Step by Step: Last Night of Summer

This short story is rather tame, but as much as I love masturbating with a partner it's near and dear to my heart.

I plan to use Katie and Tim and their relationship as an excuse for them to explore every aspect of sex as their relationship and this series progresses.

If you want to read something kinkier, please check out my other stories, and if you have suggestions for sexual activities Tim and Katie can try together leave me suggestions in the comments.

If you're a long-time reader, thank you for your patience during this extended sabbatical I'm taking. I'm working on several creative projects in my real life and my hobby writing is on the back burner for now.

IsabellaEmily

~~

"What does it feel like?" Katie whispered.

"Tight," Tim answered. "Like a clenched muscle. Tight with anticipation."

Tim and his stepsister were in his bed, with the only light in the dark room coming through the partially open closet door.

His dad and her mother had married two years earlier, and they'd each graduated high school a few months earlier. They'd always had a sarcastic and playful relationship with each other, which they each loved since they were both fairly shy and introverted at school.

In less than twelve hours they'd each be leaving in opposite directions for their freshmen year of college. After a summer of serious conversations and teasing flirtations and innuendo, Katie had finally shared with him a plan that had been brewing for weeks.

"Let's show each other what our orgasms are like," she said. "It'll be just like friends helping each other practice kissing or something. That way we'll each know what to expect."

That was what caused her to crawl out of her bedroom window at midnight and walk along the roof of their back porch to get to his room. She'd found him nervous, curious, and in his bed naked as they'd planned.

Katie sat on his bed facing him, taking her first good look at a real honest to goodness erect cock.

Tim was stretched out on his back with his hands behind his head. His blankets had been pushed aside, and his pajama bottoms were next to the bed. He was now completely naked, with his erect cock pointing straight up towards the ceiling while Katie stared at it.

"Does it feel good like that?" she whispered, leaning closer as she stared in fascination.

"Yeah," he answered. "If it stays hard for too long like this it will start to be uncomfortable, but that's just because it needs to be touched."

"Needs to be?" she asked, her eyes wide in the dim light.

"Well it doesn't need to be touched," he admitted. "But the purpose of getting hard is to feel pleasure, and that requires touching of some sort."

"How often does it get all hard like this?" she asked, moving her head to look at his cock from his point of view.

"It happens in my sleep every night," he said. "And whenever I think about sex. Or see someone that I think is sexy."

"Do you think about it a lot?" she asked.

"All the time," he grinned. "Don't you?"

"I guess," she blushed. "I think it's pretty normal to think about it."

"Yeah," he agreed. "It is normal to think about. And fun."

"What do you do when it's like this?" she asked.

"That depends on where I am," he answered her. "And how much time I have."

"Does it ever happen during the day?" she asked.

"All the time," he chuckled. "It happened at dinner tonight."

"It did?" Katie asked.

"Yeah," he answered. "You weren't wearing a bra and I could see your nipples through your shirt."

"Tim!" she whispered, smacking his arm and glancing towards the door to his bedroom as if she had suddenly been reminded that his dad and her mother were asleep downstairs.

"You said that we'd be honest together," he said, playfully rubbing his arm as if she'd hurt him. "Don't blame me for answering your question honestly."

"It looks a little smaller," she observed. "Still really hard and big, but like it's not as intense as it was a few minutes ago."

"That's because we're talking," he said. "If it gets left alone it will get soft after a while. Especially if I get distracted."

"Is that what happened at dinner?" she asked.

"Sure," he said. "I stopped thinking about your nipples and concentrated on eating and after a few minutes it went away."

"What if you're someplace where you can keep thinking about something that makes you hot?" she asked. "What if you're up here alone and you keep thinking about sex? It won't go away will it?"

"No, but if I'm thinking about sex I don't want it to go away," he told her.

"Does thinking about sex make it feel better?" she asked, moving again so she could look at it from the end of the bed.

"Oh hell yes," he said. "When I know I have time to take care of it everything I look at or think about makes it harder, and the harder it gets the better it feels."

"And then?" she whispered, looking into his eyes as she moved up next to him.

"And then what?" he asked, teasing her.

He knew that she knew the answer, but he wanted to hear her say the words as badly as she wanted to hear them from him.

"And then what do you do?" she asked.

"The better it feels the more I want to touch it," he said with a grin. "And the more I touch it the better it feels."

"How do you touch it?" she asked. "Like where do you do it? What do you do while you're doing it?"

"You sound like you're writing a book," he laughed. "Why do you want to know all this?"

"Because I don't know," she said. "I want to learn everything I can about how this all works. And right now, you're the only one I know that I can ask. Don't you want to know how it all works?"

"I do," he admitted. "But I always hoped to learn by doing. Or watching."

"We're not ready for that," she whispered. "At least not the doing part."

"Watching could be fun though," he said hopefully.

"I think so," she grinned. "Will you show me?"

"Show you what?" he teased.

"Show me how you touch it," she whispered, her eyes big as she watched him intently.

He didn't answer immediately, but she saw his cock throb without any other part of his body moving, and she knew he wanted to.

"I will," he said, trying to disguise his need. "But like we talked about this afternoon. I want to see you do it too."

She nodded and blushed, looking over her shoulder at the door.

Her own bedroom door was locked, and so was Tim's. She'd have to scramble back to her room across the porch roof if she heard her mother in the hallway. But her mother hadn't been up to her room in the middle of the night in years, and there was no reason to expect an interruption now.

"Do you want to go first?" she asked.

Not only was she anxious to see him touch himself, but they'd agreed that only one of them would undress at a time, and his bottoms were already off.

"Sure," he said with a grin. "If you really want to see me do it."

She nodded again, feeling suddenly hot and wondering if Tim could hear her heart pounding.

"You're not going to back out are you?" he asked.

"No," she said. "I won't. I've been needing to do it since we talked earlier."

"How do you want me to do it?" he asked softly.

"How?" she asked.

"So you can see best," he said. "That's why you're here, so we might as well do it so you can watch."

"Oh," she said. "I thought just like this maybe."

"Open the closet door all the way," he suggested. "That will give a little more light so you can see better."

She silently moved to the closet and slid one of the doors over, pleased at how much soft light fell across the bed.

She really did want to watch and was only a little embarrassed for her stepbrother to realize how badly. Little did she know that being watched while masturbating was a recurring fantasy of his.

She returned to the bed and perched next to Tim, fascinated that the still thick cock was drooping, the head pointing at the wall as if it was exhausted.

"It's getting soft," she giggled.

"It's distracted," he said with a grin. "He needs some inspiration."

Without a word she lifted the front of her tank top, and he gawked at her gorgeous breasts in the soft light, the pink areolas and stiff nipples making him lick his lips involuntarily. She didn't notice because her eyes were riveted to his cock, which had returned to being fully erect, straining towards the ceiling.

They stared at each other for several seconds, each of them oblivious to the gaze of the other as they memorized each other's nakedness.

She'd shown him her breasts before.

Once earlier in the summer when he'd sarcastically made a joke about peeking at her in the shower. She'd responded by lifting her shirt and bra and giving him a two second look at her breasts followed by her middle finger as they laughed.

Another time they'd been out at the pool and she'd been drying off, and she'd deliberately undid her top and stood in front of him topless, delighting in his wide eyed stare.

But this was different. Behind a locked door in the middle of the night, the two of them eager to push their sexual boundaries and explore together.

Katie glanced away from his stiff cock, making eye contact with him as she gave him a wordless but encouraging nod.

He looked back at her breasts as he took his cock in his hand and started to slowly slide it up and down.

He stared at her chest for several seconds, lost in the beauty of the moment. And then he looked at her face and saw the lustful way she was staring at what he was doing while holding her top up, and he gave an involuntary squeeze of his hand and a bubble of precum oozed out of his dickhole.

"Oh wow," she whispered, mesmerized by the clear fluid that was making his cockhead shiny.

"It feels good when the tip gets slippery," he told her. "It means my balls are starting to feel full and I need to cum."

"Is that how you do it?" she whispered, leaning closer. "Up and down like that?"

"Mostly," he said. "I go faster or slower, depending on how it feels and how quick I want to cum, or how much I want to let it build up."

"Build up?" she asked.

"The longer I do this, the more I'll cum and the better it will feel," he said.

"What do you normally do?" she asked.

"Most nights I do it quick if I'm really horny," he said, moving his hand a little quick to demonstrate. "I'll use lotion or something and make it go off as fast as I can. And then I go really slow for a long time until I cum again, letting the second one build and build."

"Just like this on your back?" she asked, moving over his legs so she could watch him stroke from the other side.

"Sometimes in my chair," he said. "If I'm watching something hot online."

"Do you ever do it standing up?" Katie whispered.

"I have," he admitted. "But it's messy that way if I'm not careful."

He didn't mention that more than once he'd stood by the window and jerked off while watching her and his stepmother out at the pool.

"Messy?" she asked. "What do you do when that happens? When you make a mess?"

"That's the part that feels so good," he grinned. "It's so good when it happens or when it's about to happen, that I don't think about or care about the mess. The more there is the better it feels."

"How do you clean up?" she asked, tipping her head to watch his balls as they moved up and down in time with his stroking hand.

"I use a towel," he said. "I either keep it under me or roll on my side and cum all over it. I learned a long time ago not to cum while standing up unless I had something to catch it all in."

Once again he didn't mention standing by the window watching Katie and her mother while stroking himself. When he did that, he most often snuck a pair of dirty panties out of the hamper to catch his hot spurts of cum. He was never sure which panties belonged to which woman, but he didn't care.

"Does it make a big mess?" Katie asked, curious lust making her belly tingle with excitement.

"Not always," he told her. "But there's almost always too much to do it without a towel or something handy."

"Should we have something?" she asked, looking around the room.

"Yeah," he said. "I'm getting close. We could use your shirt."

She glanced down, suddenly remembering that she was holding it up and exposing her breasts.

"Then I'd have to climb back out on the roof to get to my room topless," she giggled. "Why not use one of your shirts?"

"My shirts aren't sexy," he grinned. "They've never had breasts touch the inside of them."

"If you want something that's touched a sexy part of me, you could use my panties," she whispered. "If that's not too gross or anything."

He stopped stroking and stared at her, fighting to control the sudden and intense pressure to cum. His orgasm had already been close due to their conversation and the thrill of being watched. But she had no idea how mentioning her panties had almost caused him to erupt.

Just as he had no idea how the idea of her panties touching his cock gave her a thrill.

"Fuck yeah," he said, propping himself up on his elbows, afraid that if he was too enthusiastic it might freak her out. "That's hot."

She got off the bed, and the front of her tank top fell back down to cover her breasts. She hooked her thumbs into the waistline of her pajama bottoms and pushed them down, taking her panties down to her ankles at the same time. She stepped out of them and picked up the panties.

In the soft light Tim stared at the spot between her legs, fighting the urge to reach out and touch her. She saw him looking and a surge of heat pulsed through her, and after several seconds of enjoying his gaze she pulled her pajama bottoms back up.

She got back onto the bed, moving closer to him, watching him intently as she held out the panties to him.

"Do you want to hold them?" he asked. "I'm pretty close to cumming."

"Are you sure?" she asked anxiously, her eyes bright with need.

"Yeah," he said, wrapping his hand back around his cock. "We won't need them until I'm done."

He started stroking himself again, and this time he was moving his hand up and down faster. He wanted to savor this as long as he could, but the growing pressure in his balls was too intense to ignore, and he'd never needed to cum this badly before.

"What makes you feel best?" Katie asked, her eyes glued to his intense stroking. "Going fast when it happens? Or slow?"

"Both feel good," he groaned. "I always want to go fast, but sometimes going slow is so fucking good."

"What does it feel like?" she asked. "Right now?"

"It's close enough that I know it's going to happen," he said. "It hasn't started yet, but I know it's going to. There's so much pressure and everything feels so tight and tense. It's past want. Now it's all need."

He stopped stroking and moved his hand, letting his cock just point at the ceiling and throb, and Katie leaned closer, fascinated by how just seeing his arousal and need a few inches from her caused her hole to clench and drip into her pajamas.

"I want to see you cum," she whispered.

"I'm gonna," he panted. "So close."

He took himself in his hand and she watched, captivated by how he worked his thumb and finger over his cockhole, smearing the slippery precum all over his head before working his hand up and down.

She glanced at his face and saw that he was watching her, drinking in the sight of her staring at his cock, and she grinned at him as she pulled her shirt up to show him her breasts again.

"Oh fuck," he moaned.

"Go ahead," she encouraged him softly. "I want it to happen. Do it for me."

"I'm starting," he grunted.

He worked his fist up and down faster and faster, and Katie looked back and forth from the look of sheer pleasure on his face to the frantic stroking of his stiff cock. Suddenly he closed his eyes as a spasm of pleasure surged through his loins, and he tensed up.

Katie moved even closer and watched his cockhole, anxious to see his eruption.

With another sharp grunt his whole body spasmed, and his cockhole suddenly spit a ribbon of white cum two feet in the air.

"Oh oh oh!" Katie said, watching in delight as an even thicker bolt of cum shot up out of his cock.

Over and over the white fluid leapt forth, landing all over his belly and thighs and hand as he jerked, until he started to slow the up and down motion of his fist, his wet cockhead continuing to dribble out warm cum and add it to the sticky mess that covered him.

He stopped stroking and she realized he was staring at her, panting in relief as he let go of his cock. It was still hard and sticking up away from his body, but now it looked exhausted as well, as if all the urgent tension had gone, leaving behind just the trembling shaft.

"That looked like it felt good," she whispered with a grin, wondering what it would be like to feel a cock do that while buried deep in her wet cunt.

"It did," he agreed.

"Does it feel better now?" she asked.

"It feels sort of numb," he smiled. "But in a good way. It'll leak a lot and get soft over the next few minutes."

Hearing an invitation that Tim hadn't quite intended, Katie stretched out on the bed and rested her head on her hand, watching intently for several minutes as his cock relaxed, slowly becoming softer as his cum continued a steady drip from the tip.

When it had been completely soft for a while and was no longer dripping, Katie lifted her panties, and began to wipe them along his thighs and belly, sopping up as much of his sticky mess as she could.

He jumped at her initial touch, but smiled to himself as she moved the soft cotton panties along his skin, taking an erotic pleasure at the thought of his cum soaking into her underwear.

When she'd gotten as much as she could, he took his cock in his hands and squeezed it, and she realized he was working it like a tube of toothpaste, getting as much of the remaining cum out as he could. He rolled toward her and she twisted the panties inside out, finding a dry spot for him to wipe his cockhead on.

He looked around the room and then leaned over the bed to pick up his pajama bottoms, and Katie quickly lifted the panties to her face and inhaled the scent of his cum, feeling her belly twist with desire as her already wet hole clenched.

Tim pulled his pajamas on and turned to her.

"Do you still want to...?" he asked quietly, unsuccessfully trying to sound as if he didn't care one way or the other.

Katie knew he wanted to watch her cum now, and she had no objections. Never had she wanted to slide her fingers up into herself as badly as she did at that moment.

"Can I?" she whispered, nodding her head up and down. "I want to."

She moved up on the bed and stretched out again, and with a tenderness that shocked and aroused her Tim helped her pull her pajama bottoms off, staring with lust at the tiny tuft of hair at the very top of her slit.

"Beautiful," he said, almost to himself, and she felt warmth spread through her body.

She sat up and took her top off, revealing her entire naked body to someone in a sexual way for the first time ever.

"I'm already wet," she whispered, spreading her legs slightly and pushing her fingers along her crease. "From watching you."

"Wow," he whispered, moving closer so he could see.

She worked her fingertips through her arousal and then held them up, rubbing them together and spreading them apart so he could see her slippery cunt nectar.

"You're so... so... so wet," he said, looking up at her face.

She nodded her head and put her fingers back to her opening, using her fingers to spread the lips gently.

"It feels so good to touch it like this," she told him, her voice trembling. "Especially right here, the best spot."

Her finger was circling her clitoris, and he moved closer to stare in fascination at the engorged button, smelling her arousal and realizing just how intoxicating the scent of an aroused women could be.

"Is this how you do it?" he asked, trying to remember her questions to him.

"Yeah," she moaned. "Usually, I do it on my front through, but you won't be able to see if I do it like that."

"Does it feel better like that?" he asked. "On your front?"

She nodded and bit her lip, closing her eyes as a wave of pleasure twisted through her.

He stretched out beside her and pushed her, encouraging her to roll over.

"I want to see it how it feels best for you," he told her. "I want you to cum good."

"But you won't be able to see," she whispered, lifting her ass as she pushed her hand down between her body and the mattress to touch herself.

"I can watch your face," he said softly. "That will make up for the unfairness of not being able to see."

She took one of his hands and held it to her breast.

"You can feel me here if you want," she panted, another shiver of lust spasming through her. "I usually hold myself tight there when I cum."

He squeezed her breast, his finger rubbing the nipple softly while he pulled her close to him, and she gasped as her fingers started moving faster.

"I'm really wet," she told him. "I can't believe how close I am. It's going to happen soon."

"Good," he said, holding her breast tight. "I want it to."

"Really?" she asked, their eyes six inches apart.

"Fuck yes," he said. "This is turning me on as much as my own orgasm did."

"I'm going to cum," she whispered, her eyes wide. "Tim it's going to happen."

He squeezed her breast with one hand and used his other arm to hold her tight, and with their eyes locked together she felt a sudden surge of heat explode out from her center, followed immediately by constricting waves of pleasure and release as her orgasm overwhelmed her.

"Uh, uh, uh," she whimpered, staring into his eyes.

She rode the current of pulsing ecstasy, the feeling of hot release ebbing and flowing through her body and down her limbs as her orgasm absorbed her, causing her to rock back and forth against her stepbrother with total surrender to her orgasm.

At last, she realized that it had ended, her tingling clitoris slowly returning to normal after a feeling of frenzied throbbing, her body sweaty as she panted against Tim's shoulder.

"Jeezus that felt good," she whispered.

"I loved it," he said, stroking her arm with his fingers.

"Really?" she asked, lifting her head.

She'd thought that enjoying his pleasure was some sort of strange and curious thing she was experiencing. She hadn't expected him to share her need to witness another's pleasure.

"Just look," he grinned. "You really turned me on."

She spent a second or two not understanding him, and then she understood. She looked down and saw the unmistakable tent in his pajama pants.

"Again?" she giggled. "Already?"

"Oh fuck yes," he said with a chuckle. "I'm ready to go again just from being close to you."

"Do it," she said. "Cum again for me."

He rolled his hips and pulled his pants down, and grabbed his cock again, feeling the heat of her body pressed against his.

"Like this?" he asked, starting to stroke himself.

"Yeah," she said, watching his face. "I want to feel you cum while we're pressed up against each other."

"You won't be able to see," he said, echoing her earlier statement.

"Can I feel a little bit?" she asked shyly.

He nodded in response as he felt her hand slip along his abdomen. He wasn't sure where she planned to touch him, but the heat of her fingers against his skin was so amazing that he'd have settled for her just touching his stomach and called it the most sexual thing he'd ever felt.

But she didn't stop at his stomach.

Her fingers traced down along his belly to his hip, and then his thigh, and then she pressed her hot fingers against his balls and he shuddered and pulled her so tightly against his body that it almost hurt her, but his passionate embrace caused something to twist inside her.

Her fingers worked against his soft testicles for several minutes while he moved his hand up and down, both of them staring into each other's eyes as orgasmic pressure built at the base of his cock.

"I'm close," he said softly. "I'm going to cum soon."

"Good," she said with a smile.

"It'll make a mess," he groaned, wanting to warn her.

"Go ahead," she said, taking his sensitive balls in her hand and holding them. "That's what I want."

"Katie," he whispered, unable to say anything else.

She nodded in encouragement, knowing what he was feeling.

She kissed his chest gently, watching his eyes while she did it, and he tensed up and groaned.

She felt his arm moving faster and felt his balls tighten in her fingers, and she knew that he was ready to shed his self control and explode, and she squeezed her hand around his sensitive nuts and put her nose against his.

"Do it," she begged.

He lurched under her and she felt a sudden splash of hot cum on her ass and thigh, and she moaned with him as more and more cum flooded against her, his orgasm pouring out of his cock while he rocked against her.

The slippery wet semen ran across her ass and down her thigh, while even more landed on her fingers as they flexed around his spasming testicles.

"Fuck," he sighed.

She kissed him then, closing her eyes as she pushed her tongue against his, feeling a sense of freedom and happiness that she hadn't imagined sharing sexual could cause.

His cock continued to throb as his orgasm wound down, his hot sperm making a mess on them both.

She nuzzled against his neck and felt his pulse in his throat, holding him tightly while his body settled down.

After twenty minutes she moved, realizing that he was sound asleep. She got out of his bed and stared at his limp cock, smiling at how small and normal it looked despite its recent length and girth.

She had his cum all over her but she pulled her pajamas and t-shirt back on anyway, taking her cum soaked panties off of the bed and clutching them in her hand.

She kissed his forehead gently and looked around the room. She turned off his closet light and went to the window, stepping out in her barefeet onto the roof of the porch.

She returned to her own bedroom window and climbed through.

She sat on the edge of her bed in the darkness, wondering if Tim would be open to trying what they'd just done again sometime.

They were going their separate ways to college in a few hours, but they'd both be home for Thanksgiving.

~~

Thanks for reading this far! I know this was fairly vanilla compared to my usual stuff on Literotica, but my first sexual experience involved masturbating with a partner, so it's a cherished sexual memory of mine.

I hope you're in the middle of a great week whenever you're reading this, and I hope you and the people you hold dear are doing well!

IsabellaEmily