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Friend of the Family

Category: Mature
20.04.2021
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Alan’s mother, Nora, had retired to a gated community to golf away her twilight years. Her comfortable home was across the street from Jim and Sally. They had been so nice to Nora when she moved in, shortly after the death of her husband, Alan’s dad. Jim was a retired banker who married late in life. He was in his late 70’s now, while Sally was in her early 50’s. He was a tall slim southern gentleman. She was a short bubbly blonde who was aging gracefully. She stayed active enough to look a few years younger than she was. She was devoted to Jim.

Alan visited his mother a couple of times a year. She usually had a list of chores for him that she had saved up since his last visit. At 45 Alan still felt a son’s obligation to work around the house for his mom. And she was always so grateful. A time or two she had asked him to go across the street to help Jim with some heavy lifting or other task that needed a young man’s strength. Alan had noticed Sally always stood by keeping an eye so that Jim didn’t overdo it, he assumed. So it was no surprise when Nora asked Alan to go across the street to help out Sally with some chore or other.

Sally greeted Alan warmly and invited him in. She had a few boxes of Christmas ornaments to be moved to an upstairs storage room. Alan moved the boxes in a few minutes. Sally insisted that he stay for some coffee. As he sat at the kitchen table and watched Sally prepare the coffee, for the first time in many years of knowing her, he began to see her as a woman, and not just his mother’s neighbor. She wore a baggy sweatsuit, but as she moved, bending down to get the mugs, stretching up to get the coffee, Alan could tell that Sally had a nice shape. He smiled to himself when he saw her large breasts sway beneath the bulk sweatshirt. She was no wasp-waisted supermodel, but she had a shapely form that seemed built for comfort. Sally had a cheery, smiling manner and easily made light chit-chat as she prepared the coffee, balancing questions about Alan’s recent separation with details of how Jim’s health had been in decline recently. In fact, she said, he was in the hospital at that time for an overnight treatment, which he required more and more these days. Alan couldn’t help but wonder whether this vital woman still had ‘needs’ and how long it must have been since Jim was able to fulfill those ‘needs’.

As Sally finally sat down with the coffee service for two, she might have been reading his mind. She started reflecting on the age gap between her husband and herself. It had been romantic for a young lady to capture the heart of a mature successful man. She had enjoyed Jim’s polite, courtly manners and the lifestyle he provided was luxurious. Jim had been a romantic, if busy man. As time went on, he became busier and had less time for Sally. When retirement came, Jim was in decline physically and still seemed to find so much to do besides being there for his wife. For her part, Sally had reconciled herself that she could live on his affection, if not physical presence, and busied herself with the house and entertaining and golf.

As she spoke, Alan couldn’t help but ‘connect the dots’. Here he was, alone and available. His social life had not exactly taken off when his wife left. And here was a woman he realized was attractive and practically begging for a man’s touch. Surely, this was all in his mind. His horniness must be overriding his common sense. This was a friend of his mother, maybe ten years older than he. And she was married to a nice old guy who Alan knew and liked. He thought that it was probably for the best to let this opportunity, if that’s what it was, pass. He smiled and nodded politely as Sally talked.

When the coffee was gone, Alan excused himself and stood to leave. As Sally walked him to the door, she suddenly remembered one more thing she needed Alan to do for her upstairs. He followed her undulating rear up the stairs. She led him into the bedroom and Alan felt like he was going to have to say something about respecting Jim too much to do anything. Before he could, Sally showed him a pile of shoeboxes and asked him to move them to a high shelf in her closet. Alan obliged. Sally disappeared for a minute and then reappeared, now wrapped in a sheer kimono-style wrap. She lay on the bed and looked up at Alan.

As he turned from the putting the last box in the closet he saw Sally reclined on the bed against large pillows. Her legs were exposed and looked soft, creamy smooth and inviting. Sally big breasts were visible through the sheer fabric. Alan could see large dark circles capping each mound. Sally patted the space next to her. Alan froze. The moment seemed to last forever. Sally ran a finger down her front, parting the wrap, revealing much of her breasts and a neatly trimmed pubic mound. Alan was still frozen. Sally wondered if she had made a fool of herself. Not knowing what Alan’s response would be, she decided that she needed to do something. She began to finger herself. Her eyes were locked on the stunned Alan. Alan’s eyes were focused on her two fingers rubbing small circles at the base of the little patch of downy brown hair. His eyes widened. Sally needed to cum and at this point she had stopped caring what would follow her release. She continued to consume Alan with her eyes and pushed a finger inside her pussy.

Alan had never seen a woman masturbate. His ex had never been too sexual and what sexlife they used to have was always quick, quiet and in the dark. He was just paralyzed with indecision. She had gone past a point of no return. Should he? He couldn’t think. It was animal instinct that controlled him. He found himself rubbing the hard lump in his jeans openly. When he saw Sally’s smile at this, he unzipped his fly and his cock sprang out. He stroked it slowly.

Finally Sally broke the silence.

“Alan, I know this feels strange. But Jim hasn’t been able to make love to me in years. He used to ask me to leave him to find a younger man. He told me to find someone but not to tell him. He knows I have needs. He even suggested I seduce you, but I guess I didn’t succeed at that. Alan, it’s been so long since I felt what I need. I need a man’s touch; I need to service a man’s needs. Please take me and use me, make love to me, fuck me, hurt me, anything you want, but please come here.”

Alan could feel her need add to his own. He was drawn to her side. Standing beside the bed, his big cock straining, Alan was in a trance. Sally stared at his hardon as if she had never seen one.

“Ooo, so hard.” He felt her breath on his stiffness. Her hand encircled it softly, slowly, as in a dream. She stroked it gently at first, and then, as the heat inside her rose, more purposefully. Sally looked up at Alan with a loving smile. She undid his jeans and pushed them to the floor. Returning to his cock she stroked it with both hands. She shivered each time her hand made contact with his warm stiff meat. She pulled his boxer shorts down and he stepped out of them. Alan slipped off his shirt and stood before his mother’s friend naked and hard. Sally’s wrap had all but slipped off as she undressed Alan.

“Get this off,” Alan heard himself say. Sally immediately complied, smiling up at him. She raised herself up pushing forward her big boobs and sucking in her stomach. She looked so much better naked than she did in that sweatsuit or any of her other clothes. Alan cupped each big breast in turn, weighing and squeezing each one. Her nearly white skin contrasted the deep dark ruby red of her aureole and small, stiff nipples.

Sally returned to her worship of his cock. She caressed its length and stroked it. It was as if she had never seen a cock before. They both would have been happy to let her stroke him to completion, but years of neglect and need were driving them now. She wanted to ask if she could suck it and he was about to tell her to suck it, when she just moved her lips to the head and slowly, gently engulfed it. Her mouth was warm and wet. Her tongue swirled around the sensitive knob. This was something she hadn’t done in many years. Jim was not a fan of oral sex. But in her younger days Sally had kept her virginity by becoming a blow job specialist. And she seemed to feel inside herself a sympathetic pleasure to the one she was giving Alan. She knew she could cum just from this. Alan knew he could too, but he was so turned on and so hard that his cock felt almost numb. He could feel all Sally was doing, but he didn’t feel that rush to climax.

“Deep,” he heard himself say. Sally shivered again. She took her mouth from his manhood and looked up at the dazed Alan. She smiled so sweetly, as if her dearest wish had finally been granted. A devilish tinkle appeared in her eyes. She took his cock into her mouth and slowly slid her lips down, down, down to the base. The sensations flooded over her. It had been so long since her throat had felt full, since she had to suppress her gag reflex. She could feel the hardness throbbing in her tight throat. Her mouth watered and she began to suck and pump slowly up and down on him. Alan had never had a woman so much in heat before. Like most men he had always had to beg and plead for the quick wham-bam once a week. And here was a sexy mature woman who had long-neglected skills and a long suppressed desire.

Alan gazed down at Sally as she slowly, masterfully worked her mouth and throat up and down his shaft, twisting and pausing to let her tongue work the length and even to push out and tickle his heavy balls. She would pull off the hardon and look at it in wonder, thick strand of clear saliva dripping from it and her lips. Her chin was covered by this sexy drool. Again she plunged all the way down on it. Alan was suddenly possessed to firmly grab Sally’s head and hold it still, with his cock still buried as deep as it could be down her throat. He then pumped his hips in a series of rapid thrusts. Each thrust elicited a gurgling gasp from Sally. Her eyes watered but she was in ecstacy. She realized a warm feeling was building deep inside her. As Alan released his grip on her head and Sally began pumping it in long slow strokes, partially gagging herself with each penetration. A sudden wave of pleasure consumed her and shook her bodily. She forced her mouth all the way down on him and screamed a muffled cry around his cock as she came harder than she had in years. Alan feared she would hurt herself and pulled out part ways.

Sally was still moaning and shaking as Alan nudged her over on the bed to make room for him. He hugged her from behind, his hands finding their way to Sally’s big tits. He squeezed them gently and then, hearing her sigh of approval, began to treat them more roughly. Finally, he was mauling her large soft mounds. As he did he rubbed his hardon along her pussy crease from behind. Her hand guided him home. He could feel the volcanic warmth and wetness. She was tight but yielding. He held her close that way for a long time. She felt his strong arms enwrapping her and his big hands kneading her mams. And her pussy just undulated and rippled and massaged his length. The smallest movements that each of them made sent waves of pleasure through the other. Slowly, he began to stroke in and out, rocking and driving Sally against her large pillow. She felt her passion rise again and turned her face into the pillow to scream out her joy. Her orgasm drenched Alan’s cock. He felt his nuts tightening. He had a load that would not wait much longer.

He lifted Sally and himself up to where she was on her hands and knees with him kneeling behind her, without withdrawing entirely from her tight snatch. She couldn’t remember the last time she had been taken from behind. Like a dog, she thought. Like a bitch in heat. She barked and moaned and shrieked like a banshee. Sally didn’t just kneel there and let Alan pump her. She fucked back at him as ferociously as he thrust in. Her hips twisted and flexed. Her pussy gripped and released him. Alan saw Sally’s big round jugs swaying as they hung down from her chest. He cupped them roughly. He pinched her big nips and twisted them. She was a fucktoy to him now. Any thought of who Sally was to his mother or of Jim in the hospital was a million miles away. This was two animals instinctively fucking for pleasure. Alan drove in balls deep. Sally arched her back and screamed his name. His hands grabbed her hips and he pumped her slapping against her fine round ass with each thrust. Sally’s breathing came in gasps and grunts. Alan felt his climax approaching. The sensations were just mind-blowing. Sally’s firm ass slapping noisily against Alan’s thighs, the weighty fullness of her big milkbags sloshing in his hands, the wet velvet vice of her cunt gripping, squeezing and pumping him, the smell of her juices filled the air. He was almost there.

Instinctively, Sally reached down underneath, between her legs and cupped Alan’s cum-heavy balls. She felt their heft and carefully rolled each nut in her fingers. Alan growled his enjoyment. Sally stretched her hand back further and a wet finger found his anus. Alan had passed the point of no return. A couple of long hard deep glory strokes and he could feel his balls and cock erupting. Sally lunged forward off of the stiffness impaling her, whirled around started jacking his cock with both hands. She looked up at him with a Mona Lisa smile. Alan was in another world. She knew just what to do.

“Blow your big cumload on me, baby. Shoot your wad all over me. Make me your cumwhore.” With that she deepthroated him with a gurgle and as she pulled off, he erupted. Sally stroked his spurting cock with both hands. She smiled as huge blasts of thick white spunk blasted onto her face. She opened her mouth and extended her tongue. She wanted to eat his cum. She wanted him to see her eating it. She wanted him to mark her with his mess. She reached down with one hand to squeeze his balls as if to greedily wring the last drop of jism from them. She continued to pump his cock until his moans and bodily shaking subsided. Alan collapsed on the bed next to her. Sally looked down at him as she used her index finger to scoop up and push the globs of cum clinging to her face, to her mouth to eat them. Some had dripped down onto her sizable boobs. Sally made sure Alan was watching as she sucked his cum from one of her stiff nipples. Cum still glistened from her face and chest as Sally kissed Alan deeply. He tasted his salty cum on her lips. Sally lovingly kissed her way down to his still large, but softening cock. She gently licked and sucked it clean.

She lay in his arms for a long time, telling him how incredible she felt and how long she had dreamed of what they had just done. She was concerned Alan would think less of her. She needn’t have worried. Then she confessed that she had other dreams that she wanted Alan to help her fulfill. There were dirty, nasty, things she longed to try, things she had almost given up hope of ever feeling. Alan told her he would be there for her, whatever her desire.

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