Pleasure's Look

Welcome to another entry in my series about our senses. Through this series I'm exploring how what we smell, taste, touch, see, and hear can inform and even enhance our sex lives.

This story is about the erotic trigger of sight, exploring how different people have things they enjoy watching or seeing during a sexual encounter.

In this particular story an older woman who enjoys being watched spends time with a young man, who is just beginning to understand the connection between pleasure and the erotic sight of another person enjoying that pleasure.

This of course is a very narrow glimpse into what people enjoy looking at. We all have specific things we like to see. After the story please leave a comment so we can all read what YOUR favorite erotic sight is (but keep your answer within Literotica guidelines please).

The stories in this series are grouped around the theme of our senses, but they're not connected to each other, so read them in whatever order you like. They'll all start with the word Pleasure.

If you crave more kink and depravity than is offered here, please check out my other submissions, but pay attention to category and story descriptions.

As with everything I write this story takes place in a happy alternate reality where birth control and STDs are not a concern.

Thanks for reading!

IsabellaEmily

~~

"Who's that?" asked Barry, struggling with his end of the twenty-year-old couch they were lugging up the stairs.

"Who are you talking about?" asked Chris, turning his head.

"That lady going in the front door," said Barry. "I thought you rented this place from Gary."

"I did," said Chris. "But he mentioned that his sister would be staying here this summer while he was in New York. That's probably her."

"Look at you," laughed Barry. "Sharing a house with an older woman."

"I'm renting an apartment," laughed Christopher. "There won't be sharing of anything. Besides she looks a little old for my taste."

They got the couch into the small apartment and pushed it against the wall.

"Old my ass," grinned Barry, continuing the conversation. "You're so desperate to get laid that you have no taste."

"I am desperate," conceded Chris. "But that doesn't mean I'm blind."

"Keep being so damn picky and you'll die a virgin," teased Barry. "One more trip and we're done, so let's get this fucking truck unloaded so I can get out of here."

"I'm not technically a virgin," Chris reminded his older brother, as he followed him back downstairs to the rented truck. "Or did you forget all about my hookup with Betty?"

"I can't forget something you remind me about three times a week," said Barry. "The first and only time you saw a naked woman. Too bad she got back together with her boyfriend."

"It still counts," Chris claimed. "Even if it didn't last long."

"Maybe if it lasted a little longer, she'd still be around," Barry said with a grin. "Now help me with this fucking thing."

He grabbed one end of the coffee table and Chris got the other, and in a few minutes, they were setting it in front of the couch.

"That's all of it," said Barry, looking around. "Except for the unpacking, and you are on your own for that shit. I'm going to return the truck and I'll see you Monday night."

"I appreciate it man," said Chris. "I owe you big time."

"You sure do," grinned Barry. "And you should start saving up for when I come to collect."

They walked down to the rented truck and Chris grabbed the remains of their fast-food lunch out of the cab while Barry closed the back of the truck. He was dropping it in the trash can at the bottom of the stairs as Barry started the truck and pulled to the end of the driveway.

He watched as Barry turned onto the street, and with a final wave he headed up the stairs, dreading the fact that he was going to spend the rest of the weekend unpacking.

It was his first post-college apartment, and the first chance he had to live completely alone. It was just a two-room apartment over a garage, with a tiny kitchen in one corner of the living room, a tiny bedroom, and a closet that had been remodeled into a bathroom.

But it was inexpensive. And most important, it was all his and he could do as he pleased in it.

His landlord was an old friend of his dad's, who traveled a lot since retirement, so there wouldn't even be someone watching him come and go.

As he climbed the outdoor staircase to his door, he heard someone call out.

"Hello?" said a feminine voice.

"Hello?" he answered, turning around, and looking toward the house.

Walking across the back yard towards the garage was the woman he and his brother had seen a few minutes earlier. As she got closer Chris realized that she was even older than he'd first guessed, but he decided that she wore her age well.

She was in her mid-fifties he'd guess, with streaks of gray showing through her dark blonde hair. She was wearing a shapeless yellow dress that fell almost all the way to her ankles and was barefoot.

"Hi," she said cheerfully. "I'm Stephanie. You just moved in today, right?"

"I sure did," he said, coming down the stairs to shake her hand. "I'm Chris. You must be Gary's sister."

"I am," she said. "I'm looking after the place for the summer. It's nice to meet you, Christopher."

"It's nice to meet you too," said Christ.

"All settled in?" she asked.

"Everything I own is in," he said with grin. "Virtually nothing is unpacked yet."

As they talked Chris had become aware that she wasn't wearing a bra. He tried not to stare but couldn't help but notice that the dark outline of her areolas were faintly visible through the yellow dress. He also realized that she had beautiful eyes and a friendly smile.

"I know how that goes," she said. "Moving sucks. What are you doing for dinner? Have you done any shopping yet?"

"Not yet," he said. "Unless you count beer and potato chips as a suitable meal."

"Guess that depends on how hungry you are," she laughed. "I'm headed out to pick up a pizza. You're welcome to join me when I get back, if you're willing to share a beer."

"That's a deal," he said. "I appreciate that. It will give me just enough time to get cleaned up."

"Great," she said. "I'll honk the horn when I'm back. Come on over."

She turned and made her way back across the yard and he took just a moment to watch her walk away.

Even though she was probably three decades older than he was he couldn't help but wonder about her body. Even under the shapeless and flowing dress, she looked to have an amazing ass that went well with her large breasts.

He climbed back up the steps to his apartment, grinning to himself.

"Calm down dude," he thought with a grin. "She's a hippie who's older than your mom."

She seemed nice enough though, and he really did appreciate the dinner invitation. After a day spent moving, hot pizza and cold beer sounded perfect.

Even though he doubted he'd have anything in common with Stephanie, it felt nice to know a neighbor already, even if she was a temporary one.

The reality was that even though Chris joked about sex constantly, he was relatively inexperienced when it came to women.

He'd had exactly two steady girlfriends in his life but had never gotten further with either one than intense make out sessions, accompanied by some exploratory fingering and handjobs.

His ill-fated hookup with Betty had ended as quickly as it started. He'd been too aroused to last long, and she was so focused on missing the guy she'd recently broke up with that she'd hardly noticed that he was there.

He made sure he still had some ice in his cooler and pulled his five remaining cans of beer out of the fridge and put them into the icy water. He added a few cans of coke, mainly because he didn't want Stephanie to get the impression that was some sort of hard partying frat boy.

"Fuck me," he laughed to himself. "I know I'm horny. But am I so desperate that I'm worried about impressing that old hippie?"

He made sure he had a clean towel and then took a quick shower, realizing too late that the only soap in the bathroom was a bar of hand soap he'd put by the sink early that morning.

"Beggars can't be choosers," he thought, lathering up. "At least I won't stink."

After his shower he found his clean clothes and quickly dressed, throwing the dirty clothes into the corner of the room. He had enough clean clothes for work on Monday, but he'd have to figure out where the closest laundry-mat was before too many more days had gone by.

Just as he was looking for his deodorant, he heard a quick honk from a car horn.

"Screw it," he said. "It's not like she's going to sniff me."

He grabbed the cooler and made sure he had his keys, and then stepped out onto the landing and locked his door.

He headed towards the house and found that the backdoor next to the driveway was open a crack.

"Hello?" he called out, knocking as pushed it open.

"Come on in Christopher," Stephanie called. "I'm in the living room."

He went through the kitchen and found her in the front room of the house, putting a roll of paper towels and some paper plates on a coffee table that sat between the couch and a large television.

"I was planning to eat in front of the TV," she said. "I hope that's okay."

The tv was playing already, showing the beginning of an old Star Trek movie.

"It's where I usually eat," he admitted with a grin.

He sat on the couch and accepted a plate from her, before lifting the lid of the cooler.

"Help yourself," he said, grabbing a can of beer.

Stephanie took a beer and put the pizza box on the coffee table. She picked up the remote and turned the tv volume down.

"Hope you don't mind sci-fi," she said. "I'm a definite nerd."

"I love it," he said. "This movie is one of my favorites. Not the best Star Trek movie, but it's one of my favorites."

"Oh yeah?" she asked, holding the open pizza box out towards him. "Which one is your favorite?"

For the next hour they ate pizza and watched the movie, chatting about the franchise and drinking beer while getting to know each other.

Chris was stunned to realize that he was having a better time than he had in months. And that included the last three dates he'd had.

"So you're single huh?" Stephanie asked him, picking up an earlier conversation about their social lives.

"Yeah," he said. "Mostly I don't mind. I just got done with school and started a new job, so I need to spend time figuring that out. It's easier not having to tend to a relationship. I just miss...well...you know."

He was suddenly embarrassed, and he wasn't sure why. He talked and joked about sex all the time, but for some reason mentioning it in front of Stephanie seemed weird.

"You miss fucking?" she grinned at him.

"Something like that," he laughed. "How about you? Are you single?"

"I am," she said. "I was married once years ago, and I can definitely relate to missing sex."

"Oh," Chris said stupidly, unsure how to respond.

"When my marriage ended, I almost couldn't remember what a cock looked like," she laughed. "Hell, the first time after my marriage that I went down on a guy it was like tasting cum for the very first time."

Chris had no idea what to say, and he was sure that everything he could think of would make him sound lame and stupid.

Stephanie laughed.

"Too much information?" she asked with a grin.

"Uh no," he stammered. "I was just, you know, making an effort....to uh..."

"Relax Christopher," she laughed. "I'm not trying to flirt with you. I just have a healthy sex drive and I like to talk about sex. I hope that doesn't offend you."

"Oh, I'm not offended," he grinned. "I just didn't want to say the wrong thing and end up sounding like an asshole."

"You don't have to worry about that with me," she said. "I'm almost impossible to offend, so you can't really hurt my feelings. Are you willing to talk about sex with a lady my age?"

"Absolutely," he answered. "Sex is one of my favorite topics. How long ago was your divorce? If you don't mind a nosy question."

"There's one thing you should know about me Christopher," she said. "And that's the fact that sexually nosy questions and answers are my second favorite way to spend time with someone."

"It's a good thing we're going to be neighbors," he laughed. "I'm the same way."

"Good!" she exclaimed. "I've been divorced for ten years. We got married right after high school. He was a nice guy, but I spent way too many years trying to be someone I wasn't in order to make it work. Once I gave up, we both ended up a lot happier. We get along much better since the divorce."

"Sometimes it's like that," said Chris, not that he had any experience when it came to staying in touch with exes. "I'm sorry it didn't work out though."

"Don't be," she said. "He settled down with a widow friend of ours and has the boring once-a-month-in-the-missionary-position sex life that he's always wanted."

"What about you?" Chris asked. "Did you get what you wanted?"

"Not every night," she grinned with a wink. "But when I do get it, I enjoy it to the full. I'm not only working to keep satisfied now, but I'm making up for lost time."

"Sounds like the best way to live life," he laughed.

"Tell me about your sex life," she asked, leaning back and crossing her legs. "Are you staying satisfied?"

He stared for just a moment, acutely aware as the dress stretched around her hip and thigh that she didn't appear to be wearing any underwear.

"You mean like...dating?" he asked.

He still wasn't sure what might offend her, nor did he want her to think of him as some sort of inexperienced wimp.

"I mostly mean orgasms," she said. "However they happen for you. Fucking, or being fucked, or blowjobs or masturbation. What sort of orgasmic pleasure are you experiencing Christopher?"

"Well at the moment there's not much of anything," he admitted, feeling pathetic.

He was a twenty-two-year-old college graduate, with a decent job and his first apartment, and his social life should be the sort of thing he'd always dreamt about.

And here he was talking with a lady three decades older than him who not only had more sexual experience than him but was probably having more sex than he was.

"Not even masturbation?" Stephanie asked. "Surely you do that for yourself don't you?"

"Well sure," he stammered. "I mean, I guess everyone does that sometimes."

"You're goddam right they do," Stephanie said. "After the first few years of my marriage almost every orgasm I had was one I made myself have. Even now I do it almost every night unless I have help. Or an opportunity to help someone else."

"I was just a little embarrassed," he said. "I wasn't sure I should admit it. But it's not something I just do sometimes. I'm an every night guy myself."

"Oh good," she said with a wide smile. "I'd hate to have someone boring for a neighbor."

"If you consider masturbation something that keeps someone from being boring, I'm the least boring guy you've ever met," he laughed.

"So what do you think about when you cum?" she asked.

"I...what?!" he stuttered.

"When you're stroking your cock," she said. "When you're about fifteen seconds away from losing control, what is it that you most want to have someone do with your cum?"

He squirmed on the couch, hesitant to say something that might be too weird, but not wanting to be anything less than completely honest either.

"Do you really want to know?" he asked instead of answering.

"I do," she said. "I'm probably going to masturbate myself to sleep tonight, and I'm always looking for some inspiration."

"Inspiration?" he asked.

"Sure," she said. "It's always hot to know that someone is getting off to the same thing that you are. Especially if they're getting off at the same time you are. Are you going to masturbate tonight, Christopher?"

"Well I don't have a schedule or a plan or anything," he said. "But I'm sure something will come up."

"So when you're stroking yourself tonight what will you use?" she asked. "Lube? Lotion? Spit?"

"Lotion I guess," he said. "If I have some. I'm not really picky."

"You should be," she said. "If you want a woman to worship your cock, you need to treat it like its worthy of being worshipped. Your pleasure is worth more than dollar store lotion, isn't it?"

Without waiting for an answer she got up and went down the hall, returning in just a moment with a tiny bottle.

"I use this," she said. "It's called Pleasure's Touch and it makes everything so slippery and warm."

"I'll have to get some," he stammered.

He was rock hard, and she hadn't been out of the room long enough for him to readjust himself. The sudden mental image of her fingers sliding back and forth through her slippery hole wasn't helping his predicament either, and he felt himself throb against the inside of his boxers.

He couldn't believe he was having such a sexual conversation with a woman he'd just met.

He also couldn't believe the sexual hunger he was feeling for someone who was way too old for him. But her openness and honesty were certainly attractive, and her stiff nipples indenting the fabric of her dress were also very much on his radar.

"You already have some," she winked. "Take and use this bottle. It's my gift to you. And to your cock. Use it knowing that I'll be using the same kind over here to get myself off."

She held it out and he took it from her, his mind racing as he turned the bottle to pretend to read the back in an attempt to organize his thoughts.

"Where do you cum Christopher?" she asked, pushing the conversation forward.

"Um...." His face flushed as he grinned. "Do you mean how do I....?"

"That's exactly what I mean," she laughed. "Do you cum into a towel? Tissues? Toilet paper? Or are you one of those gross guys who cums on his sheets and then sleeps in them?"

"I use a towel to clean up," he said. "And to catch it, unless I'm on my back."

"I love to see a guy spurt his cum all over his belly," she said. "I need something else to drink. Want a bottle of water?"

"Yeah," he said. "That sounds good."

He wondered how she could switch from talking about guys cumming on themselves to getting something to drink so casually.

When she was in the kitchen, he pushed his cock down and repositioned it in his pants, hoping to eliminate the obvious bulge of his arousal.

She returned with the water and handed one of the bottles to him as she sat down.

"I guess I've been asking more than I've been sharing," she said. "Would you like to know about what I do? Or is that too much for you?"

"I'd like to know," he grinned.

And to his surprise he really did want to know. His erection hadn't diminished a bit, and he was more than a little curious about her sexual habits.

"I take masturbation pretty seriously," she said. "I light candles, turn off the phone, play some music, and sometimes even dress up to make myself feel sexy or kinky."

"A connoisseur," he said.

"It's like I was saying before," she said. "I want my body to be worshipped, so I worship it."

"I guess I've always considered masturbation to be a substitute for sex," he admitted. "I should probably think about it the way you do."

"Oh fuck yes," she said. "It's not a substitute. It's a glorious amount of pleasure. Just instead of sharing it with someone, you're doing it alone. But it can be just as intense."

"So candles and soft music?" he prompted her.

"Not always," she said. "Sometimes I use a detachable showerhead for a quickie. When I lived in the garage apartment, I came in that shower almost as many times as I came on my bed."

"Now I'll be distracted during my next shower," he laughed.

"Good," she said. "I like inspiring distraction Christopher."

"I guess you don't need a towel or anything," he said, remembering her questions to him, and assuming they wouldn't be too personal.