Wednesday, 1 July 2009
12:21:58 PM (GMT)
'What the hell am I going to do now?' Chris thought. High school had ended as
abruptly as it does for many young people, and now he was faced with all the
possibilities of his life stretching away before him.
He looked at himself in the mirror. He was tall at 6'3", but not a giant like the
guys on the basketball team. He had a lean muscled frame from many trips to the gym.
Dark brown hair and deep-set brown eyes with heavy eyebrows gave him an intense look,
and he thought he was not altogether bad looking.
A frown wrinkled his face then as he thought to himself, 'Then why the hell am I
still a virgin?' He shook his head as he turned from the bathroom mirror to get
dressed in the warm sunlight of his room. The dust motes swirled around him as he
pulled on his clothes.
The first day of life after graduation, and he had no idea what he was going to do
with himself. Dressing quickly he skipped down the stairs to the big empty kitchen
and the smell of coffee in the morning air. His mother had left for work hours ago.
As a partner in a big real estate firm she was always home late and gone early. The
huge kitchen was filled with every cooking gadget and device known to man, which he
found amusing considering his mother never cooked.
He made himself some toast and coffee with sugar before heading into the living room,
and then out onto the back patio next to the pool. The sun was warm and relaxing as
he flopped down in a chair, and looked out at the sculpted garden. He lived in a posh
neighborhood due to his mother's vanity. A pair of retired doctors, who attended all
of his mother's dinner parties, owned the house to the left. He could not think of
two more boring people. The Nelsons owned the house to the right.
He used to spend hours staring out of the upstairs window at the Nelsons' pool and
their daughter when he was a sophomore in high school. Her name was Sabrina, and she
was a few years older than he. She had been away at college for a few years now.
Still her shapely body and the tiny bikinis she wore had provided a great deal of
fantasy for him to masturbate to. He had noticed recently that she must have gotten
her good looks from her mother when Ms. Nelson came to his mother's last party. She
was like her daughter: short and slim with a large chest, full hips, brown hair, and
striking blue eyes.
He finished his breakfast and rose to leave as the sound of someone diving into the
pool next door drifted to his ears. Maybe Sabrina was home from college for the
summer. He raced up the stairs two at a time and to his old familiar perch looking
out the window in his mom's bedroom down onto the pool next door. It wasn't Sabrina,
but her mom swimming laps. She was wearing a one-piece bathing suit and her full
round butt stirred his penis in his pants as he watched her swim. She was shorter
than her daughter and had a fuller figure which he liked, and her dark brown hair and
graceful movements made her very attractive.
He reached down and began to rub his crotch as he watched her, finally dropping his
shorts and taking his hardening cock in his hand. She made slow deliberate laps doing
the breaststroke, and he watched her ass as she swam each length. His cock was rock
hard now and he was stroking it firmly as he watched her. She reached the end of a
lap and turned on her back cutting through the water in a backstroke. The sight of
her large breasts made him stroke faster and he could feel his orgasm building inside
him as his balls tightened against his body. He closed his eyes and leaned against
the window as he felt the cum shoot from his cock, stroking it slowly now as each
spurt of cum shot from him. He opened his eyes and could see her standing in the
shallow end of the pool. He ducked back out of the cum-streaked window. His heart was
hammering in his chest as he leaned out to see if she had been looking at him but she
was already disappearing into the large house. He breathed a sigh of relief before
grabbing the tissue off his mother's night stand and the Windex from her bathroom to
clean the long white streaks of his cum off the glass.
He spent the rest of his day playing video games on the computer in the office and
surfing the net. He went to all his usual porn sites and masturbated twice more
during the day, the normal routine for his 18-year-old hormones. Around five the
"Hey Chris, it's mom. How was the first day as a graduate!?" Her voice was its usual
perky, full of energy voice. He didn't know how someone who worked 12 hour days could
always have more energy than him.
"Good mom, just hung out at the house. Might try to do something with Tony tonight."
"That sounds like fun honey!" God he hadn't even told her what he was going to do.
"I'm going to be a bit late, but Barbra is supposed to meet me at the house at six so
we can go to the gym. Can you stick around to let her in, and keep her company till I
get there about 6:30?"
"Sure mom, no problem. I wasn't planning on going out till around nine anyway." Great
he thought, now I have to baby sit mom's friends.
"Thanks honey, you're a dear. Order some pizza for dinner on the credit card in the
desk drawer, and I'll see you soon."
"Okay mom, later."
He hung up the phone and walked back upstairs into the den. An AVI file of a woman
slowly riding a huge cock had finished downloading and was slowly playing on the
screen. You could see the hard cock pulse as the man shot his cum up into the pink
pussy. The pulse of each wad of cum seen clearly in the flex and jump of his cock
with just the head buried inside her. When the woman slid off of him his own cum ran
back out of her all over his still dribbling cock.
Chris felt his cock twitch and begin to harden again. He walked toward the desk and
glanced out the window as he passed it, and froze in his tracks. The lights were on
in the bedroom next door and he could look right into Ms Nelson's bedroom and
bathroom. What had caught his attention was the naked image of his neighbor as she
stepped into the shower. He had only seen her for a moment but he had caught a
glimpse of her bare breasts and tan body as she stepped into the shower. His cock was
rock hard now, the video on the computer forgotten as he stared into the windows next
The office had grown dark as the sun had set and only the glow of the CRT illuminated
anything as he pulled his cock out and began to stroke himself. He imagined her
floating on her back in the pool this morning, and the thought of really seeing those
big tits had him close to cumming already. He knew she would be getting out of the
shower any minute and he would be able to watch her as she dressed. His cock began to
ache as his fourth orgasm of the day began to build in him. The doorbell rang.
It was like being hit in the head with a hammer as he realized it had to be Barbara,
and a quick glance at the clock confirmed it was just before six. "Damn it!"
He stuffed his sizable erection into his shorts and started down the stairs, pulling
his loose T-shirt over his crotch. He snapped on a few lights as he went down the
stairs and into the foyer to answer the door.
Barbara had been his mom's best friend for as long as he could remember. They had
been roommates together in college, and some of the stories mom had told him about
their time together were quite wild. He often wondered about what they did that she
did not tell him.
He opened the door and Barbara smiled at him as she saw him. She immediately stepped
into the doorway giving e him her usual quick hug. He prayed she couldn't feel his
erection straining his shorts.
"Hi Chris! How's it going for the big graduate?"
She was taller than his mom, about 5'8" and had long blonde hair and green eyes. Her
chest was small, but complimented her small waist well. She was very fit, and loved
to run and cycle in her free time. He always thought she was too skinny. He had
always had a thing for girls with big chests anyway.
"I'm good Barbara, mom is gonna be a bit late, so she told me to have you wait for
"Stuck babysitting me Chris?" she said smiling as she stepped in and he closed the
door. He headed to the kitchen not wanting to stand there where she might see his
"It's no problem. I don't mind. Besides I'm not going out till later."
He turned the corner in the kitchen and grabbed a seat on one of the bar stools
around the center island. Barbara dropped her purple gym bag on the floor before
crossing to the refrigerator to get a bottle of water. Her ass strained her tight
shorts as she bent over in the fridge and he felt his cock retain some of its
stiffness at the site. As she stood and turned he quickly looked away
"Got big plans tonight? Going to take some lucky girl out somewhere?" Barbara's smile
was still on her face as she spoke, and she took a long pull on her water.
"No. Probably just going to hang out at Tony's. I don't have a girlfriend or anything
right now." He didn't mention he had never had a real girlfriend, figuring why
volunteer information that you were a looser.
"No girl!? Well now what is the world coming to?" She paused a moment as she smiled
again. "Look Chris, you don't have to hang out with me, I'll wait for your mom. Go
get ready for your night."
"Cool. Thanks Barbara, I'll be up stairs," he said, suddenly very anxious to return
to the office upstairs.
He took the stairs two at a time, and the video was still repeating on the screen of
the computer as he looked out the window. The bathroom was dark and Ms Nelson was
standing in front of her mirror in a full-length black evening dress. She was already
dressed and he shook his head as he turned to the computer.
He dropped down in the seat and watched the man's cock cumming in that pink pussy
over and over again. He pulled his own hardening shaft free of the elastic band of
his shorts and began to stroke it, his eyes glued on the screen. The pleasure of his
hand, and the site of that cock squirting into the woman's pussy had him close to
cumming immediately. Suddenly he heard Barbara call to him from right outside the
office. He yanked his shorts back up over his throbbing cock.
"Hey Chris your mom called me and..."
She stopped talking as she stood in the door and could see the picture of the huge
cock ramming into the pussy on the screen in the moment before he could shut it off.
She took in the large budge in his shorts, the tissue box in his lap, and the scene
on the computer screen and a slow smile spread across her face. Chris could feel his
face heat up as he blushed.
"Um Barbara I umm..."
He turned in the chair to face her waiting for the diatribe that he was sure to come.
He hunched forward a bit to allow his loose shirt to hide his erection, but Barbara
just kept smiling for a moment. It wasn't a condescending smile but he couldn't place
what it conveyed either.
"Your mom called and said to meet her at the gym so I'll let myself out," she said in
a quiet voice.
Chris nodded unable to speak or think of what to say. He knew she had seen the porn
video and the erection in his shorts. There was a strange look on her face as she
glanced back down at his crotch before turning and walking away.
He woke late the next morning again, and the first thing to come to his mind was
Barbara catching him masturbating the day before. He had never been so embarrassed in
his life. He hoped she didn't tell his mom. He didn't think she had seen anything,
but he wasn't sure. He rose and went to the bathroom before getting in his shower.
After a quick wash and shave he headed over to the window in his mom's room and
looked down into the neighbor's pool. Ms Nelson was lying on a lounger in the sun
wearing a small black bikini and sunning herself. He felt his cock twitch instantly
in response to the sight of her.
Her tits looked even bigger in that bikini. Her body was much fuller and rounder than
Barbara's, and he thought she looked much more womanly because of it. She was facing
almost directly at him, but she had on dark sunglasses and seemed to be resting. It
almost felt like she was looking at him, but he knew when his mom sun bathed she
usually either was asleep or had her eyes closed against the glare.
He pulled down his boxer shorts and began to stroke his cock as he looked at her. He
began to get turned on at the memory of her bare tit the night before, and the sight
of them down below him only enhanced the memory. He began to stroke harder leaning
against the window as he did so, his eyes riveted on her sleek body.
The image of Barbara's ass bending over flashed in his mind and he suddenly imagined
her watching him as he jerked off in the office last night. He could feel the orgasm
building in him now, and he imagined shooting his cum all over Ms Nelson's tits. He
groaned as he began to shoot his load on the window, moaning as the first rope of
creamy white cum began to splash on the window pane.
At that moment he heard the toilet flush in his mom's bathroom that adjoined her
bedroom, and the door opened to reveal his mother in her business suit. She saw him
there with his hard cock in his hand, cum shooting from his cock all over her window.
He wanted to stop, to run, to hide himself, but his body was in control now. He stood
rooted, like a deer caught in the headlights as his cock continued to blast several
more loads of cum out and down the windowpane, the final spurt of cum falling onto
the floor at his feet. Chris's just stood there unable to speak or move, the
embarrassment almost overwhelming with his mouth hanging open.
His mother opened her mouth to speak, then closed it, then opened it again before
turning and walking back into her bathroom and shutting the door. He had never before
in his life been so embarrassed. 'What the hell is she doing home!' he thought as he
pulled up his boxers and struggled to wipe off the window and floor. 'God my mother
just saw me masturbating! How fucking weird!'
He finished cleaning the window, unable to get the streaks off without the glass
cleaner he had grabbed from his mom's bathroom yesterday. When he looked down Ms
Nelson was gone as well and he fled the room back to his own bedroom where he
proceeded to bury his head under a pillow.
He knew what would come next and he dreaded it. It didn't take long before there was
a knock on the door to his room and he heard the muffled voice of his mother call his
name. He pulled the pillow off his face and sat up with it in his lap.
"Yeah mom, it's open," he said, his heart already burning in his face.
'Mom looks as uncomfortable as I feel,' he thought. She opened and closed her mouth
several times before she was finally able to speak. When she did, it came out in a
rush of words.
"Look honey, I'm so sorry I surprised you there, and I know you must be embarrassed.
I am too. I stayed home this morning since I have to meet a client on this side of
town for a breakfast meeting." She paused only to draw breath. "Look that was nothing
to be embarrassed about okay? I know you must be mortified, I know I am, but don't
worry about it okay. It is a natural thing for all people, and especially boys your
He nodded his head wondering if his face would catch fire from the blood pounding in
his cheeks. His mom smiled then and seemed to regain some of her composure.
"Okay, good. Now let's forget about it!" she laughed, and he nodded again. The
tension suddenly lightened in the room. His mother turned to go, but checked herself
and turned back to him with a wry smile.
"Oh, but one other thing, don't let Mandy Nelson see you doing that while your
watching her or her husband will be over here trying to take it out of my hide, and
yours!" She laughed at what she obviously thought was a very funny joke as she closed
the door. He felt like he wanted to die.
The rest of the day was thankfully uneventful, and he made a point to keep his dick
in his pants. He ran over the last 24 hours in his head. He had maybe been seen
jerking off by his neighbor Mandy Nelson, and his mom's best friend had interrupted
him jerking off and maybe seen something, and then the worst of it, he had cum all
over his mother's window while she looked on. Then to top it all off she had given
him a little talk on it being okay, and joked not to let Mandy, the neighbor, see him
jerking off while he peeped at her! He figured if he never jerked off again it would
be too soon.
He was sitting on the couch in the living room as he read a book when he heard a
knock on the front door followed quickly by Barbara's voice.
"Anybody home? Shelly? Chris?"
'Shit!' he thought, he was not up to dealing with her after this day he thought. He
looked around, and jumped over the back of the couch laying flat on the floor behind
it. He felt slightly ridiculous laying there, but he thought he would feel worse
having to face Barbra after last night. She must be meeting his mom here again
tonight. They must be going to the gym every night now that they were training for
the triathlon his mom kept talking about.
He heard the soft popping sound of the refrigerator being opened, then the slap of it
closing. Barbara's shoes squeaked on the wood floor as she came into the living room
where he was hiding. Then he heard the leather creak as she sat on the couch in front
of him. 'Shit,' he thought, 'just my luck she decides to hang out in here.'
She let out a long sigh and he could hear the leather creek again as she lay down on
the couch. It was quiet for a bit and she figured she must be taking a nap or
something when he heard her make a small moan. He was immediately at attention. Could
he have heard that? Then Barbara moaned again, but this time louder, followed by a
few soft words.
"Mmmmmmmmmmmm. Oh yes. Ummmm."
'Holly Shit she is getting herself off!' He felt his cock spring to instant attention
and he started rubbing himself through his sweet pants. He could feel the couch
shaking a little now as she pleasured herself, her moans and cries getting more
"Oh fuck yeah that feels good, oh fuck, oh fuck!"
He couldn't help himself as he pulled his cock out and began to stroke himself
furiously. He had never been so turned on as he listened to Barbara get off a few
feet away. His cock was as hard as it had ever been.
"Fuck! Oh god I'm gonna cum, ohhh fuck yes!" Barbara was getting louder as he felt
her rock the couch slightly.
His cock swelled as his balls tightened against his body. The pounding of blood in
his temples and the tingling in his toes made him close his eyes tight as he felt his
cum shoot from his cock. At the moment he came he heard Barbara cry out a long low
moan and the couch shook violently. When he opened his eyes there was his cum all
over the back of the couch and his shirt, and he could hear Barbara breathing
heavily. The sound of the garage door brought him back to reality when he realized
his mother was home. He heard the leather creak again as Barbara sat up. Moments
later the door from the garage opened and he heard his mother's irrepressible voice.
"Hello? Chris are you home honey?"
"In here Shell," Barbara yelled nearly scaring him half to death.
"Hey girlfriend! How long have you been here?" His mom sounded like she always did,
more full of energy than any human being had a right to be.
"Just long enough to relax here on your comfy couch." Barbara's voice sounded
natural, even had a hint of laughter in it as she said this, but Chris's jaw was
His mom laughed,. "God I wish I had time to rest and have a drink, but we are late
for the trainer already. Get your smirking ass up and let's go!"