A Simple Life: Chapter 104 (Patreon)

I lay with my legs high and wide, my wrists bound to my ankles, my nylons ripped and my panties pulled to the side, with Winona kneeling over me and filling the space between my legs.  At last.  The time had come.  Leaning down she kisses me once more then pulls slowly away.  Her long tan cock draws back across my cage and balls until it drops out of view.  She takes a hold of her thick dick then shimmies closer to me until I feel her bulky knob touch my entrance.

“Mmm!”  I flinch, tightening my anus from giddy anticipation, then force myself to relax again.  “Ohh!”

She smiles and gives a wink while rubbing her swollen glans up and down over my hole.  Ohhh it felt good!  It felt so good.  Through my tender rectum I could feel the shape and firmness of her fat knob.  One hand securing her shaft she takes a grip of my handy corset to take control of my body.  We were both learning about how this wonderful harness didn’t just bind but gave her handles with which to move me and control me.

Her gaze delving deep into my soul she slowly, carefully, begins to leans her weight into me.  Emotionally, physically, spiritually I open myself and let her enter me.

“Hohhh.”  I sigh as my lubed and aroused hole widens to allow Winona’s penis in.  I shift my grip on my ankles and tighten them as down below I focus on easing into this.  “Ohhhhh.”  With another exhale I relax more as bit by bit she makes progress.  We were still dealing with the first inch her and already I could feel that this was going to be something different.  My entrance was already as wide as it ever got with Eddie but the full bulk of her cock was still pressing at the door.  “Mmm!”  I wince as with another quarter inch entry she begins to stretch me past where I’d gone before.  When she stops in concern, as I knew she would, I give her a reassuring smile.  “You’re thick.”

“If I’m too big…”

“No.”  I say.  “No.  I just need to adjust.”

“Baby, it’s okay if…”

“No.”  I whisper.  “P-Please don’t stop.”

She caresses my cheek, her long fingers tracing down my delicate jaw, then gives my chin a soft pinch.  “Use your safewords.”

“Hmmm.”  I grin.  “Yes Ma’am.”

Watching me even more closely now, if that was even possible, she brings her hand around to cup the back of my neck…and pushes forward.  As her cock pushes into my tight hole her expression melts into one of pure ecstasy, her eyes rolling back from the good feelings.  “Oh fuck!”

“Oh!”  I gasp, my eyes steadily widening at the same rate as my butt until…  “OHH!”  The moment that I’m stretched to her full glorious girth there was nothing to stop three inches of her from rushing in at once.  “OH GOD!”  My arms and legs clamp onto her to curb her entry.  “WAIT!  WAIT!  MMM!”  Holy moly!  I knew she was thick but seeing it and feeling it were two different things entirely.  I was plenty lubed and well warmed up, it was purely her size causing the issue.  I had been way too cocky in my bottoming ability and her anus filling girth was humbling me in a hurry.  Monsters were to be treated with caution, even friendly ones.  I’d never felt anything like this, not even when I lost my cherry.  Try as I might I just couldn’t relax myself any further.  My hole was at its absolute limit.  And as my bum reflexively bears down to try to force the intruder out it only made things worse.  From my taut lips escapes a whimper.  “Owie.”

“Owie?”  Her eyes snap back to look at me.  “Sprout?”

“Mmmm!  Yellowww.”  I whine, my eyes apologetic for making her pause.  “Fuck…f-f-fuck you’re b-big!  Ohhhh!  You’re r-really b-big Daddy.”

“Too big.”  I watch in horror as her mood shifts and she goes to pull out.

“Don’t move!”  I cry before settling my voice again.  "D-Don't m-move."  As much of a strain as this was her pulling out right now to try again would have been torture.  If this was anybody else at any other time I would have wanted to stop and wait for another time.  But not with her.  Not tonight.  Tonight was the night.  Our night.  If this was going to happen I wanted it to happen now.  “Please.  Just…just let me…mmmm.”  I take a deep breath.  “J-Just let me…acclimatize.”

“Baby.  It’s okay.”  She says softly.  “Kayla wasn’t able to take me back door either.  It’s okay.  We have so many other things we can do.”  Her voice is so warm, so soothing, so understanding.  “It’s okay Avery.”

One…two…three long, slow breaths.  And with each breath the burning, pinching ring of discomfort eased just a little.  The pain was neither sharp nor intense, there were no obvious red flags that something was wrong, it was more of an ache that was gradually fading.  And like a fog parting as the ache faded I could just begin to make out the sunlit fields of pleasure waiting for me beyond.  This was a challenge but this incredible feeling of fullness wasn’t all bad.  “Hahhhh.”

“I don’t want to hurt you.”  She whispers.

After another calming breath I say.  “It’s getting better.”  Another breath.  “Mmmmm.”  I smile.  “It’s like m-my first time all over again.”

“Oh Avery.”

“Hahhh.  It’s g-getting better.”  I say honestly.  “I’m okay.”  Another breath and a swallow.  “Wow.  Green.  J-Just be gentle, okay?”  Being very careful not to move her hips she unclips my left cuff and then my right.  “Wh-What are you doing?”

Taking my legs she pulls them around to wrap them behind her.  Taking my hands she brings them to rest on her upper arms.  She leans down over, the minor motion in my butt enough to make me squeak, and plants her hands on either side of my shoulders as she looks down into my eyes.  “Guide me.”

Her loving gaze enough to make me fall for her all over again I give a slow nod.  She nods back and we continue.

“Nnnngh!”  I groan as she oh so gingerly guides another beefy inch into me and pauses.  “Oh…gah!”  I huff.  “You’re soooo big.”  My hands grip tighter on her arms as my legs pull at her to signal that I was ready for more.  “MMMNGH!”  My back arches as she FILLS me to the brim.

“Ohhh shit that’s good.”  Winona growls.  “Talk to me sweetie.”

“Ohhhhh.”  I moan.  “H-H-How much more?”

She glances down.  “Four more inches.”

“Four!?”  I felt ready to burst and she was barely more than halfway!  “Ohhhhh my God!”

Sparing a hand to play with my titty then my clitty and balls she says.  “There’s no hurry for the rest.”  After a moment she pulls a couple of inches back out through my straining rectum.  “This is lots to work with.”

“Ohhhhh!”

“Fuuuck!”  She sighs as glides those two inches smoothly back in again.  As she waits for me adapt again she bring her fingers, wet by the precum oozing from the slit in my cage, to her mouth to lick them clean.  “You taste good baby girl.  Mmmm.  You FEEL good.”  With that she flexes her huge erection.

“OHHHH!”  Shifting with my feelings my moans were becoming more lusty.  This fullness!  This fullness!!!  OH WOW!  “MMMMM!”

“You are so beautiful.”  Going no deeper but moving more freely she begins to make love to me.

“HMMM!”  Again my back arches and my fingers claw at her shoulders as she stuffs my ass.  With each careful thrust she felt better and easier.  “Hohhhh!”  On one of the thrusts forward I invite her deeper with a subtle tug of my legs.  “NNNNGHHHHH!”  She lets me have two more full inches of her to blow right past where any finger, toy, or Eddie had ever gone before and into parts unclaimed.  I loved the idea of that part of me being hers and hers alone, almost as much as I loved this heady feeling of taking it deep.  “HMMMM!”

Her hazel eyes keenly watching me despite her own sexual bliss she again pauses to allow me to adapt.  She kisses me and kisses me again.  “You’re doing so good baby girl.”

“Mmmmm!”  I hum as my body relaxes.  “Ohhhhhh!”

Feeling my rhythm and energy start to meld with hers she picks up the pace.  “That’s it.  Ohhhh shit that’s good.  Ohhhh Avery!”

I wanted to say something back but the way her looong dick slid through my entrance, the way it touched me so deep, and the way it’s fat girth filled me and rubbed along my prostate had me trembling and sputtering gibberish.  “Pbbbfff….OHHHHHHH!  DEEEEEP!  NNNGH!”

“Big ones aren’t so bad, huh?”

“Ohhhhhhh!”  My high, warbling lilt fills the room.  “Winonaaa!”

She chuckles.  “I’ll take that as a yes.”

I’d gone this far.  There was no stopping now.  Close as we were my singular obsession was to feel her as deep as I could have her.  Breathing heavy I grab at her sides as my legs tighten around her.  Reading me well on her next stroke back she pauses…grins…then in one silky stroke drives ALLLL the way inside.

As her big balls reach my ass and she grinds into my super stretched hole right to the hilt they must have heard my wail in Haven Point.  “OHHHHHHH!!!”

Chapter 105