The Lucky Paper Boy

Payton Wade had decided many years ago that he was, in fact, the luckiest person on the face of the planet. As a child, he’d always won the prize or got the extra cookie and out of trouble; as he grew older, he found he could con the girls into showing him their undies and letting him touch their tits after school. And when he turned sixteen, and the need for sex was starting to get to him something fierce, Payton Wade met Mrs. Jessica Ramsay and thus cemented his notion that he was, in fact, the luckiest person in the world.

It was his third week of throwing papers, and he was beginning to think the job wasn’t worth the $145 paycheck he got at the end of the week, especially since it seemed his route got another ten extra houses every day. By the time he was halfway done with his route that Monday, he was giving serious consideration to quitting. The heat and the dog bites were starting to irritate him, and the dumpy housewives with their inability to tip his undeservedly good service were beginning to really piss him off.
The last house on his route was a squat colonial with a clean, small yard and a garden of cacti on the corner. He liked this house best for a couple of reasons: no dogs, and Mrs. Ramsay always tipped…and her daughter was fucking hot. Feistay Ramsay may have had the stupidest name in the phonebook, but she had a face to stop traffic and a body that wouldn’t quit. He watched her bound onto the bus for her rich little private school in her unbelievably sexy uniform during the week, and got to talk to her on the weekends as she paraded around the front yard in skimpy shorts and tank-tops. He’d love to feel her up behind the gym, but with the two of them going to separate schools and her large angry father watching him like a hawk, the chances of getting to second base with Feistay Ramsay were slim to nil.
Still, he savored the little thrill of watching her climb the bus in her little plaid skirt and tight red blazer, and waved an innocent hello to the hawk-eyed father as he went off to work in the most beautiful black Porsche Payton had ever seen. Lost in a naughty fantasy that involved Feistay on her knees in the front yard, Payton didn’t realize he’d set the paper down on top of Mrs. Ramsay’s feet. He jumped when she chuckled.
“S-s-sorry Mrs. Ramsay…didn’t see you there.” He stammered; the stutter was part of that innocent charm girls seem to always fall for.
The older woman chuckled, and patted him on the shoulder.
“That’s all right Payton. I expect you were ogling either my husband’s car or my daughter.”
He flushed, noting the tip of a white envelope sticking out of the pocket of her bathrobe. He was pretty sure his tip was in there, and he didn’t want to piss off the old woman before he got his hands on it. Then he noticed that Mrs. Ramsay’s robe wasn’t cinched very tight, and that the black lace cups of her bra were running over. He tried to spit out an apology, but could only utter an unintelligible ‘uh…’ as she bent down to pick up the paper.
She was smirking as she straightened, and gave him the once over. The look was cold and piercing, and he was pretty sure she could see his hard-on. “Are we your last house?” she asked.
He nodded, shifting the now-empty tote bag to cover up his bulge.
“Why don’t you come inside for a drink? It’s so hot outside.” She said throatily.
“I really couldn’t. I’ve got to uh…um…” but he couldn’t really think of anything he had to do.
“Are you sure?” Mrs. Ramsay asked, holding the paper in one hand and playing with the belt of her robe with the other.
Payton licked his lips. “A drink sounds good.” He mumbled as Mrs. Ramsay turned around and sashayed inside. He watched the sway of her hips and thought she looked pretty damn good for having had a kid.

The interior of the house was dark and cool; the shades drawn against the invasive desert sunlight. Payton took off his cap but not the tote as his cock was still firm enough to embarrass him. He sat on the couch as Mrs. Ramsay suggested, and she disappeared into the kitchen, returning with a tall glass of pink lemonade. She sat on the couch next to him, curling her feet under her and giving him a nice view of her breasts as the robe fell open. He gulped down half the lemonade, unable to take his eyes off the lacy bra.
“You know, my husband’s a doctor.” She said out of nowhere. “He works long hours, and is usually home late.” Mrs. Ramsay said with a pout.
“Still, it looks like a pretty good life.” Payton replied, feeling foolish. That was why he liked dealing with girls, especially the ones younger than him. They were stupid and thought he was super suave.
“Oh, it is, but I get so lonely.” She put her hand on his knee, and gave it a gentle squeeze.
Payton’s voice caught in his throat as her hand traveled halfway up his thigh. “Uh…Mrs. Ramsay?”
“Call me Jessica.” She murmured, palming the front of his jeans.
He couldn’t believe his luck; his undeniably wonderful, fan-fucking-tastic luck. The old girl was horny as hell, and he was going to get to live a letter to Penthouse. Not wanting to run the risk of Mrs. Ramsay changing her mind, he put the glass on the coffee table and grabbed both her breasts, running his hands over the smooth skin and taut black lace.
“No, no, no.” she said, and for a second Payton’s hopes were looking crushed. “Gently; you’re touching a woman, not a carburetor.” She held his wrists and moved his hands in slow, languid circles all over chest.
He licked his lips, and pulled one of the lace cups down so the tit inside could bounce free. He caught the nipple in his teeth and to his surprise heard Mrs. Ramsay squeal happily.
“Yes! Now suck it; hard!” she commanded, and he obliged. Her skin was silky and fragrant, the bath powder she used tasting sweet as sugar. He pulled at the nipple with his teeth, pinching the other nipple through her bra. The fabric went slack, and was gone.
Payton sat up, and watched as Mrs. Ramsay pulled the bra off. She had fabulous tits for a woman who had had a kid. They were big and jiggly, the nipples dark and stiff and large. He put his hands under them, and pushed them together, and then up and then nearly creamed his shorts when they jiggled back into place.
“Fan-fucking-tastic.” He breathed.
“That’s always appreciated.” Mrs. Ramsay said with a breathy giggle. She unfurled her legs and stood. “C’mon.” she said impatiently, walking towards the bedroom. Payton watched the black lace of her panty disappear between two perfect white globes of flesh that shifted as she walked. The bathrobe had hidden a great ass; he wondered how often she worked out. He decided he didn’t really care at that moment as he leapt from the couch and shed his clothes, snake-like, on his way to Mrs. Ramsay’s bedroom.

She was on the bed waiting for him, grinning widely. “Smart boy, ditching your clothes before you got here. But I have a present for you to put in your little paper bag.”
Payton watched, awestruck, as Mrs. Ramsay raised her hips and slid off her naughty lace panties. When she handed them to him, he noticed the crotch was sopping wet. Again, he nearly creamed himself. “Seriously? I can have’em?”
She nodded. “Every boy should have a naughty little reminder of his first time…this is your first time, right?”
“Um…I’ve seen a lot of titties.” He admitted. “But nobody every let me suck’em and sure as hell nobody ever gave me their panties.”
“So you’ve never seen a pussy?” she asked.
“Not up close…I mean, like I seen’em in porn and stuff.”
“Go tuck that in a safe place, and I’ll show you a nicer pussy than you’ve seen in porn.” Mrs. Ramsay murmured.

He had the panties stowed and was back in the bedroom in what he thought was record time. Mrs. Ramsay was lying across the bed, her legs spread wide with the fingers on her right hand moving methodically up and down her pussy. “Come and take a look.” She said.
Most of her pussy was smooth and bare, save for a tiny landing strip of curly blonde hair. The skin was pale and free of stubble. “You’re right…” he said, rubbing the back of his neck with one hand. “It’s definitely the nicest pussy I seen.”
“Do you want to fuck this nice pussy?” she murmured.
“Hell yeah!” he said enthusiastically.
“Do you think it’s wet enough to fuck?”
“Looks wet to me.” Payton didn’t relish the thought of having to chow down; something told him he was not the first guy to be seduced by Mrs. Ramsay and the thought of maybe accidentally munching some of Mr. Ramsay’s leftover jizz made him nauseous.
“Why don’t you put your fingers in it and check?”
He grinned. Finger-fucking he could handle. Sure touching another man’s jizz would be gross—because he wasn’t sure if Mrs. Ramsay had washed up after servicing Mr. Ramsay that morning—but it would be better than eating it.

At Mrs. Ramsay’s urging, Payton managed to get four of his fingers into her pussy. It wasn’t so much a tight fit that kept his pinky out, but the awkwardness of trying to keep his pinky in that resulted in a hit-and-miss sort of situation. Still, Mrs. Ramsay was enjoying herself and Payton was almost wrist-deep in sweet pussy action. He felt around, looking for all those naughty little buttons and knobs the women’s magazines talked about. He didn’t feel anything but spongy wet flesh, but he wasn’t about to complain. At any minute Mrs. Ramsay might get pissed and he was within sight of the finish line, so to speak.
“My husband hasn’t touched me like this in months.” She moaned, bucking her hips against his hand. “You’re doing really good kid.” She added.
‘If you say so’ he thought, but kept to himself. “I think I’m gonna bust a nut here soon!” Payton groaned, gesturing to his throbbing penis. All the near-jizzes had left a build-up of white cream on the tip, and he half-hoped Mrs. Ramsay would lick it off before he got inside her.
“Well we can’t have that, now can we?” she said sweetly, grabbing his wrist and pulling his fingers out.
It didn’t look like she was going to suck him at all, but Payton wasn’t that fussed. She was lying on the bed with her legs spread, pulling her pussy open wide for him; only a fucking retard would risk blowing his chance for sex by complaining.

He knew he couldn’t come just yet, but Christ it was hard! She might not have been virgin-tight, but there was some good pull left in the old girl, and she was so fucking hot for him! Her legs were around his waist and she was saying all sorts of nasty shit; he bit her tits when she asked, pulled her hair when she ordered; tried to slap her ass but didn’t want to risk falling out of her.
When she came, it was great; she got so tight for a second, but the feeling was gone before Payton really got to enjoy it. Still, she let him hump her and he got to shoot right in her pussy. When he pulled out, there was a little strand of cum going from the head of his dick to her pussy, and he felt kind of proud; like a man’s man.
“That was great!” Mrs. Ramsay breathed, looking up at him proudly. “You may not have the biggest dick, but you’ve got talent.”
“Um…thanks.” He said, a little annoyed that she’d say something like that after how hard he tried to please her.
“Your tip is in my robe on the couch…think you can have another drink tomorrow?” she murmured, running her hands over her tits, cupping them and pinching her nipples.
More than a little displeased at the shoddy turn of events, he shrugged. “I have school tomorrow.” He said as he walked out the door to gather and put on his clothes. Payton wasn’t ungrateful the old broad had busted emblematic cherry, but did she have to treat it like all he’d done was carry her groceries inside for her?
Mrs. Ramsay had gotten up and was following him around the living room as he dressed. She was pouting. “Aw…well the next time you have some free time, why don’t you keep me company?”
He shrugged. “Maybe, if things are right.” He said vaguely, reaching into his paper bag to make sure the black lace panties were still there. If push came to shove, when he jacked off with them he could pretend they were Feistay’s; that’d be hot.
“Well…thanks for the fun.” She said, coming up behind him and kissing his neck as she groped for the fly on his jeans.
“Yeah, you too.” Payton replied, shrugging her off and going out the door. When he was halfway down the sidewalk, he looked back to find naked Mrs. Ramsay leaning against the doorjamb. He waved and she waved back before going inside. Sure she’d treated him like some kind of male hooker, but it was pretty cool that he’d lost his virginity. It was worth keeping the lousy paper route if he got to bang Mrs. Ramsay on a regular basis.
Maybe next time, he could convince her to do it in Feistay’s room…

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