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Disclaimer: This story and all characters are fiction. All characters are 18.
Phillip watched Donna through his living room window, as she talked to his mom and dad in the fading light. After his parents got in the car with his sister and drove away, he continued watching Donna in her yard, smoking a cigarette. The pretty brunette neighbor must have just arrived home from work, looking dressed up in her black skirt and white blouse. Philip was told that Donna was over fifty, but it was hard to believe. She was so slender and trim. Just look at those legs! And she has grandchildren! Everything about her, her walk, her movements, her hairstyle, exuded sex appeal. Alone in his house in the dark, peeking through the window, Phillip started rubbing his teen-aged dick through his slacks. When Donna entered her house, he kept watching. He had never come close to seeing Donna naked through the window, but he kept trying. He had seen her in a short nightgown a couple of times, and once in a bathing suit, but that was about it.
Phillip watched Donna in her kitchen, pouring herself a drink from a liquor bottle. She seemed to absent-mindedly stare out the window, but when she looked over towards Phillip’s window, he ducked back. He watched for another five minutes, but Donna wasn’t in a hurry to change, so he left the window. Not three minutes later, the phone rang.
“Hello, is this Phillip?”
“Hi, this is Donna, from next door.” Phillip’s heartbeat picked up. He had only talked to Donna a few times in the presence of his parents and her husband. He had never talked to her on the phone.”
“Is your mother there?”
“Will she be back soon?”
“No. They won’t be back until after eleven.” Phillip thought it strange that Donna would see his mom drive away, then immediately call looking for her.
“Oh. So you’re all alone tonight?”
“So am I. My husband won’t be back until real late. So how are you Phillip, I never get to talk to you.” Donna’s voice was low and a little sultry.
“Got any plans tonight?”
“No. Just watching TV.” And watching you, he thought.
“Me neither. I stopped off for a drink after work, and just got home. You don’t have a date tonight?”
“Do you have a girlfriend?”
“You’re a good-looking young man, I was watching you out in your yard the other day.”
Phillip’s cock jumped. He couldn’t believe a woman approximately three times his age was checking him out. “Thank you.” He didn’t know what else to say.
“You’re pretty quiet, aren’t you?”
“I’ll bet you’d get lots of girls if you tried. Sometimes if you just ask a girl a direct question, you’ll get what you want.”
Phillip sat in the dark with a hard-on, but could only shyly grunt an affirmative to the married neighbor that he had jacked off so many times while thinking about.
“Have you ever watched me through your window?”
“Uh, I’ve seen you outside.”
“It’s OK to tell me. I won’t tell anyone. I thought maybe I saw you in the window once or twice. Don’t you look at me?”
“Well, yea, a couple of times.”
“Well, I’m flattered that an attractive young man like yourself would show me any interest at all. Do you think I’m attractive?”
“Oh, sure, yea.” Phillip restrained himself from divulging how hot he really thought she was.
“Well, thank you. I’m looking at your house, and I don’t see you. What room are you in?”
“I’m in the living room,”
“I’m upstairs. Why don’t you come upstairs? Are you on a cordless phone?”
“Yea. I’ll go upstairs.” Phillip sprinted up the stairs two at a time. Looking kartal çıtır escort out the upstairs window, he could see Donna clearly in her upstairs bedroom, with the lights on, standing in the middle of the room. She had her cordless phone to her ear, and a drink in her hand, still in her blouse and skirt.
“Turn on the light.” Donna requested. Phillip turned on the light and stood in the middle of the room. He and Donna were watching each other through their windows, each with a phone up to their ear. Donna waved at Phillip and said, “Hi” in the phone. Phillip waved back. “You’re getting big. How tall are you now, Phillip?”
“I’m about five-foot-six.”
“That’s pretty tall for your age. That’s how tall I am.” From fifteen yards away, Phillip watched the slender, mature woman watching him. “I really need to get out of these work clothes. You know, from here, you’re the only person that can see me. Would it bother you if I changed?”
“Uh, no.” Phillip tried to keep his voice at an even tone. She couldn’t have meant it the way it sounded. He watched Donna put her drink down, but she kept the phone held to her ear with her shoulder.
“I have to get these shoes off.” The window only revealed her from her knees up, but he watched her lean over, lift her knee, and remove her right shoe. She did the same with her right shoe. Philip didn’t know what to say. He stood watching silently.
“I had a busy day at work.” Donna continued making small talk, but as she did, she reached up and unbuttoned the top button of her blouse. Her conversation only half- registered as he watched her slowly unbutton all of the buttons down her blouse. He could see just part of her white bra inside of her blouse. He heard her breathing as she pulled the blouse out of her waistband. She unbuttoned the cuffs, then held the phone in one hand while pulling off her blouse with the other, letting it fall onto the floor.
Philip silently gawked at the slender woman in her smallish white bra. He could make out the lace along the top of the cups. She looked so sexy! She looked over at him, and he could tell she was smiling. She reached behind her and appeared to be unzipping the back of her skirt. She put both hands into its waistband, and slowly lowered the skirt. Donna’s white panties, covered by her beige pantyhose, came into view. She let the skirt fall to the floor, and stood in her bra, panties, and pantyhose.
“Like the show so far?” Donna queried.
“Oh, yea!” Phillip moaned.
Donna emitted a smoky chuckle. “We’re not done yet.” She hooked her thumbs into the waistband of her panty hose, and tugged them down, one side at a time, careful not to drop the phone. When they were down to her knees, she quickly put the phone down on the bed and pulled them all the way off. As she bent over, Phillip could see a bit of cleavage hanging out of her bra. Donna quickly picked up the phone with her left hand, and held her right hand up like a model would, posing for Philip. “Do I look alright for an old lady?”
“Awesome,” Phillip replied in typical understated fashion. His cock was straining his pants as he gawked at Donna in white bra and panties. Her panties were fairly conservative cotton, but they were tight over her crotch, and dipped down a bit in front. Donna’s stomach was not as flat a Phillip would like, with a tiny handle of flesh around her hips, but overall she looked better than some teen-aged girls he knew, and her thighs looked good.
“Should I keep going?”
“Mmmm,” Donna cooed. She put the phone down again as she reached back and unhooked her bra. She picked the phone up again. “Still there?”
“Oh, yea.” Phillip stared at Donna while she shrugged her shoulders, kadıköy yabancı escort letting her bra straps fall. She pulled it off with one hand and dropped it on the bed. Donna’s naked tits were smallish white cones, sloping down just a little, but her nipples still pointed nearly straight out. Her dark brown areolas were a little larger than Phillip had anticipated, capped with erect nipples sticking out quite far.
“Very nice,” Phillip complimented.
“Thank you,” Donna replied, giggling. She put the phone down again, grabbed the elastic of her panty waistband, and pulled them down in a slow, sexy manor, while looking at Phillip. Her tits hung down and swayed as she bent over and pulled her panties off. Phillip stared at Donna’s thick triangle of brown pubic hair that covered her pussy. Donna picked up the phone again. “What do you think of me, Phillip?”
“You look terrific! Really!”
“Oh, thank you, Phillip. You know what I’d like you to do, now?”
“Would you like to come over?”
Phillip didn’t have to think long about it. “Sure.”
“OK,” said Donna, still standing naked for Phillip. Why don’t you quietly sneak over and come in the back door, it should be unlocked. Come on up, I’ll be waiting.”
“OK, I’m on my way.”
“Great. Bye,” whispered Donna, and hung up the phone.
Phillip quickly ran to the bathroom and swished some mouthwash, checked himself out in the mirror, then ran down the stairs. He quietly snuck out the door, and tiptoed through the back yards over to Donna’s back door. He tried the knob, and it was unlocked. He snuck in, and waited for his eyes to adjust to the dark. He saw a dim light coming from up the stairs, and stood at the bottom of the stairs. He saw the silhouette of Donna standing at the top. “Come on up, Phillip,” she quietly requested.
Phillip slowly ascended the stairs. Donna had retreated into the bedroom, and Phillip followed her. Donna had closed the shades, and turned off the overhead light. The room was dimly lit by only a nightlight.
“Hi,” whispered Donna, standing a foot away from Phillip.
“Hi, answered Phillip, his eyes running up and down Donna’s naked body in the dim light. She still looked good. Donna moved forward and put her hands on Phillip’s shoulders. Phillip put his hands on Donna’s bare waist, and the two embraced. Up close Phillip could see horizontal creases in her forehead, and lines around her eyes, but she still looked pretty to Phillip.
Phillip could taste the liquor on Donna’s breath as they kissed. She opened her mouth and slid her tongue out, and Phillip entwined his tongue around hers. Donna pulled Phillip so close to her that he could feel his erect cock press into her groin. Donna slid her hands up and down his back and shoulders, and Phillip mimicked her moves, feeling her naked back and shoulders. When Donna’s hands gently lowered over Phillip’s butt, Phillip put his hands over Donna’s bare ass, and gently squeezed. Donna was breathing slowly and loudly. Her hair smelled like cigarettes and perfume.
Phillip moved his right hand up her waist, then to her chest, and massaged her naked breast. He gently squeezed it, and rolled her hard nipple between his thumb and forefinger. Donna moaned as the teen kissed her and played with both of her breasts. She rubbed her crotch against his protruding erection.
Donna released her grasp of Phillip. Smiling, she reached down and grabbed the hem of his t-shirt, and pulled it up. Phillip helped her pull it over his head and drop it. Donna reached down and unsnapped and unzipped his pants. She tugged his pants and boxers together, until they fell to the ground. She stood up again, wrapped her right hand gently around kadıköy genç escort Phillip’s hard, perpendicular cock, and slowly stroked it. Phillip reached down, and slowly rubbed Donna’s pussy mound over her forest of pubic hair.
Donna slowly dropped to her knees, and gently put her mouth over Phillip’s dick head. Phillip looked down to see Donna’s mouth stretched wide over his cock. She slowly took his shaft into her mouth and sucked his engorged member. Donna put her left hand on Phillip’s bare butt, and gently massaged his balls with her right hand. Phillip put his hands on her head and emitted a low moan.
Donna sucked faster and faster. With almost no warning, Phillip felt himself cumming. He blurted a quick “I’m cumming,” to Donna, and then squirted a full load of jism into her mouth. The experienced woman downed the liquid, and slurped it all off his cock before releasing him from her mouth.
A smiling Donna led Phillip over to the bed, pulled the sheets down, and they laid down next to each other. “I’ll bet a virile young stud like you can be ready again in no time.” They continued to massage each other’s bodies. Donna stroked his sticky cock back to life, and Phillip massaged her smooth thighs before he again found her hairy pussy mound. He combed his fingers through it until his middle finger found her slippery slit. He slid the digit in, as Donna spread her legs wider for him. Having no experience at pleasing a woman, Phillip’s finger meandered around in circles for a while, then he slid it in and out as deep as he could go. He kissed down her neck and his lips found her nearest breast. He sucked on the hard nipple, flicking it with his tongue.
“Are you ready, Phillip?” Phillip presumed correctly that she meant the BIG ready.
“Yea.” He watched Donna lay flat on her back, and spread her legs wide. He knelt between her legs, briefly admiring the naked woman’s open thighs, glistening pink pussy lips, erect nipples, and smiling face. Phillip awkwardly tried to get into the right position, but revealed his inexperience.
“Don’t worry, we’ll get it. Move up a little.” Phillip crawled forward. Donna grabbed his cock, and aimed it at her pussy. He thrust forward, and inserted his cock head inside the slit. With a few more adjustments, he lowered his torso onto Donna’s and thrust his cock completely inside Donna.
This was the act that Phillip had heard about most of his life, and he was not disappointed in how it felt. Feeling his hard cock slide in and out of a woman’s warm, well- lubricated canal was everything he had hoped for.
Phillip laid on Donna, and could hear her breathing as he humped her. He felt her thighs around him as his cock slid in and out of her pussy.
Soon Phillip could hear Donna’s low moans turn into panting, and occasional whimpers. He pumped into her faster, and could feel her gyrating her torso beneath him.
Donna emitted some low grunts and dug her fingers into Phillips back. Her gyrations became more pronounced, until she was wildly shaking under the lightweight teen.
“Ooh, OhhhHH!” For a brief second Phillip thought he might be hurting her, but he kept on humping rapidly while Donna thrust up to meet him. She clamped her thighs tightly around him, and threw him from side to side. With one long wail, Donna completed her orgasm, and relaxed.
Now Phillip was close to cumming, and he continued pounding rapidly as the bed squeaked. He shot a load of jism into the grandmother’s pussy, and laid silently on top of her.
The two laid in bed next to each other, relaxing and kissing a little. Phillip felt like the most virile man in the world.
The smiling Donna sat up, sipped her drink, and lit up a cigarette. “That was wonderful. Did you enjoy it?”
“Oh yea, it was fantastic,” exclaimed Phillip.
“If we’re discreet, I hope we can do this again sometime,” said Donna.
“That would be great.”
With that Phillip got dressed, kissed Donna goodbye, snuck home, and showered before his family and Donna’s husband returned.
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