Senpai’s Sexual Awakening

(Note: This story is part of an ongoing crossover series of stories)
Previous Story (Part XXI): [LINK]
Beginning (Part I): [LINK]
Next Story (Part XXIII): To Be Continued….

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“Now, I had suggested that we would go to the States first for this Cruise, arguing that we could use it as somewhat of an allegory for the Journey of the West!” said the captain of the Helicruiser, who was a surprisingly young man and also son of the owner of the Nanami Conglomerate by the name of Ryusui. He put his hands in the pockets of his orange coat as he leisurely walked up and down on the podium he and the other people behind the Helicruiser-Project were standing or sitting on. “Then again, those old dudes behind me weren’t as much of a fan of that idea as I was, and said that they’d much rather prefer a different route! Which brings us to this!”

 

The many interested watchers and future passengers gasped in shock at the captain’s rough words towards his boss as he pressed on the button of a small remote that had to be in his pocket, which caused a map of the world to be projected on the wall of one of the nearby docks. A single red dot lit up in Japan, representing the current position of the Helicruiser.

 

“Well, it’s not all that bad.” he continued, “I’ve already traveled around the world in that direction once before, so switching it up might make things more exhilarating for me. Instead, we would begin our journey south to Taiwan and the Philippines and then…”

 

“Huaaaaah~*” Maki Gamou yawned in boredom next to Senpai, as little drops of tears filled her eyes, “Won’t those speeches ever end?” she asked nobody of her friends in particular, all while scratching the back of her head.

 

“Hmhm!” agreed the girl next to her with a nod. “They suck!” said Yoshi, while giving the captain on the stage two thumbs-down to signal her dislike of the situation.

 

A devilish grin spread across Hayase Nagatoro’s face, “Yeah, the only people who like stuff like that are virgins like Senpai who don’t have any other things to look forward to!” Boxing his shoulder, she caused him to yelp. “Ain’t that right, Se~n~pai~?!”

 

“EEEEP!!!” The brown haired boy rubbed his shoulder, “I… I don’t enjoy this! I just…” He sweated profusely as the four girls around him edged closer towards him, practically devouring him with their teasing eyes and smug grins as they did it. “There… there’s just not much else to do at the moment. So…!”

 

“Aww! It’s just too cute seeing you try to come up with excuses!” joked Gamou, while throwing one arm over his shoulder. Seeing her friend so close to HER senpai with Gamou’s breasts pressing ever so noticeably against his arm and back, Hayase’s right eye twitched in irritation, which was something that didn’t go unnoticed by the orangette as her smug grin became even wider. “Don’t ya think so too, Hayacchi? He’s totes adorable when he gets all flustered like this, right?”

 

“Well… I wouldn’t exactly call him cute or adorable or anything!” answered the tanned girl as she tried to get her friend’s arm off of Senpai’s shoulder, but to no avail. Her face blushed in an adorable red light as Gamou simply hugged Senpai a bit tighter in response. “More like… a worm! Yes, a worm! A gooey, little worm that decided to poke his head out of the earth for ones to enjoy life for the first time!”

 

“H- HEY!” Struggling to get away from the slightly smaller girl’s tight embrace, Senpai only managed to get his arm further and deeper into her cleavage. “W- weren’t you the ones who said that we should go here?”

 

“Duh!” Hayase stopped for a single moment to pull on her Senpai’s arm, only to give him a light slap on the back of his head, “If we hadn’t come up with that idea of going on this cruise, you’d probably spent the entire summer vacation like the total loner virgin that you are and not leave your room. At least like this you will get to see a bit of the world for a bit. And don’t waste your entire time reading those pervy Manga all the time either!” she said while running her hands through his tousled hair.

 

Sakura stepped in front of Senpai and bent forward, while granting him a good look at her cleavage, which was made even more prominent due to the tight pink top she wore, “And with the reduced prices for students, it’s not like we paid that much money for it in the first place.” the blonde gyaru smiled up at him. “Who knows… maybe you’ll get a nice tan as well? Or you’ll end up finding a girlfriend here?”

 

Both Senpai’s and Hayase’s jaws dropped open at that comment, while Gamou and Yoshi couldn’t help but laugh hysterically at their reaction.

 

“A-a-a-a-a-a-a-a… a girlfriend??!” the young artist and his muse stuttered in unison with their heads as red as the many flowers on the many window stills at the now festively decorated street, spreading their sweet scent all across the town. They both looked at one another, before Hayase once again boxed his shoulder. “Ha… hahahahahahaha… hah! Don’t make me laugh! As if a loner like Senpai would ever find a girl that would want to be his girlfriend!”

 

“Hmm! Perhaps…” Gamou thought out loud with a scheming look on her face, “Buuut… if you don’t want him as your boyfriend, then it should be alright for me to-” A piercing glare from Hayase, which was cold enough to freeze blood, stopped Gamou from even finishing her sentence. “No, you’re right! Definitely not boyfriend-material! At best, someone like Paisen could hope to be adopted by a nice girl as her dog!”

 

“A puppy!” Yoshi chimed in as she pushed Sakura to the side and took her place in front of Senpai. “Wouldn’t you like that? Being a good boy for a girl and groveling all day at her feet?”

 

“AYEEEH!!!” Senpai yelped again and tried to back away from the girl in front of him, only to bounce off of the girl’s chest behind him. “I… who… who would ever want to do something like this? It’s humiliating and… and…”

 

All the girls aside from Hayase laughed at his reaction, “And you like the idea! Admit it!” Gamou finished for him, while giving his right shoulder a light squeeze. When she once again felt the weight of Hayase’s eyes on her own back, she quickly let it go however. “So, why don’t you act like a good little puppy and bring us all something to drink?”

 

Next to her, Sakura agreed with a look to the podium where the captain finally stepped back, only to hand his microphone to the mayor of the city. “Seems like those speeches will go on for quite a while longer, so having something nice to drink would make standing here at least a whole lot more bearable!”

 

“Good idea!” Hayase said, with her voice full of relief since it meant that Gamou wouldn’t be able to distract him much longer with her curvaceous body. “I could die for some maracuja juice!”

 

One after the other, the other girls agreed and before Senpai had the time or even the chance to object, they sent him off to get all kinds of different drinks for them. Navigating the streets when they had arrived here in the early morning hours, waaaaay before sunrise, with the train had been challenging enough, but now, with more than a thousand people filling each street, it was outright impossible! With the drinks for Gamou, Yoshi, and Sakura already in his hands, he walked past a foreign looking couple, their pink haired daughter, and a large white dog in search for the maracuja juice that Hayase was craving for.

 

‘Why that juice in particular?’ he thought to himself, while leaving yet another stand that didn’t offer him what he was looking for, ‘Couldn’t it have been something simple? Like orange juice or something?’ he continued to ask in his mind while stepping out on the beach, due to a lack of other options available to him.

 

In stark contrast to the city, the beach was almost too peaceful to be true! Only the soft lapping of waves against the shore, or the sounds of the news helicopter above him, accompanied him as he stepped out of the shadows of the many tall buildings all around him. Not far from his current position to the east, a long road led all the way to one of the biggest schools of the entire world, Zashono Academy, the students of which all helped out with the preparations for and even participated in today’s event with a number of stands all of their own. However, in stark contrast to the stands one might find in your typical highschool festival, all of their stands had some rather… unique twists. The last one he had walked by proclaimed in bold letters, “GRAB THE TITS AND GUESS THEIR SIZE – THE RIGHT NUMBERS WILL GET YOU A NICE, BIG PRIZE~♥” while three young girls that didn’t look all that much older than he himself was pushed out their chests at anyone who walked past them!

 

“Ah, this place is nuts!” Senpai cursed out loud, while trying his hardest to get the image he had just seen out of his head again, “And why did I even come here? It’s not like there’s a stand or anything interest-” he stopped mid-sentence as he spotted a single woman standing in the knee-deep ocean water. “I- is that the President?”

 

“Hm?” Having heard his loud thoughts, the woman turned around and answered Senpai’s question, “Oh, it’s you! How are you fairing?” greeted Sana Sunomiya, who was studying his reaction to her complete nudity with the same collected and neutral demeanor as always.

 

“P- PRESIDENT!!!” he gasped, while trying to look everywhere else but her bright pink nipples and equally pink pussy as he got closer to the former President of the art club. “Wh- what are you doing here?”

 

“Why, isn’t it obvious?” the older girl asked in retaliation, “My cousin and I also went on this cruise to see more of the world, and to further perfect our drawing talents.” she went on to say, while wading closer to him through the water, as her smooth legs were glittering and shimmering in the early morning sun. “And since this is probably the last time that I get to see Japan for a while, I just wanted to see if I can get some more inspiration out of it.”

 

Senpai raised an eyebrow, “Oh, really?” he asked, forgetting about the girl’s nudity for a moment. “And, did it work?” Did you find any inspiration?”

 

“No, not really. But that’s okay. Since, if you’re here, it normally means that your girlfriend isn’t that far away either, and, oddly enough, seeing you two together always makes me push beyond my limits!” she explained, while she was now standing right in front of him, with her hands resting on her hips as she looked him up and down. “I mean, she is here as well, right? The Cat-Girl?”

 

“Y- you mean Nagatoro-san?” the curly haired man mumbled, with his cock growing harder and harder inside his shorts as he inhaled Sana’s sweet perfume. Though she didn’t wear any clothes in an attempt to be as natural and close to nature as humanly possible, she still put on perfume and used body wash like every other girl. A combo that Senpai never truly understood, since it kinda contradicted the whole intention of her being naked in the first place. “Yeah, she and her friends kinda dragged me here in the first pla-!” His face lit up like a late evening sun as he finally completely understood what she said. “B-b-b-b-but… she’s not my girlfriend or anything! We’re just together with her friends on this cruise because… erm…!”

 

“Oh, but that’s such a shame!” a female voice called out behind Senpai, causing him to yelp for a third time that day as he felt a pair of soft hands on his shoulders, “You two would make for such a cute couple!” the distinct teasing voice of Hayase’s sister, Misaki Nagatoro, went on to say. “You wouldn’t believe how happy it would make her if you’d man up, take her hand, and then…”

 

Running her hands down his arms, past his elbow and towards his hands, Misaki Nagatoro spun Senpai around himself so that he faced her, “B- Big Sis-Toro!” he gasped, while being unable to pull his hands away from hers. This moment of hand holding lasted only for a few seconds however before the older sister then simply shoved him down on his butt!

 

“And then fuck her as good, and hard, and rough as you can with that nice dick you’re so desperately trying to hide in your pants!” she finished her sentence with a glance at the tent Senpai fetched.

 

“Who might you be?” Sana asked over the sound of Senpai covering his crotch from the other woman’s eyes, “You remind me an awful lot of his little girlfriend… You wouldn’t happen to be her sister, would you?” she continued to ask, while following closely as the woman in front of her knelt down next to Senpai. “What brings you here?”

 

“Guilty on all charges!” admitted the black haired young woman with a proud smile on her face as she raised her hands. “And I’m here for the very same reasons as you youngsters. To see more of the world and, more specifically, to watch my little sister humiliate herself as she tries to woo over her little Senpai over there!”

 

“WAH??! WHA- what are you talking about?” Senpai attempted to get up again, only to end up getting held down by the two much stronger women with relative ease as the former President knelt down on his other side. “Na- Nagatoro-san’s not trying to w- win me over… or anything! She’s just… messing around as always!”

 

“Awww! I can totally see why my lil’ sis is all heads over heels for you!” joked Misaki while casually starting to unbutton his white shirt, “But if you actually think stuff like that, you’re gonna end up hurting her feelings, y’know! She’s quite the delicate little flower after all!” she whispered into his ear, causing all hair on his body to stand on edge. “And for you to be this excited just by seeing other women… what would my precious girl think!?”

 

Senpai gulped loudly. “EEEK!! I… I… I don’t know what you’re talking ab-aba-about!”

 

Having finished opening his shirt, the black haired woman drew lines on his scrawny chest with her fingers, sending shivers and tingles all over his body, “Now, now! Don’t act so shy now!” she cooed before softly blowing against his neck. She traced her hand down to his pelvis where she then immediately reached for the bulge in his pants. “With an erection like that in your pocket, we can’t just let you go back to the others! We’ll have to train you! Ain’t that right, Artist-san?”

 

“Hm, you might be onto something there!” replied Sana, after having observed the other woman’s actions with silent interest. The former president helped Sana pull his pants down to free his throbbing erection, “You see, there will be a lot of beautiful women on this trip. I’ve seen them for myself! It gets my blood pumping with ecstasy as I think about all the beautiful ways I could draw them!” she went on a tangent, while she was still holding Senpai down on the sand with one hand while casually reaching for his frantically pulsating dick with the other. “Point is, with an erection like this, you’d only end up insulting your girlfriend and might even humiliate yourself at the same time!”

 

“Well spoken!” Misaki agreed, who was licking her lips at the sight of Senpai’s futile attempts to escape the combined girl’s assault. “So, let us do you a favor and take care of this… little problem of yours!”

 

As Hayase’s sister began stripping out of her top, Sana put her hand around the base of the struggling Senpai’s cock, “Well, ‘little’ problem might be a bit of an understatement here! With a tool like that in your pants, I can see why that girl is so enamored with you!” she said, while she watched as his resistance practically melted away with just a few slow strokes of her hand.

 

“GHMMMM…!! She’s… she’s not enamored with me!” groaned Senpai, while bucking his hips barely noticeably against the older woman’s soft palm. “A- also… Please stop doing this! What… if anybody sees us?”

 

“You worry too much, Senpai! Relax!” came Misaki’s voice to his right, “There’s nobody else here at the moment! They’re all too busy listening to those speeches! It’s just you, me, and the nude woman to your left!” the now equally naked older sister said with a lecherous grin towards Sana. “While I’m at it, might I just say that you look quite ravishing! I’d kill to get those boobies of yours!”

 

“Mmmmh, why thank you!” moaned the young artist as the other woman lifted them up, whilst weighing them in her hands. “However, may I just say that yours are perfectly fine as they are! They look like a work of art all on their own!”

 

“Oh, stop it you! You’re gonna make me blush!” Hayase’s sister teased as she flexed her fingers tightly around Sana’s tits. “But why don’t we put these beauties to work? Have you ever done a paizuri before?”

 

Leaning her head to the side, Sana thought about it for a second, “No, not really!” she then admitted. “Then again, this is my first time having sex with another girl in general, so I wouldn’t mind giving it a shot!”

 

“Hmhmm! I like you! Okay, here’s what you do!” Misaki pulled on Sana’s tits, getting her closer to Senpai’s cock, laying them down on his pelvis, “Grab your tits like this!” she said and did the same with her own boobs as she did with the other girl’s. “And then move them up and down along the guy’s cock!”

 

“Hrrrrrrgh…!!!” Senpai grunted, now feeling all kinds of warm and pleasant feelings spread from his groin all throughout his body as Hayase’s sister massaged half of his length with her tits, “Aaah, haaa, haaa…! S- stop it!”

 

“Don’t listen to him!” advised Misaki, “You see how he’s clenching his fist around the sand like that, and shaking like a leaf in the wind? He’s enjoying this!” she said over Senpai’s cute moans. “Just do what I’m doing and move your titties up… and down! Up! And Down! Up! Down!”

 

“I see!” After watching the other girl do it for a while, Sana quickly began mimicking her actions and pressed her tits tighter around the other half of Senpai’s dick, “It feels… interesting!” she said after some time.

 

“Yeah, the guys I did this with so far were all a whole lot more macho and actually did the pumping for me!” Misaki nodded with a glance at Senpai’s face. He gritted his teeth and closed his eyes as he gave himself to the pleasure of feeling the two pairs of breasts moving in almost perfect harmony over his cock. “They would just grab my titties and move them as fast and rough as they can! There’s just something special about being used by a man as if I were his personal fleshlight!”

 

A single drop of sweat made its way down Sana’s face as she watched Misaki continue with the paizuri. “That’s… quite the foul mouth you have there!”

 

Misaki grinned at her, clearly not bothered by that comment at all as she simply picked up speed with the movement of her tits, “Whatever do you mean?” she asked in an attempt to sound innocent. When Sana still looked stunned and put off, Misaki quickly apologized. “Sorry. You seem to be more of a newbie to this than I initially thought! I assumed that with a bod like yours, you’d get dicked down by hot dudes all the time, so some dirty talk isn’t anything new to you!”

 

“Sorry to disappoint you, but I usually don’t have all that much sex!” replied Sana, while picking up right where she left off and continued moving her tits in slow strokes over Senpai’s cock. “It gets in the way of creating art too much, and most guys in my class just aren’t all that appealing to me!”

 

“NNNNGH!!!!! Don’t… don’t talk… like that!” groaned Senpai, as his breath became more and more labored despite only bucking his hips lightly against their tits.

 

“Aw, he likes it!” teased Misaki as she leaned forward to lick at the top of his erection, as well as lapping up the sweet precum that kept oozing out of it. “You’re close to cumming, aren’t ya? Busting a big, fat nut all over your girlfriend’s sister’s tits? Wouldn’t that feel sooo good? Or would you be embarrassed for letting loose and losing your virginity to a girl other than my dear, sweet sis?”

 

“Ahhh… She’s… she’s not my girlfriend!” Little tears swelled up in his eyes as a pressure built up inside his balls. “But… hurr, hurr, hurr… this feels so good!”

 

Looking up at him from the corner of her eye, Misaki beckoned Sana to lean in closer as well, “Then why don’t you just cum and go ‘PEW PEW PEW’ all over our tits?” Once Sana was close enough, Misaki put her hand on the other girl’s head and pulled her even closer!

 

“MMMH?” The female artist’s eyes widened for a second as her lips met Sana’s around the surprisingly hot head of Senpai’s dick, “Hmmmm~!” she quickly melted in the other girl’s embrace and together the two girls flicked their tongues around the mushroom-shaped tip.

 

“That’sh idd… ghuud gurl!” slurred Misaki, while grinning wide whenever her and Sana’s tongues would meet one another. Within just a couple seconds, long rivulets of their combined saliva ran down the hot rod and into the deep abyss of their tits, effectively making everything feel oh-so slippery!

 

“AHHH!!! Don’t… stop! Don’t stop! Please!” pleaded Senpai, thrusting his hips at an even faster pace now, “I’m… I’m gonna… OAAAARHG!!!!”

 

“HMMMMMPH???” the two girls moaned at the same time as something salty shot out of the younger guy’s cock. Whereas Sana pulled back as soon as possible, Misaki simply locked her lips even tighter around Senpai’s length, and then right after, swallowing as much of his load as possible!

 

Seconds turned into a full minute until she finally opened her mouth again with a loud and we PLOP! A trickle of cum rolled down the corner of her mouth, but she simply wiped it away with the back of her hand. “Aahhh… That was way more fun than I thought it would be!”

 

“I have to agree!” Sana said with a look of wonder at Senpai’s slowly shrinking dick. “And it seems like you enjoyed yourself a great deal as well!”

 

“Oh, he most certainly did! Am I right?” Misaki asked the shaking boy as she pulled him up and lightly boxed his shoulder.

 

“Mmmmmmmmm… mhm…!” Senpai nodded weakly, with his eyes spinning around in their sockets as if he just came out of a way too fast carousel!

 

Misaki patted his shoulder and began buttoning his shirt again, “We seriously have to do this again sometime! Maybe with my sis next time… I’m sure she would love to share you with us again!” she then said and, together with Sana, pulled Senpai back on his feet. The two girls dusted all the sand off of him and put his pants back on. “For now though, it’s probably best if you just go back to her before she starts feeling lonely!”

 

“Y- yeah…” With shaking feet, Senpai picked up the bottles with the drinks for Gamou and the other girls and started walking back to the city, while the two older girls were watching him closely as they stayed back on the ship.

 

After a while, and with no end to the celebrations and speeches in sight, Misaki turned towards Sana with a wicked grin on her face. “You up for round two? There are so many things I could teach you!”

 

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(Story by: Mr. Akrononym)