“Sir, please wake up, we have arrived at our destination.” Paul was stirred awake by the deep voice. He looked up and saw an old sailor with the thickest beard he had ever seen before him. There was a faint smell of tobacco in the room, but the overwhelming stench of the sea prevented it from getting to Paul’s nerves.

“Wait, we are there already?” Paul asked as he rubbed his eyes. The old sailor let out a hearty laugh and slapped Paul’s back.

“Boy, I’ve been trying to wake you up for over an hour now! You are one deep sleeper I must say.” The man held out his hand and helped Paul up. Sunlight poured from a window on Paul’s right and he got a view of a beautiful sight. They were now on a tropical island that hosted an entire village of huts and were built right on the trees. The beach was big and had large coral-like trees decorating the place. And on top of that, there were so many beautiful demi-human girls all over the place!

“Wow, this place is exactly how it was advertised!” Paul exclaimed as he grabbed his luggage and rushed towards the door of the boat. Before he could exit, he felt the sailor’s large and meaty hand grab his shoulder.

“Whoa, slow down boy! You got plenty of time to enjoy yourself here, don’t try to rush things,” the sailor said, letting go of his grip.

“Uh, thanks sir,” Paul replied. The old sailor let out another laugh and gently pushed Paul out of the ship.

“Enjoy your vacation dear boy!” Paul watched as the ship turned around and slowly sailed down to the horizon.

The young human man found himself on a dock just outside of the village. The hue of the sky indicated that it was still fairly early in the morning. Paul let out a long sigh of relief as he felt at ease from the wholesome atmosphere of the place.

“Welcome!” A feminine voice shouted from behind Paul which nearly caused him to tumble over. One of his suitcases did fall off the deck but was caught by a long snake-like tail.

“Whoa, you should be careful there!”

Paul focused his gaze on the tail and followed its movements back to its owner. He gasped at seeing a lamia carrying his suitcase by her tail. “That was a close one, you should be more careful next time!” The lamia said as she slithered over to Paul. She had a group of other demi-humans with her, all of them female. Paul caught his gaze turning south once or twice but stopped himself before the various demi-human women noticed.

“Oh sorry, this is my first time being surrounded by so many demi-humans before!” Paul scratched his head and laughed in a nervous manner.

Just then, Paul felt a gust of wind and someone snatching his remaining luggage. He looked up to see a harpy holding his remaining luggage in her talons.

“Don’t worry sir, we will take your luggage to your condo so you may enjoy the resort’s many features as soon as possible!” The harpy explained before flying over to the lamia to grab the remaining luggage.

“Wait, are you sure you can carry all of that?” Paul asked, wondering how a harpy could carry so much stuff with so little issue The harpy giggled and shook her head.

“Are you questioning my strength, human? I can carry more than double of what you have!” And with that, she took off towards the village.

Another demi-human, a minotaur, approached Paul and gave him a little bow.

“While we know most guests would like to make themselves comfortable, we encourage you to begin to relax at the beach. Life can be so stressful sometimes, it’s important to treat yourself nicely,” the minotaur said to him. She gently took his hand and began to direct him to the beach.

“Please, allow nature- and us lovely ladies, to wash away all your sorrows~”

Shortly after, Paul found himself under the shade of one of the coral trees. The beach chair he was given subtly modified itself to accompany his body and any movements he made. The sweet smell of the ocean combined with the sound of the waves made him feel total bliss. He also had full sight of a volleyball court and could enjoy watching the many bikini clad women duke it out with each other. Paul had taken the minotaur’s advice and all his worries seemed like distant memories to him. But as the time went on and the sun crawled to the highest point that day, Paul realized something: there was not a single man in sight. Heck, there wasn’t a single human around either, the only people in the village or on the beach were demi-human women.

“Is something wrong sir? Aren’t you enjoying your time here?” Paul heard the familiar voice of the minotaur speak. She was standing behind him holding several coconut drinks in her hand.

“Oh, I’m fine, I’ve just noticed there isn’t a single other human in sight.”

“Well this is a resort run solely by demi-humans, it would make sense that there aren’t a lot of humans.”

“Yeah, but like, I have not seen a single other man here either. Shouldn’t there be plenty of other people vacationing here too?”

“Oh they are, like Jolene over there. She came to the island with a variety of other guests a few days ago.” The minotaur pointed to a mermaid sitting on the rocks. The ocean breaking on the rocks drenched her every now and then, but Jolene clearly didn’t mind.

“Oh… in that case.” Paul stood up from his seat and walked over to the mermaid. “Hey, how are you doing?” Paul tried to smooth talk her, but tried his best not to come off as desperate or rude. The mermaid looked at him but didn’t smile.

“Oh, uh, hi.” She said before turning her attention back to the sea.

“So I heard you are on vacation too?” Paul said, hoping to start a conversation.

“I am.”

“Uh… do you want to chat?”

“Not really.”

“Is something wrong?” The mermaid didn’t respond.

“Uh, is there something wrong Jolene?” Paul asked again, this time backing off as he became a little concerned. Jolene turned around quickly with a disgusted look on her face.

“Who told you my name?” Paul was taken aback by the mermaid’s total mood whiplash.

“I did,” the minotaur said as she stood next to Paul’s side. The mermaid let out a sigh and face-palmed.

“Macey, I told you not to tell anyone my name!”

“Sorry dear, but I thought you could use the company of another vacation goer,” Macey said in reply.

“I’m sorry, I didn’t mean to bother you,” Paul backed off a bit and was about to head back to his chair when Jolene called out to him.

“Oh, you don’t know how mermaids work human…” Her voice was a bit ominous but at the same time, oddly alluring. Paul couldn’t help himself and returned to the mermaid.

“You annoyed me and there is only one way to settle this-”

“Whoa, calm down lady! I didn’t mean to piss you off, we don’t have to-”

“I was talking first, don’t interrupt me! For annoying me, we have to race.”

“Oh a race? Uh… that doesn’t sound quite fair with you being a mermaid.”

“Who said we were running on land?”

“That’s- hey that would make it unfair for me!”

Jolene let out a mischievous giggle and looked over at Macey who in return gave a knowing nod.

“If you win, I’ll go out with you, but if I win… you got to drink Macey’s special surprise~”

“Special surprise? What do you mean?” Paul looked back at Macey. The minotaur had grabbed her large melons and squeezed them slightly while giving a seductive smile.

“Minotaur milk? That doesn’t sound like much of a punishment.”

“Hehehe, then you won’t mind losing~” Joelene pointed to a rock a little out into the sea. “From here and back, that will be our race.” Joelene hopped into the ocean and waved to Paul to meet her at the starting line. Paul wasn’t enthusiastic about this, but he decided to go through with the race, at least to make Jolene happy.

The race began shortly and it ended as anyone would have guessed. Even if Paul hadn’t had his leg grabbed by a crab girl by mistake, Jolene would still have made it to the rock and back before he was even at the rock himself. Paul didn’t mind, he just hoped the race would help calm Jolene down. He managed to drag himself back despite his injured and slightly bleeding leg. Jolene had stationed herself back on her rock and was in a better mood.

“Thanks for letting me win, I was totally not a match for you~” She said in a teasing manner. Paul laughed along with her glad she was no longer upset.

“Yeah, haha, I only let myself use 2% of my power,” Paul replied.

“Hehe, don’t get too excited, you remember our bet, right?” Paul felt someone tapped his shoulder and turned around to see Macey. Her apron appeared wet around two key points on her chest. The minotaur handed Paul a coconut filled with her rich and creamy milk.

“Drink up hun,” Macey said. Paul had drunk minotaur milk before and didn’t see how this could be a punishment of any kind. He took the coconut and drank the whole thing down rather quickly.

“Ah, that tasted very good!” Paul threw the coconut to the sigh and stretched. “That was the best milk I’ve drunk in a long time!” Macey and Jolene began to giggle though Paul could tell they were laughing at him. “What’s so funny?”

“Oh, it’s nothing Paul,” Jolene said, “I do like your new ears though~”

“New ears? What are you-” Paul stopped himself short as reached for his ears. He expected Jolene was pulling some prank on him, but Paul’s blood turned cold as he didn’t grab soft and flexible human tissue. His ears felt a bit rough and feeling their shape, they may have been fin-like.

“Wha- what’s wrong with my ears!?” And two demi-humans began to giggle at Paul’s reaction which in turn made him angry. “Hey, what did you two do!?”

“We didn’t do anything Paul. Though, you should never drink a minotaur’s milk after pissing off a mermaid~”

“What are you talking about- gah!” Paul fell to his knees, his vision getting slightly blurry and his nose became stuffy. He felt pressure in his chest but it was pretty slight at the moment. Still, it was enough for him to know something was wrong.

“No, please, what did you do to me!?” Paul noticed how rather… hi-pitch his voice now was. He brushed off his hair that began covering his face- wait, Paul had short hair! Was his hair beginning to grow longer?

“Why should we ruin the surprise? It’s more fun watching them slowly figure it out~” Paul had several guesses what could have been happening to him, and he felt his chest seemingly pulsate and push out a little, he began to narrow down what was happening.

“You are making my muscles bigger? These are quite some pecs you gave me.”

“Hehe, he thinks those are pecs!”

“Huh- gah!” Paul’s “pecs” grew longer and as Paul’s vision began to clear, he noticed his nipples were now a bit erect. He noticed that he wasn’t getting bigger muscles, in fact, his body had become devoid of any and all body hair and he looked a lot more slim now. His chest was bigger than ever but the pressure he felt was still there.

“T-these aren’t pecs, they are more like-”

“Boobs?” Jolene intervened with a mischievous laugh.

“Oh no, I’m changing into a woman!”

“Hehe, he finally figures it out!”

Paul stood up and pointed at Jolene with an angry expression on his face. Paul looked over at the ocean for the briefest of seconds and while he didn’t catch every detail, he noticed in his reflection that his upper body and face looked so… alien to him now.

“Stop this at once- ooo!” Paul grabbed his sizable bust which nearly caused him to topple over. He managed to get his footing and pointed at the mermaid again. “Jolene, you- aaahhh!” Paul wasn’t ready for the explosion of pressure above his ass. His swim trunks ripped, leaving the poor transforming man naked with what was left of his clothing now hung at the end of his long, lizard-like tail.

“Those were new- ugh, don’t look at me!” Paul fell to his knees again but this time on his own volition. He used one arm to cover his still expanding bust while using the other to cover his junk. He could feel the weight of his ever growing melons and just how… bouncy there were. It took a lot of will power for Paul to not play with his large rack. Paul noticed that his ass was also now big and round, possibly having changed when his tail formed. He was clearly more she than he at this point, but there were still some final touches that had yet to be made.

“Oooooo….” Paul let out a slight moan as his thighs began to become extra thick. On top of that he felt his bones near his waist readjust themselves to make room for something. “What is this feeling?” Paul’s hips began to widen as a womb for sheltering a child began to form inside of him. The extra thickness he had obtained started to close in on his penis which began to be squeezed by his thick thighs. Eventually it couldn’t take the pressure anymore and with another moan, it retreated into his body, leaving behind a wet slit.

Jolene and Macey looked over at each other and smiled. This wasn’t the first time they had witnessed this and they knew Paul just experienced the “good part” as they liked to call it. Paul caught her hands reaching for her new sex, but managed to catch herself. Somehow, as estrogen began to pump all over her body, Paul still managed to keep from pleasuring herself. The last explosion of hormones was met with one last change as Paul’s bust grew a few sizes larger until they settled on a healthy pair of perky d-cups.

The new lizard woman panted for a bit, her mind still trying to wrap around what she just went through. Shadows overcast her and as Paul looked up she could see Jolene and Macey towering over her.

“W-what did you do to me!?” Paul shouted in a mixture of anger and confusion. The two other girls giggled at the new woman’s expense.

“Remember when you ask why there are no human men around?” Macey said, shaking her finger in Paul’s face. “Well the truth is, there are plenty of human men around, they just aren’t that way at present.” Paul looked at the minotaur with shock.

“So you mean-”

“Oh, I’ve been a minotaur all my life dear, but Jolene on the other hand….”

Jolene let out a giggle and poked at one of Paul’s boobs.

“Hey, don’t touch these!”

“Relax Pauline, you don’t want to stay naked now do you?”

“I- wait, Pauline!? Don’t call me that!”

“What, you know any other woman named Paul?”

“No, but- change me back! This is against my rights!” Paul felt something slip off of her tail. She turned back to see Macey checking over his torn trunks and she seemed to be judging them.

“She’s an E-cup, Macey. Or a d-cup- her boobs are big~” Jolene shouted over to her friend.

“An E-cup!? Why did you make them so big?”

“Hehe, all that body fat had to go somewhere Pauline~”

“Stop calling me that!” Paul began to stand up but quickly remembered she was naked and bunkered back down. Though not too long after, Macey handed her a one-piece bikini that looked oddly a lot like her old swim trunks.

“I’m not putting those on!”

“Fine, then stay naked, it’s not my problem,” Macey replied.

Paul stared at the swimsuit, it had a large hole in the back that seemed to be the perfect size for her tail. She let out a sigh and begrudgingly put the swimsuit on. Paul didn’t want to admit it, but it felt nice. The swimsuit complemented every inch of her new body, showing plenty of cleavage and skin while still holding her large melons mostly in place. The way it rubbed against her skin, especially the odd sensation near her crotch- there was something about it that felt magical. Paul took her first steps as a woman and immediately could tell how odd but also how normal it felt to not have a large member between her legs.

Paul had almost forgotten her predicament as she took the time to admire her new body. She made several sexy poses and watched her reflection in the blue ocean.

“Wow, I made you some new clothes and I don’t get so much as a thank you?” Macey’s words brought Paul back to reality, though she wasn’t too angry this time.

“Uh… thanks-” Paul felt perplexed, thanking the person who was responsible for her transformation. She was still angry but she didn’t see any point in arguing back at this point. It’s not like they were going to change her back anytime soon.

“So Pauline, what are you going to do with your new body? Want to go for a swim with me?” Jolene said, wagging her tail a bit. Paul looked at the mermaid and frowned, but she began to hatch a new idea as she looked back at the rock.

“How about this Jolene, let’s have another race to the rock and back!”

“How about you race around the entire island instead? You both have bodies capable of achieving that,” Macey chimed in.

“Oh, and what exactly are you betting?” Jolene said, clearly ready to accept the challenge.

Paul gritted her teeth as she spoke. “If I win, you change me back to normal! And if you win-”

“You have to go on a date with me~” Jolene interrupted. The lizard woman’s face turned red as the mermaid continued to tease her.

“What, I thought you were into demi-human girls~” Paul was left speechless and slowly walked to the rock Jolene usually sat on. Jolene met up with her shortly and the two waited for Macey to give them the cue to start racing.

Not too long after, Paul found herself swimming in the ocean. But this time, things were a lot different. Besides the feeling of water squeezing their way between her boobs (causing a cluster of bubbles to rise from her cleavage every time she jumped in and out of the water) she was a lot faster. Her new tail gave her so much power and precision that she could only dream of having it as a human. Heck, for some reason, maybe due to smoother skin or less baggy swimsuit, her new sex seemed to assist her as well.

The race went by so quickly, Paul didn’t realize she had already made a successful lap around the entire island until she was nearly 200 meters past the finish line. She even managed to return to it before Jolene could ever get there. Everyone was shocked, including Paul who was surprised just how good it all felt.

“Wow, you managed to beat me…. Alright, a bet is a bet.” Jolene motion Macey to go grab something. Paul let out a sigh and motioned both of them to stop.

“Um… actually, can we put that on hold for a bit?” She asked a little shyly. Jolene and Macey looked back at one another and then back at Paul with a knowing look. “I mean- I wouldn’t mind being a lizard woman for another day or two. It hasn’t been all that bad. And Jolene-” Paul turned to face the mermaid. ‘Uh, you can call me Pauline if you like.”

“Hehe, oh really? You love being a demi-human already?”

“I- Ok, you got me, I actually enjoy it quite a bit.” The minotaur and mermaid giggled and Pauline joined them in with them.

***

Pauline’s vacation was scheduled to last for two weeks and she spent every moment during those two weeks adjusting to her new body and spending time with Jolene. The lizard girl has already found joy and acceptance with her body from the race she had with Jolene, but during those two weeks, Pauline found herself enjoying it more and more. Despite winning, Pauline and Jolene still had a date together on the last night of Pauline’s vacation, just mer hours before she had to return home.

It was late in the evening, the sun sitting right on the horizon line turning the sky red and orange while the ocean reflected its golden glow. Pauline waited on the dock with Jolene and Macey by her side. She was now wearing a summer dress and her suitcases were now packed with clothes that looked a lot like her old manly ones, but were much more feminine and complemented her new body. The ship had not arrived yet and was running a bit late, but it did allow the three to share some last words with each other.

“So, I assume you had a good time here?” Macey asked, helping carry out the last few pieces of luggage Pauline had. The lizard girl smiled and nodded.

“Yes, these were among some of my favorite days of my life! I mean, I still would have preferred you didn’t bet me into it, but… well, I guess I’m glad you did~” Pauline replied.

“Speaking of which,” Jolene called out from below the dock. “Macey, I believe it is time.” The minotaur nodded in return and pulled out a small bottle out of her massive cleavage.

“This will transform you back into a man, Pauline.” She handed it over to Pauline. The lizard woman simply stared at the bottle for a moment. Macey and Jolene were about to comment, buty they knew what Pauline was thinking… and what her decision would be. Pauline gently pushed Macey’s hand away.

“I… I don’t see what’s wrong with staying like this for a bit longer. My friends, family, and even my boss already know what happened to me, so it’s not like it would be a surprise to them!” The minotaur and mermaid looked at each other and smiled.

“The option is always there Pauline, so don’t feel forced to stay this way.”

“Haha, yeah….” Pauline scratched the back of her head while giving a slightly nervous laugh. Just then the sound of a loud horn was blown and a ship sailed into the dock.

“Well, this is my ride, thanks for the wonderful memories guys! Especially you Jolene, I hope to see you soon~”

Pauline gave her two friends a hug before she moved into the ship with all her belongings. Inside, she came face to face with a familiar face.

“Hmm, I was supposed to bring back a gentleman named Paul,” the old sailor said. Pauline giggled a little. The old man smiled but let out a little sigh. “Ah, lass you’ve changed quite a lot from the last time we met. Are you ready to head home?”

“Of course~” And with that, the ship began its long voyage back to the mainland. As the ship left the dock, Pauline noticed something was in the pouch of one of her bags. She found a bottle very similar to the one she drank before and it seemed to have Macey’s milk in it. She found a letter next to it which read: “Pauline, if you wish, why not give this to a friend? I’m sure they’ll learn to love it just like you~”

Pauline smiled and placed the bottle down. “This was a wonderful vacation~”