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=== 3RD PERSON POV ===

Amber and Lily look out the window as the pilot announces the Hawaii Islands within sight.

The green dot on the horizon slowly grew until they became distinct landmasses. “Oh my god, we’re finally here!” Lily says excitedly, pointing the islands to Amber outside the window. The lush green islands of Hawaii come into view below, crystal clear turquoise waters lapping against pristine white sand beaches. Palm trees sway gently in the warm tropical breeze.

Two conflicting emotions plague Amber’s mind as the beautiful islands pass below them. Excitement, because of the vacation, and anxiety, because of what comes next.

“Wow…it’s so beautiful.” She says softly while admiring the view out the window with Lily. It was enough for her to forget her worries briefly.

“It is, isn’t it? I wonder where we’re staying this time.” Lily wondered. “It was a hotel in Paris and Bali, but I’ve been told that more private guest houses were preferred for…you-know-what.” She avoided mentioning the sex activities they were going to do.

“Oh yeah…” Amber nodded, trying not to think too much about it. “I hope it’ll at least have a nice pool and beach access…” Her thoughts drifted to what the bedroom would look like. Would it be romantic, or designed purely for function? Would she hear the others through the walls? The thought made her cheeks flush red.

“Knowing him, it definitely will. He likes to go all out.” Lily remembers her past vacations with you.

Amber couldn’t help her excitement. She was really looking forward to the accommodations now. The first-class trip was quite the eye-opener for her.

The plane landed at Daniel K. Inouye Airport, Hawaii’s gate to the world, and the four of you regrouped to collect your luggage. At the terminal, a chauffeur was waiting to bring you to your accommodation. The four of you boarded the van, heading to your lodging.

The trip was eventful, disembarking from the van at a pier, boarding a boat ride to another island, and then riding another van until you reached the guesthouse. It was named the ‘Old Lahaina House’ and it was big, capable of rooming up to ten guests.

The four paused at the front of the medium-sized property to take it in. Rather than looking expensive like many hotels before, it looked more comfortable and homey.

“Well, it’s definitely beautiful.” Lily said, looking around. “Cozy- though isn’t this a bit big for only four of us?”

“The other guest houses were packed. It was the only one close to what we needed.” You explained. “It would be private, have a pool, and be near the beach. I couldn’t get one with a beachfront.”

“It’s perfect for our needs.” Scarlet agreed. She preferred it over hotel rooms to be honest- even if they were 5-star hotels. Scarlet was slightly on the noisier end when it came to voicing her pleasure. Here, she’d be safe not to hold back.

They headed inside with their luggage and checked out the rooms. Just like the atmosphere it presented outside, the interior was nice and comfortable.

“This room is mine!” Lily jumped on the bed when she found the perfect room for herself.

“I guess I’ll pick this one across.” Amber settled for the one adjacent to Lily’s. It was close and that was all that mattered. She was still feeling overwhelmed after seeing you rent out an entire house for the month-long vacation.

They brought their luggage to the rooms and returned to the living room where you and Scarlet waited.

“So, what now?” Lily asked.

“Feel free to stretch out your legs and walk around for a little.” You told the girls. “As for you Amber, we’ll spend tomorrow morning studying after breakfast.”

Amber blinked. She had completely forgotten about that. “So…what’s the plan for my…studies?”

“We’re going to spend three hours every morning for your tutorial session. The rest of the day will be yours to decide.” You waved the course material in your hand. “Your graduation is the focus here, so make sure not to go too wild on drinking okay? Can’t have you hungover in the morning.” You turned to Lily next. “That goes for you too. Don’t drink so much you lose control.”

The warning was clear. With the three of them off contraceptives, anything could happen. You couldn’t let them end up getting pregnant with a different man, could you?

Amber apprehensively held her arms. ‘That’s because you just want to be the one to do it.’ She thought with a wince. That was part of the agreement to join your private sex circle after all.

Lily noticed Amber’s unease and stepped in to help her. “Since we’re free today, I’ll take Amber out and see the place. Is that alright?”

“Of course. Enjoy yourselves.” You weren’t the kind of person to keep your girls around. They were free to do as they pleased.

Lily dragged Amber outside by the arm. “Look, I know it’s a big deal to you…but let’s make the most out of the vacation, okay?”

“…okay.” Amber shook herself out of it. She was in Hawaii! If her friend Lily says the vacation was worth getting pregnant for only one month, then it must be great!

“Good! Now let’s do a little exploring!” Lily grinned. She wanted to get her friend comfortable.

They spent the afternoon and early evening finding places like the convenience store, some local restaurants, and souvenir shops.

=== YOUR POV ===

The next morning, Amber awoke to a surprise.

She was too excited to sleep properly, and woke up early because of it. She quickly dressed up and headed down. As she entered the kitchen, she found you cooking breakfast for everyone.

“Good Morning.” You warmly greeted Amber while she stood there stunned at the kitchen entrance. “How was your first day?”

“It was…nice.” Thrilling even. Exploring the area with Lily was every bit as exciting as she imagined. It was Amber’s first time in Hawaii and it was like a dream.

“That’s great. Just wait a few minutes for me to finish up breakfast and we can eat.”

Amber had to check the clock what time it was just to make sure. It was seven in the morning, quite early, and you were here cooking breakfast for everyone. It was a side to you she hadn’t seen before.

“Your semester coursework is on the dining table. You should look at it while waiting.” You flipped the pancake over while nodding your head in the direction of the dining room. “I don’t know what you like to drink so I just prepared warm chocolate for you on the table.” It was prepared early because you knew Scarlet and Lily both liked chocolate in the morning.

Amber quietly walked over to the dining room table filled with a bunch of papers. It was the syllabus for the entire semester. There was a decent chunk of lessons, and she wondered if she could even study everything in a month.

You appear shortly after with two plates of pancakes. One you placed in front of Amber, the other on the chair beside hers. You sat next to her to discuss your plans for the next month.

“Since this is your first time, let’s set things straight.” You gave Amber a look. “I won’t limit what you want to do, as long as it doesn’t go against my rules.” You poured yourself a mug of hot choco- though slightly cooled. “Rule one, follow my orders.”

Amber grimaced. “Are you going to make me do crazy things like walk out in public naked?”

“I’ve never forced any of the girls to do that.”

“I can’t believe I’m doing this…” Amber murmured. Still, she couldn’t back out now. Especially when the vacation was looking up to be the most memorable in her life- aside from the consequences of getting knocked up- even if it was just for a month until the tiny baby bump showed. Then, she was free to abort it.

“Second rule, no protection. You already know that one.” That was what Amber was worried about most. She would’ve been fine becoming some sex toy for a vacation of this level, but the assured pregnancy was mortifying to think about. How did other girls agree to such a thing?! Then again, here she was doing the same thing.

“Third rule, no boys. You know why.” Of course Amber knew why. It was to ensure that it was only him that got them pregnant. It was still quite the shock you learn that you had an entire private club just for your impregnation fetish.

“But…I will give you an incentive.”

“What…incentive?” Amber narrowed her eyes suspiciously.

“I know you’re nervous about…well, everything.” You had a plan to make sure Amber would slowly come to accept your side of things. It was a little game to you, poking her defenses until you found the weakness to penetrate. Your goal? To end the vacation with Amber’s pretty little egg, nice and fertilized by yours truly.

“Each time you pass a test, I’ll give you the choice to avoid a creampie when we have sex.”

That…that…what was that going to do?! She could avoid getting creampied the first few times, but she would then run out of passes to use! Then what?! Just surrender and let herself get knocked up?!

“That’s not fair when Lily told me you always make sure to get us pregnant during these vacations…” Amber snapped.

“Not really, I have a schedule. To maximize my virility, I always limit the amount of times I cum during a month. I have to make sure I pump it all exactly where it needs to go.” Right inside fertile wombs. “Spread that across the three of you and it becomes harder.” That was a lie. You creampied Scarlet just before your flight yesterday, followed by a creamy goodnight gift just before you slept. That was already two loads inside the blonde German model on the first day.

Amber bit her lips nervously while she considered the small escape option. It was unlikely she could avoid getting creampied for one month straight, but she could time the passes to make sure you pulled out during her most fertile days.

She doubted it would stop you from just fucking her pregnant, but less cum inside during those days, the better.

“…how many tests do I have?” Amber was going to try and pass as many as possible. Even if it was risky, the small chance of making it out of the month without getting knocked up was enough to light a fire inside her.

“You can retake all of them. Even the ones you didn’t fail.”

Amber’s eyes widened. That was a good chunk of tests, maybe enough for her to survive the one week she was fertile.

“I’ll go study now!” She needed to collect those passes if she wanted to save her dignity.

“Let me go grab the materials. I’ll be back shortly.” You stood up and disappeared up to your room. A few minutes later, you returned with the notes for the first lesson. “Here, I’ve simplified some of the lessons in my notes. Feel free to compare it with the books.”

Amber carefully took the papers from you and began looking them over.

“You should eat first.” You pointed at the pancakes left in front of her. Your group just arrived the day prior, which didn’t give you much opportunity to find the local market for ingredients. So you just settled for buying quick-to-prep meals like pancakes for now. “Helps you focus when you’re not on an empty stomach.”

Amber starts nibbling on the food absent-mindedly, her focus directed at the lecture notes you provided to her. While she was eating, the third person to wake up appeared in the dining room.

“Morning.” Scarlet greets you with a kiss. She was dressed in a comfy lavender nightgown, the same one you fucked her in the night before.

“Morning, sweetie.” You reply after finishing the kiss. “Why don’t you come join us for breakfast? We have pancakes.”

“Oh you-” Scarlet pinches your cheek lightly. “You’re always eager to cook us breakfast during these vacations.”

“Can’t I treat you girls? It’s rare for us to have vacations like this together.” You grin at Scarlet. That’s why these vacations were special. You and the girls bonding together as you knock them up. It helped develop bonds between all the girls in your club together with you.

“You’re so sweet.” Scarlet sits across you and looks at Amber studying. “Studying already? It’s just seven.”

“Well, she joined to pass the subject. I’m still going to help her.” You answered. You kept the little incentive hidden for now. The two of you casually talked while eating breakfast, Amber silent to your side as she focused on studying.

30 minutes later, Lily appeared at the dining room with a yawn.

“Mo-rning~” She stretched like a cat before plopping herself in front of the last plate of pancakes. The rest of you were finished eating and were just content to sip on chocolate while she dove in. “So, any plans for today?” She asked while chewing on the pancakes.

“I’ll stay here and help Amber study until…around 10?” You looked at the clock. “From there we’ll see.”

“So that means we’re free for the morning.” Scarlet nodded. “I still haven’t unpacked and now seems like a good time for it.”

“I’ll unpack too. Nothing to do this morning.” Lily poured herself a second mug of chocolate. “We’re eating out for lunch, right? Can we find a pizza place? I’m craving for pizza.”

“Sure. We’ll go with pizza for lunch.” You agreed.

Just like that, you had a schedule for the morning.

=== YOUR POV ===

Lily plopped down beside the two of you halfway through Amber’s tutorial session that morning.

“Already done unpacking?” You gave Lily a look.

“Yep!” She had spent the past hour and a half unpacking while you and Amber went over her lessons. “I came to check on how Amber was doing.”

Amber groaned. “I can’t believe I’m studying on a vacation like this…”

“Wasn’t that our agreement?” You chuckled. “That you would join us to pass my subject? The vacation and the studies come hand-in-hand…”

“Yeah…” Amber sighed. “It’s just…I didn’t expect to be invited to this kind of vacation to pass my subject.” Just because she agreed to join didn’t mean she liked it. She tried to seduce you into a free-use sex deal on her terms, but it wasn’t enough. Now she has accepted to go on your impregnation-spree vacation.

“But the vacation was worth it, right? It’s not every day you get to enjoy Hawaii like this.” Lily looked around at the house you rented out for the duration of your stay.

“It’s…certainly shocking.” It was. Amber hadn’t expected something like this from you.

“If you’re still unconvinced, you get your own personal masseur!” Lily eagerly leaned on you. “Can I get one of your massages now~?”

“I’m supposed to be helping Amber…” It was a weak attempt to dissuade Lily and she knew it.

“Come on!” She’s just gonna be studying there anyway. And you’ll still be here to teach her!” Lily pushed her advance, going as far as wrapping her arm around yours and pressing her tits on it.

“Oh fine-” Getting a feel of Lily’s boobs lightly squished against your arm was enough to convince you. You placed Amber’s lecture on the table and stood up to walk behind Lily. “Teasing me with your tits…someone needs a punishment!”

“Oh-!” Lily giggled when you gave her tits a nice grope. “That’s not where you’re supposed to massage me~” Amber watches quietly as you gently grope Lily’s boobs. “We can do that later~” Lily playfully takes your hands off her chest and moves them to her shoulders. “Start here first!”

“As you wish, milady.” You grant her wishes and begin massaging Lily’s shoulders.

Lily moaned softly as your hands worked over her shoulders. “Mmm, that feels really nice,” she purred, arching her back slightly. “I knew I could count on you to help me relax.” Lily’s breathing slowed and deepened the longer you massaged her. Her muscles began to loosen under your touch. She seemed to melt into the chair, completely at ease.

Amber silently watches as you continue to massage Lily, moving down to her arms once you are done with her shoulders. “Is it really that good…?” Watching Lily melt under your hands surprised her. Another little skill she didn’t know you had.

“Mmhmm~” Lily groans as you knead her back. “And you get to ask for it any time you want. Though, you’ve got to give him a favor in return.”

Amber had an inkling what kind of favor you would ask in return. Was one massage really worth getting fucked unprotected?

To Lily, it was.

Amber refocused on studying, but would sneak glances at the massage you were giving to Lily. You soon move from her arms and shoulders, working your way down her back until you reach her stomach.

“Wait! Let’s do this part on the sofa.” Lily halts the massage. “It feels better when I’m lying down rather than sitting here.”

“If that’s what you want, baby.” She suddenly squeals in surprise when you carry her out of the chair bridal style and bring her to the living room. You lay her on the sofa and continue the massage, rubbing her stomach all over.

“This is your favorite part of the massage, right?” Lily giggled while you focused your attention on massaging her stomach.

“I also like it when I get to massage this-” You grope her left boob. “-this,” Your right hand slipped into her underwear and fingered her vagina. “-and lastly, this.” You spank her ass.

Lily gasped. Her cheeks flushed crimson, and she squirmed under your intense gaze, feeling incredibly exposed and vulnerable.

“Aren’t you quite the pervert.” She smiled. “Do continue…” Lily fixed her position on the sofa to lie facing up. She tugs her shorts off slightly, teasing a little show of her hips. “Well? Aren’t you going to help me get them off?”

“Of course.” You grab her shorts and strip them off her. Black ribbon panties meet your gaze as Lily angles to show them off to you. “How about you help with mine too?”

Lily eagerly removes your shorts and yanks down your underwear to see the hard erection awaiting her.

“Oh my-! This is a wonderful surprise!” She acts shocked before gazing up at you naughtily. “Looks like this little boy deserves a good reward for making my body feel so nice.”

“I think you know what kind of reward it deserves.” You rub your cock on her cheek.

“Mmhmm~ This little thing needs some love~” Lily gives the tip a juicy kiss. “-and a lot of lubricant.” She spits saliva on it before giving it a few strokes, followed by her mouth taking it in.

“Ahaha, quite a mouthful there, Lily,” you chuckle, impressed by her enthusiasm. “But I think we know where it really needs to go.”

Lily pops off your cock before giving it a few more strokes. “Yep, just getting it nice and ready…” She turns around and positions herself on all fours facing the dining room where Amber was watching the two of you get hot and naughty.

“I believe it’s my turn to get a massage.” You whisper in Lily’s ear while rubbing your tip against her wet vagina.

“I’ll give you a nice raw massage…right in here.” Lily sways her ass a little to rub against your cock. “A special cock massage coming right up. Your cock, my pussy, and lots of happy endings~”

You smile, finding it funny that Lily already expects these kinds of things from you. This babe gets whatever she wants! “Mhm, why not? A special ‘cock massage’ it is. If you insist, then so be it, princess!”

You push into her wet lips, parting her folds with your manhood. Lily moans lightly as you pierce her insides, missing the feeling of your cock inside her. You keep pushing deeper until you reach her cervix and give her womb its good morning kiss. Once you were completely sheathed inside Lily, you took a break to enjoy the moment. You and Lily were facing the dining room as you penetrated her over the sofa in full view of Amber.

“Hi Amber! Enjoying the sight?” Lily joked while she got mounted over the sofa like a dog.

Amber had been to frat parties and cheerleader orgies, saw Lily fucked by numerous boys just like her, but never did she see Lily look this content with anyone. Seeing her professor mount Lily over the sofa was one sight she hadn’t ever expected.

“Why don’t we show Amber a good show? To make her understand what this vacation is for?” You whisper to Lily while slowly sliding in and out of her pussy.

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