This story is fiction, it did not happen. I only post stories on this site. Do not repost my story anywhere else without my permission.Thank you to Cade for helping edit this story and dialogue suggestions.
MILF: JLHJennifer Love Hewitt was bored. On a Saturday night, that was unusual for her. She usually was busy doing stuff with her husband or watching over her kids. But not in New York. When she was out here, it was all business related to her upcoming movie. All the news had come out that she was having a 'comeback'. She found that to be funny, since she had not left TV over the years. Nevertheless, in her mid-40s, she was loving the attention she was receiving again. Strolling down the streets in her black pumps and a red dress that hugged her curves. The signature display of her cleavage was on point.
Out and about, Jennifer decided to slip into a club where she didn't expect anyone to recognize her. She was past her prime, as they liked to say. Not a current star in Manhattan to be seen out and about.
Her eyes fell upon a young man at the bar, probably in his mid-twenties. Tall, skinny, short black hair and a clean face. She felt that familiar itch that she had not felt in a long time. The itch for something... forbidden. Something she clearly should not be doing at all. She had never cheated on her husband, but tonight was different. She was feeling adventurous. She strutted her way to the bar with the kind of confidence that could only come from years of being in the spotlight in years past. She took a seat beside him, and with a seductive smile, she leaned in close, her breasts brushing against his arm. He looked up, surprised but definitely not displeased. She ordered a whiskey, neat, and offered to buy him one as well. She knew she had him hooked when he looked down at her chest and his eyes lingered on the deep pit between her tits.
"Hi, what's your name?"
"I'm Alex, and you?"
"Jennifer."
He looked at her cleavage again and smiled, "Sorry, you've distracted me a little bit." She laughed at him. "Don't worry. I have that effect, I know."
The whiskey arrived. Jennifer didn't realize he had ordered a drink before she sat down. She raised a finger at the bartender, demanding a round for herself. "I see you like a good drink yourself," Alex said. Jennifer nodded, "only in the company of someone handsome like you."
When her order arrived, Jennifer took a sip. Alex had already downed his shot fast. She placed her hand gently on his thigh and began to stroke it. He stiffened for a second before relaxing into her touch. She could feel his eyes on her, once again distracted by her cleavage. "What brings a young man like you to a place like this?" she asked, playing with the ice in her glass.
Alex replied, "Just here with some friends.." He looked over his shoulder as if to confirm their whereabouts. "But I don't mind a little company from a woman."
"Well then, that tells me you don't have a girlfriend," Jennifer purred back.
"Not tonight," he replied with a smirk, his eyes locked on hers, the challenge accepted. "What about you? Shouldn't you have a husband or something?"
Jennifer took another sip of her whiskey. Alex was bold with his question, so she felt it was best to reward his honesty. "Oh, I do," she said, her voice low and seductive. "But he's back home, none the wiser."
Alex's eyes widened. "Really?"
Jennifer nodded, her fingers still dancing on his thigh, just to give him a little touch. "But tonight, I'm just a woman looking for a bit of... entertainment." She leaned in closer, whispering into his ear, "And I think you could be just the ticket."
"Ticket to where exactly?"
Alex was interested. Jennifer was surprised he didn't seem nervous. Maybe he had experience with older women like her. She took his hand and placed it on her upper thigh, moving it upward until it was dangerously close to slipping up her dress. He didn't say anything back, so Jennifer smiled.
"How about a private show?" she suggested, her voice a soft purr. He swallowed hard, his Adam's apple bobbing in his throat. She could feel the heat from his palm across her skin.
"What kind of private show?" He asked.
Jennifer leaned closer, her breath hot against his ear. "The kind where you get to see all of me," she whispered, her hand sliding down to cover his, letting him feel her warm touch. "And I get to see all of you."
Alex chuckled, "that's not what I was thinking. Usually, a private show around here involves some kind of dancing."
Jennifer's smile grew wider, "Oh, I can do that," she said, her hand sliding up his thigh. "But it won't be a dance floor performance." She leaned in closer, her breasts pressing against his arm, "It would be something more intimate." Alex bought in to her offer.
"You have my attention. So long as you are grinding on my lap like you do your husband," he caught her off guard, blushing. Jennifer had not given a lap dance in years. Not since before she had her kids. Alex was making her feel young again at the thought of grinding her ass down on his lap.
An hour later, they were back at his apartment.
Alex walked her in and they shared a brief kiss. Jennifer returned the kiss and guided his hands to touch her curves. Walking her around his place, he offered her a drink at the kitchen but she wasn't interested. Alex's apartment was a little messy with stacks of boxes and clothes everywhere.
"Come on, we can do the private show in here," he led her to his study room with a big leather chair, couch and a book shelf. Jennifer nodded, looking around the room. "I'm going to need some music," she told Alex.
"No problem," he walked over to a stereo and pressed a few buttons. The speakers boomed loud, modern rap music that she had never heard before. The auto-tune and generic beats were so out of place, making Jennifer really feel her age. He could see she was too old for his kind of music, but he didn't care. Alex took off his shoes and slipped off his shirt, making himself comfortable in his chair. "I'll wait for you if you need a moment."
Jennifer took off her shoes and placed them neatly beside his. She turned to face him and began to sway her hips to the beat. She didn't know the lyrics but she knew the dance moves, easily moving in sync to the rhythm. It was the kind of music that you felt in your body, not just heard with your ears. She had not given a lap dance in so many years, or even to music like this. Turning her back to him, Jennifer revealed her plump ass. She reached behind her back and unzipped her dress. The fabric fell to the floor, revealing a black thong underneath and matching bra. She stepped out of the dress and began to dance.
Her movements were slow and deliberate, hips gyrating as she moved closer to him. Alex's heart raced as he took in her voluptuous figure. Jennifer had once been much slimmer. She had to wonder if he thought she had a MILF body now that she was a bit on the thicker side. She was like a fine wine, aged to perfection at 46 years old. Alex sat there in the chair, nodding his head, impressed with her tease of a dance thus far.
Finally, she made her way to him, her legs straddling his thighs. She leaned over him, placing her hands on the chair's armrests, giving him the full view of her huge, natural breasts in the black lace bra. The room was dimly lit by a single lamp, casting a radiant, yellow glow across her skin. She began to sway her hips in a slow, sensual rhythm. Alex's hands gripped the leather chair tightly, his eyes never leaving hers as she moved closer. Her ass shoved down in his lap, grinding steadily. Alex was impressed.
Jennifer reached behind her and unclasped her bra, letting it fall to the floor. Her tits bounced in the open, the perfect handful. She leaned back, pressing her chest into his face, her nipples grazing across his cheeks. Alex took this as an invitation and opened his mouth, taking one of her stiff nipples into his mouth, sucking on it. She moaned softly, rising up and then bouncing her ass down on his lap. She could feel his cock growing harder as it rubbed between her thighs. He squeezed her tits, sucking on one nipple then switching to another one. Jennifer lowered her hand to her thong, brushing inside to play with her pussy as she became wetter and wetter.
Alex buried his face between her tits, motorboating them loudly. Jennifer became more excited, still grinding on his lap a bit more to finish the lap dance. She pulled away, getting up from his lap and walking over to turn the stereo off. "I think that's enough now. You've got me excited," her eyes fell to the poking erecting in the front of his pants, "and I can see you're excited too."
Alex nodded, standing up from the chair, his cock straining against his jeans. Jennifer felt she was in a position to make demands now. As she pushed her thong down, she spoke low, "take off your pants."
Alex wasted no time, eagerly unbuttoning his fly and pulling down his jeans. He was looking at her wet pussy, seeing that it was fully shaved. His boxers followed suit, revealing an erection that was as long and thick as she had hoped. Jennifer was impressed at the length. She licked her lips, watching him step out of his clothes. "Now, sit back down," she instructed, pointing at the chair.
He listened to her, his eyes never leaving hers as he sat down, his cock standing tall and proud until his hand wrapped around it. She walked back over to him, her bare breasts jiggling around with each step and her heels loudly stomping into the floor below. Jennifer fell to her knees and grabbed his dick, smiling wide, "now it's time for some real fun." She twisted her fingers and jerked them up and down. It was time for Jennifer to see if he had truly been with another older woman before her. She would be able to tell based on how he reacted to the way she sucked his dick. Opening her mouth wide, she slipped his cock between her lips.
Jennifer began to suck hard. She had not sucked cock in a long time, not even her from her husband. The sound of her slurps filled the room as she took him in deep, feeling his length hit the back of her throat. Alex groaned, throwing his head back at her deepthroating wonders. "Fuck.." he moaned as she continued to suck. Jennifer squeezed his balls with one hand, teasing him further as she went on slobbering and sucking his dick with hunger.
Looking up at him, Jennifer gave him a look that told him she was not playing around. She was hungry, full of lust to be unleashed on this younger man. Alex knew he was in for the time of his life with a woman like her. He reached down and began to stroke her brown hair, pushing her face closer to his crotch. She took him even deeper, her cheeks hollowing out as she tried to take more of him. Her fingers unhooked from the base, giving her more room to bob her head up and down, sucking all of his cock.
"Fuck," Alex groaned, "just keep sucking it," he said while looking into her eyes.
Jennifer was thrilled at him telling her to keep going. She had missed this, the feeling of power she had over men with her mouth. She sucked harder, bobbing her head up and down. So far Alex didn't seem like he was close to blowing his load. She liked that from a young man. It was telling to her that he had experience with older women like her. But now she was testing him to his limits with another deepthroat push. All of his cock was in her mouth, the head reaching the back of her throat. Alex moaned, but he didn't grunt. She pulled her mouth away from his cock with a pop and let it slap against her cheek.
"That was a pretty good blowjob."
Jennifer smiled, "you think so?"
Alex nodded as she rubbed her tits. "You haven't seen anything yet," Jennifer replied.
He nodded a second time and smirked, "I know what you're about to do. Go ahead, wrap those titties around my cock."
She was impressed. Jennifer held up her big tits and just smiled, "how did you know that's what I was about to do?"
"No point in denying it, babe. You've got an awesome rack. You don't just sit down at a bar and talk to a guy like me without thinking ahead. I know what's on your mind. You were hoping I would be able to last long enough for you to titfuck me. So go ahead. Don't waste any time. Wrap those big tits around my dick and put 'em to work."
Jennifer was surprised but also quite turned on by his directness. She thought she was in control, but Alex proved otherwise with how confident he was in commanding her. Her huge breasts engulfed around his cock as she squeezed them together. Moaning at the feeling, she began to pump them. Alex moaned as she tittyfucked his cock with ease.
Alex leaned back in his chair, watching his cock disappear between her breasts and then reappear again. "Fuck yes," he moaned, "that's what I've been waiting for tonight."
Biting her lower lip, Jennifer purred. She looked down and watched his cock poke up a few times, then glared back at him. "I hope you can handle this."
"I think I'm handling it just fine about now, huh?" She laughed at him, "yeah, sure. Right now you are, but it won't be for long."
"Oh yeah? Does your husband last more than a minute between your tits?" Alex was taunting her with the question and the smug smile on his face. Jennifer picked up the pace, her breasts bouncing up and down with every stroke. She felt so powerful knowing that her tits could work a man into a big explosion of cum at any moment. Jennifer didn't respond to his words. Alex kicked her into overdrive as she thrust her tits up and down much faster, tittyfucking his cock even harder and faster.
Alex felt the pressure building, the sensation of her warm, soft flesh squeezing his cock was heavenly. He could feel the beginnings of his orgasm approaching, his balls tightening up. He didn't want to think about it. Jennifer got an upper hand on him, working him so close to blowing his load with the power of her cleavage. "Fuck! Yes!" he yelled, "keep it up! I'm gonna cum soon!"
Her eyes met his and she smiled. She knew what was coming and she loved it. Jennifer thought about the last time her skin had been decorated in cum. She felt his cock pulse in the grasp of her breasts, and she knew it was time to demand what she wanted. "Pull out," she instructed.
Alex nodded, his hand moving to his cock as he pulled it out from her cleavage. "Where do you want it?" he panted.
Jennifer held her breasts together, raising her head proudly. "All over them," she demanded. "I want to feel your hot cum all over my tits."
Alex nodded eagerly, stroking his cock as he watched her. She had a certain power in that moment, a cougar demanding satisfaction from her young male prey. He couldn't resist the feeling of disappointment that she made him pull out to do this. It would've been so much more satisfying for her to keep fucking him with her tits until he exploded. Her eyes were hungry and her expression was so seductive. He couldn't resist her, forgetting the disappointed feelings. With a deep breath, he took aim, pointing his cock at her rack and started stroking hard.
Jennifer felt the warm, sticky liquid spurt onto her breasts. The first shot landed directly onto her neck, making her smile. The subsequent ropes of cum painted her chest, covering her in a white, creamy mess. She loved the feeling of it on her skin, the slight sting of the hot liquid smearing onto her breasts. Alex groaned, his eyes rolling back in his head as he emptied himself onto her. The final drops fell between her tits, mixing with the lines layered across her tits.
"That's it," she said, her voice filled with satisfaction. "Give me every last drop." Jennifer wrapped one arm around her boobs and then used her right hand to grab his hand. She pulled his own grip away from his cock and replaced it with her own. Alex moaned as she moved his dick towards her right nipple and squeezed it hard, milking out the final drops. She rubbed it against her nipple, smearing his cum and then smiled as she let go. "That's all of it. I got all your load on my tits."
Alex's breathing was heavy, his chest rising and falling as he sat there, his cock now limp, hanging low. "Fuck, that was amazing," he managed to say.
Jennifer giggled, standing up and letting her breasts fall back into place as they glistened in cum. The streams of semen now dripping down her chest. "I'm glad you enjoyed that," she said. "But don't think this is over. I need you to get hard again so you can fuck me."
She reached for his cock, grabbing it and stroking hard. Jennifer resumed control as she guided Alex around, pulling at his cock to make him walk with her. He moved behind her, looking at her plump ass. Jennifer's heels were loud on the floor. She noticed a big black, wooden shelf on the left wall. Below it contained rows of DVDs and other stuff on the shelves. It would serve fine for a place to be fucked. She let go of his cock and placed her hands on the shelf, arching herself out and glancing behind one shoulder. Legs spread, she offered herself right there.
"Fuck me."
Alex took a moment to admire her from standing directly behind that nice ass. His cock was still sensitive from the intense orgasm but it was starting to twitch back to life, mostly thanks to the touch of her hand. He stepped up to her, placing his hands on her hips and pushed himself against her. She felt his cock poking at her wet pussy. "I want you to fuck me hard," she said seductively. "I need to feel you deep inside me. Fuck me until I cum on your big, young cock."
Alex grabbed her hips, using them to hold on as he slid his cock into her pussy. Jennifer moved her head and moaned. She shoved herself back to take in more of his dick. Since her boobs were covered in his cum, Alex didn't want to get his hands sticky in his own seed. He wrapped one arm around her waist and used the other to grip her left ass cheek. He bucked his hips, pounding into her pussy. Jennifer moaned, closing her eyes as she felt her titties shaking up and down.
"Harder," she begged, pushing back against him. He complied, slamming into her faster. The sound of their bodies slapping together filled the room.
Alex's hand tightened on her hip, his grip firm as he thrust into her. He gave her what she wanted, thrusting harder and faster. Jennifer's eyes opened wide as she gasped. Alex was fucking her the way she wanted. Her thicker body made it easier for a young, wild man like him to pound into her at a steady pace. Jennifer moaned, screaming for him. "YES, YES, YESSSS!! OHHHHH, YESSSSSSSS!! FUCK ME! FUCK ME, HARD!! THAT'S IT!!"
Her cries only made him try thrusting harder and faster. Jennifer squealed and screamed more. "YESSSSSS!! OHHHH GOD, YES!! YESSSSSSSSS!! FUCK ME!! FUCK ME, ALEX!! KEEP FUCKING ME!!" She was drawing closer and closer to her orgasm. Jennifer lowered her right hand and played with her clit, rubbing at it to push herself even closer to a release she so desperately needed. Only Alex could deliver her to the height of pleasure. For all she knew, he was likely close to his second orgasm already. Jennifer slipped up. Her mind was jumbled thinking about that. She would cheat on her husband but she didn't want this young man cumming inside her.
"I'M ALMOST THERE, FUCK!! PULL OUT!!"
His hand slapped across her ass. Jennifer glanced behind her shoulder, snarling at him. Alex gripped her hair. He was still pounding her pussy with his hard cock.
"Pull out," she repeated, more urgently this time. He tightened the grip in her hair, but slowed down his thrusts "I want you to cum on my tits again."
Alex shook his head, "not yet. I want to make you cum first. That way, you can clean my dick with your mouth. I want to watch you lick it. After that, I'll blow another load on your tits."
Jennifer moaned, raising her hand from her clit. She showed him her fingers and licked the middle one, pushing it into her mouth and plucking it out. "Okay," she lowered her hand, "but you have to pull out when I tell you to."
Alex grinned and nodded. He let go of her hair. Jennifer turned her head, facing the wall again as he started thrusting again. It only took a few seconds for him to find that fast pace again of hard thrusts deep in her cunt. Jennifer was close and he knew it. She cried out, screaming and then he slapped her ass, "let it go! Cum for me!"
Her pussy tightened around his dick. The walls clenched and unclenched as she released a powerful orgasm "PULL OUT! RIGHT NOW!!" Alex got the message and quickly pulled out, watching her juices squirt all over the floor in a small puddle.
Despite the hard orgasm, Jennifer was unbothered. She was a MILF now and quickly recovered, falling to her knees and grabbing his cock. Alex watched as she shoved it into her mouth and began slurping her own juices off it. She slobbered and slurped loudly, slowly sucking his cock. Her hands held up her breasts that were still coated in his cum from earlier. After she was done sucking his cock, Jennifer pulled her lips off with a pop. She raised her tits and wrapped them around his dick. Looking down at it, she spit on the head. Alex saw the chance now that he was going to get to fuck her tits. He didn't waste any time as he began pumping between them.
The feeling was just as amazing as before, but now he had control. He watched his cock disappear and reappear in the valley between her breasts. "You like that?" he asked, panting heavily.
"Mhmm," she moaned, nodding her head. She leaned back, the shelf brushing against her back. The pleasure was intense, the way he fucked her tits made her want more. "Don't stop," she breathed. Alex kept going, "I'm not pulling out this time. I'm going to fuck your tits until I cum. You're getting a pearl necklace this time."
Her eyes widened at the thought, but she didn't protest. If she didn't want it, she would've unwrapped her tits right then and there. Instead, she leaned her head back and moaned. Jennifer smiled, thinking about how she would be making this man cum twice. Alex watched his cock slide through her breasts, feeling the softness of her skin and the tightness of her grip. She was so wet from her orgasm that her juices had started to trickle down her legs, near the puddle. The smell of sex was thick in the air, making him even more eager to fuck her tits and release another load.
He picked up his pace, fucking her tits harder and faster. His hips slapped against her chest, the sound echoing through the room. His thrusts were so hard that Alex's cock nearly touched her chin. "You're going to get it all over me," she teased. Alex just nodded as he kept going. His cock went back and forth, fucking her tits faster. "I'm not pulling out this time. It's going all over your neck and tits."
Her breath grew shorter and her eyes fluttered closed. The feeling was overwhelming, his cock sliding over her skin, the friction building up. She could feel his orgasm approaching, the way his cock grew thicker and harder, ready to pulse. "Do it. Cum all over me. Give me that pearl necklace."
With a guttural groan, Alex let go. His cock exploded, sending rope after rope of cum shooting out. It landed on her neck, her chin, and her chest. She felt the hot spurts of cum on her skin, mixing with the other bigger load from earlier. It was a messy, beautiful sight. He kept going, pumping her tits until his cock was drained of all its seed. Some of it was stuck between her tits, making it easier for him to give a few more thrusts When he was finished, he stepped back, out of breath.
Alex looked at the result of their hard fucking. Her tits and neck were covered in cum. She had a small drop on her chin. Jennifer smiled wide.
"More cum than your husband?" Alex grinned. Jennifer didn't say anything back. She used her middle finger to scoop the cum off her chin and then shoved it into her mouth. She sucked the tip clean, flipping him off. She was a MILF now. Young men like Alex were the kind she could have her way with.
"I'll take that as a yes," he said. She laughed and decided to humor him, "fuck yes. You're far better than he is."
Alex sighed, moving to the chair. He was worn out after two rounds with her. If he could've handled a third, she would've considered sticking around. Jennifer stood up and grabbed her thong and bra off the floor. She had to get dressed and be on her way. Now that she was a MILF, she could give young bucks like him more than they could handle. His exhaustion was proof of that. Tonight made a wonderful memory. Jennifer felt she had truly entered MILFhood as a woman.
The End.
Topic: MILF: Jennifer Love Hewitt (Read 2352 times)