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A shy nerd takes on tutoring a popular jock.
In return the jock is to teach how to score with a girl.
Hey, when you want to learn an important lesson, you study
and complete the role play, right?

Study Buddies
Story Info
A shy nerd takes on tutoring a popular jock.
17.9k words
4.8454.1k24029
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georgiapeech
georgiapeech
4 Stories134 Followers
I've been working on several different stories at once, and just
finished this one, which is one of three I'm working on about being
feminized. Hopefully more to follow soon. Standard disclaimer, all
characters portrayed are age 18 years or older.

**********************************************

THWAP! The towel snapped against my bare ass cheek like a firecracker.

"Ouch!" I yelped in a surprised, shrill tone. I instinctively placed my
hand against the spot where I felt the sharp pain, I could still feel my
fleshy right ass cheek still jiggling from the impact.

I glared up at the three members of the varsity baseball team who had
just come into the locker room to find me changing after gym class. One
of them still clutched a gym towel in his hand like a whip. As they
laughed and ogled my naked rump, I quickly finished pulling up my boxer
shorts and jeans.

"Damn, Casey!" The oaf with the towel said. "Not only do you look like a
girl, you sound like one too!"

This elicited a fresh round of laughter from the three of them. It
always did, ever since freshman year when Billy Douglass -- then a
popular sophomore on the football team -- came into the locker room
after gym and remarked loud enough for every other guy in class to hear
that I had a "bangin' ass."

Now, I was a senior, and after four years of being made fun of by the
jocks about my admittedly girlish figure, graduation could not come
quick enough. Three more weeks, I muttered under my breath as I zipped
up my jeans.

"Hey!" A fourth, familiar, voice came shouting into the locker room.
"Leave Casey alone."

That was when I caught the eye of Derek Taylor as he marched into the
locker room. Like me, Derek was a senior, and we grew up a few houses
down from each other. Unfortunately, the list similarities ended there.

A quick way to describe Derek would be to say that he was everything
that I was not. Captain of the baseball team, he was tall, a few inches
over six feet, and had the type of ripped, muscular build that girls and
moms alike must picture in their minds when they masturbate. Suffice to
say, he had no problem getting laid, or so I'd heard. It seemed like he
was talking to a new girl every week.

"Sorry about them, Casey." Derek said as he walked towards me. "They're
animals."

As he passed behind me, he put a hand on my shoulder and gave it a
gentle squeeze. It was a familiar gesture, he'd done it a dozen times
over the years in situations just like this, when he'd walked into the
locker room or the lunch room and found someone picking on me. He'd tell
whoever it was to back off -- which was generally enough -- and then
he'd give me a possessive squeeze on the shoulder as if to say 'he's
mine, don't fuck with him.'

Derek and I weren't friends, really, but he'd always been nice to me and
he always stuck up for me. Like most high schools, bullying was
commonplace at ours, and I was commonly the recipient of it.

Sometimes they teased me about my size, at 5'5" tall and 130 lbs I was
one of the smallest kids in school. Other times, they teased me about
being a nerd; aside from having a perfect GPA I was also on the debate
team, the math team, and the chess team. Most of the time, however, they
teased me about the same thing those three assholes cackled about after
whipping me with a towel.

I have a...I guess some might say...thick ass. I don't just mean that I
have some junk in the trunk. Beyond the bare minimum of physical fitness
required to pass gym class, my workout regimen was non existent, so, yes
I did have some junk in my trunk. But it was more my... I guess you'd
call it my shapeliness that caught the attention of the bullies and jocks.

As much as I tried to hide it by wearing intentionally large and baggy
jeans and t-shirts, I had a perfectly round, thick, pear-shaped butt
that most girls would be jealous of. Also, I was scrawny up top and
slender at the waist, giving me the appearance of lady-like hips.
Finally, I had practically zero natural body hair except for my pubes
and a fine, almost invisible coat of hair on my legs and chest.

Ever since I made that first freshman-year mistake of stripping down for
gym in front of Billy Douglass, my ass had gotten me plenty of
attention. Unfortunately, it was the exact opposite kind of attention I
desperately wanted. It was perhaps my greatest disappointment that
addition to being an effeminate nerd loser, I was also a virgin.

And I don't just mean that in the strictest sense of the word. The truth
was, I was a high school senior, three months past my 18th birthday, who
had never so much as kissed a girl. It's not that I wasn't into girls, I
very much was. I'd spent lots of time thinking about girls, had a few
crushes, and even once came close to kissing Becky Stevenson before I
panicked and walked away. Alas, the only lover I'd known in my life was
my own right hand.

Everything would be different in college, I told myself. Once I got to
the big State University -- where I'd gotten a full-ride academic
scholarship -- with an almost infinitely larger student body, I would
find somewhere to fit in. I would find something to be popular for. And,
most importantly, I would find someone to fuck me.

Two more weeks, I muttered under my breath as Derek and the other three
jocks left me alone in the locker room. Only two weeks of school left,
and then I was off to be the man I was meant to be.

_______________________________________

"What a bunch of jerks." Scott huffed as we sat across from one another
at the lunch table later that day.

Scott Connors was my best friend. Well... he was kind of my only friend.
I met Scott freshman year on the first day of Chess Club and we hit it
off pretty much immediately. Kindred spirits, Scott and I were two
hopeless nerds desperate for female attention.

Though he was also a massive brain like me, Scott looked more like a
wrestler or a football player. He was taller than me, which isn't saying
much, just under 6'. He was also heavier. When we met, Scott was a
full-on pudgy kid, but in the past few years he'd taken up going to the
gym and managed to thin out a bit and now only carried a few extra
pounds around his mid-section.

"I've been trying to get you to come work out with me." Scott said,
taking a bite of his sandwich. I had just described my humiliating
encounter in the locker room.

"Why?" I asked. "It's not like I'm going to bulk up instantly and be
able to defend myself."

"True." Scott shrugged. "But if you put on some muscle you might look a
little less like a girl."

"Once we're at college it won't matter." I assured Scott. "The
university is huge, there will be no shortage of women for us."

Like me, Scott had also gotten a scholarship at the state university. In
fact, we'd gotten our acceptance letters on the same day and had made it
the plan that we would room together. Ever since then, our focus had
shifted away from trying to get laid in high school, to dreaming about
how we'd get laid at college.

"I've been thinking." Scott said, putting down the crust of his
sandwich. "We've been so confident that we are miraculously going to be
having sex with women once we set foot on campus."

"Because we will." I scoffed.

"Maybe." He said. "But, we've all but given up hope of losing our
virginity in high school. Don't you think we should at least try to do
that before we graduate? If college really is going to be a wonderland
of sexual activity, it would be good to go in at least knowing what
we're doing. Don't you think?"

I had to admit, he had a point. I knew very well from my own handful of
near-encounters with women over the past four years how quickly the
panic of inexperience sets in and ruins everything. I still cringed at
night when trying to fall asleep and the memory of running away from
Becky like a little bitch flashed across my mind.

"You're not wrong." I agreed. "But there's only a couple weeks left of
school. How the hell are we going to accomplish in two weeks what we
haven't been able to do in four years?"