[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

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

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.

“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.

-

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.

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.

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

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.

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