An Unexpected Adventure with Robin and Olivia The Complete Story
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Exploring Olivia Ch.1-2 free porn video
Chapter One:
It was August 10th, the night before I was set to move into my new home
for the school year at the prestigious Coastal Shores Academy, and - just
like most incoming seniors around the country - I was stuck in my room,
finishing the holiday homework that I'd put off all summer to play video
games and hang around the house.
For most students, this would have meant a terrible night of solving
complicated algebraic equations, writing computer code, or memorising
important dates throughout American history. For me, it meant sitting at
my computer and writing a personal essay, simply titled: 'What Hollywood
gets wrong about the Current High School Experience.'
The voice of my father loomed over me as I wrote: 'This needs to be some
of your best work, Oliver, you're on a scholarship, your teachers will be
expecting a certain standard of quality from you, you need to exceed it.'
I'm sure that he felt at least a little guilty for my predicament, after
all, he was the reason I was coming to the school in the first place.
Similar to the way people from all over the world entered the United
States immigration Green-Card Lottery in the hopes of building a better
life for themselves; students from all over the continental US entered
the Coastal Shores Academy Scholarship Lottery with the hope of receiving
an education that wasn't just reserved for the rich, but the absolutely-
filthy-fucking-rich; the kinds of families that could spend a quarter-of-
a-million dollars on their children's schooling and not even notice that
it was gone. My father - without my knowledge - had entered the lottery
on my behalf, something he had neglected to tell me until I'd been
announced a winner. Once the announcement was made there was no debate, I
was to be the newest scholarship student at CSA.
There was a grinding sound from my desk on the other side of the room as
the printer churned out my finished essay. I grabbed the paper while it
was still warm, reading the first few lines to make sure I hadn't made
any obvious errors:
Hollywood has never been about portraying an actualised reality, instead,
it interests lay with presenting a fictional world just close enough to
our own to be familiar. However, as the world has evolved, the
stereotypical depiction of high school has not. 'Jocks' still bully
'Nerds' for liking Dungeons and Dragons, the 'Head Cheerleader' is only
interested in dating 'The Quarterback' and there are clean lines drawn
between the 'Good Guys' and the 'Bad Guys' at school. This could not be
further from the truth. A 'Nerd' is as likely to have Superman himself
show up on the school ground and make fun of him for liking superheroes
as he is to be bullied by a 'Jock' for it. The 'Head Cheerleader' is
dating whomever they are attracted too, and there are no 'Good' or 'Bad'
guys, just a bunch of people, who - although complicated - are just
trying to get into a good school so they have a chance to lead a life
better than their parents.
It was about as straight down the middle as an essay could be. Detached
from any real emotion, but possessing enough bite to let the reader know
I had at least some interest in the topic; not as dry as a scientific
essay, but intellectual enough that I wouldn't appear daft. It occurred
to me that writing an essay for a class you've never attended was similar
to the plight that a bride and groom share when writing their vows after
having promised not to share them until the wedding ceremony. There would
be nothing more jarring than one person having a painfully different
candour in their writing to the other - or others, in my case.
Placing the paper on the desk next to the printer, I began to cross the
room, and although the trip was brief, I still managed to stub my toe,
hard, on the half-packed suitcase laying open on the floor.
"Fuck!" I yelled, tilting my head towards the sky in an expression of
rage. "Ow."
"All good?" my father yelled from the living room. I imagined him sitting
in his chair, watching whatever shitty comedy he'd found on Netflix,
having a quick chuckle at my display.
"Fine," I yelled back.
The suitcase had sat half-packed on my bedroom floor since I got the
offer letter to Coastal Shores, it wasn't that I was lazy, I swear. I
just couldn't look at the suitcase and not be reminded of the fraudulent
nature of my acceptance. Not the one-hundred percent legal fraudulence of
my application, but my acceptance to such an elite academy. There was
nothing about me that was elite. In fact, I felt confident saying that I
was remarkably ordinary. I wasn't tall, or handsome, or talented or
particularly intelligent; neither was I short, or ugly, or particularly
unintelligent. In a school full of the uber rich, the outrageously
talented, and the incomprehensibly intelligent, there could be nothing
worse than that.
I thought better of informing the suitcase of my disdain via a kick. If
it were capable of feeling things, however, I was sure that it would have
felt remorse after the intense glare I gave it.
There was a sharp chime from my laptop that shook me from the tendrils of
my mind. I read from the screen:
JB: Did you know that a recent surgeon general of the United States
believes that our generation is suffering from what they call a
'loneliness epidemic'
I felt that I knew much more about the loneliness epidemic than my online
friend, JohnnyBravo2112 - or JB, as he appeared on my screen - could
comprehend. It had been loneliness that had led me to anonymous chat
rooms, and desperation that had led me to create the profile he was
currently messaging.
JB: Britain even has a 'Loneliness Minister', like a member of parliament
that is specifically dedicated to the effects of loneliness on the public
health. Isn't that insane?
I sat on my bed and stared at my computer for a few more moments, waiting
for the inevitable third message that would finish his thought.
JB: Olivia, are you there?
Before you ask, he hadn't made a mistake. JohnnyBravo2112 was, at that
moment, doing something that every person who has ever used the internet
has done at least once: Talking to someone who was not who they said they
were.
Like most of my peers, I, Oliver Green, had an undiagnosed social anxiety
issue. While most people thought that my lack of socialisation was due to
a quiet personality or shyness, the truth was, the idea of contributing
to a conversation with people I wasn't close with terrified me. It didn't
require much of a leap in logic to understand why I did not have many
friends. People assumed that because I never vocalised my issues making
friends I was perfectly content, a true introvert, but too often at night
I would find myself desperately lonely; and - as I'm sure JB was
preparing to eloquently inform me - loneliness was just as bad for your
health as smoking fifteen cigarettes a day.
So, I began browsing chat rooms; and, for a while, that was enough. But
chat rooms are filled with teenage boys, and most teenage boys have no
interest in talking to other teenage boys. They want to talk to girls.
So, I'd created a new profile: ExploringOlivia.
For the first time in my life, I was overjoyed that my face was
predominately androgynous, it allowed the editing software to feminize it
without making it look fake, I'd painstakingly used photoshop to give
myself long, golden-blonde hair; I'd even changed my eyes to an emerald
green, to match my last name. If someone I knew were to stumble across
Olivia's avatar, or the photos on her profile - including full body
photos that I'd obtained with an assist from a former babysitter who was
truly awful at English literature - they might think that they'd stumbled
upon one of my distant relations. Most likely though, they'd never make
the connection, after all Olivia was unforgettable, where I was
unrememberable.
It had not taken long for the messages to begin flooding my inbox. For
every 'hi, how are you?' I had received ten 'send nudes', and for every
'I love your smile' I received five 'I'd love to see your lips wrapped
around my dick.' Needless to say I chose who I spoke to carefully.
EO: That's pretty crazy! It's so weird that we're lonelier now than we
have ever been, even though we can talk to so many more people now! Lol.
JB: I feel a lot less lonely when I'm talking to you.
When JB said things like that, it made me feel a level of guilt that I
had not been prepared for when I'd begun this experiment. I'd thought so
often about telling him the truth, that I was just another lonely guy
looking for a friend, but it had gone too far.
JB: What are you wearing?
I sighed.
When we had started speaking, JB had been the perfect gentleman, we'd
talked about sports, and school, and movies and shows we were watching on
Netflix; he'd confided in me about girls and I'd also confided in him
about girls, sometimes going so far as to confide in him about boys - who
were really just the girls I'd already been telling him about, but
gender-swapped. It wasn't until we started talking about video games that
our relationship changed. Most of what I told him was the truth: I loved
gaming, but we didn't have the money for all of the new consoles and
titles and so I mainly just played old N64 games. He had reacted with
such dismay that I could have sworn he was offended by my poverty. He
offered to buy me a game, one that we could play together that would run
on my school issued laptop, but, as a gaming chemistry test, he wanted to
play another game with me beforehand: 'Truth'.
And, in a moment of terror, I imagined all the possible things he could
know about me. Has he doxed me? I asked myself. Would he go so far as to
tell everyone at my school that I pretend to be a girl in chat rooms. I
decided to be brave, after all, it was better to know what he knows than
to just face the consequences of it, maybe I would be able to explain
myself. So, I agreed:
JB: Are you a virgin?
EO: That's kind of personal, isn't it?
JB: That's why the game is called truths.
And maybe I was still worried that he was pulling a long con, or maybe I
just enjoyed the thrill of it, but I began to play along.
EO: Yes, I am still a virgin.
JB: Why haven't you had sex yet?
EO: Haven't had the opportunity.
JB: That's a lie, look at you, you've had an inordinate number of
opportunities.
I knew he wouldn't believe that, I had only said it to give myself time
to look up statistics for my real answer:
EO: My family is religious, they don't believe in sex before marriage.
So, my father won't let me go on birth control, and I'm allergic to
latex, so no condoms either. There is a four percent chance that I could
get pregnant even if we execute the pull-out method perfectly, I don't
like those odds, and I haven't met anyone I like enough to let them stick
it in my butt.
If this was a test to determine if I was faking, I had to do a
particularly good job of convincing him I wasn't. Once he was convinced I
was telling the truth I could wean myself away from him naturally, until
I would no longer risk exposing myself and the repercussions that came
with it.
JB: What's your favourite cut of underwear?
EO: I wear thongs, pretty much every day. Except when I'm on my period,
then it's granny panties all the way. Lol
I had convinced myself that the best way to get him to stop doubting me
was to turn him on - after all, no self-respecting straight guy was ever
going to want to admit that they were jerking it to another guy, even if
he was pretending to be a girl. And whilst the idea that an anonymous on
the internet was going to be jerking off to a feminised version of me was
kind of weird, it was much better to the alternative.
JB: Bra size?
EO: I'm a B-cup, as in barely any. My butt more than makes up for it
though, it's pretty nice if I do say so myself.
JB: Do you finger yourself?
EO: What are you really asking, like, do I actually finger myself or do I
masturbate? Because those are two very different questions.
JB: Both.
EO: Okay then. I masturbate more than I'd like to admit, definitely
daily, if not twice a day. In fact, I've been known to get pretty moody
if I don't cum at least once a day. As for fingering myself, not so much,
most of the time I prefer clitoral stuff, but sometimes you just need
something inside you. So, sometimes, I guess.
I had waited for a few moments for a response that was taking longer than
I would expect from JB, so I added:
EO: I'm calling game. After all, there has to be some questions left
unanswered if there is to be a potential sequel, can't go giving away all
my secrets now, can I?
And if JB had ever doubted my validity as a real girl, he never would
again.
Another chime from my computer bought me back to the real world:
JB: You're not mad, are you?
Having indicated to him that I was online through my first response, I
knew if I didn't keep up the conversation he was just going to apologise
for whatever reason he had decided I might be mad at him for, I didn't
want to wake up to sixty unread messages in the morning, so I responded:
EO: I'm wearing comfy socks, yoga pants and a hoodie, pretty much all of
my other clothes - aside from my pyjamas for tonight - are packed away. I
move to my new school tomorrow.
JB: That's kind of boring. I was hoping for something a little more than
PG-13.
JB: How are you feeling about the move?
EO: Sorry to disappoint, lol.
EO: Nervous, I guess. It seems to be really different to my old one.
JB: I'm not trying to minimize your problems or anything, but you'll be
fine, you're super hot, everyone will want to be friends with you.
And part of me wanted to open up to JB, to tell him all about how I felt
that there'd been some mistake, and that I was being sent to Coastal
Shores as some sort of cosmic practical joke that everyone was in on
except for me. But, it seemed a little on-the-nose to bring up my
imposter syndrome given the circumstances in which JB and I were talking.
It was times like these that I wished I had real friends.
JB: Are you still there?
It occurred to me that maybe I should have taken people more seriously
when they told me that they'd read my message and just forgotten to
reply, considering I had done that to JB at least three times in our
short conversation.
JB: Did you know that it is now, officially, your birthday where I am on
the East Coast?
Thankfully, this allowed me an excuse to get out of the conversation.
EO: Yeah, my dad and I are about to go out for dessert. It's kind of like
I'm a death-row inmate, being given my final meal before being taken to
the chair.
JB: School isn't going to be that bad. What are you going to wish for
when you blow out the candles?
EO: I don't even think I'm having a cake, honestly.
JB: You can't have a birthday without making a wish!
A cupcake appeared on my screen, 'MAKE A WISH' written in bold lettering
drawn to look like frosting underneath.
JB: I don't know if an online blowing out the candles has the same wish
granting capabilities as an IRL one, but it's worth a try isn't it?
Although he sometimes crossed the border to 'Creepy Weirdo', I had to
admit that for the most part JB was a genuinely nice guy. I pondered what
to reply for a second, truthfully, there was an inordinate number of
things that I could wish for: To not have to go to a new school for my
senior year; or to have enough money that I didn't have to rely on the
charity of others; or even that I was better looking, or smarter, or
anything remarkable. But, as I stared at the candle flickering on the
screen, all I could think about was the guilt that consumed me every time
the name 'JohnnyBravo2112' announced itself with that sharp chime. And
the words formed themselves in my mind: I wish I didn't have to lie
anymore.
The flame at the top of the candle was extinguished with a single click
of my mouse.
JB: I know you can't tell me what you wished for, but, whatever it is, I
hope it comes true.
EO: My Dad is calling, apparently it's time to go.
JB: Will we be able to talk while you're at school?
EO: I don't know, but we will on weekends.
JB: 'Til next weekend, I guess.
EO: Goodnight, JB.
My father had never purchased a cell phone, he was convinced that having
the world be so accessible to you at all times did nothing except mess
you up in the long term. As I lay my head on my pillow and closed my
eyes, I wondered if he was right. After all, when anyone could reach us
at any time, could we ever really shut off? Was that the reason that I
always felt so tired when I woke up? Was that the reason I couldn't stay
asleep through the night? A more troubling thought occurred to me: You're
being punished for your sins.
I hadn't been lying when I'd told JB that my father was religious,
although, he wasn't the typical say-grace-before-dinner, go-to-church-on-
Sundays type of religious. He believed that the bible contained important
messages, morals to live life by, rather than a completely factual
account of life in the BCE. He also believed that people disregarded the
messages of the bible at their own peril, that sinners would be punished.
The idea that my punishment was coming terrified me.
I took the cocktail of cold and flu tablets that guaranteed me at least a
half decent night sleep. Somewhere, in the deep recesses of my mind, two
distinct voices in my brain argued about whether the long-term effects of
not sleeping would be worse than the long-term effects of the Benadryl
cocktail. But, as happened every night, I was asleep before they could
disclose the answer.
Chapter Two:
The only times I managed to sleep through the night were when I was
either sick, or so deeply exhausted that I was certain to lose the same
amount of productivity that I would have if I were sick. When I woke up
on the morning of my eighteenth birthday, about eight hours after I had
fallen asleep the night before, I was not sick. Nor was I the type of
exhausted that would preclude me from being a productive member of
society. Instead, I awoke feeling sheer dread, as if something were
indisputably, and irreversibly wrong.
I opened my eyes.
I was in a bedroom - which wasn't weird in itself - but it was a bedroom
that was entirely unfamiliar to me. I was lying on my stomach - something
that was weird in itself - staring at a wall completely empty of the
posters that adorned my own. No longer was I watched over by an original
poster for the theatrical release of Silence of the Lambs, nor was Han
Solo pointing his blaster at me from a Han Shot First decal I'd bought
off Redbubble. There's no way Dad pulled my posters down, I would have
heard him.
I swung my legs over the side of the bed and sat up. Ribbons of treasure-
gold hair cascaded on either side of my face.
What the fuck?
I pulled my hands up and looped my fingers through the strands of hair.
Collecting myself, I gave them a quick tug. Instantaneously I was greeted
with a sharp pain in my scalp.
What the fuck, what the fuck?
I allowed my hands to traverse my face, but neither the hands nor the
face felt like the ones I knew so well.
I glanced down.
I was wearing a shirt, a loose-fitting purple tank top, one that I did
not remember owning, let alone wearing to bed - I don't even wear a shirt
to bed, not in the Summer! However, my surprise at the shirt was nothing
compared to the shock of the two small mountains of flesh attached to my
chest.
This couldn't be real, right? It had to be a dream didn't it, some kind
of trick?
My eyes scanned the room for anything familiar. Instead, they found a
mirror, as the final remnants of sleep left my eyes, and my vision
cleared, I was left gazing at my reflection.
I was Olivia. The spitting image of the photos I'd posted to my
ExploringOlivia profile. The female avatar I had created for myself to
find some fucking human connection.
This couldn't be real.
My first instinct was to run, and in enacting that instinct, I stubbed my
toe, hard, against the dresser. I yelped - out of Olivia's mouth - and it
was easily the girliest fucking sound that I had ever made in my entire
life, in fact, it may have been the girliest sound anyone had ever made
in their entire fucking life.
There was a rush of noise in the hallway, and moments later the door to
this - my? - room swung open. "Olivia, are you alright?" My father
stated, puffing for air. Then, almost immediately after, "Oh my god, I'm
sorry, you're getting dressed," he retreated behind the door, pulling it
until it was barely ajar. "Are you okay?" He asked again, the door
separating us from one another's view.
"I stubbed my toe," I said, my voice seeming less girly than before, but
still significantly more girly than I could have imagined twenty-four
hours ago.
"Right," he said, "sorry, again."
And he left without waiting for my response. It had all happened so
quickly that I hadn't even had the chance to look at his face, to see if
he'd been changed too, or if I was alone.
But he had called me Olivia.
There was a sharp chime from the other side of the room, enough to rouse
me from my state of utter confusion, and as I looked past the twin
mountains of flesh on my chest for the first time, I realised what my dad
was so apologetic for when he'd burst through the door.
I wasn't wearing any pants.
Only a pair of lace black panties with such little material that - from
his perspective from the other side of the room - my father may have
thought I wasn't wearing anything at all. They fit tight over the curves
of my new hips, hugged my pelvis tight - evidencing something every male
in history is terrified of waking up to discover, the absence of bulge -
and disappeared into my butt-crack.
I'm wearing a thong. I am in a girl's body, a girl that doesn't exist,
and I'm wearing a thong.
Considering this was my first time wearing a thong, I was surprised at
how little I felt the string running between my cheeks. In fact, I barely
even noticed it was there.
There was another chime from across the room, and this time, I saw an
accompanying flash from my laptop, sitting open upon the desk.
My toe still aching from my previous mishap, I was careful as I crossed
the room. The notification box at the corner of the screen indicated that
I had multiple unread messages. I sat on the bed, pulled the computer
onto my lap and read:
JB: I don't know if you'll get this before you leave, but I just wanted
to say good luck. You're going to be fine.
I couldn't even comprehend the idea of responding to him now, just
looking at his message made my heart pound and my head ache.
Could JB have done this?
I considered the possibilities:
1) JB is some kind of witch, and he decided that this was the best way to
punish me for lying to him, or, maybe he's mistakenly being benevolent
and believes that I was pretending to be a girl online because I really
wanted to be a girl, and this is his attempt to give me what he thinks I
want - although, this would still require JB to be some kind of witch.
2) There is a God, and he is punishing me for my sins, just like my
father said that he would. I have lied, and committed fraud, and now I
was being forced to live out this life as punishment.
3) I was having a full mental breakdown and none of this was real.
At the moment, the third option seemed the most likely.
"Olivia, hurry up, we have to go!"
As much as I would have liked to stay in bed all day and pretend that
this wasn't happening, I knew that wasn't an option. In fact, I was sure
that by not responding to him I was risking another my-dad-walks-in-on-
my-wearing-nothing-but-a-thong situation, and no-one wanted that. So, I
traversed the room searching for something to wear.
With the initial shock of waking up wearing off, I began to understand
more about the body I inhabited as I traversed the room. First off, the
mechanics of movement were very different in this shorter, curvier, more
hip-y body. In the absence of a bra, my breasts moved counter to my body,
most notably when I bent down to pull a pair of baggy sweatpants over my
legs. I suppose I should have anticipated the difficulty of putting on a
bra, considering my lack of experience with women's undergarments.
However, I found the entire exercise of putting a bra frustrating to the
point that I almost considered going braless until I saw my nipples
poking through my shirt in the mirror. I threw away the bra I'd been
struggling with and found one that clasped in the front, something I
found significantly easier to manage. I pulled a plain crimson t-shirt
over my head and slid my feet into a pair of Nikes.
I collected my laptop and opened my bedroom door.
My father had been standing in the hallway outside, waiting for me to be
ready to leave, he collected my suitcase and began walking the hallway
towards the garage. I followed, and although the desire to get out of the
house was overwhelming, I found my gaze drifting to the photos on the
wall. A golden-haired girl of no older than ten beamed at the camera
while holding a lightsaber as green as her eyes; the same girl, a little
older wearing a purple and orange cheer outfit; a girl that looked almost
exactly like the one I'd seen in the mirror, at Disney World, sipping a
fruity drink.
I hadn't realised when looking at the photos I'd edited for her profile,
but Olivia was a much better amalgamation of my parents than I'd ever
been. It was as if she'd inherited each of their best features: the soft
jaw and long eyelashes of my mother, the strong cheekbones and full lips
of my father - all of which she had grown into better than I ever could
have. But as I walked, my gaze consistently centred on her eyes, wide and
expressive, so green that if they were emeralds they'd have been worth a
lifetime of wages.
"I know you zoomers love looking at yourselves, but you're going to be
late if you don't get your butt out the door right now," said the excited
tone of my father. Even now, when he was stewing in my disregard for the
urgency of my leaving, his voice came out with more love than I'd ever
been exposed too.
I took one last look at the photos, and before I could stop myself, the
voice inside my head - the one that still sounded like the me I was
accustomed too - said: I don't remember the last time I saw dad so happy.
Haven
- 04.10.2022
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