Every Young Man's Dream (5 page)

Adriana saw the look on his face and smiled.
“You like the glasses, huh?”

Troy nodded vigorously.

“
Yeah, most guys do. That
whole slutty librarian thing.”

“
Exactly,” Troy
said.

She walked back towards him and sat down in
the lounge chair down by his feet. Adriana crossed her legs,
forcing her skirt to ride up her leg, drawing his attention. He
could almost see up her skirt. Almost, but not quite.

A few seconds later Troy realized that
Adriana was watching him watch her. He lifted his head slightly,
pausing just for a moment at her glorious tits—which were hanging
out of her dress even more because of the position she was in—and
settled in on her face. Once their eyes were once again locked, she
resumed talking.

“
As I was saying earlier,”
she continued, “Based on yesterday, we know some of your general
strengths and weaknesses. First of all, you have a very nice cock.
Big but not too huge, plus it gets real hard, which is always a
bonus. Second, you know how to use it. You’re not a pro by any
means but you’re not an amateur either. Third, you can go multiple
times in one day, which is always nice. And even nicer still is the
fact that you don’t need a whole lot of time in between sessions
before you’re ready to go. Also, you seem to actually be a pretty
nice guy, which is great, and even though you’re a little shy,
you’re not scared. All in all a pretty damn good place to start. As
for areas that need general improvement: Stamina, for one.
Confidence for another. And I’m sure we’ll have to make you more
adventurous in bed. But those will come in time. What I need to
find out today is some more specific things.”

“
Like what?”

“
Well, for example, how
well do you eat pussy?”

“
Are you asking
me?”

Adriana nodded.

Troy shrugged. “I don’t really know. I’ve
done it a couple of times, and the feedback I got was pretty good,
but I doubt if the girls I was doing it too really knew the
difference between good and bad head. I think they were just
excited to have someone that was willing to do that to them.”

“
Was it your idea or
theirs?”

“
It was mine with one, the
other was theirs.”

“
Did you like
it?”

Troy’s face went red.

“
Don’t be embarrassed,”
Adriana said. “Just answer it truthfully.”

“
Actually I kind of did,”
Troy said. “It wasn’t my absolute favorite thing to do, but it was
pretty fun.”

“
Trust me, that’s a good
thing,” Adriana said. “There is a serious dearth of men who eat
good pussy, and even fewer that actually enjoy it. But as long as
you enjoy it, I can teach you how to do it properly.”

For some reason this made Troy blush even
more.

“
Moving on,” Adriana said.
“Answer quickly, without thinking too much. And don’t worry about
what this means, I’m just trying to get an idea of what you have
and haven’t done. So I know where we stand.”

“
Okay.”

“
Good, then let’s get
started. Ready?”

“
Yes.”

“
Have you ever licked
someone’s asshole.”

Troy shook his head, his embarrassment
deepening. But Adriana didn’t seem to notice. And if she did notice
she didn’t dwell on it. She simply made a mark on the paper
attached to the clipboard and moved on.

“
Ever had your asshole
licked?” she asked, her eyes looking up from the clipboard for a
moment to read his expression.

He shook his head again.

“
Given anal
sex?”

“
No.”

“
Wanted to?”

A pause, then Troy answered, “Yes.”

Adriana wrote something down.

“
Received anal
sex?”

“
No.”

“
Wanted to?”

“
Not
particularly.”

Again she paused, perhaps lending more
credence to his not-so adamant denial than he’d meant to convey.
But he didn’t have time to elaborate. Adriana was asking the
questions more quickly now, rapid-fire style, which lessened Troy’s
sense of embarrassment considerably despite the nature of the
questions but didn’t leave any room for discussion.

“
Have you ever stuck your
finger in someone’s asshole?” she asked.

“
No.”

“
Had someone stick their
finger in your asshole?”

“
No.”

“
Does that make you
uncomfortable to think about a girl playing with your
asshole?”

“
A little bit.”

“
Why? Because it seems gay
to you?”

“
Not really,” he said.
“It’s just something  that doesn’t seem like it would feel
very good.”

“
I see,” Adriana said,
writing this down. Then, looking up at him, she asked: “What if you
were assured that it did. Would you be open to trying it
then?”

He shrugged. “Sure. I guess.”

Adriana made another note on her
clipboard. 

“
Double-teamed a
girl.”

“
No.”

“
Been with two or more
girls at the same time.”

“
No.”

“
Have you ever peed on a
girl?”

“
No.”

“
Wanted to?”

Troy laughed softly and shook his head.
“No.” He noticed Adriana was no longer even looking at her
clipboard. Her eyes were locked onto his face.

“
Ever had your balls
sucked on?”

“
Yes.”

“
Did you enjoy
it?”

“
Yes. Very
much.”

“
What about
deepthroated?”

“
No.”

“
Wanted to?”

“
Yes.”

“
Have you ever tied a girl
up?”

“
No.”

“
Wanted to?”

“
Yes.”

“
Been tied up?”

“
No.”

“
Wanted to?”

A minor hesitation, then, “Yes.”

“
Interesting,” Adriana
said. “Just a few more and we’ll be done. For now, at
least.”

Troy nodded in understanding.

“
Before yesterday, how
many girls had you fucked?”

“
Seven.”

“
How many did you cum
inside?”

“
Five.”

“
On their stomach or
tits?”

“
Three.”

“
On their
face?”

“
None.”

“
Did you want
to?”

“
Yes.”

“
What about in their
mouth?”

“
None.”

“
Did you want
to?”

“
Yes.”

“
Did you titty-fuck any of
them?”

“
No.”

“
Did you want
to?”

“
A couple them,
yes.”

“
Did any of them ever sit
on your face?”

“
No.”

“
Did you want any of them
to?”

“
It never crossed my
mind.”

“
Is that something you’d
object to?”

Troy paused as he thought about it for a
moment. “No.”

“
Did you ever get rough
with any of them?”

“
No.”

“
Did you want
to?”

“
Yes. With a couple of
them.”

“
How many?”

“
Two. No, make that
three.”

“
Did any of them ever get
rough with you?”

“
No. But one liked to take
charge.”

“
Did you like
that?”

“
Yes. Sometimes, at
least.”

“
Have you ever fucked a
stranger?”

“
No.”

“
Have you ever wanted
to?”

“
Yes.”

“
Well, that’s about it,”
Adriana said, setting the clipboard and pen on her lap. “One last
question and then we’re done.”

“
Okay.”

“
Was this awkward for
you?”

“
A little at first. But by
the end, no.”

“
That’s good to hear,”
Adriana said. She set the clipboard on the stand next to her chair
and started to take off the glasses.

“
Do you mind keeping those
on?” Troy asked.

“
You like them that much,
huh?”

He nodded.

“
Do you want me to suck
your cock with them on?”

He nodded more vigorously.

Adriana laughed. “Okay, but first you have
to do something for me.”

“
Anything.”

“
You said you’ve eaten
pussy a couple times before, right?”

“
Yeah.”

“
And that you thought you
were pretty good at it.”

“
That’s what I was
told.”

“
But more importantly, you
enjoyed it, right?”

“
That’s right.”

“
Then come on over here
and show me what you’ve got,” Adriana said, pulling the bottom half
of her dress up over her waist and spreading her legs. She wasn’t
wearing any panties. Her pussy was smooth, recently shaved. And
glistening. Apparently the questions had excited her as much as
they had excited Troy.

He practically leapt off the couch and was
on his knees in front of Adriana within seconds. He looked up at
her expectantly, awaiting instructions.

“
This is all you,” Adriana
said. “I’m not going to give you any direction. I want to see what
kind of skills you have.”

Troy nodded, then took a deep breath,
grabbed ahold of her thighs, spread them slightly and pressed his
face between her legs. He went to work on her shaved, incredibly
smooth pussy, starting off slowly, licking the outside of her pussy
lips, tasting her tangy sweetness on the tip of his tongue.

He glanced up to see how she was reacting
and saw her looking down at him, watching him carefully, a little
smile perched on her lips. She definitely looked happy but not
ecstatic, so he figured he needed to turn things up a notch bit.
Returning his attention back to her pussy, he changed his
approach.

Troy stuck his tongue out and ran it up her
pussy, starting at the bottom of her snatch and slowly moving it up
to the top, lapping at it like a kitten drinking milk. Adriana
started to moan softly so he increased his speed, licking more
quickly now, his rigid tongue slipping deeper and deeper into her
silky smooth insides with every pass.

He ventured another glance up and saw that
Adriana’s eyes were closed and her head turned slightly towards the
ceiling. The look on her face plus the increased sounds of pleasure
coming from her mouth excited Troy. He could feel his cock pressing
painfully against his pants. He was enjoying this more than he’d
ever thought possible.

Adriana’s juices were gushing, drenching
Troy’s face, inciting him further. Feeling adventurous, Troy
grabbed Adriana’s legs, pushed them back further, giving him better
access to her pussy. Then he took a deep breath and buried his head
in between Adriana’s legs, smashing his face up against her flesh,
forcing his tongue deeper inside her dripping wet pussy.

Adriana let out an excited little yelp,
followed by a deep, pleasurable groan. Troy shook his head back and
forth quickly, further covering his face in her juices. He backed
off for just a second to catch his breath.

He looked up at Adriana and saw that she had
pulled her dress down, exposing her glorious tits, and was groping
them with both her hands. Happy and proud and excited all at the
same time, he dove back between her legs once again.

“
Holy fuck,” Adriana
moaned as Troy went back to work on her pussy, digging his tongue
in as deep as he could get it. “Right there, Troy. Right fucking
there.”

Adriana grabbed the back of Troy’s head with
both hands and pulled him further up inside her, holding his face
up against her flesh, her pussy opening up even more, allowing him
deeper access to her insides.

Troy breathed Adriana in, her wet, musky,
tangy sweetness his only nourishment while she moved her body
against his face, sliding her pussy up and down on his rigid
tongue, riding his face, her legs quivering as she approached
orgasm.

And then she was there, her body tensing up
for a moment before relaxing, an intense moan coming from her mouth
as her pussy juices flowed out of her, soaking Troy even
further.

Adriana released his head, allowing him to
breathe properly. He did so in gasping breaths, a big smile on his
face while he looked up at Adriana, her nipples hard and her tits
glistening with sweat as her chest heaved. Her hair was messed up
and it hung down over her face, covering half of it. Her eyes were
locked on his and her mouth was turned up in a satisfied smile.

“
Well, what did you
think?” Troy asked, his own grin threatening to split his face in
two.

“
I have to admit, I’m
pleasantly surprised,” Adriana said. “You were pretty damn good
down there. A hell of a lot better than most men. And even some
women.”