'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 phone rang.
"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 door.
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 her."
"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 bulging shorts.
"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.
