Crossing the Line

Kelly keeps kissing you as she settles over you on the bed. The playful confidence from a moment ago is still there, but something about hearing her actually say what she wants changes the mood between you.

There isn’t anything left to hint at anymore.

You slide your hands around her waist and hold her against you as the kiss continues. Her fingers move through your hair before settling against the side of your face.

Eventually, you pull back just enough to look at her.

“You’re really sure about this?” you ask.

Kelly looks at you for a second.

“Are you?” Kelly asks.

“Yeah,” you reply.

“So am I,” Kelly says.

She kisses you again, but you stop her after only a second.

“I’m serious,” you say.

“I know,” Kelly replies.

“And?” you ask.

“And I’m serious too,” Kelly says. “I want this.”

That settles it.

You pull her back into the kiss, and this time the last bit of hesitation between you seems to disappear with it.

Her hands move down your chest as she shifts against you. You let yours travel along her sides before reaching the waistband of her shorts.

Kelly feels where your hands have gone and breaks the kiss.

“Need some help?” Kelly asks.

“I think I can figure it out,” you reply.

“You sure?” Kelly asks with a grin. “You seemed pretty distracted earlier.”

“Can you blame me?” you ask.

Kelly glances down at herself before looking back at you.

“No,” Kelly replies with a grin. “Not really.”

She slides off the bed and stands in front of you. Her hands find the waistband of her shorts, and she slowly peels them down her legs before stepping out of them.

When she turns to toss them aside, you get your first unobstructed look at her ass in nothing but her panties. The soft, stretchy fabric fits snugly around her hips and follows the curve of her ass closely, sitting smooth against her without hiding much of its shape. After spending most of the night watching everything move beneath her shorts, seeing how the panties actually fit her makes it difficult not to stare.

Kelly catches you doing exactly that when she glances back over her shoulder.

“Finally get a good enough look?” Kelly asks.

“Getting there,” you reply.

She laughs and deliberately takes another second before turning back around.

“Greedy,” Kelly says.

“You knew what you were doing when you turned around,” you reply.

“Maybe,” Kelly says with a smile.

The joking fades as you watch her, replaced by the realization that this is actually happening.

When she turns back toward you, she catches you staring.

This time, she doesn’t tell you to look away.

Instead, Kelly stands there for another moment and lets you take her in. The confidence she had while showing off downstairs hasn’t gone anywhere, but there is something different about it now. She isn’t teasing you from a safe distance anymore.

She watches your eyes move over her, then places her hands on her hips.

“You like what you see?” Kelly asks.

“You already know I do,” you reply.

“I know,” Kelly says, smiling.

“Then why ask?” you ask.

“Because I still like hearing you say it,” Kelly replies.

You look her over once more before meeting her eyes.

“You look fucking amazing,” you say.

Her smile widens immediately.

“There it is,” Kelly replies.

She climbs back onto the bed and over you, bringing her face close to yours.

She kisses you again as her hands slide over your chest and yours settle against her bare waist.

For a while, neither of you says anything. The joking gives way to kissing and touching as you settle together on the bed, both of you taking your time despite knowing exactly where this is heading.

Eventually, Kelly pulls away and shifts beside you. She looks at you for a moment before moving farther onto the bed and lying back against the pillows.

The movement is simple, but you immediately understand what she is doing.

She adjusts herself against the pillows, her loose hair spreading around her shoulders as she gets comfortable. For the first time all night, she isn’t trying to put on a show or come up with another excuse to tease you. She simply looks up at you, waiting.

Her fingers hook beneath the sides of her panties. She pauses there for a second, meeting your eyes before sliding them down and setting them aside with the rest of her clothes.

As the panties come away, you get your first look at the lips of her pussy. A thin strand of her thick juices briefly stretches between her and the fabric before breaking, and when she tosses the panties aside, you can see the damp spot she has left behind on them.

Your attention immediately drops between her legs. It is the first time you have actually seen her pussy, completely bare and clean-shaven. She is already visibly wet, and seeing just how turned on she is makes everything the two of you have been building toward suddenly feel a lot more real.

Kelly catches you staring again, but this time she doesn’t tease you about it. She simply watches your reaction for a moment before reaching toward you.

You move closer, and Kelly reaches for you almost immediately, pulling you down toward her.

“Come here,” Kelly says quietly.

You settle over her, supporting yourself as she wraps her arms around you.

“Still good?” you ask.

“Yeah,” Kelly replies without hesitation. “Come on.”

She kisses you again.

You shift between her legs and take your cock in your hand. Before going any farther, you rub it between the wet lips of her pussy a few times, coating yourself in her juices. Kelly’s breathing changes beneath you as you do it, and she tightens her arms around you.

You look down between your bodies as you line yourself up. Then you slowly press forward, feeling her tight, wet pussy close around your cock for the first time.

Kelly takes a sharp breath and pulls you closer.

What follows feels different from everything that led up to it. There isn’t a joke to hide behind or another excuse about getting comfortable. You both know exactly what you’re choosing, and when you finally cross that last line together, neither of you backs away.

For the first few moments, everything slows down.

Kelly stays close, one arm wrapped around you while her other hand rests against your shoulder. You start thrusting forward slowly, giving both of you time to adjust to the new sensation. You kiss her as the two of you find a comfortable rhythm together, paying attention to each other’s reactions rather than rushing.

Her forehead eventually rests against yours.

“You okay?” you ask.

“More than okay,” Kelly replies.

“Just checking,” you say.

“I know,” Kelly replies before kissing you. “Keep going.”

You do.

You keep thrusting into her, slowly increasing the pace as the initial unfamiliarity begins to disappear. Each movement starts feeling more natural than the last, and Kelly responds by pulling you closer and moving with you.

The uncertainty that was there at first gradually disappears. The more comfortable you become together, the more the woman from downstairs starts coming back. Her hands move more confidently over you, and that familiar smile appears whenever she catches you watching her.

You lean down to kiss her again at the exact moment she lifts her head to meet you, and instead of your lips meeting, your noses bump awkwardly together. Both of you immediately pull back.

For half a second, you just stare at each other.

Then Kelly starts laughing.

“Very smooth,” Kelly says through her laugh.

“You weren’t exactly helping,” you reply.

“Oh, so it’s my fault?” Kelly asks with a grin.

“Completely,” you answer.

“I’ll keep that in mind,” Kelly replies.

You both laugh as you lean down again, this time managing to actually find her lips. She is still smiling when you kiss her, and the stupid little accident strips away the last bit of pressure surrounding what the two of you are doing.

Whatever awkwardness was left between you disappears with it, and soon you’re moving together much more naturally. She tells you when something feels good and pulls you closer whenever she wants more, while you learn to read the smaller reactions she doesn’t put into words.

As your rhythm becomes more confident, your eyes occasionally drop between you. Her push-up bra is still firmly in place, but it moves with her now instead of simply holding everything still. Each movement sends a noticeable bounce through her chest, her breasts shifting and jiggling inside the cups as you move together.

Kelly catches where you’re looking and glances down at herself.

“Distracted again?” Kelly asks between breaths.

“A little,” you admit.

“I can tell,” Kelly replies, smiling before pulling you closer.

You keep moving, gradually letting yourself thrust harder now that both of you have settled into the rhythm. The change gets an immediate reaction from her. Her quiet breathing turns into louder moans as you fuck her harder, and her fingers tighten against you every time you push into her.

Then, in the middle of one thrust, your cock unexpectedly slips out.

Both of you stop for a second.

Kelly looks down between you and then immediately back at you.

“Put it back in,” Kelly says.

You reach down, guide yourself back into position, and push into her again.

“Oh, fuck,” Kelly moans as you slide back inside.

You start moving again, quickly finding the rhythm you had before.

The joking becomes less frequent as the intensity builds.

Kelly’s breathing changes first.

You start pumping faster, enjoying how good her tight, wet pussy feels around you and not immediately realizing just how close she is getting.

You notice the way she holds you tighter and how much harder it becomes for her to maintain the confident little smile she has worn most of the night.

Her hand slides behind your neck while the other grips your shoulder, holding you tightly against her as you keep moving. The closer she gets, the harder her fingers dig in.

You can feel her pussy beginning to pulse around your length as you continue thrusting. Kelly lets out a strained whimper and presses her face against you, clearly struggling to hold herself together as the sensation keeps building.

“Fuck,” Kelly whimpers, barely managing to get the word out.

“You good?” you ask.

“Don’t stop,” Kelly replies immediately.

You don’t.

The urgency in her answer finally makes you realize what is happening. The changes in her breathing, the way her body keeps tightening beneath you, and the way she is holding onto you make it obvious that you’re about to make her cum.

Once you realize it, you stop thinking about anything except pushing her over the edge. You keep thrusting into her, trying to maintain what is clearly working instead of changing the pace on her.

Her eyes close as she clings tighter to you. She tries to say something else, but whatever she meant to say gets caught somewhere between a breath and a broken sound.

“Oh my God,” Kelly finally manages to say.

You look at her, and the surprise on her face is unmistakable. For once, she doesn’t have some teasing comment ready. She looks almost caught off guard by how strongly the moment hits her.

“Oh my God,” Kelly says again, barely getting the words out this time.

She pulls you closer, burying her face against you as her breathing turns uneven. Every attempt to say something else falls apart before she can finish it, and eventually she gives up trying altogether.

A moment later, the tension finally breaks. She holds tightly to you through it, visibly overwhelmed by the intensity before slowly beginning to relax again.

You keep thrusting as her orgasm gradually passes, slowing only as you feel her body begin to relax beneath you. Once she finally starts coming down from it, you stop and pull your cock out of her.

You glance down between you. Her juices have left your cock slick and wet, making it obvious just how turned on she had gotten before she came.

You slow down and look at her.

For several seconds, Kelly doesn’t say anything.

Then she starts laughing quietly.

“Holy shit,” Kelly finally says, still trying to catch her breath.

“You okay?” you ask.

“Yeah,” Kelly replies immediately. “I just… holy shit.”

You smile as she lies there staring up at you.

“That good?” you ask.

Kelly turns her head toward you and gives you an almost disbelieving look.

“I did not expect you to make me cum that hard,” Kelly admits.

“Is that a compliment?” you ask.

“A huge one,” Kelly replies. “That felt fucking amazing.”

She takes another deep breath and lets it out slowly, still looking a little stunned by herself.

“I seriously couldn’t even talk for a second,” Kelly says.

“I noticed,” you reply.

“Don’t look so proud of yourself,” Kelly says, although the smile returning to her face ruins any seriousness behind it.

“Little late for that,” you reply.

“Yeah,” Kelly says with a quiet laugh. “I guess you earned it.”

You laugh and kiss her.

For a little while, neither of you makes any effort to continue. You stay close together while she catches her breath, and the sudden quiet gives you a second to process what just happened.

Kelly eventually opens her eyes again and catches you looking at her.

“Why are you looking at me like that?” Kelly asks.

“I’m just enjoying this,” you reply.

“Me lying here trying to remember how to breathe?” Kelly asks.

“Pretty much,” you say.

Kelly shakes her head, but she smiles as she reaches up and runs a hand along the side of your face.

“You’re way too pleased with yourself right now,” Kelly says.

“You literally just told me I earned it,” you remind her.

“I know,” Kelly replies. “I’m already regretting that.”

“No, you’re not,” you say.

Kelly looks at you for another second before her smile widens.

“No,” Kelly admits. “I’m really not.”

She kisses you, but there is already something changing in her expression.

You recognize that look.

It’s the same one she had downstairs right before every supposedly innocent decision somehow ended with her teasing you even more.

Her hand stays against your face for a moment before slowly sliding down to your chest. The exhausted look she had a minute ago is disappearing quickly, replaced by that familiar confidence.

“Feeling better?” you ask.

“Much,” Kelly replies.

Her palm presses against your chest. At first you think she’s simply touching you, but then she starts applying pressure.

You look at her hand and then back at her. The answer becomes obvious before either of you needs to say anything.

Kelly presses against your chest again, and this time you let her guide you backward.

The second you do, Kelly starts moving with you, following until she is climbing over you.

She brings one leg across your body and plants her knee on the mattress beside your hip. Her other leg follows, leaving her straddling you with one knee on either side. She settles her weight over your lap and straightens above you, her hands resting against your chest as she gets comfortable in the new position.

As she lowers herself, the warmth of her pussy presses directly against your cock. She settles with your shaft trapped between your bodies, her wet lips resting along either side of it.

Instead of immediately going any farther, Kelly rolls her hips. Her pussy slides slowly along the length of your already slick cock before she reverses the motion, grinding herself against you again.

“God, I’m wet,” Kelly says as she looks down between you.

She rolls her hips again, letting out a quiet moan as she feels herself slide along you.

She keeps grinding, gliding her wetness back and forth along your shaft while watching your face. There is nothing accidental about the movement. She takes her time with it, clearly enjoying being the one controlling the pace now.

The position immediately reminds you of the couch downstairs, except there is no pretending this time that she somehow ended up there by accident. Her thighs press against your sides, her loose hair falls around her shoulders, and the push-up bra that she has been wearing all night is still holding her chest high in front of you.

“You recovered fast,” you say.

“I told you it felt amazing,” Kelly replies. “I didn’t say I was done.”

She settles above you, her loose hair falling forward around her face as that familiar confident smile returns completely.

“You look way too happy about this,” you say.

“I am,” Kelly replies.

“Should I be worried?” you ask.

“Probably,” Kelly says.

You laugh.

She leans down until her face is only inches from yours.

“Besides,” Kelly says, “you’ve been in charge long enough.”

“Have I?” you ask.

“Yep,” Kelly replies.

She gives you a quick kiss before sitting back up.

As she straightens, she catches your eyes dropping toward her chest again. This time she doesn’t call you out for staring. Instead, she brings both hands up to her breasts and gives them a slow squeeze through the bra, deliberately pushing them together while her hips continue moving against you.

You watch her hands as she plays with her tits, squeezing and adjusting them inside the cups before letting them bounce back into place. She smiles when she sees that she has completely stolen your attention.

“You really do like these, don’t you?” Kelly asks.

“You know I do,” you reply.

“I know,” Kelly says.

She squeezes them together again as she rolls her hips, continuing to glide her wet pussy along the length of your cock. The combination makes it difficult to decide where to look, which seems to be exactly what she wants.

After teasing you for another moment, Kelly finally reaches behind herself.

Before doing anything else, Kelly reaches behind herself. You hear the clasp of her bra come loose, and the straps immediately relax against her shoulders.

She slides them down her arms and pulls the bra away, finally taking off the last thing she has been wearing all night. She tosses it toward the growing pile of clothes without taking her eyes off you.

For the first time all night, you get an unobstructed look at her chest. Without the push-up bra squeezing everything together, her breasts settle naturally against her body, full and soft with their weight changing their shape slightly as she sits upright over you. Her nipples are exposed now too, and after spending so long staring at the cleavage the bra created, actually seeing all of her catches your attention immediately.

Your eyes move from one breast to the other before taking in the rest of her body and eventually returning to her chest. You don’t even try to hide the fact that you’re checking out her boobs.

Kelly watches you do it, apparently in no hurry to interrupt. If anything, she seems pleased that finally taking the bra off has gotten exactly the reaction she wanted.

“Well?” Kelly asks.

You keep looking for another second before meeting her eyes.

“Yeah,” you say. “Definitely worth the wait.”

Kelly laughs and straightens slightly above you, which only gives you a better look.

“I knew you’d like them,” Kelly says.

“You haven’t exactly been subtle about showing them off,” you reply.

“And you haven’t exactly been subtle about staring at them,” Kelly says.

“Fair,” you reply.

She smiles down at you, clearly enjoying having your full attention.

“Better view?” Kelly asks.

“Much better,” you reply.

“Good,” Kelly says with a satisfied smile.

She holds your gaze for another second before slowly leaning down over you. Her loose hair falls around both of you as she brings her lips close to your ear, deliberately taking her time.

“My turn,” Kelly whispers into your ear.

She stays there for a moment, close enough that you can feel her breath against your skin, before slowly lifting her head again. The satisfied smile is still on her face when she looks down at you.