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Actors & Actresses / Beach Day Gone Right (Jennifer Love Hewitt)

« Last post by MineCraft040521 on February 02, 2026, 03:49:36 PM »

Beach Day Gone Right
Starring: Jennifer Love Hewitt
Tags: M/F, Cons, Oral, Titfuck, Facial
DISCLAIMER: This story did not happen and is complete fiction. Not all facts will be 100% true to real life.

A day at the beach was exactly what Jennifer Love Hewitt needed. Though she loved her husband and three children, every mother needed some alone time on occasion, and that’s exactly what Jennifer was enjoying at the moment.

Lying on a beach towel, the curvy, 46-year-old MILF was wearing a black bikini that showed off her mature curves, along with her mouth-wateringly large breasts. Jennifer knew that people were gawking at her, though she took it as a compliment rather than an insult, especially as she was nearly 50 years old and had birthed three children.

As Jennifer was lying on her towel, enjoying the feeling of the hot sun on her body, she felt something hit her foot. It didn’t hit her very hard, and as she sat up and lowered her sunglasses, she noticed that it had just been a Frisbee.

“Sorry about that, ma’am,” a young man said, hurrying over to grab his frisbee from where it sat on the sand.

Looking up at him, Jennifer took in the sight of the tall, attractive man approaching her. Judging by his face, he couldn’t have been older than twenty-one. As the man made his way over to her, Jennifer saw something bouncing around in his swim trunks, which made her jaw nearly drop at the size of the guy’s package.

“That’s quite all right,” Jennifer told him, grabbing the frisbee and handing it to him, not hiding the fact that she was ogling his young, muscular body, “what’s your name, handsome?”

“It’s Michael, but my friends call me Mike,” he told the older woman, smirking as he watched her look him up and down, while he did the same to her.

“Jennifer,” she started to say, letting her eyes wander down to the slight tent in his bathing suit, which he didn’t seem to worry about covering up, “Now, was that frisbee hitting me an accident or were you trying to get my attention?”

“I swear I wasn’t trying to hit you,” Mike told her honestly, “but I can’t say I wasn’t occasionally glancing over here at you.”

Jennifer’s lips curled into a grin at Mike’s honesty, along with the fact that he willingly admitted to checking her out. Though she shouldn’t have been too surprised, since he’d been very openly checking her out ever since he walked up to her.

“Oh, really? All of these fit, young hotties around us, and you’re checking out an old lady like me?” Jennifer asked, putting a hand to her chest in a show of flattery.

“You blow all of these girls out of the water, ma’am, and by quite a long shot,” Mike said, his eyes only occasionally stopping to look at hers as they moved up and down her curvy, MILF frame.

“That’s very kind of you, sweetie. Say, are you here with anyone?” Jennifer asked him, sitting up, which made her large breasts jiggle, which Mike made sure to watch.

“Just a couple of friends, but I don’t think they’d mind if I left them for a bit,” Mike told her, his lips forming a grin that matched Jennifer’s.

“Good, cause I was thinking maybe you and I could find somewhere private to…talk some more,” Jennifer said, though her tone made it clear they wouldn’t be doing much talking.

“I know a spot, there’s a couple of private showers not too far from here that most people don’t know about. They’re a lot more spacious than most of the other ones,” Mike explained, lending Jennifer a hand as she stood up.

“That’s good, cause I’d actually like to get some of this sand off me before we…talk,” Jennifer told him as he watched her breasts jiggle while she stood up.

Mike led the way across the beach with Jennifer next to him, both of them checking the other out along the way. The young man took note of the older woman’s wedding ring, though it seemed like she didn’t particularly care about cheating on her husband, so he wasn’t about to bring it up. Especially since he was so close to banging the hot MILF.

“Here we are,” Mike announced as they arrived at the row of private showers, each with large, wooden doors that blocked all outside eyes from seeing inside.

Opening one of them, Jennifer was able to see that Mike was telling the truth, and these showers were much bigger than normal. It also looked a lot cleaner, since it likely wasn’t used nearly as much as the others.

As Jennifer stepped inside, she turned the shower handle and stepped out of the way of the cold water. Mike followed her into the shower and stood behind her as he closed the door, checking out her thick ass, which seemed to swallow a majority of her bikini bottoms.

Looking over her shoulder, Jennifer smirked as she saw Mike checking out her ass, which she wiggled at him, making his cock jut in his swim trunks.

“Do you happen to have a thing for older women, Mike?” Jennifer asked him, turning around to face him and smirking as his eyes slid down to admire her big tits.

“I thought that was pretty obvious,” he told her, as his eyes slowly moved back up to look into hers.

“Just checking,” she replied, reaching behind her to untie the knot on her bikini top.

Once she’d gotten the knot undone, Jennifer grabbed the cups of her bikini top to prevent them from falling and revealing her tits. She wanted to tease Mike just a bit before she let him ravage her body.

“You’ve been looking at my tits quite a lot today. I bet you’d really like to see them, wouldn’t you?” She asked him, smirking as she played with her tits, all while not revealing them to the nearly drooling young man yet.

“Fuck yeah, when I was with my friends, I couldn’t stop looking over at those incredible tits of yours,” Mike admitted, feeling his cock grow harder inside his bathing suit as Jennifer continued to tease him.

“And what did you imagine doing with my tits while you were looking at them?” She inquired, starting to lower the cups of her bikini top before pulling them back up again.

“Well, I thought about doing a lot of things. I imagined squeezing them, kissing them, sucking on them, but mainly, I imagined sticking my cock between them and fucking them,” Mike told her, growing even harder as he imagined Jennifer wrapped her huge tits around his dick.

“Oooh, I like that last one a lot. Squeezing these big tits around that big cock of yours. Sliding them up and down your dick until you can’t stand it any longer, and cover me with a hot load. Mmmm, that just sounds so good,” Jennifer moaned, continuing to play with her tits before she finally stopped teasing and let go of her top.

Mike’s dick nearly ripped a hole in his trunks as he watched Jen’s massive breasts jiggle against her chest, her pink nipples just begging to be sucked on.

“Fuck me,” Mike said as he admired Jennifer’s heavy tits, which had little sag to them despite her age and the fact that she’d birthed three kids.

“Not until I get a taste of you,” Jennifer quipped back, smirking as she sauntered over to the young man, placing a hand on his hard cock and squeezing it through his swimsuit.

“Go right ahead, cause I’m definitely not stopping you,” Mike told Jennifer, who smirked at the younger man as she slid down to her knees.

The surface she was kneeling on wasn’t the most comfortable, but Jen knew that as soon as she had Mike’s rock-hard, girthy prick in her mouth, she wouldn’t be worried about that. Sliding her fingers into the waistband of his trunks, Jennifer hastily slid them down his muscular legs, allowing his hard dick to flop out.

“Whoa, now that is one big cock,” Jennifer said with a laugh, taking Mike’s prick in her hand and beginning to slowly stroke it.

“My big dick matches your big tits perfectly,” Mike told his older lover, who smiled up at him as she continued the handjob she was giving him.

“Just wait till it’s between them,” Jennifer said with a grin, taking her hand off of Mike’s member so she could spit in it before returning it to his dong.

“Oh yeah, that’s much better,” Mike moaned, feeling his dick twitch between Jennifer’s thin fingers as she jerked him off at a slightly faster pace now.

“Then you’re really gonna enjoy this,” Jennifer told him as she leaned in and swallowed the first few inches of his girthy shaft.

“Fuuckkkk,” Mike groaned as he watched the busty MILF on her knees before him start to suck his cock.

As Jennifer bobbed her head on Mike’s dick, she made sure to keep direct eye contact with him. Her eyes stayed locked on his, even once he’d shut his due to the pleasure coursing through his whole body. Jennifer grinned with her lips around his prick as she slid another few inches into her throat, doing her best to handle the enormous beast traveling down her gullet.

Mike was greatly enjoying Jennifer’s blowjob, but much quicker than he’d expected, he had to stop focusing on how good it was and focus on not losing his load too quickly. He didn’t want Jennifer to think he couldn’t handle her oral skills (even if they were exceptional), so with his eyes shut, he tried to think of anything that could possibly keep him from busting down her throat in just a few minutes.

Jennifer could tell by the look on Mike’s face that he was trying not to cum yet. She loved knowing that young boys, no matter how hard they tried, were just no match for her MILF experience. She didn't mind that this occasionally meant a throat full of cum earlier than expected. Having a young guy bust down her throat was something Jennifer loved, so a slightly premature ejaculation wasn’t the worst thing in the world.

But Mike’s plan seemed to be working. As he focused as much of his brain as he could on non-sexual thoughts, he was able to keep his orgasm at bay. That is, until Jennifer slid his cock from between her lips and replaced it with her hand as she spoke to him.

“You’re not trying to keep me from getting fed, are you? Cause I would really love to have a thick load of cum pumped down my throat right about now,” she told him as she took her hand off his shaft and went back to expertly blowing him.

GLACK GLACK GLACK sounds filled the surrounding area as Jennifer practically choked herself on Mike’s young dick. The twenty-something guy ran his hands through his hair as his overworked brain processed what Jennifer had said, along with the feeling of her juicy, MILF lips sliding up and down his pole.

“Shit, if you keep this up, you’re definitely gonna get fed soon,” he told her, making direct eye contact with her as he looked down to see her slide the last remaining inches of his prick into her throat.

Shooting a wink at the boy, Jennifer licked as much of his shaft as she could with it lodged in her throat, as she brought up a hand to play with Mike’s smooth balls. The several incredible-feeling sensations were just about all Mike could handle, and as he grunted out a warning, his spasming prick began to fill Jennifer’s throat with her protein drink of choice.

“UGHHHHHH,” Mike loudly groaned, tossing his head back as he blew his load straight into Jennifer’s stomach, the horny MILF moaning as she felt her boytoy for the afternoon explode.

Mike couldn’t help but thrust his hips as he came, making Jennifer gag several times as he forced her to swallow his load. The 46-year-old mom didn’t seem to mind one bit, especially as she continued to slurp on Mike’s prick after he’d shot the last of his load into her.

Finally pulling his dong from her throat after cleaning it, and making sure not a drop of his jizz went anywhere but into her stomach, Jennifer planted a kiss on Mike’s tip before offering him a hand to help her up. Mike gladly did so, allowing the thick MILF to get back on her feet so they could continue their public shower sex.

“I should probably take these off if we’re gonna continue further,” Jennifer said as she began to untie her bikini bottoms.

Mike made sure to watch as Jennifer removed her last article of clothing, finally revealing her perfect pussy with a neatly trimmed brown bush above it. The boy couldn’t stop himself from licking his lips at Jen’s MILF twat, especially since he knew that he would soon be deep inside of it.

“I’d love to put that tongue of yours to use, but I haven’t been fucked in a real long time,” Jennifer told him as she walked to stand right under the shower head, bending over to give her young lover a perfect view of her fat ass. “So, come and fill me up, stud.”

Mike nearly slipped and fell as he hurried over to Jennifer, placing a hand on her thick waist and gripping his cock with the other so he could aim his bulbous head at her opening. Giving a slight thrust of his hips, Mike was able to slip it inside of Jennifer’s warm and snug cunt with ease.

“Ooooooh, yeah, that’s exactly what Mama's been needing,” Jennifer cooed as Mike slowly slid his girthy prick into her MILF snatch.

Jennifer kept her hands against the wall as she thrust her ass back to meet Mike’s thrusts, not suppressing her moans one bit as she was filled with the cock of a man less than half her age. The horny MILF didn’t care that they were in public, as the feeling of his young cock sliding in and out of her cougar cunt felt too good.

“Give it to me good, baby, and I’ll let you fuck my titties and cover them in your seed,” Jennifer moaned, her large breasts bouncing as Mike fucked her from behind.

“Then, I’m gonna give you the best fuck of your life,” Mike told her, increasing the speed of his thrusts along with his grip on Jennifer’s wide hips.

As he gave it to the stacked MILF harder, Jennifer started to let out louder moans at a higher rate, while the sound of Mike’s waist smacking against her jiggling booty grew along with it.

“Gosh, you young guys are such better lays!” Jennifer exclaimed as she basked in the pleasure of being on the receiving end of Mike’s big dick.

“And you older women are so much fucking sexier!” Mike said back, eliciting a chuckle from Jen, which quickly turned into a loud moan.

Sliding his hands up her wet body, Mike began to grope at Jennifer’s large, swinging breasts, pinching her thick nipples between his fingers as he continued to fuck her. The busty brunette let him know how much she enjoyed it by pushing back harder against his thrusts, increasing the already loud sound of her ass clapping.

“Yes! Pinch my nipples, you big-dicked stud!” Jennifer cooed, tossing her head back and moaning toward the sky as she continued getting pounded from behind.

“Fuck, turn around, I wanna see your tits while I fuck you,” Mike told the sexy MILF, groping her breasts for another few seconds before retracting from her cunt and allowing her to do as he said.

Once Jennifer was facing him, he grabbed her by her wide, child-bearing hips and lifted her into the air, slamming her against the wall and shoving his cock inside her twat again. The stacked brunette’s eyes shot wide open as she felt Mike’s split her cunt in two.

“HOLY SHIT!” Jennifer shrieked as Mike resumed his fast fucking from just a minute ago, the young man’s eyes glued to the famous actress’s huge rack.

While his hips slammed against hers, Mike held onto Jen and stared at her incredible chest, loving how her tits bounced while he fucked her. The sight made his cock pulse, which made him thrust even faster and harder into Jennifer’s pussy.

“Oh my gosh, you’re fucking me so good, baby! I’m gonna cum soon!” She told him, wrapping her arms around the twenty-something man and scratching at his muscular back, nearly drawing blood, but thankfully not.

“So am I,” Mike said back, grunting as a mix of water and sweat poured down his young body, making Jennifer’s delicious body look even more appealing.

“So keep on fucking me, kid! Don’t slow down on me now!” Jennifer exclaimed, a big grin on her face as she let out a laugh while wrapping her thick thighs around Mike’s waist.

With all four of her limbs wrapped around him, Mike started to fuck Jennifer as fast and as hard as he could, which was a bit difficult, as, at the same time, he had to make sure he didn’t cum. Jen had promised him the chance to tittyfuck her, and he was certainly not going to miss out on that.

So, using all of the strength and energy he had left, Mike furiously fucked Jennifer Love Hewitt, still one of the sexiest stars in the world. Her snug cunt was gripping him tight, but that didn’t stop him from slamming his hips against hers and bottoming out inside her twat again and again.

“YES! KEEP GOING! ALMOST…THERE!” Jennifer cried out, a hand snaking up to Mike’s short, brown hair and pulling his head back so she could smash her plump lips against his.

Mike began to sloppily make out with the busty MILF while he fucked her, doing everything in his power not to lose his load before he got the chance to fuck the gorgeous cougar. Luckily for the young stud, he didn’t have to fuck Jennifer for much longer before she came, her thick body tensing up before she let out an ear-piercingly loud shriek.

“YAAASSSSSS!!” Jen loudly moaned, digging her fingers so deeply into Mike’s shoulder and scalp that she nearly tore off some of his skin.

Thankfully, Mike got through Jennifer’s orgasm unharmed, and once he was certain she’d fully finished, he slid his prick out of her slit, his tip leaking precum against her mound.

“Looks like someone’s ready for the grand finale,” Jennifer said with a giggle as Mike set the short brunette down on her feet.

“If you’d be so kind,” Mike told her, smirking as the busty cougar got down on her knees before him, licking her lips as she eyed the throbbing, veiny monster.

Without another word, and with her eyes now locked onto his, Jennifer grabbed her large, wet breasts and lifted them up, slowly wrapping the soft flesh around Mike’s prick.

“Fuck,” Mike groaned, running a hand through his short, wet hair as he felt Jennifer’s tits slide up and down his throbbing shaft.

“Yeah, that’s what I want you to do. Fuck these big tits, baby!” Jennifer exclaimed, smiling brightly at the young man as he thrust his hips rapidly.

Mike knew he wasn’t going to last long between Jennifer’s tits, no matter how badly he wished that he could last an hour fucking her incredible jugs. The large, soft orbs slid so smoothly along his prick due to their wetness, which made it a mesmerizing experience for the young man.

“Fuck, Jen…those tits. Fuck!” Mike groaned, unable to do much besides moan and enjoy the feeling of tittyfucking Jennifer Love Hewitt’s legendary rack until he inevitably blew his load.

“I know, sweetie. I know you love these big, MILF titties. Just keep on fuckin’ ‘em until you empty those balls for me again,” Jen cooed, clearly enjoying the tittyfuck as much as Mike was.

“Fuck, you want it all over your face, don’t you? All of my cum dripping from your sexy fucking MILF face?” Mike asked, biting his lip as he felt his balls churn, signaling that he wouldn’t be lasting more than another few seconds.

“Yeah, paint my fucking face, you dirty boy!” Jennifer exclaimed, and mere seconds later, Mike let out a roar as he came, ropes of thick, off-white man juice flying out from his tip and splattering the busty brunette’s face.

“ARGGHHHH!” Mike grunted, squeezing his hands into fists as he blew what must’ve been the biggest load of his life all over Jennifer Love Hewitt’s face.

As ropes of cum kept on shooting out, Jennifer giggled and opened her mouth, allowing several spurts to hit her tongue, giving her her second taste of his jizz. The older woman cooed as she swallowed some of Mike’s cum, while the rest of it landed haphazardly across her face.

“Oh my gosh, you fucking drenched me!” Jennifer said with a laugh, both of her eyes shut due to the sheer amount of semen on her.

“Fuck me, that was insane,” Mike told her, breathing heavily and sweating profusely as he watched a final bead of cum seep from his tip.

Jennifer wiped her eyes clean of cum, sucking it off her fingers until she noticed the jizz in Mike’s tip, which she quickly lapped up with a swipe of her tongue.

“Fuuuuuuck,” Mike groaned, his sensitive prick twitching as he watched Jennifer wipe a strand of cum from her cheek with her finger.

“I knew a day at the beach was exactly what I needed,” Jennifer said with a giggle, dangling some of Mike’s jizz from her finger until it fell onto her tongue.