Midnight Cometh

“Go ahead, Maddy. Cum for me.” You encourage her.

“I don’t think I can hold back a scream if I do, Mr. Craig. This is… this feels too good!” Maddy says, and she doesn’t seem to be joking as she almost shouted towards the end of her response. You’re at least thankful she has enough awareness of the possible issues

“You have to try, Maddy. The neighbors might hear if you do.” You tell her, hoping that she understands that you’re definitely concerned that if she gets too loud, it actually might reach her family.

“I don’t know if I can!” Maddy replies loudly once more, and she’s the one that’s rubbing on your cock now, as you basically stopped to try and postpone her from cumming until you can ensure she can control her volume.

“Bite my neck.” You tell her, as she increases her pace.

“No! I don’t want to hurt you!” Maddy replies, and she’s definitely getting loud with her response, as her breathing is getting heavier too. You try to kiss her, but Maddy’s too busy breathing heavily that making out will probably not stop her from screaming in pleasure when she finally reaches climax.

“I have an idea, but it might be a bit dirty.” You tell her. “Okay, maybe ‘a lot’ dirty.” You then correct yourself after you take into consideration all the factors of this little idea of yours.

“I don’t care… haa~” Maddy replies, and her voice sounds lust-drunk in her reply.

You pull back your hips to pause her from grinding on you for a moment and to prevent her from getting off before you and her have precautions in place. You push her leg that’s over yours, before pulling her panties down.

“Mr. Craig,” Maddy moans, unsure of your intentions.

“Trust me, Maddy. Let’s just get your panties off.” You tell her, and she doesn’t resist any further. Once her panties are finally off, and you’re holding them in your hand, you raise them up so that it’s near yours and Maddy’s heads.

“I did say my idea was dirty.” You repeat, before finally telling her, “Open your mouth, Maddy.”

“I-” Maddy tries to say, her eyes darting back and forth between you and her wet panties.

“I won’t go further than what we’ve already been doing. We’ll do that when you’re ready.” You add to assure her, as you realize that might be one of her concerns as well. “For now though, this is my best idea at muffling your moans a bit.” You add, realizing too late that the appropriate word to describe might have been ‘kinkiest’ instead of ‘best’.

“It’s… it’s actually okay if you do it, Mr. Craig. I’ve… I’ve actually been practicing for this moment.” Maddy admits, solely staring into your eyes now, and no longer caring about her wet panties in your hand.

PRACTICING!?

WITH WHO!?

“Wait… what?” You ask in total confusion.

“Becca lent me one of her toys… and I’ve been using it to prepare for you.” Maddy confesses, and the image of Becca’s toy chest from last night flashes in your mind. You remember the empty silhouette that you saw, and you immediately connect the dots.

“Are you sure, Maddy?” You ask her, and Maddy nods shyly, before opening her mouth like you asked her to do before. You can’t help but smile at Maddy’s response. Not a devious or perverted smile, but one that you hope she finds appreciative and sweet, for allowing you to take her virginity from something that’s not plastic.

You give her one last sweet kiss, before taking her scrunched up panties in your hand and inserting them inside her mouth. You lift her leg up and place it over yours again, before shifting the tip of your cock towards the entrance of her now bare pussy.

“I’ll be gentle.” You promise her, before slowly penetrating her walls with just the tip of your dick. You see Maddy immediately bite down on her panties, and you can feel her nails dig into your back.

You can barely get your cockhead inside her, despite how wet she is, due to Maddy being extremely tight and most likely not fully relaxing yet. You don’t **** the issue to go deeper inside her as breaking her resistance might cause her more pain than she’s ready for.

“I’ll start moving now, okay?” You inform her, but Maddy’s unresponsive. You look at her pained expression, with her eyes closed, head leaning backwards, letting out deep grunts as she continues to bite down on her own wet panties. You pull out of her slowly, only leaving the tip of your cock as the only part that remains in contact with her dripping wet slit. You penetrate her again, even slower than before in hopes that it’ll help her relax.

Maddy just continues grunting, seemingly with every centimeter that enters her, and when you feel the resistance inside her inner walls again, you stop to ensure she’s not getting hurt. You feel her tightness around your cockhead, enveloping it with her warmth. Without moving, it seems Maddy’s trying to relax her inner muscles, as you feel her walls wiggle around your cockhead, accentuating just how wet she is.

You spend a few more seconds like this, inching the rest of your cock with every wriggle of her pussy’s walls as she tries to relax and take more of you in. When you feel like the resistance is getting too much again, you slowly try to pull out to repeat this process all over again. Only this time, Maddy has something to say about it.

Her eyes are open now and there’s a determination in them you can sense. She mutters something you can’t understand due to her mouth being stuffed by her panties, so you move your hand to try and remove it from her mouth. Maddy sees what you’re doing and decides that she doesn’t actually need to vocalize what she wants. She just needs to show you.

Maddy moves both her hands onto your buttcheek, grasping them tightly and unintentionally digging her nails into your skin, before mirroring what you did earlier and pulling you in while also pushing her hips closer to yours. Maddy’s eyes immediately begin to water, but she’s determined to take all of you inside her. She’s giving almost birthing grunts of pain through her panties, but her eyes look manic and her smile is euphoric. The grunts are now being sandwiched between chuckles as Maddy continues to try devouring the rest of your shaft with her pussy from this position, and with every new inch forcing its way inside her walls she lets out chuckles of victory.

“Maddy, you don’t have to take all of me all at once.” You say with concern, as you’re not sure if she’s doing this in the hopes that that’s what she thinks you want. After hearing your concern though, Maddy mutters something under the panties again before seemingly getting more determined, tightening her grip on your buttcheeks again and pulling you in harder.

Realizing she’s really determined for you to not hold back either, you shift your hands to hold her hips, before reminding her, “Don’t forget to breathe,” in the hopes that it’ll help her relax her muscles. Maddy nods eagerly, as you tighten your own grip on her hip bones, and she takes in a deep wincing breath, before you **** the issue and buck your hips forward forcefully while pulling her down onto your shaft.

“NNNNNNNGGGGHHH!!” Is the only noise that’s coming from Maddy, as her entire upper body tenses up and leans backward, with even her eyes rolling backward; while her legs convulse beneath you as a result of the much more intense orgasm than the one she had before. Her breathing is labored too, as she’s **** to breathe through her nose.

When you do take out the panties stuffed in her mouth, every breath she takes is still bated, and it doesn’t seem like she’s even exhaling. As a kicker to just how intense her orgasm is, there’s still a steady stream of fluids you can feel coating your thighs coming from Maddy’s pussy.

All that, just from taking you all in for the first time. So you don’t move a muscle until Maddy starts to relax her tense body again.

When Maddy finally does take a deep breath, her body stops tensing up as well and she’s able to lean into you instead of backward. As soon as her forehead is resting on your chest though, her legs start convulsing again, and you can feel another stream of fluids squirting underneath you. You let her ride this second wave again, hugging her and rubbing her back with your hand.

It takes her a few more seconds to fully recover, but she finally returns to somewhat normal breathing after a minute or so. All the while, the entirety of your fully erect cock, is still inside Maddy. You’re still hesitant to pull your cock out, in fear of another deluge of Maddy’s fluids.

“Are you thirsty?” You teasingly ask Maddy, and she weakly pounds your chest for the tease. “That was intense.” You then comment with a chuckle, and Maddy smiles weakly but doesn’t respond for a while.

…

Then you feel it.

You feel Maddy’s clit on the base of your crotch, rubbing against your pubes.

You feel her vaginal walls grind on your shaft, and the deepest parts of her massage your sensitive cockhead.

“Maddy?” You ask her, eerily similar to how you did earlier when you thought she was asleep and she was grinding on you.

“You haven’t reached orgasm yet” Maddy responds, revealing her motivation without you having to ask.

“Don’t over-exert yourself.” You tell her.

“I’ve recovered, Mr. Craig. I can keep g-AH!—” Maddy starts to say, before she gets cut off by a noise coming from your phone.

*ALARM*