tagFirst TimeAwkward Moments

Awkward Moments

bySolitary_Thinker©

'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.

"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 age. Okay?"

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 intense.

"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 hanging open.

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!"

"Okay, okay, keep your shirt on." He felt the couch shift as Barbara rose. "Where is Chris, I could have used his help a minute ago,." Barbara said again with a laugh in her voice.

Report Story

bySolitary_Thinker© 0 comments/ 471192 views/ 69 favorites

Share the love

Report a Bug

Next
6 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel