Masked Freedom

There was a gathering of people out in a tropical retreat. The island was basically deserted other than some various huts and the building that was reserved for them. It was a special retreat for people seeking to start a new life and abandon their old way of life. Everyone new looked to be vacationing, while the 'workers' had pretty sexy tattoos and body paint, as well as peculiar masks.

The last boat of new arrivals showed up for the big celebration onboard Leo sat holding nothing but his suitcase and the brochure for the program. "Here we go I... I've heard good things at least" He sighed his near pixy blond hair blowing right into his eyes as the boat pulled onto the island. He was struggling with the weight of his suitcase before one of the masked men walked over, taking it with ease and moving it onto the luggage cart. Giving Leo a curt nod before walking away without a word.

He would soon see several masked women guiding people off the boat. "Come along, right this way. Your belongings will be taken to your rooms." One looks at him, while the mask did not betray her own emotions, her body did with how excited she got before running over to him. "LEO, it's so good to see you!" The woman hugged him tightly.

Leo wiggled around in the grasp of the woman, her bright red cloak covering too much of her body to give any real indication of who was beneath. "He... Hello!? D... Do I know you..." He blushed trying to pull back but only ending deeper in the woman's arms and fabric. "Like your voice is familiar but that's about it..."

"It's me, Fin!" The 'girl' giggled some more before pulling away. "It's been so long, I wasn't really expecting to see you here." She bounces happily before taking his hand and leading him off the dock. "So, what led you to coming here if you don't mind me asking Leo?"

Leo gulped looking over 'Fin'. "Well, I was having money and family issues... then my co-worker recommended this as an option. I won the 'free trip' my job offered and decided... I would probably be happy here and it was worth checking out." He sighed letting the girl drag him deeper into the island ahead of the normal group.

Fin's body as she shifted was looking amazing. Her ass was large and slappable, she had perky B cup breasts. Her waist added the perfect hourglass shape to her body as her butt swayed back and forth. "I'm happy, I promise that you will have a really nice time here. It really changed my life after...well my parents disagreed with what I wanted to do in life."

Leo sighed hugging Fin gently. "I was having a similar issue with mine. Apparently liking skirts is..." She looked over Fin. "Not ok ya know." He turned flushed as he looked deeper into Fin's clothes appearance. It was entirely blue with a large brown belt keeping it tight around his waist making the only distinguishing features of Fin his hair color and markings. "I'm hoping to have a good time. A new community is really just what I need these days."

Fin giggled and nodded "Everyone here is really accepting and will help you get to be exactly what you want to be as well." She reaches down and pinches Leo's butt. "Though I have to say, you have a wonderful ass already to go along with a super cute skirt."

Leo yelped slightly at the squeeze before looking deeper into the island. "So can you show me around here then... it is good to see you though Fin even if I can't really 'see' you. What is your role in the group anyway? I've heard that there are different groups in the community to help each end run smoothly."

Fin giggles and nods "Sure I can show you around. My job here is to help others come in and understand everything that we do here, as well as help new inductees acclimate to whatever changes they wish." She takes Leo's hand and starts to lead him further in. "While we have a hotel here, it is more like a specialized retreat, meant to have comfortable rooms for everyone who comes in before we can get you set up on the island. We have plenty of exercises as well as salons and other methods to destress."

"Well, that sounds nice... honestly, while I don't know exactly why I came... I just didn't wanna stay where I was." Leo looked in the distance seeing the large but seemingly comfortable facility near the edge of the island. "If you are a greeter what other roles are there? I assume some of you farm and help man the hotel but what about the rest of the group?" His voice was fairly weak feeling awkward asking so many questions so soon.

"Oh, we have fishermen, chemists, doctors, the works. We do all sorts of things here and are completely self-sufficient from the outside world. You name it and we most likely have it or something related to it." She shows him some land overlooking the farms that they have, as well as a variety of fruit trees. "When not greeting, I am a general helper, going wherever I am needed to provide relief for workers that need it."

Leo giggled a bit. "Well, that sounds about right for a kind-hearted dork like you." While looking over the farm Leo gave Fin a small hug. "I've never been the most... strong of people so I would probably wanna be a more supportive kinda person ya know?" He stood back looking into the pure white mask with black eye and mouth holes. "I still have no idea how you get that shadowy blackness behind the holes? Like is there a trick to that?"

Fin nods "You can do the same things I do! It is amazingly helpful to everyone. Also, there is a special magic trick to the masks, I'll show you later." Fin giggles and hugs Leo, nuzzling into his neck playfully. The smooth mask felt pretty nice, and Fin's body against his own, every little press and wiggle was oddly amazing.

Leo shuddered a bit before adjusting his legs to hide the bulge that had appeared in his skirt. "Thanks, Fin... that sounds really nice." he gently hugged Fin's side. "Also how are you so soft? Like the fabric and your pressure feels nice as hell. Is it your training that helped you learn this?"

Fin nods and claps eagerly. "Yuppers! I trained and went through a few procedures to get the body I wanted which helped me get soft. Then my work here has compounded on that and I am now super soft and loveable for everyone here!" She giggles and hugs Leo again before taking his hand. "Alright, let's go look at some more for you!"

"That's super cool Fin I can't argue that you look wonderful these days, but yeah let's go check out the resort. I need to go get my luggage anyway and find out where I'll be staying until I... make my decision about becoming part of the group." Leo smiled following Fin easily enjoying being around his old friend.

Fin takes him to the resort, showing that lots of people are being shown around by various masked members of the group. Fin saunters up to the desk and talks to the masked man behind the desk before getting a key with a number. "Right this way, you are in room 201, so we just need to go upstairs." She takes Leo's hand and heads towards the elevators.

Leo nodded hopping on the elevator with Fin hitting the button to get up a floor. "This place seems really nice... hey Fin... is there anything you like to be called now? I know I've been using your old name but clearly you're pretty different these days and I don't wanna be... rude."

Fin giggles a little "Oh I don't mind what you call me. I've gone by Fina, though my full name is Fiona now." She hugs to Leo's side playfully "So, I've noticed you seem pretty...interested in me to say the least over our short time being back together." She giggles a bit while hugging him before the door opens and she leads him briefly into the hall before handing him the key and motioning to the door.

Leo blushed, shaking his head before unlocking the door to the room. "Well, I have missed you. Your family wouldn't tell me where you ran off to and I got caught up in my own mess of life so I never was able to find you. That and I won't deny you look very cute in your new outfit." The interior of the room was about the same as a nice single bed hotel room with only the striking lack of a tv with a table containing all kinds of books and tabletop games looking around he also saw his luggage sitting on the bed.

Fina giggles and sits on a chair "Well...things got pretty...heated with my family. I mentioned how I wanted to kind of transition...they did not like it. During our screaming match, I was disowned and kicked to the streets without anything, and told I could come back when I got these 'silly ideas out of my head'. Well, I ended up meeting one of the members of this group and they helped me get away. I am sorry for not telling you...but I needed my family to not know anything about where I was."

"Well... I can't deny I've had those thoughts as well. I've always kinda pushed it down in hopes of it going away... that was a big reason for me to come out here, so I could finally be free from my fear of rejection. I didn't even tell anyone other than my employer that I was coming here... I don't know if I wanna ever go back." Leo looked down, taking Fina's hand and walking over to the bed before sitting down and hugging, into her side. "I mean I don't hate having some masc features but... being fem always just sounded so much nicer... and seeing you happy like this is making my stomach get all fuzzy again."

Fina giggles and hugs him before gently lifting her mask, showing her feminine face with some alluring tribal style face paint. "Why thank you, and I promise, it feels great to just...be yourself. That is the entire point of being here." She blushes a little bit "Being yourself...being loved for being yourself, and loving yourself." She looks at him and gently brushes his hair a little bit "I promise, if you chose to stay here, you can fully embrace what you want to be, Leo." She leans in and kisses his lips.

Leo was stiff as a board as their lips touched, unable to respond properly. After a moment of sitting in the kiss, he pulled back. "I... thank you, Fina. I really think it's what would be best for me." He looked down at his arms covered with a long-sleeved shirt he gently pulled the left sleeve up showing a few scars before looking back to Fina with tears in his eyes. "I... want it to stop hurting."

Fina gently rubbed his scars with a frown. "Leo, I promise, you won't feel like doing this ever again." She looked up into his face, a frown marring her features before she gave him a quick kiss and pulling her mask back on. The eye and mouth holes looked like they were letting light in...until it was over her face properly and resumed to be pure darkness. "Alright, is there anything you need to do before we go have a little fun?"

Leo shook his head a bit trying to block the tears from coming any further. "No there's nothing else I need." He pulled the sleeve back down before standing up and taking Fina's hand again. "Now you said we were gonna go have fun. I know there's still another day before the 'initiation' day where people can choose to stay or go so why don't we just... try to enjoy this time while we have it."

Fina giggles a little and hugs him "Sure, while we have plenty of ways to have fun and spend our time, I'll be right here the whole time for you. How would you like to have fun?" She rests her hand on his thigh gently, rubbing a little bit. "I promise, I'm ok with anything. We have a few shows we can watch. There are some movies. We can cuddle...or anything else that comes to mind."

Leo nodded looking out the window over towards the beach. "Wanna go out to the beach? I won't lie the only time I've ever even seen one was while I was getting on the ship so going on a walk there with you sounds... nice." While blushing furiously he leaned in kissing the mask's forehead. "Thank you for being my guide."

Fina giggled and nodded "You got it, there is plenty of space on the beach." She leads him out of the room, and eventually out to the beach. While others are enjoying it as well, some playing ball, others sunbathing. Fina gently leads him down the coast until they are alone. "Here we are, nice and quiet. We can just enjoy everything out here to ourselves."

Leo walked down to the very edge of the water letting it wash over his feet as he just took a breath and enjoyed the sounds of the sea. "Honestly for as annoying as lacking traction is. This is such a nice feeling just being away from everything. It's weird I know I came here because I wanted to leave everything behind... but it's just so surreal to think that I'll be leaving behind more than just my old life." He reached down, rubbing his arm gently. "At least I hope so."

She walks up behind him and rubs his arms a little "You will be embracing a new life. Where I'll be right there with you. You won't ever be alone again." She nuzzles into his back gently. "You already look extra cute, and we can try helping you in every way possible."

Leo deflated slightly in Fina's arms. "Thanks that really helps... honestly, I always thought people saying that a sunset on the beach is beautiful were overrating it but I don't know." He smiled at the gentle oranges reflecting from the water as the sun continued its descent for the evening. "I think I was wrong. It really is something special."

Fina gently smiles "What makes it more special is sharing it with those you love." She hugs him a little more before pulling away and turning him to look at her. "So, what would you like to do now? We can stay out here for a good while longer, or we can go and get you some food."

"I won't lie to you Fina I'm starving right now let's go grab a bite to eat." Leo's face was bright red as he looked at her before shaking it again to try to get himself back together. "Gods if you're not careful I'm gonna start thinking this is a date." He chuckled a bit trying to push the idea out of his head as they walked back towards the resort.

She giggles and holds his hand "And what if I kinda want to think of this as a date?" She looks back at him and giggles "I really care about you and have you back in my life, so I would really like to cement it with something special."

Leo visibly shuddered her hairs standing on end before calming back down. "W... Well if you want it to be a date then a date it will be!" His head felt like it was on fire, everything about Fina's behavior making Leo overwhelmed from all the affection. "I definitely wasn't opposed to the idea, and I'm happy to have you back in my life too. I never expected it but I will admit there's nothing else I would have asked for at this point."

Fina smiled under her mask and gently hugged Leo's arm. "Come on, the cooks make some wonderful poke bowls. We can enjoy a nice dinner then spend the rest of the night cuddling. It is nice and clear so we have the beautiful sky to enjoy."

Leo's stomach growled as they walked, the distance that they had gone from the resort making the walk back quite long. "I slept through lunch on the ship so this is my first meal of the day... that one is on me though." He chuckled enjoying the rest of the walk to the pool in the resort seeing the outdoor meal area and heading over to one of the tables near the edge. Enjoying the smell of meat, fish, and fruit mixing.

Fina quickly orders a pair of poke bowls along with a pair of pineapple drinks. "Here we are, I hope you enjoy it. If you don't I'll get you something else, Leo." She pulls him to a table where they can eat in peace.

Leo immediately digs in munching happily but still eating far faster than he should out of hunger. After a bit of shoveling food in his mouth, he takes a breath looking at Fina. "Sorry about that really got lost in my hunger for a second there." He giggled before sipping the pineapple juice curiously making a simi confused face before sipping it again. "It's true, this all does taste amazing."

Fina giggles, as food enters the black hole where her mouth is, it seems to enter the shadow and come out clean as she eats her own dish at a much more sedate pace. "I don't have this every day, but it is one of my favorites, and I wanted to share it with you."

"So how long have you been here? I know the last big invite was about half a year ago now." Leo enjoyed his drink while maintaining eye contact with Fina, despite her masked appearance, he was enthralled by his friend. "I know how you got here wasn't great so you don't have to talk about it if you don't wanna."

Fina thinks a little bit "I've been here a little longer than the last big invite. I would say about a year ago or so." She finishes her own meal and sips her drink. "I have been adapting and working for almost the whole time. Hormone treatment among other things really does affect you pretty hard at first, though I may be doing a little more down the line."

Leo nodded. "Well, that makes sense, speaking of hormones and such." He looked to the side, frowning but trying not to let his mood drop too much. "I would like to maybe definitely do it. I've looked into it a few times but you know how hard they make it back where we actually come from."

Fina nods "Well, we offer hormone treatment to any who want it. There also are a few more...extreme treatments as well...and one of those has been tempting for me admittingly." She looks down and looks nervous. "Though there is a part of me that has been a little nervous about it."

"Hey if you want to we can go up to my room and talk about it. I have a feeling talking about all this will help both of us get more of an idea on what we want for ourselves." Leo stood up and walked around, before starting to rub Fina's back gently.

Fina hugs Leo and leads him back to his room. "Thanks, anyway, let's start with you. You want to do some hormone treatments to embrace your femininity more?" She removes her mask, revealing her smiling face to him.

"Yeah, I really do. I don't really like any of my masculine features and having a mask to hide my face that makes me wanna puke every time I see it sounds pretty nice." Leo chuckled a bit leading her over to the bed and sitting down. "Even with the whole mask thing. I would still love to transition to the point where I don't feel like I have to hide my face to feel comfortable."

Fina smiles and kisses Leo "I promise, you will look even more beautiful than you do now." She rubs his chest lightly "You will have wonderful perky breasts, and your figure will work out great." She rubs down Leo's arms "I promise, you will learn to love yourself here."

Leo nodded gently before leaning back in to kiss Fina again. "I know I can now. I'll get there with your help as hopefully a new me. I've got a name on my mind but I'll wait for the ceremony to take that as my own." He rubbed down Fina's sides gently. "So what have you been considering?"

Fina blushed a little bit "Well...I've been talking with some of the others who have gotten it, but I am still nervous. I've...been kind of thinking about castration. I'm never going to use it and I don't really care to have..you know...children. There is just something so arousing yet intimidating about it."

Leo nodded, rubbing Fina's back gently. "That's understandable. Any time you make a big change in your life it can be intimidating hell that's why I was so nervous about coming out here." He leaned in and kissed her cheek. "But whatever you choose I'll support you all the way."

Fina nodded and blushed "Well...I've been...kind of thinking of getting fully castrated." She rubs her legs together embarrassed "I've got mixed feelings about it, but I've got more feelings kind of leaning into doing it honestly." She gulps and looks up into Leo's face.

"Well, you should go for it if it will make you happiest." Leo smiled before leaning in to kiss Fina's nose. "After all, like you said that's why we both came here. To embrace who we really are and even if you wanna raise a kid eventually an adoption is always an option."