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A Family Friend The First Lesson

A Family Friend The First Lesson

by daddynyc873
20 min read
4.65 (11000 views)
adultfiction
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The first warm day of the year was here, and it fell on a Saturday. Lena couldn't wait to get her string bikini on and lay at the pool, the lovely pool SHE had paid for, so she asked her daughter Jackie if she wanted to host a pool day. It was her way to feel feminine again after a long week at work. And maybe bond with her daughter before she went away to college. At least she hoped. Ever since the divorce (or maybe just the normal teenage process), she had been spending more time with her "clique", a few chatty girls, and a couple of boy friends. She always had one eye on all of them. Especially the boys. After some teenage rumbling about her friends being "skanks", she said she would call Billy.

"Stop that, he hates when you call him that."

"What, it's short for William, right?"

Lena rolled her eyes. She kind of felt sorry for Bi...William, mainly because her daughter had mercilessly put him in the "friend zone". But he was a sweet, quiet boy, tall but shy. He had a bit of a stutter that made him a source of teasing with the meaner girls of the group. Lena hated it. She went through a period of self consciousness. Albeit for different, female reasons.

His home life was...not easy. His mom was never going to win "mother of the year" awards, thats for sure. There were constant rumors about her being a "loose woman", out at seedy bars and being in the company of very married men at all times of the night. Lena even questioned if she fed the tall, lanky boy sometimes. She had tried to reach out to Rebecca to make friends. But between the obviously drunken phone call they had, and Lena seeing her out with her not so secret lover, she decided against it. At least Bi...WILLIAM, can come over here and feel safe. He wasnt like the other boys who stalked around her, obviously wanting one thing. She saw the future assholes to women they were going to become. Not William. He was always respectful from the first time she met him the year before high school. He was not as tall; his growth spurt didnt hit until junior year. He always called her Ms. Keefe, her married name (her maiden name was Santos). She didnt mind, not from him. It always came out genuine, almost as if William was happy to see her. A soft smile always greeted her. She would go out of her way to make him a special sandwich whenever Lena heard he was coming over. She loved being the "cool mom" that way.

She also thought he had a crush on Jackie. Who wouldnt-she was built like her at that age. Five foot two, nice full C cups, long black hair that went down her back. Her skin was a light tan, which her mother's Spanish heritage provided. Big, Jasmine like eyes, that matched Lenas. Full lips, also provided by her mother, with a radiant smile. Lena had filled her hips out with childbirth, but pilates and yoga kept her figure to a point that her daughter was even a bit jealous. Red lipstick, always worn- never NOT wear lipstick, Lenas mother told her-accentuated the fullness of the curvy puffs of her lips. Her rear end would make J-Lo envious. Her bikini could barely contain the fuller D cups that motherhood had also provided, so some women half her age (and all the men) could not help but stare and admire her-or be jealous. Shit, even Jackie's asshole boyfriend Colin was caught staring too long at her one time.

Either way, she was having a pool day. And not even a moody teenager was going to stop her.

She pulled out her new purchase-a slightly skimpy, even for her, white string ensemble she got on clearance at Nordstrom in the fall. Trying it on, she gave it the once over. The supple, mature curves her body still had were accentuated perfectly. Her breasts were still perky, and the top gave her a very impressive cleavage. She looked better than some women 10 years younger than her. "Yep, I'm still hot..."she whispered into the mirror. "Not bad for a late 30s girl." She giggled at her own joke at her expense; she was 42. At least she could tell herself that, since nobody else was available. She didnt mind that she hadn't had even a prospect since the divorce almost 5 years ago. Not that men hadn't tried.

Oh, they tried.

After her breakup with Chad ("Never date a Chad" was her mom advice now), she had been hit on consistently at work. Including her boss, that one late night in his office for "paperwork" that he pulled his stubby, flaccid cock out and offered her "benefits". One call to HR alleviated that issue:that office was now hers. Now nobody even could look her in the eyes and feel safe. She liked it that way. And Gustavo (her vibrator) wasnt going to cheat on her with your former babysitter.

The noon sun hit the expansive yard perfectly. The pool was her reward to herself for a huge bonus from work. It was a nice place to entertain, if Lena had actual friends in Jackie's "clique" mom group. But most of them were either too chatty, too PTA, or just strictly insanely jealous. Many a time at school functions she noticed the dads ogling her, even hitting on her within earshot of their wives. "Fuck em. I dont need that negativity. Ill just enjoy my new pool alone." She'd rather have a quiet afternoon sunbathing than gossiping about god knows what. Probably Rebecca. Fucking Rebecca.

Lena had just lathered sunscreen when Jackie called from inside the house.

"MOM, BILLYS HERE!"

"HELLO WILLIAM!" Lena called out, a bit sternly to her daughter. Eyeroll city. She had heard her call him Billy so many times it had started to burrow in her brain now. "Hi Ms. Keefe!" He shouted from the kitchen, out of sightline. She could hear Jackie babbling about something. Then a few seconds of quiet.

"He doesn't have a bathing suit." She was now standing over her beach chair.

"He doesn't?"

"Nope."

She sighed. Fucking Rebecca.

"Maybe he can borrow one of dad's?" Jackie mused.

Lena looked at her over her Ray Bans. "Your dad was 5'6". He's way taller. What makes you think it'll fit?"

Jackie shrugged. "Better than nothing."

Lena relented with a wave and an "okay." She was glad his shit was being put to good use anyway. He was lucky it wasnt burned in effigy.

Jackie went into the garage to dig through some old boxes.A few minutes passed and Jackie came outside. Lena asked without opening her eyes.

"Did you find any?"

"Yeah, they might be a little small on him." Ya think?

Lena hadn't kept track of time, slightly dozing away, when Jackie spoke.

"Mom, can you grab me a soda?"

"Can't you get it?"

"But I JUST put lotion ooonnnn..."

Lena looked at her annoyingly and scoffed. "Spoiled little brat..." she muttered to herself, and got up. I HOPE SHES LIKE THIS WITH CHAD NEXT WEEKEND. HE CAN WAIT ON HER HAND AND FOOT FOR ONCE. She needed some water anyway.

Brushing back her hair, she sauntered to the French doors into the kitchen. As she did, she noticed William wasn't there. Not like him to be away from Jackie for so long, she mused.

As Lena entered the kitchen, a Katy Perry song was playing on the radio, giving her some energy to shimmy to the music. Swaying her hips, she momentarily forgot about the boy, just turned 18, lingering about the house.

She poured her water on the floating island in the center, still swaying and shimmying her breasts.

William had just come from upstairs. He seemed to be very careful about his movements, which seemed strange to Lena. His hands were low on his hips, almost like he was about to start jogging. She paused her dancing and looked up to greet him, taking a sip.

"Hello Bi...William!" She said, disappointed she just broke her own rule. The boy was an unusual shade of pink. He didn't notice the bikini clad woman in his path at first.

"H-h-hi, Ms. Keefe..." he stopped suddenly, eyes widening and gulping. William had never seen her in a bikini, at most jeans and a baggy t shirt. His eyes darted up and down her form, resting at her still slightly swaying cleavage. Lips parted slightly in amazement.

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Lena realized why he'd been so careful: he was tall and skinny, so skinny that the trunks were barely hanging onto his waist. But the cut of the suit made it look like he was wearing daisy duke's. Lena could only hold back an astonished chuckle.

That's when she noticed something...else. He face had turned beet red, and was holding his hands in front of him. Curious she looked down, and gazed on a shocking, yet glorious scene.

He was rock hard. And holy SHIT, it was big. Not big...HUGE. WHAT. THE. FUCK.

Her hand went to her mouth, but all she could get out was "wow". And "wow" didn't even come close to how her body reacted to it. She had only thought cocks like that existed in porn and fairy tales men told each other, and she was sure porn made it look that way with camera angles. But this...BEAST...it was oh so real.

"Wow, that thing is huge..." she whispered, mouth hung open in amazement.

Like a cloud being lifted, Lena suddenly remembered how long it had been since she was this close to a man's member, and even then it had been unimpressive at best. She shivered with a new found energy, a deep energy, she hadn't had in years.

Was she...horny all of a sudden?

The Boys face contorted into an embarrassed, pained expression and tears started to come.

"Oh...oh no...i-i-im ssss-sorry...". He was shaking now.

His voice snapped her out of her hypnotized gaze."No...William...its-its ok...its natural..." this poor boy hadn't even seen a slip of real breast yet, she imagined. She reached for his hand, stopping just short of grabbing the behemoth by accident. She struggled to get her composure back. And not think of...him...and what she suddenly craved.

"It's OK to feel like that sometimes. Everybody does. You're just learning about your body. Nothing to be ashamed at." Lena was actually feeling complimented about the fact she made the boy that horny. Dare she said it...it kind of excited her.

"Y-y-y-you sure? I didn't of-f-f-fend you?" He looked up sheepishly, but his embarrassment was starting to melt away.

"Offend? Jeez it was a compliment!" Lena chuckled. She was used to men ogling her, but his shy admittance was appreciated. "I'm glad you think I'm attractive!" She twirled her hair a little, a smile came over her face. "Jesus, am I flirting with him?" She thought.

"Oh wow...youre...sssso..ssssstunning.."he struggled to find the words, as he blushed brightly. He couldn't tell her the main reason she hung out with Jackie was actually...her. He always liked her- hell, he paid more attention to him than his mother-but an admiration turned into a serious teenage crush last year when puberty hit and he started growing. Everywhere. His mom cruelly joked the only good thing that his father gave him was swinging between his legs. Not exactly a supportive statement to a teenager who already had lack of confidence. She called him "Big ol Billy", the main reason he preferred William.

Lena couldn't help but blush a little. She had been called "hot" or "sexy" countless times. But STUNNING? Not even her ex or any of the few boyfriends she had before that called her stunning. It was...mature. Adult. Attractive even. Things that most men even her age still lacked. A light warmth came to her face.

"Thank you. That makes me feel...really good." Lena's warm smile calmed the shaking ball of teenage testosterone. She could almost smell the pheromones coming off of him...

She had a moment of brazen courage. She took a few slow steps forward, embracing her womanly energy. Her insides were trembling a little, a light tingle over her body. Some switch in her body had gone off. She remembered it was good to be desired sometimes...to tempt and excite the opposite sex. And she wanted more.

Something else was stirring, inside her...when she was in a playful or adventurous mood, she would call her vagina "LeLe". It was almost an alter ago if hers. LeLe had been both a help and a hindrance in her romantic life. After the divorce, LeLe went dormant, afraid that she would never be satisfied and her passion would wither away, only to be shared with with Gustavo.

Well, LeLe was awake.

And she was WANTING.

She spoke to her in what felt like a sassy yell, a personality all to herself. I'M AWAKE BITCH! LETS GOOO!

"It's ok to be attracted to girls. As long as it's respectful."

"Oh...yyyes Ms Keefe. I wouldn't do anything...w-w-w-weird."

"Good. And it's ok to...release those urges if you need to." OMG SHOULD I ASK? DO I WANT TO KNOW? ACTUALY, YES I WANT TO KNOW! The tingle was getting stronger.

William looked a little confused. "W-ww-what do you mean?"

Her voice was quiet, almost a whisper. "It's good to be able to release all thet pent up...feelings inside you. Have you...experimented with...you know...touching it?"

"W-w-well...what do you mean?" He knew what she meant. He had done so last night. Twice.

"Do you..."Lena looked around, making sure Jackie was being Lazy Princess....masturbate?"

The look of shock and embarrassment came back, and she realized she shouldn't have said it. "No, it's OK! A lot of people do! Even...I do!"

Oh god, she thought. I just gave him more material for his "spank bank". She dare not tell him about last night's tryst with Gustavo.

"You...you do?"

"Yes, sometimes." EVERY OTHER NIGHT IN FACT, TWICE ON SUNDAYS.

"OH...OK..."

"What do you think about when you do?" I WONDER IF ITS BEEN ME. GOD TELL ME ITS ME.

Her breathing was starting to quicken thinking of him jerking off and moaning her name.

William's hands moved back to his crotch. The Beast was waking up. Lena noticed his eyes darting up and down, realizing he was looking at her breasts. The straps at the top accentuated and puffed out just a hint, accentuating her cleavage. He was hypnotized at the sight, so close he could almost touch them.

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But...she was looking down too, at the stirring member in the bathing suit. GOD ITS ALMOST WRAPPED AROUND HIS WAIST. She could see the very tip of it, lurking to be free. FREE THAT BEAST GIRL!

As both their eyes rose, Williams eyes locked into hers. She couldn't hide the fact she was turned on, and wanting. She didn't want to hide it, either.

"We all just...need it...sometimes." Her voice was almost a whisper. The space between them got closer. She noticed how broad William's shoulders were. He had luscious lips..."why haven't I noticed this before?", she thought. She could feel her breasts heaving now. Their mouths moved slowly closer, her hands taking his arm and awkwardly wrapping around it around her waist...

"MOOOOOOOM, WHERES MY SODAAAA?"

Jackie's voice pierced the sexual tension, and shock, then fear both creeped on their faces.

"UM, SORRY, I HAD TO USE THE BATHROOM!"

She turned to him and put her finger to her lips. Don't say anything, she mouthed silently. WHAT JUST HAPPENED? DONT DO THIS TO ME, LELE. GOD HES ONLY EIGHTEEN.

She grabbed the soda and looked back. "God, I'm sorry..." she hastily said as she walked back out, composing herself enough to face Jackie. She handed Jackie the soda, hoping that she didn't notice her shaking hands.

She laid there, processing what just happened, for what felt like an eternity. Her mind was racing in all sorts of directions.

God its been too long...did you see the way he looked at me...what a sweet boy...hes 18, hes practically a man...im sure hes a virgin...mmmm, what i would show him...STOP! THATS GROOMING! Is it though? I mean...i can show him what a woman wants...only if he does....oh he does, he SO DOES...AM I WET? Shit I'm wet...god I'm gross, hitting on a kid like that. HES A SWEET BOY, HE DOESNT NEED THAT! Maybe he does...I won't let him turn into a douchebag like Colin...Or worse, CHAD...I gotta STOP! But LeLe was also chiming in. MMMMMMM I BET THAT COCK FEELS GOOD...WE NEED A GOOD FUCK GIRL...I BET THAT BOY CAN GO FOR HOURS...IMAGINE THAT IN YOUR MOUTH! FUCK!...WHEN WAS THE LAST TIME? SHIT, THE LAST GOOD TIME?

It had been a long time for sure. Chad was...well, he was awful in bed. His idea of foreplay was, "here's your vibrator, get it ready for me." And he never lasted long. But he thought his 4 inch dick was God's gift to women. Marrying for money wasn't quite worth it to her. And even her first-the last good, time, if any_was ok, not great. Lil LeLe was starting to win the argument. She had never even imagined what a rod like that would feel. But she was beyond intrigued. Especially one attached to a man that she could...trust.

As Lena started to overheat, she decided to take a dip. William was swimming back and forth. She realized he'd been doing it for 30 minutes.

SEE GIRL?

LeLe tightened at thought of her pummeling into her with that youthful energy. A quick jump in and she felt the coolness on her skin, and It was invigorating. William finished his lap and looked up. There was something different in his eyes now...a stirring of confidence.

Of hunger.

He looked into Lena's eyes...she stared back at him. Intensity was brewing. Lena bit her bottom lip. Now she was daydreaming about getting closer...seeing it come out of his shorts...touching it...

He stared back, slightly in wonder, but mostly with the urge of seeing her...kissing her...feeling her in his arms...and hopefully the release of his pent up energy by something other than his hand.

"Hello?" Jackie answered the phone, oblivious to the erotic tension around her. "What? Ya...I think I can...how long? NO CAP!...Yeah, I'll be right there..." some other words tossed in there that could have been another language to Lena. She had given up trying to stay with the lingo.

"Mom, I'm gonna go to Julies." Julie was Jackie's trusted "beard" whenever she went to see Colin and dry hump on his couch.

"What? How long?" Lena's shocked voice did it's best to hide the sudden excitement in it. She glanced over at William, and his gaze told her..he was thinking the same thing she was.

"I dunno...we might go to the mall, go see a movie..." Lena knew this was bullshit, but she played along.

"Home for dinner?"

"Um...yeah, maybe. We'll see." Colin's parents must be gone all day.

"Ok..."

"Should...I come?" William usually asked her this, and wanted a "yeah sure!" But this time he was hoping for a different answer.

Jackie's face tried to hide the nervousness. "Ummmmm...nah....she want to make it a girl thing. You get the vibe."

"Why don't you just hang here? It's a lovely day, William. Gets you out of the house for a bit." Lena tried to hide the hint of excitement in her voice. And she hated the fact he had to go there at all with the situation there. She was sure she was already deep in a martini, and God knows what else.

"Um...I don't...wanna be trouble..."he sheepishly looked at Lena. Jackie was busy texting Julie for her alibi. He pretended to be disappointed, but gave a small smile when he looked at Lena.

"No trouble at all. It's nice to have company." Her smile said all that was needed.

"Thank you Ms. Keefe. Its...nice to have somebody want you around." It was heartfelt. Lena beamed. He bashfully smiled back. Jackie was still furiously texting away.

"This...could happen. What do I do?" She thought. She knew he was nervous. She was absolutely terrified.

But that just excited her more.

About 2:30 is when Jackie headed out for her "mall trip". Lena decided to make a quick lunch for them. "Do you want some salami? I can make you a sandwich."

"Um...sure, Ms Keefe. if it's no trouble." He was starving.

"Please, call me Lena." Her voice was soft, but spilled with seduction. It took her aback slightly to be openly flirting like this.

"Ok...L-Lena. Can I help you with anything?"

"You can grab the water pitcher from the fridge, I'll make us some iced tea."

"Sure, Ms....I mean, Lena." He smiled sheepishly as he grabbed the pitcher and walked over. Handing it over, she looked up at the handsome young man: curly hair with kind, green eyes that shone in the bright kitchen. Those lips...she looked at the soft curves of them, sinfully made for kissing. Their eyes locked for a few seconds, thanked him, and turned away with a bashful but seductive smile that beamed glowing from her lips. It had been a long time since she had.

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