Before I give you the rest of the AN…If you are under 18 or legal age in your country, stop read this story and leave right now. This story may contain materials/fetish that makes you uncomfortable. If you are still reading, I am not responsible for your actions because you have been warned and you have acknowledging that you are at legal age and it's your responsibility by choosing to read this story.

I present you one of the latest story, Naruto and The MILFs! A series of one-shot smut fic.

What if Naruto go around and sleep with MILF? What if Naruto is married to a certain MILF? What if Naruto's a little homewrecker? What if Naruto and a MILF have affair? So many What if questions…That story might answer your questions. FYI, each chapter is one-shot so they have no connection to each other until I say so.

If you don't like the concept of this story or anything else in this story, please leave. No one is forcing you to read it and you chose to read it by your own will. You have been warned so don't yell/scream/whatever and just close the tab/hit back button.

All characters in this story are 18 and above.

Most characters might be OOC and there might be some grammar errors but I'm trying my best.

I'm starting this story off with a certain MILF that have never been paired up with Naruto and I'm pretty surprised that no one have goes there yet…Or did someone and I missed that? Oh well.

Here's the first chapter of NM

Disclaimer: I don't own everything mentioned in this story.


Gertrude 'Trudy' Parker-Proud


Trudy was very furious because she have a lousy day, first her lousy no-good husband don't help her with the twins and keep complaining about his works and then there were several annoying and horrible owners yelling at her for hours while she was giving their pets checkup. 'For 'caring' owners, they sure love to stressing their pets out.' Trudy fumed, sometime she hate being veterinarian.

"Here you go." A bottle placed in front of her and she glance up from the corner of her eyes to see her new co-worker that have start today, a blonde man in his twenties with blue eyes and whisker birthmarks and he was wearing the veterinarian uniform with white coat.

"Thank, Naruto." Trudy took a sip of the bottle, "What is it?"

"Latte." Naruto replied, "Sorry if it's not to your liking."

"It's fine." She waved it off as she take another sip, "I enjoy it." She glance up to him, "So...What do you think of your first day as veterinarian so far?"

"Hectic." He sat down with a heavy sigh, "I never thought I want to punch these rude guys in face until today." That earn an agreeing snort from her, "You alright?" She blinked, "You took the whole blunt of it."

"Ah, I'm alright." Trudy waved it off, "It's something that you'll get used to in time. Thank for asking." They hear a ringing bell at the front and she was about to get up until Naruto stop her.

"I get this one." Naruto got up as he head out, "I'll call you if I need help, enjoy your break."

"Thank again." She called out before she drink her latte. It's funny that she feel less stressed now.


Penny Proud enter the veterinary and she look around the waiting room until someone appear behind the counter. "Hi, how can I help you?" Naruto greeted her.

"Hi, is my mom here?" Penny asked.

"Um…" He scratched his head puzzlingly.

"Trudy." She answered his unasked question and the blonde realize it right away.

"Oh, you must be Penny." Naruto snapped his fingers as the said teenager gave him a nod, "She's out at the moment." He checked his watch, "Will be back in about ten minutes or so." His head lift up to her, "Oh, my name is…"

"Naruto Namikaze-Uzumaki." Penny chuckled, "My mom talk about you at home."

"Good things, I hope." He chuckled with her, "You're stopping by or…?"

"Kinda, I need her help with homeworks." She replied.

"On what, if you don't mind me asking." Naruto asked.

"Science and bit of math." Penny shrugged her shoulders.

"Ah." He hummed, "I can help you out with it if you want to."

"Sure." She took his offering right away as she take some papers out and some time went by until Trudy walk in to see her daughter listening to her co-worker explaining a math formula clearly.

"Now you move this number over here and what do you get?" Naruto said.

"Hold on…" Penny wrote the answer down with a thoughtful hum, "Is that the right answer?"

"Yeah, you got it." He grinned at her and he notice Trudy as Penny checked the back of textbook to make sure she get it right, which it was. "Oh hey, Trudy, you're back. Your daughter's here by the way."

"I can see that." Trudy chuckled, "Hi, Penny, are you stopping by to ask for help with your homework again?"

"Hey mom, and yeah." The teenager nodded her head, "Naruto's helping me out with some math questions."

"Do you want to take over?" Naruto asked the mother, "I don't mind helping her out more if she need it."

"Can he, please?" Penny looked to her mother, "The way he teach me is so easy and clear to understand, unlike some teachers at school and someone else." She scoffed mentally at the last part.

"You can still help her with it." The mother smiled before she shot him a look, "But not too much that you end up doing her homework for her, I want my baby to be capable of solving problems herself."

"Mooom, I'm not a baby!" The teenager groaned embarrassingly and the adults just chuckled.


Trudy wants to cry but she held it back inside to be strong, the reason why she's in this stage is because of her lousy no-good husband. Oscar. They were supposed to celebrating their anniversary but Oscar forget all about it and when she told him that, he just brush it off, claiming that he was too busy with his company…And he just forget that today is her birthday! What make it worst is that he was trying to cheat on her with some women on these important days! While he didn't do it, he was actually considering about it until she caught him and he tried to turn it around to save his own skin. She take several deep breath to recompose herself.

"Trudy, there you are." The said woman turned around to see Naruto step into her office with a wide grin before he hand a small gift over to her, "Happy birthday."

"Y-You get me a present?" Trudy blinked down at the gift in her hands before she slowly unwrap it, revealing a skincare set and cosmetic set. They appear to be affordable luxury and it's one of several popular brands. "Oh, Naruto."

"Like them?" Naruto rubbed the back of his head with a sheepish grin, "It's kinda tough for me to chose a gift that is not too much or too cheap."

"I like them very much, it's so thoughtful." She replied as she tried to not let her voice shake.

"Great." He grinned widely before he snap his fingers, "Oh, I just remember something. How was your anniversary? The wedding anniversary that you said you have been looking forward to…" Trudy suddenly bawl her eyes out, causing the startled blonde to wave his arms. "H-Hey. Trudy, what's the matter?"

"O-Oh, N-N-Naruto, I-I am so sorry…" Trudy covered her face with sobs as her co-worker rubbed her back gently to calm her down and she don't know why she end up telling him about her problem with her husband and everything, even venting out on him. It took a while until she calm down with some sniffle and she feel somewhat embarrassed that she just broke down in front of Naruto as he keep trying his best to comfort her. "I-I-I'm so sorry that you have to hear me b-babbling on and on about m-my problems and…"

"It's fine." Naruto waved it off, "Are you feeling better now?" She nodded meekly, "Good, um…Honestly, I don't know what to say that can help you or make you feel more better about the whole thing with your husband. I mean…"

"It's okay, I understand." She reached out to his hand, squeezing it lightly.

"…Hey, will it be ok if we go out to eat at your favorite place?" He suggested to her after few minutes, "Just to celebrate your birthday and to make up for the whole thing. I want to do something to cheer you up and…"

"Yeah, let's go." Trudy smiled at him.

"You sure?" Naruto asked as she nodded her head, "Alright, I'll pay for everything since it's your birthday." He looked down then up to her with a light blush, "Um, and can I have my hand back? Not that I'm complaining about your soft ha…Eh, I mean…Never mind the last part."

"Huh?" She looked down to see that she was holding his hand before she quickly release him with blushing cheeks, "Oh, sorry about that!" They looked away from each other in embarrassment before he clear his throat with a cough.

"Shall we go now?" He said.

"Y-Yes." Trudy replied and they head out for a friendly dinner.


Trudy sip her latte as she walk into the veterinary and she nearly choke on her drink with a stumble at the sight. She cough out with widened eyes, "W-Why are Bebe and Cece here?" She stared at the giggling twin in Naruto's arms as he bounced them with baby bags near him.

"Your husband just walks in thirty minutes ago and drop them into my hands then left, something about important business." Naruto frowned, "He don't even ask if you were here." Bebe pat his cheek and the blonde make a funny face to make him laugh with his twin sister.

"He what?!" Trudy hissed lowly in anger, "Don't he know I'm busy today?! I can't be off for two more hours!" She yank her phone out to call her husband but all she get is no answer, "Ooh, that…" She growled, wait until she see Oscar at home.

"You know, I'll be off in few." He shifted his weight carefully, "I can look after them until your shift end. I don't mind."

"You sure?" She was surprised by his kind offer.

"Yup, I am." Naruto replied with a nod, "It'll be two hours and I get no plan today so…" He shrugged his shoulders, "I can hang out here for a bit or take them to park across the street if you're fine with that."

"Oh, thank you very much." Trudy can trust him with her babies, "And yes, you may take them to park." He gave her one more nod before he pick the bags up then walk out with the twin, "I owe you one."

"No problem, anything for you." He hollered back and the mother of twin smiled at that before she go back to work, mentally plotting a murder of her lousy husband.


"That must be our rooms." Naruto said to Trudy as they walked up to two doors in a hotel's hallway, they were out in other town for a veterinarian conference meeting and it'll last for one week.

"Yeah, it is." Trudy nodded before she give him his room key card, "Here."

"Thank." He took it before they enter their rooms, which happen to be adjacent rooms.

"Look nice." She commented to herself as she put her luggage away after looking around the hotel room and the mother of three walk up to the adjacent door, knocking few times. The blonde open the door a minute later, "You done with putting things away?"

"Yeah, what's up?" Naruto tilted his head at her, wondering what she want.

"How do you feel about room service?" Trudy asked.

"Like getting foods delivered to our rooms?" He blinked before he crossed his arms with a hum, "I'm cool with it." He raised his eyebrow at her, "Why do you ask? You think of ordering in?"

"Yup, I need some company and you know that I don't like to eat alone." She shrugged.

"Right." Naruto chuckled, "I'll be glad to eating with you." He cupped his chin with a deep thought, "Hmm, think they serve ramen here?" That earn an amused eyeroll from her since she know that he's crazy for his favorite food, "Do we go up to the receptionist or call it from here? I've never order a room service before."

"Oh, we can call it from here." Trudy gestured to the hotel phone, "They usually come with the list for numbers."

"Ooh, I see." He make an 'ah' sound and it was quiet for a minute until he speak up, "Anything else other than dinner plan?"

"Well…" She glanced sideway at him for a moment and before she think, Trudy surprise Naruto by steal a kiss on lips then she take a step back away from him with a soft gasp as she realize what she just did. "Oh, um…I should go unpa…" Trudy attempted to make an excuse until he grabbed her hand and they look into each other's eyes. Naruto lean his head in toward her slowly to give her some time to react and she don't do anything, allow him to kiss her lips. She kiss back as his arms wrap around her in a hug and she melt into it.

"Tru…" Naruto uttered as he break their kiss apart before she pull him back in by placed her hands on the back of his head and their kiss slowly become a makeout. Trudy backpedal to bed while dragging him, still making out until her legs bump into the bedside and her hand move down to rubbing his groin. "Trudy, if we're doing it, are you sure?" He asked throughout their kisses, his left hand cop a feeling on her buttock.

"Yes, I want that." Trudy whispered into his ear, "I wanna fuck you. I want you to take me here and now."

"Alright, if you change your mind, just say the word." He kissed her nape with butterfly kisses as his right hand crawl up across her torso.

"Not trying to stop me?" She enjoyed his touch with a giggle.

"I'll be crazy to." Naruto unbuttoned her top with one hand as his another hand continue to kneading her rear, "You're one sexy MILF."

"Oh, thank you." Trudy grinned up to him as her shirt part away to expose her bra-cladded bust and she can feel his erected member behind the pant. 'Mm, big than Oscar.' She licked her lip as she slowly unzip his pant and they remove each other's clothes one piece at a time while they keep making out until there was nothing but their birthday suits. "Wow, that is bigger than I thought." She whispered to him, her hand wrap around her lover's member with a slow stroke. "Wonder how it taste?"

"You'll find out after I taste you first." He lift her up then toss her on bed, drawing an exciting squeal out of her and he get down on his knees next to bed as he lift her legs up onto his shoulders before his head dive in between her legs. He give her lower lips few kisses before he insert his tongue inside, exploring her inner tunnel with vigor.

"O-Oh, f-fuck, t-that's s-so good!" Trudy moaned out in pleasure with biting lip, her hands scrunched the blankets up under her as her lover eat her out and her hip wiggling slightly to increase her pleasure meter up. She don't know how long he have been eating her out but it feel so amazing because no one have pleasuring her orally this well before she reach her orgasm. "O-Ooh…" She panted as her lover get up, "W-Wow…"

"Now your turn." Naruto placed himself next to his lover's head on his knees on bed, his throbbing member hover near her ace and Trudy roll onto her side. She put her arm around his buttocks to pull him in close, swallowing his member eagerly in process and her tongue start to work around the shaft as her head bob back and forth at her pace. He can't help but to enjoy the sight of her lips stretching outward when she bring her head back with suctioning cheeks and his right hand caress across her side from bust to her wet maidenhood before two of his fingers slip inside, fingering her at same pace. After few minutes, he put his left hand on the back of her head as his hip thrust slightly and Trudy enjoy every moment of her lover fucking her face. "I-I-I-I'm gonna cum." He grunted out and his lover tap his thigh gently in rapid fashion before he pull his cock out of her.

"C-Cum in trash can." She breathed out and he obey her as he empty his load out inside the plastic trash bag. "I-I don't mind if you come in my mouth or jizz all over me but that can come later after our first time. I don't think you want to taste your cum in my mouth while we fool around."

"That's right." He eyed her nude body from top to bottom, "…So…" He knead her bust with thumb teasing her nipple, "Which way do you like us to do it?"

"Missionary." Trudy answered, "I wanna look into your eyes while we fuck, make out while we're at it…" Her smirking lover move around up to her lower body before he lift her hip up slightly as his member line up against her maidenhood, the tip rub the lips. "Oh, and do it fast and hard."

"Here I go." Naruto slowly push his member inside her to give her some time to change her mind and she don't as their groins met. He pull few inches out of her before he thrust it back in and his hip sway back and forth as he speed up bit by bit to furious speed. His right hand move up to caress and fondle her breasts and other hand hold her gyrating hip up by her rear, groping it in process as her legs locked around his bucking waist.

"I-I-If you're g-g-going cum, i-i-it's okay t-to c-c-come i-in me." She moaned out as her lover have his way with her to her delight, "I-I-I-I'm on p-p-pill."

"G-G-Gotcha." He grunted before his lover pulls his head down to meet her lip and they make out once again while he continues to hump her furiously, their hands caress and fondle each other's bodies to their enjoyment. Naruto's right hand slip under Trudy's head and he pull her up as they switch the position from missionary to lotus, causing the moaning black woman to bounce up and down on his thrusting member. Their makeout become more messy and sloppy as their tongues twisting around between their mouths and the lovers don't know that there are some mixed love fluids leaking on blanket under their joined hips.

"S-S-Smack m-my ass." Trudy demanded before she squeal out in happiness with moans as her lover slapped her right cheek, "A-Again, h-harder!" She feel her arousal farther with each hard spank while rode his thrusting hip.

"D-D-Damn, y-you g-get n-n-nice ass." Naruto kissed her few times before he turn her around on her chest as he plow her from behind, slapping her rear over and over to her perverse joy. After couple climaxes, he bend his head down to the side of her head as his hip rocking on her buttocks. "C-C-Can I f-fuck your ass?"

"Y-Y-You wanna f-f-fuck my asshole?" She moaned in surprise with widened eyes before she blush madly, "I-I-I've n-never been f-f-fucked in ass…"

"Wait, a-are you saying y-you're anal virgin?" He asked with a blink, "With this sweet ass of yours?"

"Y-Y-Yeah, I a-am." Trudy admitted shyly, despite the fact that her lover is inside her. "I-I asked O-Oscar one time and he s-say it's d-disgusting so…"

"R-Really?" Naruto hummed softly as he lightly nibble her ear, "So…Do you want to lose your anal virginity to me or…?"

"Y-Yes, I wanna." She said with mixed tone of nervous, giddily and curious.

"Let me know if you don't like it." He pulled his member out from her lower mouth then push it into her anal inch by inch at slow pace, "F-F-Fuck, t-t-that's one t-tight ass." He said as soon as he meet his lover's rear with his stomach and his hip move up and down gentle and slow. "H-How is i-it?" Naruto asked her, thrusting into her anal as he increase the speed.

"N-Nffmh, w-w-weird b-but I-I-I don't d-d-dislike it." Trudy moaned as her gripping fists scrunching the sheet up and she bite into it as soon as her lover's hip become blurry, smashing her buttocks crazily for the next few minutes.

"I-I'm gonna c-cum." Naruto informed her, "I-I-In or out?"

"…I-I-In." She's curious how it'll feel to have sticky fluids inside her ass and she'll get her answer when her lover ejaculate inside her, filling her anal up with his white fluids. He remove his member from her, flipping her over onto her back before he saddle her stomach and he jerk his member furiously until he shot his sticky fluids all over her upper body, some land on her face and most on her bust. "O-Oh, you came so much…" Trudy panted heavily, "And now I'm all dirty…"

"W-W-Which make it perfect t-time for us to take s-shower." He suddenly scoop her up in bride carry.

"O-O-Ooh, so t-that was your plan?" Trudy wrapped her arms around his neck with a smirk, "Jizz all over me so we can have a shower sex?"

"Yup." Naruto said proudly as he carried her to the bathroom for some more funtime in bathtub.


"I'm leaving Oscar in few days." Trudy spoke up as she snuggle up to Naruto on bed with blanket partly cover their bodies, their affair have been going on for six months and she don't regret every moment of it because she feel so happy to be with him.

"Oh?" He rubbed her back in circular motion, "Have you talk to Penny about it?"

"Yeah, I told her that I'm leaving him and taking the custody." She said, "She said she's fine with my decision, she said that Oscar have become an stranger to her instead of being her father. I think she see you in role of her father figure because you always help her with her homeworks, giving her advice when she need it and visit her at any events like her games while Oscar never done any of these." It was truth because Penny often visit the workplace even when her mother was off work, "Of course I don't tell her about us."

"That's good." Naruto hummed. He don't ask about the twins because they are too young to know what was going on but Penny is old enough to understand. "Six more months until we make our relationship public."

"Yeah, and I can't wait for it." Trudy kissed him with a happy grin, "Six more months until I'm off pill and you can knock me up all you want."

"Me too, I can't wait to put some baby in you." He kissed her back with a grin and his lover giggle when she feel his member hardened on her stomach.

"Wanna practice?" She smirked.

"Never thought you'll ask." Naruto rolled over on her and they make love right away.

Within a year, Trudy married Naruto and she feel so much happy with him. She was so relieved that Naruto tried his best and make sure that his stepchildren get equal attention and love after she give birth to their three children few years later.


And that end the first chapter of NM! Love it? Hate it?

Trudy have an unhappy marriage with Oscar until Naruto come into her life and seduce her into an affair. Naruto kinda wrecked home but it was for the best since he treat Trudy's children well…Expect for Oscar who lost everything in end. Oh well!

Who will be next MILF? What situation will it be? Will it be single or harem? Let's find out in next chapter!

Anyway, I think that's all I can say for now. Thank you for your time to read it.

Please leave reviews and feedback here. The flames will be tossed out in trash.