Awkward Moments


"Really? Why is that?" His mother asked with almost the sound of suspicion in her voice.

"Oh no reason.," There was a laugh hidden in Barbara's voice.

"Your thinking about yesterday! You leave my little boy alone, you!" His mom sounded genuinely angry.

"Keep your shirt on. I'm not going to do anything. Though that was quite a site!" God Barbara must have actually seen something. Oh shit, and told his mom.

"God did I tell you what happened this morning?" His mom's voice had the tone of someone wanting to share a piece of incredulous news. Chris groaned internally at what he knew was coming.

"No. What?" Barbara's voice had become serious.

"I stayed home this morning since I had to meet the Pernhow account downtown for a breakfast meeting, and I didn't want to double my commute. Anyway, I was in the bathroom getting ready, and I guess Chris didn't know I was home because when I walked out he was staring out my bedroom window buck naked at Mandy sunning herself next door, and masturbating!"

"You're kidding?!" Barbara sounded both excited and incredulous.

"I wish I was, and not only that, I walked out and I saw him cum all over my window. Then he saw me and I wanted to disappear, the poor guy was so embarrassed. Shit I was so embarrassed."

"Oh my god Shell, I think I need to touch myself. That is so hot." Barbara did sound a little excited, he thought, which was a new idea to him. 'She liked the idea of watching him jerk off?'

"Well exciting for you maybe, but mortifying for me. God I wanted to crawl under a rock and disappear. I'm his mother for Christ's sake! I wonder if he knows how embarrassed I was!" His mom sounded a bit exasperated. "First you see him last night, then I surprise him this morning, the guy must be a regular masturbating machine."

"God I would have loved to see that, though I would not have been able to stop myself from helping the poor guy. I swear last night when I saw how hard he was in his shorts I knew I had interrupted something and it took all my restraint not to go in and suck that poor hard cock." Barbara defiantly sounded excited now.

"You leave him alone Barb. He is still a virgin. I'm warning you okay, some things are off limits." His mother sounded strict now, it was her mama voice that he had heard many times.

"I will, I will, I don't want your wrath down upon me. Come on let's go, but I want you to describe every detail of this morning to me in the car. You know Mandy would go nuts knowing that he did that watching her; she is such an exhibitionist." Barbara's voice receded as they walked to the garage. He heard his mother's voice faintly before they disappeared into the garage.

"Yeah, she would be walking around naked out there if she knew that. I bet she would even..." her voice was cut off by the closing of the garage door.

A few minutes later he heard the garage door open and close and only then did he get up and clean up his mess behind the couch. He wondered what his mom was about to say. Apparently Ms Nelson, Mandy, had a thing for showing off. He would have to see if he could let her see him sometime. His head was spinning already, and this thought just made it more so. Not only did he listen to Barbara masturbate, but he heard her tell his mom she wanted to suck him! This was definitely a day he would remember.

The next morning when he awoke he made a quick inspection of the house to make sure his mom was gone. She had left him a note in the kitchen with 100 dollars telling him to get out of the house and have some fun. He planned to have some fun right here he thought to himself.

He ran upstairs and showered and threw his robe on before heading into his mom's room. The window was clean so he figured his mom must have cleaned it not wanting to make an issue of it by asking him to do it. He looked down to the pool next door and Mandy was just getting out of the water, this time wearing a white bikini that he swore he could see through. He dropped his robe and started playing with his already hardening cock. She stopped on the edge of the pool and dried off and he though maybe for a moment she glanced up at the window he was in, but he wasn't sure. He had a moment's hesitation before he threw caution to the wind and stepped right up next to the window in the warm sunlight.

Mandy walked over to the lounge chair and put her sunglasses on before laying down. He couldn't tell if she could see him or not but the sight of her lying there in her white bikini made it so he didn't care. He ran his hand up and down his hard shaft, his pre-cum lubricating his shaft for him. Then Mandy reached up and untied the bow between her large breasts and pulled her top away. There before him were her huge breasts, with their erect pink nipples standing up on top. His dick ached and he felt his orgasm building in him instantly. He shot a huge load of cum onto the glass in front of him. Unable to help himself he leaned forward as he shot his load smearing his cock and cum against the glass.

As he finished Mandy turned over on her lounge showing him her full ass and tan back. God how could an older woman be so incredibly hot he thought. He turned away reluctantly and headed into his mom's bathroom to get the Windex and tissue. He made sure he got the window perfectly clean before he left. Mandy didn't stay out much longer and quickly went inside only giving him a glimpse of her breasts again.

He spent the rest of the day thinking about Barbara and what she had said the night before which necessitated several more wasted tissues in his room. He was turned on by the thought that she thought he was sexy, and he wanted to try to do something to encourage that. He especially wanted to hear her masturbate again. In fact he wanted to see her masturbate.

He dug out the video recorder and found a place to hide it on the bookshelf where in the dim evening light it would be invisible. He then set about testing it until he had it focused to record a perfect picture of the couch. He knew he was being a pervert, but he didn't care, all the events of the last few days were making him crazy.

After he had the camera set up, he sat at the computer and used his mom's $800 web cam to record himself jerking off. The cum shot all the way up onto his face he was so turned on. Then he took some screen shots of him cumming, and printed them out on his mom's photo printer. Then he printed out an assortment of the porn he had saved to his pictures directory. He stuck all the pictures and a few of the penthouse magazines he had into a binder which he wrote "Private" on the front of in big bold letters. He would then leave this strategically on the couch for Barbara to find. If this didn't get her horny enough to touch herself, he didn't know what would! He congratulated himself on his ingenuity before having a lunch of Totino's pizza and coke.

When the evening rolled around, he hid behind the couch with the remote for the camcorder and his fabricated notebook on the couch. He was more nervous then he had ever been. If he got caught doing any of this he would be in so much trouble his mom would kill him!

About 5:45pm the doorbell rang followed again by Barbara's voice.

"Anybody home? Chris you here? Shelly?" He ducked down behind the couch his cock already growing in his pants.

He could hear her walking again to the kitchen then into the living room as she had the night before. There was the sound of her dropping her gym bag on the floor then the creek of leather as she sat down. Something scraped on the leather, and he thought maybe she had picked up the binder he had stuffed next to the pillow on the end.

"Oh my god!" He heard Barbara moan out in a low husky whisper. He pushed record on the camcorder remote as he heard the rustle of paper while she leafed through the pages. "Oh Chris you naughty boy."

He nearly jumped out of his skin when he heard the garage door opening as his mom got home. 'Shit mom, of all the nights to get home early!' he thought.

"Shit!" he heard Barbara exclaim then he heard the sound of her rising off the sofa and the zip of her gym bag.

Her shoes squeaked as she walked out to the door to the garage, and a few minutes later the garage door hummed as it closed as they left for the gym. 'The best laid plans of mice and men.' he thought when he stood up. Then he noticed that the binder was gone. 'Oh no.' he thought, he hadn't expected her to take it with her.

He walked up the stairs and looked out the office window, and the lights were on in Mandy's bathroom and bedroom. He waited watching through the window until he saw her walk into the bedroom from the bathroom. She was completely naked and her large breasts looked fabulous as she towel dried her hair and they bounced around to the vigorous motion. Chris grabbed the office chair, and remembering his new found boldness, turned on the dim desk lamp so that he would be slightly visible in the dark room. He dropped his shorts freeing his erection and began to stroke it slowly looking out the window.

Mandy continued to dress her eyes drifting past the window. Did he imagine it or had she done a quick double take? He continued to stroke himself as she sat down on the bed facing him and began to brush her hair. His cock was already aching at the sight of her naked before him, the beautiful fall of her breasts and her long brown hair. He could see the dark hair between her legs as he stroked himself, and he felt his excitement starting to build. She sat as if staring absentmindedly out the window, and he wondered if she could see him at all with the glare of the bright light in her room. If she could, she gave no indication of it.

She reached to her night stand and grabbed a bottle of lotion and pouring a liberal amount onto her hand she began to massage it into her breasts and body. He was in ecstasy as he watched his cock leaking pre-cum as his hand pumped faster and faster. Then she spread her legs and he could see the glistening moistness of her sex as she spread the lotion down her thighs and calves. His whole body shuddered as the site of her pussy pushed him over the edge and he came with a loud moan, his cum shooting out into the light cast by the lamp in long bright white arcs of pleasure.

He sat back in the chair and took deep breaths as he looked across at his neighbor. She was looking at him now. There was no doubt about it this time, she was smiling too as she looked across the dark expanse between their houses. He knew she had just watched him cum for her, and the thought made him tremendously excited. His cock which had begun to soften began to grow hard again, and he reached down and began to fondle it as they stared at each other. Her smile grew a little more and he could see her nipples harden on her full breasts. Then quickly as if she had made up her mind she stood and walked to the bathroom taking her robe from a hook on the door and throwing it on. He felt his excitement sputter out as she turned and walked from the room.

The next morning he woke at his usual late hour and once again made the rounds of the house. There was a note from his mom saying she would probably be late tonight again, and to leave the door unlocked for Barbara if he went out. He was a little disturbed about the fact that she had taken the binder with her. What if she showed it to his mom? He shook his head; he didn't think she would do that. He wondered if she intended to keep it. She should figure that he would miss something like that.

He ate a quick breakfast before heading to his normal morning perch by his mother's bedroom window but was saddened to find Mandy was not pool side. He was about to give up when he saw someone else emerge from the house and cross to the pool. It was Sabrina in a lime green bikini. He stepped back from the window a little in shock and watched as she lay down in the same chair her mother had been in the previous morning. She had large breasts and full hips like her mother but was quite a bit taller, and her long legs and shapely neck gave her a gracefulness. She must be home for the summer he thought his hand almost instinctively falling to his cock as he looked at her laying in the sun.

Some motion caught his eye and he looked across to the house and the window of what looked to be an office, and was surprised to see Mandy opening the window shades and smiling at him. She was wearing her bath robe and as she saw him she quickly dropped it to the floor striking a pose and motioning for him to do the same with his, which he did without hesitation. His cock was rock hard as it stood out in front of him. He started stroking himself while he looked at Mandy but she shook her head and gestured that he should look pool side.

He looked down and his mouth must have fallen open as he saw Sabrina completely naked smearing oil on herself in the lounge chair. Her body glistened with the oil, and her completely shaved pussy could be seen even from his high vantage point. He watched as she spread the oil evenly over her body and large breasts, her hands stopping to pinch her nipples a few times before she lay on the chair her legs slightly spread allowing him to look at her pink smooth pussy.

His hand moved of its own accord as he looked at her, his cock so hard he felt like it would burst. He wanted to touch her smooth mound, to run his hands over her oiled body and pinch her brown nipples. His hand moved faster as he imagined grabbing her firm tits, and sucking on those hard little nipples. He leaned against the window forgetting his caution as his passion grew. He glanced over at Mandy in the office next door and she was stroking her clit as she sat in the office chair watching him get off on her naked daughter. The sight of her naked with her fingers shoved in her hot slit was too much for him and he shot his load over the window in a triumphant moan. He looked back down to the pool and Sabrina was sitting up holding her towel over herself and glaring at the window where he stood with his leaking cock in his hand.

She shook her fist at him before swiftly retrieving her bathing suit and heading for her house. 'Oh shit, I am in so much trouble,.' He thought. He looked to Mandy who was sprawled in the chair with her head thrown back and her hand still lightly resting on her now very wet pussy. She had obviously cum as hard as he had. He waved to her to try to get her attention but she seemed lost in the afterglow of her own pleasure. Suddenly she looked up as Sabrina came in the room still clutching her towel and looked at her naked mother spread eagle before the window, then looking across to the cum streaked window. At first she looked livid then he could see her mother talking to her and she shook her head in amazement. Then they both broke out laughing. Sabrina looked back to her mother and he could see them talking when Mandy nodded her head at the window. Sabrina smiled.

Sabrina walked to the window and put one leg on the ledge and pulled her pussy open with her fingers giving him a perfect view of her glistening slit. He felt his cock stir again and stepped up to the window to stroke his hardening meat for her. She immediately seemed to get into it as she saw him back in the window her fingers rubbing furiously on her shaved pussy. His cock grew hard again as he watched and stroked himself again.

She began rubbing her tits and pinching her nipples with one hand as her face contorted with pleasure. He could see Mandy behind her pleasuring herself again as she watched her daughter getting him off. He could feel another orgasm building in his aching cock, and Sabrina seemed to quicken her stroking as he did. He heard her scream even through the windows as she came and he shot another load of cum onto the streaked glass. His legs nearly failed him as he stood trembling against the window frame. Sabrina looked across at him and blew him a kiss before reaching over and drawing the curtains. This summer was certainly looking up he thought.

He was excited to see what Barbara's reaction would be to the pictures she "found" last night, but he was torn on if he should meet her at the door, or hide behind the couch again to see if he might get lucky with the camcorder. As it approached 6pm, his nerves failed him and he took up his position behind the leather couch. She arrived in the usual manner just after six, and he heard her walk into the living room after her trip to the kitchen for water.

The sound of her gym bag was distinct as she dropped in on the hard wood floor. He heard her unzip the zipper as she pulled what must be his fabricated binder from her bag. There was the sound of pages turning again and he figured she was going to take one more good look before she stuck it back on the couch.

"Oh Chris you bad, bad boy." The sound of her sitting on the couch was amazingly close as he lay there. "Ummmm, ohhh god I need to cum..." she moaned and he thanked the gods wondering what his camera would show him later.

He pulled down his sweats as he stroked his cock with increasing force. Her moaning increased almost at once and she let out another exclamation.

"Oh Fuck! Oh yeah cum, cum, cum!" she yelled as Chris was forced to slow his stroking on his cock in the quiet after her rapid orgasm. She must have been really horny to cum that quick he thought, and after all the action his cock had seen lately it would take a little more for him to cum this time. He didn't mind as he figured the video he would be watching later would be more than ample to get him off.

"Oh that was good. Now what to do with this little naughty book so bad boy with think he just misplaced it."

She was talking to herself, but he thought she sounded incredibly sexy as his hand continued to slowly stroke his throbbing cock. He heard the creak of leather and suddenly he was looking up into Barbara's blue eyes as she leaned over to deposit his binder behind the couch. She took in the entire situation and instead of screaming, which Chris fully expected, she smiled. Her eyes locked on his swollen cock and she licked her lips as she smiled.

"Stand up mister, right now!"

Her voice left no room for argument as he struggled to rise with his cock waving in front of him rock hard. He fished for his sweat pants but somehow he had managed to kick them under the couch in his ministrations to his cock. As he stood he saw her workout shorts on the floor, and that her lower body was completely bare and his cock twitched at the site of her. She smiled and looked down at his raging hard on.

"You have had this coming to you mister,." She said and in one fluid motion leaned forward and took his cock in her mouth.

He felt the incredible warmth of her mouth as she leaned over the back of the couch and sucked his cock, bobbing her head up and down his shaft. He was in pure heaven. He realized her naked ass and pussy were facing right at the camera as she sucked him and he felt the cum already boiling to the top of his cock.

"Oh god Barbara I'm going to..." his sentence faded into a moan as his cum shot into her mouth and she sucked it from him, her eyes now looking up at him as she swallowed every drop of his cum

.He had never felt an orgasm be so powerful, even this morning while masturbating for Sabrina and Mandy. She sucked him until he had completely stopped cumming then let his cock slide from her mouth with a soft pop. She smiled at him and sat back on her legs with her hands on her hips.

"That will teach you to tease me!" She said with a sparkle in her eye. At that moment the sound of the garage door opening could be heard. "Quick, lay back down!"

Barbara looked truly alarmed and he dropped to the floor, which was not difficult considering the state his legs were in after that. 'God Barbara gave me a blow job!' he thought to himself. He couldn't believe it. He heard her quickly pull on her gym shorts and the quick squeak of her shoes as she walked across the room to the garage door to meet his mom.

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