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Unexpected Chapter 2: New Friend

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I slumped in my driver's seat. It was now five in the morning Central Time, having crossed time zones, and I had been driving nonstop. After I made my escape I stopped by a gas station and bought a bunch of Red Bull to keep me awake for the trip as I had to cover as much distance as possible and I was giving myself a quick break by pulling into the parking lot of a Wal-mart. This is it. There's no going back now. I thought back on my family, of all the memories I had shared with them and how much I loved them. No longer would I be able to experience their comfort and security. Tears began to stream down my eyes as I wrapped my head around the reality of what I had gotten into. I buried my face into my hands and let the tears flow while emotions broiled inside me. Best to cry now while nobody is around; I'll need to stand strong in the days to come. I cried and cried until all the emotional turmoil was vented out of me. Once I had finished with the waterworks I looked at the print-out brochure of the academy I was fleeing to that was sitting on my passenger seat. I picked it up and began looking through its contents. It would be a nice place from the looks of it. It was part of a lively town by the sea and a nearby dune lake which meant good fishing. The idealistic conditions would make things easier as I worked out my situation.  I looked down at my breasts as if to confirm the already blatant fact that I was now a girl, sighing upon seeing they were still present. Just another hour Mason then you can sleep. Yeah right I never sleep during the day. All I'll get at best is a two hour power nap. I finished the last of the Red Bull can I had been drinking. scrunching my face up as I swallowed the liquid. I hated carbonated drinks. They made my tongue feel like a million tiny bees were simultaneously stinging it, but I had to drink the stuff to stay awake. Throwing the empty can into the makeshift trash can I made I put my hands on the steering wheel and put the car back into drive from the Walmart parking space I had decided to take a break in. Pressing on the gas I got back onto the road for the final leg of my journey. 

As I drove I made note in the gradual change of soil composition and plant life. More deciduous forest gave way to pine trees planted in rows with palm plants filling up the space in between as the soil went from clay to loam to a more sandy substrate. I'm near the area where my family always vacations in the summer, I'll have to watch out next year to make sure they don't suddenly stumble into me. About an hour passed and the sun was now beginning to rise and based on my GPS I'd be coming up on the town the academy was at soon. I rolled down my window to enjoy the crisp morning air. The forest began to fade and I was greeted with civilization and the distinct style of architecture that I was accustomed to seeing in this part of Florida.

"Drive 0.1 miles and your destination is on your right." My GPS signaled. 
"Finally here." I exclaimed in relief, flicking on my turn signal and turning right upon seeing a sign that read "Seaside Academy Girl Dorms" into a large parking lot with a row of palm trees planted in the dividing space between it and the road to give off that "tropical paradise" vibe. To my now left at the end of the parking lot was a building with a nice curvy design to it. Not spending time to admire the architecture I pulled into a designated parking spot for guests. Putting the car into park and flipping the ignition off I opened the door to my car for the first time in hours. I stretched my tense muscles as I stood up out of my seat. I closed the door and pressed the button on my keys to lock it. I'd get my belongings once I signed in and had gotten my room number. Here's to hoping I get a room to myself.

I made my way through the parking lot to the entrance to the dorms. Upon walking in through the automatic doors I was met with a lady looking to be in her early twenties wearing a white blouse and pencil skirt with her hair in a high bun sitting at the front desk. She looked up as she heard the automatic doors opened and smiled in greeting at me, not looking fatigued by being up at such an early hour at all. "Hello there miss!" she said cheerfully while I almost cringed at the formality. "What brings you here at this early hour? A girl your age should be getting her beauty sleep."

I scratched the back of my head nervously. Maybe I hadn't thought my plan all the way through. "Ummm I submitted an enrollment form yesterday and it was accepted. Is the name Mason Presin under a list of transfer students?"

The lady grabbed a sheet of paper and looked it up and down before her eyes finally settled. "Ah yes, the honors-AP student. Honestly we weren't expecting you to come so soon as it's still June even though we accepted your entry nigh immediately."

I tried to maintain eye contact with her to make myself appear less suspicious but my autism kept making me incapable of maintaining it for long. "Well the school is in Florida and I have the choice of coming down here spending time at the beach or be back up in Georgia and have to deal with only a swimming pool."

The lady chuckled, putting her hand up to her mouth. "You make a good point but I digress, you must be tired from the long drive, so I won't waste time. Feel lucky that you're a girl as the girl dorm is closer to the beach." She moved the mouse on her computer, her eyes dashing across the screen. "Your room will be 404. Ah, that's Lilly Baron's room. She's a very sweet girl I'm sure you'll like her aaaaaand before I forget I assuming you drove down here, correct?"

I nodded in confirmation. "I did, I drive the white Lexus that just pulled in to the guest parking. Do I need to move it?"

The lady shook her head. "Not at the moment as you should get some rest, but try to move it tomorrow morning after you've moved in" She looked towards her computer again and I could hear the faint  noise of the mouse scrolling coupled with the rapid clicks of the keyboard. "You'll have Parking Spot number 225. Now, would you like help carrying your luggage to your room?"

I nodded. "That would be much appreciated ma'am. I didn't bring much but I'm not all that strong."

The lady smiled at my polite attitude and pulled back the desk chair, getting up and moving around the desk. "It's fine. I need something to get the blood flowing." 

"I hear that." I turned around and started walking knowing that she would catch up with me. We walked to my car where I opened the door to my trunk and grabbed my gym bag as well as the game console backpack and duffle bag while she picked up the box that held my desktop computer and laptop satchel. Once that was finished we walked back into the building and she lead me to an elevator. Once inside the elevator she asked for me to press the button to the fourth floor. I did and once the elevator door closed an inquiry sprung to my mind. "Is it alright for us to awake Ms. Baron so early? I can wait a few hours as I don't want to intrude on someone else's sleep just because I couldn't wait to arrive here." It sickens me how easily I can lie. Ever since I was little lying has been something I was gifted at and I made use of that gift until upon becoming more religious I decided to be honest no matter what. Though it seems my knack for lying will help me during this time. Still, I wish I didn't have to.

The lady shook her head. "No, she'll be fine. Girl is very understanding and flexible. Oh by the way I'm Mrs. Finch, the dorm head."

I managed to give her an amiable smile. "Pleasure to meet you ma'am." 

Mrs. Finch beamed at me. "You're a very polite young lady, Ms. Presin. You'll make a fine addition to our student body."

I looked down, feeling a little giddy at the compliment. "I'm nothing important and please just call me by my first name." Ding! The elevator stopped and the doors opened to a comfortably wide corridor.

"Your room is the fourth on the left." Mrs. Finch tried to indicate using her head.

I nodded and walked down the hall and stopped upon reaching the doorway with Mrs. Finch following close behind. I stood at the door and looked at her, awaiting directions as to not do anything rash. She raised a finger and placed the box down before fishing a key out of the pocket of her blouse. "This will only take a moment." She inserted the key into the lock and turned it, opening the door once successfully unlocking it. She leaned in and spoke softly to the inside of the room. "Lilly? Are you awake?" I bent down to pick up the box and looked up upon returning to a straight standing position to see a girl with brown hair that was about as long as mine but less neat walked into view. She was actually pretty attractive with sparkling dark blue eyes, long eyelashes and ample curves. She was still in what appeared to be her pajamas, wearing a loose teal spaghetti strap tank top and pink pajama shorts or at least I think they're pajama shorts; fabric looked too soft to be Nike shorts, but it wouldn't be the first time I'm wrong. "I'm awake, I woke up early for some reason. Who's this?" She pointed at me.

"This is Mason Presin. She'll be your new roommate." Mrs. Finch responded
Lilly made a few swift glances between me and Mrs. Finch until she finally looked forward at me. Her face brightened like she had just laid eyes upon a long lost friend. "Yay! a roommate! I can tell you and I will be the best of friends!" she approached me with her hand extended to shake.
Doesn't this girl realize my hands are full? Nevertheless since I would spending two school years with this girl I figured I'd return the gesture. "It's a pleasure to meet you Lilly." I stepped inside the dorm room putting my belongings down for a moment enable to give the extended hand a firm shake. Formalities out of the way I let my eyes drift about the room to get a feel for my new living conditions. It was a large dorm with a kitchen area, lounge, bedroom and balcony. It really seemed more like an apartment than an academy dorm. Looks like I'll be living my fugitive life in style.
Lilly looked over my shoulder at Mrs. Finch "Thanks for the help Mrs. Finch, I'll help her get settled in!"
Mrs. Finch bowed her head slinging the laptop satchel off her shoulder and laying it next to the door. "Oh! Mason." She tossed me the key she had used to open the door. "That's your room key make sure not to lose it." 
I caught the key and nodded. "Thank you ma'am. I'll make sure not to."
Mrs. Finch waved beginning to close the door. "You two have fun now." and then the door was shut.
Lilly smiled at me. "So, whatchya wanna do."
I blinked at her with heavy eyes. I just got here and she asks that question? "Sleep. I just drove for six hours straight keeping conscious off Red Bull with no rest."
Lilly's eyes widened. "Oh dear, whatever caused you to do that?"
I sighed reluctantly. "I'll try to explain later but first I seriously need to lay down." I had already explained my cover-up story to Mrs. Finch so it's not like I still needed to formulate an excuse I was just too tired to talk.
Lilly giggled. "I bet. the beds are over there." She pointed to her right and I moved out of the small corridor to see two full size beds. Femininely decorated but it'll do. Paying no attention to the rest of my surroundings I walked over and flopped on the bed that was still in neat order which meant it was unused and let sleep overcome me...

I awoke sometime later to find myself laying on my back. I lifted my head to find Lilly slowly unzipping my fly. "Umm what the hell do you think you're doing?"

Lilly looked up and made eye-contact with me. "Uuuuuh well you see...Uh I.."

My eyes flicked throughout the room. My duffle bag had been opened and my laptop was sitting on the nearby coffee table. "You went through my stuff?"

Lilly threw her hands up in defense. "I was only trying to help you unpack while you slept and then I noticed you had only boy underwear in your bag and your clothes smelled like a boy wore them so I was checking to make sure you weren't some pervert cross dressing enable to get unlimited access on the girl's dorm!" She explained frantically. 

I blinked. "And I thought I read too many manga... Well I can't lie to everyone here. You promise not to tell anyone what I'm about to tell you?" 

Lilly nodded fervently. "I do."

I sighed. getting up off the bed and sitting on the nearby couch. "The reason why I have a bunch of Guy clothes was because up until yesterday I was a guy. I woke up the previous morning to suddenly find myself a chick. If I stayed home I would only face humiliation by my peers so I submitted an enrollment form and they accepted my form almost immediately. I then during the night ran out with my belongings and drove here. So there you have it. Your new roommate is a genderbent fugitive. It's hard to believe I'm sure but that's the truth." I threw my hands up in exasperation.

"Hmmm that does sound rather like something out of a bad sitcom, but it when you add up all the pieces it makes more sense than other possible scenarios." Lilly stated.

I looked up at her. "Wait what?"

"What I mean is sure it's far fetched but it matches up with everything. You got accepted into the school on short notice which means you're not stupid and if you had a sex-change surgery you'd have made a transition so you'd have girl clothes and if you were a perverted boy cross dressing you wouldn't bring boy clothes unless you were stupid which I already disproved. Besides in no possible situation would you drive for six hours straight with no sleep." Lilly rambled off.
I tilted my head a little. "Yeah, I probably should have set it up for me to be less conspicuous."
Lilly lifted a finger. "Aaaaand since you're unaccustomed to this lifestyle I will teach you all about how to be a girl."
I jumped back. "But this might be temporary so I don't really want to get used to living like this..."
Lilly jumped on the couch and crawled up to me, sticking her head upward with a sly grin. "If you really believed that you wouldn't have run away from home now would you? Deep inside your subconscious you realize you may never be a guy again. Oh!" She exclaimed interrupting her train of thought as an idea popped into her head. "Do you have any pictures of yourself as a guy?" Lilly inquired, swiftly changing the subject.
I exhaled in relief. Thank god, for short attention spans "Yeah, I do." I grabbed my laptop and clicked on a folder where I kept pictures of myself though there were only a few due to my dislike of 'selfies'. "This is what I looked like." I started going through the pictures.
Lilly's eyes sparkled. "Ooooo you were a cutie! A shame you had to become a girl, and I can definitely see the resemblance between girl you and boy you. But seriously a boy that cute shouldn't be erased from the world. I'll tell you what. You follow my directions in learning how to be a girl and I will help you find a way to get your manhood back. Deal?"
I groaned. "Fine. Just don't go overboard with your 'girlification'. I may not have been the most masculine guy but I was still born one."
Lilly smiled. "I make no promises. Now as for clothes." She looked down at my breasts and poked them as if examining them causing me to leap backwards and fold my arms over them in protection. "Yeah I think you and I are about the same size."
I eyed her suspiciously. "What the hell are you talking about?"
Lilly clapped her hands together and tilted her head with an innocent smile. "Breast size of course!"
My eyes started to drift downwards towards her breasts but I stopped myself and clenched my eyes shut. "Don't say that so bluntly! It only gives a guy the subconscious command to look down!"
Lilly covered her mouth to hide her giggling. "Oopsie sorry! But anyways my two best friends and I were intending on going shopping this Wednesday so I'll just lend you some of my spare clothes to help you along until then." She skipped over towards a closet next to what I guess would be my bed now.
I gulped. "Oh boy."
She searched through the closet. "Ah here it is!" She flipped around to reveal a frilly pink bra. 
I backed away to the opposite edge of the dorm. "Gah! it's pink!" I shivered in disgust.
Lilly looked at the bra. "I think it's cute. Don't tell me you think pink is too girly a color. Might I remind you you're a girl now?"
I shook my head vigorously. "It's not that it's a girly color! I just hate the color pink okay!?"
Lilly cocked her head to one side. "Oh, if it's simply a matter of taste then I think I can find something else" She went back to searching through her closet.
I sighed. "There is such a thing as a tomboy you know."
"I know. I'm a tomboy myself." Lilly responded, the sound muffled by her voice being directed at the closet wall. "But that's no reason not to look nice."
I grumbled and went to my backpack and unzipped it pulling out my game console. "it's ironic."
Lilly looked out from the closet. "What is?"
I looked up at the ceiling as I recalled past memories. "Back when I was little people used to say I looked a lot like a girl. And even as I grew older there were features about my physique that were rather effeminate like narrow shoulders and smooth hands as well as a general lack of testosterone. This transformation seems almost like nature simply said to itself. 'hey, why not just make him a girl?'."
Lilly drew her lips into a thin line and they twisted them into an uneven angle. "You're a very mopey person aren't you?"
I continued my upward gazing. "No. I mean as of right now I'm a girl there's no changing that and I'm still not quite comfortable with that fact but I'm not going to be in denial about it and force myself to be depressed because of it. I mean sure It won't be as easy as being a dude was. No more peeing standing up, I'll have periods, can't be shirtless in public anymore, if my preferences somehow change I'll likely deal with pregnancy, I guess leg shaving won't be an issue as it seems I'm naturally void of body hair now. You get the picture being a guy has benefits. The only thing I didn't like is having to work up the guts to ask out a girl it just is so terribly nerve-wracking for me."
Lilly smiled sincerely. "Hey, if you find a way to return to being a guy I'll go out with you."
I cocked my head to the side. "Really?"
Lilly ducked her head back in to continue perusing her wardrobe. "Sure! Based on the pictures you were rather easy on the eyes and you seem like a nice person."
I furrowed my brows. "Wait, but girls usually friendzone nice guys. I'm not quite sure I even am a nice guy. It would be conceited of me to claim that myself though it's what I aspire to be."
"You talk a lot don't you?"
My mouth slightly curved up in a half-smile. "Yeah I do."
I could hear Lilly giggle softly from inside the closet. "Good, I like to talk too and my two friends aren't very good with maintaining conversation. I'll introduce them to you once we get you settled. Ah here we go will this work?" She pulled out a plain navy blue bra. 
I sighed. "Yeah sure. Emasculating as it is it has to be better than these linen wrappings."
Lilly looked at me sideways. "Linen wrappings? Hold on a second." She pounced on me and worked my shirt off leaving me topless so she could get a look at what I had used to support my new assets. She snickered a few times before bursting out into laughter. "It's like something out of an anime!"
I folded my arms and mumbled, my cheek blushing in embarrassment. "Well I saw it in some anime and for lack of a bra it seemed like a good idea."
Lilly took deep breaths to stop her laughing. "You watch anime too? Awesome!"
My face brightened. "Do my ears deceive me or is my new roommate a fellow otaku?"
Lilly suddenly hugged me. "Oh you just keep getting better and better Mason!"
I wheezed from the strength of the hug. "Can't breath. Boobs getting squished."
Lilly opened her eyes which had been squeezed shut. "Oops sorry! Now back to business. Put this on!" She held up the bra.
I gave her a half-lidded stare. "Do you think guys are taught how to put on bras? because we're not!"
Lilly covered her mouth to stifle a giggle. "Oopsie I forgot. Here I'll help you. Turn around for me please."
I complied and did a 360 bounce so that my back faced her without speaking a word.
Lilly blinked at my rather cartoonish action. "Well that's one way to do it. First off let's remove these wrappings." She grabbed a pair of scissors that had been resting on the coffee table we were sitting next to and tugged at my linen wraps causing me to suck my gut in from the pressure on my breasts. With a quick snip! it was over and the linen wrappings fell onto my lap. "alright put your left arm through this strap. Good now squeeze your right arm through the other one. Now give me your hands. Man you're not a very flexible person are you? Don't worry I'll guide your arms. Now hook in the clasp and there!" She took her arms away from me and I looked at the undergarment that now covered my recently gained assets. "Now we oughtta shift the weight around..."
"No no! It fits perfectly!" I protested backing away from her and covering my breasts with one arm. "By the way what size are you?"
Lilly made a cat face. "34E why?"
I covered my mouth. "Jesus Christ! And this is your bra right?"
Lilly nodded.
I hung my head in shame. "Somehow I feel like this is divine justice. I like tits and when I turn into a girl I get these massive knockers, but I like tits no more than any other heterosexual guy so why me!?" I shook my fist up at the ceiling as if I was challenging the heavens.
Lilly couldn't help but laugh. "Oh dear you are a paranoid creature aren't you? Anyway how does it feel?"
I tugged at one of the bra straps. "It feels fine I guess. This begs the question. Do bras actually serve a purpose?"
Lilly tapped her chin in thought. "Well not officially. Personally I feel like it offers some support for me since I have big boobs and all but I know other girls who say otherwise. I also feel it keeps them from bouncing."
I scratched my head, uncomfortable with the topic although it was necessary. "I have ASD and one of the symptoms is over-sensitive...well...senses, so I guess I should wear them to keep from getting a rash in the area."
Lilly's face brightened as she remembered something. "By the way you should also wear these." She got up and went back to her closet before tossing me a pair of matching panties to the bra. As far as panties go they were rather conservative looking a lot like boxer briefs. "I'm going to cut you some slack. They're not boxers but they're often called briefs and the like in lingerie stores so I guess this pays homage to what you're used to?"
I shrugged. "It doesn't matter I'll have to get used to it one way or another."
Lilly lifted a finger. "Hey, I know what I said earlier but you shouldn't just drop everything you have been. You seem conflicted about this. At some points you're like 'too girly' and other points you're like 'guess I have no choice'. Okay, yes you need to adapt to your body but you don't know that this is permanent and there may be a way to reverse this so don't abandon the fact you lived sixteen years of your life as a boy."
I started taking off my shorts. "I think we're both being rather wishy-washy on this."
Lilly smiled and shrugged helplessly. "Yeah I guess you're right. Heh, you got a nice ass."
I blushed. "Don't say such weird things!" 
Instead of responding Lilly furrowed her brow. "How do you do that?"
I raised an eyebrow. "Do what?"
Lilly pointed at my face. "Blush with only one cheek."
I raised a hand up and touched my right cheek. "I dunno, whenever I blush only my right cheek actually increases in color" I took my shorts and walked into the bathroom. "I'm going to change underwear in here. I can't trust you not to say anything perverted."
Lilly folded her arms with a disappointed frown. "What kind of a guy are you?"
"A genderbent one." I answered sarcastically before closing the bathroom door.

Once I was in the bathroom I slid off my boxer shorts I had been wearing and then held the panties in front of my face to inspect them. I feel I should be more resistant to this. I hope I'm just being compliant and there isn't a part of me inside that is gradually welcoming being a girl. I thought to myself. No, I have my boundaries. I am not going to be so obstinate as to pretend I am still a guy. I'll wear girl underwear and girl clothes but hell if I'm going to pick up girly hobbies. I'll still do what I loved doing as a guy. Concede to the inevitable, but hold on to your core. Strategy. I at down on the toilet and slid the panties on up to my thighs then stood up to pull them up the rest of the way. "Alright I've put them on."
"How do they feel?" Lilly called from behind the door.
"Alright I guess, no longer have a dick to need breathing room with so the tightness causes less discomfort." I pinched my fingers in between the fabric and stretched it out a little then grabbing my shorts and putting them back on before opening the door to be met immediately with Lilly's smiling face which quickly turned into a frown upon seeing I had my shorts back on.
"Awwwww why'd you put your pants back on?" She whined.
I went over and grabbed my shirt pulling it over my head. "Because I don't make a habit of walking around half-naked."
Lilly pouted. "You're no fun. Oh, I set aside some more spare clothes I had aside for you to use. You can keep them as a gift, but we'll need to get you some more clothes than what you brought and my contributions."
I walked over to the TV and started pulling out the cords to my game console and beginning to set it up. "Yeah I figured as much. I have a list in my gym bag of things I need to buy." I pointed back towards the couch where my gym bag sat while plugging in the cables for my X-box then listened to the responding sounds of Lilly walking over and pulling open my gym bag before rustling through its contents.
"Hmmm toiletries, a new Sim card, fishing gear, and clothes." She listed off as she read.
"That's all I could think of at the time there might be more I don't remember." I said as I finished hooking up the console.
Lilly kept her eyes on the list. "Well I can share my shampoo, body wash, and toothpaste with you though the former two might be girly brands."
I was now unpacking my desktop. "That's fine as long as you're willing to share."
Lilly nodded. "Alright, so all you need for toiletries is a toothbrush. and as for fishing gear I have that too you'll just need a fishing rod. Why the Sim card?"
"Satellite tracker wired to the one I have now. Don't want my parents finding me."
Lilly made an 'O' shape with her mouth. "Your family very tech-minded? You got a lot of gadgets and technology. Nintendo 3DS, Phone, Camera, I-pod, Kindle, X-box, Laptop, Desktop, and whatever doohickey this is." She held up the Mi-fi device.
"That's a mobile wi-fi hotspot. Wasn't sure if the dorms here had wi-fi so I brought it with me, but yes my family is rather tech-minded. My dad works for AT&T so his technology-related job just causes technology to be a common thing around our house."
Lilly put the hotspot down. "So want to go shopping for the stuff today?"
I shook my head. "I'd rather just get myself settled in and relax for the rest of the day."
Lilly tapped her chin in thought. "Okay I guess that's fair. How about tomorrow? My two best friends and I were planning on shopping anyway and I'd like to introduce you to them!"
I looked back at her. "Sure, but you sure you want to welcome an ex-guy into your friend group? Your friends might not be so open to the idea."
Lilly placed her hands upon her hips. "And you think you'll make it through without someone who knows your predicament to help you? I won't tell my friends about your situation this can stay between you and me."
I sighed and shifted my body to look straight at her. "You're doing enough for me already, so I don't want to burden you all the way into your social life."
Lilly now folded her arms and smiled. "You're sweet, but it's really no problem at all. I can help keep your secret safe if you're with me and my group."
I shrugged in defeat. "Fine we'll play it your way."
Lilly grinned triumphantly.

We spent the next few hours unpacking my luggage and setting myself up in the dorm and once finished we had lunch then she insisted on seeing the video games I had so we played video games for the remainder of the day. It finally came time to go to bed something that I had been longing for. We each got into our respective beds after I convinced her that I'd sleep in whatever I wanted and not some camiset pajamas from a lingerie store and I let sleep overcome me with little resistance. Maybe things won't be so bad after all...

End of Chapter 2
-In this segment my fictional counterpart arrives at Seaside Academy and meets his new friend, Lilly! No, the fact that both my MCs in my TG stories attend private schools is not intentional... well sort of. Convenient plot devices for uniforms because I'm a straight-up otaku.
-Notice a difference between this Mason and real Mason? I'll tell ya. Unexpected Mason is less energetic than me. I figured I already have a perfect self-insert as Lucas so I would write myself differently.

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Therandomguy5's avatar
This is probably really late but 360 is a full circle, 180 is what you want to face the opposite direction.