Seducing the Shy Guy: Part 1
SEDUCING THE SHY GUY: PART 1.
HIS SISTER'S FRIEND OLIVIA; TRIES TO TEACH THE
ROPES TO SHY COREY.
BASED ON A POST BY LEADER12 [https://www.literotica.com/authors/Leader12/works/stories],
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► PODCAST [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy1.mp3] AT STEAMY
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Corey was happy the semester
was finally over. His first term at college was fun, but it was
challenging. He found high school to be pretty easy, even though he
took honors classes; and then AP classes; in math and science. But
when he got to college; where lots of people were as smart as he was;
he had to work a lot harder to keep up with the pace. He was also
taking advanced classes as a freshman because he had received some
college credit from his AP classes.
The funny thing about it was
that he Liked the challenge. He especially liked the advanced Physics
class he was taking, since it gave a scientific explanation of things
everyone experiences in the world every day. And he liked the
challenge of proving he could do the work. He always loved JF Kays
speech about going to the moon, when he said, "we choose to go
to the moon not because it is easy but because it is hard."
Whenever Corey repeated the line, he always dropped the 'R' on the
last word and did a terrible job of trying to replicate JF Kays
Boston accent, pronouncing the last word "h a h d".
But now he could relax for a
few weeks during Christmas break. He lived less than two hours away,
and his parents texted to say they'd be at the dorm in fifteen
minutes.
When their car pulled up,
Corey walked outside, rolling one suitcase with some clothes. He was
surprised when the back door opened, and his sister, Melissa, stepped
out. Suddenly he had a huge smile on his face.
"Melissa!" he
yelled. "I didn't think you were back yet."
Melissa was two years older
than Corey and went to a different college. She had told him she'd be
home the day after him.
"I wanted to surprise
you," she said, just before the two embraced. "Good to see
you, Corey!"
The two siblings were always
very close even though they were, in some respects, very different.
Corey was generally quiet, shy, and uncomfortable in groups of people
who weren't his friends. Melissa, on the other hand, could show up on
another planet at a party with aliens, and within ten minutes, she'd
know all the aliens' names, and they'd all love her. She was very
popular in high school; he was not. She dated a lot in high school;
he did not.
Corey looked up to his sister
in many ways. Even though she was beautiful and very popular, she was
very down-to-earth. Some of the other pretty, popular girls in high
school were real snobs. They wouldn't even consider talking to a nerd
like Corey. But Melissa was friends with everyone. She had some
friends from the Pom Squad, some friends from her honor classes (some
of whom were a little nerdy, like Corey), and random friends she had
just made over the years. When some of her "popular"
friends made bitchy comments about someone; especially about "nerdy
guys"; Melissa would call them out. Corey wasn't sure if she was
explicitly trying to defend him or just not tolerating someone being
a jerk. But it always made him respect her even more when she'd go
against the crowd and defend people.
As they drove home, everyone
asked Corey about finals. Corey caught up with Melissa, since they
didn't talk a lot the prior week when they were both studying for
finals. On the way home, they stopped for lunch. Corey smiled when
they were all piled into a booth, with Melissa next to him and his
parents on the other side. It reminded him of his childhood, when
they'd go out as a family and laugh and make fun of each other. He
had friends who had older sisters, but none of them got along like he
and Melissa did. He always appreciated Melissa; probably more than
she realized.
That night, after everyone
got ready for bed, Corey was sitting up in his bed surfing the web on
his phone when he heard a knock on his door.
"Come in," he
yelled.
Melissa walked in wearing a
t-shirt and shorts, her standard sleeping outfit. She sat on Corey's
bed and started asking more questions about his first semester. Once
again, Corey smiled to himself as this was another event that
reminded him of his childhood. Melissa would often plop on his bed to
talk to him about everything and anything. When he started middle
school, and then high school, she also tried to give him pep talks
about girls. He was obviously very shy and didn't date in high
school, and Melissa always tried to convince him that girls would
like him if he just tried.
So, he wasn't surprised when
Melissa finally got around to asking if he had gone out with any
girls. When he said he hadn't, Melissa again turned into his personal
life coach and biggest cheer leader, telling him he didn't realize
that he's a good-looking guy and that any girl would like him if he
just talked to them. While he appreciated Melissa's concern and
confidence in him, this was not one of the conversations he enjoyed.
Like when he was in high school, Melissa left a little frustrated and
definitely feeling sad for her brother.
ON the following Monday,
Melissa had a few of her high school friends over. They were sitting
outside, just catching up on everyone's last semester. One of the
girls asked about Corey and how he liked college. Melissa let them
know he was doing well, but she briefly mentioned that he's still as
shy as he ever was. She told them she felt bad he didn't have the
confidence to talk to girls.
As soon as she heard that,
Olivia smiled to herself. Back in high school, she was Exactly like
Corey. She was shy around boys and didn't think they were interested
in her. It didn't help that some of her friends; including Melissa;
were absolutely beautiful. Some of the cheerleaders had big, curly
blond hair, big boobs, and big personalities. They knew how to do
their hair and apply makeup; a little too much, in Olivia's opinion;
to look like movie stars. Olivia had a thinner body, full B-cup
breasts, and stick-straight, pitch-black hair that went halfway down
her back. She had big, brown eyes which many would find to be
alluring. But she just didn't understand how attractive she was.
She was still uncomfortable
around boys when she left for college, but her freshman year roommate
fixed that. She was a year older, and she told Olivia she was making
it "her personal project" to help Olivia come out of her
shell. She was fine around girls; she only got nervous around guys.
So, her roommate dragged her to every party she went to and forced
her into situations where she had to talk to guys. It was a very
painful couple of months before she finally found a guy whom she
found easy to talk to. She also thought he was hot, and he ended up
being the one to take her virginity. Once she got "over the
hump", the damn broke. She suddenly realized she Could talk to
guys, that some guys thought she was hot, and sex was fun!
She felt bad for Corey; she
remembered how miserable she was before her "awakening".
She was jolted out of her
thoughts when she heard, "Hello! Earth to Olivia. Are you
there?"
"Huh?" she asked,
realizing the other girls were looking at her.
"I said we were going to
go out for lunch and then go to the mall," Melissa said. "Are
you good with that?"
"Actually, I'm not
feeling great. I think I'm going to head home. I'll catch up with you
guys later."
"You sure?" Melissa
asked. "Are you okay?"
"Yeah, I just didn't
sleep well last night, and I'm kinda' tired," Olivia responded.
"Okay," Melissa
said, we're going to head out.
"Okay. I'm gonna go say
hi to Corey and then leave," Olivia said.
As the other girls headed
out, Olivia went inside and up the stairs. She had been in Melissa's
house a million times, so she felt quite comfortable being there
without her. When she got to Corey's room, she knocked.
"Come in," she
heard.
She opened the door, and
Corey was sitting at his desk where he had been looking through
email. He turned when the door opened, and he smiled. He always liked
Olivia.
"Hi, Corey," she
said with a smile.
"Hey, Olivia. How ya'
doing?"
"I'm good," she
said. "How about you?"
"No complaints,"
Corey said.
They chatted for a little
while before Olivia said, "Melissa said you haven't done much
dating at school."
Corey looked embarrassed and
was a little pissed at his sister.
"Why would she tell you
that?" he asked.
"It just came out when
someone asked how you were doing. Nothing to be upset about,"
she said.
"It's just not easy;"
he said, with his voice trailing off.
"You know," Olivia
said, "I used to be the same way. You know how shy I was."
"Yeah, I suppose."
"But my roommate really
forced me into situations where I'd Have to talk to guys, and
eventually it wasn't so hard. Hey, I've got an idea. Come here."
"What?" he asked,
given they were already in the same room.
"I said stand up. Now!"
she said with a laugh.
Corey got up and walked
toward her. She walked into the hallway, outside his room, and then
stopped. He followed her.
"Okay, let's pretend
we're at a party and there's some music playing."
Corey laughed.
"Seriously? Pretend
we're at a party?"
"Shut up and listen to
me. Yes, pretend we're at a party."
"Oh, okay," Corey
said in the most sarcastic voice possible. "I'm at a party."
"Okay," Olivia
continued, "now pretend you see me, and you think I'm hot."
"Well, that doesn't take
any pretending," he said.
Olivia pulled her head back
with a shocked look.
"You think I'm hot?"
Now Corey was embarrassed and
looked down.
"Well, of course I think
you're hot. Who wouldn't?"
Olivia was still surprised,
but she ignored the comment for now.
"Okay, so;" Then
she moved a few feet down the hallway. "So, you decide to come
talk to me."
Corey looked at her.
"Let's go Corey.
Remember? You think I'm hot, so you come over to talk to me. Come
here."
Corey walked the few feet to
where Olivia was leaning against the wall.
"Hi, I'm Olivia,"
she says.
Corey looks at her as if
she's crazy, but when Olivia raises her eyebrows and holds her arms
up with her palms up in a "your turn" gesture, Corey
finally goes, "Oh, hi. I'm Corey."
"Hey, look at that,"
Olivia says, "you're talking to a girl."
"So, do you like this
music?" Olivia asks.
Corey finally decides to play
the game.
"Yeah, they're not too
bad."
"Have you seen many
bands on campus," she asks.
Without thinking too much,
Corey replies, talking about some bands he's seen.
"See," Olivia said.
"Once you get going, it's not so bad. Now, if the girl is
smiling at you a lot or maybe putting her hand on your arms when
she's talking, like this;" and she places her hands on Corey's
upper arm, "then it means she's into you and wants to keep
talking. But after a while, maybe she says, 'It's kind of loud here.
You wanna go talk in my room?' That's a good sign."
Olivia puts her hand on
Corey's arm and leans into him as she says, "It's kind of loud
here. You wanna go talk in my room?"
Corey chuckles and says,
"Yeah, sure."
Olivia grabs his hand in hers
and walks the three feet to Corey's room and pulls him inside. She
closes the door and locks it.
"So, if she invites you
to her room, it probably means she likes you and wants to get to know
you better. Maybe she wants to make out. If she doesn't immediately
go and sit down but is standing, walk up to her and put your hands on
her waist, like this."
Olivia put her hands on his
waist, but Corey left his hanging down.
"Hey," she said,
"are you listening?" she said with a little chuckle. "We
just came to my room, and I didn't sit down. Put your hands on my
waist like this."
Corey smiled. He didn't know
why Olivia wanted to play this game, but he didn't want her to get
mad at him. So, he put his hands on her waist.
"So, if you get this
far, she definitely wants to at least kiss you," Olivia said.
"You should lean in and give her your best kiss."
Corey nodded, as if he
understood.
After a couple of seconds,
Olivia said, "I'm waiting."
"Huh?"
"I said, you should lean
in and give this hot girl a kiss."
Suddenly Corey realized
Olivia really expected him to do this. Now. Here. With her. He wasn't
sure why, but he thought he'd better do something. He leaned his head
forward about an inch. Olivia smiled to herself but was happy he
moved at all. She figured she'd better show him. She leaned forward,
closed her eyes, and placed her lips on his. Corey didn't move at
first, but, finally, he realized she was serious. So, he started
kissing her.
He couldn't believe this was
happening. He had kissed a few girls, but nobody as hot as Olivia.
His sister's friend. When Olivia opened her mouth, Corey did the
same. When he felt her tongue enter his mouth, he moved his hands
behind Olivia's waist and pulled her against him just a bit as they
enjoyed a passionate kiss.
Olivia was surprised he
pulled her against him, and she could tell he was getting hard. She
liked the feeling. A lot. And she started getting excited, herself.
After five minutes of
wonderful kissing, Olivia pulled her head back and smiled.
"That was nice, Corey.
Real nice."
Corey just looked at her
quietly with a smile on his face.
"So obviously she likes
making out, but now you have to figure out if she's interested in
something more. You're in her room; by the way," she said,
looking around as if to take in the whole room, "do you like the
way I decorated my room?"
Corey looked around and
smiled.
"Yes, I do. It's very
nice. We seem to have similar tastes."
"So, now it gets even
more fun. If you're in her room and she's been kissing you, she might
want more. But you've got to go slowly, because you can't assume
anything. If you do something and she stops you or says no, that's
okay. That just means she's not ready for it yet. So go back to
kissing her. From my long-term experience kissing you, she'll like
more of that."
They both smiled.
"So, something you can
do that lets her know you're interested in a little more without
freaking her out is when you're kissing her, move one of your hands
onto her ass and give it some gentle squeezes. If she doesn't object,
keep your hand there and pull her against you. If she says 'uh-uh' or
moves your hand off her butt, that's fine. Just move your hand back
to her waist and keep kissing. Let's try that."
Corey tried to process what
he heard. Did she really say, "let's try that"?
When Olivia started moving
her head forward, Corey leaned forward, and they started kissing
again. Not believing he was really doing this, he slid one hand down
onto Olivia's ass and gave it a little squeeze. It felt incredible.
Olivia softly moaned and Corey pulled her against him. She started
rubbing her pelvis a little bit against Corey's hard dick, and he let
out his own groan. They continued kissing and Corey continued
squeezing Olivia's ass, and they were both very excited.
After another ten minutes,
Olivia again pulled her head away from him, but he left his hand on
her ass.
"Hmm," she said,
"you're very good at this. You must be very experienced."
This made Corey laugh. "You should be feeling pretty good about
how it's going with your hot friend by now," she said, smiling
at calling herself a 'hot friend'. "So now you need to take the
next step, again being subtle to let her bow out gracefully if she
wants to. So, keeping the one hand on her butt, slide your other hand
up her side."
Corey did as instructed. His
hand was getting dangerously close to Olivia's breast.