A Simple Life: Chapter 16 (Patreon)

Beyond blinking I don’t move one single muscle.  I worried that, like dropping a pebble into still water, it would take just the smallest of disturbances to ruin what was happening right now.  Even my breathing, taken in long and slow breaths, I try to make as minimal as possible.  Winona seemed oblivious to the effect she was having on me as she happily pulled the different pigments and instruments from her cosmetics bag.  But for me there was a lot going on right now.

This kind, beautiful, wonderful woman with the easy laugh had invited me into her home, fed me, and guided me into her beloved hobby without ever teasing me or making me feel bad about my silliness and stuttering.  She also took control of me and manhandled me in ways that had only happened to me in my hottest and sweatiest of wet dreams.  Unlike the brothers and bullies of my youth she over powered me to control, not to hurt or humiliate.  And it made ALL the difference.  It was the main reason for the raging boner hidden beneath the pillow.  And finally, and most significantly, she was…dressing me like a girl.  Something I’d had urges to do since my early teens but had been bullied out of me by my mom, my brothers, my sister, and, hell…everybody!  It’s not that I was a girl or even wanted to be a girl, it was more the freedom to play with the idea that had my heart so lifted.  And now here it was happening.  It was happening and I had no say in the matter, which meant I couldn’t chicken out.

Quietly, placidly, I lay staring up the larger woman crushing on her like I hadn’t since my first puppy love.  Taking a bit of creamy white moisturizer on the tips of her fingers she swipes it across me cheeks and forehead then begin to work it gently rub it into my skin.

“What I wouldn’t do for pores like yours.”

Her fingers felt so warm and nice as they ran across my face.  After the moisturizer is well worked in and my skin ready there comes another paste, the primer I think.  This too she rubs all across my face to form a base layer upon which she would paint my feminine mask.

“Your skin tone’s lighter than mine.”  She says a she smooths it all out.  “But no worries, I can work with this.”

Sitting up tall she closes up a couple of things and opens up others.  After daubing a little cool goo on my cheeks, chin and forehead she the uses a wide brush to paint it out evenly.  The bristles of the soft brush make me giggle.

She smiles and says.  “Stay still you.  And stop smiling.  You’re making dimples.”  This makes me giggle more but soon I force myself to hold a neutral expression.  She boops my nose with the tip of her brush.  “Good girl.”

Something new is then dabbed very carefully along the ultra-tender flesh below my lower lashes and with her pinky she oh so attentively spreads it out.  I just lay and stare up at her bewitched by her focused hazel eyes.  Every so often she would glance up to make eye contact and hold it for a few seconds as I absolutely melt.  She moves on to the next thing.  Using a big fluffy brush she pats it in some powder.

“Close your eyes Sprout.”  I do so and soon I feel the supple bristles caressing my skin.  “So Kayla says you’re bi.”

I swallow.  “Yeah.”

“Ever been with a guy before?”

“I’ve…fooled around a little.”

“Nothing serious?”

“I-I tried once but…it didn’t work out.”  That ill-fated relationship had been with a guy Kayla hooked me up with named Eddie.  We gave it a go for a few weeks but quickly ran into the classic problem of both being bottoms.  Eddie dropped me pretty quick once he realized we weren’t compatible.

“Mmm.”  Her weight shifts.  There is a click of something being closed and the rustle of other things being readied.  This was turning into quite the process!  “Do you like getting pegged?”

I open my eyes.  “Wh-What?”

“Pegged.”  She says as casually as anything as she swirls yet another brush into some blush.  “Kayla ever bend you over?”

I shake my head no.

“A booty like yours?  I don’t know how she could resist.”  She chuckles, then pauses.  “Does talking about this make you uncomfortable?”

I shake my head no again.  The only thing uncomfortable right now was the aching boner in my pants.  She wanted to peg me!?

“Good.”  She swirls the blush on the apple of my left cheek then fades it out straight back toward my temple.  “Here’s the thing Avery.  The thing you need to know about me.”  She refreshes the brush and switches to begin working on the right side.  “I’ve got a penis.”

As if on cue the mellow country song that had been playing fades to an end and the wind and rain outside hits a lull leaving the room in momentary silence.  I look up at her wondering what kind of joke she was trying to tell me right now.  After a long tense quiet the next song plays and the storm howls once more.

“What?”

Finishing up the blush she sits up.  “I was hoping Kayla would tell you.  Or least get you ready.”

“What…what do you mean p-penis?”

“A dick.  A cock.  A pecker.”  She says as she readies a slender pencil like brush, holding it like a pencil.  Leaning down, her left arm across my chest, she concentrates as she brushes the tool through my narrow eyebrows.  “My elders say that I am winkte, a two-spirit.”

“Two-spirit?”

“I don’t know if it’s a mutation or a condition or what but, yeah.  I’m kinda special that way.”  With a finger she smooths out my brow.  “If you could keep this just between us I’d appreciate it.”

“Why…are you telling me?”

Moving to my other brow she says.  “I could be wrong but…I think we’re getting along.”

“We are.”  I whisper.

“I think you’re cool Avery.”  She takes a long, deep breath then says.  “I think you’re really, really,…really, really cool.”

“I-I think you are too!”

Her smile warms my heart.  “Yeah.  Well, I thought I’d just get that out there.”  Her hand stops and she looks into my eyes.  “I don’t want to scare you away Avery.”

I stare up into her eyes utterly entranced yet still struggling with what she had said.  Was she messing with me?  Was this a part of her fantasy?  A part of her character?  Why would she say that?  She looked so earnest and so…vulnerable.

“If you don’t believe me…”

“I believe you.”  I hear my own voice say softly.  “I-I’m not…afraid.”

She lets out a sigh and her body noticeably relaxes.  Tilting her head she says in a gentle yet cheerful tone.  “Good.”  Pushing her glasses back up to the top of her nose and bringing a palate of eyeshadow colors from the bed up onto my chest she says.  “Close your eyes.”  I do so.  “Green with gold highlights work for you?  I thought that would look pretty elvish.”

“Elvish?  Oh, right.  Y-Yeah.  Sounds good.”

She falls quiet as she works on my eyes.  Brushing, daubing, and dabbing from my brow down to the bottom of the socket and from inner corner to the outer.  I smile when I feel the pencil like instrument she was running along the top and bottom of the seam of my lids give me that cute little flare at the corners like I’d seen so many women wear.

“You look beautiful.”  She says.  “Just wait until you see her.”

Opening my eyes I grin a beaming, bashful grin.

“Gorgeous.”  She says.  Next comes the weird contraption that curls my lashes followed my mascara.  I adored how careful and attentive she was as she made me look like my elf maiden character.  Somehow, someway, Winona had just dropped the mother of all bombs by telling me about her private parts and yet…it didn’t matter.  It didn’t matter one tiny bit.  I didn’t give a damn what was between her legs.  I mean…it excited me, sure.  But deep down it just didn’t matter.  She literally could have turned into a slavering werewolf on top of me and I would have just lay here continuing to soak up her attention.  I don’t know how she managed that.  Maybe…maybe she was right.  Maybe magic was real.

With a deft touch she applies highlighter at my inner eyes, down my slender nose, across my fine cheek bones, and around my brows.  Then, at last, she finishes me off with a pretty pink lip gloss.  After a close once over she gives a nod and sits up looking rather proud of the transformation she’d performed.

“Wow.”  She says as she clicks the cases closed and returns the caps to other things.  “Wow!  Now that is a 100 Charm.”

“Wh-what’s it look like?”

“A whole new you.”

I giggle and for the first time begin to squirm impatiently.  “C-C-Can I see?”

“You got it Sprout.”  Putting the cosmetics away she tosses the bag to the side.  She gets up off of me and removes the pillow, a lingering of her eyes and a smirk at the side of her mouth telling me that my secret erection was not so secret anymore.  She doesn’t say a word though.  Pulling me to my feet she gives me back my ‘spell book’ and straightens everything out.  “Close your eyes.”  Needless to say I do so.  Taking my hand in hers as if I were royalty she leads me across the room toward the washroom.  “Walk like a lady.  That’s it.  That’s it!  Good girl.”

As I stride with a feminine flair, Winona holding my hand and guiding my steps, I am near ready to leap out of my skin with anticipation.  Into the washroom we go and I hear the click of the light come on.  She takes me by the shoulders and turns me to face the mirror above the sink.  Standing behind me she leans down over my shoulder and whispers into my ear.  “Okay Avery.  Open your eyes.”

Chapter 17