Her Best Friend's Son

Her Best Friends' Son

Mid-forties woman with young man.

Author's Note:

Breaking out of a writer's block with this story. I hope you enjoy it.

MP

~~~

Allison stood back while her best friends, Caroline and Tom, said goodbye to the last of the adult party guests. The occasion was their son Bill's 18th birthday, and he'd left with the younger guests an hour earlier to go swimming at Stone Lake.

After the goodbyes Allison joined her friends and said, "It was a wonderful party, a perfect gathering of two generations."

Caroline nodded, and observed, "God, those kids all grew up fast."

Tom smiled affectionately at his wife and spoke to Allison. "They grew up a little too quickly for Care." Using Caroline's nickname. "She's already dreading Bill's departure for college in two months."

Caroline looked at her husband and spoke more sharply than she intended. "And you're not?"

He put his arm around his wife to mollify her and spoke softly. "Of course I am sweetie. But I'm also thinking about all the things that await him. Adventures and challenges with young men and women that are in the same shoes as him.

Allison asked the couple, "Speaking of young women, still no broken hearts he'll be leaving behind?" When they shook their heads, she added. "That surprises me. I've never met a nicer young man."

"And handsome," Caroline said of her son, "like a younger Tom here." She gave her husband a quick kiss and added, "Who I fell for like a ton of bricks."

Allison enjoyed their comfortable affection in her presence, without feeling jealous because of her own divorced status. She said, "He's doing a wonderful job around my place this summer, painting and fixing things up. You've taught him all the skills he'll need as a young husband Tom."

"Maybe not all the skills he'll need." Tom said. He shared a look with his wife that indicated there was something more behind his statement.

Caroline visibly considered how much to share with their close friend, then blurted out, "We think he's had some difficulties with girls his age." She looked to her husband to explain.

He said, "I tried to feel him out on the subject, see if there were things he needed to discuss with me or advice I could give, but he clammed up on me." He searched for the right words, then continued. "I think there are serious

confidence

concerns, but don't know why."

When Tom fell silent, Caroline continued for him. "Tom thinks it's similar to a period he went through in his teens."

When Allison asked Tom why he didn't simply tell Bill how he'd gotten through those times, he looked at his wife questioningly. They seemed to come to a silent agreement, then Tom faced Allison. "I lucked out. One of our neighbors was a woman my parents age who took it upon herself to show me what a young man needs to know about women. I don't know how she knew I was having a crisis of sexual confidence, but somehow she did."

They saw confusion mask Allison's features so Caroline said, "She became Tom's lover and showed him how to please her."

Tom nodded and said, "A real woman." He seemed to fill with the memory. "A woman," he repeated, "so different from a girl. With a woman's hips and breasts and ass and private treasures who'd made love to men and showed me how to love her like a man. So after that summer, I left for college as a man."

Caroline added, "A confident man who knew what he was doing when I met him a year later." She looked at her husband and visibly warmed with the memory. "I didn't have a chance. I didn't want a chance. All I wanted was to have him show me more."

Allison blinked. She'd not expected this conversation.

Caroline continued, "Tom told me about her and then I actually met her two years later, at our wedding when a beautiful woman I didn't know approached me as I was standing alone. She introduced herself as a neighbor of Tom's parents and said that he did a lot of work for her over his last summer before college... and just like that, I knew! I was talking to the woman who taught Tom how to be the lover he is." She beamed at her husband, then looked at Allison and said, "I hugged her and thanked her and she knew what I was thanking her for. She hugged me back, smiled and said, "The pleasure was truly mine, my dear. Young Tom only needed a little encouragement."

Tom was watching Allison's reaction and said, "That sort of inter-generational sex-ed is condemned in our society even when the young man is over eighteen, but I think it's perhaps the most effective way to help a boy become a man in that crucial sense."

"And it's so important to the fulfillment he and his partner experience through their lives." Caroline added.

Allison looked at her, then Tom, and knew why they were telling her about the older woman in Tom's past. She was opening her mouth to say she couldn't be that woman for their son, but stopped herself. Instead, she said, "I'm sure he'll work it all out, but in the meantime I'm grateful to have his help fixing up the house."

Caroline said, "He says it's the best summer job he's ever had." She smiled mischievously, "But maybe that's because he gets to see you sunning by the pool sometimes."

"I doubt that's it." Allison replied matter-of-factly. "I'm usually at the firm and have only worn my old one-piece by the pool when he's around."

Caroline got an impish smile and said "If you wore the skimpy bikini you bought for your Caribbean vacation he probably wouldn't get

any

work done!"

"You're crazy Care." Allison retorted. "I'm 26 years older than your son, older than you, his mom. And he's obviously something of a young hunk."

"Who looks at you like you're a goddess." Tom said. "I know that look from when it was me at his age. He's all eyes for you as a woman."

"Well, I'm sure everything will work out for him without intervention from me." Allison's tone said the discussion was over, but the debate in her mind had just begun.

I know young Bill is really enamored with me. I'm not blind. And I do wonder what it would be like to be with someone so young... But if anything ever happened, I can't imagine talking about it.

~~~

In bed that night, Caroline snuggled against her husband and said, "What do you think?"

"We'll see. The idea is certainly planted, and she knows how we feel." He thought silently, then added, "Now we have to leave it alone?" Looking at his wife with his eyebrows raised in question.

She debated arguing they should push harder, then reluctantly agreed. "Okay..."

~~~

On a whim the following Monday Allison decided to take the afternoon off because it was such a beautiful early summer day. She came home to find Bill cleaning up his paint supplies. "Are you done for today Bill?"

"Oh no. Just done with trim on the back. This afternoon I'm going to work on your back privacy fence. Are you home for the afternoon?"

"Sure am," Allison replied, "I want to enjoy the pool on a day this perfect. We don't get many like this."

"Will it disturb you if I work on the fence?" He asked. "I could find something else to do."

"Not at all. Do what you planned. Would you like some cold chicken and fruit before you start?"

"That'd be great!" He responded enthusiastically.

"I'm going to get out of these office clothes and into something comfortable first, then I'll bring it out to the patio."

"That'll give me time to finish cleaning this up." He answered.

During the brief exchange Allison saw Bill in a new light. She supposed it was due to the conversation she had with his parents, but for whatever reason she wasn't just seeing him as the capable teen she hired to fix up her house. Instead, she saw a young version of his dad. She saw a virility she'd not really noticed before. She always thought he was handsome, but this was something more. Caroline wasn't shy about privately telling Allison what a wonderful lover Bill's father was. She'd even said with a salacious smile that he 'measured up' where it counted. Then, when Allison was leaving on the evening of the party, Caroline had pointedly told her that physically, Bill truly is a younger version of his dad.

When she entered the master bedroom Allison started to close the outside curtains, then decided not to.

It's too beautiful to shut the day out

. Instead, she opened the sliding doors and saw Bill briefly glance up from where he was cleaning his brushes. As she moved deeper into her bedroom, Allison realized she liked knowing she wasn't closed off from the young man, and paused to study him before going into the walk-in closet to change. She was again struck by his youthful manliness.

He's really not a boy anymore

. Watching him, she imagined young Tom before he met Caroline.

In the walk-in she decided to dress for sunning by the pool and wear a sundress cover-up for lunch with Bill.

An uncharacteristically youthful look for an attorney in her mid-40's

, she thought,

but I'm feeling strangely young

. As she released the clasp of her restrictive work-bra and rubbed her breasts Allison realized she could still see Bill reflected in the full-length bedroom mirror. She watched him work and imagined his hands on her. She closed her eyes and imagined it was him squeezing and weighing her tits. She imagined it was his thumbs flicking her nipples stiff, his strong fingers rolling and pinching the erect nubs, and even imagined feeling his hard cock pressing against her bum as he fondled her tits from behind.

When her eyes finally opened again...they met his.

He was in the back yard, staring open-mouth directly at her sexy image in the mirror.

Their eyes locked for several heartbeats, then they simultaneously turned away.

Outside, Bill softly muttered, "Holy fuck..."

In the closet Allison breathed, "Oh..."

Their physical reactions were more profound. Her body tingled and her core melted.

His young cock challenged the confinement of his cargo shorts.

Bill's mind raced as he fought to concentrate on his cleanup task. He knew he had to act like nothing happened, but in the next instant all he could think about was the sight of Allison squeezing and fondling her incredible tits.

Holy... fucking... shit

. He imagined them in his hands, then batted the image away and told himself to pretend nothing happened... only to have the image flood his mind seconds later.

Allison also knew she'd pretend it hadn't happened even as she decided to wear her skimpy bikini under the sundress. She wanted to take full advantage of the sunning opportunity. The suit had garnered many admiring looks on her Caribbean vacay but nothing like Bill's lustfully raw ogling moments earlier. Without consciously thinking about it, Allison knew she wanted him to look at her that way again. It made her feel sexier than she had since... well, ever?

A few minutes later, Allison was in the kitchen wearing the bikini without the sundress cover-up when she called to Bill, asking him to fetch the iced tea and glasses to the patio. She faced away from the door when he entered, but heard his sharp intake of breath. That gave her the courage to turn and face him and when she did, his eyes grew large. The bikini was skimpier than she ever dared wear in public outside of the tropics, where women commonly wore such suits. Her nipples were covered but her breasts were mostly exposed and only a small triangle of fabric covered her sex. It was a younger woman's suit that left little to the imagination.

The young man was like a deer in headlights and his reaction hardened her nipples.

My body's presenting itself to him

. The wetness Allison felt between her legs surprised her.

I didn't mean to move so fast, but his young hunger is

...

She smiled as if she wasn't putting on a show for him and pointed to the pitcher and glasses. "Thanks Bill. The iced tea is right over there."

The young man strained to tear his gaze from her. "Sh...sure Mrs. Sanders."

"Bill..." she said with faux annoyance, "call me Allison. Please?" With a big smile. "Otherwise I'll have to call you Mr. O'Connor."

"Ye... Yes ma'am." He stammered.

She challenged him with a smile and said, "Mr. O'Connor?"

He broke into a smile when he realized how he'd addressed her and relented, saying, "I've got the iced tea Allison." Then he took the tea outside and sat where he'd have a good view of her coming out to join him. When she emerged carrying a tray with the food he was disappointed to see she'd donned the sundress cover-up, but there was still

a lot

of movement under the light fabric and now he knew how she looked inside the cover.

Allison savored his reaction to her body and wore a radiant smile.

I wonder if he'd even be able to eat if I hadn't pulled the sundress over the suit.

Before sitting down across from him she asked, "Do we need anything else?"

He answered without thinking, "No Ma'am," then quickly corrected himself as they both struggled to keep from giggling. "No Allison. We're all set."

Their shared smiles lightened the mood dramatically and Allison encouraged him to eat by digging in herself and saying, "I never order fried chicken in a restaurant because the only good way to eat it is by hand." With that said, she tore apart a wing and started pulling the meat from the bones with her teeth and Bill quickly followed suit.

"This is great chicken." He proclaimed after quickly finishing his second piece.

She nodded and said, "And fruit, even if it does make me a mess."

When he looked at her to see if she'd gotten grease on her face he didn't see a trace of any. He didn't see so much as a hair out of place. Everything paused for him in that instant and he stared as she seductively extended her tongue for a grape she lifted to her mouth.

She has to be the most beautiful woman in the world... And she's eating with her hands in a sexy bikini.... With me.

She realized he'd stopped eating and was looking at her, and then startled him when she said, "What Bill?"

"I..." He searched for the right words. "I..."

"Is something wrong?" She pressed.

"No. Nothing. You're just so... so..." He paused and thought,

God damn

,

I have to say something now

. "Well... you're so beautiful, Allison." He not only used her name this time, he did so comfortably and it felt different coming out of his mouth. Like her name belonged in his voice.

Allison's mouth fell open just for a moment, then she closed it and looked unguardedly at Bill and as she looked she blushed like a schoolgirl talking to her heart throb. She hadn't expected that level of sincerity from him, and was even more surprised by her reaction. Her mind raced as she took in his features.

I thought I was playing at being a seductress. I didn't think I'd be so affected by him... and damn... he's grown into a handsome young man

.

As she looked at him, Bill studied her and saw how his words had affected her as a woman. The knowledge filled him with a new potency. He felt he belonged here, with this beautiful sexy woman.

As Bill studied Allison, she looked down. When she looked up again, there'd been a subtle change in her. Her eyes met his and she spoke softly. "Thank you." She found her equilibrium again and didn't shy from the compliment. "I'm not used to a compliment like that, especially from a handsome young man like you."

"You are," he said more firmly, "incredibly beautiful."

"Thank you." After a moment she added, "The way you look at me... makes me feel beautiful."

Neither of them moved to take another bite.

Their hunger for food was gone. Their hunger for each other took its place, silently communicated as a man and woman can when all pretense is finally abandoned. Words could add nothing.

Allison admitted to herself that she knew where she wanted this to go before she left the bedroom, and boldly decided to take it there now. Bill could choose to join her - or not. She stood up, walked to the door and paused to face him with a look that said everything.

He rose and followed, mesmerized by the sway of her hips in the sundress as she led him through the house to her bedroom. There, she turned and faced him.

He was lost.

Should I embrace her? Can I?

His cock fought the confinement of his shorts and was so hard that it hurt.

Holy fuck... Is she waiting for me to take charge?

Before going into her walk-in closet, Allison spoke softly, "Wait here... please?"

Bill nodded.

If anything, he was more lost. He could hear the sound of fabric against skin.

Is she stripping? Oh fuck

. His heart was pounding.

Should I be stripping? Is this really happening?

When Allison emerged from the closet and walked towards Bill he stopped breathing. She wore the sheerest of negligees, loosely closed in front. From the motion of her tits and the dance of stiff nipples against the silk, he knew she was naked underneath. The shape of her full tits was revealed by light coming through the gossamer fabric.

They looked at each other without moving or speaking for several heartbeats, then she finally spoke in a reluctant whisper. "I'm older than your mother..." She looked down.

Her vulnerability moved him to boldly step closer and extend a hand to the side of her face. She looked up, into eyes that met hers as he said, "I don't care." The hand slid past her ear to cup the back of her head as he leaned forward and softly touched his lips to hers.

She struggled to quiet a shiver.

God... I feel like I'm in a different world. Who is he...?

He rested his forehead against hers, then she tilted her face to make it easier for them to kiss. Allison's mouth opened as his approached, and when his tongue slid against hers they pushed into a twist. Her woman's flavor in his mouth engorged his cock. The taste of his virility laid bare her sexual need.

He's tasting me the same way...

She felt his hunger for her,

for how I taste, what I feel like

. She knew he was savoring her and it opened her to him. She wanted him to know all of her.

When their kiss finally paused his hands were resting on her shoulders. Did he whisper, or was it only the silent message of his touch?

I don't know what to do next

...

Allison covered his hands with hers, then moved them lower, slowly opening her gown with them until his palms were flat against the skin between her breasts. Then she dropped her hands and lifted her gaze until they were looking at each other.

Then he knew what to do next.

Bill's hands slowly moved apart... until they covered her. Their breathing deepened. He cupped her softness, then held her. Allison felt undone in the size of his hands. Then he squeezed and her head rolled back. They both groaned aloud. He savored the give of her softest flesh to his exploring strength. He squeezed harder than an experienced man would, hard enough to bruise in his youthful wonder. The uncontrolled nature of his lust excited her. She guided his fingers to roll and tug her nipples, then explored the prominent bulge in his cargo shorts. Allison marveled at the dimension of the bulge. She stroked Bill's length and measured the unmistakable shape of his big head. The heat she felt through the fabric thrilled her.

I make him this hot...

Meanwhile, his tugging made her nipples ache to be suckled as nature intended. Bill bent over and took her left nipple and entire areola into his mouth, then suckled with a fervor only found in a man who hasn't had a tit in his mouth since infancy. Allison felt the pull of his suck in her cunt. She pushed more tit into his mouth as her hands squeezed him in his shorts and when he switched tits she started opening his waistband. When she had it opened, his cock kept his shorts from falling. She pushed them lower until they fell to his ankles and his youthful cock sprang free in a timeless display of potency and demand. When Allison's hand closed on his bony tumescence his girth made her gasp. She looked down to confirm the measurement of her hand and Bill looked with her, wanting to see the cock that only he'd held, in her feminine hand.