A Friend of the Family Ch. 01


Anne was just about ready to get up from the loveseat and go out to Beth's car to see what was going on when she saw Jimmy slowly walking toward her front door. She had always liked him. He was "a good kid" and very bright, more so she often lamented than her two. She remembered how the two families would play board games and whenever the game involved questions of skill or trivia the only competition was for second place...first place was always Jimmy's, even when the adults joined in. She had caught herself on many occasions wishing her offspring could be more like him...smart, well-spoken, well-read, mature, respectful, polite, and even successful, just as comfortable conversing with adults as those his own age. Not for a second had she ever had thoughts of a sexual nature about him.

As he walked slowly toward her door she thought, 'he had grown up to be a good looking young man.' He was over six feet now, well built, not terribly muscular, but well proportioned. His curly dirty blonde hair was no longer in a ponytail, the front and sides were the same length, cropped almost bowl-like. The piercing blue eyes he had inherited from his mother were cast down at the ground. His facial hair, still very sparse, was shaved close and his fair complexion was unblemished. Anne had innocently never perceived the lust in those beautiful blue eyes, the bulge in his pants or his constant ogling of her breasts, 'after all, everyone stared at them.' She finished her wine, reapplied lipstick and got up to move toward the front door, arriving just before him.

As Jimmy reached out for the doorbell Anne opened the door. "Jimmy," she almost yelled with glee, "how nice to see you again."

"Hi Anne, it's great to see you again too," speaking directly at her unbound breasts that had almost stopped swaying and were at eye level since he was one step lower than she on the porch.

She took him by the hands and almost pulled him up the step, through the door and toward her. Wrapping her arms around him and leaning in to kiss him softly on the cheek. That was how Anne greeted everyone she knew and he recalled that his mother had greeted him that way when he came home from college two days before, although his mother's breasts were almost as large as Anne's, they hadn't felt quite the same against his chest. And it was greetings like this that helped fuel his desire and hope that someday Anne would take it further.

"Come, sit down, I want to hear all about college." Jimmy walked toward the loveseat and took a seat at the opposite end from where he saw her wine glass, lipstick and cigarettes.

Still standing, Anne asked, "Would you like something to drink?"

"A beer would be nice, if you have one," he replied politely.

Anne paused for a moment. For all the years she had known him he was only old enough to drink very recently, at 19 in Canada. Remembering it was now OK, she retrieved her wine glass and disappeared into the kitchen.

Jimmy scanned the familiar living room he hadn't been in since Dave's funeral, nothing had changed. The same family photographs were in the same frames in the same places. Even the most current of his family's portrait was in the frame earlier versions had always occupied.

"Light beer OK? That's all I have," came Anne's voice from the kitchen.

"Do you have anything stronger? Like tap water," he joked.

"Very funny," Anne chuckled. "Light beer it is." He heard the bottle open and the beer slowly being poured into a glass, then wine being poured.

Anne reappeared with a glass in each hand. She handed Jimmy the beer and held her wine glass to it. "Cheers." Their glasses clinked and she sat at her end of the loveseat, again tucking one leg under her and twisting slightly to face her best friend's son. She was oblivious to the fact that her tight stretchy pants appeared to be painted on to her vulva which was clearly on display, "So tell me all about college?"

"It's harder than I thought. They said engineering was hard...I didn't realize just how hard," he answered as he too turned slightly toward her. He noticed her lewdly displayed crotch then read the words on her t-shirt which only served to reinforce his lust and hopes the words would soon to proven true.

"Oh, you're the smart one, I'm sure you're doing just fine."

"Yea," he allowed, "but it isn't easy."

"Well young man, it's about time you found something that wasn't easy."

The comment was innocent enough he thought, he had done well in school, sports and a lot of other things without much effort, but he couldn't help hearing it in terms of what he had in mind that afternoon hoping she too would be 'easy' for him.

Anne told him about how Jack and Jessica were doing at school, about their summer jobs. Jack was passing, but just. Jessica was doing better. Their summer jobs were somewhat related to their studies. Jessica was in nursing and had a summer job at the hospital near her college. Jack was studying construction technology and had a job as a carpenter's helper.

Eventually Jimmy decided that he had heard more than he wanted to about Anne's children and thought he had been polite long enough so changed the subject to something he preferred talking about. "What about you Anne? Are you keeping busy?" He already knew the answer from what his Mom had told him, but he wasn't terribly interested in hearing anymore about her kids. When their families had gotten together he hung out with Jack and Jessica more to be good-mannered than out of enjoyment of their company. Jack was one year older than him and Jessica one year younger. He and Jessica had lost their virginity together in an awkward and less than fulfilling encounter at the cottage. They had never dated, it was more experiment than relationship and he had spent little time with either of them outside of the 'family' events.

"Well...I wouldn't say busy...but active enough I guess," she said with little conviction and no excitement in her voice.

"C'mon Anne, I've talked to my Mom...you need to get out of this house...start living again."

"Thanks for your concern, but this isn't a topic of conversation for an old widow and her friend's young son." Her tone was indignant and indicated her belief that Jimmy was way out of line.

"I'm sorry...I don't want to stick my nose where it doesn't belong, but you have been a part of my whole life, you're important to me and...well...I lov...like you...a lot." 'That was close' he thought, he almost said 'I love you' to his Mom's best friend. It wasn't really love he felt for her, not romantic love anyway. It was simple, though all consuming, lust.

It wasn't as close as he thought; she heard what he said, but not what he meant. "I love you too Jimmy," she said allowing a big smile to form on her face, and then quickly added, "I love your whole family. And maybe...just maybe...there is some truth in what you say. But all my friends still have husbands and...well...it would be awkward."

"So find some new friends...ones you have more...ah...in common with. Hell, you're a great lookin' woman...you could even start dating. I'll bet you could have any man you want."

"Yea, right," she said sarcastically, "I haven't dated since college." Anne noticed that she was beginning to open up to Jimmy in a way she hadn't, even with Beth, since the funeral. It made her at ease and uncomfortable at the same time. She decided she needed a cigarette.

Jimmy watched attentively as her delicate and flawlessly manicured hand disappeared behind her then reappeared gently clasping the long slender green package of menthol Mores and her gold cigarette lighter. She set the lighter on her lap and with her right hand lightly held the package and nonchalantly taped it against the outstretched index finger of her left hand as he had watched her do so often over the years. Two of the dark brown cylinders of tobacco obediently emerged, one barely half an inch and the second slightly more than an inch. She brought the package close to her mouth.

Her full but delicate lips, sharply defined by her blood red lipstick, parted slightly as she inserted the furthest protruding cigarette between them, grasped it with her lips and pulled the package away slowly revealing the full length of the slender brown tube. It dangled precariously from her now relaxed but closed lips as she set the package down on her lap and retrieved the lighter. She brought it close to the cigarette and adroitly ignited the flame. The lengthy flickering flame pursued the tip of the cigarette as her lips pursed faintly and the dark cylinder rose from its flaccid dangle to extend erectly, straight out from her face. She allowed the flame to barely lick the tip of the slim cigarette as she drew hard on it.

She did not notice Jimmy staring at her, not even blinking. As though trying to suck a sliver of ice from a drink through a straw too small for it to pass, her cheeks hollowed and even creased from near the ends of her lips to part way up her cheek causing the end of the cigarette to burn bright. Anne always drew on her cigarette for an extraordinarily long time, when she could draw no more she daintily touched the cigarette for the first time with the first two fingers of her right hand and extracted it slowly and seductively from her closed lips' caress.

Once free of her lips, the slow removal was contrasted with the quick movement of her hand to the right, her palm turned toward the ceiling and the cigarette pointed downward toward the loveseat.

The smoke was now trapped inside her closed mouth waiting to be inhaled, but it would have to wait. Anne opened her mouth wide, displaying the mouthful of thick white smoke framed by her red lips. Jimmy was mesmerized, the action of opening her mouth caused the smoke to spin in a slow moving vortex within, a tiny plume escaped and floated weightlessly in front of her face. Abruptly, she inhaled fiercely; mouth agape and the clouds disappeared drawing even the smoke that had escaped back inside and into her waiting lungs.

Just like when she drew on her cigarette, she held the satisfying clouds inside of her for an unnatural length of time, even taking a sip from her wine before any of the billows emerged. At length, devoid of their gratifying components, the clouds began to escape unhurriedly from her nostrils. They wafted lightly out with no apparent effort on her part, as though their lighter than air quality was all that permitted their escape. Her beautifully painted face became encircled in a faint and sexy white haze.

Anne sighed deeply before drawing again on the slender cylinder. Trying to get more comfortable she pulled the leg from beneath her, pivoted on her buttocks and set both bare feet on the loveseat inches from Jimmy's thigh. The bent knees of her legs slightly obscured his view of her breasts but her smooth, muscular legs, sheathed in spandex, too were a spectacular sight as was the spandex that hugged her bare vulva so tightly that it disappeared within. He imagined her legs wrapped around his waist. Jimmy was unable to speak and neither did Anne as once more she sucked the cigarette erect.

The silence was finally broken. "This is nice. I haven't just relaxed and talked to a man since...well you know," her words escaping through the smoke.

Although ecstatic that she had referred to him as a 'man' Jimmy tried to keep his cool. "You think of me as a man? Not a boy." Try as he did, his delight at what she said was obvious in his tone of voice.

Anne was pleased that she had made him feel special, she smiled widely and said, "Much as I hate to admit it Jimmy...I may have changed your diapers...but you are definitely a man now...and a smart one at that."

"Thanks Anne, that means a lot to me, especially coming from you."

"Why 'especially coming from me?'" she asked in earnest uncertainty.

"Well, because..." he stopped and looked down.

"Because why?"

"I really shouldn't say," his voice drenched in embarrassment. His silence persisted as he contemplated revealing his long held secret and how it might affect their relationship. This wasn't how it was supposed to happen, he lamented. In his fantasies she would simply take him, without warning, without words.

"Oh, please. Don't leave me hanging like that."

Jimmy looked straight into her eyes stone faced; he could see his own reflection in her sparkling emerald eyes staring back at him.

"What Jimmy? What is it?" She was almost begging for him tell her what he wanted to keep to himself.

Finally he blurted out, "you can't tell anyone else...not even my Mom...especially not my Mom."

"Sweetie. Settle down. It's OK. It'll be our secret. I promise." She hadn't a clue what would make him act this way or what he might say.

Jimmy swallowed hard and began to speak. "I've had a crush on you for as long as I can remember Anne," his voice drenched in embarrassment.

Anne was taken aback. How could she not have known? How could she have missed something like that? Her mind flashed back to all the times they had been together. Each board game, each dinner, picnic, barbecue...he was sitting next to or across from her in every memory. She composed herself.

"Oh Jimmy, that's nothing to be ashamed of," she comforted in a motherly tone.

"I'm not ashamed," he snapped back.

"Well good...you shouldn't be. Everyone has a few crushes in their life. It will pass...don't worry."

"I'm not worried...and it isn't going to pass."

"Sure it will. You'll see," she said as she sat up and slid down the loveseat to sit next to him and comfort him, her thigh pressing firmly against his. She placed her hand that still held the cigarette comfortingly on his bare thigh, just above his knee and below the material of his shorts. She looked at him. He just stared toward her hand. She too looked toward her hand. She was shocked to see his loose fitting shorts tented up, the shape of the tip of his penis clearly visible straining against the lightweight fabric and a faint wet spot quickly forming at its tip.

At the same instant they both averted their gazes from his erotic display and their eyes met. "Jimmy, I'm not angry...in fact...I'm flattered to know a good lookin' man like you thinks I'm worth having a crush on."

"Crush may have been the wrong word Anne." He paused uncomfortably, their eyes still locked together. "You're the sexiest, most beautiful woman I've ever known." Anne had no idea how to respond so she let him continue. "The first time I...I masturbated I was thinking of you. Hell, every time I masturbate I think of you. I'm no ladies' man, but the few times I have made love to a girl I closed my eyes and imagined it was you. The day I learned what sex was I knew it was something I wanted to do with you. There...I finally said it. I guess you want me to leave now?"

Anne continued staring into Jimmy's eyes as she contemplated the implications of what he had just said. She had had a few fantasies in her life but none came close to this. She was sitting next to an attractive young man; her hand on his thigh, inches from his commanding erection, which appeared to be massive. The sexual urges that all but disappeared upon Dave's death began to rush back, building like a raging river during spring run-off. She tried to think about how wrong it would be, what Dave would think, how her best friend would feel, but those thoughts were drowned under the raging flood of erotic feelings that filled her mind.

After a very long and uncomfortable pause, acting on impulse alone with no conscious thought about what she was doing or about to do, she took Jimmy's face in both her hands and smiled coyly as she turned and contorted her body bringing her face deliberately though slowly toward his. With barely a hair's breadth between their lips she spoke, each word causing her lips to brush lightly against his. "You can keep your eyes open this time."

Before their lips were firmly together her tongue was already impatiently beyond her yearning lips and she pressed her face to his aggressively. Her tongue quickly made its way past his lips and teeth and intensely explored every surface of his hot, wet and oh so delicious mouth. She kissed him powerfully and passionately. Her mind was oblivious to everything but her overpowering desire for sexual gratification.

For his part, Jimmy's shock at what was finally happening melted away and his lust, pent up for so many years longer than hers, was unleashed. His tongue too darted around her hungry mouth. She sucked hard on his tongue drawing it into her mouth as she had done moments before with the smoke from her cigarette. Her rapacious suction drew their lips even more tightly together. She began to moan, overcome by both the strength and softness of his lips. Without letting go of his tongue she raised herself up on her right knee that was against his thigh and swung her left leg over him, straddling the seated young man and lowering herself onto his lap. She shuddered as his swollen shaft made contact with her mound and she lowered herself further. Only the thin and taught cloth of their clothes prevented the penetration they both very much anticipated. She continued crushing her lips around his, gyrating her head in small circles, opening and closing her lips repeatedly as though trying to consume him.

Ultimately, Anne broke off the kiss and sat back on his knees, glaring at him amorously. "You're a very good kisser," she said then licked her smiling lips seductively. She looked at him smiling brazenly. Without a word from either, she drew one last time on her cigarette then discarded it in the nearby ashtray, she crossed her wrists, grabbed two handfuls of her t-shirt and slowly and steamily removed the garment, tantalizingly freeing what she knew full well every man she had ever met desperately sought to see, to touch and, yes, to taste. Once her top was free of her head she tossed it on to the loveseat and shook her head triggering every hair to return to its place.

Jimmy concentrated on the sight before him, open-mouthed and eyes practically popping out of their sockets. He was so engrossed in the sight of her enormous and marvellously shaped bare breasts mere inches from his face that he could neither move, nor speak. He studied her nipples and surrounding areola. They were pink and pert like the younger girls he had been with; just as they had looked that time at the cottage. The areolas were the lightest of pink, barely darker than the smooth skin that covered the massive orbs they adorned. The nipples, now rigid from the hormones coursing through her veins, only a few shades darker pink than the areola they delicately floated upon.

Anne smiled a wide, happy, satisfied smile as she watched the young man marvel at her breasts. Finally, as she lifted each with her tiny cupped hands, she spoke, "well, are they what you expected?"

"They're the most incredible breasts I've ever seen," he gushed.

"Since when did 21 year old guys start calling them breasts? Don't you mean they're the most incredible tits you've ever seen?" She rolled her firm nipples between her fingers causing them to puff out even bigger and harder.

"Well...yea...I mean...I'm just trying to be polite."

"Forget about polite...I'm half naked...you told me you jerk off thinking of me and I'm about to fuck you...talk dirty Jimmy," she almost begged.

'She's going to fuck me,' Jimmy said to himself, 'finally!' "Your fucking tits are bodacious Anne...the two sexiest fucking things I've ever seen."

"So why don't you be a good boy and do more than just look at them...suck my big fucking tits." She leaned forward and guided her hard left nipple toward his open mouth. He accepted it willingly and encircled it repeatedly with his tongue. His hot moist tongue on her cooler nipple caused her to tremble.

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byAnne_Sexsmith© 23 comments/ 138814 views/ 43 favorites

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