Love Lessons at Pleasure Point 03

Welcome to the third chapter of my latest series. Please remember to rate and comment. Merci, Petitmort

As the halcyon days of summer began to fade into fall, Paul found himself spending more and more time at two bungalows in Pleasure Point.

Here he was, a few weeks shy of his 21st birthday, carrying on torrid affairs with not one, but two, singularly attractive older women.

When he wasn't surfing, he was spending his days working in their gardens, doing odd jobs and, of course, making love.

Maddie was still giving him "love lessons", tutoring him in all things sexual, and then letting him practice on her late into the night.

Allyson was employing him as a part-time model, mostly in the nude, and as a full-time muse for her now reinvigorated artistic career.

It just seemed to make sense for him to sleep there too.

Paul had mentioned to Maddie he'd been couch surfing for the past month. Ever since his ex-girlfriend Siobhan moved to San Diego.

He was biding his time until the fall semester started at Cal State Monterey Bay. He'd been planning to find a cheap place to live near campus.

When Maddie suggested he move in with her, he jumped at the chance.

Allyson was thrilled that Paul would be living full-time next door. She'd been infatuated with him ever since their sizzling hot photo session in her art studio.

They ended up having amazing sex sitting in an easy chair. She later told Maddie it was practically a religious experience.

She was only half-joking.

Afterwards, when Paul left her sleeping in her bed and slipped in the back door of Maddie's cottage, he felt a bit apprehensive.

How would Maddie react now that he'd had hot sex with her best friend and neighbor?

It's true, she did encourage him to help bring Ally out of her shell.

But still.

In the darkness, he took off his clothes and slipped between the sheets of Maddie's bed. He slid his body close to hers, feeling her warmth.

He spooned her from behind.

He felt her hand softly caress his thigh. Her touch was loving.

"How'd it go with Allyson?"

"It went fine," he said softly. "She took a lot of pictures."

Maddie lifted her head slightly.

"Were you nude?"

"Yeah. She said it was normal."

"It is," Maddie replied. "Did you make love?"

Paul felt a well of emotion in his chest. He didn't want to hurt her, but he knew he had to be honest.

"Yes."

There was a pause.

"Did she enjoy it?"

"Yes."

Maddie lay her head back on her pillow.

"Good."

She wiggled her body to get closer to him. He put her arm around her and she held it with her own.

The next day, nothing seemed all that different between the three of them. Maddie was as cheerful as ever. And Ally, when she came over with a bag of bagels, had a big smile on her face.

They both seemed perfectly fine with it.

They were such good friends, they just let it be. It was like they were willing to share him. Like they did everything else.

Paul still used Ally's outdoor shower every day. Just like before. He'd slip through the bushes that separated their backyards and shower in the open air.

Except now, he showered naked.

He figured, since he'd already posed naked for Ally, and then the two of them enjoyed an hour and a half of orgasmic chair sex, she'd seen everything anyway.

So, instead of wearing his bathing suit as he normally did, he just let it all hang out.

Ally would still come out, every day, and sit in her chair, chatting with him, watching him while he showered. Just like before.

He'd be washing his hair, with the suds streaming down his muscular body, and his long cock hanging between his legs.

And when he was done, she'd dutifully wrap him up in a plush towel and help him dry off.

Being a full foot shorter than him, she was particularly good at drying his lower body. So, she'd spend extra time toweling his thighs and buffing his butt.

She made sure his cock and balls were nice and dry too.

Invariably, his cock would begin to lengthen and get hard.

And Ally would just smile.

Sometimes it would lead to sex, sometimes it wouldn't. But it always left her feeling younger and happier.

Over time, Paul, Maddie, and Ally fell into a comfortable routine. Paul would spent Monday and Wednesday nights with Maddie, and Tuesday and Thursday nights with Ally.

He spent his weekends hanging out with his friends.

They came to this arrangement not just because they wanted to share Paul equally. They seemed to know, intuitively, that switching things up was healthy and would keep things feeling varied and fresh.

It was just the right balance of structure and surprise to keep things exciting. A kind of predictable randomness.

For Paul, the arrangement was the best of both worlds. He found both women incredibly attractive, but for entirely different reasons.

He'd had a crush on Maddie for years. His favorite teacher in high school, she was tall and alluring, with a sexy and even regal bearing. Like Audrey Hepburn in Roman Holiday. She had the face of a goddess, long legs, womanly hips, and absolutely gorgeous breasts. In the daytime, there was a kind of teacherly formality about her. But at night, when he got her between the sheets, she turned into a wildcat.

He loved melting her frosty exterior and discovering the horny harlot underneath.

Ally was, in some ways, Maddie's opposite. Just an inch or two over five feet, she had a petite, ballerina body, with perky little breasts, a slender waist, and a tight, shapely butt. She was artistic in every sense of the word, with a quick wit and a caustic sense of humor. She was less experienced sexually than Maddie, but she made up for it with enthusiasm.

Most of the nights spent with Maddie were a continuation of the lessons she'd started that first week. She found Paul to be a quick study and she soon found herself moving on to more advanced techniques.

First, she'd introduce a new element of lovemaking, sometimes with a literary excerpt to make it come to life. She'd take him through the basics and then he'd show her what he learned.

As the night wore on, they'd segue into free time, a kind of independent study, where they enjoyed unstructured, no-holds-barred sex. Anything goes. Whatever inspired them in the moment.

One week, they spent both nights focused entirely on cunnilingus. He spent most of the time licking, sucking, and probing her pussy with his tongue and fingers.

She taught him exactly how she liked it and he kept practicing, over and over, bringing her to orgasm again and again.

Another week, she introduced him to the fine art of anal sex. She tutored him on how to get her ready using his fingers, butt plugs, beads, and other toys. She taught him how to take it slow, letting her adjust to his size, before really going to town.

And they spent quite a few nights role playing. Paul especially enjoyed the teacher-student scenarios because they hit so close to home.

One night was particularly memorable.

She set up some hard-backed chairs in the middle of the room facing her desk. She was wearing a tight fitting blouse with a push-up bra, the top two buttons were undone.

There was a knock on the door.

"Yes?" she said, sternly.

Paul peeked in, tentatively.

"Oh Paul. I've been expecting you. Come in."

She told him to shut the door and take a seat. He did as he was told.

"Paul, I noticed you weren't particularly attentive in class today."

"No, I was paying attention. Really..."

"No, you seemed to be distracted. Like your mind was focused on something else."

"Um, if I was, I'm sorry..."

She walked from behind her desk, revealing a short skirt and sexy spiked heels.

"Was there something about the lesson that you found boring?"

"No, not at all..."

"Or, perhaps, it was something about my teaching that you found less than engaging?"

She stood in front of him, her legs slightly apart, and took off her glasses.

"Or maybe it was the way I'm dressed today that distracted you?"

He gulped.

"Is that it? Was it because I'm wearing a skirt that shows more leg than I normally do?"

"I"m not sure, um..."

"Or, maybe it's this blouse, and the bra I have on underneath, that make my breasts look larger than they usually do."

"I dunno. I just..."

"I noticed, when I came by your desk, that you seemed to be somewhat... uncomfortable."

"No, I wasn't..."

"When I stood next to you, I noticed you were covering yourself."

"Covering myself? No, I..."

"Then, when I took a closer look, I saw that you were physically aroused."

"I swear, I wasn't..."

"No, when I leaned over to check your work, like this, and my breasts got very close to your face, I definitely noticed you were extremely aroused."

"Honest, I couldn't help..."

"Now I realize, with the blouse I'm wearing, you might have gotten a glimpse of my lacy bra. Or perhaps you could see the outline of my nipples pressing against the sheer fabric. Is that what happened?"

"Um...."

"Were you imagining what it'd feel like if my breast accidentally brushed against your face? Or if you could feel my firm nipple softly touching your cheek?"

He gulped again. She straightened up.

"Paul! You're... you're aroused right now! I can see the bulge in your pants!"

"It just sorta happened..."

"Oh my goodness! Yes, you are most definitely aroused! Good gracious! You must be extremely aroused because that's a very large bulge!"

"I'm so sorry, I didn't mean to..."

She looked at him and sighed.

"Oh, Paul! What am I going to do with you?"

"I feel terrible, Mrs. Engle. Really I do."

She gave him a sympathetic look. Then she cradled his head, pulling him to her.

"Shhhhh, it's okay. It's a normal reaction for boys your age."

Her hands were holding his head, stroking his curly hair.

"I'm just concerned about you, Paul. If you don't pay attention in class, you might fall behind. And that could affect your grade. I wouldn't want that to happen. I care about you, Paul."

"I know you do, Mrs. Engle. I want to do well in your class. I really do. I'll do anything to make up for it."

She pulled him close to her body, his face pressed against her full breast.

"I feel like you won't be able to concentrate until you get this out of your system. I feel like you need to take all that boy energy, and that... stuff... that's building up inside you, and just... eject it."

"Eject it?"

"In one, big, powerful ejection. Do you think that'd help you concentrate?"

"Um, yeah. I guess so."

"Yes, I definitely think we need to do that. But first, I want to see how big this problem is that we're dealing with. Paul, pull down your pants."

"Huh?"

"I said, I need to see just how big the ejection needs to be. Pull down your pants."

He gulped and pulled his sweats down to his ankles.

His erection was massive.

"Oh Paul. It's a much bigger problem than I thought! My goodness! You're going to need more than a simple ejection. You're going to need an enormous ejaculation!"

"I'm willing to do anything..."

She started to unbutton the front of her blouse.

"I know you are, Paul. Now, don't worry, I'm going to help you. Why don't you start by pulling off my panties."

He reached under her skirt and slowly pulled her panties down her thighs. She pulled off her blouse and unclasped her bra.

Her breasts were large and luscious, her nipples sticking out.

She guided his face to her breast.

"Start by licking my nipples, Paul. That's it. Now, wrap your lips around them. Good. Now, I want you to suck them."

He was sucking her erect nipple into his mouth, pressing her grape-sized nipple to the roof of his mouth with his tongue.

She reached down and started to stroke his huge cock. She could barely get her fingers all the way around it.

"I'm only doing this to help you concentrate. To help you be the best student you can be."

She swung her leg to straddle him, facing him.

"Now, I want you to rub the head of your penis against my vagina. That's it. And suck the other nipple. Make it big and hard too."

He was rubbing his bulbous head up and down her pussy. She was so warm. So wet.

He unlatched from her nipple and looked up at her.

"You're really wet, Mrs. Engle."

"Yes, I know I am, Paul," she said breathlessly. "That's because I love what I do. Teaching young people such as yourself. Turning boys into men."

"I appreciate it a lot, Mrs. Engle."

"I know you do, Paul. Now put that big thing inside me. I want you to pump all that boy energy out of your body. And put it into me. Do you hear me? I want you to pump every last bit of your boy energy into me."

She lowered herself onto his cock, bottoming out.

She let out a yelp.

He started to thrust into her, causing her big breasts to bounce.

"Yes! Yes! Like that! Exactly like that!"

He was lifting her, knifing his cock into her dripping wet pussy.

"I love how you're applying yourself, Paul. You're doing an excellent job!"

His muscular arms were wrapped around her, his face was buried in her breasts.

His pelvis was pounding her. She was crying out with every thrust.

"Oh, Paul! You're doing so well! This is A+ work!"

She lay her head back as he sucked her nipples, her arms around his neck.

"Keep pumping it in me! Pump it really hard!"

He stood up, lifting her. She wrapped her legs around his waist.

He was slamming his cock into her. Over and over. She was shrieking with every thrust.

"Ahhhhhhhh! Yes! Yes! Give it to me! Give it to me hard!"

He carried her to the bed, laying her on the edge. He stood on the floor, hammering her, fast and hard.

"Aaaaaaaiiiiiiiiiieeeeee!" she screamed.

He was using the floor for leverage, thrusting into her with his whole body. Her arms lay above her head, her big breasts bouncing.

Her body convulsed as she came, her arms flailing.

He kept pummeling her pussy. She came again and again.

"I'm gonna cum!" he finally groaned.

"Yes! Yes! Shoot it! Shoot it all in me!"

He exploded inside her, shooting a huge load deep in her pussy.

His orgasm seem to last for the longest time, his body twitching and spasming.

He collapsed next to her, breathing hard.

"Well done, Paul!" she gasped. "Very well done!"

Whatever Maddie chose to teach him, Paul committed totally. He listened well, asked questions, and then practiced and practiced, until he thoroughly mastered it.

Maddie was amazed by his seemingly boundless sexual appetite. No matter how many times they did it, how many times he shot his load, he always seemed ready and eager to do it again.

She'd made a point of teaching him that a good lover always brings his partner to orgasm first. He took that instruction to heart, bringing her to orgasm three or four times before finally filling her with his hot cum.

And because she was teaching him the very things that turned her on the most, she would end up cumming over and over again.

Practice, after all, makes perfect.

Now, the nights Paul spent with Allyson were wholly different, yet equally memorable.

Allyson was an artist through and through. Her work in drawing, painting, and photography had been exhibited in galleries throughout the area. She was an accomplished writer too, contributing stories to a popular erotic fiction website.

She looked at life through a completely different lens than Paul did, which is probably why they got along so well.

The first time Ally invited Paul to pose for her, she started the session by asking him to take off all of his clothes. This wasn't atypical when she worked with models, with one major exception.

With Paul, she designed the whole whole rest of the session to make him as aroused as possible.

Then, she took off her own clothes and... well... the rest is history.

They ended up having back-arching, toe-curling sex that had her moaning in ecstasy.

It was the first time she'd been with a man in years.

Ally hadn't had that many sex partners in her life to begin with. She married her husband while she was still in college. He was older than she was and, years later, he would die suddenly from a defective heart valve. She went through a prolonged dry spell that lasted more than five years.

Then, she made love with Paul.

Afterwards, when she told Maddie about it, she said it was the best sex she'd had in her entire life.

From the first time she met Paul, Ally had been drawn to him. In addition to being tall, dark and handsome, with a picture perfect physique, he had the most beautiful cock she had ever seen.

Not that she'd seen that many.

Her husband was small to medium sized, about five inches fully erect. Paul was a full nine inches at least. And he was thick. With beautiful contours and golden brown skin. She loved to take him into her mouth and throat, feeling him growing bigger and harder. And when he pushed his cock into her pussy, he went where no man had gone before.

She felt so stretched and full, it was heavenly.

She found herself thinking about him all the time. Remembering what it was like the last time they made love. Anticipating the next time. When it wasn't her night to be with him, she'd lay in bed fantasizing about having sex with him. Sucking his cock. Making him big and hard. Riding his beautiful cock.

She'd come up with elaborate plans for their nights together. Usually, that involved an art project of some kind. They would spend hours in her studio creating together. Sometimes he would work alongside her. Other times, he'd pose for her. Their work spanned all media. Sketching. Painting. Photography.

One of her more audacious projects was a series of nude sketches.

It was inspired by the photographs she'd taken of Paul that very first day.

In their first session together, she had Paul lounge on an easy chair, totally nude, illuminated only by natural light. He looked like a Roman gladiator, his muscular body draped languidly on the arm of the chair, his prodigious cock hanging between his legs.

She had set up her camera to document the session, using time lapse.

She began by telling him an erotic story. As the story unfolded, she stripped for him, applied perfume to her naked body, and turned to show him her newly shaven pussy.

When she went back and reviewed the photos, she was astounded.

The images were a progression of stills of Paul's gorgeous body, bathed in subtly changing light, as his cock grew bigger and bigger and bigger.

All because of her. Her voice. Her body. Her very presence.

That she could inspire such a transformation in this beautiful man was a huge confidence boost for her.

She decided her next work would be a series of nude sketches with Paul as the model.

She would call the series "Arousal".

Inspired by Monet's famous "series paintings", she used three easels and then moved between them as conditions changed.

Whereas Monet moved from easel to easel as the light changed, Ally did so as the size of Paul's cock changed.

The first sketch showed a totally nude Paul sitting on the arm of the easy chair, his legs splayed, his cock hanging like a baby's arm holding an apple.

The second sketch showed his cock in a semi-erect state, taut and tumescent, the head swelling with desire.

The third and final sketch showed his cock fully erect, long and thick, as if it were about to explode.

Ally was standing behind the first easel now, dressed in a short, white artist's smock which was unbuttoned down the front.

She had nothing on underneath.

"The light's perfect, hold that pose," she said, adding some shadowing to the sketch.

Paul was laying back on the easy chair, with his legs splayed. His cock was already looking impressive.

"Now, remember, you're watching your lover and she's undressing for you."

Paul was watching Ally work, her face a picture of pure concentration. She was working quickly, sketching something, then glancing up at his naked body every few seconds.