📚 dilf and the pool Part 2 of 2
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FETISH STORIES

Dilf And The Pool Pt 02

Dilf And The Pool Pt 02

by periquito1
19 min read
4.15 (6200 views)
adultfiction

Ashley stretches in the comfy hotel bed.

She turns around and sees Will, completely naked and sleeping, with a full mast, on May's bed.

That perfect cock is probably full of May's dried juices, she can't recall them cleaning up after he pumped her full of cum.

She can just hope May is on the pill or something, there's always a chance and she's not that old.

Ashley can't stop staring, it's such a huge, beautiful penis, and he wants to plunge it inside her.

She is slightly sore between her legs from all the masturbation, but she still touches herself under the sheets at the sight of his strong chest, slowly moving up and down, his abs covered in a bit of grey fuzz, his cock pointing at the ceiling, and her memories of him roughly using the blonde, married woman right in front of her.

He even stared at Ashley more than once while doggying May, panting hard, sweating and slapping her ass while bucking his hips.

The moans, the warmth and smell of the room...

May also looked extra sexy, bouncing on that monster cock, or being pushed down while mating.

Ashley has always known she's bi, and Jack has also known since the first date, accepting her for who she is with a smile.

Ashley holds moans, and when she feels the orgasm coming, May yawns and gets up.

Ashley has to pretend being asleep, while Will wakes up from the movement.

Like a bloodhound smelling its prey, he walks towards Ashley's bed with a smile.

She is too ashamed of what she was doing moments before, and keeps pretending while he straddles her, sitting on her belly and pulling her shirt up, admiring her tender breasts.

As he gently grabs her mounds, he gets his face closer to hers.

Even his morning breath smells good, her wet pussy pulsates under him.

He gives her a quick kiss on the lips and, to Ashley's surprise, he leaves for the bathroom, joining May.

Flustered, she thinks about the games he's playing.

At one moment he's sweet and caring, minutes later straight up abusive.

Maybe he knows when and how much to push her buttons to make her horny, then hold her tight to make her feel safe.

When they leave to have breakfast, she goes to the bathroom, showering, denying herself the orgasm and focusing on Jack, who is to arrive today with the rest of the team.

Breakfast goes by silently, with Will giving the girls bold looks, until the other two guys arrive and it turns into a talk about the day.

Most of the team will arrive at 12, apart from a couple of stragglers, and there are group activities prepared by two monitors from the resort.

Several taxis arrive to the entrance, and Ashley runs up to Jack and jumps into his arms.

"I've missed you."

"Me too!" Ash buries her head in his shoulder.

They kiss passionately, despite everyone staring at them.

Then Will comes by.

The guys hug.

"I hope she didn't give you too much of a problem!" Jack pinches Ashley's cheek playfully.

"Of course not, I've taken care of your girl for you." Will smiles at her, who is blushing nervously.

They have an hour to get settled, and she refuses to leave Jack's side, accompanying him to the bathroom, even.

The higher-ups reunion with a big client doesn't start until 6, so they have a couple of activities planned.

First, there's a big zip-line crossing a beautiful lake near the hotel.

Jack is scared of heights, so he stays down, watching the others laugh and scream.

That earns some teasing comments from their coworkers.

After that, there's a nice lunch at the hotel's restaurant where, luckily, Ashley manages to escape Will's clutches, and catches up with Jack for the days she has been gone.

That reminds her of his comments and reactions at the "boy's group", but she has done worse so she doesn't put up an attitude and enjoys her time with her hubby.

She can see Will is extremely close to Laura, exchanging laughs and having occasional physical contact.

Then, before the reunion, they have a murder mystery activity.

Ashley is chosen to be Will's (the sheriff) helper, and they have to catch the criminal.

At some point of the gymkhana they have a one on one reunion to figure out who is the perpetrator without them listening.

"I think it's a trick and there are two of them." Will confidently says.

"How do you know that?"

"All clues point to Stacey, right?"

"Yeah..."

"And haven't you seen at the glances she and Jack give each other? Mark, the private investigator (who happens to be Laura's fling), saw them talking, and Jack's accountant papers show her name a lot."

Ashley has missed all of those cues, but she goes along with his charismatic leadership.

Turns out, he was wrong.

In game roleplay, Stacey had planned the murder with the victim's partner, to stay together.

Thankfully, the parents of the deceased caught the light of it and led Mark to the right direction, who managed to trap them into a confession.

The activity was extremely well done, but Ashley couldn't help but be upset Jack was getting close to that whore who fucked her boss.

Hypocritical? Sure, but she has always been passionate and a bit possessive of her man, which Jack loved about her, unless she went too far, which she hasn't... yet.

The reunion with the clients is going alright, Ashley doesn't have much of a responsibility, but Frank, one of the co-owners, keeps sweet-talking her.

He seems kind, but isn't her type and keeps pushing it.

His big belly moves every time he laughs at his own jokes, and he is trying touching her thigh when Will arrives, chats him up with his charm and Ashley takes the opportunity to leave.

When she arrives, Jack and Stacey are chatting, with their feet in the pool.

She looks great, sure, she doesn't have Ashley's curves, but her sweet face and cheerful personality seem to be making Jack very happy.

They have their backs turned on her, and Ashley catches him taking a peek at Stacey's butt when she reaches for the pool to wet her upper body.

She storms off to her room.

May is changing, Ashley catches her fully naked.

"Sorry!"

"Don't worry, dear. What's wrong? You don't look so good."

May surrounds Ashley's shoulders with her arm, her engorged breasts pressing her arm.

"Nothing..." Ashley thinks it's ridiculous to complain about your boyfriend flirting when she is doing much worse.

"Doesn't look like nothing. It's Jack, isn't he?"

"How do you know?"

"Honey, we've all seen him flirting with that girl..."

Ashley feels like crying, and she embraces May's naked body.

"Oh, Ash. I don't want to leave you alone, but there's something I need to do. Do you want to come with me?"

Ashley's other options were staying alone in their room or going back to his husband and that tramp.

May knocks at a nearby door.

"What are we doing here?" Ashley asks nervously.

Frank, the fat guy from the reunion opens up, and smiles as he sees Ashley.

"Well, well, well! We have a plus one!"

"Poor girl is having marital issues..." May gestures with her hand to make light of it. "Ashley, my assistant. Frank, our best client."

"Will invited me last minute, but we do not say no to Will." his smile widens.

May chuckles. Ashley thinks she's a very good actress, since she can't act compliant herself.

Or maybe she does want to be here.

They go in, and Frank closes the door.

"Well, I'm freshly of the shower and ready."

He stands there, as if waiting for something.

Ashley looks at May, confused.

"Don't worry, honey. I wouldn't make you do anything you didn't want." May goes on her knees and starts taking his trousers off.

"It's a shame, though... I love your tats, and those firm tits..." Frank checks the brunette up lasciviously.

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May slaps him in the balls.

Frank gasps but doesn't move, he even seems to enjoy it.

Ashley starts walking to the door, when May says: "Oh, so your hubby can check the junior up right in front of you, but you can't stay and watch?" May looks at Frank while taking his underwear off. "You should have seen her, touching herself all sweaty and gasping while Will pushed me down and..."

"May!" Ashley startles the couple, who stop what they're doing and stare at her.

Regrettably, the assistant checks May's hand, which is circling the girthiest, circumcised cock she has ever seen.

It's short, both of her hands could envelop the whole base, but she would need them to surround the whole shaft.

"Not bad, is it?" May catches her staring and starts slowly jerking it off.

"You don't need to do anything you're not comfortable with." Frank tries to calm her down, and sits down on the bed, making himself comfortable as the married milf started kissing the pink tip.

Ashley is frozen in place, watching her boss jerking yet another impressive cock.

"Sit down, Ashley." May says, this time more authoritarian.

"I thought you regret cheating on your husband" she would like to say, but she doesn't.

On the contrary, she sits on the chair and looks away at first.

Soon, sounds of sucking and gagging reach her ears, and random gasps for air.

She turns around and May is holding his hips, forcing herself to take all of that big penis in her mouth up to his pubes.

"Fuck, I always forget how good you are, mistress." Frank grabs the sheets.

Mistress? Well, at least he's not abusive, Ashley thinks.

The fat guy looks at Ashley: "I'd love you to join."

She shakes her head, blushing.

May takes it out and, after breathing a couple times, says: "She has already eaten Will's ass, so I don't know why she's acting prude."

They both laugh at the subordinate.

She felt angry and ashamed.

"If you want to..." Frank lifts his leg up.

"NO!" Ashley finally gathers the courage to leave, not before taking a last look at May sucking that thick dick.

She slams the door and goes back to her room, crying.

Jack has been chilling with his coworkers, Stacey has been especially warm.

He couldn't take his mind off that video of Will slamming it inside her cunt.

How tight is it?

He shakes his head sternly and checks for his wife, leaving Stacey hanging.

He arrives at her door, and right then she comes towards him, eyes wet.

She's surprised at him being there, but dismisses him and tries to get in her room.

"Hey! What's wrong??"

"None of your business..."

"If it's not my business, whose is it?"

Ashley slams her second door, and Jack stands in front of it, dumbfounded.

He arrives in his room, shared with Mark.

He isn't there, but there are a couple of XL condoms spilled on his bed.

Jack sits on the toilet and takes his phone out.

He is about to talk to Ashley, when he sees lots of messages from the group chat.

Despite not being exactly in the mood, curiosity takes a hold of him.

It's both of the most active users, Mark and Will.

Jack can't believe it.

There's a picture, taken from above, of Laura's big, brown eyes staring at the camera.

She's sucking on what Jack believes, is Will's hard cock like a lollipop, while jerking Mark with a hand and making a V pose with the other.

Everyone starts going crazy. They are fucking the office's second best milf, while on a work trip, with everyone around.

Jack's penis quickly stands to attention.

He doesn't hesitate much, he's been pleasuring himself for a couple of weeks with those contributions, since Ashley is not in the mood.

"We won't give you anything else, unless you all beg for it." Mark texts alongside a smiling devil emoji.

People start begging: "Please, dude." "Come on, man, don't give us blue balls."

Will calls Jack out: "Someone's not saying anything, and you're missing something great."

The others start berating Jack, who reacted to the pic with a :O and can't excuse being offline.

He gives up and writes: "Please, guys. I'm hard as a rock."

"Pic or didn't happen *laughing emoji*."

Jack is not going to send a pic, since everyone who's sent stuff seem to be bigger than him.

They joke it off fast, and a video is sent.

Laura is on the bed, ass up, slobbering on Will's balls, moaning with every thrust of Mark's dick.

"Say hi to your coworkers, whore." Will says as he spits on her face.

She backs off and says: "Don't send that to anyone!"

Will grabs her hair forcefully and fucks her face deep, making her gag and struggle, as Mark laughs and fucks her harder, slapping her ass with vigor.

Her moans of pleasure surpass her complaints.

The video ends before she can breathe again.

People are asking for more, but Jack has already shot his load in some toilet paper.

Ashley is curled up in her bed, trying to take a nap.

She's unable to, and reaches for her phone to talk to her husband.

The screenshot she sees changes her mind.

"Please, guys. I'm hard as a rock." Really???

"Fuck it!" she yells and goes back to Frank's room.

She knocks, and May quickly answers, as if she was expecting her.

"I knew you wouldn't disappoint me."

Ashley comes in, and a joyful Frank quickly stands up from the bed.

"Ashley!"

She throws him down on the bed again, his "nice guy" attitude making it easy to take charge.

She takes his drooly, flaccid cock directly in her mouth.

"It's still girthier than Jack's" she thinks as she swallows all that meat.

Her jaw starts hurting as blood comes back to his manhood.

May sits on what used to be Ashley's chair and starts massaging her privates.

"You're awesome, Ashley." Frank caresses her hair as he did May.

"Do you like the indirect kiss, darling?" May laughs.

"It tastes good..." she answers before licking his hairy balls.

His automatic reaction is accidentally yanking the hair he had in his hand, which she secretly loves, but he keeps apologizing.

She slurps on his head, as he screams "I'm close!", but May holds Ashley back.

"Tsk, tsk... He is not allowed to cum yet. See, he is not Will. Actually, he is the complete opposite, aren't you, Frankie?"

"Y-yes..."

May lifts her eyebrow at him.

He quickly corrects himself: "Yes, mistress! Please, allow this unworthy pig to cum!"

She laughs: "Isn't it good to be in control from time to time?"

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"Sure." Ashley is warming up to this, as much as she has come to enjoy male domination, maybe she can vent her frustrations with poor ol' Frankie.

May takes Ashley's dress off, undresses herself and they both settle on the king sized bed.

"It's your turn to pleasure us, piggie."

"Yes, mistress..."

He chooses Ashley for starters.

He carefully takes her panties off and licks her cunt with fervor.

Jack is great at cunnilingus, but this guy's tongue is as thick as his cock, and it presses in all the right spots, enveloping her folds with his slimy saliva.

Ashley groans and massages her scalp as her cunt gets eaten by the guy who had just been given a presentation by her bosses.

May gets closer to her.

"May?"

"Shhh."

Her boss starts caressing and rubbing Ashley's tits, eventually licking her hardened nipples.

"Relax, love. Enjoy the attention." May kisses her cheek and then sucks on her nipple, delicately pinching the other.

Ashley closes her eyes, and the sensation her whole body is feeling, added to the wrongness of it all, makes her cum really hard, as Frank sucks on her clit and drinks her juices.

She spasm for a bit, and Frank kisses her inner thighs with devotion: "Thank you for allowing me this, mistress. Thank you..."

"It's my turn now, Frankie poo." May commands, she lays her head on the pillow and opens her legs, showing her humid pussy ready to be pleased.

"It's perfect, so pretty..." Frank admits.

"I didn't ask for your opinion! I touched your cock with my mouth, and now you're eating my pussy until I get bored of you, got it?"

"Yes, mistress!"

He nods and starts munching under her triangular carpet.

May looks at Ashley with a smile: "Are you enjoying yourself?"

"Yes, May."

"Then why don't you reciprocate?" the blonde squeezes her own supple breasts. "I haven't had a complaint yet."

May moans and pushes his face deeper into her cunt.

Ashley slowly reaches to her tits.

They are gorgeous, she admits, and definitely natural.

She caresses around, finally touching her big, caramel nipples.

"You're so good..." May quivers.

Those words lift her ego, and she takes a tit in her mouth, sucking on it with slow, circular motions of her tongue.

"Kiss me, Ashley!"

Blushing, she reaches her lips.

May holds her head and kisses her deep and thoroughly, as she cums.

May's first orgasm arrives with a cry, muffled by Ashley's lips.

They are both still ready to go.

"I have an idea. Man-thing, on your back!"

Frank quickly obeys, his fat schlong up in the air.

May straddles him, and grabs that dick to play with her entrance.

"Beg."

"Please, please, fuck me, mistress!"

His pathetic cries somehow make Ashley wetter.

She sits on his face on her own accord.

"You're learning!" May smiles.

Immediately, Frank starts licking her muff.

"Good slave, you earned your reward."

May slowly sits on his fat rod, accommodating with patience and whimpers.

She starts rocking her hips back and forth, up and down, with expertise.

Ashley is sweating, being pleasured while watching May bounce on dick is bringing her to her second orgasm fast.

She leans on his chest.

"Pinch them, babe!" May says while almost passing out.

Ashley does so, and his yells of pain and pleasure reverberate on her folds.

"Suck my clit!" she twists them.

Frank nurses on her love button until she cums on his face.

She falls backwards, with his wet face between her thighs, watching May climax on his dick.

He seems to be cumming too, since he makes the most pathetic orgasm noises between Ashley's legs.

May lays on him, wasted, and Frank takes the opportunity to suck on her tit.

When she recovers, she stops him and kicks him out of the bed.

"I want that contract signed by tomorrow."

"Yes, mistress." Frank quietly says.

The girls embrace, resting from that crazy experience.

Ashley isn't thinking about anything else than her pleasure, big cocks and her hot boss milf.

They end up napping until dinner time. They shower and change in their room, holding arms when they arrive to the restaurant.

Will waves cheerfully, Jack doesn't look as happy.

Stacey is trying to cheer him up, which Ashley doesn't find so infuriating anymore.

"Hi, Jack." she sits between him and May.

"Where were you? You missed the three-legged race."

"It's okay, you had Stacey."

"Yes, we won!" the junior adds on Jack's other side.

Ashley scoffs.

"Are you mad about that?" Jack whispers.

"Not anymore, May helped me with that."

"Stacey is friendly with everyone."

"Really? Because, apart from Will, I haven't seen her that close with anyone but you."

Jack, clueless about her being aware of the fling, realises she might be right.

"Sorry, I'll keep my distance."

"Thanks, honey." she kisses him on the lips, wondering if she ended up brushing her teeth.

That night May and Ashley have a long talk about their sexualities, needs and situations in the business.

Next morning, they all have fun as a team.

Ashley feels her love for Jack flowing back, and even holds on to Stacey's bimbo attitude.

After lunch, they have sex for the first time in weeks, and it's pretty good.

She imagines Frank when he eats her out, and Will when he fucks her.

She finds out she's slowly becoming less guilty about everything.

Maybe that's what May means with "letting herself go" and "finding out who she is".

The flight back was fun, she got to fly with Jack and Liam, another coworker. Jack took a nap and they kept talking about art.

She found out Liam paints as a side job.

They all take a rest on Monday, and Tuesday feels like everyone has come closer.

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