Date After Work 5 - Uncharted Territory

How the HELL is this going to fit in there?? You only feel her lubed up tip press against your asshole and it already feels like a god damn tree trunk. This is it. This is where you die.

"I'll go real slow, don't worry." Zoey tries to sooth you and gently strokes the side of your hip. "Tell me whenever it's too much."

"Yeah." you croak and squeeze the sheets. Three fingers. How the fuck did you think three fucking fingers could properly prepare you for a cock?? HER cock??? This bitch is hung like a fucking horse!

You remind yourself of what she said earlier. Breathe. Relax. Actively relax. You repeat the mantra and will your body to obey. Deep breaths, no clenching. No clenching! It takes all the focus and willpower imaginable to not clench when Zoey's tip starts breaching. Fuuuck, that's a stretch.

"Nnnngg-gahh." sounds the suppressed grunt that eventually escapes you once her cockhead finally pops inside. You reactively clench down, immediately realize that makes it worse and will yourself to let go again. Holy shit, that is a LOT.

"All good?" asks Zoey, massaging the sides of your hips.

"G-good." you breathe, attempting to reassure both her and yourself.

"That's my girl." Zoey praises and gently massages your butt. "You know some say initial entry is the hardest part. So it might get easier from here."

"Great." you groan, eyes squeezed shut.

"Remember: we can stop any-"

"Do iiit. I wanted to have sex and we'll, ugh, gonna... have sex." you interrupt her, trying to sound brave.

"If you say so." Zoey chuckles and carefully, ever so slowly, pushes a tiny bit deeper. And indeed, since the head is in, the rest does slide in easier. Though feeling it burrow deeper into you is still such a bizarre experience. Also, her fingers are way, waaay shorter than her dick, meaning said dick very quickly reaches uncharted territory.

"Damn, been a bit since I deflowered an ass." jokes Zoey, not stopping her careful movements. Of course she would crash her soothing and helpful words with a remark like that. Never change, Zoey.

You don't really answer, too occupied with processing the many sensations right now as she slowly pushes deeper. It's a strange combination of uncomfortable, painful, pleasant and just odd. Her size feels absolutely absurd. Like, you obviously know Zoey's... dimensions. Like, 10 inches and perhaps even thicker than a can of coke is hard to forget. It's been months and you still haven't managed to deepthroat that thing. Still, your pussy has gotten used to the sheer size, partly because Zoey's just so damn good with it, but back there? This is insane.

"Still okay?" she checks, rubbing a hand up and down your spine.

"I'm goo-oohh." you attempt to reply but the end of your sentence trails off into a moan.

"You're goo? Okay, sure." smirks Zoey, giving your butt a playful slap.

"Bitch, yo- nnh, fuck..." you begin but trail off again. Another inch has entered.

"Heh, what a way to silence bratty back talk, huh?" she teases and you can practically hear her grin. That somehow got you wetter though. Like, this stuff might hurt and all but at the end of the day, your buff ass lover has her tree trunk cock up your ass. The more you struggle, the more obvious the power dynamic becomes. Wait, that IS really hot!

"Ungh, fuck you, just- ahh..." you tell her but - purposely - interrupt yourself with a moan. The more you kinkify this, the better this might actually become.

"Haha, aww~" coos Zoey and pets your butt. She might've taken the bait. She pushes deeper. It hurts, it's awkward, it creates a ton of pressure and it's weird. But at the same time, it makes you so strangely hyper-sensative. Like, you can feel your pussy practically pulsating with want. Vaginal stimulation would probably go crazy with this, holy shit. Well, you might not want to go inside your menstruating coochie, but nothing's keeping you from a little outer touch, right?

"Oh, fuck..." you whisper, your mouth hanging open. While Zoey continues her slow penetration, you bring a hand under yourself and slip it between your legs. Ohhh, yes, that is IT. Your first circle over your clit causes a shockwave of pleasure.

"Hehe, I like where this is going." Zoey comments and slaps your ass. Then she starts incorporating a few back and forth motions into her venture into your depths.

"Ooof, fffuck..." you moan, now with the side of your face pressed against the mattress. You continue rubbing, sending wave after wave of arousal through your system.

"Yeah, you are definitely a natural, haha." Zoey cackles behind you and spanks your other cheek.

"Mmmm-shit." you hiss and dig the fingernails of your free hand into the bedsheets. She's incredibly deep inside now and you still don't feel her abdomen press against your butt. Good god, she's big.

"You know, I'd ask if you're okay but I guess that's kinda obvious." Zoey teases and presses even further. So. Much. Dick. So. Much. Pressure. Your fingers are going rampant on your clit.

"God, just... oh, ffffff." is the most articulate thing you can come up with.

"Aw, you're so cute when you can't form full sentences." grins Zoey and finally, FINALLY, you can feel her abdomen pressing against your ass. Ten inches of cock - all in your ass.

"Man, I love this ass." sighs Zoey as she grabs hold of both your cheeks and starts slowly moving her hips back and forth. It feels like this bitch is outright stirring up your guts. And your pussy is on FIRE. You moan or groan or whatever the fuck and rub even harder. You have no idea how having a huge dick up your ass amplifies masturbation, but damn, is it ever. Imagine having something in your pussy as we- okay, let's not get ahead of ourselves.

"Mmm, that's right. Get off for me." purrs Zoey, squeezing your cheeks and thrusting a tad faster.

"F-fuuu-aah-uck." you croak, eyes squeezed shut and teeth clenched. Holy shit, this is happening fast!

"Damn, I should've done this much sooner." says Zoey and releases one of your asscheeks to smack it instead. Your fingers are going overdrive on your clit while your face gets pressed harder and harder into Zoey's pillow. It's so fucking weird! The pain and especially the pressure are still there but somehow both kind of elavate your clitoral stimulation so much! It's so god damn close to being too much but it barely doesn't cross the line. You slap the mattress with the hand that was clawing the sheets, just to release some of the tension.

"Good girl." groans Zoey and slaps your ass again. That cheek must be beet red by now. "Make a mess for me."

You don't answer. In fact, you fall completely silent. Your teeth are clenching, your lips pressed tight and every single muscle in your body tenses. You don't feel your orgasm building, you feel it erupting inside you. Zoey has made you cum countless times before and very quickly too, but this might be the quickest climax she's ever given you.

"FUCK!" is the only thing you manage to yell before a high-pitched whine escapes your throat. You collapse flat onto the mattress, not able to keep yourself propped up anymore. You don't move a single muscle and simply let the intense pleasure wash over you as Zoey de-escalates her thrusts into more gentle humping.

"There ya go." whispers Zoey, stroking her hands along your sides.

"Fuck, I'm- holy, ugh..." is the most coherent sentence you can come up with as you come down from your high.

"Damn, you really liked that, huh?" Zoey chuckles and stops her motions.

"Ye-yeah." you admit, taking a couple deep breaths. "Oh wow."

"Good." Zoey smiles and slowly pulls o-ow! Okay, okay, wow. You are SO overstimulated.

"Fuck." you curse, squirming a bit.

"I know, I know. Sorry." Zoey apologizes and continues to carefully extract herself. When her entire length is eventually pulled out, a really strange feeling of gaping emptiness is left behind. Well, you're likely literally gaped right now, so that makes sense. Regardless, Zoey then walks around the bed.

"You good?" she asks and squats down by your side, brushing some hair out of your face.

"Y-yeah." you respond and look at her. Her shoulder long hair is quite the mess and even still a little wet from her earlier shower.

"Good, I'll go get us some to clean up, alright?" she says and brushes her thumb over your cheek.

"Sure." you smile at her with unfocused eyes. When she stands back up, you can see her definitely still hard cock swinging around. What a fucking monster. And all of those ten inches were inside your ass. Holy shit.