City
Boy
By Robert M.
Grossman
His cousin Jake was two months younger
but always seemed ahead of him. Even though Philip was from the big city, he
learned from Jake’s small town ways. Jake was the first to teach him how to
shift gears in the family Oldsmobile. He showed him how to cast a line in the
stream in back of his house. He taught him how to play pool at the hall near their
grandpa’s fur store. He was the first to get him laid.
Philip was from Chicago and Jake from
Philip was 16 at the time he
convinced Jake to take him to the local brothel, which turned out to be not all
that far from their grandparents’ house. It had apparently been there for
years, quietly accepted by the community. Philip was home for the summer from his
first year away at prep school where there were no girls on campus and no brothels
in town. He was ready.
As soon as he arrived at his grandparents’,
he ditched his sister and brother and raced over to his uncle’s house to tell
Jake what he had in mind. Jake said he would take care of it that night. After
a big family dinner, the two of them casually departed, telling everyone they
were going to a party over by the lake.
When they arrived at the brothel, the
madam, who was clearly in charge, greeted Jake with a knowing smile. Philip
couldn’t take his eyes off the girls who were lounging on soft-cushioned
couches in their bathing suits and bathrobes. The lamps were dimly lit but
bright enough to make out their inviting features.
Jake asked if Joanne was available.
“For you, Jake,
sure. She’s got a break now. Joanne, come on over.”
“She’s not for me tonight. I brought
my cousin Phil for her. He’s from Chi town.”
Philip felt like shrinking into the
corner. The thought of squeezing him into a tight schedule with someone that
Jake had been with time and again made him want to retreat to his grandma’s
house. But as Joanne approached in her deep red bathing suit, he could see that
she was only a few years older and actually quite pretty. He immediately
focused on her breasts which were partially hidden but uncovered enough to keep
his eyes bulging towards them.
She smiled at him after nodding at
Jake, took him by the hand and led him up the stairs of the quaint, old house.
The hallway on the second floor was decorated with wallpaper that looked the
same as at his grandma’s, and the bedroom was as warm and cozy as the one he
slept in there. As soon as he gave her the three dollars, she squirmed out of
her bathing suit, which she let drop to the floor, and helped him off with his
clothes.
“Jake told me this is your first time.
Just do what I say.”
Philip was so consumed by the sight of
her breasts that he paid little attention to anything else. She gave him a
condom and then led him to the bed, placing him on top of her. He immediately
propped his chin in the palm of his hands so he could continue to stare at her
breasts as they bobbled right in front of his eyes. In the meantime, she guided
him into her and directed him to start moving up and down. As he began, he had
the immediate feeling that he had inserted a plunging rod into a car engine
whose oil was in serious need of a
change. It was obviously not what he
expected - whatever that was - and he couldn’t wait ’til it was over. He
continued to suffer his sandpaper journey until she tapped him on the shoulder
and told him he was through. He quickly but carefully removed himself.
She got up and went straight to the
bathroom, closing the door behind her. Philip glowered at the ceiling. “Is this
it?” he pleaded almost out loud. He quickly began to focus on how to elicit
some benefit from this ghastly initiation. He saw her bathing suit lying on the
floor where she had squirmed out of it. If she couldn’t find it when she came
out, he could at least watch her breasts bobble about as she went from place to
place looking for it.
He reached down and grabbed it. There
was a closet facing him, so he opened the door and pitched it as far back as it
would go. He then gently closed the door, quickly dressed himself and quietly
sat down on the bed.
Joanne came out of the bathroom and
stared at the floor where the bathing suit had been. Philip, for his part,
stared at her wondrously voluptuous breasts.
“Where’s my bathing suit?”
“I haven’t seen it. Did you put it in
a drawer?”
She walked over to the dresser and opened each
drawer. His eyes stayed riveted.
“You know I didn’t put it there.
Where is it?”
“I really don’t know,” he lied.
“Get up,” she ordered him.
He got off the bed. She loosened the
covers and ran her hands down both sides of the mattress all the way to the
bottom corners. Then she looked under the bed. He continued to gaze with
delight.
“It’s not here.”
She next went to the door to the
room, opened it and eyed the hallway, probably thinking he had thrown it out
there. Finally, it occurred to her that the closet would be a good place to
look. Philip watched while she got down on her knees and worked her luscious
rear end as far into the closet as it would go, realizing that this would be his
last chance to observe any part of the forbidden fruit. And, indeed, it was,
since she soon found where he had thrown it. She placed it over the front of
her body as though he had somehow accidentally caught her naked, pointed to the
door and told him to get out and never come back.
Over the years Philip visited the family
in
Philip continued to live in the big
city, but had lasting memories of all Jake taught him. There are those who try
to bring the nostalgia of small town