuer had stopped at the point at which she'd reached the pond and was watching her.

Halfway round, she was passing the second man who looked at her with a stare that gave nothing away. It wasn't friendly but it wasn't hatred or lust. It was...dead. Like an assassin.

She continued around.

At three quarters of the way round, she could see that she was about to come upon her body-building, black admirer again. He was still staring, but now he was openly rubbing his crotch through his baggy sweatpants.

Jilly was becoming quite alarmed and couldn't help but feel more than a little annoyed at the absence of Daniel.

She walked past the cock-rubbing brute, her head held high and proud and he turned, staring at her all the way.

"Nice legs. Hot, fucking bitch!" He said, quietly, as she walked past.

She chose to ignore him rather than engage in conversation of any sort.

Two to three hundred yards diagonally to her right, was the exit to the park and the sanctuary of a reasonably busy road. She stared intently and, with more than a little relief, she saw Daniel coming through the gate.

'About time'! she said to herself.

She looked across to where her other admirer had been but he was no longer sitting on his bench, in fact he'd disappeared.

She guessed that within a few seconds she'd be an equal distance from Daniel and her brute of a follower but no one in their right mind would attack her with such an obvious witness approaching. For the first time this evening, she relaxed, already thinking ahead to being pounded by Daniel and his ever-present hardness.

The path wasn't straight and, in her spiky heels, she decided not to deviate across the grass (a shorter route) for fear of sinking into the grass. The bend in the track took her in a giant arc, past some dense-looking foliage.

What came next happened with lightning speed.

Jilly was focused fully on getting to Daniel who was approaching from the corner entrance of the park. Suddenly, and seemingly from nowhere, she felt strong arms wrapped around her - one hand roughly clamped over her mouth to stop her screaming - dragging her into the bushes in less than a second where a clearing appeared to have been formed, invisible from anywhere within the park unless one knew it was there. A thin mattress filled the ground and she was firmly placed onto it, face-down. The hand remained over her mouth, her attacker's weight on her back, his crotch already pressing into her ass to stop her struggling. She started to buck and attempted a scream but the large hand over her mouth spread out, pinching her nose, cutting off her air supply. Panicked and scared; the feeling of not being able to breath terrifying her, she had enough presence of mind to realise that this was a tactic this brute had used before. She immediately stopped trying to struggle and within a second his fingers left her nostrils and she was able to breathe again. Her hands, which had been free, were pulled back and held firm behind her back in a strong, unrelenting and painful grip.

Silfy69
Silfy69
218 Followers