Subgoal Sissy: Desperate streamer slowly becomes a girl pt.2

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Subgoal Sissy: Desperate streamer slowly turns into a girl ch.2

[heyyyy, I really hoped you enjoyed the first part, and welcome back again if you read it in 2021 x. I’m really glad that we’re going to be able to have so much fun on this journey together. I promise I’ll do my best to keep this story coming but this is way more exhausting than I thought it would be. hope you enjoy! Mona x]

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Chapter 2
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Checking how he looked in the tiny feed from his new webcam, Andy realised a few problems. Although his room was dark enough to hide the hideous mess of clothes and trash that had piled up behind him, there was no way and viewers were going to make out his face in any clear level of detail. He was by no means looking forward to to being visually displayed to the whole entire world online, and after seeing himself on the screen he felt even more self conscious about the way he looked. But he was determined to be professional, and made a mental note to buy fancy LED lights as soon as people started donating to his stream. God, he couldn’t wait to be rich and famous.

He pushed the dark tangled hair obscuring his face one way then the other in a last ditch attempt to look more presentable for the stream, but quickly noticed that his long mop, blurry video feed and poorly developed un-masculine features all combined to made him look a quite a lot more androgynous than he was comfortable with being.

It had to do for now, he knew time was passing. And as he couldn’t think of any way to look smarter or manlier right then, he just loaded up his new game, distracting himself with setting up the stream. After everything he’d been through in these past miserable years, he wasn’t going to let anything trivial like this ruin mood or frustrate his plans again. He’d never had an opportunity like this before, in his opinion, and with a heart full of determination, pushed the final button to start his stream and waited for the viewers to pour in.

-

Around five minutes five minutes later, a certain message appeared in the chat.

“get back in the frame babe. I cant see your face”

That was a strange thing to see, Andy thought to himself. He expected it would probably take a few hours before the first few viewers came into the stream, and was so completely absorbed with his plan that he’d forgotten about the encounter with his new “friend” from the day before. But after he’d checked his phone and processed the message, he felt like he’d just nearly been hit by a car.

He stared at his phone, the stress of the day before pouring back into him. He read the name again to make sure. ApeyA-bomb22. The sole viewer of the stream so far, and already as weird as the day before, was in the chat again. He dreaded the thought of having to deal with this weirdo yet again. He just wanted to get on with his stream.

A plug had been pulled now however in Andy’s brain, and his confidence had slowly started to drip out away from him. And seeing that more, longer messages were popping up on his cheap outdated phone, he chose to place it on his desk to get a better view and tried to think of how he could react to thi-

“Get back in the frame right now or you WILL be in trouble”

Andy had a poor setup. There wasn’t any way for him to actually see if he was in the frame (he couldn’t see how his stream looked while it was running). But instead of being even a little bit grateful for this somewhat helpful advice, he felt only confusion and a small amount of fear. He knew who this guy was, but he failed to fully understand what was going on. Something didn’t feel right.

“Get back in the frame so I can see what I paid” -

Andy, still confused, automatically centered himself back into the middle of his chair from his slump. He didn’t know why this guy was being so hostile, but was guided by his fear and natural instincts into following his blunt instructions.

“much better” Andy saw in the chat, right after he moved.

“its nice to see your pretty face. But dont be shy say something”

“youre much better than I expected sweaty”

“but why didnt you make an effort for me? Dont you like your new toy?”

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All of a sudden he realised. The webcam he got was from Apey, not his mother. He’d completely forgotten about the link to his Amazon wish-list he’d put below his stream(no one was ever actually there to ever see or mention it) and Apey had gone out of his way to spend his own real money to buy this expensive camera barely a day after meeting him. How deranged was this person? Andy thought, worried. This person either had to actually have some kind of weird obsession starting with him, or be so well-off that something this frivolous didn’t mean anything to them.

Either way, despite the strangeness of the scenario, Andy realised that he actually did feel some gratitude for this stranger’s kind gift. He didn’t understand why he was being attacked, but then, he thought, maybe he’d be annoyed too if he’d spent that much money on someone and they didn’t seem to appear grateful enough.

He remembered hearing from someone once, that It’s always important to never look a gift horse in the mouth. And although he didn’t fully understand the saying, he tried to make sense of the situation and his feelings, and decided that he should at least try to compose himself and try and keep the stream going for a while.

“hha, wow, sorry” Andy said, smiling into the camera “I didn’t realise you were there, sorry.
I cant believe that you spent so much money on this for me. This camera’s amazing thank you!” He waited for a response in the chat. Maybe there’s a chance he won’t be weird today, he told himself.

“glad you like it” Andy read.

“i thought you deserved something special being all alone and all the other day”

“and I know you’re shy, but I’ve been very generous to you today and its actually my birthday today aswell.

“I was thinking you could do something special for me today to really show me how grateful you are”

It took a few moments for Andy to process what he’d just been reading. He didn’t get what he was hinting at so replied “uhh ssure. What do you have in mind Apey? Do you want to pick what game I should play today?”

“how about you go make yourself look nice. Ive been very kind to you today. Go put on something nice and put some makeup on. Then we can have a proper stream.”

“haha good one!” Andy said, instantly taking the message as a joke. “no, what do you really want me to do?”

“seriously?..” A-bomb replied.

“all I’ve shown you is kindness and this is how you respond..”

“im trying to be civil”

“go change your clothes and put some proper makeup on, or I’ll make you regret it”

This really stumped Andy now. He’d started to hope that yesterday was just a one off anomaly, but now it was clear that this guy was nuts. He still felt like he could probably dodge the messages with some of his humour, but oddly found himself actually intimidated at the way he was being spoken to. There surely wasn’t any way he could do anything to him though, he told himself. He couldn’t believe that this guy actually thought that he was was a girl. Even though his voice was a little squeaky, and he didn’t show up too clearly in the camera, and his hair was maybe getting too long, he didn’t accept that he looked like a girl.
After a few seconds, he tried to dodge Apey’s request with a “hha but I dont own any makeup” which was true,” and I always dress like this.”
There’s no way he was going to take A-bomb’s threat seriously.

“hmm well how about you go see if your mom or sister has anything you can borrow, and do something with you hair. You should be taking care of it.” A-bomb replied, in the chat.

“I dont have a sister, and my mom’s not home.” said Andy” I dont t-think she’d want me mooching around in her stuff. And please” Andy really wanted this conversation to end. “i don't really like makeup”.

“This is my final warning. Im not taking no for an answer..”

“Either you go look for something now, and come back with some effort put in, or im contacting my bank and telling them to refund me for that webcam. Amazon will demand you pay for it then. I know youre poor, you wont afford that. And youve used it now so they wont let you return it.”

“look. Im going to give you 5 minutes, and if I come back and my pretty girl isnt there looking back at me...dont make me do something ill regret..”

All this had ramped up so much more that Andy was expecting. He didn’t know how Amazon worked, and A-bomb was right. This camera was top of the range; he couldn’t afford that. He’d just spent the last of his money buying this new dlc for his game he was playing and would actually be ruined if what he was saying was true.

Really for any normal person this wouldn’t be a problem at all. He stressed and knew he had no way of knowing if Apey would actually go through with this threat but he turned pale imagining what his mom would say if she got a call from the bank saying how overdrawn he was. He thought about how he could try to return the camera and try to make it look unused, but after a quick inspection he found that he’d scratched the side when he was getting it out of the box! And after imagining how grim his life would be if he lost his brand new camera, he only grew more upset.

Sweat was starting to form around his forehead when and he couldn’t believe his luck. He realised that the clock was already ticking on his demand and he didn’t have any time to deconstruct A-bomb’s threat. He had no choice he concluded. In his pathetic, helpless state, he knew he had no choice. He started to panic, and he knew he had to move now. God, this was such a small thing that he was being threatened over, but felt like this could potentially ruin his life. He stood up from his chair with a struggle, swallowed the fact that he had to now do what he was being told, and awkwardly left his room to see what he could find from his mother’s room.

Sometime on the way to his mom’s room he thought about how lucky he was that she was still working another late shift. She probably wouldn’t be back for a few more hours and he couldn’t start to imagine what he’d do if she came home right now. He really couldn’t believe that he was actually going along with this and stopped himself several times, but no matter how many times he told himself he was being an idiot, in his weak state he thought that this truly was the best thing to do. Who knew what else Apey might try to pull if he got angry.

Straight away he saw and went to his mom’s vanity table. He’d never took the time to look around here before and had never imagined himself going in here to look for makeup. Why was he doing this? He thought to himself again.

With the table being mostly empty he guessed that he might find something useful in one of the drawers. He barely knew anything about makeup, and really just wanted to do the bare minimum that he might get away with. A small black tube, lipstick. He knew how that worked, he thought as he placed it on the table. Along with what looked like a pencil, and another small black tube he decided that he’d found enough.

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Nervously, he picked up the lipstick and twisted the base, extending the red, but as he saw himself in the mirrors reflection he froze. “what the fuck am I actually doing?” he said to himself. He couldn’t bring himself to move the lipstick any closer to his mouth, and couldn’t stop thinking about how wrong what he was about to do was. This wouldn’t make him gay he had to tell himself, this was just something he had to do once. He just had to do it just this once, then he could move on with his dream, get famous, and one day this would be something to laugh about. But he felt like he wanted to cry. He really felt wrong and thought about going back into his room right then and going to sleep forever. Looking at the lipstick one m-

Shit, he remembered, he only had five minutes. He’d forgotten his phone in his room as well and didn’t know what time he had. Sitting on the stool and with a sudden rush of fear and panic, he decided to do everything he could to get this done in time. It might already be about to run out, and the fate of his future could be hinging on this moment.

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He swiftly moved the lipstick up to his lips and pressed it firmly along each one. Deep bright red. A shock to see in the mirror. The texture felt cold on his lips. He grabbed the pencil he assumed was eyeliner and carefully attempted to draw along his left eye. He’d never tried makeup or anything like this before so his eyes flinched every time he tried to get close, leaving uneven marks across his lid. He didn’t know if A-bomb would criticise the quality of his attempt, but in trying to make the line more even, he ended up colouring in most of his eyelid black. To make his look more complete, he shaded all of his other eyelid in too. God, he thought, he was even thinking like a girl now too.

Opening the final item confirmed that what he now held was mascara. He’d seen people in movies use this so went to give it his best shot as quickly as he could. Carefully holding the wand close to his left eye he tried to close his lid while he watched himself in the mirror.

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It turned out to be trickier than he thought, as he tried not to poke himself in the eye, and blinked onto the brush a few times. Moving it to his right eye he again slowly closed his lid onto the wand, once, twice, three times looked in the mirror, and then slowly repeated the motions again and again until he decided it would do.

He didn’t know how to process what he now saw in the mirror, but the messy job he’d done made him feel strange. He didn’t know why exactly, but all he could think about now, was what he was supposed to wear and how little time he thought he had left.

The wardrobe, he thought, obviously she’d have something in there. Time was quickly running out so he ran straight across the room, nearly tripping on the way, and threw open the wooden door.

A number of similar looking colours and shirts were revealed to him. Whenever he saw his mother coming home or leaving she was only ever wearing basic white shirts and black pants so it didn’t surprise him when he saw them taking up most of the space in front of him. But looking closer, and remembering the limited time he had left, Andy considered that anything with buttons could be too much of a hassle, so he looked for something easier along the rack.

To his surprise, at the rightmost end of the rack he found not one but a multitude of what he could only describe as “sexy” looking dresses, skirts and unfamiliar shapes of fabrics. It was understood by Andy that his mother spent nearly every hour of every day working at her boring office job, and the house bills meant that she never had enough money or time to go out clubbing or on dates. He’d never seen any clues of a partner or even heard about her life outside of work at all really. As far as he was aware, she didn’t have a life. He guessed that maybe these were clothes that she used to wear before they were poor, but they seemed so organised and looked after. All he knew for sure was that he definitely wasn’t going to touch anything from this end of the rack. He wasn’t gay, he told himself again. He took a breath and crossed his fingers.

He sighed a deep breath of relief when he found a simple looking cotton t shirt at the other end of the wardrobe. Once again, he caught himself self conscious of how he was acting in this situation and that he shouldn’t be glad in any way to see a female piece of clothing. But he knew what he thought he had to do, so thinking of his future fame, he tugged off his baggy guy-t-shirt, carefully allowed the new one to fall over his head and pushed his arms through the short, soft, gentle sleeves.

He didn’t have time to see how he looked now but noticed the size of the large neckline on his new attire. Definitely not something a guy like him should wear. He bravely decided that maybe he’d get away with not changing his pants as his lower half wouldn’t be visible to the camera anyways. Then desperately he looked around the room for a brush. Not much time left now. He had to do something with his hair and get back.

Several drawers surrounded the room and bags lay on the bed, but he couldn’t see anything resembling a brush. Surely he’d find something in the bedside drawer, he thought, as he ran alongside the bed. He pulled open the draw and to his delight, again, he found a suitable looking brush right there in the center. Yanking it out, he instantly started pulling throu-

Andy’s gaze and attention was stolen by some very important looking letters. Red text adorned the top and body of the texts and they didn’t look good. He hadn’t really given himself the time to think about finding something private or “sexual” in her drawers but as soon as he saw “FINAL WARNING” and “LAST CHANCE TO COMPLY” he experienced a freezing chill that halted the gears in his brain. His mother was hiding something bad. Holy shit, were they actually in trouble? He panicked. He knew they had a lot of bills to pay, but did he actually need to start worrying about something bigger?

He immediately tried to get a closer look at the letters, noticing how feminine his arm looked in his new sleeve and several more pages underneath with some handwritten notes at the side. He couldn’t believe that his mother could be hiding something like this from him but gained a larger sense of compassion for her dedication to pay things off for them. But before he had a chance to start reading anything further, he dropped them all. Shit. He had to get back to his room, A-bomb was probably furious, and he still had to brush his hair!

Surely lacking any time to spare, he kicked the drawer back closed and started to run back out to his bedroom, brushing his hair as he went. He ran straight past the mirror, not even sparing the time to look for a second and awkwardly pulled the brush through his left then right sides of his longish tangled hair. It hurt to pull through the knots so rapidly but he continued to pull it through each part of his hair like his life depended on it, and as he was nearly back at his chair he let it fall into a middle parting, setting two tidy parts to fall on either side of his face.

He leaped into his desk chair and threw his headphones on as quickly as he could, panting to catch his breath, fearful and exhausted. “H-Hello? Hello? Are you still there-please did I make it?” he gasped.

He had to have made it back in time and begged himself that this was true. Andy felt shamed about following orders this submissively and appearing so desperate, but the thought that he might have just done all this for nothing suddenly appeared and was making him scared.

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“h-hello?” he tried one more time..

Eyes wide, darting between the lens of the camera and his phone, he thought briefly about how he hadn’t had the time to see his finished look. He could feel the mascara still drying on his eyes and the deep neckline of the shirt exposing his skin. What if his mom came home now and saw him like this?- He saw a flash in the chat.

“…...you’re late”

“Oh god! Oh god! I’m. Sorry. I’m sorry! Jus-. Just don’t take the take the money back. Please!” Andy started shaking. “I got stuck in the other room sorry! look, I did all this for you. Please, do I look okay? I truly am really sorry.” He felt his heart sink further and further.

“…

…...you’re late

...

…...but you do look pretty now...so I might let you off...

really you do look so much nicer now that you’ve made an effort. I like your lipstick

...

But it wasn’t nice to keep me waiting... That webcam wasn’t cheap and you could at least treat me a little better.

I didn’t think you were coming back. I was starting to feel like I’d wasted my time and my money

I think you need to make up for this

You tried to do what I asked, and you do look hot. But you still made me upset when you didn’t need to

Do one more thing for me now and I think we could still be friends.”

Nothing in his life had prepared him for dealing with such a rush of changing emotions. Stress and pressure on this scale wreaked havoc on his brain. Unable to speak, he was so incredibly relieved to read that he’d been given another chance, but also horrified at being complimented on his looks as a girl. Without questioning the seriousness of the situation at all, he prepared himself to ask of what he needed to do next.

“Tell me...” Apey wrote” like..really tell me.. how deeply sorry you are, and how badly you want to make it up to me.”

“drag it out in a really.. sexy.. way and don't take your eyes off the camera.”

“Tell me how you think you’re going to make it up to me and don’t forget to say my name”

“if your ideas not acceptable and if this isn’t the sexiest thing I’ve ever seen then I wont be impressed. And I wont be able to be friendly any more”

“oh and dont forget to blow me a kiss at the end.. Slowly”

Disbelief and the sound of breathing. Andy’s stare fell downwards. Again his untrained emotions were tangling up any logical brain processes he still had, leaving him to slowly but painfully accept what he was about to do. He wasn’t gay, he wasn’t one of those sissies, he thought, and there was still every chance that someone he knew could join the stream as he was doing this. Still only one viewer he checked. Did he have to do this? Not at all. But, maybe, he did. He needed to become someone one day and maybe this was the only way to stay on that path.

He took one deep breath, and still looked down,
slowly weighed his options,

and breathed once again.

He came to a choice, and he knew what to do.

Then looked up into the camera and commenced his speech.

I am not a sissy, and I’ll be famous soon..

“Sssssssssso… Apey?.. I’m really sorry” The words struggled to come out of his lipsticked mouth

“I know you must have had a harrd day… but you’ve still been soo kind to me” what else should he say??

“umm.. you know I’ve always been kind of lonely on these streams, and it really warms my heart knowing that there’s someone out there who thinks of me” after fighting the idea, he reluctantly pouted his lips a little and angled his head.

“And when I found this camera waiting for me at home, I couldn’t believe how lucky I was” was he being sexy enough? What does sexy mean, what did he want him to do exactly, what have I got myself into..

“you rrreally..”dragging out the syllables “are one of the nicest, sweetest..”think sexy “most handsome g-guys I’ve ever met” He really hoped this was enough, as tears were actually beginning to form in his eyes.

“In fact..” He needed to make this good enough” If I ever happened to meet you one day, I’d think I’d have to thank you in a reallly.. proper way” What did I mean by that??

He looked down at his top, blushing, then slowly back into the lens “you really mean a lot to me Apey.. Abomb...my sweet Apey.. and… you make me feel sooo.. special..

He paused for a lengthy time, then coming back he said “Happy birthday A-bomb sweetie.. This is for you..”

And then feeling more vulnerable than ever before in his entire life, he brushed the hair out off his face, carefully pushed his red lips together, and maintaining unblinking eye contact with the camera, slowly motioned a lengthy, sensual kiss straight towards the camera. He lifted his chin as he moved. Pausing at the peak of the motion, letting his lips drift apart, the sound of the wet kiss echoed through his silent house. Then carefully moving his head back down with his lips still open, he stayed there in silence absorbing everything he just felt.

“sorry I was just cleaning up” appeared in the chat.

After he realised what that message just implied, Andy was thrown into another state of anxiety. What the fuck had he just participated in!? His mind jammed up completely.

“I’m sorry if I scared you before but that was amazing. I knew you really liked me a lot and I’m satisfied with what you did” A-bomb continued. “

“I accept your apology. Now continue with your game, I’m sorry if I interrupted you”

Andy was shaken and mentally disturbed. He couldn’t believe the state he’d let himself fall into. He must look like a full-on sissy right now, and this guy actually thinks he’s an actual girl. He took a minute to slow his heart rate down and realised that he’d somehow gotten through this. He’d won, he told himself. That was a pretty demeaning thing that he’d just been (kind of) forced through, but he did it. Maybe, coming back to his senses a little, this just showed how powerful he really was, and that he had the strength to do whatever it would take to make him famous. He still felt a little sick, but was starting now to feel more normal.

With his confidence slowly returning, and the lack of any mirrors in his room to remind him that we was still wearing a low cut female shirt, bright red lipstick, dramatic eyeliner, and a heavy dose of mascara, he decided that the worst was actually finally over. That strange guy still thought he was a girl, but Andy had the camera now, fully in his possession and he couldn’t think of any way that Apey could force him into doing something like this again.

He sat back up straight and pulled himself to his computer and decided to get back to the video game stream. In fact, after about twenty minutes, he’d somehow got back into the swing of it all and had gotten so engrossed in the game and his excitement about having a camera, he nearly completely forgot about everything that had just happened.

For four more hours the stream continued, until he knew he had to go to bed. The night had turned out to be a really fun time, and A-bomb even stopped being weird completely and acted like any other person you might find in a normal stream chat. He didn’t see any more new viewers come to him that night, but he had so much fun with his camera and ended up so tired, that when he went to change to his pyjamas he was surprised that he was still wearing his mom’s shirt. He then went to bed happy for the second time in his life.

-

It felt so good the next morning to wake up after having such a great day. Andy still felt exhausted, as he always did in the morning, but he couldn’t stop thinking about the fun he ended up having the night before as he went downstairs to find some breakfast.

Strange, he thought. It didn’t look like his mom was downstairs and he hadn’t heard her come in last night either now he thought about it. She must have come home really late but already left to get a head start. The thoughts of his mother suddenly made him remember the letters he found in her drawer last night. Putting the cereal back into the cupboard, he decided that he’d better go check what those letters were about before he lost the chance. He was certainly scared of finding out how much trouble they really might be in, but knew he had to look and so left and went upstairs.

Outside his room however, a brief glimpse of his brand new expensive camera shone in the morning light. It caught his full attention, and after feeling a new urge, remembered all the events of the night before and how he didn’t actually get to see his completed look. He still wanted to go and read the letters, but maybe they could wait until after he checked his stream archive online and watched a quick replay of the stream.

As the machine slowly warmed up he checked his girlfriends social pages on his phone. He still hadn’t heard much from her in a few days now but even now still didn’t find any new messages. No new pictures were on her page, so maybe she must spent last night studying. April was always so much smarter than him he thought. Maybe he’d get to see her at school some time.

He found the page containing the copies of his previous streams and slowly clicked on the most recent file. To his surprise he saw just his normal boring self. He’d forgotten that he started the stream in his normal guy-mode, though he did still look semi androgynous, so then cautiously skipped ahead a few hours, anticipating shock and discomfort, but something was making him want to see.

“Holy shit”, he sat back from his pc. “I look like a girl!”

A beautiful young charismatic girl truly was displayed on the screen now before him. The lighting did make mask some of his features slightly, but he was astonished that at a few hours prior, he had been that small cute girl on the internet before him with the shoulder length parted hair, black smoky eyes, bright red lips and low cut top. Mesmerised, he saw the way she giggled at her own jokes, actively spoke to the chat and even flicked her hair and tilted her head just like any other real, charismatic girl her age would. He didn’t remember acting like this at all. She seemed so natural, and the squeaky voice complimented the mirage so well. None of this seemed real to him at all.

One small detail adjourned his dream however. According to the stats on the website log, two new viewers had joined the stream without his knowledge. Apparently they were there during the start of the stream, around the time of his embarrassing apology. There was no way of knowing who they were but he couldn’t help panic himself with the idea that other people knew he was acting like a sissy, and that it could have been people he knew. He deleted the file of the stream immediately. But then sitting there panicking, thinking about all the people he’d told about his stream before he noticed something dire. Earlier he must have read his clock wrong and was going to be late for school again!

He’d already been late more than the tolerated amount of times at his school so knew he had to hurry.

He tugged on the first pants he could find, quickly found a t-shirt, leaped towards his bag and started his sprint to the door downstairs. There would be a severe punishment waiting for him today if he didn’t make it on time and he couldn’t bear to imagine his mother’s disappointment if he got himself expelled. For all he knew, something like that might destroy her mind completely. So yanking on his shoes and starting in a jog, he raced towards his school route like everything depended on it.

-

Fifteen minutes later, Andy’s fears managed to get him inside his school grounds with seconds to spare. He was in a mess of a state, and was surprised with how poorly out of shape he’d gotten. He just needed to find his way to his first class, If he could remember which one that was, and then he’d be okay. No one was was around so he knew he had to hurry, and rushing as much as he could manage he went from corridor to hallway until he felt like he was near the right place.

Another student going the opposite way to Andy gave him the strangest look he’d ever received before. No one ever gave him any attention at all so having someone fully stare him and turn their head to look back at him was not only a brand new experience for Andy, but it made him feel very uncomfortable. He had to carry on though as he looked back ahead to navigate the school.

Turning one final corner he saw the last of classmates funnelling into a door. This has to be the right one, he thought as he hurried to join the end of the queue. But as he made it behind the last person waiting to enter, he was surprised to be faced with none other than his sweet girlfriend April, leaving the room with a large stack of papers.

“April!” he let out.”how are you??”

Her expression turned cold when she stopped and realised the person talking to her.

“Andy...” She did not sound pleased with him. “...why the fuck are you wearing makeup?”

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~
ok, so the next chapter will be posted next month, and the next about a month later.
but if you cannot wait,
new chapters will be posted twice a month on my new patreon: patreon.com/ramona_loveletter
so i know this approach may not be so appreciated,
but I’ll try and make it worthwhile
the next part is already uploaded there to read today,
love you all
mona ;)
x

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