themariogamer

Boat Trip Feminization

Published: September 26th 2023, 7:04:45 pm

Hello there dudes and dudettes,

I am back with another caption for you all!
This is a commission by Ivy (Misterious6488), about a dude that gets feminized by his GF after she caught him cheating.
The devious part? She will make sure there is no escape by getting him on a boat trip to an island!

I hope you all enjoy, and until next time stay happy and healthy!

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"Hey Ivy, how long until we are there?" Owen asked his girlfriend, the salty sea breeze blowing into his face as she steered their motorboat across the lake.
"Don't worry hun, we are nearly there. You should see the island in a minute or two" she just answered with a smile, making sure they stood on course.
"Okay, if you say so. By the way, what exactly is the place? You never really told me" the boyfriend just asked, lying on the boat the same way he did 15 minutes ago when they took off.
"Oh, just a nice cottage on a island in the middle of the lake. Nobody is passing by usually, so we can have all the fun we want" Ivy once again said, making Owen smirk perversely.

And 2 minutes later, just as promised, the island in question popped up, Ivy quickly steered their boat towards the dock before ankering.
"Hey honey, can you bring our suitcases up while I secure the boat? You can also change ino your swim trunks, I will be with you shortly and then this vacation can really start~".
Owen did not need to be told twice, so he eagerly took their two suitcases and carried them up the stairs to the cottage that was sitting on top of a hill.
Afterward he immediately went inside and upstairs before starting to unpack the black suitcase.

What greeted him when he opened it was just a white one-piece bikini and all kinds of different outfits, underwear and bras, heels and multiple cases filled with make-up.
"Weird, I could have sworn that this was mine..." Owen mumbled as he heard the front door of the cottage, but quickly shook his head while taking the pink suitcase and opening it.
But instead of his clothes he was once again greeted by female articles of clothing, even though these were much less revealing looking.

At that moment Ivy entered the room, looking at her boyfriend with an unreadable expression.
"Hey honey" said boyfriend started, his eyes furrowed in confusion. "Did you make a mistake? Because I can't seem to find my stuff anywhere. Did you pack 2 for you and 1 for me?"
"Oh no, darling" Ivy spat. "I did not make a mistake. This is all yours" she said, pointing towards the black suitcase, which just confused Owen more and more.
But before he could say anything more his girlfriend rushed him, tackled him to the ground and used rope from the boat she hid behind her back to tie his hands and feet together.
"HEY! What do you think you are doing?!" Owen just screamed in shock, but was quickly shut up when she took some panties from the suitcase and stuffed them in his mouth.

"Shut up!" Ivy said, her tone cold, and her eyes just screaming for Owen to disobey.
"You think I did not notice? The messages? The calls? The fucking panties in OUR bedroom?! You think I would not notice all this, or that you SLEPT with that blonde bimbo?!"
This made Owen eyes go wide and his face go pale, after all he thought that he was sneaky with his infidelity, but apparently not as much as he thought.
"Thought so, you scumbag. And since you did not think I noticed you probably did not think what would happen now, did you?"
With that Ivy grabbed some scissors from her case and began to cut off Owen's clothes, placing the sharp object dangerously close to his crown jewels when he began to struggle.

Once all the clothes were gone she grabbed some waxing strips and began to apply them all over his body before ripping them off, making sure to go slow to make it as painful as possible.
When Owen was smooth like a babies butt she grabbed a small pink chastity cage and locked it on.
"The key to this is at home. I will now untie you. You will not struggle and you will not try to escape. Otherwise the key will get flushed down the toilet, alright?!" she warned, and Owen could only nod, fearing what would happen if he disobeyed.
With a satisfied grin Ivy loosened the knots, and once her boyfriend was free she grabbed some breast- and hipforms from her suitcase and glued them to his body.
Afterwards she grabbed a flesh-colored corset which she wrapped around his torso before starting to pull, going so far as to put her knee in his back to give Owen a nice hourglass figure.

Once Ivy was done with his shape she continued with the rest of the transformation.
First off was his outfit, which consisted of the white one-piece swimsuit from his suitcase, which she pulled up his legs and torso, leaving him with a look of frail femininity.
Next she grabbed a tube of glue from her stuff before she squirted copious amounts on it on her boyfriends bald head before attaching a blonde wig that reached to his upper back.
Afterward she started doing his make-up, beginning with foundation before moving on to the eyes, gluing on false lashes and adding some pale eyeshadow alongside some eyeliner.
This was followed by Ivy covering Owen's lips in lipplumper, making them big and puffy before she covered them in multiple layers of pink lipgloss, after which she painted his nails white.
She then finished his transformation by putting his hair into slight curls and adding a white flower hairclip before finishing Owen's outfit with a pair of white fuzzy 5-inch heels.

"So Evelyn, what do you say?" Ivy asked with a smirk as she pulled her boyfriend in front of a mirror, silently giggling at seeing Owen wince at his new name.
But when his mouth dropped in shock when he saw himself in the mirror, looking like a perfect girl, only the slight bulge from the cage giving anything away, Ivy could not hold herself back and burst out laughing, so loud much in fact that she slightly kneeled over and had to hold her sides.
"P-please honey, I will promise to never cheat on you again. Just please get me out of this" Owen pleaded, desperation in his voice as he knew he was at his girlfriends mercy.
"Oh, don't you honey me, you bastard" said girlfriend just hissed, not at all moved by his pleas.
"This is nothing compared to the humiliation and shame I felt when I found out you were cheating on me! And until you feel the same as I did you will not get out of this, understood?!"
Once again Owen winced, this time at the anger and coldness in his partner's voice, and he could only look at the ground and nod in submission.

"Good, glad you understand your position" Ivy then said with a grin, her mood doing a complete 180 as she basked in the power she had over Owen.
"Now I will go back to land to get some things, meanwhile you better tidy up the cottage. I should be gone for around an hour, and I want this to be shining when I come back, alright?"
With those instructions Ivy left the little island with the boat, leaving Owen alone to do as she commanded, vacuuming and mopping the floors, dusting all the surfaces, cleaning the bathroom and cleaning the grill that stood outside, each task made more difficult thanks to his heels.
He was just finished with cleaning the chairs and table that stood next to the dock when he saw his girlfriend's boat come, but much to his shock she was not alone.

"Hey, looking good sissy!" shouted Sarah, one of Ivy's friends, as the boat docked on the island and dozens of girls started to pour out, all pointing and laughing at Owen.
"She does, doesn't she?" Ivy just said with a smirk as she saw Owen turn red from the humiliation.
"And looks like she prepared everything for our vacation here! Good job Evelyn! Now be a dear and fetch me and my friends something to drink, alright? Something to cool off!"
With that Owen made his way back up to the cottage under the watchful eyes, snickers and laughs from the girls to do as he was told.
A few minutes later he returned to the dock, holding out a tray with glasses to the girls, with Ivy being the first to take one and taking a sip before immediately spitting it out.

"What is this?! I told you to get us something to cool off, not some watery piss without ice!" she shouted in mock anger, knowing that the ice cubes must have melted from the heat.
After all it takes about 8 minutes to take the stairs normally, and with how wobbly Owen was in his heels he probably took 3 times as long to get up and down the cottage.
"You go back up there immediately, and this time you will do it correctly, otherwise you can kiss seeing your little friend ever again goodbye!" she said, and with new fear Owen hurried up the stairs to once again make drinks for all the girls.

The next few hours passed like this, with the girls sunbathing, swimming or just chilling near the docks while making Owen fetch them everything they could need.
This ranged from getting them drinks, to getting them fresh towels, to making them some snacks, and after just two hours his calves burned like hell from walking up and down the stairs in heels.
This was until Ivy called him over to join the girls that were lying at the dock.

"Evelyn, will you come over for a bit?" Ivy asked, but instinctively Owen knew that he was commanded to do such, and with haste he made his way over.
"Evelyn, you have done a wonderful job so far, and me and the girls decided that you deserve a big reward for your obedience" Ivy said, and Owen hoped that he would finally be freed.
But much to his shock and horror this was not the case, as Sarah and Ivy took 2 large toys and strapped them to their waists while the other girls cheered loudly.
"Here is your big reward, Evelyn" Sarha said, making all the girls burst out laughing.
"And here, we got you something extra special! See those big things?" Sarah continued, pointing to the massive balls attached to the toys, drawing Owen's wide eyes to them.
"They are filled with fake-cum that shoots out when you please us enough!"

"And now here is the deal, sissy" Ivy said, taking over the conversation.
"You will be a good little bitch and go down on Sarha while I take you from behind, alright? And you will keep going until the whole liter of fake-cum has been shot deep inside you. After that I will think about letting you get out that outfit. Sounds

good, right?"
Owen could just nod, knowing there was no way to escape this, and with tears he got on his knees and bent forward to meet the toy attached to Sarah's waist before he could feel Ivy at his back.
What he did not know is that Ivy would only change his outfit to a maid one, which is more fitting for his position, and that the key "accidentally" went overboard during her second trip to the island.