Poolside Lessons Pt. 01

"Morning Ms. Roberts", young Charlie greeted Felicity as he entered her backyard.

"Fuck. What does he want?", Felicity said quietly to herself.

Felicity was looking forward to this day. Her husband is off on one of his big game fishing trips, doing God knows what with God knows who. At this point, she didn't even bother to ask him.

Her daughter Nellie was also finally out of the house, visiting her cousin over the weekend.

This is the first weekend of the summer Felicity had to herself.

"Hey there Charlie, what's up?", she put on a happy face and greeted the young neighbor.

"I came for a quick dip in the pool. Is Nellie coming over soon?" Charlie asked enthusiastically. He was already laying down his towel next to the pool entrance.

Charlie was their next-door neighbor. He returned home from college recently, just finishing his junior year. Felicity's daughter Nellie is two years younger than him. They are good friends and hang out often during the summer.

Charlie is a sweet kid. He helped Nellie when she, Felicity, and Burt moved into the neighborhood five years ago. Nellie was in high school at that time so the move was quite stressful for her but Charlie took her under his wing and introduced her to his friends at school, helping her adjust rather quickly.

Felicity and her husband Burt were always thankful for Charlie that he was around. And their families became friends. As good as any neighbors can be. They frequently have barbeques and birthday parties together.

These gatherings were mostly in Felicity and Burt's backyard since they have a decent-sized pool. And they are happy to host. At least they get some use out of the overpriced pool.

So in a way, Charlie is at home in their backyard. Felicity and Burt insisted he can use their pool whenever he wants. They had to invite him for the first couple of weeks but pretty soon he was coming over all the time.

And that was perfectly fine, it's just that today, Felicity was looking forward to spending some time alone.

"Nellie is out today, visiting her cousin across the city" Felicity declared, hoping to discourage young Charlie from settling in.

"She'll be staying the night", Felicity added with a frown.

"Oh, that sucks.", Charlie answered disappointingly. "I'll just take a quick dip and swim a few laps, then."

"Is that cool with you Ms. Roberts?" Charlie asked enthusiastically.

"Yeah, cool."

But it wasn't "cool" at all to Felicity.

She woke up today smiling, thinking about all the time she'll have for herself. Burt left for his fishing trip last night. All she had to do is drop off Nellie across town to her cousin's and she was free for the rest of the weekend.

Of course, the drive with Nellie took longer than expected. By the time she got back, it was already lunchtime. One quick lunch and a few chores around the house later and it was already late afternoon. But the day was still hers and pool time was almost in her reach.

Soon she was digging through her bedroom closet, but she already knew what she was after. Picking the right swimsuit was easy. She just went for THE skimpy pink bikini. There are no family or friends' opinions to worry about. Burt was giving her the looks when she bought it. He thought it was too revealing.

And he was probably right but Felicity didn't want to admit it because this little bikini accentuated all her best features and made her look ravishingly sexy. The triangle bikini top revealed her ample D-cup breasts. Looking down at her chest, Felicity was pleasantly surprised to see a deep valley formed by her full bust.

Her waist was slender for a 45-year-old. She was also happy with her generous hips that formed a nice, pear-shaped ass, completing her hourglass figure.

She ran her hands over the bikini bottoms. They were hugging her curvy ass nicely and gave plenty of coverage up front for her succulent pussy lips.

When she was trying out swimsuits in the store, the sales girl even assured her that the bikini is not transparent when wet. Felicity knew the girl had caught a glimpse of her neatly trimmed pubic hair while she was trying out the white bikini before.

Strangely, Felicity wasn't embarrassed by displaying herself to the girl in front of the changing rooms. She made Felicity feel good and confident about her mature body.

She remembered the sales girl fondly as she was staring at herself in front of the mirror at home. Now posing in natural sunlight, it looks even better on her. If Burt was around, she would get him to fuck her.

"Well, I guess I'll just have to fuck myself," said Felicity loudly to an empty house as she strolled out of the room on the way downstairs and to her favorite poolside lounge chair.

And fucking was on her mind when Charlie barged into her backyard.

Just a few minutes before Charlie intruded, Felicity was relaxing by the pool and feeling naughty. She was stroking the outside of her labia, feeling how the bikini bottoms hugged her. Her fingers moved to the center of the pussy, tracing the slit over the pink bikini panties.

She was enjoying the long strokes from the bottom to the top of her freshly trimmed pussy. She didn't focus on her clit right away since she had all the time in the world. Felicity was getting aroused just by thinking about openly masturbating in her backyard, enjoying the lazy summer day going by.

And now, here's Charlie with his freshly shaved face and polite manners, come to ruin her day.

Luckily, she had a book by her side to distract her from the ongoing arousal that was still going though her whole body. If she can only remember what she was reading about.

"What's your book about, Ms. Roberts?" Charlie asked, amazingly picking the worst possible moment to intrude for a second time in the last five minutes since he invaded her personal space and time.

Felicity rolled her eyes and took a deep breath. She has had enough. It's time to go on the offense and put him in his place.

"It's Felicity. Not "Ms" Roberts. You should know better Charlie, we had this conversation multiple times over the years." Felicity replied back with newly found confidence.

"Oh right... Ms Felicity... I mean, Felicity" Charlie muttered, taken aback by her forwardness.

"How's college going Charlie?", she picked a new subject to probe.

"Fine, I'll be a senior next year. Yeah, college is fine." answered retreating Charlie.

"Any girls?"

"No."

"Why not?" Felicity continued her rapid-fire questions.

"I don't know. They are all just cold and not interested."

"Not interested in you?" Felicity paused and smiled a little, sensing she touched on a delicate subject.

"Yeah... No" Charlie muttered as he averted his eyes from Felicity. "All they want to talk about is school and their Instagram accounts"

Charlie started to push back "These girls are not interested in dating anymore. Or just having casual fun. It's so hard."

"Oh dear Charlie, I assure you, girls ARE interested in having FUN." Felicity stood up for her younger friends. "Did you try asking them if they are interested?"

"Yeah, I guess."

"Well, you need to make a woman feel wanted. You need to work on it. Make them feel safe with you, but also... sexy." Felicity explained.

"I did Ms. Roberts! I did work on it!" Charlie snapped back.

Felicity took a moment. She wasn't angry at him anymore. It's not his fault that he barged into her free time. She felt the young neighbor's frustration and decided to offer help with s more gentle approach. "Are we friends Charlie?"

"Yes, of course."

"Well, why don't you come here and show me how you talk to girls?" she was gesturing to the spot next to her.

"What do you mean?" Charlie moved to take the seat closer to Felicity.

"Pretend you're interested in me. Romantically. What would you say to get me interested to go back to your room?" Felicity said in a calm voice of a teacher.

"I don't know. It depends. Maybe I ask if she wants a drink", he muttered, hoping to get the right answer.

"Me, Charlie. You're talking to me and I'm already drinking hard lemonade. Why don't you try something else to get me horny." Felicity stared at him directly.

"Well, it's a nice bikini" Charlie tried desperately, looking at Felicity's voluptuous bikini-clad body, spread on the floor next to the pool.

"What's nice about it? Describe it to me."

"The color."

"And..." Felicity arched her back to accentuate her bikini top that was barely holding her full tits.

"The shape is nice."

"What about my breasts? Don't you like how they fit tightly in this bikini top?"

"Yes", he answered quietly.

"Well, you should have said something then. You can be more direct with me".

"And how's the bottom half?" Felicity turned to her stomach, exposing her bikini bottoms that hugged her round behind. "Remember to be very specific. Make me feel desirable."

"It's amazing."

"Yes. That's better. What's amazing?" she encouraged him.

"Your ass", Charlie said very carefully.

"My ass?", Felicity smiled and swayed her behind inviting him to compliment her more.

"It's so... juicy. I could stare at it all day."

"Mmhm" she let out an affirming moan. "Keep going. How does it make you feel"

"Hard", Charlie blurted out.

"Good. I like hearing about how my ass is making you HARD", she assured him.

"To be honest, this is making me harder than the girls at college I was with."

"Well Charlie, you'd be happy to hear that you also managed to make me all excited." Felicity declared as she turned to her side to face him. "See what a few sexy words can do?"

Felicity wasn't lying about being excited. Even before Charlie came she was ready to put her fingers inside her bikini bottoms to stroke her clit. Now, she was on fire and her young neighbor was in facing her, with a visible bulge forming on his swimming trunks.

She still wanted to have fun with Charlie without crossing the line, but right now she needed relief, and quickly.

"Now that you got me all horny, I need you to go inside the house and get my vibrator. Can you do that for me, honey?" Felicity asked, giving him a pleading look.

"Of course. Anything"

"Good boy. Go to the master bedroom and look in the dresser. It should be in one of the drawers." Felicity instructed her young student. "Actually, just take your phone and call me, I'll guide you".

Charlie was walking in through the dim hallways of the house. He's been here dozens of times, but this time it felt different. His blood was pumping faster, only engorging his erection as he was listening to Felicity's instructions through the phone.

He quickly found himself in the master bedroom. Felicity and Burt's room was probably the only room he hadn't been in before. The bed cover was messy since Felicity didn't expect any visitors. Her blouse was on casually thrown on the bed together with a pair of dark pants and a white half-cup bra. On the floor next to the sandals, lay a pair of black panties with lace trim that Felicity casually slipped off before she started digging through her closet, looking for the infamous pink bikini.

"Try the bottom drawer first" Felicity's husky voice came through the phone. It snapped Charlie back from his long stare at the black panties casually left on the floor.

"Right," he responded as he kneeled to open the bottom drawer of the dresser. "And what am I looking for?"

"A blue vibrator, it looks like a lip gloss, only bigger. It should be somewhere behind my lingerie" she explained, making sure to emphasize the last word. "Maybe you'll need to dig through it."

Charlie's hand was blindly feeling the undergarments, one by one, in search of the blue toy. His excitement grew when he felt a hard object in an open box at the back of the drawer.

"I found something, but it's black" Charlie reported confusingly.

"Black? Ah, that's my dildo. I forgot that's in the bottom drawer." Felicity responded chuckling. "Well, maybe it will come in handy. Is it clean?"

"Clean? I don't know. It looks clean."

"Well, if it looks clean it doesn't mean that it actually is. I don't remember when I last used it." Felicity said more to herself than Charlie. "Hmm, does it feel... sticky?"

"Not exactly," he answered while his hand stroked the black phallus. He had a difficult time keeping up with the conversation and processing that the smooth silicone toy in his hand was in Felicity's insides at some point.

"Why don't you smell it then?" she pushed on. "If it's clean it should smell like my lingerie at least."

If Charlie wasn't so confused and horny, he would've heard a small moan escape from Felicity's throat over the phone. She was enjoying this newly found alone time at the pool. Her fingers were back on her pussy, but this time being more direct and invasive. The thought of a young man digging through her sexy lingerie sent her to overdrive. Pretty soon she had two fingers lodged into her dripping insides.

"Huh?" Charlie was now completely lost, asking for help from his married neighbor.

"Take my panties from the drawer and smell them. Then, you smell the dildo. It should smell similar if it's clean" she instructed. "Don't be shy. I NEED you."

Encouraged by Felicity's instructions through the phone, Charlie's eyes focused on the small thong that he was handling before. He brought the delicate item to his nose and inhaled like it was his last breath on Earth. The sweet flowery smell filled his nasal cavity, firing the neutrons in his brain. The signal sent even more blood to his cock, now forming a raging hardon.

He was in a delirious state when he switched to the second part of the task - smelling the silicone dildo. He pressed the side of the dildo so hard to his nose that his lips touched the sacred rod that was once graced by the presence of Felicity's pussy.

"So, does it smell like my underwear", Felicity snapped him out of the trans again.

"No" Charlie answered stoically.

"Hm, too bad. I guess I forgot to clean it last week. Ok, just leave it. I'll probably want only something on my clit anyway, I can do it without penetration."

"Maybe check my nightstand. It only has one drawer."

Charlie almost forgot what he was originally looking for but there it was: a neon blue lipstick-shaped vibrator snugged in the nightstand's drawer.

"Aha! Got it!" Charlie declared victoriously.

"Great, just check that it works first. Turn it on. There's a button on the bottom". Felicity asked cautiously.

"Nothing is happening," Charlie said confusingly after pressing the button multiple times.

"Oh, the battery is probably dead again" Felicity brushed it off, hinting that it happens regularly. "Shit, I don't know if we have any batteries..."

"There should be some in Nellie's room" she declared enthusiastically. "Just pop into her room and get some from a remote or something."

It felt weird to Charlie to be in Nellie's room with a raging erection, holding her mother's vibrator. He thought of her as his younger sister at first but recently, his perspective was changing, especially this summer by the pool. At first, he struggled to keep these invasive thoughts out of his head as Nellie paraded in front of him in shorts and tank tops. Her hips and ass filled the shorts as they struggled to cover the bottom half of her behind. Armed with a pair of perky tits and a cute face, Charlie was left defenseless against the constant attacks on his decency.

"Is there a remote or something else with batteries?" Felicity pressed on, urging him to continue his quest.

"Let me see" Charlie turned around scouting the room dressed in swimming trunks that restrained his erection.

His young age and familiarity with Nellie's room proved useful this time. In only a few seconds he found a wireless mouse on the desk. He stripped away the prized battery from its guts and revived the blue vibrator to its full potential.

"Great job Charlie". Felicity smiled as she eagerly snatched the vibrator out of Charlie's hands back at the pool. "You're such a good boy".

"Now here's what's going to happen, I am going to lie here and use this vibrator to pleasure myself." Felicity declared as she laid back, spreading her voluptuous body on the tiled floor at the edge of the pool. The same spot she managed to finger herself to an orgasm while Charlie was smelling her dildo, just a few minutes ago.

But that was just a warmup for Felicity. Her masturbation sessions always get her over the top multiple times and she decided that today will be no different, regardless of the guest that showed up uninvited.

"It's been a long day and I deserve something for myself," she continued. "You've been very helpful in finding my favorite toy so I'll let you stay."

Charlie was still standing above her with his engorged hardon, looking down on Felicity as she stroked her panties with the vibrator.

"You can sit over there and watch," she instructed as Charlie took a seat opposite of squirming Felicity.

"And let me make it clear again. I'm going to masturbate here in my own backyard and I'm letting you watch. You are also free to leave at any time. But I don't want you talking about this with anyone. Got it?"

"Yes, Ms." Charlie nodded.

"Gooood." Felicity sighed as she turned on the vibrator and pressed it against her pink bikini panties that were generously soaking up her juices and covering her guilty pussy.

She played with the settings until she found a wave pattern that was teasing her clitoris, hidden behind the panties.

"You know, it's ok to help yourself," Felicity spoke softly to Charlie whose gaze was locked on the pink triangle mesh between her bountiful thighs. "I can see your swimming trunks are holding you back. It's ok to take it out and masturbate".

Encouraged by Felicity, Charlie opened the front of his trunks, releasing his cock. It felt wrong to have it out in the open in his neighbor's backyard. A place where he spent the last few summers with Nellie. The feeling of guilt was instantly replaced by pleasure when his hand started stroking his raging member.

Felicity smiled to herself as she watched her neighbor vigorously handle his young cock. Its hefty size wasn't surprising to her since she's already seen the outline of his swimming trunks multiple times, even before today.

The air was filled with heavy breathing from both culprits when Felicity moved the bikini panties to the side, revealing her full pussy lips with a pulsing clitoris on top.

An unsurprising moan came Charlie as he watched Felicity's reveal. His cock was already shining from the precum that lubricated it, increasing his pleasure even further.

Felicity welcomed a new sensation as her bikini panties stretched and applied pressure to her butthole.

The blue toy was now on top of her clitoris, feeding its vibrations directly to her pleasure systems.

Her two fingers, already fully wet, pistoned in and out of her pussy, bringing her to the next level of sexual excitement and bringing down the last barriers of dignity.

"You know Charlie, I think I changed my mind," Felicity announced with her eyes closed.

Charlie worriedly snapped back from his focus on Felicity's newly spread legs that gave him an unobstructed view of her finger-filled pussy.

"I should've asked you to bring that black dildo. I wouldn't mind some penetration now."

"I'll bring it over now!" relieved Charlie jumped up instantly.

"No. I can't wait! Maybe... you can help me?" " pleaded Felicity.

"I can use your nice cock. I just need some penetration to come."

"Can you help me out, Charlie?" Felicity was running her two fingers down the sides of her outer pussy lips, enticing her young neighbor.

"Of course, Ms Roberts," he mumbled and cautiously moved closer to her by the edge of the pool. His shiny cock led the way.

"It's... Felicity" sighed the married vixen as her hand guided the neighbor's young cock into her dripping opening.

His engorged member filled her insides, scratching the itch that her fingers just couldn't reach.

"Ooooh.. that's good" Felicity praised her young student. "Now you just hold still while I take care of myself".

Charlie stayed motionless, gazing down at Felicity's hips as they started gyrating around his cock. He couldn't believe it was happening. Just an hour ago he felt bad for checking out Nellie's mom in her skimpy bikini and now his cock was engulfed by the thick folds of her pussy.

Her juices were soaking his cock and making their way down his scrotum. Charlie didn't know women can get so incredibly wet. He was thankful he jerked off this morning or else he wouldn't make it this far without bursting.

A familiar blue toy appeared in Charlie's view again as Felicity pressed the vibrator on the hood of her clitoris.

Her hip motion changed from gyrating to back and forth. Felicity couldn't believe how hard it was. Almost like a wooden stick attached to a wall.

She remembered the last time her husband's cock felt this hard. It was during the fucking Burt gave her after the Christmas party at his company. They were bickering the whole drive on their way back from the office party. Felicity made some comments about Burt's new assistant. The young blonde was very comfortable around Burt, touching his hand, and pressing her tight little body while talking to him at the party. And Burt wasn't shy either. Felicity caught him sliding his hand down the back of the assistant's party dress and over her pear-shaped Millenial ass.

Burt called her a jealous housewife but Felicity knew there was something going on. She didn't need to hear him confess, his actions spoke clearly. When they arrived home, Felicity hiked up her black satin dress, slipped off her black thong, and climbed on their bed.

She was on all fours, dress hiked to her waist, heels still on, ass raised in the air when she invited Burt to confess his desires: "I want you to fuck me hard right now, mister Vice President".

Felicity continued her teasing by rubbing her moist pussy. "Show this young office slut how the big guys do it".

The proof of guilt came in the shape of the hardest cock Burt provided Felicity in ages. The pulsating beast that invaded her insides made Felicity provoke it even further. "Oh yeah, yeah. Just like that Mr. Roberts. Show my little bold cunt who's the boss."

Felicity wasn't planning it but it seems she finally got her revenge in the form of the young cock, provided by their neighbor Charlie. Right there in the backyard, next to the pool, her naked ass was spread on the floor, feeding her hungry cunt a big piece of fresh meat she deserves.

Felicity switched from gyrating to clearly fucking Charlie's cock now. Her abs and hips working together to give her slutty pussy what she desperately needs.

"Oooo fuck" Facility proclaimed as she found the rhythm that will get her over the finish line.

She spread her legs even further and pulled them back in a desperate attempt to open her pussy more to Charlie's wonderful cock.

Her asscheeks repositioned closer to his legs. She was sitting below his cock now.

"Ah... ah... ah... ah... that's it."

Felicity's hips continued pounding the young cock.

"Holy fuck... ah... ah... ah."

Her stretched legs and ass left her butthole exposed, sitting below Charlie's tightened scrotum.

"Yes... Ah! Yesss.... That's it"

That extra anal pleasure from Charlie's ball sack caressing her anal region was lost on Felicity as she started thrashing her body uncontrollably.

"Ah... ah... ah" Felicity gasped for last breaths of air.

"Eeeeiii" she squealed as orgasm ravaged her body.

Her pussy started gushing, expelling the sticky nectar over the captive cock.

Her once-working body turned into a puddle of flesh and sweat.

The pulsating blue vibrator was sitting now uselessly on her belly, as Charlie retreated his ever-hard cock from her mushy insides.

"Well..." Felicity spoke after forever, her eyes still closed in a post-orgasmic bliss.

"That was very good. Thank you for your help" she opened her eyes, smiling at the college junior.

"My pleasure ma'am," answered Charlie politely.

"No, it was MY pleasure." teased Felicity. "You were so helpful. I'll feel I need to reward you."

She moved her hands on her sticky pussy, giving her clitoris a few gentle strokes. She was pleasantly surprised that her body responded positively, still hungrily accepting signals from the erotic center.

She watched the young student as his gaze followed her hands move over her belly to her generous breasts.

She stroked her bikini-clad hills and circled her fingers around the protruding succulent nipples, all under the watchful eye of her young apprentice.

Her fingers snatched the pink bra from both sides and pulled the triangle mesh apart, revealing her full double D breasts to the startled audience.

"Why don't you finish on me... I want to watch you come." Felicity continued with her poolside lessons.

End of part one.