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ramona_loveletter

Author: 

  • ramona_loveletter

Organizational: 

  • Author Page

Audience Rating: 

  • General Audience (pg)


ramona_loveletter



stories

Subgoal Sissy: Desperate streamer slowly becomes a girl

Author: 

  • ramona_loveletter

Organizational: 

  • Title Page

Audience Rating: 

  • Adult Oriented (r21/a)

Other Keywords: 

  • streamer
  • streaming

 

Subgoal Sissy: Desperate streamer slowly becomes a girl

 

ramona_loveletter

TG Themes: 

  • Reluctant
  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Estrogen / Hormones
  • Hair Salon / Long Hair / Wigs / Rollers
  • Sissies

Subgoal Sissy: Desperate streamer slowly becomes a girl pt.1 (intro)

Author: 

  • New Author
  • ramona_loveletter

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Reluctant
  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Partial Transformations
  • Sissies

Other Keywords: 

  • streamer
  • streaming

Permission: 

  • Posted by author(s)
hphones sml.png

[Hi everyone. I started this story early in 2021 but unfortunately gave up on it too soon. Now I’m back with several parts pre written and edited and hope to continue much further. This is going to be a slow burner, but things will ramp up. There will be pay-offs, but I want this series to last and to give something to look forward to. P.s. also, I am trans, and the way I feel romantically has drastically changed since when I used to read stories here in the past. So if this story is missing that special feeling, or if you have any other advice, I’d love to hear about it. Also I’d be warmed if anyone remembers my story from the first time round. Lots of love, mona x] next part in a few days ;)

-Everyone in this story is 18 or above-

(this chapter isn’t very sexual, but I’ll make it up to you in the next parts)

Intro

Andy was a loser and he knew it. He wasn’t a class clown, a braggish jock, an aloof enigma or even a high achiever. But truly, by every definition, he was an absolute loser. He had no attractive qualities, no funny quirks. He’d tried to become popular, countless times before, but day after day of being ignored had grinded his persona to a beige-grey pulp. He had nothing to offer to anyone he met. Dust in the air made more of an impact on people’s lives than he did. And being fully aware of the problem, Andy had grown incredibly desperate. When he wasn’t dissociating completely, all he longed for was any possible ounce of human attention, and so it came to be that he was only a few bad days away from believing that he’d probably be invisible for the rest of his life.

He really didn’t understand why he’d become such a loser, but he knew that he didn’t know how to change. So he gave up trying. Buzzes and flushes would grow inside sometimes, elevating him to pathetic levels of excitement whenever someone looked like they were about to talk to him, or whenever he thought that someone was maybe talking about him. But they never did, and they never were, and so little parts of Andy’s humanity were eroded away with each awkward embarrassment and day that went by.

Hiding from his feelings, he’d often be found staring out of windows, or staring at his desk thinking about games, videogame-streamers or how much time there was until the bell might ring, leaving his schoolwork unfinished, and teachers ignored, which massively affected his grades. And whilst losing interest in schoolwork isn’t the most uncommon thing for a teenager, his behaviour (appearing shy and brain-dead) led his teachers to agree amongst themselves that he simply didn’t want to try in class, and so they decided to use their limited time on the students who actually cared about learning.

Other people in the class noticed his pattern of staring at things in silence from an early date, and quickly agreed that he was never going to have anything to say to anyone, and that even looking at him was a waste of time. From the first few nervous days at school he’d hoped that they’d suddenly start talking to him. But the end of his final school term was soon approaching, and he knew that that was very unlikely. He was going to be starting college this year and he still didn’t know how to make friends.

Somehow the ‘dweebs’ who got bullied were even more popular than Andy. And in his lonely reflections, he’d even felt jealous of them from time to time and even sometimes dreamt of getting bullied himself in a sad longing way. These kinds of thoughts kept Andy in a negative emotional loop, where he’d break down his confidence before it could properly build up, keeping him nervous and pathetic through all hours of each day, and leaving him unable to talk to anyone without appearing, first, afraid of them.

Somehow, however, although most of his attempts to make friends had been completely ignored, and also much to his own confusion, he had managed to make and keep one loyal friend from his early years way before he started school. That friend was his girlfriend. April.

April was a youthful, self starting, beauty, who was definitely going places after college. She was one of the most attractive girls in the school, had worked her way into the good-books of nearly every social circle and always had something to smile about. Andy always struggled to get her attention though, and saw a side of her the rest of school didn’t. Sometimes when messaging each other, Andy’s suggestions of a nice date would be met with “I really don’t have the time” and “but who would pay? You don't have any money.”. Sometimes she didn't reply to his messages for a week, and she’d sound annoyed if he tried to join in conversations with her groups of friends.

Every day Andy was afraid that she’d break up with him out of nowhere, or that this would all turn out to be some sick kind of joke. He had no idea what she saw in him at all But usually he found some reassurance in the fact that she’d stayed with him for all this time. And although she kept him from talking to her friends, would only meet with him if she requested it, had only kissed him three times in several years, never laughed at his jokes, would go missing for days, and was honestly a cold and distant mystery, he loved her with all of his heart.

Next to April, on the rare occasions that they were actually seen together, Andy did not have much to be proud of. He was shorter than nearly every other guy in his year group, and less physically developed than nearly everyone else. A few times he’d tried starting an exercise routine, but always gave up within a couple of days. Because of his moodiness, he took poor care of his hair, and his tangled dark mop was now nearing his shoulders. He was pale from gaming, always wore baggy clothes and had mostly just given up trying. He really didn’t know what his girlfriend saw in him.

Living alone with his mother gave him freedom to be undisturbed, which allowed him to fall into a daily routine of ignoring everything else in the world to play video games until the sun went down, continuing to play until it was nearly time for it to come back up, and then watching streamers and youtubers in a digitalised coma until he fell asleep.

His mother, used to look out for how he was doing, and tried to keep his spirits up but had to take up more shifts at work, thanks to his father leaving, and now always had to stay at work late. With no other siblings, Andy had to look after himself, and although an empty house was sometimes fun, he would never leave his room, and felt desperately lonely the moment he stopped looking at his screens.

A solution to everything came to him one day however, that he, by himself, could become a famous and popular streamer on the internet. Everything he’d seen and learned from his years of watching personalities online had given him the knowledge and skills he’d need. He could create an image of himself so refined and different to who he was that he’d be able to make friends with anyone online. He’d never be lonely again and he knew that he’d be able to help pay his bills, letting him see more of his mother again. They’d never had much money to buy things like nice clothes or holidays, but Andy had slowly saved up enough to pay for a computer that could just barely stream games, and now becoming famous was all that he wanted.

This was without a doubt going to be a miserable last term at high school for Andy, and he hadn’t even started to think about what he would do at college. But he did feel pretty confident that any day now his streaming career was going to take off. He wouldn’t have to worry about an education ever again soon. Anxiety and desperation still riddled his mind through most days and nights though. And although he hid it somewhat at school, all the social deprivation, the distance from his mother and “girlfriend”, the failures to get his grades, the helplessness he felt and the happiness he saw in others (people who actually had friends) had turned him into one of the weakest, most embarrassing and desperate people on the entire planet.

All he had to distract himself was his plan to get through each day as quickly as he could, to get home to his room and start streaming, as he had done for nearly a year now, and that is where our sissy-story starts to set off.

---------------------------------------------------------

Chapter 1
New_Project__1_-removebg-preview.png

Sliding his bag across his bedroom floor, Andy went straight to his computer desk. He couldn’t remember if he had any homework to do, but he knew he’d be able to play the new crexworld expansion for the rest of the night, uninterrupted. He’d spent the last six months arguing on reddit about how amazing this expansion would be, and now that he’d finally saved up, he couldn’t wait to prove himself right. His girlfriend was annoyed that he’d wasted so much money on this when he already had other games, but she was busy studying tonight any ways, and this seemed like a very worthwhile investment to him.

Andy really wasn’t athletic, but he’d actually tried to jog the last part of the way home today to make sure he had time for his plan. He was very enthusiastic and now that the game had been pre-installing for about eight hours on his struggling internet, he was almost ready to start his stream.

None of his broadcasts had actually ever been successful before and most people tuned out after only a few seconds, but today Andy was determined. If he was one of the first people online in the world to stream this game’s expansion, then he would absolutely guaranteed get some major traffic. The servers were going live in ten minutes, which gave him enough time to set up his gear. He couldn’t afford a webcam, but he’d written some jokes on some paper next to him to use if anyone started watching and the software he was using, although free, was very familiar to him now. Today was going to be his lucky day. And after this, he’d be on a one way highway to fame.

After he’d estimated how long it would take to get his first million followers, he was already live, waiting on the main page of the game. He only had one screen, so had to check his phone to see if anyone was waiting in his chat yet. Zero.

“Oh well” he thought. “The expansion’s not technically live just yet, so they’re probably just still on the way.”

He send out a few notifications on his social media, announcing his big stream, and something caught his eye. His girlfriend was on a night out with some of her besties and they looked like they were all having a blast. It looked like someone was having a house party, and he remembered her saying something about a birthday last week. And sure, he was a little jealous. He was never invited to any of these gatherings, and she’d often made it clear that she wished he’d stopped wasting his time on his “pathetic little streams”, but he reassured himself by imagining the feeling of pride he’d have when his future streaming success would let him pay for exotic holidays, and expensive dates. She’d be proud of him then.

-

Five hours later he had his first view.

-

Suddenly struck, he shot up in his chair. What should he say? He panicked. He fumbled for his notes on his desk and looked to see if their name was in the chat. They hadn’t typed anything so he had no idea what they were called.

“Oh no,” he thought. “What if this is just April checking in. I can’t let her see how bad I’m doing.”

He spouted something about how much he was enjoying the new dlc tonight with as much fake enthusiasm as he could muster (after five hours glued to his screen, it wasn’t a lot). To his disappointment, he wasn’t really enjoying the game that much, and it was starting to look like a big rushed mess, but no one would watch him unless he seemed happy and enthusiastic, he thought.

“#$!*#” was all that appeared in the chat, and his view count quickly returned to zero.

Andy was flattened. He didn’t even have a chance to tell one of his jokes, and he’d already gone. Not knowing what else to do, and put-off from the game, he tapped the message on his phone to reveal what had been said by the now-revealed milkman86.

“Pussy” is all he saw. “Nice,” he thought to himself. He’d never been offended by anything like this before, but he really had been planning this day for over a year, since the expansion was announced. He couldn’t afford many big games like this and wouldn’t get to try something like this again for a long time. He was so upset, tears were actually starting to form around his eyes.

“Oh god, maybe I really am just a pussy.” He whimpered, with his head in his hands. “I can’t do anything right. Why am I such a fucking pussy?” He cried, weighing everything up. And falling down into his chair for a while. “Why am I actually crying?”

-
...
About five minutes later he looked up at his phone on his desk, red around his eyes, and saw, to his utter disbelief, that his chat was filled with so many messages that it was asking him to scroll down for more.

Something had to be wrong here, he thought. He wasn’t even in the game any-more and had been kicked for idling. Had that guy come back to apologise, or make fun of him again?

“pretty girl” he saw in the chat. “why are you crying :(”

“please don’t worry you must be so funny”. He read on. “You sound like a wonderful girl”. “you’re not a #$!*#, you’re amazing”, “a strong independent woman”,

“you deserve more views”

“show cam”

These were some of the ones he noticed from the seemingly endless barrage that he’d just missed.

Overwhelmed by the flurry of emotions he was currently pushing through, Andy was excited to see that people were watching actually the stream. He rushed to see if anybody was still there, and kicked himself for not noticing sooner.

They were definitely still there, but Andy was surprised to see that all these messages were all from one guy. A user called ApeyA-bomb22.

Quite let down, and almost certain that this was just another jerk just here to make fun of him, Andy’s worries started to return. He felt deeply embarrassed that someone had witnessed his pathetic breakdown, albeit just through audio, and didn’t understand why they were calling him a girl. His struggle through puberty had left his voice a little higher pitched than most of his other male classmates, but he didn’t actually sound like a girl did he? He stressed. Maybe his cheap mic was just distorting his voice a little.

“Oh, hi...” Andy said. “I didn’t realise anyone was here, sorry”. Feeling embarrassed that he was apologising, he fell quiet again.

“Don’t be sad” A-bomb typed. “I'll cheer you up”.

Though still mostly confused, Andy was starting to think that this guy wasn’t just another troll at all. He wasn’t comfortable being addressed as a girl, but maybe this was someone who was just genuinely trying to be nice to him. Andy had had a really tough struggle with trying to get attention from anyone in his daily life, especially today, and this weird stranger had kind of gently struck his heart a little.

A warm feeling of hope started to form inside of him after he’d thought for a few seconds, and although he didn’t really know how to move on from here, he realised that this could be the chance that he was hoping for. If he could somehow manage to keep this guys attention for just a little bit longer, his stream might show up to more people on the main website, and he could definitely get some more fans. If he went back to zero viewers, his stream would instantly return to the bottom of the list, of everyone else streaming this game, and all his dreams would be shattered. He slowly took a deep breath in and then out, and then decided that he was going to ignore the girl part of the messages and loaded his game back up.

“T-thanks.. um.. whoever you are” Andy struggled out, wiping the remainder of the tears from his eyes. “Have you, seen much of this game yet today?”

“No. worked long today” he read. “wish I could see u though. Show webcam”.

Andy really didn’t know what to say about that, and already felt put off now from his attempt to keep going. Maybe he should just turn the stream off now and try to forget this ever happened.

“...haha” he managed awkwardly. “I don’t have a webcam though sorry”. Which was true. Andy and his mother didn’t have much money at all, and his setup was very basic.

“thats a shame. your stream is nice though.” “why have you stopped talking?”

“Sorry!” Andy spat out in a fright. He felt very embarrassed again, with how emotional and apologetic he was being, but he realised that this guy could be about to leave, as quickly as he appeared. He couldn’t mess this up.

“Just a little...” he managed. “I’m just not used to anyone watching me really. Barely anyone ever clicks on my stream and they never usually stay for long”. He felt even more pathetic now, but all of this just fell out of his mouth.

Now loaded back into the game world, Andy set his character off moving. But in a flash on his phone, he saw that he’d just gained a new follower. After not finding any for nearly two months, he was now almost at fifteen! He couldn’t believe his luck.

“Wow thank you! Thanks for following the stream!” Andy said. “You’re gonna enjoy the big boss that’s coming up in the next zone. Glad you’re having fun!” Maybe this day wasn’t so bad after all, he thought.

“wow”.”could at least say my name” He read, after a long pause in the chat.

Confused at why saying the name could be so important, Andy decided to just say “Thanks ApeyA-Bomb22” in a brief sort of way, and went to start talking about the game again. God this guy was being a bit weird, he thought. But Andy understood that whatever small compromises he had to make to keep a follower would surely be worth it in the end.

“No”. Andy saw in the chat now. “You have to say it nicely. And call me A-Bomb. Say it as friendlily as you can, and say how much my follow means to you. If youre not going to be grateful im leaving. I have other girls that want me in their streams. They appreciate how kind I am. Maybe I was wrong about you after all”.

This guy was insane, Andy thought, distraught. This guy really thought that he was a girl, and just because of his squeaky voice and his cheap microphone. Surely he didn’t sound that much like a girl, he told himself. But he was acting all emotional and pathetic tonight, he realised. But maybe he was just confused. Andy didn’t know what to think.

This was all very strange to him, and he didn’t feel comfortable. But somehow, through his strongest insecurities, he was still considering just playing along again, and thinking of the future of his stream. This guy was really weird, but how bad could it honestly get? He thought. Its just some words on a screen, and nobody else is even watching. Andy really didn’t like being thought of as a girl, and really didn’t want to play along as one either. But he wasn’t really asking for that much, and he could probably just sort of play along for a little bit, and surely he’d be distracted by the game after a few minutes.

Still nervous, he tried to clear his thoughts and prepared to sound confident. He’d show him how grateful he was. Even if this did feel horribly demeaning. He was going to be this guy’s girl for a few strange minutes.

“S-Sorry A-Bomb! I didn’t mean to sound so rude!” his voice came out, much weaker and squeakier than he’d envisioned. “You really are soo kind! And I’m really glad we can hang out together!”. Impressing himself with how he’d managed, but now feeling even more embarrassed than he had all night. He thought that surely he had to have this guy now.

“There. That wasnt so hard was it. I knew you were a nice girl. I was only joking about leaving though haha” A-bomb said.

“Haha! you’re so funny!” Andy replied, not knowing what else to say, feeling a little creeped out, but coming off very cheerful. He’d manage to please this guy and could now finally get on with the stream he’d been waiting for. He started to look for his joke notes again.

The stream continued, and to Andy’s delight, without anything else strange happening. After really getting into his stride, and telling A-bomb what he thought were some very good jokes, the stream ended, nearly two hours later, way into the early hours of very quiet morning.

Andy was so pleased with the result of the night. The A-bomb guy was a complete weirdo at the beginning of the encounter, but after a while they really seemed to connect. And although no one else joined the stream after A-bomb, he was pleased that the one fan he did get, was extremely engaged and involved, and would probably come back again. Now when people joined the stream in the future, he’d at least look a lot more legit. He did have fourteen other followers on his account, but they’d all stopped watching shortly after following him. “This was the start of something good.” Andy felt. “I’m gonna be famous in no time.”

-

School flew by the following day, and as he came closer to his home, Andy noticed a box by his doorway. How strange, he thought. He hadn’t ordered anything, and his mother certainly wasn’t in the position to buy things online. Maybe she was planning to surprise his for his birthday. Excited and still riding the buzz from the night before, he raced to get the box, but because his week had started to go so well, his run accidentally started in a small skip. He immediately stopped himself, feeling embarrassed and confused, collected himself and walked the rest of the way, only to find his own name on the package’s label.

With his mother at work again, he took the package and his bags upstairs, loaded up his computer and checked his phone.

‘2 new messages’

The first being from April, he immediately opened. He hadn’t seen her at all today at school, and was in such a good, he wanted to talk to her and share his good news.

Unfortunately for him, however, the message was only to tell him that she needed to cancel their study session for this week. Meaning that they wouldn’t get to see each other outside of school for at least a week and a half now. And to add to his disappointment, the second half read ‘btw going to netball tonight, then doctors, so don’t message me x.’

He honestly didn’t remember her ever mentioning a doctors appointment, or even a netball club for that matter. He was always forgetting things from staying up so late though he thought. Why did he feel so sad about these messages. She was only telling him that she’d be busy, and not to waste his time, but it all came across so cold. He was just being a baby again, he thought. And he really needed to grow up.

Going back to his other message, he saw that something had happened with his amazon account. He always got phishing emails, but this one was saying that something had been purchased from his amazon wish list by an anonymous account.

Taken back, he was confused. None of this made any sense to him. He looked at the package again and back to his phone, and saw that it said a ‘professional HC280L HD webcam’ had been ordered to his address.

And lo and behold. A professional HC280L HD webcam was exactly what he found inside the box that he had. He pulled it out of the box, causing some papers to fall to the ground, and held his new prize in admiration.

Ever since he’d started streaming he’d wanted a webcam like this, and now his stream would look so damn professional. He couldn’t wait to test it out, but then suddenly realised that this must have been a present from his mother. He hadn’t told her that he streamed, so this was an incredibly lucky pick of a gift for him, he thought. He then realised that he should probably put it back into the box and pretend he hadn’t opened it, but because she probably wouldn’t get back until after midnight, he thought that he’d have plenty of time to test it out before he had to put it back.

So Andy quickly rushed to log onto his new game again and start up his streaming software. This was awesome, he thought. He was finally going to be a professional streamer, and he thought about how his stream would look tonight.

But in those papers that fell on the floor was a personalized note that Andy didn’t notice.

And if he had grabbed this, and read what it said, he’d have found the special message: “hey babe, hope your on tonight. Cant wait to see your pretty little face”.

lens.png

[Authors note: I’m sorry if this wasn’t arousing enough for the time you spent reading it, but a lot has been planned for our poor naive Andy here. And as the gravity of his situation, slowly starts to unfold, I’m sure you’ll be more than satisfied, and begging for more.]

~mona <3

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

Author: 

  • ramona_loveletter

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Reluctant
  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Partial Transformations
  • Sissies

Other Keywords: 

  • streamer
  • streaming

Permission: 

  • Posted by author(s)

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]

------------------------------------------------------------------------------------------------------------------------

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?”

lens.png

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.

lips1.png

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.

lips1.png

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.

mas1.png

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.

lens smal.png

“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

Subgoal Sissy: Desperate streamer slowly becomes a girl pt.3

Author: 

  • ramona_loveletter

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Reluctant
  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Partial Transformations
  • Sissies

Other Keywords: 

  • streamer
  • streaming

Permission: 

  • Posted by author(s)

[ok guys (and girls), if you’re wanting this to get spicy, it will. I promise, but all in due time..

*I have been updating this story over at @https://www.patreon.com/ramona_loveletter
and have just released chapter 7, along with a saucy halloween tale
I’ll post ch 4 here in late november. x

--------------------------------------------------------------------------------------------

Subgoal Sissy: Desperate streamer slowly turns into a girl ch.3

Chapter 3

New_Project__1_-removebg-preview.png

Andy just froze. His girlfriend hadn’t moved either but from the tone of her sigh he knew there’d be consequences. And then ever so faintly, deep within this moment, a departure was felt, into a new world of change.

He struggled to focus on anything around him now. April’s shape was moving away, but as he came-to he managed to say her name.

“What?
What could you possibly have to say about this Andy? What good reason could you possibly have for coming here looking like this, wearing makeup like some bimbo whore?” Her retort made it through to him, but the unfolding weight of the matter was simply too much and, unable to form an answer, he stood there silent. He really had no good reason.

“Look” April started. “I’ve done so much for you.” Her eyes bore into his soul. “We’ve always been together, despite all your... issues, and it’s not like I ask a lot from you. You know you can’t embarrass me in front of people like this. And if you ever did I wouldn’t stand for it. But why are you doing this to me? I thought you loved me. This doesn’t make any sense!”

April had really worked herself up into a full swing of rage but, hesitating to leave one final time, she revealed to Andy her ultimatum:

“Look, Andy.. You know I can’t let you into class like that.” She paused. “I don’t care if it’s starting now, I just cant let that happen. Imagine how disgusted everyone would be. My friends would never let me live it down”. Shamed into paralysis, Andy took every in sentence with greater and greater sadness.
“Either you go take that off right now, or I’m never talking to you again.
The bathrooms are that way idiot.
What are you just standing there for? Go!” She left past him abruptly, clutching her stack of papers aggressively.

Andy hadn’t caught his breath from his rush to get to school, and this did not help him recover. A minute might have passed while he stood there and thought but despite his poor record, and being so close to the classroom door, he knew he had no choice. April, though cold and unfair, truly meant the world to him. And he didn’t want to make her life any harder in any way at all. He certainly didn’t want anyone else to see him like this either, so as things started to spin around his head a little less wildly, he remembered where the nearest toilets were and ran, shielding his face with his weak shaking hands.

Nothing in his life ever seemed to go right for poor Andy, or anything that did always had snags. Incidents much less-severe than this were what made him into the insecure and hesitant failure he was, but to be shaken like this was s truly unprecedented experience for him. And unfortunately for Andy, as he was nearing the door to the toilets, a harsh voice beckoned him from behind.

“What are you doing over there!? You should be starting class right now, not mooching around in the halls! Come over here. Who are you?” the voice grew louder as Andy heard footsteps approach him. The toilets were there right in front of him but he stood there terrified knowing the voice belonged to a teacher. Getting into even more trouble was the last thing he wanted but when they asked his name he didn’t know what to do. He couldn’t show another person his full face of makeup. Any more embarrassment would kill him.

“Alright” A hand grabbed his shoulder, pulling him round, “lets see who thinks they can-...
Come on now you know you cant wear that much makeup in this school. Did someone send you here to clean It off?” Andy didn’t know what to say. “well I guess you’d better hurry and take that off as fast as you can then. I’ll come back here in a few minutes and you better be gone by then. Go. Don’t just stand there”. Andy, still on edge, paused then quickly turned back to hide into the bathroom. Did she think he was a girl? Why was she so trusting.

lips1_0.png

“Wait!” She shouted, stopping him in his tracks once again. “What are you going in there for the girls bathrooms are over there” She pointed to the other side of the hall.

There was no way she seriously thought he looked like a girl, he thought. But after seeing her impatient glare he knew that he’d regret wasting any more of her time. So then, hesitantly, he drifted over to the doorway of the girls toilets, hoping to god that no one was there, and slowly went inside.

It wasn’t bustling like he’d expected or even occupied at all but, just to make sure he was alone, Andy used some of his time limit to carefully check that every corner of the room was definitely empty and then ran closer to a mirror to see the damage done.

He looked ridiculous and kicked himself for being so foolish. Leaving the makeup on over night had left him with overly dramatic panda-eyes and smudged up red lipstick, way brighter than he’d realised. He had to get it off, now. So on the highest alert for any sounds from outside, he threw his face under the taps.

He rubbed and rubbed, stopping only to find paper towels to scrub even harder with, but there was sadly no hope when he’d dried his eyes and looked in the mirror. “Why wont this damn stuff come off?” He raved as he threw himself under again, now rubbing harder and scrubbing every angle. Eventually, with his face now completely red, he was devastated to see the traces still clear on his face. He’d managed to get the lipstick off, but it would be clear to everyone that he had makeup on his eyes.

With tears forming around those dark and smoky eyes, he couldn’t stop thinking about how his class was going to react and, even worse, how April would react. But through all his fears of social rejection he couldn’t avoid his fear of school, and remembered that he had a duty to return to class right now and really had no choice. And with that, he trudged in agony back to the classroom with dread filling up in every step he took.

-

Through the door’s window, he saw the class well underway. This left no choice but to interrupt everything and walk past most of the class. Nothing he ever did in school managed to ever get anyone’s attention, but this was undoubtedly going to be an exception. Maybe if he just looked at the floor, no one would notice, he thought, desperate for an answer. He creaked the door open and slowly stepped in.

“Aaaand who do we have here who thinks that they can just stroll into my class ten minutes late? Excuse me young man look at me while I’m talking to you!”. Andy meekly just stood there, turning on the spot, wanting to go to his desk but hesitating in the spotlight.

“Well don’t just stand there! You’ve wasted so much of my time already!” The teacher blasted “Go sit down right now and I’ll see you at the end of class. I won’t tolerate this kind of behaviour, and I certainly didn’t expect any more of this behaviour from you, Andy. How disappointing”.
Reeling with shame and refusing to look anywhere but the floor, Andy scampered to the middle of the room and sat down with his bag. He couldn’t dare look up to see if anyone was staring at him, but the feeling that they probably were was nearly unbearable.

Eventually however, class moved on without incident. Andy felt himself lose all focus as he was prone to do, and zoned out absorbed in both the events of the past few days and how useless he thought his school education was. He by no means thought he was already smart enough, but regularly thought about how whatever job he’d have in the future wouldn’t need calculus or algebr-

BZZZZ BZZ BZZZZZ..

“WHO IS THAT RIGHT NOW?” Exploded the teacher, breaking the class from a sleeping silence.

Andy nearly died right there and then as his phone continued to loudly buzz and ding from his pocket. There was an extremely strict no-phones in class policy at his school, and any kid caught like this barely lived to tell the tale. Surely this couldn’t go well for him, he realised as he tried willing himself out of existence. When the phone stopped, the class remained silent in awe. He felt he could hear his fear echo throughout the room.

“THAT IS IT” Steamed the teacher. “Claire, bring me Andy’s phone right this second!”. Andy knew he might never see his phone again after this. His classmate Claire came over to his desk and he woefully handed it to her out of his pocket and looked down into the woodwork of his desk. How could today get any worse after this, he thought. He hadn’t even gotten halfway through his first class.

“Well if someone thinks they’re too important to follow the rules in this institution” started the teacher after collecting the phone from Claire. “Let’s see what they think is so important to ruin a whole class over”. Moving the phone closer, she pushed her glasses onto her face. “If you want to come in here and ruin my class, then why don’t I read out whatever it is you just got? Does that sound fair?” The class was silent. “I sure think does” the rest looked up with interest.
Andy now looked up in shock. He didn’t think that was legal, and hadn’t even looked at his phone himself, but if that was a message from April then surely it would embarrass her to the rest of the class completely. April wasn’t here right now and was only on an errand before, but if embarrassing news spread around the school about them today, she’d definitely be dumping his ass by lunchtime.

The teacher fixed her glasses one last time, and read loudly and clearly the following message to the entire class.

““Payment received...Here’s a tip for the amazing job you did last night sweetie? You really make my...heart throb. After thinking about how much fun we’ve had, I’ve decided to invite my boys around for the next stream tonight. I really hope that you can make a decent effort again and look nice and pretty for them, I’ve said some really nice things about you and they’re really excited to see you. They’re, gonna, love you. mr A-bomb x.”

After failing to fully understand what she’d just read, the teacher glanced at Andy with concern and a clear tone of disgust. The others that weren’t fully paying attention before, along with everyone else in the class were all now staring at Andy in complete awe of this ridiculous situation.

Physical feelings of disgust were crushing Andy from every direction. He heard some giggles cut through the silence. If it was possible to cringe any more than he already was, he didn’t want to know what that felt like. Why was he being humiliated so much today? He cried to himself. He really couldn’t handle any of this at all and had no alternative than to just stay completely still and pretend that this wasn’t really happening. He just hoped that no one could see he was wearing makeup.

Andy fainted, and fell on his desk.

--------

All Andy could see were swirls and blurs. He attempted to sit upright but was taken back by the nauseating tingles swarming through his head. He couldn’t figure out where he was or what was going on but slowly found his way back to reality from a soothing calm voice that sounded familiar. He realised he was in the school nurse’s office but the sharp memory of his incident instantly flushed most feelings of ease away. None of his classmates were here, to his relief, but he had no idea how he’d been taken here. Holy crap, he thought when he saw the clock, he’d been out cold for nearly the entire school day. It was 3PM already and school had nearly ended.

“Wow, you look pale as a sheet dear. Are you feeling any better now? I was gonna get you sent to the hospital if you didn’t wake up soon”. Luckily he’d found himself with the school’s nicest nurse. Andy had heard students talk about how pretty she was, but felt deeply relaxed by her soothing voice He felt warm as her torch shone into one of his eyes, and then the other. “Cute eyeliner” she said. “Not often you get a boy brave enough to rock lines like those. Looks good on ya”. Andy immediately turned red and had to turn away from her.

A few short checks after, it turned out that Andy was okay but needed to take it easy for the rest of the day and get a good night’s sleep. As he was saying goodbye in the office doorway though, the nurse came up to him and handed him a leaflet. “Look” she smiled gently “It’s okay if you feel shy about it but I’ve noticed you a few times around the school and well, there’s a great gender therapist in town and he does weekly free meet ups you know?”. Andy just gaped confused. “If you ever feel like you want to talk to someone who knows a lot more about what you’re going through you can go see them okay? But you can always talk to me if you want okay? You best be off now. Stay careful now, byee.” And with that, Andy was ushered out of the room, leaflet in hand, before he had the chance to understand anything she was talking about. He was still quite dizzy from his collapse and distracted with how pretty she turned out to be. But with so little time left in his day, he tried to find his way to the school exit.
Right before he set off, however, he realised he didn’t have his phone. The thought of confronting that teacher again petrified him, but he knew he might be able to find it in the principals office, so off he went, feeling queasy and faint.

The wait outside of the Principal’s office seemed to last forever, and Andy couldn’t avoid noticing the strange ways everyone passing by kept looking at him. He felt a twisting in his gut when he tried to imagine the kind of rumours that must be spreading about him now. People were definitely whispering to each other as they passed, and before long a giggling group of girls his age rushed up to him from nowhere.

“Oh hey! So there you are! We’ve heard all about you. So you have this stream thing going on? Are you famous or something? I sell feet pics but do you like get naked and stuff?” Andy, still dizzy, couldn’t handle these questions but couldn’t leave before he got his phone from the principal. Right now he was stuck there with them, and desperate once again, tried to ignore them all.

They continued talking to him, excited, but even though he clearly wasn’t happy, another nearby group, of nerdy looking guys, came over quickly as well.

“broooooo, what’s your stream? We wanna watch. You play games right?” Andy, still wearing makeup and panicking, was now surrounded by about fifteen people. “Dude, I’m like watching streamers all the time, what’s your channel called?” This was too much to handle again. It seemed that the whole school must have heard about him by now, and that probably meant his girlfriend had too. Fortunately, the principal opened his door before Andy could faint again, saving him from disaster.

“look here” He said sternly. “I don’t have much time, so I’ll keep this brief. Frankly I’m appalled with your record in every regard this year. This class disruption should really be the last straw, but you clearly have something going on at home. You should not be wearing makeup in this school as well”. Andy couldn’t take his eyes off the floor. “Also, we are firmly against the idea of any students of ours doing anything sexual for money” Andy couldn’t respond or believe this mess he was really in.” in fact I’ve tried contacting your mother but I’ll need to see the both of you here as soon as possible. You are on very thin ice young.. man. Take your phone and get out of my office now”.
And with that warning Andy left the school as quickly as he could, straight past the people still trying for his attention, and ran the entire way home to bury his head in the pillows on his bed and cry in a really pathetic and very childish way.

---

It wasn’t clear exactly what rumours must have spread around the school about him, but he knew for sure that he’d never feel comfortable showing his face in there again. The summer holidays were a few months away, then he’d never have to see any of them again, but how could he go to class with this reputation now. He dreaded what sort of thing April must have heard about him now.

Andy laid in bed for what seemed like hours. Then after a very lonely while, he managed to feel a little bit better about the state of things. But as he contemplated never streaming again, he realised how bored he got with nothing else to do. He checked youtube but got tired quickly. He was uninterested by the games had already and didn’t have enough money to get any new ones. When he picked up his phone, he saw some unread messages from April but decided to throw it away from his bed; he couldn’t face that right now.
He realised that other than streaming, he didn’t really have anything else to do with his life. After all these years he’d never picked up a single other hobby, and couldn’t even think of where to start one now at his age.

After a while, Andy shuffled across his messy room to pass some time on his computer. But checking his emails delivered to him a major shock. “holy shit” he said out loud. “50 dollars. That guy donated $50! What’s wrong with these people?”. Someone donating that much to him was unbelievable. If only he had someone to show off to, he thought.
Then, elated, he realised that because no one ever paid him attention at school, or followed him on his stream or social media, that it was very likely that nobody at his school even knew how to find his stream! He couldn’t quit streaming with this type of money appearing now. Maybe he could just stream a little longer, he thought, just to see if the donator was there.

Andy noticed his mother’s shirt still lying on the floor from the other day. The “feminine” part of the problem wasn’t going away. His gut was telling him he couldn’t keep pretending to be a girl, and he knew they’d probably want to see him dressed like one again, but in his exhausted state he had an ingenious idea: He could stream without the camera. This would preserve whatever small amount of pride he had left, and if anyone asked, he could just tell them his camera was broken or that he didn’t feel well. He loaded up his stream, one of his newer games and felt a nervous rush of excitement once again.

Five minutes after he started, he had a whopping seven viewers. This was now his all-time record and he couldn’t believe it at all. A quick look at the chat showed him none of them were people from his school. These were all A-Bombs friends, but it wasn’t long until they were threatening to leave. Having vastly misunderstood the desires of A-Bomb’s friends, he was surprised to read threats of people demanding that he turn his camera on so they could see this “cute shy babe” their friend had told them all about.

One by one his viewer count started to decline. Andy’s only hope of becoming big on the streaming site was once again fleeting from his very grasp. He’d felt the rush that comes with gaining more viewers, a feeling of accomplishment and belonging unlike any other he’d felt before, and he couldn’t let that go. A slow glance to his side connected his eyes to his mother’s top on his floor once again. It lied there, as if in a new state of existence, like it was aware that he knew what should be done. What he had to do.
He felt the soft, familiar materials with his eyes, and noticed the effortless way it caressed and balanced on the curves the other clothes beneath it, as if weightless.

He looked down at his mothers shirt in his hands and, in acceptance, told the stream to wait.

Back in his mothers room he seated himself back into the view of the elegant silver vanity. With his eyes still dark from before, he already looked almost girly, but felt like making sure of things. Carefully taking the mascara tube from the drawer, he pulled out the wand.
The chemical smell intoxicated. He couldn’t keep them waiting but he couldn’t make mistakes. Slowly and cautiously he began retreading his steps. The brush moved gently to his right eye lid, which slowly closed on the rising brush. With every new brush he could feel his lashes changing and the smell of the mascara growing stronger. He moved it to his left eye and then again, slowly moved the brush upwards, as his eyelids moved back down. He repeated, up and down, up and down, then paused to reflect on his reflection. Were his eyes pretty?

He still didn’t know how most of his mother’s makeup worked, but decided to grab an alluringly vivid shade of red lipstick. He pressed it over his lips, rubbing them together. He almost looked like a whore, but seemed so, feminine, and not so out of place. Did he have goosebumps?
Inspired by the girls in school he grabbed a tight black choker necklace. Something a girl his age would surely wear, and with one last look in the mirror, he took off to save his stream.

- lens smal.png

Within 5 seconds of returning, camera online, a donation of $5 came through to his phone telling him to show off his bra. He didn’t know how to respond to that, but his startled blushing seemed to please his audience. Now within minutes the viewers were returning with the view-count now reaching almost fifteen.

Andy still felt incredibly nervous and guilty for disgracing himself like this, but could not deny the thrill of the unprecedented levels of interaction now taking place in his chat. People loved him, it seemed. As far as he could tell, none of them were from his school yet either. Would they even recognise him now? He mused. But as time passed on, the comments were starting to become increasingly raunchy. It turned out Apey was in the chat, ring-leading the viewers, and one after another, donations started coming through making progressively vulgar requests.

$5 came through to Andy asking how many times she’d had sex.

$5, $15 and $10 came through again asking, demanding her to show her boobs.

He couldn’t take all this seriously, but was still somewhat offended and surprised by the gall of these people. Were more of them starting to complain in the chat as well? Andy noticed several people banding together to complain that she was in-fact ignoring the donations completely and was an ungrateful whore for not doing what any of them were asking. He couldn’t believe it. These guys might be serious, but what was he supposed to do in this situation? Someone caught his eye with a donation asking to become her moderator, and that he’d protect her from the filth in the chat. This seemed like a fantastic idea to Andy, but they insisted on the condition that they would become friends.

Everything grew once again into a mess too big to take in; he’d never had so much attention in his life. So in a rash and flustered decision, he foolishly vowed to try and do some of the next donation requests. He was getting so much much money after all, and had made about $100 in the night so far. This maybe seemed like a fair thing to do, Andy decided.

The next donation: $5-” what’s the biggest dick you’ve ever sucked?”
This one came from Apey.

----

“Umm” Andy was tongue-tied and embarrassed. Twenty one people now were watching, rowdily waiting for a response. The mood from the chat was that people found this hilarious. Continuous streams of laughing emojis and eggplants flooded his un-moderated chat.

“well...” Another donation came through. This one had to be better.

$10-” pretend to suck a dick and I’ll donate $50. Do it really well and I’ll donate $200.

This was not better.

$1 came though right after from the same donator:

“2 minutes minimum and you have to enjoy it.”

After reading these aloud the chat was in uproar. Someone started posting the words “DO IT” which lead to nearly the entire chat filling with the same message. Every line was going so fast. Some were calling him a bitch and to just do it. Some said much worse things that he wish he hadn’t read, but it seemed like he wasn’t going to be able to move past this without something from his end. That much money was truly unbelievable. But could he really trust the word of a complete stranger? Everything about this sounded like a trick, but now people were threatening to permanently boycott and report the stream.

“But how can I know he’s legit!?” Andy asked the crowd (about twenty eight people now) “that’s so much money!”

The chat didn’t seem to care and continued to spam more messages.

$50 came through as a donation:

“okay here’s the 50. I promise you’ll get the rest after you do it. Now Dont be a pussy..”

The chat was now out of control. They weren’t going to stop until this really happened. And after taking $61 dollars from this guy already, Andy felt somewhat guilty. He felt the lipstick smudge on his lips and thought about what a beautiful young girl the viewers must be seeing right now. No wonder they’re getting excited, he’d probably want the girl to do it too. God it felt good to be making so much money. He’d be able to buy so many nice things for himself and his mother. Maybe he was getting himself getting a little too excited.

..

..

..

“Okay I’ll do it”

Pogchamps, and awed emoji faces burst into the chat. His phone barely kept up with how many were being recieved.

“You better not be leading us on you bitch” one person wrote. Wow, maybe he really should think about getting a moderator, Andy decided. He was so thrilled by the money and the viewers, and the money, that by now almost all the guilt of appearing female had faded away. But the sexual nature of this task still made him feel nervous. Could he pull this off for the two minutes that he’d now promised to the chat? Everyone was so worked up, he didn’t think he could let them down now.

He took one deep breath. Thought about how he looked in his mothers mirror. And thought about sucking.

CamcorderLenseCloseUp_Videvo_small.jpg

He stopped himself suddenly and thought that actually he should just turn everything off right now and stop being a freak. “This shouldn’t be happening at all”.

But for all of the money and friends.. Were these his friends now? He felt... so lucky.

He took a deep breath and thought about sucking..

He looked into the camera.

The cold black lens of the camera penetrated into his gaze.

cam lens deep.jpg

A gaze became a trance. So much was running through his head right now. Thoughts spun yet reason stood clear.

He opened his mouth slowly and pausing there, it hung.

He’d seen it all before, but never seen it done.

He slowly blinked his eyes, felt his tongue on lip

cam lens deep.jpg

Raised his hands, gently by his face.

His lips moved apart, his mind wandered. He’d seen so much porn before. Seeing girls explored in video. He couldn’t really couldn’t go through with this now could he?. The memory of a girl. A face he remembered. Actions played out in his head.

He imagined what would happen next, that her hands would move closer

She slowly closed her eyes, rolling them both up.

Her hands would touch around her mouth, her head adjusting carefully.

cam lens deep.jpg

He adjusted how he sat. moans and mouth sounds..

holding for a moment, she pulls both hands right back
–
He opened his eyes to look at his chat. He’d wandered off for a second again there.

The chat was screaming. More messages than he’d ever received were flowing now through his insignificant channel. He stopped his phone to read a couple, and saw their excitement, as if they were celebrating something incredible. Had something happened in the news while he zoned out? He thought.

He wasn’t even aware of the time but felt like he’d definitely missed out on something important.
His mind always wandered off when he didn’t want it to, but Andy was determined to understand what everyone was cheering about in this now rapid stream of messages.
All of a sudden, to answer just that, donations popped up on his screen.

The first were just as unhelpful as the rest of the chat but came with five or ten dollars each time.
His heart stopped completely, when he read the last one on his screen.
$50:” I cant believe it you beautiful babe. You actually went and did it you’re a whore.”
And there he realised what he’d just done.

–
hope you enjoyed.. ;)
new chapters are posted on my patreon twice a month (currently on ch7)
https://www.patreon.com/ramona_loveletter
all chapters will be eventually released for free, about once a month
I recently wrote a sexy pov halloween tale too..
please enjoy responsibly

mona x

Subgoal Sissy: Desperate streamer slowly becomes a girl pt.4

Author: 

  • ramona_loveletter

Audience Rating: 

  • Younger Audience (g/y)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Reluctant
  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Partial Transformations
  • Sissies

Other Keywords: 

  • streamer
  • streaming

Permission: 

  • Posted by author(s)

Subgoal Sissy: Desperate streamer slowly turns into a girl ch.4

Chapter 4

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(ps*I’ve been updating this story over at @https://www.patreon.com/ramona_loveletter
I just posted chapter 9, and there’s a saucy halloween tale there too ;)
I’ll post pt 5 here near xmas. x)

With a headache that thumped into his head like a spike, Andy pulled himself up and looked around for his phone. He couldn’t find it anywhere. He’d obviously made it to bed last night but couldn’t quite remember how he’d got there. Without his phone to comfort him with internet scrolling he had no choice but to spend the next twenty minutes lying there still, washing his mind of troubling feelings, letting his head spin and thinking about nothing. Eventually, when he found the energy to reach the edge of his bed, he paused again and looked around his unkept room.

Pieces of last night were slowly coming back. Before he could sort them apart, he made out the shape of his phone on his desk, probably dead. Empty of all energy, just like he normally was. This night, however, seemed to hold a thicker more impenetrable fog, to cloud his mind as to what transpired near the end. But soon, as he dug deeper, everything began to rematerialize. Last night had really happened. He threw himself back on his bed. Desperately, he tried to reject the vivid, flashing memories, none of which could be true.

Somehow he was still wearing his mom’s clothes.
A deep sigh broke his silence.
Andy, now with pieces of clarity blossoming, really didn’t want to think about what he’d done yesterday at all, but as he attempted to decide that it never really happened, he was struggling to let go of the truth that his lowly stream now had an attentive audience of dozens of real life people, and that he’d made more fans than he’d ever had before. He’d clearly gone too far of course, maybe lost his focus and ended up doing something embarrassing, but he remembered the amount of donations and this made him pleasantly warm.
But again in his joy, exhausted seeped back in, along with the fact that he couldn’t remember exactly what it was he’d specifically done when he’d zoned out near the end of his stream.

“fuck”.
He just really hoped that no one from his school had watched.

-

Today was yet another day of school and, bouncing up, Andy finally plugged his phone in to charge, quickly changed out from his mom’s clothes (he’d have to hide them until he knew how to get the creases out) and realised just how hungry he was (he hadn’t eaten last night at all). But before he could eat, he slowly crept out to the bathroom, careful to not be seen. This time he remembered how he probably looked with makeup on his face and that he should probably try to find some makeup wipes if he didn’t want to go to school in it again. But on walking through the doorway, he was taken back by the figure he found in the mirror which almost seemed, for a moment, almost too convincingly like a young cute girl.

b mirror.jpg

Andy shook this off quickly, but after wiping his face clean for the first time in two whole days, something different was stirring in him when he saw his face bare. Maybe this was just his stomach’s plea for help, he thought.

“Hey mom?” he called shortly after, sweeping downstairs onto the landing below. “Did you have an okay night?”

No one answered.

That was odd. She always made sure he was awake before she left. He tried looking for her around the rest of the house.

Something felt off now to Andy, but with all of his mixed emotions bothering him this morning he really had to get something to ea-

“Shit”. He saw the time on the clock.

Now leaving about fifteen seconds to grab one slice of bread, he knew he’d have to sprint to school once again. Immediately forgot about the fact that his mom hadn’t woken him up and was nowhere to be found, but very before long, he was off and out to try and save his school record once again.

-----

It was extremely close; his world class stupidity had almost made him late for school yet again. But nothing seemed unique about the day when he sat down at his desk, despite coming to school with makeup on the day before. But when he drifted off, as he normally did during the start of each class, he started feeling more and more paranoid as his account of yesterday again began to become clearer.
He couldn’t get it out of his head that he’d tricked multiple people into believing that he was a girl for money.

None of it seemed real. This wasn’t normal behaviour from a guy. Panic started to grow in him. Maybe something was actually wrong with hi-
“U- Uh yes miss?” Andy replied back to his teacher who’d sternly just asked him if he was still awake.
A few giggles travelled quickly around the class, causing Andy to turn red. But the class moved on strangely quickly, and Andy too was almost about to settle back down as well, but then suddenly, only so quiet that he was unsure if he’d instead imagined it, he caught from the corner of the room, a vile, jagged whisper: something carrying the word ‘girl’.
He couldn’t make out the rest of the words but he knew it was about him.

red classroom.png

-------
All of his troubles rushed straight towards his head. He was now more paranoid than at any time before. Every look in his direction now became a deep, probing, knowing interrogation. Every head that turned his way was now a careful attempt for any information that they could use against him. He couldn’t bear to look anywhere other than directly at the floor.
Andy scolded himself for being so gravely naive and forgetful; being so tired and just generally disorientated he’d forgotten how easily rumours can spread and that he still didn’t know how much his girlfriend had heard. She’d probably sent him hundreds of messages and here he was just being an idiot staring at the floor. It was suddenly crucial that he told her the truth as soon as possible, that it was all a misunderstanding, and that he wasn’t a freak. He reached for his phone in his pocket.
He reached again for his phone in his other pocket.
Unfortunately, in another painful moment, he happened to find that he’d stupidly left his phone at home, charging uselessly on his stupid desk. He wished he could disappear.
He knew that his only hope now was to find his girlfriend April as soon as he possibly could. She was normally quite elusive to him during school hours (and all non school hours to be honest), but If the rumours had reached her then he’d have probably completely lost his chance to explain his innocence or even talk to her ever again completely.
The lunch bell tolled and he sprinted out of the room.

Regardless of what was really said in the corner of that classroom a moment ago, Andy had absolutely made an even greater fool of himself with his frantic scene of suddenly jumping up and abandoning the class and with the way he raced through the school hiding his face with his hands. Several people who knew nothing about him (or his girl-scapades) were nearly rudely knocked out of his way.

-

Andy couldn’t stop thinking about the price he had willingly paid. He was unpopular for sure, but he wasn’t ready to become a school pariah. How could he have possibly thought that he’d gotten away with anything? People were glancing over at him from every angle; he tried telling himself that he was being overly paranoid. It didn’t help at all.
He decided right then that he’d gone way too far with all of this. He was happy with the money he’d made, but he wasn’t a girl, or a pervert or anything of the sort, and so he’d never try any of this ever again. It was all to great a risk to his livelihood. He was now almost at the lunch hall when abruptly from his path ahead, one boisterous looking boy started to come straight towards him in seemingly friendly applaud.

“Yooo, broo.. that was awesome!
You really tricked all those idiots last night!” Andy stopped completely, deer in the headlights.
”They actually thought you were a girl! Honestly that was sick as fuck bro, where did you think to do something like that? How much money did you make?”
Andy’s breathing had functionally stopped.

“No, seriously bro, I didn’t know you were this much of an entrepreneur! Are you doing it again tonight or uh.., what was your name again?..”

Ten seconds later, Andy sputtered a meek, vague, nervous half-sound.

“Danny!” Another guy, who Andy hadn’t noticed, claimed quite confidently. Someone reached over and was about to correct him. There was now a total of five boys (all larger than Andy) circled around him, all smiling and talking.

In a nervous, tiny laugh, Andy, struggling to absorb that this was in-fact all really happening to him right now, clumsily turned himself away from his interviewers and tried making off in whatever direction was opposite them. As it turned out, the pressure of his nerves had swelled his judgement and instead of escaping from danger, he soon found himself now further inside the crowds of gossiping students all heading for the lunch hall with the way back out being now blocked by his new admiring bros. How did they find him so soon? He stressed deeply, a thousand thoughts spinning in his head.
-

He shortly broke into an opening in the narrow mouth of the now roaring lunch hall. Hundreds gathered gossiping here in every direction. April could have been anywhere in the entire school in this moment, but in a rare moment of luck, to his unbelieving eyes, and like seeing distant land ashore in the wake a storm, Andy saw his April in the furthest far corner or the room, talking comfortably with her friends.

She seemed so peaceful in her own little bubble beyond all of the crowds. What he’d give to be in her shoes right now, he thought. He imagined going over and asking her about the party she’d been to the other day.

Andy tried to read their lips. He couldn’t figure anything out but their conversation seemed to be becoming very lively. And for Andy this meant that he was surely already too late to be able to explain himself and he was probably in for a very bad time. She’d made it clear to him on several occasions before that because he was so unpopular in school, he wasn’t allowed to talk to her when she was with her friends, with no exceptions. This was in-fact most of the time that she was in school, but Andy, with no clue of what else to do, simply just stood still where he was (in the way of people trying to enter the lunch room) and lost himself in his thoughts.

After the longest minute of his life, April effortlessly turned and looked his way and directly caught his eyes.
There could be no true reading of her mood in this moment. For all of the years he’d known her, Andy had no idea what these eyes meant. They locked eyes for what seemed like an hour. The room slowed down in it’s motion. Neither blinking, her face a blank slate as if daydreaming or simply looking straight through him, his surroundings had vanished to silence. He couldn't feel the people that were forcefully pushing their way past him into the room, he tried to convey to her with his eyes that he was sorry and that none of it was true.
In a final moment her glance turned sour, as if to say ‘who is that idiot stood there blocking the doorway?’ and, grimacing, she turned back to her food and continued laughing at whatever story her friends were telling her about.

A girl suddenly arrived, landing right by his left. “You should join the cheerleading squad you knowwwwww! All the boys would really love you. They’d tear you to shreds! Ha ha!”

Andy flinched round and saw a complete squad of preppy young girls addressing him en masse. About six altogether. He was completely submerged by excited smiles and questions all waiting for his response. One of them bluntly walked past, calling him a whore. Another trailed behind her advising him that “A girl really shouldn’t act that way at all. You’ll regret it in the future” followed by one gleeful girl cackling “you should be saving yourself for a good man you’ll marry one day babe” before beaming off into the crowds of the lunch hall, leaving him stunned. Andy knew he was truly screwed.

skrt.png

He quickly turned again to find which way he’d entered the room but the door was completely blocked with queues of people lining up for lunch. Several of them were staring strangely at him. Someone in the distance shouted “Girl!”. The room was now effervescent with conversations, but it really was clear that despite being all in their own bubbles, individuals from all around the room kept glancing at him as if he was weird. He had to get out, but with the growing assault of stress on him, he couldn’t find a path to choose. He instinctively dashed off towards the right side of the room. Everywhere was so crowded with bags and chairs the every route between tables had become a maze. The longer he stayed, he imagined the threat of him being confronted again. He kept finding himself in dead ends and corners and standing clueless in-front of bemused jocks and shit-starting girls. “Oh, were you going this way fag? Need to change a tampon?” A small group erupted with laughter. He was becoming increasingly lost in this growing sea of crowds. His heart was racing and his breath could barely keep up. But stumbling and tripping and fearing that everyone around him thought he was some kind of girly boy, he had no choice but to get out soon.
----

Finally after somehow passing through one of the room’s small side doors, Andy fell back against the wall and sighed so deeply, closing his eyes and dropping his bag on the floor. His ears were still ringing but Andy was now alone at last in en empty corridor.

“Hey dude. Look, I didn’t mean to scare you off before-” Andy was terrified.
“wait. Let me explain”
The group of ‘Bros’ from a few minutes ago were now once again standing beside him, completely from out of the blue, but still gasping to catch his breath, Andy simply decided to surrender to their interrogation. At least if he die right now, there’d be few witnesses in this hallway here, he consoled himself gravely.

“No, really!” Said another kid to his side.
“I’m looking forward to watching again.” They could see how Andy was distraught.
“You’re like pretty brave dude honestly, and it’s always cool to see someone from around this neighbourhood who’s not afraid to break traditional gender stereotypes.”

“...”

Andy, with no words left to speak, slowly waited for the punchline and looked one of the guys in the eyes. They really did carry a look of respect with them. This has to be a joke. He thought again and again and span around to look, checking that no one was else was around or filming him. He paused in anticipation one last time, but nothing else came.
Reassessing the situation, he calmed down greatly. All he managed to do was to mutter out a weak, barely audible “..thanks?”. He still wasn’t sure that they weren’t about to call him a sissy and beat him up.

“No problem bud, catch you later” The closest guy replied, and with a pat on his shoulder, off they went past him to go find a space in the hall.

“Oh, and uh..” the guy turned back to look at him before he left.
“you make a pretty hot chick”
He laughed to one of his friends warmly and strolled off back down the hallway.

Andy’s body flushed with goosebumps. He stayed in the empty corridor to reflect. First it felt wrong and he couldn’t stop blushing, but then he realised that from just those four guys, this was in fact the most successful social interaction he’d ever had at this school. His ears had stopped ringing too. He wasn’t sure if he’d felt this before from any other people his age, but it kind of felt, amazing. And so, without his consent, the coals were again stoked back into his motivation for potentially continuing his streams. He really did need to find somewhere quieter though; all of this and the night before had exhausted him to the point where he didn’t think he couldn’t manage another person.

-

Two hours later, Andy found himself in the last class of the day, a quiet physics lesson. Nothing interesting could happen here, he confidently assured himself. Shortly after taking his seat however, the teacher began revealing the plan for the final hour: students were to split into pairs and follow a precise set of instructions to test the tensile strength of narrow sheets of wood. ‘Incredible, Andy thought. ‘When am I ever gonna need this in life?’. He’d been struggling with the urge to just leave and go home, but with his poor record he knew that this wasn’t really an option. Everyone around him seemed to be getting out of their chairs and shuffling around though, as he was debating these new thoughts.

Before he could fully focus again, the class had already split into pairs for the experiments. “Fantastic” Andy thought. Surely there wouldn’t be enough people to find a partner and he’d be able to sit this one out. Unfortunately for Andy, as the students moved back to their new seats, a strange kid was left standing next to the teacher, looking awkwardly around.

“Oh great” The teacher said. “It looks like Andy doesn’t have a partner yet. You wont mind going with Joshua will you?”. Andy’s response clearly wasn’t needed as the teacher immediately went into a presentation explaining the first steps of the experiment to the class. Joshua was now sitting beside him, looking at him curiously.

“Hah, I always get picked last for these things” Joshua laughed to Andy. He’d had never spoken to him before but knew that Joshua was about as unpopular as himself in the school. There wasn’t anything really wrong with him exactly, but he was just maybe a bit too interested in studying to really attract any friends.

All throughout the teacher’s demo, Joshua seemed to be moving around in his chair almost a little too much, and Andy, still inexperienced in being sociable, was unable to respond to his repeated attempts at making conversation. All Andy could do was pretend to be paying attention to the teacher. He still didn’t know who knew about his him pretending to be a girl, and thought it best to just keep talking to a minimum.

The teachers task sounded simple. One partner was to hold up a series of square wooden panels while the other was to use both hands to push against them until they broke. (*this does go somewhere I promise ;)- author ramona*) Starting from the center-point of the wood, the students were to horizontally move their hands further apart on each attempt and then record how difficult it was to break the square from each of the spots on the shape.

Andy was dreading this whole task and would much rather have done a test in silence. But Joshua for some reason seemed like he’d just been given the opportunity to make a new friend.

Joshua thought it would be a great idea for Andy to be the one to hold up the squares and so Andy slowly picked up the first at it’s corners and held it at arms length. He couldn’t help but notice just how thin his arms had become lately, not much muscle for a guy. But before Andy was ready, Joshua had broken straight through the middle, and quickly started laughing.

“what the hell Joshua?” Andy spluttered out.
“Oh so you can talk, hey?, Joshua turned to write down the first results.
“You can call me Josh though. Are you always this shy?”
This was a stupid question, Andy literally never spoke to anyone in school.

Before Andy could find a response, Josh had jumped back up and started pushing against Andy’s second panel. Each time a square broke Josh would more his hands further and further away from the center of the wood, and with each new square, Josh had to push harder and harder to break through the middle. Now apart from running to school, Andy didn’t exercise at all and always forgot to eat proper meals, so what was at first a seemingly trivial task, grew to become increasingly challenging. He ended up having to put more than a modest amount of effort into holding each square back against the pushes from Josh’s offensive. Most of the girls in this class were probably stronger than he was, he thought.

Andy looked around to see that the rest of the class had become unruly, with people laughing at each other, some now lying on the floor, and more than the expected few trying to imitate karate masters. But From all of the constant talking Josh had been doing, It suddenly struck him through his paranoid barrier, that Josh was trying to be his friend.

He almost couldn’t believe it. It wasn’t until after this and several attempts of Josh asking him if he had any plans this weekend that Andy realised that he legitimately couldn’t remember the last time someone had tried to make a friend out of him. “uhhm, not much really. Maybe some video games” Andy quietly replied, finally breaking his silence, and bracing against the next incoming push. “Niiiice” Josh replied. And from here, Andy’s irritation at the boring group task, slowly started to turn more pleasant. “Is this how normal people make friends? I guess we do have a few things in common” he thought. “why hasn’t he ever tried talking to me before though?”

All this seemed to soothe the thoughts in his mind. This new idea of friendship was starting to spread through his thoughts with a warming feeling, pushing his anxiety away.

“You know what? I didn’t know you were this strong” Josh said. “But can we break this one?” Andy was straining with all his might to keep this square straight, and Josh was almost breaking a sweat trying to push through. Both had their legs in secure stances, but Andy, looking at Josh’s smiling face, began to think that maybe some things can’t be broken.

Both were hot, straining, and now almost sweating. Half of the class had given up at this point. Perhaps the teacher was having some fun with them and had given out an impossible end to the task. Andy moved his feet again to regain his best position and noticed the way Josh was now looking at him. It almost reminded him of the way that his girlfriend had looked at him one time long ago. But it was such a vague feeling he didn’t know if- Blam.

board break.png

The board split through and Josh shot towards him. Andy, unprepared, was jolted after putting all of his weight against this square. As boring of an experiment the teacher made this sound, both their hearts were racing as Josh now flew towards Andy at a rate that neither were anticipating and both of them collided in each other’s open arms. This wouldn’t have been so bad if it wasn’t for the fact that Andy had left a chair a little too close to the back of one of his legs. Immediately he lost most of his balance. Andy held tight and embraced Josh for dear life, looked directly into his eyes, felt his arms around his torso, their chests pressing together and his weight falling on top of him.
-
As Andy lay on the floor, he looked up into the eyes that were directly in front of him in and, in silence, feared the possibility that he’d broken something bad. Josh still had that friendly look in his eyes. Staring deeper he could almost feel a deep warmth inside himself, as though his worried soul was being soothed through all of the pain. As he lay there on top of him, looking down into him, they weirdly seemed to be safe and didn’t feel the need to speak any words. Josh moved in for a kiss.

“No no no no no no no!” Andy squirmed and shuffled his way back out from under him, bumping the chair-legs. He looked around to see if anyone had seen them. Nothing. Everyone was actually already packing up and getting ready to leave the class. He quickly stood up and looked back at Josh sitting on the floor and without saying anything packed up his things and moved away. Once the bell rang, Andy promptly left. Before the hallway however, he stopped to glance one look back at Josh but couldn’t find him anywhere. He had to go home.

-----

-----

“Hi mom I’m home” Andy called out.

“Oh, good sweetie” He heard in reply as he came into the kitchen.
His mom was sat at the counter, head down, and looked like she’d been crying. He cautiously rushed up to her and put his hands on her shoulder.

“Mom what’s wrong? I-” Was all he managed to get out before his mother said “I, I’m just a little fluey that’s all. D-Don’t worry. I’m. Just tired, and need some rest. Don’t worry about me honey, just go upstairs and I’ll have dinner ready later okay?” While she spoke, she didn’t take her eyes off the papers on of the counter in front of her. A few moments of deliberation later, Andy came to the conclusion that he didn’t know how any ways to help her right now, but he was relieved to see her home again. He backed up and went upstairs. Whatever it was, he told himself, surely she’d be able to figure it out by herself..

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hope you enjoyed.. ;)
new chapters are posted on my patreon twice a month (currently on ch9)
https://www.patreon.com/ramona_loveletter
all chapters will be eventually released for free, about once a month
I recently wrote a sexy pov halloween tale too..
please enjoy responsibly

~mona x


Source URL:https://bigclosetr.us/topshelf/book-page/95245/ramonaloveletter