Interesting Summer Vacation Part 5

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Interesting Summer Vacation Part 5

By: Kokopo618

"Lily? Hellooo?" Katie said, waving her hand in front of my face.

I stood motionless, like a deer in headlights or a doe, I guess, I had no idea what to do, but I had to say something, "I am um, I'm...uh...I..." Well, I tried.

"Don't worry, I'll let you finish, just clean up afterward, okay?"

"I...uh..I, okay," I say, finally. Katie leaves, closing the door behind her. I am left with my hand still up my privates, more confused than I've ever been. I remove my hand and aggressively wash them off in the sink. I feel disgusted and more than a little ashamed. I pull my panties up my legs slowly, trying to avoid any more arousal, it backfires, It feels amazing sliding my panties up my smooth legs, I guess my "do everything slowly" rule does not always apply. I pull them up all the way without getting too wet. I grab my shorts and pull them up too, once again necessitating a slight ass shake to get them over my butt. I change out of the red sweater and back into my tank top. I start to leave but I stop, catching my image in the mirror, and put my hand down my pants, I feel for my clit outside my panties, dare I finish?

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No I quickly decide, I can't. I leave, dreading my inevitable interaction with Katie.

Once I leave the bathroom I consider leaving the cabin, but I know I'll have to face Katie sooner or later. I open the door to our room, Katie is back to going through her clothes, she doesn't say anything to me, so I walk over to our closet and hang the sweater back up, I sit on my bed, thinking of an explanation.

"So did you finish," Katie asks, with her back turned to me, so I can't tell her emotion.

I take a breath, "No, and I wasn't even, I was just stretching, and my hand slipped," I lie.

"You are a terrible liar," Katie tells me accurately. "Plus, I heard you moaning."

"Oh, you did?" I reply, defeated, I lower my head in shame, "I'm sorry, I couldn't help myself."

"It's nothing to be ashamed of, Lily, everyone does it, it's very natural," Katie says, turning on her bed to me.

"You don't have to call me Lily in private," I say, trying to ignore the rest of what she said.

"Really, because I can't see a Will, playing with his pussy, moaning in pleasure," Katie says.

That's fair I think, "That's not fair," I protest.

Katie ignores me, "So what were you thinking of, sis," Katie says, smiling.

"Gross Katie, I wasn't thinking of anyone," I say.

"It's just us sisters here, Lily, you can talk to me, and I said what not who, so who was it, Bob?" Katie says, smiling wider at the end.

"No!" I was thinking of him, I guess, but not in that way, "I'm not gay."

"I never said you were, sis, and I get it, Bobby is cute, a little young for me, but he's tall and muscular, and-"

"Katie, please stop." I plead.

She leans over and grabs my hand, "I'm sorry, I went too far, I know this is weird for you, but it really is natural and I want you to know you can always talk to me."

"I know, it's okay, I know this is weird for you too," I say.

Katie looks down at our entwined hands, "You washed your hands right?"

I can't help but let out a little laugh, "Yes, I did." I say, blushing.

She pulls her hand away, "Good, I put your pills on the dresser, remember to take one of each morning."

"Okay, and just so you know, just because I'm dressed like a girl that doesn't mean I like boys now."

"I know, I was just kidding, So what are you gonna do about that girl who knows about you."

"I almost forgot, I should go find her now, gotta deal with it sooner or later," I say.

"I like this new go getting attitude, you go, girl," Katie says, giggling, turning back to her clothes.

"Sure, see ya," I say, leaving the room.

I go to the bathroom to check if I'm okay to go out, I run my hands through my hair and fix it so it looks better, when I'm happy with it, I leave the bathroom and the cabin. I run into Dad getting out of the car.

"Hey, Dad," I say.

"Hey, kiddo, where you heading off to?" He gives me a weird look, I wonder which one of us will get used to my appearance first.

"Ask Katie," I say, not wanting to go through the story with him.

"Okay...and I just wanna make sure you're still okay with...this?" He asks, uncomfortably.

"I'll survive, ...honestly I'm a little surprised you are okay with it," I tell him.

"Well, to me, you are who you are no matter what you wear, and you're just playing a character, right?" He asks.

"Right," I say quickly.

"And plus, I used to know someone who..." He begins

"Someone who what?" I ask when he stops.

"Ask me later, now go have fun and be safe." He goes into the cabin, not giving me a chance to respond.

That was kinda weird, but whatever, more important things to do. I look over to the dock I see a few kids fishing off one side of the dock, and some guy cleaning off a boat on the other side, but I don't see Judy anywhere. I walk behind our cabin to the right of the dock is a little beach, with a number of little kids, and their parents playing in the shallow water, and I see Judy swinging on a swing set just off the beach. I start walking towards her, wondering what I should tell her, lying does not seem to be my strong suit, so the truth might have to do, I'll probably let her do the talking and answer the questions as they come. As I near her she gets up turns in my direction and starts walking. When she sees me a smile comes to her face, she waves, picks up her pace and walks over.

"Hey Will, I'm glad you're here, I'm going to the dock, come with me." She says, beginning to walk in the dock's direction, I follow.

"Uh..okay, but," I swallow, "It's Lily, now," I say, trying to be self-confident.

"Good for you, it's better than Wilma, at least, but I think I would have gone with Willow or Stacy, maybe."

"It's just a random name I thought of and I think it's close enough to my real name that I won't forget it," I say.

"It really suits, a blonde babe such as yourself." she says, smiling at me.

"Are you sure you don't mean a delicate flower," I say, giggling.

"That, too" she agrees, Laughing back.

I could continue to be offended by girly compliments, but whatever, the plan was to "go with it" so might as well go all the way. We make our way to the dock and sit down between the two kids and the guy cleaning one of the boats. We dangle our feet above the water, my legs are longer than hers, but I don't reach the water.

"So," Judy begins, after a while, "why are you doing all..this, are you transgendered or something?"

I don't really know what that word means, I watch the news, so my rough understanding is that it's a person who was born in the wrong body, gender wise, and wants to be the other gender, "No, this is all a mistake," I sigh, I guess the full story it is then, "Well, it all began when my Dad got this vacation for free, because he knew the owner, and other reasons, so we drove up here, and about half way, it was revealed that there was some sort of mistake and my gender was wrong, so we decided it was best that we just go with it." I take a deep breath, Judy is listening intently, "So we drive to a nearby mall, and pick up these fake breast things, some other things, and this outfit for me." I leave out some things, like my vagina, but she doesn't really need to now that.

"Wow." she says, simply

"Yeah, I know," I say, grinning, it kinda feels good telling someone.

"Wow," she says again, trying to process, "So you...Wow."

"Yup, It's been an adventure," I say.

"Well, you look great, like really great." she says, something I saw coming.

"Thank you," I say genuinely, "I picked out the outfit myself, do you like it?" I ask. I know Katie seemed to like it, but I prefer an outside source.

Judy seems a little surprised by my reaction and question, "Yeah, I do, a lot, very pretty"

"Aw, you're so sweet, thank you," I say back, meaning it, I know how I sound, but I try not to care. We talk for a while, about dumb stuff, nothing important, sometimes about me, sometimes about her, I haven't had a friend in a while, a long while, and it feels good to talk to someone. She is noticeably a little uncomfortable at first, but as we talk longer, she gets more comfortable and talks to me like she would any other friend, well, any other girl friend, but still. We giggle, we laugh, I answer a ton of her questions, and I realize I'm having the most fun I've had in years, and I have boobs, my life is so fucked up, I kinda like it.

"So I've answered all your questions, don't I get some to ask of my own?" I ask.

"Sure," She replies, "I'm an open book, but that book is written with invisible ink." she laughs, at her own dumb joke, I laugh with her.

"Okay, so you recognized me immediately, even with all this on, and you said it was because you are observant, but I don't believe you, why is it really?"

"I was nervous that you'd ask me that," she sighs, "well I saw you in the hallways at school, and I always thought you were different, interesting even, in a way I could never pin down, so whenever we had class together or I saw you in the hallway I ended up staring, and I never knew why until I realized..." She sighs again and puts her head down, "you're gonna think I'm so dumb, especially now."

"I promise I won't." I couldn't really promise that. I never noticed her staring before, I never knew anyone paid that much attention to me. I wish she would have talked to me more, we could've become friends.

"Okay, I believe you, It's just very hard to say out loud, to you, um...I had a major crush on you." She finally says, her body seemingly shrinking in shame.

"Oh, oh, oh." Well, I was not expecting that. Wow. I can't help but smile a little, I've never felt desired before, and it feels good. I don't know what to say, but I know I should say something.

"Not anymore, obviously," she clarifies, quickly, clearly embarrassed, "It was freshman year, I know that's this year, but, you know, I was-"

"It's okay, Judy, really, I'm just surprised is all, I never had any idea, why didn't you ever, Ya know, pursue me?"

"Oh, I don't know, too shy, I guess?" She says.

I can hear footsteps coming in our direction from the right, they stop when they get right behind us, "Sorry to interrupt you, ladies," Bob says.

I turn my head and look up, there is Bob, he looks much taller from sitting position, "Hey Bobby," I say, smiling.

"Hi Lily, He says, looking at me, then at Judy, "Hi Judy," He looks back at me, "I just finished cleaning and prepping your boat, so you can tell your Dad it's ready, It's the big one, over there," He says, pointing, "It's a Pontoon, may not be the fastest, but it's the biggest, most comfortable, and pretty good for fishing."

"Thank you so much, I can't wait," I say, looking up at him.

He starts to walk away, but turns back to us, "Oh, and if the offer is still on the table, I'm mostly free tomorrow, and I'd love to go out fishing with you guys in the morning."

"Sounds like fun," I say, genuinely, I don't really know how to fish, so it'll be nice having someone who does, in addition to Dad.

"Cool, just find me in the morning when ever you're ready, goodnight girls."

"Goodnight Bobby," I say as he walks away. My eyes linger on him, but I look back at Judy, after a second.

Once he's out of earshot, "You asked him to go fishing with you?" Judy asks, almost accusatory.

"No, my Dad did, what the big deal?"

"Nothing, never mind," She says.

"So," I begin, wanting to change the subject, "maybe after all this is over, and we are back home, we could go out sometime?" I ask. I've never asked out a girl before, fear of rejection and all that, but this seems like as sure as a sure thing can get.

"Uh, sorry Lily, but I'm not a lesbian," She begins, she laughs nervously, then unsure of whether to continue, "and I'm not sure you are either..."

"What does that mean?" I ask, unsure of whether or not to be offended.

"Well, just the way you were looking at Bob just now." She says, "It just reminded me of how I've seen some girls look at cute boys."

"I was not looking at him in any such way," I say, at least I don't think I was, It kinda just happened, I was on auto-pilot.

"You called him Bobby." She says.

"No, I did not," I say. I would not say that.

"Twice."

"I don't think I did, and even if I did, It's just Katie getting in my head, she called him that."

"Sure, but you also gave him a great view of your boobs, looking up like you did."

"I just got these," I say, groping myself, "I don't know how to avoid that." I didn't even realize I was doing that.

"Okay, whatever you say," Judy says, giving up.

"I'm serious," I say, maybe a tad too defensively, "He's is just some boy, just some dumb boy," She gives me a funny look, "Oh god, what did I do this time?"

"Well, the way you said that, I don't think boys call other boys boys, and I really don't think boys call boys dumb boys." She says.

I take a second to try to understand, "I've never heard of that rule, but fine whatever, he's just some guy." she gives me another look.

"See, even when you say that you sound like a girl denying that she likes a boy."

"I'm done, I can't win today."

"Sorry." She says, and I can tell she means it.

"I don't blame you, I know I sound a little girly...okay a lot girly, but this is all so new to me, maybe I like being looked at for once, even if it's a guy."

"Well, looking like the way you do, you better get used to attention from guys and hope they are as nice as Bob."

"Thank you not telling anyone about my...thing," I look around, it's gotten dark since we came out here, the kids that were fishing are gone, "We better return to our families, It was really great talking, I hope we can do it again."

"Anytime, Lily, it was great meeting you." We get up and hug, although I'm taller, I can feel our boobs touch, I'm surprised I don't get aroused. The hug is warm, just two girl friends hugging. We separate and walk back to shore, we walk to my cabin, say our goodbyes. Judy continues, I make note of where her cabin is, just up the road from mine. I can hear faint talking from the inside of my cabin. I walk in, Katie and Dad are playing cards at the Table.

"How'd that go," Dad asks, as I enter.

"Good, really good actually, she's not gonna tell anyone and I think I made a friend."

"That's great," Katie says, "we were just going to head outside, and sit for a while before bed if you'd care to join us."

"Sure," I say. Katie stands up and walks out, Dad follows her, then stops

"Grab something to eat, I'm sure you're hungry." He says, before walking out.

I look around, see a bunch of bananas, grab one, and walk out. Katie and Dad are sitting in lawn chairs, already talking. I find a chair and sit down behind them, I take my time peeling my banana, it's not too ripe, just how I like it. I notice the two kids that were fishing off the dock earlier, are sitting on their cabin's porch, it's just opposite of us. They look like 12-year-old twin boys, but I'm terrible at guessing ages. One punches the other and points in my direction, I look behind me and see nothing of interest. it takes me a while, but I realize they see my banana and are waiting for me to eat it. I used to avoid bananas at school because of the obvious dick sucking jokes that would ensue. I'm too tired to care, I might as well have some fun with them I decide. I fully peel the banana and bring it to my mouth, making sure Katie and Dad are not looking. I give it a long lick along the "shaft", then and put as much as I can down my throat, and take it out, I lick and suck the banana for a while, they are really enjoying my show, but I'm getting tired, and don't wanna appear like too much of a crazy person. I take a bite. I feel a tap on my shoulder, I turn and Katie is there smiling down at me. I've been caught, again, she must have got up and I didn't even notice, I was too into it, how long has she been watching. She gives me a motion telling me to follow her inside, she walks in, I get up to follow. It really is just one thing after the other today, well, that's what makes life interesting.

Author's Note: Hey everyone, I apologize this was supposed to be released yesterday, but stuff happened so here it is now. It's pretty crazy this is still day one, right? By the way, writing this I realized I named the main character Will Smith, like the actor, if you noticed that, congrats, It was not intentional, I'm dumb. One of the worst things is reading a story you enjoy, and suddenly without warning its stops and the author moves onto something else or just quits entirely, so I want you to know I will not stop until I'm done, you have my word. So, as always, feel free to comment any questions, concerns, plot holes, and plot points you'd like to see, I'll always respond. Thank you so much for reading, and sticking with my crazy story. THANKS BYE!!!

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Comments

From what Judy has said

From what Judy has said regarding Lily's actions and comments, and now Lily's interaction with her banana, I do believe that Miss Lily has a lot more female in her than she is willing to admit too, or does not believe just yet.
I'm still of the belief that this is a set-up by her sister and dad, because they both figured her out earlier and want to confirm their own views of the "sister and daughter".

I love the theory.

kokopo618's picture

The theory is great because depending on whether you believe it or not, it changes how you view every interaction between Lily and Katie/Dad, very interesting stuff. Thanks for reading and commenting.

(Deep introspective quote that makes you think)

Agree completely!

My5InchFMHeels's picture

I got the same feeling about a setup, I mean what dad is likely to think it's a better idea just to go with it when the resort owner is a friend... I'd think he'd be quick to fix the wardrobe and why only pack "just in case" for the sister?

It is still enjoyable, Lily does have bad timing too apparently.

Thanks for reading!!!!!!!!

kokopo618's picture

She finds it very intoxicating, it hasn't even started yet.

(Deep introspective quote that makes you think)

:-)

:-)

Judy in the hallway

Jamie Lee's picture

For Judy to have known Lily was Will, she has to be super vigilant at school. Will has to have some feature, some mannerism which transfers to Lily without trying. Maybe his facial structure, his ears, something Judy noticed about his upper body, since she recognized him before he got out of the car?

But something else is going on with Will, unknown to him, her. Even after he explained why he's dressed as a girl, Judy still believes he will continue presenting as a girl after the weekend. Why else would she turn down his offer of a date after they get back to school? And then the pills Katie has him taking, to make his dressing as a girl more presentable. For a weekend? Might those pills be blockers or what he needs to gain a complete female figure?

There hasn't been said of any dead fish floating in the lake, but something does smell fishy.

Others have feelings too.