Dec 10th: The 100 Girlfriends Who Really, Really, Really, Really, Really Love You - Harem

Rentarō Aijō was a man with many girlfriends. Due to a number error in the heavenly processors, he’d been designated 100 true loves rather than the usual 1. He was a good man, who loved love more than anything, and he wished to make all his girlfriends happy as much as he could, slowly building his harem for the betterment of their lives.

So when he was called to the roof by one of his girlfriends, he thought nothing particularly of it. That was their hangout space after all, but he’d still go to the top of Mount Everest if one of them wanted him to. That’s how dedicated he was.

As he permeated the door to the open air, he was not expecting to be attacked and handcuffed and blindfolded.

“Woah!” Rentarō exclaimed, landing on his back in a panic. Though not as roughly as he’d expected, as his body landed on an impromptu bed atop the roof. He scrambled a little to escape his bonds, but to no avail. “W-what’s going on?! Who are you?!”

“Rentarō Aijō, how many girlfriends do you have now?”

He knew the voice of one of his beloveds instantly, “T-twenty two? Hahari-san?”

“That’s right. And while we all come in different shapes and sizes… don’t you realise that you have adults in your harem?”

She removed the blindfold, unveiling the most beautiful sight to the harem owner.

Hahari Hanazono, Mei Meido, Momoha Bonnouji, and Nadeshiko Yamato. The owner of the school, her maid, the ethics teacher and the Japanese teacher. All in very revealing lingerie and posing distinctively around the boy. They were all his beloved girlfriends that he loved very much, and he was very concerned about the hungry looks in their eyes.

“W-woah! What?!” Rentarō gasped, a blush quickly rising in his face and something else rising in his pants. “A-are we allowed to do this in Young Jump?!”

“This is an erotic fanfiction, Rentarō-san.” Mei calmly replied. The maid was as demure as ever, even in the fetish maid outfit. The black parts of her frilly costume were see through to see the supple underwearless skin underneath. “We are able to fully reveal our adult feelings to you and you may respond in kind.”

“Didn’t you realise you’re eighteen now for no reason?” Momoha laughed. The unethical ethics teacher chugging some **** as she relaxed on her side on the bed. Her outfit was a lot less specialised, but just as sexy to Rentarō. Her loose hoodie was all she wore, just draping over her naughty bits and promising the erotic bouncy body underneath. “Ethically we ain’t gonna shtoup a minor, but here we can fuck all we want!”

“We gonna ride you like an American pig on Thanksgiving!” The confusedly ‘American’ Japanese teacher concurred. Nadeshiko waving her flag happily even in her silly themed lingerie. Star pasties on her nipples, blue and white strips encircling her large breasts and crotch, and the iconic cowboy hat atop her blonde head.

“Rentarō…” Hahari said quietly while she placed her hand on his chest. Slowly undoing his shirt buttons with a serious look on her face and a see through negligee on her bosom. “You will be all of our first’s. We have waited so long to be with you, and we all wish to share many more memories with you. Please, respect our wishes?”

The boy had tried his hardest to ignore all the erotic feelings he had being around so many beautiful women every day. He’d locked that side of his personality behind many firewalls. Not until the girls all became of age, or the polygamy laws were changed, or Young Jump became a doujin manga… but right now?

“Yeah, of course. We’re in an erotic fanfic, it’d be bad to not have sex.”

The girls all gave an ecstatic beaming smile back to him. Quickly piling onto his fallen form to kiss and lick his face wherever they could find space.

“Alright! I call first dibs as I arranged all this!” Hahari declared, pushing back the other girls who gave her a frown. Though they all joined in on the unveiling of Rentarō’s cock. The slow build up was palpable, his underwear straining to contain the thick slab of meat underneath as soon as they pulled down the trousers. The tip was visible over the top of the boxers, and his nuts were almost on full display through the leg holes. To say it left little to the imagination was an understatement.

“Wow… is that cause a the hentai we’re in?” Gawped Nadeshiko.

Momoha shook her head, “Naw, I think that’s canon.” She giggled, reaching over to squeeze the covered part of the phallus. “Boy’s gotta be a giga-chad to have 22 girlfriends. Of course he has the dick to back it up.”

“I would like to ‘back it up’ onto his big dick. ‘It’ being my privates.” Mei agreed calmly. The other’s all looking at her in shock, though the woman with her eyes forever closed just stayed smiling. “Miss Hahari has instructed me to add in as much sexual dialogue as possible for the proceedings. Was that satisfactory?”

“It was fine, dear,” The milf with a maid hummed, starting to drool across herself as she quickly disrobed Rentarō of his remaining clothes. The busty mother gripped his loosened shirt and brought her thick legs over his body until the heavy erection was pointing right at her uncovered nethers. The negligee blew in the wind while the woman swallowed her nerves away, “Are you ready, Rentarō?”

Without a moment’s hesitation he replied, “No.” She blinked in worry, though he continued. “I wanna be untied. It’s unfair you can put your hands on me but I can’t explore your body too.”

Hahari smiled. A genuine touching moment for Rentarō to wish to touch her momentous body. “Very well.” She agreed, and in a flash Mei had unlocked the handcuffs. Rentarō quickly gripped onto the thighs on either side of his body. Rubbing his fingertips along her skin, feeling the slight goosebumps form as her body pulsed in pleasure. “R-Rentarō… d-don’t tease me too much…”

The boy looked directly into the eye of her pussy. Serious and determined, he lowered his head to the hole. “Thank you for bringing Hakari into this world.” He said, then reaching his fingers up and stroking along the edge of her slit. The juice was plentiful, and the touch of her beloved was enough to send Hahari into spasms as it was. Both were slightly awkward in their approach, but neither felt that way as the other encouraged them to keep pushing further. Until it was already past the point of no return.

An incredibly moist pussy practically gobbled Rentarō’s dick as soon as it pushed past the first layer. Neither had expected him to slip so far in on the first thrust, but her unbelievable wetness just gave the engorged phallus such an easy access point that it was in and blowing her mind before she could blink. Rentarō could almost see the pleasure travel up the mother as soon as he pushed it inside. Her whole body quivering all the way until it **** her eyes to shoot to the sky and her voice to travel with it.

“GGAAAIIIEEEEEEEE!!!!!!”

The other girls were very impressed. Especially when Rentarō’s hips began to uncontrollably hump into the warm snatch that had landed on him. The teenager practically drooling himself as the heat of the moment caught them both, transforming them into grunting cavemen bent on only procreation.

“Wow.” gaped Yamato. Waving her hand between the two’s locked gazes and finding it unbreakable. “They’re hornier than a Florida man in a gravy boat!”

Mei smiled, “My mistress is being split open by the extra sausage that Rentarō has delivered.”

“Hey! Don’t take too long with her! We want turns too ya know!” Momoha exclaimed, quickly worming her body around so she could nuzzle up into Rentarō’s neck. Hahari would have complained, if she wasn’t having her pussy wrecked by her first ever cock.

“I appreciate it,” Rentarō smiled, kissing Momoha’s forehead while still thrusting into the milf cunt in front of him. “B-but you know, I always thought of us hah… less as me going out with you all, and more us all going out with each other.” His girlfriend blinked a little in confusion before the parts of her brain clicked into place. A kinky smile spreading on her lewd face.

“Hehe, I know what Rentarō’s thinking~” She teased lightly before turning around to look at Yamato. “He wants me to make an American boobie sandwich!”

The dyed-blonde girl blinked in confusion, as she’d been sort of out of the loop of what was happening while staring at Hakari. Before even getting a ‘huh’ out her mouth, a drunk tackled her lightly and the two teachers fell down on the end of the bed. “B-boy howdy! T-this ah! This sure is a mighty f-finnnnnaahhh! Momohaaa~!” The faux american moaned, dropping her accent briefly as the ethics teacher kissed and suckled on her neck. Slightly drunk fingers still managed to expertly play with the woman’s pantie-zone to make her hump and jump almost immediately.

Mei just sat next to the humping pair quietly, occasionally interjecting with things like “Miss Hahari is a lewd woman. But only for her boyfriend, Rentarō, ’s penis.” or “I believe the current inhabitants of bone-town are two.” or “My Mistress’ vagina is so wet, one could mistake it for a child’s game of ‘Slip and Slide’”.

“Okay, Meido! We get it!” Hahari huffed after a few minutes. Though Rentarō still reached over and squeezed the girl’s hand supportively, the milf was more eager to get the maid involved. “Sit on his face, and grind your pussy into his tongue right now!”

“Huh?! Wai-!”

The order was absolute. Mei’s rear quickly landed on top of Rentarō’s entire head, reaching down to tear her panties off then open his mouth to search for tongue. She didn’t have to search long though, as her boyfriend quickly shot his taster into the maid’s leaking slit.

“Oh!”

Such a minor exclamatory, but from someone so stoic it made Rentarō‘s heart soar. “UAAHHHH!!! MY GIRLFRIEND IS SO CUUUTTEE!!!!!!” He roared, grabbing her ass with both hands and digging in to her tasty cheeks. The maid tried to return to calm, but her boyfriend’s tongue was quite the charmer. A blush spreading over Mei’s face, tiny little gasps escaping her lips, and an intense level of toe and finger curling that she attempted to hide from her companions. It couldn’t be hidden from Hahari though, who grabbed the sexy maid outfit and dragged Mei towards her breasts.

“Mommy wants you to suckle,” Her mistress commanded. An order that was quickly followed on, both as Mei was a dutiful maid but also so she could cover her quiet moans with Hahari’s loud guttural groans of pleasure. The maid was biting and kissing one tit before switching to slurp the other at a good pace, the kind of mother loving that Torotoro was so fond of. Mei was mostly keeping pace with Rentarō’s own licking abilities and with the combined effort of Rentarō and his girlfriend made his other girlfriend explode climactically on his cock, Hahari hugging Mei tightly to her chest while her body’s nerves took her to blissful highs. “Haaa~! Ooohhh Rentarō!! I love youuuu!” She cooed as the milf fell to the bed in happiness.

“I love you too.” said Rentarō with zero hesitation. Even while still somehow licking his other girlfriend to her own climax. Gripping Hahari’s hand wholesomely while Mei squirted her juices onto his chin.

Which gave Momoha and Yamato the chance to get in there. “Our time now, ya hear?!” Yamato cheerfully tackled Rentarō as soon as he sat up, the oversized bed was plenty big to handle a rough tumble with an ‘American’ gal. And as soon as he landed, Yamato’s mouth was locked over his, sending her warm tongue over his teeth and around his tongue while another girl’s tongue started rising up his shaft.

“This thing’s even scarier up close!” Momoha giggled, “It’s a good thing I’m your girlfriend, ethically I couldn’t let this thing loose in the wild!” Her tongue continued to wrap around his cock and taste the combined juices of his leaky slit and Hahari’s pussy, “Who knows what scary things it could end up doing to someone innocent!” Rising up from licking him, the woman moved her loose hoodie easily away to show how wet and ready she was, “Good thing I’m not innocent…”

“Hey, I wanted a go too…” Yamato pouted, even while she took her student’s kisses. This was a job for Rentarō!

He quickly grabbed Momoha with his legs and dragged her down onto the two of them. Then as she was falling, he flipped the whole script around by pushing Yamato off him onto the bed as well, grabbing Momoha from the air, spinning her, and placing her on top of Yamato so their bodies were atop each other. He slapped the ethics teacher’s ass to get her into position, and firmly spread the American’s legs so that the two of them became a literal sandwich. “This is perhaps the most beautiful sight I've ever seen…” Rentarō wept at his two girlfriend’s pussies squishing into each other.

“Well don’t keep us waiting th-AIP!” Momoha tried to tease but Rentarō was already one step ahead of her. Thundering his cock into her waiting sex, moving it quickly back and forth to stir his girlfriend’s slit up as roughly as he wanted before switching to Yamato.

This went on for a good few minutes. The two girls at some point moaning so much that they gave up and started making out with each other again. Rentarō’s teacher sandwich felt amazing to him, and he loved the unique feelings and reactions he was getting out of them. Momoha was a self proclaimed sex lover and dirty girl, but she was very cute when he attacked her sensitive parts. Earning a lot of moans and ‘I love you’s from the ethics teacher. Yamato on the other hand wanted to be as free as an American, but her Japanese accent kept coming loose in moments of **** pleasure. Her asshole was also her weakest point, and Rentarō was very happy to wriggle a finger into his girlfriend to make those lovely moans echo over the rooftop. Momoha’s weakspot was her clit, though pairing it with spanking seemed to be a deadly combo for her as her entire hip area soon became nearly violent at how it jiggled. The kind of punishment that Iku would love. It was almost like Rentarō was milking Momoha for love juice, squeezing underneath while spanking the top before slamming into her deepest spots and dragging out whatever sexy fluid managed to stay behind.

He couldn’t hold on forever though, “Ugh! G-Gonna…!” Was all he managed to let out before suddenly Hahari’s tongue was in his rear. Rentarō’s pleasure overloaded and he unleashed his cum directly into Momoha’s womb. The ethics teacher gasped and hissed at the jets of piping hot slime that filled her inner sanctum. He had enough sense to quickly switch teachers and finish the last half of his orgasm into his American gf. Seeding Yamato as much as he could with his deflating cock.

“Haaa…. Haa….” He panted, wiping his brow, “That was amazing… but I’ll need a minute…” Rentarō smiled, patting Hahari’s hair but also demonstrating his flaccid cock.

The milf just shook her head like he was being silly, “Rentarō~! This is a hentai story!”

He blinked, then looked down at his engorged erection.

“Oh yeah! Who wants the next round?!”

Rentarō’s sexcapades were far from over. The four women in his harem were very hungry for more, and after waiting so long to be part of a dirty fanfic or even a single doujin he was happy to give it to them.

He had Yamato lining up on her side while spreading her legs and humping her asshole, the other girls licking her big tits and gushing pussy while she moaned in bliss. Mei was taken into his strong arms and lifted under her knees for a standing fuck, Momoha helping her keep stable while also blowing raspberry’s on her tummy for fun. Hahari and Momoha made sure to give Rentarō the best titjob they could, the boy commenting how Momiji would be so jealous with how soft they were. More and more he proved that Rentarō could stand up with the best of them in terms of willpower and women pleasing. His cum was endless. Making sure that at least in this hentai universe he’d have four lovely children waiting for him in the future.

His girlfriends all lined up before him, pressing their faces in close with wide smiles.

“Cum for us Rentarō!” Momoha insisted.

“We would like to be showered in your hot sweaty male genital juice as soon as possible.” Mei overexplained.

“Let loose yer freedom on our faces!” Yamato agreed.

“You’ve done so well, please enjoy freeing your seed across our faces for the grand finale!”

Sensing the end of the fic, Rentarō’s dick unleashed their final load. It might not be canon, but by god did they all feel amazing as his love splashed over their faces. Dousing them in pure white, filling their mouths and smearing their skin, tasting and feeling so purely Rentarō.

After a heavy makeout session where they all cleaned each other off, the five collapsed into a pile onto the bed. Snuggling tightly together and smiling amongst the immense love.

Rentarou sighed, “It’s sad this story is over so soon. You were all amazing.”

“Y’all think we could ever get a sequel to this?” Yamato asked.

Mei nodded, “New girlfriends get added to the manga every few weeks. I’m sure there’ll be more chances one day.”

“Not to mention ageing up some of the others!” said Hahari, “I’m sure Rentarō wouldn’t mind a mother/daughter combo at some point!”

“Or my sister. Though we could have invited her today, if she wouldn’t have been weird about it.” Mei agreed.

“You guys are all acting like tonight is over!” Momoha laughed while sitting up, “All we have to do is imply there’s more happening at the end and we can go forever off screen!” The ethics teacher implied, quickly grabbing Rentarō’s cock and bringing it back to life.

It was going to be a long night for the harem owner.