Chase of a Lifetime (2 page)

He pulled a small container of Vaseline out
of the bag and spread it all over the dildo. He rubbed the lube left on his
fingers around the lips of his anus and inserted his fingers a few times to
open himself up. When he knew everything was well-lubed, he rested flat on his
back and spread his legs. He reached down between his legs and pressed the head
of the fake penis to his opening. He worked the big head inside with gentle
turns and thrusts so it wouldn’t hurt too much at first. The deeper he inserted
it the higher his legs went up. His feet arched and his toes curled. The pain
in his stomach subsided and a feeling of absolute bliss passed through his
body. By the time the fake cock was inside his body as far as he could push it,
his dick grew fully erect and rested on his flat abdomen, with the head covering
his naval.

He grabbed the base of his shaft with his
right hand and squeezed it hard. He glanced down between his legs and bit his
bottom lip. Though the dildo had only been inside him for a few minutes, he had
pre-come at the tip of his penis. He squeezed his shaft and milked it a few
times. Then he released it, ran his index finger across the tip of his dick,
and swiped a drop of pre-come. He licked the pre-come off his finger and
swallowed. He repeated this a few times until his dick grew so hard the head
looked as if it were ready to explode.

When he started jacking with his right hand,
he slid the dildo in and out with his left. The faster he jacked the harder he
fucked with the dildo. He closed his eyes and imagined the handsome traveling
salesman he’d met on the plane that morning. He fantasized about being locked
in the airplane bathroom and going down on his knees. He pulled the salesman’s
zipper down and yanked out a huge exaggerated fantasy erection. It would have
made cartoon satires about porn look tame. In the fantasy, Jim knew there
wasn’t much time because the plane would land soon, so he sucked fast and kept
an even tempo. He jacked his own dick while he sucked the salesman off. When
the pilot told the passengers to return to their seats and put on their
seatbelts, the salesman climaxed and blasted his load down Jim’s throat. Jim
imagined swallowing the salesman without missing a drop. While he did this, he
imagined himself coming on the bathroom floor between the salesman’s expensive
black shoes.

Jim usually fantasized about something while
he jacked off. The more he thought about the salesman’s exaggerated dick the
closer he came to his own climax that afternoon in his childhood bedroom. At
one point, when he knew he was near the edge, he stopped jacking his dick and
grabbed the dildo with his other hand. He’d managed to nail this down to a
perfect science by then. He would keep his legs open; he would push and pull
the dildo with both hands and climax without ever touching his penis. It took a
while for him to reach this point, but never regretted the effort in the end.
Whenever he climaxed this way, without touching himself, the orgasm he
experienced came from deep down inside his body in a place hard to describe. It
wasn’t exactly his prostate, even though most people would have argued with
him. This place held his secret pleasure and only he knew how to reach it. These
climaxes were often so intense he experienced small multiple orgasms after the
first one and wound up shooting several smaller loads.

There was one problem. If he had continued
fantasizing about the salesman on the plane it wouldn’t have worked. The
salesman brought him close to the edge. But Jim always thought about one person
right before he came:
 
a guy he’d grown
up with named Cain Mayfield. They’d gone to kindergarten together and had
remained best friends all the way through high school. Cain Mayfield, an only
child like Jim, grew up on a similar ranch about five miles down the road from
Jim’s.
 
Except for casual meetings by
accident during holidays and spring breaks, they’d grown apart after
graduation. Cain had gone to Stanford and Jim to Princeton. Cain had always
been more aggressive and outgoing. He’d dated girls in high school and he’d
been involved in every social event, while Jim had remained at home watching TV
or reading books most of the time.

Jim thought about Cain Mayfield that
afternoon in his bedroom. When he knew he was close, he started to remember all
the times he’d taken gym class with Cain in high school. He imagined Cain
standing next to him in the locker room in nothing but a sweaty jock strap and
white sweat socks. Though there were other young men in the locker room, he
only saw Cain’s handsome face and sweaty hot body. Cain had been his hero. He’d
been the star quarterback; he’d been the captain of the baseball team: the
school jock. There wasn’t a sport he didn’t excel at from shooting hoops to
running track.

With one hard push, Jim forced the huge
dildo to the bottom of his ass and tossed his head back. He closed his eyes,
imagined his old friend removing the jock strap in the locker room, and said;
“Fuck me, Cain,” over and over. He whispered this until his toes curled all the
way back and he blasted a huge load all over his chest without touching his
dick. For the next minute or two, he remained this way, repeating Cain’s name
in his head. While smaller, less intense orgasms passed through him, he
imagined what it would be like to bury his face between Cain’s legs and just
inhale his scent one time. He’d been pretending all this for so long he slid
through each sensation with a smile. Sometimes he frowned because he knew it
would never happen in real life.

A few minutes later, Jim pulled the dildo
out of his ass, gathered everything from the bed, and went back to the
bathroom. After he cleaned up and put the dildo and Vaseline back into the red
velvet bag, he pulled the drawstring and glanced into the bathroom mirror. He
stared at his image for a moment, wondering if Cain would think he looked like
Adam Levine the rock star with his new haircut and clothes. He also wondered
how he would react when he saw Cain that night at the graduation party his
mother and father were giving him. He suspected Cain would be there, but he
wasn’t certain. Cain’s mother and father were good friends with his mother and
father.

Then Jim shook his head fast, as if trying
to wake up from a bad dream. He leaned forward and said, “This summer you’re
going to give up on this dumb fantasy and find out what it’s like to be with a
real man. You’re not a kid anymore. One way or the other, like it or not, it’s
time to move on and start living as an adult.”

Although Jim had never denied being gay,
he’d never formally come out of the closet either. As he dressed that night for
the graduation party, he cringed at the thought of his mother introducing him
to single young women…and all those comments about him finding the right girl
to marry he’d be forced to suffer through. Even though he never talked about
women, dated women, or expressed interest in women, his parents seemed to think
he was straight. At least they never said anything aloud. He sometimes wondered
if their silence came from wishful thinking or classic denial, because he’d
never given them the slightest inclination one way or the other.

When he buttoned his white dress shirt and
thought about going downstairs and Mrs. Anderson shoving her red-headed
daughter up against him, he closed his eyes and shook his head. When he pulled
up the zipper of his beige flat front chinos and thought about the Rickard girl
who’d also just graduated from college, he almost caught the fly of his
underwear. The Rickard girl was one of those aggressive types who wanted a
husband and wasn’t willing to wait. If she was there, she’d flirt, bat her
eyelashes, and speak in her sweetest, softest Texas accent until he would want
to puke in the swimming pool.

Before he opened his bedroom door to venture
down to the party, he put on his navy blazer and took a deep breath. Then he
exhaled, lifted his head higher, and went down to the first floor where the
guests had already arrived an hour earlier.

When he descended the grand semi-circular
staircase, he clenched his fists and set his jaw. He continued downward at a
slow pace, forcing a smile that felt so fake it hurt his jaw. One woman
shouted, “There he is, the guest of honor.” While everyone else in the hallway
turned to glance up at him, he smiled and continued down the steps. People
patted his back and congratulated him. He thanked them without showing any
emotion one way or the other. One older guy who worked at his father’s law firm
grabbed his arm and said, “I couldn’t miss that peppy little car out there. Hot
damn.”

Jim’s father, Radcliff Darling, stepped up
behind the man and said, “It was a graduation gift.”

Jim refrained from rolling his eyes. Who
used the word “peppy” anymore? He took a quick glance around. At least the
people he’d feared would be there weren’t in sight. There were no younger
people. This looked more like a party for adults…all of his mother and father’s
friends.

The older guy patted Jim’s back and said,
“I’ll bet that car’s going to be a chick magnet. You’ll have the girls chasing
you down the street in that little baby.”

Jim smiled. His mother and father had given
him a brand new silver BMW 650i convertible as a graduation gift. He’d been
wondering how many hot young guys would be chasing him down the street.

Radcliff glanced at Jim and beamed with pride.
His face illuminated and he smiled so wide Jim saw the fillings in his back
teeth. “Jim’s a good kid and he’s worked hard in school. Helen and I wanted to
do something special for him for graduation.”

Someone else patted Jim on the back and
congratulated him. He started to feel light-headed and his heart began to race
for no apparent reason. His first instinct was to get out of there as fast as
he could, so he smiled and said, “I’m going out to check the car to make sure I
closed the windows. I heard it might rain. I’ll be back.”

They were all drinking and laughing so much
they hardly noticed him leave. It was one of those parties where most people
congratulate the guest of honor to be polite and then continue having fun
without really caring one way or the other about the guest of honor. As he
crossed to the front door and opened it, he found another one of his father’s
friends standing in the doorway.

“Well, there you are,” the man said. He wore
a pale blue seersucker suit with a white shirt and pale yellow bowtie. He had
three chins and his stomach rounded as if he’d stuffed his shirt with a throw
pillow.

“Ah well, here I am,” Jim said in a deadpan
voice. The man’s name was Bill Harper and he’d been a friend and client of Jim’s
father for years. He was President of some bank in
Dallas
, but Jim couldn’t recall which one. He
also had a single daughter, Bitsy, who was almost the same age as Jim. This
could be trouble. Jim looked over his shoulder to see if Bitsy was behind him.

Bill Harper put his arm around Jim and
dragged him back into the main hall, before Jim had a chance to resist. “I’m
going to get a drink. You wait right here and we’ll catch up. Wait until I tell
you about what good old Bitsy has been up to since you last saw her. You’ll
love it. She’s a real
go-getter
, that girl of mine.”

As Bill Harper headed to a bar in the living
room, Jim made his way back to the staircase. Bitsy Harper was a rotund young
woman with frizzy hair and small eyes. They’d been in student government in
high school and he’d always thought of her as one of those passive aggressive
types who get what they want in subtle ways. She’d once said, “I’m not sure I’m
going to run for President of student government. I don’t think I have what it
takes. I’m way too shy for that. I’m a simple girl.” She ran; she won; she
ruled the school with an iron fist. Bill had been trying to fix Jim up with her
since they’d been in high school.

Jim figured if he could sneak back up to his
bedroom no one would notice him missing. But someone else grabbed his shoulder
and congratulated him. A man Jim didn’t even know passed by, patted the top of
his head, and messed up his hair. A woman with big red hair grabbed his face
and kissed him on the cheek. “We’re all proud of you. What are you going to do
now?”

Jim shrugged and said, “I was going to check
on something upstairs in my bedroom.” He wondered why she cared.

The woman laughed. “I’m talking about what
you’re going to do with your life.”

He didn’t have a clue about what he was
going to do with his life. He’d graduated with a degree in English. He’d been
thinking about moving to
New York
and getting a job in advertising. A good friend had offered him a job in public
relations in
Los Angeles
.
But Jim knew his father wanted him to go to law school and he’d been keeping
his plans quiet until he actually decided that’s what he wanted to do. “I’m
still discussing it.” He almost choked on his own words; his heart started
beating fast again and he wasn’t sure why.

A tall man with gray hair in a dark suit came
up from behind and put his arm around him. He looked down, into Jim’s eyes, and
gazed at him with the kind of adoration that most straight men did with women.
“Jim,” he said. His tone remained soft.

“Mr. Kroll,” said Jim. He had a feeling he
was being undressed by Mr. Kroll’s eyes.

“I want to talk to you for a minute,” Mr.
Kroll said. “Come outside with me where it’s more private.” He kept his arm
around Jim’s shoulders and guided him out back near the swimming pool. He
smelled of cheap drugstore aftershave and red wine.

When they were outside, beside a thick group
of shrubs not far from the pool, Kroll removed his arm from Jim’s shoulders and
took a step back. He gazed at him once again, looked him up and down from
crotch to lips, and said, “I want you to consider one thing.”