Love Lessons at Pleasure Point 02

"I'm gonna fucking cum," he growled.

Maddie raised her pussy even higher. To take him deeper.

"Fill me up! Fill me with your cum!"

He held her hips and leaned back, his ass flexed. He was as deep inside her as he had ever been.

"Shoot it, Paul! Shoot your cum in me!"

He held his cock deep inside her.

He felt a torrent of cum explode out of his cock. Again. And again. And again.

He was so big, her pussy could actually feel his cock throbbing. And his warm cum spraying her insides.

"Arrrrrggggghhhhh!" he groaned.

He kept cumming and cumming, riding the aftershocks for the longest time.

Her body finally gave way and she collapsed onto the bed. He slumped on top of her, his weight a welcome salve.

She knew she would not soon forget this. The way his penis felt inside her. The incredible pleasure he had given her.

She also knew she was going to have one helluva talk with Allyson.

Later, as Paul and Maddie stood in her little kitchen making coffee, the mood was light and playful. Like two teenagers who suddenly discovered they both had crushes on each other.

The irony, given the age gap between them, was not lost on either of them.

Paul broke the levity with an earnest question.

"When I told you your neighbor was watching us make love, you said 'poor thing'. Why?"

"Allyson's a widow. She's a dear, dear friend. I've known her for years. She lost her husband five years ago. She's been alone ever since."

"That's sad."

"Yes, it's very sad. She's still an attractive, vibrant woman but that part of her life just evaporated."

"A lonely widow?"

"A lonely, sexually frustrated widow to be exact. She's intelligent, funny, artistic — she'd be a wonderful partner for someone — but she's hasn't had the courage to take that next step. Meeting and getting involved with a man."

"There's an app for that. Lots of 'em in fact."

Maddie nodded.

"Oh, she's tried all of 'em. Elite Singles. OK Cupid. Complete disaster. She can't do the whole small talk thing. Either she clams up or she overshares and scares them away."

"It seems like she's pretty relaxed sexually. From what I can tell. I mean, she seemed to be enjoying watching us go at it."

"That may have been my doing. I saw her this morning. She came by to check on me. I told her about you. And about how much I enjoyed our time together last night. I think I may have created a monster."

"Sex-starved widow goes wild?"

Maddie chuckled.

"I'll check on her later," she said, pressing up against him and giving him a kiss.

He kissed her back, pressing her against the refrigerator.

"You're so sexy."

He was nuzzling her neck, his hands on her torso.

"Careful. You're going to get me all hot and bothered. Then I'm gonna want to take you right back to bed."

"Let's do it. I'm ready."

He was kissing her now, his hand slipping under her panties. She pushed him away, laughing, and feeling his hardening cock.

"You are ready. God, I love your libido."

"My libido loves you."

She gave him a sultry look and slipped away.

"I've got things I have to take care of. That storm last night wrecked havoc on my garden. I've got to get it cleaned up and fill my compost bin before the garbage pick up tomorrow morning."

"I can help you with that."

"You're on. You know, there's one other way I think you might be able to help."

"Yeah, what's that?"

"Maybe you can help Allyson out of her shell."

Allyson Cohen, had been Maddie's neighbor for more than 25 years. She and her husband bought the cottage next door to Maddie's as a vacation home. He was a successful lawyer. She was an aspiring artist, photographer, and writer.

Allyson was an attractive, if somewhat mousy, woman with intelligent eyes and a caustic sense of humor. She bore a resemblance to the actress Frances McDormand.

She was small, just over five feet, with a petite figure she kept in excellent shape by yoga, hiking, and biking. She had lovely, small breasts, narrow hips, and an adorable butt. But she spent most of her time in cheap eyeglasses and little makeup.

She looked like she could be the local librarian.

Allyson first met Paul when she saw him and Maddie working in her backyard. They were cleaning up after the storm, raking leaves, and cutting up some downed tree limbs.

She came over with a pitcher of lemonade while they were taking a break.

"Allyson, you shouldn't have."

"Of course I should. I saw you two working your tails off and I figured I'd be a good neighbor."

She turned to Paul.

"Hi, I'm Allyson," she said nodding to Paul.

"Nice to meet you. I'm Paul."

He stood up, shirtless, and smiled at her. At 6'1", he was a good foot taller than she was.

She turned and look at Maddie. Her expression read, "is he for real?"

"O. M. G." she said to Maddie.

"So, you're a friend of Maddie's?" she asked, turning to Paul.

Maddie rolled her eyes.

"Well," Paul answered, "I've known her for a long time. I was her student."

Allyson looked at Maddie with raised eyebrows.

"Oh, her student. How interesting! When were you her student?"

Maddie just smiled. It was clear she was trying to do the math about his age.

"Paul's 20, Allyson," Maddie interrupted. "If that's what you were driving at."

"I wasn't driving at anything," Allyson protested. "Just taking a little stroll. I was just wondering how the two of you met."

"I was in her English class at the high school. She was my favorite teacher."

He gave Maddie a smile.

"Oh, was she? Well, that explains a lot then."

"She taught me more than any teacher I've ever had. And she's still teaching me things."

Allyson looked at Maddie with a knowing smile. Maddie just smiled back at her.

"Paul's going to Monterey in the fall to study environmental science," Maddie said. "He needs a place to stay in the meantime. I've invited him to stay with me."

Allyson nodded, knowingly.

"I'm gonna help Maddie out with some things around the house. Maybe fix up the studio above the garage."

Maddie looked at Allyson again.


"Paul's very good with his hands."

"Oh, I'm sure he is," Allyson said, with a snort.

Maddie looked like she just thought of something.

"Paul's looking to make some extra money. To pay for college expenses. I told him I'd ask around. Are you still doing illustrations?"

"Yes, why?"

"Well, I thought you might be interested in using Paul as a model. You know, like you used to?"

"I haven't done figure drawing in years."

"Well, no time like the present. You can't do still lifes forever."

"I have an art studio over my garage," she explained to Paul. "Although now it's more of a storage room."

There was an awkward pause. Paul broke the silence.

"Well, if you ever need it, I'd be happy to pose for you. If you don't mind an amateur, that is. I've never done it before."

She looked at him, her eyes softening.

"I think you might be very good at it," she said. "Let me think about it. I know where to find you."

She gave them a wry smile. and then turned and headed back to her place.

"Oh by the way, when you're ready to clean up, you're welcome to use my outdoor shower. Just help yourself."

"Thanks, Allyson. Appreciate it. Nice meeting you."

"Nice to meet you too, Paul. See you later, Maddie."

"Bye, Allyson."

As she walked away, Maddie turned to Paul and gave him a little shrug.

Later that afternoon, after the garden was tended too and the yard waste bin was filled to the brim, Paul decided to take Allyson up on the outdoor shower.

Maddie only had a bath at her place. And, as much as he liked a good soak now and then, he was more of a shower guy.

Maddie and Allyson were such good, longtime friends that there wasn't even a fence separating their lots. Their cottages had been built at the same time and were some twenty feet apart.

He just slipped between the bushes and he was in Allyson's backyard.

Her outdoor shower was typical of the ones you see all over Pleasure Point. Primitive. Open air. Covered in ivy. There was no door, just an opening facing her backyard.

He was wearing his bathing suit, t-shirt, and flip-flops.

He looked at the back of the cottage and didn't see Allyson anywhere.

He took off his shirt and kicked off his sandals. He turned on the water and began rinsing himself off.

He heard a door close and soon there was Allyson, standing with her hands on her hips, facing him.

"Feel free to use the soap and shampoo," she said. "No towel?"

"I forgot to bring one."

"No worries. I'll supply the towel."

She turned on her heels, went into the cottage and returned with a fresh, folded towel.

She placed it on a chair next to the shower.

"When you're done with it, just leave it on the chair. I'll bring you a fresh one tomorrow."

"Thanks. You don't have to do that though. I can drip dry."

"Don't be silly. It's not a problem."

He was letting the warm water rinse the shampoo out of his hair and off his muscular physique.

She seemed to linger for a moment. Was she checking him out?

He wasn't sure but he had a sense of her eyes on this body. He was wearing a bathing suit so it was no big deal if she was.

By the time, he opened his eyes, she had gone back into the house.

The following day, and each day thereafter, Allyson made it a point of bringing him a fresh towel whenever she heard him showering outside.

She'd say hi, ask how he was doing, chat for a while, and then leave the towel on the chair and go back in the house.

After a week or so, their chats got more involved and she ended up sitting in the chair while he showered with the towel on her lap. She'd sit there, chatting away, and just watch him. As he lathered his body and rinsed off with the warm, velvety water.

And when he was done and turned off the water, she'd stand up, go to him, and help him dry off. She'd carefully rub his back and legs, his chest and arms. Then, she'd turn around and go back in the cottage.

When Paul told Maddie about it later, she asked him if he thought Allyson was interested in pursuing a physical relationship.

Paul said he honestly didn't know.

"She seems more like a lurker," Paul answered. "She may be interested, but it seems like something's holding her back."

"Maybe she just needs a little push."

Paul was happy to help Allyson in any way he could. He'd grown fond of her. And she seemed to enjoy his company too. If he could help her spread her wings a little bit, what was wrong with that?

He was happy to oblige.

The truth was, Paul enjoyed spending time with her. Talking to her and getting to know her. She was an interesting person. Creative. Smart. Funny. He liked her a lot.

And, to be perfectly honest, having her stare at his near-naked body while he showered was kind of a turn on.

Over time, he found himself fantasizing about being with her. What if he decided to forego the trunks one day and shower naked. Maybe she'd slip into shower with him. They could make love under the streaming warm water.

But Paul was also aware that doing anything too in your face might backfire. The thought of inadvertently offending her, or worse, messing things up between her and Maddie, made him think twice.

But what if he did something seemingly innocent that raised the temperature a bit?

He always wore his boardshorts in the shower. Hell, he practically lived in them. They were big and baggy and didn't show a lot.

What if?

The next afternoon, approaching dinnertime, he went over to Allyson's for his daily shower.

He turned on the water, knowing she would be out shortly with his towel.

Then, he pulled off his shorts revealing a skimpy pair of Speedo-style swim briefs. They were left over from when he swam for his high school swim team.

A minute later, Allyson walked out carrying his towel. She sat in the chair.

Then, her jaw fell open.

Paul was wearing the skimpiest, tightest-fitting pair of nylon shorts imaginable.

The nylon fabric hugged his cock and balls. The micro-elastic was like a second skin around his luscious butt.

Paul kept showering away, feigning ignorance. He slowly turned in a circle to soak his hair.

He got a glimpse of Allyson staring at his crotch.

His suit, now soaking wet, was absolutely clinging to him.

Seeing her reaction made his heart pound. He felt the blood rushing straight to his cock. He was getting harder by the second.

"What are you wearing?" she gulped.

"Huh? Oh these. They're from my swim team. I was doing laps and thought I'd wear 'em."

"They look ... amazing on you," she gasped.

"You think? I've grown since I wore them last. They feel like they're too small for me."

He turned his back to her, and bent over.

"Like right here. They show a lot of my butt."

He heard her gasp. He turned to face her.

"And right here, in front, they feel really tight."

Sure enough, his package looked huge as his cock pressed against the fabric.

He cupped his cock and balls in his hand.

"I think maybe I've outgrown 'em."

She gasped again.

"I think they make you look fantastic," she said breathily. "Maybe you can't wear them in public. But you can wear them here. Anytime."

She was practically breathless.

"You think so? They just ... they don't leave much to the imagination, do they? I mean, look. When they get wet, you can see everything. Look close. Like, right here."

He turned off the water and stepped out of the shower. He moved next to her and pointed to the outline of his hardening cock. It was pressing against the fabric.

"They do show an awful lot, that's true. But that's not necessarily a bad thing."

"I don't know," he said. "I feel like I'm too big for them. What do you think?"

He slowly turned in a circle, giving her a good long look.

"Am I too big for them?"

"Oh, Paul," she gasped. You are big. No doubt about that. You're very big."

He slipped his hand under the waistband and adjusted his cock so it was laying to the side. It stretched all the way to his hip.

"I mean, how am I supposed to wear this? It's crazy."

She was mouth-breathing now, her body trembling.

"Um..." Paul said, don't you want to ... help dry me off?"

"Oh, yes. Yes, of course."

Not surprisingly, later that night, Maddie had some news for Paul.

"I just heard from Allyson. She says she wants to hire you as a model."

"No kidding?"

"She's willing to pay $50 an hour. That's a good rate, apparently. She seems excited about it."

"Cool. When does she want me to start?"

"As soon as possible. After you're finished working tomorrow afternoon. She said you could shower at her place."

Paul stifled a laugh.

"What's so funny?"

"No, I was just thinking," Paul said. "At least the commute's not bad."

"Thank you for doing this, Paul. This could be really good for her."

At 4:30 the next day, Paul walked over to Allyson's cottage, took off his clothes, and stepped into the outdoor shower.

He was wearing his Speedo.

A few moments later, Allyson arrived carrying a folded towel. She was in a blouse rather than her usual flannel shirt, and had a handsome scarf wrapped around her updo.

Under her eyeglasses, Paul noticed she was wearing eye makeup she didn't normally wear.

"Hi Paul, thanks for coming. I've decided to give myself a kick in the ass and start working with human beings again."

Paul gave her a friendly smile.

"Glad I could be part of your ... ass kicking."

She smiled.

"Here's your towel. I'm going to go get the studio ready. When you're done, join me there."

"OK, cool." Paul said. "One question. Um, do you want me to get dressed in these clothes again, or..."

"No, just wrap yourself in the towel. No suit. That's normal for modeling. Are you okay with that?"

"Absolutely. I just wasn't sure what you wanted."

"OK," she smiled. "See you in a few minutes."

She seemed happy and high energy, Paul thought. Maybe he could be part of a positive turn in her life.

After showering, he slipped out of his Speedo, dried himself off, and wrapped the towel around his waist. Then, he climbed the exterior staircase to her studio.

As he opened the door, he could see the ocean sparkling in the afternoon sunlight through a large picture window. Allyson was moving some boxes around.

In the middle of the room, an easy chair sat facing the window. A tripod with a still camera was pointed at it.

"Oh hi, come on in. I'm just getting ready. Just have a seat. We'll chat a little bit before we get started."

Paul looked around and sat in the easy chair.

She approached him a moment later.

"OK. Are you ready to try a little modeling?"

"Sure. Just tell me what you want me to do."

"OK, let me tell you a little bit about my process. Today is all about inspiration. I use this first session to improvise, take a few photos, try out different ideas. From there, I'll hopefully land on a direction, a theme, that I'll start to execute over the next few weeks. Think of this room as our little playground. Make sense?"

"Yeah. Sounds good."

"Great. So, let's get started. I thought it'd be good to begin with a little warmup. Just to loosen up. Get relaxed. Why don't you stand up and we'll just shake out our limbs a little bit."

He got out of the easy chair and faced her. He was till wearing the towel around his waist. She started shaking her arms. He mimicked her.

"That's it. Your legs too. Get your body nice and relaxed."

He copied her, swaying side to side, shaking his legs out, the towel still clinging to his waist.

"Now, you said you were a swimmer in high school. Maybe try some of the stretches you used to warm up for swimming."

He started by reaching his arms high into the air. On his tiptoes. Then he began windmilling his long arms, one at a time, stretching out his shoulders. He crossed one arm over his chest, stretching it. Then did the same with the other.

Then he raised one elbow above his head, reaching his hand down the center of his back. Then, he did the same with the other arm.

"Good. Now let's loosen up your lower body too. Stretch your legs. Your hips."

He lifted his knee to his torso and squeezed it with his arms. First one, then the other. He began rotating his pelvis, swinging his hips.

"Good. Now, I want you to close your eyes. And I want you to twist your body from side to side. Slowly. That's it. Now, swing your arms. Let 'em go."

He eyes were closed and he was twisting his body back and forth, his long arms wrapping around his body.

"That's it. Just relax. Let it flow."

His arms were flopping now, relaxed.

"Good. Now, slow it down. That's it. See how slow you can do it. Like you're in a dream."

He was moving in slow motion now, slowly rocking his head from side to side. He could hear her taking the camera off the tripod.

"That's good. Now, I want you to do that stretch with your arms again. Keep your eyes closed."

He could hear her snapping off a few pictures.

"That looks great. Now reach your elbows above your head. Nice. Keep doing that."

He heard the camera shutter. Click. Click. Click.

"Now both elbows at the same time. That's it."

She was snapping photo after photo now.

"Now, a full body stretch. Like you're just waking up."

He raised both arms above his head. His eyes still closed.

"OK, now do that stretch with both your elbows above your head. This time, clench your fists. That's it. Really flex those muscles. Fabulous. Now add in the lower body. Move your hips slowly."

He was moving in slow motion, his arms flexed. He looked like a Greek statue.

"That looks really good, Paul. Now, try rocking your pelvis. That's it. Good. A little slower."

He was undulating his body now. With his eyes closed. The camera kept clicking.