No Sleep 'til Midnight

“More.” Maddy says, almost moaning the word when she does. “I want more of this feeling!” She suddenly shouts in excitement, and you have to laugh at the sudden shift to eagerness in her voice.

“What happened to sleeping?” You jokingly ask back, unable to hold back a chuckle at how much her attitude has changed since she started this ‘favor’ of hers.

“I’m not tired yet.” Maddy replies matter-of-factly, before she starts rubbing her wet panties all over your equally wet leg again.

“I can see that.” You reply with a chuckle, and Maddy can’t help but chuckle too. “Maybe ‘feel’ would be more accurate.” You add, and Maddy blushes this time.

“I’m sorry, Mr. Craig. It just feels so~ good.” Maddy admits, still not stopping her unabashed grinding on your leg. “Your leg feels way~ better than a pillow.” Maddy adds, and you can’t help but laugh at the comparison.

“Thank you?” You reply, still laughing; and Maddy has to hide her face in your chest from embarrassment, but she still doesn’t stop grinding on you though. “Hey~, I’m not laughing at you, okay? I just laugh sometimes when I find something cute.” You tell her, after making her look at you by directing her chin with your fingers.

Now that Maddy’s looking into your eyes while she continues to sensually grind her wet nub on your leg, you see her bite her lower lip to resist the urge to moan. You take the initiative and lift her head up with your hand so you can give her a passionate kiss. You can smell the strawberry in her lip balm again as you play with each other’s lips, repositioning your mouths after each time they touch, and only letting your tongues get in on the action momentarily before focusing on each other’s lips again.

Maddy only breaks away from the kiss when she can’t help but shudder, which is undeniably another orgasm, albeit less intense than the previous one. She finally raises her leg that’s spooning you higher up your leg, and her knee accidentally grazes your semi-erect cock, which makes Maddy immediately lower it back down before staring wide-eyed at you as if she did something wrong.

“I’m sorry, Mr. Craig. I-I didn’t mean to…” Maddy apologizes in panic, and you can’t help but chuckle again.

“It’s alright, Maddy.” You say, still smiling wide from how adorable you think Maddy’s being. “Actually…” You then add, before turning your body towards her to face her, laying on your side instead of your back.

Maddy’s arm that was across your chest and hugging you is now lower and her hand is resting on your hip, her chest that was pressing against your side from the previous position is now a few inches away from your own upper body, while her leg that grazed your semi a moment ago is no longer over your leg.

“I hope you don’t mind if we continue in this position, Maddy.” You tell her, before taking her hand that’s on your hip, and placing it behind you so she can hug you. You then move your arm on her back and pull her in closer so her breasts are pressed against your chest. You then move your hand slowly further down Maddy’s back, grazing her ass along the way, until it reaches the back of her thigh. You lift her leg and place it on top of your own leg like before, before finally pulling her lower body closer to yours and letting your semi-erect cock brush against the wet spot of her panties.

Maddy gasps as your crotches rub against each other through your clothes, and her wide eyed expression from before has shifted into something sultrier, looking at your lips as she bites her lower lip to express just how much she wants to kiss you again in this position. You’d oblige her in just a moment, but there’s something you want to do first.

“Ahh~” Maddy moans, as soon as you rub the outline of your cock on her wet nub. “Mr. Craig,” She moans after you raise the hem of her dress, before you then place your hand on her buttcheek to squeeze it slightly.

“I hope you don’t mind this change in position.” You say with a smirk, knowing full well that Maddy doesn’t mind your initiative at all.

“Of course not, Mr. Craig.” Maddy answers, shifting her stare into your eyes when she answers. “In fact,” Maddy says before placing her own hand on top of your buttcheek, before pulling your lower body closer so it rubs on her wet panties again. “I quite like it.” She adds, before finally starting a rhythm with her hips, and starts to grind on the outline of your cock underneath your shorts. “A lot.” she continues, before squeezing your buttcheek too, and you can’t help but be pleasantly surprised by her response.

You respond to her rhythm and try to match it with your own, trying to meet her clit with your frenulum with every motion of your hips, making her moan again. You grunt a little bit as well, as this is definitely more stimulating for you now too. The two of you continue grinding on each other like this, and Maddy’s mouth opens slightly to let out a moan, making you glance at her lips for a moment.

When you go back to her eyes, you can see she’s back to staring at your lips, and you decide to give her what she’s been non-verbally begging for since the two of you shifted to this position. Unlike before though, you lead with your tongue this time, invading the space between her lips and greeting the tip of her tongue with yours. You can feel Maddy’s eagerness as it tries to welcome your invading tongue by swirling her tongue around it instinctively. Maddy’s lack of experience with these kinds of things shows itself though, seemingly unable to multitask now that she’s focusing on making out with you, and the rhythm of her hips all but stopped.

Since your hand is still resting on top of her buttcheek, you take control of the pace of your crotches grinding on one another by pulling her hips towards you and keeping it there, squeezing her ass cheek as you start grinding on Maddy’s wet panties quicker than before, but not quick enough to lose the sensuality of the time you’re sharing together. Still, it only takes a few strokes over her panty-covered nubbin that she breaks away from your kiss entirely to let out a gasp of pleasure.

You’re not one to talk either, as your cock is fully erect now and it’s trying to push over the band of your shorts to get out, and it’s mostly your shaft that’s rubbing on Maddy’s wet panties now. You take your hand off her ass momentarily to lower your shorts and boxers a bit to free the head of your cock from its confines. As soon as it’s free, you pull Maddy’s crotch back in, and you can feel the wet cloth of her panties and the outline of her outer pussy directly on your frenulum this time.

You and Maddy grind on each other one more time, and sensations on the tip of your dick are definitely a lot more intense. It seems the sensation is more intense for Maddy too, as every breath she takes is seemingly a moan of pleasure too.

Since the two of you are no longer making out, your mouth is free to find a new target. With Maddy’s chin being raised, you decide to start from there. You plant kisses on her chin, going lower and lower along her neck, before deciding to focus on the area connecting her neck to her shoulder. Resisting the urge to leave her a hickey since you don’t want her to get questioned by her grandparents in the morning, you decide to stick to planting sweet kisses on that instead, refraining from sucking on the skin that would leave an obvious mark.

Maddy continues to moan in pleasure, as her hand that was once on your ass begins to explore your back, eventually deciding to hold onto your hair and keeping your head from leaving the area you’re currently focusing on. You can’t see much in the dark, and with her head keeping you near her shoulder, there’s not much to see; so you decide to close your eyes and try to focus on your other senses.

The most intense feeling is still between your legs, as your exposed frenulum and Maddy’s clit continue to rub off on each other. You feel how perfect the size of Maddy’s buttcheeks are in the palm of your hand. You decide to add to Maddy's pleasure by lowering your hand to her underbutt, and glancing the tip of your fingers on the area of her panties where her pussy’s entrance would be.

You feel Maddy’s fingers grabbing a handful of your hair, and you can smell the minty and herbal shampoo or conditioner Maddy uses on hers. Finally, you focus on the sounds. Your bedroom is deathly quiet except for two things: Maddy’s moaning, and ‘schlick’ noises that are coming from your lower bodies as your cock rubs on Maddy’s wet panties. You and Maddy spend a few minutes like this, just grinding on each other; before something else finally mixes in with the only two distinct noises you can hear.

“I think I’m going to…” Maddy gasps.

“You’re close to cumming?” You ask to confirm, and Maddy just gives a shy “Mm-hmm” as a response, before hiding her face on your shoulder.

“Go ahead, Maddy.” You encourage her.

“Cum for me.”