Dream Vacation Japan (Patreon Request)

Hello there dudes and dudettes!

I am back again with a new caption, this time around a Patreon request by Jägerin110, who wanted to see a guy breaking up with his GF before taking a vacation that she herself booked.
And of course it does not turn out the way he expected!

This is a Patreon request from november. And I want to apologize for the heavy delay, just with school, work and doing multiple caps for christmas/New years Eve I did not have the time to do them earlier.
But here is the first request now, and be assured the the rest will soon follow alongside with some other captions for Patreon Commissions!

I hope that you enjoy this cap, did some stuff different with formating so the text does not take too much space.
Hope it is still ok like it it now!

And with that I say my goodbyes for now, and until next time stay happy and healthy!

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"We will see who is better off without the other" Jason grumbled to himself as he took the last few remains of his former girlfriend's belongings and packed them into a trash bag.
"She doesn't even know how good she had it with me! Bet she will be crawling back on her hands and knees any day now" he continued to think as he put more and more things into the bag.
Just a month ago he and his girlfriend Chrystal had an ugly break-up, with her complaining about him being narcissistic, not caring for her and always flirting with other girls.
Of course all of those accusations are true, yet Jason thought that Chrystal should be glad that she had the opportunity to date him. She of course did not take that comment well and immediately broke things off with him, never once looking back unlike Jason.

"Oh, but screw her if she thinks I would just take her ungrateful ass that can't even see perfection when it is right in front of her" Jason spat out, ready to throw the trashbag out.
But just as he approached his door a letter was put through the mail slot, and Jason could immediately see that it was addressed to his former girlfriend, making him smirk.
"Looks like the stupid cunt forgot to change her address. Hah!" he cackled before taking the letter.
"Now let's see what this is all about!" he thought to himself as he opened it and began to read.

Apparently his girlfriend booked an all-paid trip to Japan, and the letter was the confirmation that everything was ready and that they awaited her tomorrow, making Jason's smirk go wider.
"Well well well, would you look at that! Would be a shame if this very important information will not reach that bitch, right?" he started to brag to himself before another idea popped into his head.
"Then again it would be a shame to let such a trip just go to waste, right? And Japan is known to have some hot chicks that will probably be all over me!" he continued his line of thought, and with his mind made up about this new plan he began to pack for his impromptu trip to Japan.

The next day Jason eagerly left his apartment, driving to the travel agency to steal his girlfriend's vacation, and once he arrived and went inside he was met by a buxom brunette at the desk.
"Welcome to Dream Vacations! My name is Coco, how can I help you?" the brown-haired beauty said, giving Jason a warm smile that he hardly looked at since he was busy looking down.
"Hello, my name is Jason" he began, giving the attendant the letter he received, ogling her assets as discreetly as possible. "And I have this vacation booked that is supposed to start today."
Coc took the letter and looked it over for a bit before she froze, re-read the letter and looked back up at Jason, her brows slightly furrowed as she inspected him from head to toe.
"A-Are you sure that you booked the right package? You don't really look like our usual clientele" she started to say, but Jason just waved her off, knowing he did not really look like a traveler.

"Yes, I am sure" he just said, leaning back in his chair. "I got the confirmation after all, right? So I probably booked that vacation, right?" Jason continued, making Coco gulp slightly.
"O-Of course, sir! I am terribly sorry for doubting you!" she hastily said, looking at the letter again and tapping some things into her computer for a few minutes before addressing the guy across her.
"Well sir, looks like your flight is due in 3 hours, enough time for us to prepare everything! Do you maybe want a drink to relax? Most of our customers do" Coco said, making Jason think.
"You know, why not" he said, knowing that he was terribly nervous when it came to flying, so he better get something to not make a fool of himself. "And make it strong, alright?"
The brunette attendant just nodded as she left, returning a few moments later with a glass that was filled with a slightly pink liquid, that Jason took and immediately downed.

After that everything was normal, but after a few minutes he started to get very dizzy and sleepy.
"W-what hav-" he started before he fell asleep completely, the drugs in the drink taking effect.
Once he was fast asleep Coco took the unconscious male and carefully moved him to a room in the back, where an equally buxom blonde was standing in front of a wardrobe.
"Coco, who is that?" she said in confusion as she pointed towards the unconscious male she was carting around on a chair, and said brunette could only shrug her shoulders.
"Believe it or not, but this is our client, Lily! The one with the two-month trip to Japan. I just find it weird that a male is booking one of our special vacations..."
"Eh, why not?" the blonde named lIly just replied nonchalantly. "Everyone has their kinks, who are we to judge? Besides, he looks very girly, to begin with, so this should not be too hard."
Coco could not really argue against such logic, so instead she grabbed the unconscious guy and put him onto the table in the middle of the room so the two girls could work their magic.

They started by taking of his clothes, before they slathered him in shaving cream and shaving off every strand of body hair, leaving him completely dehaired from head to toe.
Next Coco grabbed some small breastforms that she slathered in glue before attaching them to his chest, while Lily did the same with hipforms that she attached to his ass.
Afterwards the girls grabbed a corset and wrapped it around Jason's stomach before rolling him over, grabbing the strings and pulling as hard as possible, crushing his form into a perfect hourglass.
"This is working better than expected! His girly form really helps!" Coco cheered before it turned into confusion. "But what are we going to do with this?" she asked, pointing to his nether region.
"Don't worry, I saw this in a film once" Lily just said, before taking Jason's balls, pushing them upwards hard, after which she pulled back his willy as far as possible and glued it into place.
"There, nice and flat!" Lily exclaimed proudly, allowing the girls to move on.

They took a red floral patterned dress that they pulled over his head, which in the end left Jason with a nice boob window and most of his legs exposed thanks to the extremely short length.
After that the two women took a brown wig and filled it with glue before attaching it to his head, holding it steady until the glue dried before moving on with the make-up.
For that they first covered Jason's face in tons of light foundation, giving him a pale complexion, before injecting his lips with some filler and painting them a cherry red color.
With that done they moved to the eyes, using eyeliner to make his eyes sharp and smoky before gluing on fake lashes and covering them in black mascara for extra volume.
The make-up was finished with some light blue eyeshadow, which was followed by the girls painting on some fake eyebrows that they put into thin feminine arches
At last Coco and Lily put an ornate golden armband around Jason's small bicep before adding a golden flower clip to his hair, finishing his new feminine look.

"Wow, he turned out better than I could have ever hoped for! He looks even more feminine than out female customers!" Coco gushed, loving how they made Jason look in just a few hours.
"See, I told you he was made for this! No wonder he booked this trip, he probably gets to fulfill his deepest fantasies like this!" Lily said, agreeing with Coco that Jason really made a beautiful girl.
"But anyway, we better get him to the airport! We don't want all this work to be for nothing!" Lily continued, and Coco only nodded before they started to drag the unconscious guy to their car.
But before they reached the door the brunette clerk spotted a suitcase beside the front desk.
"Oh, it looks like our guy packed for this vacation," she said, while Lily just rolled their eyes.
"Just another client that doesn't read that they get all clothes included in the travel. Just throw it away later, he can keep all the cute dresses from the vacation anyway, no need to bring his own!"
With that Coco grabbed the suitcase and threw it into the big trash bin down the streets before she and Lily moved Jason to the car and drove him to the airport for his flight with the company jet.

A few hours later Jason started to stir, slowly regaining consciousness as the drugs wore off.
"Dam, that must have been a strong drink" he groaned, slowly sitting upright from his position on the bed before looking out the window and seeing a completely unfamiliar landscape.
"Wow, did I really sleep through the whole flight?" Jason continued to mumble, the dizziness slowly disappearing as his mind grew more focused. "That sucks, I would have loved to--" he started before suddenly stopping as he saw something in the mirror that shocked him to his core.
It took a bit for his mind to catch up, but once it did he could not deny that the sexy Japanese minx starting back at him was actually just his mirror image.
"W-What the HELL?!" he screamed in shock, going over to the mirror to insepct himself more closely before starting to tug on his hair, immediately stopping once he felt the pain in his scalp.
In a panic he raced to the wardrobe, hoping to find some male clothes, but he was met with a whole female wardrobe, each dress with Asian accents, each looking more revealing than the last.
Jason started to panic more and more until he saw a letter on the nightstand beside the bed, and in a frenzy, he ran over to it and ripped it open in hope for answers to his many many questions.

"Hello Jason" the letter began, and the guy in question immediately recognized his ex-girlfriend's handwriting. "I bet you are confused, but don't worry, I will answer most questions. I really wanted to get revenge on your stupid ass, so I thought what would work best.
Then I found this company that makes dream vacations for females, and I knew that you just could not resist if you

received a letter meant for me that talked about an all-paid trip to Japan.
And if you are reading this it meant I was right about you! Anyway, thanks to the company you are now stuck as a female in Japan for the coming two months, and they do all the fun things with YOU I told them that I wanted to do. So you can prepare yourself for some fun two months!
I wish you the best,
XOXO, Chrystal!
PS: I told them that you have a rubber allergy :P"

Jason could only stare at the letter in shock, unable to process exactly what situation he is in, but before he could think more about this he heard a knock on his door alongside a female voice.
"Miss Yuki, I heard you are awake. I just wanted to let you know that tonight's entertainment is here for you!" the voice said, and before Jason could question anything an imposing male walked in.
He was much taller and broader than Jason, making the feminized guy feel weak and slightly scared as the hunk of a man approached him, but before he could say anything the hunk made his move.
He grabbed Jason around his tiny feminine waist, lifting him up and throwing him onto the bed before following, his well-muscled frame suspended above the terrified feminized guy.
"Watashi no chīsana hana, shinpaishinaidekudasai, watashi wa anata ga watashi ni nozomu yō ni ranbō ni narimasu!" was the only thing the hunk said before he smashed his lips against Jason's.
Jason's mind began to race a mile a second, trying to think of a way out, but instead he could only feel the stronger male press more and more against him as his hand snaked down to his dress.