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Daughter’s Hot Friend (MysteriousPleasure x xMandyx) NSFW

Mark grinned ear to ear when Kayleigh pulled up in her cart. “That all just depends what was on your menu Kayleigh”the pervy man grinned, eyes making their way along her body from head to toe. This wasn’t the first time Mark had encountered Kayleigh and despite his best efforts he hasn’t seemed to make any sort of lasting impression on her that he could tell. A sexy teen like her got hit on non-stop though so he partially blamed it on that. He tried the cliche business card technique, flirting, and even offering her shopping trips but Kayleigh never budged and only played along with him.

“How about…..”pausing as he reached for his wallet flipping through the bills and grabbing a $100 dollar bill out. “A beer for me….a beer for you….and my buddy is somewhere down over there and can definitely use one….” nodding in the direction of James. “And you can can keep the rest beautiful”. If Mark couldn’t convince her with his previous attempts, perhaps a little extra incentive money will put him on the right path for a bit more of Kayleigh’s time.
 
It was easy for Kayleigh to sit back and watch as men ogled her body. Older or younger they were all the same and couldn’t resist someone like her. They were only human and their male instincts were naturally attracted to a girl that was very physically attractive.

Some members at the club she came across more often than others. Most of the time faces just all ran together but some people Kayleigh made an effort to remember usually because of the tip they gave her or whatever other reason she may have had.

“Welllllll I can’t drink on the job and I’m not 21 yet sooooo if this was a test then I guess I pass”. Winking at Mark, Kayleigh hopped out of the drivers seat and stepped around her cart. “You might need the extra beer for yourself if your friend isn’t even at the green yet. It’d save me a trip down to him if only he was as good as you right?” she giggled playfully giggled, opening the cooler and grabbing a can of beer for Mark, cracking it open and handing it to him.

“Thannnkkkk youuuu”smiling wide and accepting the generous tip. Make sure to flag me down if you need anything else ok? Good luck out here!” And with that Kayleigh offered just enough flirting and got back into her cart and started driving off in the direction Mark pointed her in. There were a few trees, some bushes, and a maintenance shed but she would have to drive around to get in there. Humming to herself, Kayleigh didn’t notice anyone through all the bushes until she pulled around the shed. Without even seeing clearly who the man was, Kayleigh greeted him cheerfully, “Heyyyy. I have a special delivery, your friend thought you could use a beer and help get you to the green”
 
Just her playful nature alone got Mark excited not to mention her giggles and pretty smile. Damn what he’s give to feel her tight body up through her clothes. Those full breasts pressing firmly against that top, just begging for attention. Mark had to hand it to her that even as a teenager she knew how to use her looks and behavior to her advantage. As excited as he was to see her, it was crushing that she had to leave so soon…. If only James was up here at the green she wouldn’t have had to leave so soon.

Pondering his situation and where his ball laid, James didn’t have many options to get to the green. He could chip his ball back onto the fairway or he could risk it and try to clear the shed and hopefully land on the green if he was lucky. Positioning himself he heard the sound of a cart approaching, assuming it was Mark to check up on him until he heard her familiar voice.

James immediately entered panic mode. He’s been daydreaming about Kayleigh for so long now that he had zero idea how to approach her. His mind raced with all the thoughts of her….of them….of the cheating….of how fucking good she left him satisfied. Her outfit did nothing but send him into a daze, feeling himself getting warm inside. She didn’t even realize it was him yet but how will she respond? Taking deep breaths, James tried calming himself down before responding to the beautiful drink cart girl. “H-h-hey Kayleigh…. Long time no see” James finally managed to say. God she looked amazing as ever he thought to himself.
 
As soon as she pulled up to the man, Kayleigh had already slipped out of the driver seat and went to get him his beer, wish him luck, and then be on her way to the next thirsty golfer. Just as she grabbed the beer from the cooler and opened it, Kayleigh paused when she heard James’ voice.

It had been quiet between them since her car wouldn’t start that night. Being honest with herself, she didn’t even know how things were going to continue between her and James. He was obviously into her but his marriage was holding him back. Instead of chasing after her, telling her how much he desired her and try setting hookups for them to fool around, she didn’t hear from him. She could have teased him herself but that seemed a little too risky in case he wasn’t near his phone or anyone ask why he is even talking to her.

Acting calmly, Kayleigh turned around and approached James as she would any other male golfer out there, with a big smile and her assets on full display. “Your friend said you were probably getting thirsty all the way back here sooooo…..he bought you a beer” handing the can of beer towards James. “Sorry but I have to run, there’s a group ahead of you that really….needs my attention….”she said softly, turning and walking back to her cart without waiting for a response from James, heading over to lean in and close the cooler back up.
 
The interaction with her was so quick and James did not expect it to go that way at all. No flirting, no teasing, and no touching. Was she for real? James stood there in silence. He was in complete shock in the turn of events as it was not hat he was hoping for when he showed up to golf today. He didn’t really know what to expect but their previous encounters always end up sexual.

“W-wait! Hold on a second Kayleigh!” Juggling his beer in his hands and almost dropping it, quickly making his way over to her before she had the chance to drive off. Seeing her bent over, James wanted to enjoy the view out was in too much of a panic that what started out as something very hot has turned ice cold. Stepping up behind her, James cleared his throat slightly before placing a hand on her hip.

“So….is it just like that then? I’m guessing you’ve….moved on…. I will admit I was really looking forward to seeing you here today and I have to add you look just as incredible as ever…. You definitely fit the job very….very nicely. I guess I just need to know what I did wrong? Is this about the parking lot? I’m sorry if I was too rough but you just get me wayyyy too worked up….”
 
James was just too predictable. Chasing after her like a poor lost dog trying for her attention, not wanting her to leave him behind. It was almost a little depressing but what could she expect from an older man that had been smitten by a sexy younger girl that gave him the pleasure he had been missing out on in his marriage. Feeling him approach and get up behind her, Kayleigh quickly stood up before letting him enjoy the sight any longer.

“Umm sir? I really don’t know what you’re talking about….. employees aren’t supposed to interact with guests and although I’m glad you enjoy my appearance, harassing employees isn’t something the club really needs to be hearing about…. I might just have to report you….” Continuing to remain calm, Kayleigh struggled to remain serious and held back any giggles, only letting a small smirk escape. Showering her with compliments and apologies, Kayleigh could easily toy with him and drag this out all day long knowing she was completely on his mind.

“and you apparently don’t know the rules to golf either because that club you want to use so badly…I’m pretty sure it’s illegal….”gently leaning back against James, her hand reached around between them, sliding across his bulge.
 
A ghostly chill ram throughout James while Kayleigh seemed to be ignoring him and treating him like just another horny make at the club trying to hit on her. He could feel his skin turning very pale, stomach becoming knotted that everything appeared to be over between the two of them….until her hand reached for his bulge.

“Ahhhhhh”he immediately gasped, all the color instantly returning to his skin. Kayleigh was definitely a dangerous one for sure. There was a small thrill to being toyed at by her but it definitely wasn’t something James wanted to experience very often.

“God I’ve missed you Kay….” James murmured, lowering his lips, kissing frantically at her neck, hand reaching to turn her face to his, pressing his lips to hers. His other hand roamed all over her right body, across her stomach, up over her breasts, squeezing at each before sliding back down across her stomach, fingers sliding under the waistband to her skirt. Feeling no panties, his hand sunk deeper until his fingers found her clit, gently massaging with his middle finger.
 
Gasping out loud, now in his embrace, a playful smile spread across her face. James hadn’t missed a beat and reacted immediately to her touching him. His hands all over her tight body, lips working their way at her neck until her head was turned towards his. Playfully kissing back at him with small wet pecks quickly turned into longer, deeper kisses. Kayleigh’s tongue wrestling along his, reaching her hand back around his head, panting and kissing frantically at James.

“Oooooo mmmmm you’re….ahhhh….going….mmmm…. to get me in so much trouble…..”giggling and talking between making out with James, her body was enjoying the attention. Nipples hardened immediately while his hand slid into the front of her skirt. “Ohhhhhhhhhh”she moaned once his finger began to rub at her clit. “James…..you must have really missed me hmmm?” Spreading her legs slightly to give him better access, Kayleigh leaned back against him, continuing to kiss him long and deep.
 
With each kiss James’ body got hotter and hotter. Cheating on his wife was becoming such and obsession for him and it just wouldn’t be the same if he were to just leave Laura for Kayleigh. Kayleigh might not even want that and might be enjoying this herself, being a sexy little home wrecker all for her own amusement. Someday maybe he would actually just sit her down and discuss what the hell was even going on between them but for now, he only wanted one thing….

Groaning into her mouth for each wet kiss, James’ tongue found it’s way deep into the teens mouth, exploring while rolling along hers. Feeling her ass backing up against his erection, his finger continued rubbing and massaging her clit before sinking further down. Feeling her soft velvety folds made his cock twitch like nothing else. So smooth and beautiful, his finger slid right between them, parting her smooth lips. Bending his finger slightly he penetrated her pussy, greeted by her wetness, finger sliding and curling inside of her back and forth. Enjoying the moist fee of her pussy, his ring finger then joined as well. Pressing both fingers into Kayleigh’s womanhood, smooth and deep, curling back against her walls, pressing against her g-spot.
 
Body wiggling up against James, waves of pleasure were engulfing her. Making out with James hard, she just didn’t want to stop their heated session one bit. They both hungrily kissed at each other sharing pants and moans of hot pleasure. His fingers sliding into her pussy were met with a slight gasp, feeling him explore her, sliding his fingers as far as he could. “Ohhhh ohhh ohhhhh” Kayleigh moaned, once James found her g-spot.

“Uhhhhh don’t stop baby oooooo”. Bodily wiggling like mad from the sensation. Forcing his fingers in and out of her while being sure to run along her sensitive area made her all the more wet and horny. Gasping and trying to catch her breath, his fingers weren’t letting up and at this rate she was going to have an orgasm. “Mmmmm fuuccccckkkkk” she moaned, hand slipping between them and finding his bulge, giving him a playful squeeze before frantically undoing his shorts and let his cock out.
 
The thought didn’t even cross his mind that someone on the golf course could stumble upon them during this little rendezvous. They weren’t exactly in plain sight out in the open but there was still the risk….. James obviously ignored the risk entirely while continuing to sexually explore his admirer.

Feeling her up against him, bodily wiggling and shaking with pleasure made his fingers slide faster and faster. Thumb circling her clit, fingers curling harder and faster, giving her small spurts of rapid motions, James barely even noticed her undoing his shorts and freeing his raging erection.

“God Kay…..you’re so fucking hot…..I need you so badly baby….” Hand cupping her full breast through her shirt, his fingers didn’t let up once bit. Her juices flowing freely, finger tips pressing against her pussy walls like mad
 
Unable to focus on his pants while James’ fingered her pussy like crazy, fingers sliding in and out so quickly but sensually, Kayleigh finally managed to free his cock. Grabbing at it, she tried her hardest not to squeeze his throbbing erection too hard. “Ohhhhhh ohhhhhhhhhh” she moaned, body shuddering once more, breathing so heavily into James’ mouth. Between the thrill of his words and him fingering her so seamlessly, Kayleigh couldn’t hold back any more with James pushing her to the brink of orgasm.

With her soft hand wrapped firmly around his cock, Kayleigh squeezed at it on and off before finally giving into the pleasure and climaxing. “Mmmmm. Fuck! Ohhhhh ohhhh fuck! Uhhhhyyeahhhhh ohhhhh”. Her body tensing and spasming with pleasure, shivering up against James with glee. She honestly wasn’t expecting that from James but deep down, her flushed body was glad. All wound up and knowing she was equally as horny as James, there was only one last thing to do in order to solidify their affair.

Breaking their kiss giving him small wet kisses trying to catch her breath she tried her hardest to form a sentence. “Mmmm….ahhhh… that felt so….mmmmm so good baby. I can’t wait any….mmmm anymore….I want you to fuck me James….god I want you to fuck me so bad….”
 
With his cock fully hard and erect in her hand, James was already raring to go. Getting Kayleigh off was such a turn on. Always teasing with her body and playful talk, making her orgasm was just a small gesture of how he wanted this relationship to continue. Sliding his finger out from the front of her skirt, James took in a few deep breaths.

His hand was a bit shaky from the excitement and all he could think about was lasting as long as possible. Having sex with a girl like Kayleigh was something he never dreamed of happening. He just knew it was going to feel incredible to finally be inside of her. Hiking her skirt up a bit, his hand pressed at her lower back while the other hand slid to her waist.

Cock pressing against her smooth ass, James grabbed a hold and guided his cock to her wet lips. Heart racing with excitement, feeling his head rubbing against her pussy. Not wasting any more time he pressed up against Kayleigh, his cock penetrating her younger pussy, pressing his cock inside of her. “You…you’re so tight Kay…..holy shit…”.
 
Panting and still catching her breath, Kayleigh felt James pushing and bending her over a bit. Still riding the sexual high of her orgasm, she nibbled her lower lip while looking over her shoulder at James, feeling him pressing his cock into her. Wincing slightly once his cock began penetrating and sliding into her [NSFW], Kayleigh let out a small whimper, her pussy stretching around his hardness.

“Uhhhhhh fu-fu-fuckkkkk you’re too big James!” moaning and feeling his cock pressing further into her soaked pussy. Wrapped firmly around his cock, Kayleigh continued to gasp and moan feeling James force his entire length inside of her. Her body wanted him so badly, even if it wasn’t exactly the ideal setting, she didn’t care. James inside of her solidified everything and she knew he would be hers.
 
Desperately trying to calm himself and settle down, the sensation of filling her pussy with his cock was incredible. Pressing further and further, stretching her pussy until he was all the way inside of Kayleigh. Standing there, balls deep inside of her, James relished the amazing feeling. The affair moving onto a whole new level, his eyes looked into hers and knew immediately how bad she wanted this.

Pulling out a little, he pressed his cock back in, giving Kayleigh a few smooth short thrusts. Hips pressing against her perfect ass, her body moved along with his rhythm. More and more he pulled his length out further and further each time only to thrust all the way back into Kayleigh. Cock soaked in her juices James finally got into a rhythm with her, his hips bucking back and forth, grunting with pleasure each pump. Leaning in, he kissed at her once more, one hand sliding under her shirt and to her breast.
 
Pressing her lips to his for a long kiss, Kayleigh’s hand slid over James’ as he squeezed and massaged her breast. “Uh!….uh!….uhh!”, moaning with each pump, her body moving along with James’. Turning her head to face forward, Kayleigh began to arch her back a little, pressing her ass back against James, rocking her hips and matching his rhythm, wanting him to be deep inside of her.

“Yeahhhh yeahhhh mmmm fuck me James mmmmm yeahhh”. A wide smile spread on her face, begging James to fuck her, to take her body for his own. Hair dangling from her head, Kayleigh continued rocking her hips back into James, yelping on occasion with his cock pressing deeply inside of her. Almost forgetting that they were in the middle of the golf course while she was at work, the sound of an approaching golf cart went unnoticed, pulling around the maintenance shed and coming to a stop right in front of her drink cart.
 
Cupping her breast and pinching her nipple, James’ hips continued pumping in and out of Kayleigh. Long deep thrusts into her, the sensation providing a pleasure he’s never felt or enjoyed since he could remember. Her moans only heightened the sexual thrill he was receiving, knowing how much she was enjoying him, an older man fucking her. Everything felt amazing he didn’t even take into consideration whether Kayleigh was on the pill or not.

Grunting with each thrust, a wave of fear immediately came over James when out of the corner of his eye he noticed a cart pulling up. Balls deep inside of Kayleigh, James suddenly stopped, seeing Mark leaving the cart and stepping around, standing before the two of them.

** “Hey, you give up on me, I’m getting bored up there so what’s the prob-……. Woah!” Stopping in his tracks, Mark looked in awe seeing James up behind a bent over Kayleigh. Mark had always envisioned himself with Kayleigh while masturbating and here was James getting to live his dream for real. “When I bought you a beer I didn’t realize there was an alternative menu I could have ordered from….mmmm mmmm mmmm”eyes taking the sight all in, walking up closer, eyes on Kayleigh.
 
“Uhhhhhh uhhhhhhh yeahhh James! Give it to me ooooooo” she continued to whimper and moan while James enjoyed her from behind. His bare, married cock buried deep inside her unprotected teen pussy. All she could think about was his throbbing cock pounding in and out of her wet hole until another voice was heard with the appearance of Mark standing before the two of them.

Gasping, eyes like a deer in headlights Kayleigh looked at Mark. Her body was frozen like James, bent over with him inside of her, neither moving a single muscle. This was real bad. Not only would she lose her job but James’ life would be ruined entirely. Fooling around in secret was all about the thrill and not about pulling him from his wife and family. Thinking fast, Kayleigh knew she couldn’t let this escalate into anything horrible.

Eyes looking up at Mark, Kayleigh caught her breath and smiled. “Well not everyone deserves a peek at the special menu. When you said he was having a horrible game today and needed a beer, he seemed to need…a little….something else”. With a small grin, Kayleigh’s eyes glanced down at Mark’s crotch and then slowly back up to his eyes, mouth slightly cocked open, playfully raising an eyebrow as a subtle suggestion.
 
Frozen in fear, knowing everything was about to spiral out of control in a hurry for him, James stood there in horror, unsure how this was about to play out. Now if this was his younger days, if he had gotten walked in on while with a girl, it would just be a large amount of embarrassment. Being a married man with a daughter while fucking his daughter’s friend was something James was not ready to try and explain to someone let alone live with the guilt that someone now has blackmail on him.

“It….it…it’s not what it looks like. Well…I mean it is what it looks like but I can explain…”stumbling with his words, hands shaking from the fear from being caught with Kayleigh.

** A little puzzled hearing James’ attempt of an explanation, Mark was more captivated by Kayleigh’s choice reaction… “Pfffff please….I know exactly what’s going on here and I must say…. I can’t blame you one bit”. Stepping closer towards Kayleigh, standing in front of her. “Now don’t take offense, I know Laura is a total catch but this….is something no man could ever…ever…pass up. I just wish I knew how much he had to pay you baby..”. With a sly grin, Mark ran the back of his finger along Kayleigh’s cheek. Reaching down and undoing his pants, eyes on Kayleigh while pulling the zipper down, Mark pulled his stiffening cock from his pants, waving it before her face.
 
Instead of calling James out, blowing up on him for cheating on his wife, or showing any signs of reporting this, Mark went simply with the flow. Like any other horned up man she has come across, Mark was smitten by her and wasn’t about to pass up any opportunity, even if it did mean sharing a girl with his buddy. It seemed like James and her were going to be spared and in the clear….for now…..

Giggling playfully from his comment Kayleigh looked on while Mark undid his pants and guided his cock to her pretty face. “How about we just talk about that later hmmm?” Hand reaching for his cock, Kayleigh toyed at him briefly, running his head around her lips, feeling him tense and harden further while in her grasp. Looking up at Mark, her lips parted and took his head into her warm mouth, slowly rolling her tongue around his head. “Mmmmm”she moaned along his hardness while taking a bit more into her mouth, eyes glued to Mark. Gently rocking her hips back against James as a sign to continue, he would just have to accept the fact he would be sharing her with another man (NSFW)
 
** “ohhhhhh….yeah baby….just like that” Mark groaned aloud, not caring at all who could hear or even enjoying himself in front of James. His focus was entirely on the busty beauty in front of him and her willingness to pleasure him. His hand cupped the side of her face, looking down at Kayleigh, guiding her head along his length, loving her hand squeezing and stroking his base. Inch by inch his cock slid into her mouth. As much as he wanted to fuck that pretty face of hers, Mark stood there and let Kayleigh use her well honed skills.

Looking on, seeing Kayleigh begin tending to Mark and seeing his reaction, James was still too stunned to do anything. He’s never been involved with group sex and never imagined he would be sharing a girl with another guy. Neither had any interest in the other man and they both just wanted Kayleigh.

Feeling her ass pressing back against him brought James out of his daze. Watching her head bobbing back and forth along Mark, James resumed fucking her from behind. Pulling out a little and slamming his cock back inside Kayleigh, James got back into rhythm, pumping his cock in and out of her tight pussy. Her cute ass gently jiggling with each pump, seeing her between the two of them was such a turn on.

“What a slut….” was all that James could think of. Taking both cocks on at once without any hesitation. Mark was under the impression that James paid her off but if he only knew….. Surely though Kayleigh would never been tempted by offering her “services” for money would she? She was just a horny teen that desired an older man right? And James was the only one she wanted? Pushing aside all those thoughts, James gripped her hips and continued pressing himself inside her, his pace quickening.
 
“Mmpfff mmppfff mmmpppfffff mmmm mmm mmmpffff” Her moans muffled with Mark’s cock each time James pumped his cock into her from behind. Spit roasting between the two older men was very hot. Two holes filled at the same time, both men grunting and groaning with pleasure, all as a result of her.

Hips rocking like mad at James, feeling him deeply fill her pussy, her hand squeezing and stroking Mark, all while her head bobbed along his cock. Hand stroking faster, her mouth began moving all around, letting his cock poke into her cheek, tongue rolling and swirling around his length, tasting the precum that leaked from his head. Pausing with his head in her mouth, she stroked him hard into her mouth before resuming.

Satisfying Mark would hopefully keep him quiet but how long that would really last is something only time would tell. Kayleigh hoped this would be a one time thing but something deep down told her this wouldn’t be the last time she dealt with him. Hopefully he didn’t get the impression every girl at the country club was as willing as she was.
 
**Head leaning back, Mark let out another pleasurable moan. “God you handle cock so well Kayleigh…..who woulda known…. Errrmmm you’re going to make me cum so fucking hard you sexy little slut….mmmm”. Hand reaching and grabbing her ponytail, the way her lips and hand worked at his cock, Mark wasn’t going to last very much longer

Just like Mark, James was close to climaxing as well. Her pussy felt amazing wrapped around his bare cock which had him wondering if he should risk getting her pregnant? Does Kayleigh expect him to pull out or cum inside of her? James had no idea whether she was on the pill or not, He just knew how amazing she felt and that he was ready to cum.

“K-Kay….I’m going to cum baby….ohh…ohhh ohh….ohhhhhh fuck baby!” His conscience getting the better of him, James quickly pulled out despite how badly he wanted his seed inside of her. Cum immediately spurting from his cock in long streams across her smooth ass cheek.

**Pushed over the edge, Mark treated Kayleigh to his own load of cum, backing his hips away, cock springing from her mouth, Mark started stroking his cock, blasting her pretty face with a direct spurt of cum streaking across her eye and forehead with another glob to her cheek. Panting, he began smearing his cum across her cheek and to her lips.
 
Body rocking back and forth between their two older cocks, pleasuring them both, hearing their lustful grunts and moans, knowing she was pushing them both over the edge, Kayleigh was letting out her own muffled moans while her body was being used. Hearing James near his orgasm, Kayleigh’s pussy clenched at his cock, wanting his cum to shoot into her womb.

Feeling James quickly pull out and start cumming on her ass (NSFW), a wave of disappointment washed over her. His streams of cum coating her ass cheek, dripping down her smooth skin, she knew he was too nervous to risk getting her pregnant but having him cum in her would have been the perfect stepping stone to further this kinky relationship.

Unfortunately Mark didn’t give her much opportunity to question anything. Cock sliding from her mouth, he wasted no time cumming on her pretty face (NSFW). “Ohh!!” she gasped while his hot cum painted her face, letting him smear it everywhere, flicking her tongue along his cum coated cock. Catching her breath while both men seemed to be enjoying their handy work cumming on her, she stood back upright.

Yanking her skirt back down, James’ cum soaked into her skirt while taking a finger and trying to wipe off Mark’s cum from her face. Stepping to her cart, she grabbed the towel she used to wipe off beer cans and begin cleaning her face up.
 
Both men felt very weak in the knees after Kayleigh drained both of them. To James, each time feels even better than the last. The only thing to had made the experience better was if he didn’t pull out. James wanted Kayleigh to know how committed he was to her in this hidden relationship and that she was definitely worth any risk. Fucking her was a thrill he never could have imagined, even if he did have to share the experience with Mark in attendance.

** Trying to savor every moment with the busty brunette, Mark slid his cock into his pants and walked over to Kayleigh while she cleaned herself up a little. “I didn’t think it could be possible but you look even hotter as a cummy mess…..” giving her ass a small squeeze. Reaching into his pocket, Mark pulled out one of his business cards. “Here, in case I could ever convince you to “earn” a little extra money off the golf course, just give me a call and I’m sure for you I could definitely work something out.” Giving her ass another playful squeeze Mark stepped over to their own cart.

Eyes on Kayleigh, James wasn’t sure what protocol was. As much as he wanted to talk to her and tell her how amazing she felt, having a discussion with Mark around was a degree of awkwardness and he had hoped she would understand. They both wanted the same thing and things were only to get more heated. With a small smile, James got back into the cart to finish up. His golf game definitely didn’t improve and the only thing he could think about was being inside of her.
 
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