John was the typical high school loser, and he knew it. There were a variety of reasons for his lack of popularity, but he knew insufficient confidence was at the top of his list. He was a little less than average height, scrawny, and as far as he was concerned, not particularly handsome. He had friends—other high school losers—and they were all guys. Because most of all, John was shy.
Girls made every guy nervous at his age, and he knew that, too. But John was afraid to talk to girls even if he wasn't attracted to them. Girls were just a different species, and it might as well have been an undiscovered one. He had hoped he'd grow out of this nervous phase, but even at 18 and the oldest senior in his class, he was still the most socially awkward.
For the millionth time, John pondered these problems as he sat alone in his room on the first day of an extended weekend. It wasn't actually a weekend--he had just gotten home from school—but he considered it so because the rest of his family had gone away to visit family for the week, leaving him alone, which is how he liked it.
He was supposed to be staying with his aunt who lived across town because his parent's didn't want him to be alone all that time. Not that they didn't trust him, but they felt bad about leaving him all alone while they had their vacation. But John had too much homework and too many tests this week to skip, and so it was his choice to stay. And his aunt respected his desire to be alone, so she promised she wouldn't tell if he wanted to be in the empty house all week, which of course he did.
After all, since John couldn't get girls, the only way he could get off was to masturbate. And when you live in a house with parents and three bitchy sisters, finding time to masturbate wasn't easy. John would be sure to take advantage of these lonely evenings in his own way.
In fact, as he walked to his parent's bedroom, John was ready to release some of that pent up energy already. Even though he was old enough to but all the porn mags he wanted, John liked sneaking his father's magazines every once in a while. For years, when porn was unavailable to him for purchase, the only way he could get it was to sneak one of his old man's Penthouse or Hustler mags from under his parent's bed. So now, checking out those same pages was kind of like visiting an old friend.
John reached for the small stack and took the top two. One was one of the classics that had helped him through those tough years before he had a computer with Internet access in his room. The other, however, was a brand new issue, and John's eyes lit up with excitement. Already flipping through the pages, John rushed back toward his room.
But he never got there. As John passed through the living room on his way to his bedroom, he saw a car drive past through the big picture window. John lived near the end of a dead end street, so traffic was unusual, and he looked up to see who it might be. He recognized the car immediately. It belonged to the girl across the street, which John had been crushing on, some would say obsessing over, for some time now. Her name was Katie, and she had been gone for a few days, and John was more than happy that she was back just in time for his vacation from the family.
He stopped in front of the picture window and watched, knowing that the sun and shadows at this time of the day would keep her from seeing him from all the way across two yards and a street. He watched as she got out from the passenger side, and her mom got out from the driver's side—apparently mom had picked Katie up at the airport. Together they pulled Katie's luggage from the trunk, then headed inside.
She was a hundred feet away, but John had seen more than enough to be turned on. Without even thinking, he dropped the old magazine and plopped the new one on the table in front of the picture window. Flipping through the pages of ads to get to the good stuff, John felt himself stirring quickly to life.
He passed a pictorial full of college girls wearing cheerleader outfits (usually just the tops or just the bottoms, of course) and was trying to stop to turn back when he caught a glimpse of another pictorial that simply blew his mind. The young woman in these photos was strikingly beautiful, but most importantly, she could have been Katie's sister. From their bodies to their facial features, the model on the pages and the girl across the street were so close John new he'd have to go out and buy his own copy of this issue ASAP.
Katie was 22, and John guessed the model to be about that age, too. They both had thin, tight bodies, and though the model's breasts were definitely bigger, Katie's were by no means small, and definitely perkier. Both girls had unbelievably tight, mouth-watering asses, and legs you'd pray to have wrapped around you. The girl's also shared blue eyes, though John was certain Katie's were bluer, and both had long, brunette hair, though Katie's had colorful streaks of dye in hers.
Unable to take his eyes from the model, or get his imagination from the neighbor girl, John undid his pants and pulled out his already erect dick. John felt his penis was both a curse and a blessing. A blessing because, for his body size, his dick was quite large when erect—almost seven inches, and thick, with big, heavy balls. But it was also a curse because it would've been just another thing to leave him alienated if the others at school found out. Even jealous jocks with small dicks would be able to spin John's gift so it would seem more like a freak show. And though John fantasized about sex often, he was scared to try it, fearing if he did, the girl would forget his size and focus on his inability to use it.
But none of that mattered here, alone, with Katie-the-hot-neighbor-girl's nude look alike. John stroked himself into a frenzy, drooling over a picture of the model bending over and letting her breasts hang from her body as she smiled seductively at the camera. He jerked himself so hard and fast that his pants fell down to ankles. But he was so into it that he didn't care.
"Oh Katie," he grunted, feeling his warm precum slide into his hand and then around his dick. "I want you so fucking bad..."
He was getting very, very close.
Then, suddenly, John caught movement out of the corner of his eye. He looked up, jolted by a "bang" that was probably not very loud, but sounded much more intense. Before he could focus on what was going on and decide how to respond to it, it was already too late.
In front him, separated by less than three feet of space and under an inch of glass, was the mail carrier.
John hadn't paid much attention to the mail carrier. Honestly, who did? But he had been interested enough to acknowledge that she—yes she—was probably the best looking mail carrier he'd ever seen. That might not be saying much, since most other female mail carriers he'd seen were old and/or brutally ugly.
But Molly—John's mom had learned her name—was actually pretty attractive. Sure, she was older, between 35 and 40, but John was into that. And she wore shorts on her route as often as possible, giving her a chance to show off her long, tanned, sculpted legs and giving those on her route a chance to admire them. Even in cold months, as now it was October, Molly wore those shorts through as cold of temperatures as she could handle, and she could handle more than most.
She wasn't thin nor fat, but a tall, full-bodied woman with all the right curves in all the right places. Molly wouldn't win any beauty pageants, put if she took off the unflattering postal uniform, she would definitely be pin-up material. She had a big smile, long blonde hair, and always wore sunglasses. John had never actually seen her eyes.
But he knew her eyes were on him now, because this attractive older woman who he'd never paid much attention to before had suddenly snatched up all of it. Stepping away from the mailbox, which was next to the picture window, Molly stopped dead in her tracks, dropped her jaw and stared at John with disbelief.
What could he do? He was caught red-handed...or was it fisted? There was no hiding what was happening, but he could at least hide from her leering sunglass lenses. He moved to run way, his face already beat red with embarrassment.
But Molly surprised John again when she smiled that big, beautiful smile. Even after that, he expected her to move along. She would be either embarrassed by what she had seen, or would feel sorry for her accidental intrusion. But she stayed. She actually moved, planting her feet in place and turning and bending closer to the glass, holding a hand over the edge of her sunglass to shield the sun so she could get a better view of...everything.
John stood frozen, petrified. Not knowing how to react, but knowing his body was beginning to shift its energy from fear to something else...
Molly stood like that for a few moments longer, then cocked her head, shifting her gaze so her lenses connected with John's eyes. She smiled again and gave an exaggerated shrug, as if to say, "Well?"
Her meaning was obvious, but John still couldn't grasp it. Molly was in perfect position to just walk away, but her she was, standing in front of the window, actually waiting for him to continue jerking off. His cock had shrunk at the scare she gave him when he first noticed her step into view, but it was quickly regaining its rigidity. Slowly, cautiously, he grabbed the base again with his fist and waited for her to respond.
She smiled and nodded, then straightened up from the window and folded her arms across her chest. When John didn't move, she gave the shrug again—"Well?"
John had grown fully erect just from the attention, the knowledge that he was hard and naked in front of a woman for the first time in his life arousing him significantly. He began to jerk himself, starting slow, but immediately losing control. He wanted to put on the show that Molly was obviously expecting, but he was too scared to make this a bold performance, and too on edge to draw it out. He pumped his cock faster and harder, taking short, deep breaths and never taking his eyes off of her.
Though he was obviously nervous and inexperienced at the art of seduction, Molly seemed to be thoroughly enjoying the show. She smiled wide, nodding approval while giving occasional glances from side to side, checking to make sure there were no other spectators. The house had large evergreens at both front corners, so the window was reasonably protected from prying eyes.
John felt so hot and horny that his legs buckled, and he grasped the table in front of the window with his free hand for support. He looked Molly up and down, lingering on the bare skin at her thighs and then at the significant bulges at her chest. He then saw her step closer to the window, drop the mailbag from her shoulder, and put her hands to her breasts, squeezing and pushing them together. Her uniform offered little opportunity to spot cleavage, but the idea was there, and just the fact that she was doing this was more than enough to draw John's load from deep in his balls.
He felt the rush throughout his groin, and stiffened as it raced up his shaft. He opened his mouth, calling out loud enough to be heard through the glass and pointed his cock at the window. Then, with perfect timing, Molly bent over and pressed her lips to the glass, kissing it. John erupted, spewing a week's worth of cum all over the window right where her lips remained. His cock spit long string of the white stuff, and he would've coated her face if not for the window. And judging from her smile as she pulled away, she would have let him, too.
Before that last drops of sperm had even finished oozing from John's cock, Molly was picking up her bag and getting back to her route. It had all happened so fast. Too fast. But before she left the window, she looked back to John, smiled big, and gave a thumbs up. And then she was gone.
John pulled his pants up, then ran from window to window, trying to catch more glimpses of Molly as she finished the house on his block. His body was shaking from the anxiety of what he'd just been through. He wondered if she would look back at him, too, but nothing she did seemed out of the ordinary, as if helping along a young guy jerking off in his living room was just part of her job. Though she now looked unusually sexy doing it.
After she had disappeared, John returned his dad's magazine, then fetched some paper towels and window cleaner from the kitchen pantry. He cleaned his cum off the window and the sill. When he was done, the pink stain of Molly's lip prints were still on the glass. John's cock twitched excitedly in his pants, and he became very thankful that tomorrow wasn't Sunday.