Interesting Summer Vacation Part 2

By: kokopo618

"Will get down here I need your help." I was already half awake so my dad's call didn't startle me too much, but I still rushed down stairs. It was already Saturday morning, the day of our trip, the week flew by.

"What do you need Dad," I ask groggily.

"I need you to take this suitcase out to the car," He says, dropping a large suitcase in front of me.

"I thought the resort provided all the clothing?" I ask.

"It does, but the owner sees this as us doing him a favor so we can keep all the clothes we want, it's mostly for your sister."

"Got It," I say bending over to lift the suitcase. I look for the handle, find it and try to lift and my heart breaks just a little when something I should have expected happens, I can't lift it, I get a better grip and still, nothing.

"Katie come help your brother," Dad yells. I can almost taste the disappointment in the air.

"Sorry can't, I'm in the bathroom," she yells back, I know she is sincere, she knows how much I hate disappointing him.

"Don't worry Dad, I got this," I say feigning confidence. I try dragging it and I still can't move it.

Dad sighs loudly, "Here let me help," He bends over to lift the one side of the suitcase while I hold the other. It is obvious that he is doing all the work. We slowly walk in silence until about half there he repeats something he's said before.

"I know you don't like hearing this son, but you need to start lifting weights or doing some push ups."

"I know dad, I'll try," I say sadly. I hate disappointing him.

We reach the car and put the suitcase in. Dad tells me that we are all set and to go back in the house and wait for Katie. I go back, Katie's still in the bathroom so I sit with my head hung low and wait. Katie comes into the doorway, I get up and tell her we need to go, she tells me to sit back down. I sit down with my head down holding back tears. she sits next to me and begins rubbing my back slowly.

"I heard everything, I'm sorry, I know you hate disappointing him."

I don't say anything for a while,"I wish I was someone else," I whisper through the tears.

"What?" She says, caught off guard.

"I wish I was someone else," I repeat louder the sadness in my voice palpable, "Anyone else, being me is not working out and hasn't for a long time."

"Everything will be fine," she runs her hand through my long blonde hair, "Everyone feels the way you do at one point or another. I sure did, It will pass." She gently lifts up my head and looks at me in the eyes smiling, "look, we are going on a free vacation, we are going to have a great motherfucking time and we are going to turn that frowny upside Robert downy....jr."

I can't help but laugh at her silliness, I just hope she's right.

"Now, wipe off those manly tears and meet us in the car." She says running off.

I wipe off my tears and head to the car. I notice Katie has opted to sit in the back with me and she is already smiling ear to ear and dancing in her seat, all the moral support I'll ever need.

"Okay buckle up kids, It's gonna be a long ride."

The ride is long and boring as soon as I start to get hungry and in better spirits we stop at a dinner in a small town. We sit at a booth and almost immediately an short rotund old lady in her mid to late 60s appears as our waitress.

"What will y'all have to drink this morning," She says with an inexplicable southern accent.

"Coffee, black," Dad says evenly.

"I'll have a coke or Pepsi, whichever you have will be fine, thanks," Katie says gleefully.

"And for you young lady?" The waitress asks, unfortunately referring to me.

Katie puts her hand on my knee in solidarity. This happens a lot when I meet new people I've come to accept it in a way, but no matter how many times it happens I never know how to deal with it. Correcting her would only lead to her embarrassment and mine. My dad being here also complicates things.

"Uh..he's a boy," My dad says, breaking the short silence.

"Oh..oh I am so so sorry I am very old as you can see, my eyes don't work as well as they used to, and.."

"It's okay," I interrupt weakly, "I'll just have a water."

"Right away," she waddles, off embarrassed.

It was nice of her to pretend it was her fault. Not that it's my fault either, I can't help how I look. We order our food and eat in silence.

"That would happen less if you cut your hair, you know," Dad said knowing full well I knew.

"I know dad, I like my hair."

We pay and walk out to our car, we get in and before starting it, he pulls out his phone and checks it for a minute after a while of reading and rereading the same text he say, "huh, weird."

After it becomes clear he's not going to expand upon whatever he's talking about Katie says, "What's weird."

"I just got a text from Carl the owner of the lodge he says our cabin is ready and he is excited to welcome my daughters to his resort."

"Wow twice in one day that might be a record." I say trying to bring some much needed levity, it doesn't take.

"That's not it, I haven't shown him any pictures and when we were on the phone I only told him I had two kids he seemed busy I didn't want to hold him up, besides most of this message seem automated."

"Automated?" I think out loud, "Didn't you say you had to enter our information into the computer."

"Yeah, so?" dad says.

"Can you check that information right now?" Katie says, catching on.

"Yeah sure," Dad opens up the resort's website and goes to his profile and sure enough, it reads Cabin Occupants: Male: 53, Female: 21, and Female: 16. "No no this is a mistake, I swear I entered you as a male, this is impossible."

"It's okay," I declare, despite all evidence leading to the contrary. "Whatever happened, happened, now we just have to deal with it."

"Well," Dad says, composing himself, "We can't go home, we are more than half way there, plus this is also a favor for Carl, we can't back out, and we can't ask them to replace your clothes, they are far too busy and they might not have the money or supplies."

We are all silent for a moment, "What if we go with it," Katie says quietly.

"What do you mean go with it?" I ask, fearing I know the answer.

"You know, go with it," say repeats picking up volume and pace, "The next town over is big enough so it has a mall, we could get you an outfit and.."

"Uh dad?" I say looking for help.

"Sometimes you have to take one for the team son, and right now It's just about our only viable option. It could work even in boy's clothing people mistake you for a girl."

Realizing this has a chance of happening I lose what little composure I had, "No no no no no viable? no no what? no no no absolutely no, no!"

I know I can't expect you to be willing to do this, so I'll tell you what, we go to the next town over Katie gets you an outfit, we'll see what you think, if you're not comfortable, we'll go back home no harm done, but you have to promise to keep an open mind, deal?"

"No one at the resort knows I'm a boy?" I asked meekly.

"No one. And no one ever will." Dad answers confidently.

"Okay, I'm promise."

Katie bursts out in joy "You will not regret this little sis, this is going to be so much fun, you're going to look so cute."

"Okay, to the mall." Dad says, starting the car.

I regret this, I think to myself as we pull out.

Half of an hour later of Katie going on about how cute I'll be, we pull into the mall parking lot.

"Okay, so the plan is, Katie you take Will and get him...situated, I'll get something to eat and wander around and we meet back here in an hour."

"Oh dad, please, you know us girls and our shopping make it two." Katie said giggling, looking down at me. I groaned.

"Fair enough, good luck you two, and Will It's very brave what you're doing, I'm proud of you."

It has been a while since he has said anything like that I forgot how good it feels, my happiness is interrupted by Katie grabbing my hand and dragging me in the mall, "Come on girl let's get our shop on!" she yells a bit too loud.

"Where to first Will?" Katie asks after we enter the mall.

"I don't know, you're the girl."

Katie ignores me, obviously in deep thought, "I wonder if they have...or if the sell..and if still..."

"Uh Katie, hello? I'm gonna need you to use full sentences from here on out."

"Yeah sorry, uh I'm gonna go find a store, you wait right here I'll be back soon."

"Okay" I say after she had already run off.

She comes back about ten minutes later, with a bag that reads "Big Richard's Big Richards Emporium" on the side."

"Whats that from," I ask.

"Uh..Big Richard's Big Richard Emporium ...duh." she tells me.

"You're not going to tell me what that is are you?"

"No, not yet. Now we need some clothes" She says changing the subject.

We walk around the mall passing by many clothing stores and not stopping at one. "What are we doing?" I ask impatiently.

"Well, it has been a while since I've been a teenage girl so I don't know what stores and clothes are in or out."

"You know the resort provides all the clothes right? when only need one outfit"

"Yeah, but if we're gonna do this we might as well do it right," she says, "Which is why we've been following those two girls around."

She points out two pretty teenage girls around my age "You are insane." I tell her.

"I Know, Look they're heading into the Gorp™ let's go"

We enter the Gorp™ and it's a teenage girl's dream more clothes than you'll ever need, hair stuff, nail stuff, panties, bras, and a lot of things I am not familiar with. I quickly become very embarrassed and nervous once I realize where I am. I'm following Katie around skittishly while she picks up some clothes and I feel like I don't belong.

Katie notices my discomfort, "Why don't you wait in the changing room honey, I'll be there in a second."

Once I'm in the changing room, I pace back and forth quickly, I close my eyes and breathe deeply trying to avoid a panic attack. I've gathered myself by the time Katie comes into the room. She is still carrying the Big Richard's Emporium bag and a large pile of clothing, more than I need.

"I wanted to give you some options." she says reading my mind.

I grab a bra from the pile, "this seems big are we gonna stuff it with socks?"

No, we are gonna use these, she reaches into the Big Richard's bag and pulls out prosthetic breasts, a Prosthetic vagina, and two containers of pills.

"Wow," I say flabbergasted.

"I know, I know, but you can't stuff your bra for a week without people noticing, especially other girls, and female clothing requires some boobage plus a flat chested female looks different than a boobless boy."

What she was saying made sense, and I trust her, "Okay, how do they work?"

"They are actually very advance, they turn off nerve connections on your chest and replace them with electronic ones on the boob, I'll I have to do is gently press them on your chest for a minute or two and when they attach you'll be able to feel through them like the real deal."

"Okay what do I have to do?"

"Take your shirt off and stand there and look pretty." She says giggling, causing me to giggle back. What a weird day.

I took off my shirt and Katie picked up the breasts and gently pressed them to my chest, and I learned a minute or two can feel like an entirety when your sister is pushing fake boobs on your chest. All of a sudden I could feel Katie's hands on my chest I thought the boobs had fallen off so I looked down to see two rather large perky breasts fully attach to my chest. Surprised and more than a little scared I stumbled backwards and with each step the boobs... my boobs jiggled along the way. Once I calmed down a bit I started poking them Katie was right, I could feel them, I noticed the my.. the nipples were fully erect.

"Why are the nipples so hard." I ask Katie.

"It must be cold in here," she explains, "here put this on." She hands me a red frilly bra. I hold it up and try to put it on for a while, until I have to admit I don't know how to.

"That's okay sweety," she says as I hand her the bra. She walks up behind me and puts it on me backwards, "I had trouble with these bastards when I started wearing them too, all you have to do is put them on backward like this, hook them up like this, spin it around, and put the straps over your shoulders like this and you're done, now you do it." She takes it off and hands it back to me. I put it on backwards, I hook it, I spin it around, and I put the straps on my shoulders.

"Good job," Katie says, clapping, "you're a natural, you are already better than I was at your age."

"Thank you," I say not knowing how proud I should be of my supposed talent.

"So how does it feel?" Katie asks.

"Well," I say thinking about how my life lead up to this point, "It provides support, my back already started to hurt from the extra weight, and um.." I look over to the mirror and see a cute teen girl with shoulder length blonde hair, and big boobs in a sexy red frilly bra," um.. they look pretty." I say without thinking.

"Don't sell yourself short sis you are already beautiful and we're not even done yet."

"Thanks" I say blushing with embarrassment, again questioning the complement.

"I also got you some blonde hair extensions by the way, you ready?."

"lets do it."

The hair extensions work real well, they feel like real hair, and flow with my natural hair nicely. I wish they took longer to put on as I am dreading the next part.

"Okay," Katie says,"let put on your Va-JJ."

"Um, can I do this one by myself?"

"Nope, sorry it requires another person." Katie says apologetically, "Close you eyes and take a deep breath everything will be all right."

I inhale then exhale then inhale then exhale. I'm starting to calm down, when with my eyes still closed Katie leans over and pulls my pants and underwear down.

"what the hell," I yell whisper, covering my crotch with a hand. There isn't much to cover. I've always had a small member, I'm pretty ashamed of it Katie hasn't seen my penis since I was a baby, and I don't want her to think any less of my manliness than she already does.

"Sorry but it had to happen one way or another." She says, "Now move your hand so I can put this on."

I move my hand, she get on her knees, she sees my one inch wonder, she doesn't say anything not that I expected her to, she then pushes the prosthetic pussy into my crotch and holds it. I thought the boob application was awkward, but this is on a whole other level. "I'm uncomfortable," I say, feeling my dick and balls being contorted into an unnatural position

"I know, me too," she replies.

"How will I pee?" I ask, perhaps too late.

"If I'm applying this correctly you'll pee out your dick and though the opening, like a normal girl, more or less, you'll see, It'll all be very natural.

"What if I get a boner?" I ask meekly.

"Just like your tits this will switch your nerve connections, It won't allow you to get boners, but it will cause you to pre-cum at an increased rate simulating a girls pussy getting wet."

"There are not my tits," I correct her. She doesn't say anything, "I won't get a period or anything, right?"

"No, I'm a little jealous, you get all the positives and none of the negatives."

"Lucky me," I say sarcastically.

Once again without warning I can feel Katie touching my..uh the prosthetic "it's on, it's on, it's on." I yell. Katie takes her hands away quickly. I cover up my crotch with my hands again instinctively.

"Here," Katie says as she hands me panties that match my bra.

I grab them, with one hand still over my crotch and look them over, "Is this it?" I ask only half joking.

"Nope, panties are just that small, well the good ones anyway." Sensing my discomfort Katie continues, "Why don't I wait outside and you figure out what you want and you'll wear it out, don't hesitate to ask for help, I'll be right outside. Good luck cutie." She leaves.

Oh boy, I think to myself, what have I gotten myself into. I lift one leg and stick my dainty foot in one of the small holes in the panties I pull them up sightly then lift my other leg and insert it, I slowly slide the panties up my skinny legs I am met with a little resistance from my wide hips and thighs, the feeling is euphoric and I am sad when I reach my crotch and the feeling is over. I check myself out in the mirror, wow this thing really stretched out. It goes about halfway down my ass cheeks and a little in the crack. I never noticed how big and firm my butt was, the panties make it look very good. They make my crotch look very clean as well, I rub my hand on the front of them and I can't feel any bumps. I also notice a cute little bow on my bra. My long flowing blonde hair adds to the image of a gorgeous teen girl. "I can't believe this is me," I say to myself quietly.

I snap out of my daze, I can't waste any more time, I might as well dig through the clothes. I notice the shirts the girls we followed in here were wearing, but in a different colors. There are some loose shirts, some tight shirts, some leggings, some jeans, some shorts, some really short shorts, and more sets of Bras and panties. the bra and panties I'm wearing now are good enough I decide. I don't want to wear anything too girly, but there is not much choice in this pile of clothes. I pull out a pair of jeans and a loose pink shirt tank top thing. The jeans are really form fitting and I struggle to pull them all the way up, my boobs jiggling all the way through, when I finally pulled them over my ass they fit pretty nicely and made my butt look even better. I giggled to myself, then cursed at myself for being so damn girly. The shirt was much easier I just pulled it over my head it was loose around my tummy and waist, but tight around my chest and it showed off plenty of my fake cleavage. I modeled myself in the mirror for a while and then I called Katie in.

"Yeah are you oka-," Katie puts her hand to her mouth. I got scared did I do something wrong? "oh my god, you're gorgeous"

Relieved, I ask, "Really? I look okay?" twirling around.

"You look amazing Will, great choice too, that outfit is perfect for you."

Hearing her call me Will was a little jarring, I did not feel like a Will right now. "Thank you, I don't really know what I'm doing though," I admitted, "So should we return the other clothes?"

"Hang on a second," She said reaching for her phone, after a second she continued, "I'm sorry, but I gonna be too hot out today for jeans, you'll be miserable."

"Oh okay I'll find something else to wear." I say, like it's no problem, truthfully I'm a little sad don't get me wrong, I'd much rather be wearing boy's clothing but I liked how this felt and looked on me. I turn around back to the pile of clothes and bend over to pick up new ones.

"Oh, and sis," Katie said with only her head peeking through the door, "Nice ass." she closes the door giggling.

I giggle. I have got to be more mindful I just gave her a great show just by bending over.

I pull down my jeans they are not as difficult going down as they are up, my boobs and butt jiggle nonetheless. I pull off my shirt thing and I'm back in my underwear. I bend over and pick up a simple white tank top. I pull it over my head, I have a bit of trouble get it over my boobs. It's much tighter than the pink shirt but it reaches all the way down to my waist, it also helps my bra support my fake ample bosom making the boobs appear larger. I adjust it in a few places and once I decide it looks good I reach back down and grab white shorts, I'm not sure they are shorts at first because they are so small, but Katie said It would be hot out today so at least I'll be comfortable. I slide the miniature shorts up my legs, again my butt gives me some trouble, but I get them on and button them up, they feel great and I look great in them, but I'm not sure how to feel about that. My thinking is interrupted when I notice how shapely my legs are, my ass and upper thighs are huge, but just before my knee my legs get skinnier leading all the way down to my dainty feet.

"You can come in now." I say to Katie.

I look myself over once more to see if I look okay. Katie comes in.

"Will, oh my god, you look amazing, perfect outfit." she says barely able to contain herself, "Are you comfortable?"

Hearing my name again was hard on me, "As comfortable as I can be in all.. this," I lie, truthfully I'm more comfortable than ever, besides in my boy clothes, of course, but I don't want to sound too excited.

"Well good, you look great, I brought you some shoes, thankfully they will go great with your outfit." she handed me a pair of small white tennis shoes and white socks, "I had to guess your size in women's shoes so tell me if they fit."

I grab the shoes and socks and sit down on the bench. Katie sits down next to me staring in awe as I bring up my shapely legs, one at a time putting on the socks and shoes. "They fit perfect, thanks sis."

"No problem, you did most of the work picking out your outfit."

I really liked that she called it my outfit, it felt like I created beautiful. I noticed myself in the mirror again and saw myself smiling wide, I toned it down a little, not wanting to appear so happy about my situation. then my eyes drifted to the two pill bottles Katie bought earlier. "What are those for," I ask gesturing to them.

"Oh, I almost forgot," she said, rushing over and picking them up, "This one will make your Adams apple shrink and make your voice sound more girly and light, your Adams apple is pretty small already and you voice hasn't deepened yet so you'll may be fine without it but it will certainly help."

"Is it reversible?"

"Yes completely, once you stop taking it, your Adams apple and voice will return to normal," She continued,"And this one increases the release of estrogen and decreases the release of testosterone."

"Oh okay," I say even though I don't really know what she's talking about.

Sensing my confusion Katie simplifies, "basically it will cause you to act more girly naturally, and it is also reversible, you should take both now and every day in the morning."

"Got it" I say committing the information to memory. I don't want to act any girlish than I already do, but Katie wouldn't have got them if it was a bad idea. I take the two pills they taste sweeter than I expected. Katie asks if I'm ready to go out because our 2 hours is almost up, I'm not but I tell her I am. We walk out of the dressing room and into the store I look around and see other girls-I mean I see girls shopping for clothes and things. I'm prettier than most of them, oh my good, why did I think that. I'm just a little nervous is all, I hope my hair still looks okay, I should have checked it. When we walk out of the store I start seeing a lot more people and I feel like they are all looking at me. I put my head down and like a scared animal try to make my body appear as small as possible.

Katie notices how I'm walking and leans over to whisper in my ear, "If you walk like that more people will stare."

"I'm scared," I admit weakly.

"I know, sweety, but pretty girls aren't supposed to walk like that."

"I'm not a pretty girl," I say not even sure if I believe it myself.

Katie ignores me, "pretty girls walk with their chin up, smiling. Use those beautiful legs of yours to take long strides, and make sure you sway your hips, okay?"

"I'll try, but I'm not a pretty girl, okay?" I compromise. Katie doesn't say anything. I try to remember her directions chin up, okay easy enough. smile, sure why not. long strides, okay. Sway my hips, done. I can feel my butt jiggle every so often from the swaying and the boobs jiggling every stride. I look up at Katie She's is walking in the same way She directed me to. She looks confident, happy, and beautiful. I can only hope I look that good as I continue to mimic her walk.

We walk the rest of the way in silence, she is usually not this quiet so I feel like I did something wrong again. We enter the parking lot and I can't hold it in anymore. "Katie stop," she stops, turns in my direction and looks down at me and I look up to her,"I want to apologize if I've been at all difficult this-this is a new experience for me and-no I'm not going to make excuses." My eyes start to well up with tears, "I know I'm not the perfect brother or person, and you are perfect and so supportive and.." I have to wipe tears off my face and I notice Katie's eyes are watering as well,"I just wanna thank you for all you do for me and for everyone and I wanna thank you for today, I couldn't have done it without you, I love you so mu-" I can't speak I'm sobbing too hard, I look down.

I hear that Katie is crying too, I look up and I can see she's crying as much as I am. She gently grabs me by my exposed shoulders and looks me directly in the eyes, "listen to me," she says through her tears, "you are perfect, and I love you too, I love you so mu-" She explodes into tears and so do I. She brings me into a warm sisterly hug. I can feel our boobs rubbing up against one another, but I don't care. We stand there embracing and crying on each others shoulders for a while. I never want to leave this hug.

She pulls away first, she looks down to me smiling, I look up and smile back, she lightly wipes the tears off my face. "Are you okay?" She asks.

"I'm better now," I say, "thank you."

We both take a few deep breaths trying to compose ourselves.

"You were right, you know, your not a pretty girl." she says.

"I know," I say, looking back down with a tinge of sadness in my voice, I know she wants me to be but I'm just not.

"You're a beautiful young woman." She says. I look back up at her and giggle.

"I don't know if I'm ready to be a girl or a woman," I say, "But I think I can be your little sister for a while."

"That will always be more than enough for me." she says and kisses my forehead.

"Now. Is my makeup alright." Katie asks.

"As beautiful as ever sis."

"thanks sis, I need it to be, now that I got some competition" she says giggling

"I surrender." I reply giggling back. maybe this trip won't be as bad as I thought.

We hear something drop to the side of us, we both turn sharply.

"Will?" dad says, ignoring the food he dropped, "Oh my god!"

"uh..hey dad" I say nervously, passively waving my girly hand. Well this is going to be interesting.

Author's Note: Wow that was certainly longer than the first one. Well, first off I wanna thank everyone who read the first part whether or not you enjoyed it. This part would have been released earlier but my cat decided he was more important so he rubbed his head on my mouse and in the process deleted all of my work, but I rewrote it better than before and learned an important lesson. By the way the model I used pictures of is named Courtney Tailor ain't she a beauty and I found the pictures through google so there you go. As always feel free to comment any questions, concerns, compliments, comments, comebacks, cornerbacks, quarterbacks, or another alteration. Anyway I hope you enjoyed this chapter of Will's story and I hope you'll stay tuned for the next one where different things happen!!! is that a good tease? Thanks for reading! Bye!