Pleasure's Look

"I usually make myself cum with one nearby though," she said. "I'm not really a squirter, but if I get wet enough, I can drip on the sheets, and I hate to get out of bed afterwards."

"That's fucking hot," he said softly. "That might be the hottest fucking thing I've ever heard a woman say."

"It's also true," she said quietly, leaning forward. "Anytime you and I talk about sex together, I will always be honest with you."

"Are you wet right now?" he blurted out.

"Deliciously so," she smiled, shifting the way she was sitting on the couch. "Your body isn't the only one responding to our conversation."

She pointedly looked down at the front of his pants, and he did too.

"That obvious huh?" he asked. "I'm sorry."

"Don't be sorry," she said. "Arousal is natural and beautiful. And I'm flattered that a guy your age is willing to get so hard in the same room as me."

She picked up her water bottle and took a drink, before setting it aside and looking him in the eyes.

"How old are you anyway Christopher?" she asked.

"I'm twenty-three," he said. "How about you?"

"I'll be fifty-nine next week," she answered. "Is it weird for you to be sitting here with an old lady?"

"A few hours ago I would have thought so," he admitted. "I wouldn't have thought we'd have anything in common. But now I can't think of a time that I've enjoyed a conversation more."

"I'm glad," she said. "I was just inviting you over for dinner. I didn't plan to take things in this direction. But it certainly has worked out pleasantly."

"I think so too," he grinned.

She picked up the remote and turned the tv off, and the room was left with only the tiny lamp in the corner of the room for light.

"What do you think about when you cum?" she asked him.

"Lots of things," he said. "It depends on my mood and what I'm watching."

"At the moment of orgasm," she said. "That delicious moment where control is gone but the orgasm hasn't started yet. What jumps into your mind at that moment?"

"My fantasy in that moment is that she wants my cum," he said. "Whoever I'm fantasizing about, she wants me to cum, on her or in her, so she can see it or taste it or feel it."

"Do you like the idea of her tasting it or being covered in it?" Stephanie asked. "Do you want her to accept your hot sperm because she wants to please you, or because she craves hot cum?"

"Both," he grinned. "Hopefully, she likes me, but I don't think I'd enjoy it as much if she was just doing it to be nice. I want her to really want it. Especially if I can watch her enjoy it."

"Watch her enjoy it?" she asked, leaning forward.

"Maybe that's a guy thing," Chris said. "Wanting to watch his partner take his cum all over her body or up inside her."

"I think guys are often more visual," Stephanie said. "But I totally understand what you mean. That's what usually triggers my orgasm. I love being watched. I really fucking love it. My best orgasms come from masturbating while someone watches. Or while I fantasize about someone watching."

They sat quietly for a moment, Christopher wondering how she'd react if he volunteered to watch her make herself cum, and Stephanie wondering if there was any way this young man would entertain the idea of letting her get herself off in front of him.

After a long pause, Stephanie finally broke the silence.

"What are you thinking about?" she asked quietly.

"I'm trying to decide what to say next," he said. "I've never enjoyed talking to someone like this, about this stuff, and I don't want to stop, but I don't want to stay too long and have you get tired of me. I don't want you to think of me as an inexperienced kid."

"I never get tired of talking about pleasure Christopher," she said. "And you may be a bit inexperienced, but you seem like a hell of a man to me."

"And you're one hell of a lady," he said, meeting her eyes in the dim light.

"Are you still hard?" she asked him.

"Not as much as I was a little while ago," he said.

"Are you still aroused though?" she asked.

"Oh, hell yes," he grinned. "A breeze would get me hard again."

"Would it be strange if I asked you to show me?" she whispered.

"If you want to see," he said.

She nodded her head, and he glanced around the room as if to confirm that they were alone.

He then leaned back on the couch and unsnapped his pants, and then tugged down the zipper and pulled his underwear down as he opened the front of his pants.

His cock was semi-erect and in the soft light she thought it looked nearly perfect. The head looked darker than the rest, and he had a nice fuzz of pubic hair, without it looking like an untamed jungle.

"I love it," she whispered. "It's nearly perfect."

"Nearly?" he asked, genuinely curious about what she meant.

"I'll bet it looks perfect when it's hard," she smiled.

"It wouldn't take much," he said.

As he spoke the cock appeared to twitch, and as she stared it slowly grew longer and thicker as blood pumped into it, his physical arousal matching the lustful need in his heart.

She leaned forward and stared as he got harder and harder. And her intense gaze just turned him on even more, and without being touched his erection grew into a throbbing extension of his lust, his veins easily visible on the tight skin as his cock stood straight up.

"Wow," she laughed. "You weren't kidding about it not taking much. You better be careful walking through the yard. I can't imagine what a real breeze would do to it."

He grabbed his cock and she thought he was about to stroke it for her, but she realized he was pushing it into his pants.

"Thank you," she said. "I love to see a nice stiff prick on someone I know."

"You're welcome," he laughed. "It's fun to show it to someone who wants to see it."

"If you ever have any interest in seeing me, just let me know," she said. "I don't want to just flash you, but I like showing off."

"I will happily look at anything you want to show me," he said softly, his heart pounding.

"They don't look the same as they did forty years ago," she said.

"Beauty has more to do with the soul than the physical body," Chris said. "Except that sounds like the pretentious stuff philosophy majors say to get laid."

"It is sort of a cliché," she admitted with a laugh. "But I think there's plenty of truth to it."

She reached up and undid the first three buttons on her dress, staring at his face while she did it. He wasn't looking at her in a lecherous way. He genuinely seemed to be interested in her body.

She pulled one of her breasts out, before pulling the front of the dress to the other side to pull the second one out. She sat back with her breasts sticking out the front of her dress, her nipples stiffened points in the center of her large areolas.

"Beautiful," Chris whispered. "They're so amazing."

"A lot less perky than they once were," Stephanie said. "But even at my age I have no real complaints."

"Neither do I," he grinned. "I've never seen a pair so perfect. I could stare for hours."

"I won't last that long," she said. "Not with you staring at me like that. I'm dripping like crazy."

"That's so sexy," he said.

"So what should we do now?" she asked with a wink, making no move to cover herself.

She knew she was putting him on the spot, but she also knew that with their age difference she should give him as many chances to back away as she could.

"Before the night is over, I need to go somewhere and do what we've been talking about," he said. "My balls actually ache from this conversation. Especially now."

"I'll take that as a compliment," she said. "But I know what you mean. I'm in need of some attention myself."

He looked like he was about to say something, but he didn't. She noticed that he was staring at her breasts with a look of total lust, and even when he became aware that she saw him staring he kept looking.

She shifted her hips on the couch happily, feeling warmth spread through her belly. Even if he wanted to back away, the orgasm she was soon going to make herself have would be an incredible one.

"We have two options I think," she said. "We just have to choose one."

"Okay," he said, looking up at her.

"We can go our separate ways and make ourselves cum," she said. "I think a good throbbing orgasm is what both of us need and want right now."

"I can't argue with that," he said.

"Before I tell you what I think the next option is, I need to ask you a question," she said.

"Go for it," he said.

"Do you find me arousing?" she asked. "I'm not asking if you find me attractive. I'm nowhere near as pretty or sexy as I used to be. But given the reality of our age difference, and knowing what we now know about each other, are you aroused by me?"

"I think you're beautiful Stephanie," he said. "I think everything about tonight and our conversation has been arousing and beautiful. I find you very arousing."

"How arousing?" she asked softly.

He stood up then, in the soft light of the room the bulge in the front of his pants was plainly obvious. She wondered if it hurt his cock to be that hard.

"Would you like to watch me make myself cum?" she asked. "I get off on being watched, but only if the person watching wants to watch."

"I would love that," he whispered.

"Come along," she said.

She stood up and led the way down the hall, her breasts still hanging out of her dress.

He followed her to what was obviously a guest room, plainly decorated with a wide double bed, an easy chair in the corner, and a long dresser.

She turned on a lamp on either side of the bed, and turned to face him.

He stood facing her at the foot of the bed, and she pulled the sundress up over her head and dropped it to the floor.

"Wow," he said again, staring at her totally naked body.

"Not too bad for an old lady am I?" she asked with a grin, her eyes firmly glued to the front of his pants and the obvious erection straining to get out.

"You can stand or sit," she said, pointing at the chair. "Whichever is most comfortable for you, and whatever allows you to see the best."

She sat on the bed and spread her legs, and he stared at the tiny tuft of pubic hair above her otherwise bare pussy.

"I'm going to make myself cum," she said. "If you need to take your cock out, please do. If you want to wait to masturbate till you get home you can, or you can do it here if you need to. But please let me cum first if you do it here. I very much enjoy watching a cock lose control of its hot load."

She reclined on the bed, reaching up to pull the pillows close to her to prop herself up a bit. With her legs spread and her feet on the floor, she watched him as he stood transfixed.

She gently cupped her breasts, sighing as a pleasing warmth moved through her body from her own touch.

"The hornier I am, the better my nipples feel when they're touched," she said softly, almost to herself.

After several minutes her hands moved slowly along her stomach, and she shuddered softly as her touch moved closer and closer to her wet center.

She used her fingers to spread apart her lips, and with one finger she touched her opening, concentrating on her slick lips as her breathing became heavier.

"Right here," she said, circling her finger around her clit. "That's where all the feeling is centered, and where all the pleasure starts for me."

She moved her fingers back to her hole, moving two fingers up and down and up and down, licking her lips and closing her eyes as she groaned softly.

After several minutes of slowly strumming her hole she moved her fingers back to her clitoris, touching it as she worked her slippery fluids over it.

"It feels so fucking good," she told him. "I've been so horny for the past hour. It took all my control not to pull up my dress and finger myself in the living room while we were talking."

"I would have loved that," he said. "I was so hard."

"Was?" she asked, looking down at the front of his pants.

Without a word he unzipped and unsnapped his pants, and within seconds was standing at the foot of the bed naked, his cock thickly erect and pointing straight out away from his body.

"You've got me so turned on," he said. "I can't stand it."

She moved her fingers faster over her clit, pushing the fingers from her other hand up into her as she looked hungrily at his stiff cock.

"I'm starting to feel really good," she grunted. "Seeing your hard cock makes my clit tingle so much."

He reached towards his cock and gave it a squeeze, before letting go of it so he could concentrate on watching her. Her eyes were glued to his erection, and her stare made his balls ache.

"I'm getting close," she said. "It's going to happen soon."

"Can I look closer?" he asked, his eyes moving over her body.

"Yes, yes!" she squealed. "Watch me!"

He knelt on the floor between her legs, his face inches away from her soft thighs. She sat up, furiously rubbing herself while looking down at him, his attention making her even wetter.

"So fucking sexy," he said.

"Watch me cum!" she screamed, and suddenly began to convulse as her orgasm hit her.

Her fingers blurred over her clit as she fingered her hole, gasping and moaning as she twisted with pleasure.

He closed his eyes and inhaled, loving the scent of her arousal just inches from his face. No matter what else happened tonight, he'd remember this forever.

At last, she fell back on the bed, panting with her fingers still between her legs, her body sweaty from its recent exertion.

"Fuck I love to be watched," she said with a soft smile. "Thank you."

"Thank you," he grinned. "That was the best goddam thing I've ever seen."

He stood up then, and her eyes shifted to his still rock-hard cock.

"Does it hurt?" she asked, sitting up.

"No," he said. "It sort of aches, because it needs relief, but it's not painful or anything. Honestly waiting like this feels surprisingly good. It really builds the pressure up."

She looked at him with a twinkle in her eye.

"Where do you want to relieve it at?" she asked him. "In private? Or with an audience?"

"Do you want to watch me cum?" he whispered.

"Christopher, if you say the word, I won't just watch you cum, I'll make you cum," she said.

He hesitated for several seconds before speaking, staring down at the fifty-nine-year-old woman with gray streaks in her hair, her large breasts slightly sagging and her flat stomach and smooth thighs soft.

Six hours ago he would have scoffed at the idea of spending time socially with a woman that age. Now he was convinced that her age and appearance made her even more sexually attractive instead of less.

He reached out and gently touched her cheek. She reached up and cupped her hand over his.

"Please?" he asked softly.

"I haven't touched a twenty-three-year-old cock in years," she said with a grin. "I'm going to enjoy this."

She grabbed his hand and pulled him to the bed, and within seconds he was sitting where she had been, and she was kneeling on the floor between his legs.

She put her hands on his knees and moved closer to him, and he groaned as she stuck her tongue out and licked his balls. She lapped at him with her wet tongue gently at first, and then with more and more enthusiasm until she opened her mouth wide and took both of his balls into her mouth.

He groaned as she closed her mouth around his sensitive orbs, and when she started to suck while flicking her tongue against them, he nearly passed out from the intense sensation.

She looked up at him as he placed his hands on her head, gently holding her as she pulled on his balls with her hot mouth, his cock throbbing above her face as his whole body shuddered.

She pulled her mouth away, stretching his scrotum tight, and then opened her mouth slowly, until one by one his testicles popped out of her wet mouth.

"Fuck," he whispered.

She eyed his cock, as if hypnotized by the stiff and throbbing arousal that was moving gently in time with his thudding heart, just inches from her face.

She opened her mouth and moved forward, his cock disappearing into the wet suction of her mouth as she pushed her face down his shaft, until her lips reached the very base of him, staring up into his eyes the entire time.

He moved his hips up from the mattress, groaning deep in his chest as he watched her suck hard on his cock, her eyes bright with delight as he felt his cockhead massaged by the soft back of her throat.

He'd never felt a mouth on his cock before, and now this sexually ravenous woman was deepthroating him while looking up at him like this was the happiest she'd ever been. He bit the inside of his cheek and struggled to hold back the orgasmic pressure that had been mounting within him all night.

She slowly pulled her mouth off him, sucking hard as she drug her lips along every inch of his quivering shaft.

"Fucking delicious," she whispered, staring up at him and licking her lips. "I love your taste."

She kissed his cockhead, pulling his stiff meat closer to her with her fingers while she pressed her lips against him, flicking her tongue out before moving to a different spot and kissing him again.

Up and down his shaft she moved, glancing up at him while she kissed and licked at his cock, loving the way it throbbed and jumped in her hand.

"Oh gawd," he groaned softly, trying to decide if the pleasure he was feeling was equal to or better than the sight of her so obviously loving his cock against her face.

And then she took him in her mouth and sucked again, softly and slowly while he moved with her, loving the hot wetness of her mouth.

And then she sucked harder, cupping his balls with one hand and using her other to start to pull his shaft up and down.

He felt a familiar feeling deep in his balls, and he knew that he'd never be able to hold off his pleasure with her mouth and both hands on him.

She pushed her face down on him again, taking him all the way into her throat once more, and her tongue darted out and licked at his balls and he moaned loudly and grabbed her head.

"Fuuuuuuuuuuuck," he whispered, his voice desperate with need.

She took him out of her mouth and started to stroke him.

"I want to watch you cum," she whispered. "Do you want to cum all over my face?"

"If...if...if you want me to," he stammered, almost unable to comprehend what she was saying.

"Don't hold back," she begged him. "Just let it fly. Coat my face with it. Cum all over me. Cum on my body and in my hair. Cover me with your hot mess."

She pulled him into her mouth and sucked hard, stroking him furiously as his balls tightened up in her hand.

"I'm gonna cum," he groaned. "I'm gonna...it's gonna...gonna GO! NOW!"

Suddenly his entire body tensed up and his cock throbbed hard in her hand, and she stroked him faster and harder as she saw his cockhead spurt a rope of white cum up into the air.

It splashed onto her face, followed by another and another as she giggled with glee at the hot slippery mess on her skin, and she felt a bolt of it shoot across her forehead and into her hair.

She moved her head back and forth as she watched him cum, amazed at the amount of semen that thundered out of his cockhead as he throbbed and groaned.

While she watched him spurt he watched his cum coat every inch of her face, his thick globs of cum dripping everywhere on her as his balls emptied themselves in her tight stroking grip.

At last his spurts diminished, and she rubbed his cockhead through the pool of cum on her forehead, giggling softly with joy.

A spurt of cum had landed in one of her eyes, and she looked up at him, one eye squinting with the sting of salty cum, the other wide open. She smiled with strings of cum across her open mouth, her tongue darting out to lick and taste his sperm.

"Jeezus," he panted, collapsing back on the mattress.