Sleeping With Maddy

“Won’t your grandparents be looking for you?” You ask Maddy.

You and Maddy are outside your bedroom door, with your hand already on the doorknob and ready to open it; only to be reminded that the obvious place Maddy’s favor will go, might lead to an awkward and embarrassing ending for both of you if her grandparents start looking for her if she’s not home by a specific time.

“Oh, I-uh, I kinda told Grammy and Grandpa Rick that I’ll be helping Brooke move in… and, um, to not wait for me. They gave me their keys.” Maddy shyly reveals, swaying her hips in place like a little schoolgirl trying to keep a secret. You also notice the naughty smile on Maddy’s face, reminiscent of every teenager’s proud smile of getting one over their parents to avoid supervision.

You just give Maddy a knowing smile as a response, before finally turning the doorknob in your hand and gently swinging your bedroom door open. You gesture to Maddy and say, “After you,” as a way to invite her in, and close the door behind you once you’re both inside. You flick the lights open to your room, and Maddy surprisingly flicks them off as soon as you do.

“If it’s okay, I’d rather have the lights off for this favor I’m asking.” Maddy tells you shyly.

“What exactly do you have in mind, Maddy?” You ask her teasingly, knowing full well there are very few ‘favors’ you can do for her inside the bedroom with the lights off.

“Um… just get on the bed with me.” Maddy replies, before taking your hand and leading you towards your own bed. This time, Maddy does the ‘After you’ gesture, telling you to get on the bed before her. You’re wondering if she wants you to get naked already, but that might be getting too ahead of yourself, and you’ve been reminded by Paige not to assume too much; so you do as Maddy requests and get on the bed fully clothed.

You lie on your back in the middle of your bed, and you can’t deny that the vision of Maddy standing over you in bed is a lot more ‘Chucky’s going to kill you’ than your girlfriend is watching you relax in bed. You can’t help but subdue laugh at your fucked up thoughts and Maddy notices you chuckling to yourself.

“What’s so funny?” Maddy asks curiously, laughing with you. “Is this weird?” She adds.

“No. I was just wondering when you’re going to join me.” You try to play it off, not wanting to admit what was actually going through your mind.

“Oh! Um~, right.” Maddy reacts, realizing herself that she was just watching you lay on the bed alone. “I guess it was kind of weird for me to just watch you, wasn’t it?” Maddy self-consciously asks, as she sidles up next to you in bed.

“I honestly didn’t mind. I just wanted you next to me.” You sweet talk her, before wrapping your arm around her shoulder, as she rests her head on your chest and spoons you. You immediately notice her own chest pressing onto your sides, and you can feel the softness of her breasts with it. Maddy then wraps her leg around yours, and whether intentional or not, she has her crotch just resting on your thigh. You can feel the flat nub that’s covered by her panties, and you have to remind yourself to remain patient and refrain from going further than Maddy’s request.

…

Maddy doesn’t speak or do anything for a few minutes. She just continues hugging you and resting her head on your chest. Your body can feel her breathing, as every breath she takes nudges the softness of her tits slightly along your ribs. Meanwhile, you switch between watching her just rest next to you with her eyes closed and the ceiling of your bedroom, enjoying this quiet moment with her.

It takes about another couple of minutes before Maddy adjusts her leg that’s wrapping yours to wrap it a little tighter, and you can feel her crotch grinding on the bare skin of your thigh a bit, raising your shorts leg up as she does. This is exactly when she takes a deep breath, almost as if she’s taking in your scent.

“Maddy?” You finally address her.

“Yes?” She asks back.

“Is there any more to your favor?” You ask her, and she finally shifts her head so she’s looking at you, and you see her content smile shift to a wide one when she sees that you were watching her.

“Oh, um… No. This is it.” Maddy answers, and her infectious smile makes you smile too. You go back to staring at the ceiling, because if you stare at Maddy’s eyes any longer you might go beyond Maddy’s requests and take this further than she seems to have intended.

It seems you were wrong about the amount of ways her ‘favor’ could go, as you didn’t expect that just laying next to you in bed would be enough for her. Then again, maybe you didn’t take into consideration that Maddy’s affection for you is probably the most innocent among your girlfriends.

‘Counterpoint…’ Another part of your brain then chimes in. ‘She had a massive Lust Score for you before she even met you’

Then there’s that…

You look back at Maddy and she’s gone back to not looking at you, and just contently resting her head on your chest. Unlike before though, Maddy has her eyes open this time around, and you can tell she’s thinking of something. Maddy’s smile has gone back to the content smile she had before too, so you can at least surmise that whatever she’s thinking about, it’s at least a happy thought.

It only takes a moment before Maddy voices out loud what it is she’s thinking about though.

“I still can’t believe you’re actually here with me. Can you pinch me so I’m sure I’m not dreaming?” Maddy comments, and Maddy’s sweetness makes you chuckle before doing as she requests and you pinch her arm lightly.

“You’re not dreaming, Maddy.” You assure her, after you pinched her arm.

“For a moment there, I was afraid I’d wake up back in my room and I’m just hugging my pillow again.” Maddy admits with a chuckle of her own.

“Did you often imagine your pillow to be me?” You teasingly ask, expecting her to obviously answer ‘No’.

“All the time.” Maddy surprisingly answers. “That's why I asked if it’s okay to do this with you tonight. Back home, whenever I wanted to fall asleep, this is what I’d do. I’ll hug my pillow just like this, and imagine it was you.” Maddy explains, tightening up her hug, and you can feel her crotch grind even more aggressively on your thigh. You’re not sure if that was intentional or just because she just had to adjust her leg to tighten her hug, but you can’t get your mind off it now.

“You don’t need to pretend with a pillow anymore, Maddy. I’m real. This is real. And I’m just as happy as you that we’re together like this.” You assure her again.

“Thanks, Jay. That’s really comforting to hear.” Maddy tells you, and she hugs you tighter again; and without fail, you feel the nub of her crotch grind on your thigh again. “It’s such a shame I can’t sleep with you tonight.” Maddy adds, and it makes you close your eyes in acceptance that this is as far as Maddy wanted this night to go.

“We can always do it when you’re ready, Maddy.” You tell her honestly.

“But I think a quick one wouldn’t be the end of the world.” Maddy then says, and you don’t want to assume what she means by that, but your brain is definitely curious if she’s saying what you think she’s saying.

She was not.

“Can you wake me up before it gets too late?” She then asks, shattering whatever impure hopes you had. “I’m sure Grammy and Grandpa Rick would want me back before midnight, and I’m not sure if Tricia wouldn’t tattle on me if I get back later than that.” Maddy adds.

“Of course, Maddy. I wouldn’t want you to get in trouble with your grandparents.” You assure her. Maddy finally looks back at you with the same happy and content smile she’s had on since she sidled up next to you on the bed. Maddy adjusts to get more comfortable in her cuddling of you, before finally closing her eyes to grab the quick nap that she apparently meant when she said a quick ‘one’ wouldn’t be the end of the world.

You take your phone out of your pants’ pocket and set an alarm for just before midnight, so you can keep your promise to Maddy that you’ll wake her up before it gets too late. Afterwards, you then decide to get more comfortable too. You adjust your head to find the best spot on your pillow, before finally closing your eyes as well for a much needed rest.

Maddy’s warmth helps you relax, and her breathing helps as a calming agent for your mind. Despite all the perverted things you thought Maddy’s request would lead to, this turn of events might actually be the one that you needed more. There’s no denying you’ve been sexed up the past few days, and a break from that might be exactly what you need.

…

…

…

Something prevents you from falling asleep though…

You’re feeling it on your thigh again.

More consistently this time.

She’s definitely grinding on your leg.

You can even feel the fabric of her panties moistening a little bit as she continuously rubs herself onto your thigh.

When you hear Maddy try and stifle a moan, you can’t hold yourself back from addressing it.

“Maddy?” You call out to her in a whisper, not wanting to wake her up if what she’s doing is something she’s doing in her sleep.

“This is the only way I can fall asleep sometimes, Mr. Craig. I hope it’s okay.” Maddy whispers back. “And I hope it’s okay that I call you ‘Mr. Craig’ again for this. “ Maddy then adds, right before her grinding of her crotch on your thigh becomes more shamelessly apparent.

“That’s how I’ve always called you in my fantasies.”