Son for Hire: Part 14 (Patreon)

I wriggle and rub against her as I giggle.  “You think I’m sexyyy, you think I’m sexyyy!  Ha ha ha ha!”

She chuckles warmly as her cock presses up into me.  “Yes my boy, I do.  Come on now baby, stroke it faster.  I wanna see you cum nice and quick for me.”

“Yes Ma’am.”

My hand is a blur, stroking up and down aroused manhood in the way I did when I was going for maximum stimulation.

“Hurry baby.”  Her hands dig into my butt cheeks, massaging them and pulling them apart then pushing them together as she urges me on.  “Mom wants her nice warm cummies.  Hurry now.  Don’t make me wait baby, please?”

“I’m trying.”  I sigh.  “Ohhhh.”

Sitting upright she leans in to press her big breasts into my dick and stroking hand, it jiggles and jubbles as my rapid wrist slaps against it.  I turn it so the tip rubbed along the soft silky flesh.  My other hand continues to squeeze and fondle and my hips rock to the rhythm.

“Don’t hold back my boy.”

“I’m not.  Mmmmm.”  God, her tits looked and feel sooooo good.  All I could think about was blasting my jizz all over them.  It was all she was thinking too.

“Donald.”  Her tone was shifting from soft to stern, though not in a mean sort of way.  “Donald my dear, cum.  Cum for Mommy.”

“Uhhhhhnnnn.”  I stroke as fast as I could.  “I’m so close!”

“Donald!”  She says firmly.  “Cum…now.”

“Ohhhhhh.”  I give it my all.

She gives me another five seconds before she says.  “Stop.”

“Huh?”

“Stop Donald.”

My jerking hands stops and I still my body as well.  Through panting breaths I say.  “I’m almost there.”

She gives me a warm adoring smile.  I had fallen short of some expectation of hers but there was no hint of disappointment, only an odd sort of maternal pride.  “You did your best.  It’s not your fault.”

“What?”

“Come here.”  She pulls me in.  “Give me a hug.”

I hug her and she hugs me back, holding me in that special way only she could.  She strokes my hair and hums and kisses my body and…just…holds me.  Curling up into her I let out a most contented mewl.  “Mmmmm.”

“Ohhhh, so precious.”  She kisses my cheek and sits me up again, she then pats the ground beside her.  “Here now.  Get out of those clothes my boy.”

I look down at my twitching dick and her inviting tits confused as to why we stopped.  “But…”

“Donald.”  She warns.  “You listen now.”

“Yes Ma’am.”  I say.  

I was only too happy to obey.  This thing we had started I didn’t quite have a grip on yet but I knew already that it was some sort of BDSM connection.  She was my dominant and I her submissive, her the Mistress and I her chosen boy.  A Mistress completely unlike those leather clad crop wielding boss bitches that one thought about when the term dominatrix was mentioned, but she was a Mistress nonetheless.  She just…was.  And, despite my lack of experience in this stuff, my submission to her style of dominance came so easy.  It hadn’t been decided or outlined or talked about yet, but the power dynamic between us simply came as natural as our attraction to each other.

I lean to the side and come up off of her.  I could now easily see the shape of the enormous erection lurking beneath her skirt.  Doing as I was told I wriggle out my jeans, socks and undies and come to kneel where she had indicated.  Evelyn caresses her fingers down my bare chest, looking at me as if I were the most beautiful thing in the world.  Having someone look at me like that…it makes my heart feel so happy.  That look alone could have made me her slave, but there was so much more to Mom than just affectionate gazes.

“I tried.”  I whisper.

“I know baby, I know.”  She says.  “It’s not your fault baby.  You’re not used to having a woman to listen to.”  Lifting the hem of her skirt she exposes her thick lovely legs, her pale skin shaded by the black pantyhose she wore today.  She stops just short of her crotch.  “My poor boy, out there without a Mommy.”  With a gentle touch she guides me across her pillowy thighs.  My legs on one side of her legs and my arms supporting me on the other I find myself on my hands and knees with her legs beneath me.  “Out there having to be so strong and brave and independent.  Nobody there to look after him.”  She continues to guide me, making me lower my body down on top of her legs.  With a single finger she steers my boner so that it slipped down between her silky stockinged thighs.  Ohhh, that felt nice!  “You’re not out there now baby.  You are here, with me.  Leave all of that nasty stress and worry out there.  Okay baby boy?”

Haltingly I nod.

She runs a hand up my back to direct me to relax my body down onto the carpeted floor.  I do so, turning my head toward her I rest my cheek down and allow my body to relax.  “Good boy.”  She whispers.  Then she runs her other hands down my legs, ensuring these two were relaxed and comfortable.  “Spread them wider baby.”  Holding my inner thigh she pulls my near leg in, I move to her touch while also spreading my other the same amount until there is about a hands breadth between my two legs.  “Good boyyyy.”  She draws her fingers up the tender flesh of my inner thigh causing shivers to tingle through my body.

I can’t help but feel self conscious.  Here I was, a grown man, being put over my ‘Mom’s’ knee in the most compromising of ways.  But Evelyn just had this way about her, this way of making it all feel right and natural and wholesome.

“I’ll cum better next time.”  I say, blushing even as I utter the words.

“You did your best.  It’s not your fault.  They have you all bothered.  All those nasty skanks last night and all those stupid worries Diane has you thinking about has you all distracted.  I understand.”  She tenderly begins to rub my tush in a slow circle.  “But when I say cum baby, you need to listen.  Good boys listen to their Mom, no matter what.  Okay?”

“Okay.”

“I’m going to spank you now.”

“Yes Ma’am.”

“A boy needs a firm hand.”

“Yes Ma’am.”

“A young man needs discipline.  Do you understand?”

“I do, I do Mom.  I need it.”  I wiggle my butt and quickly discover that the slightest motion brought with it an incredible pleasure as my dick, pinned tightly between her plump nylon covered thighs, lit up with delight.

As if hypnotized by it her hazel eyes stare at my bare bottom as her hand rubs it lightly in a circular motion, slowly warming it beneath her soft palm.  My body melts for her, I hadn’t felt this loose since that warm bath she gave me.  I gaze up at her and await whatever punishment I was due.  With her left hand she reaches down and takes mine, holding it supportively.  I grip it firmly.  Slowly she raises her right hand, the one that had been rubbing my bottom.  I close my eyes and ready myself physically and mentally.  My own Mom had spanked me, really spanked me, with hand or belt or slotted wooden spoon and I knew this might trigger that old trauma.  But I steel myself for what was to come, determined not to ruin this incredible moment with more tears.  If Mom wanted to spank her boy I wasn’t going to stop her.  Her holding my hand gave me something to hold onto, both literally and emotionally.  There is a long quiet moment and then…

Pap.

I open my eyes again.  That was a spank?  It was barely more than a playful pat to my right buttock.  She raises her hand again…then brings it down swiftly.

Pap.

Same thing, this time to the other side.  With both cheeks struck Mom then starts to rub my booty again, as if soothing away the sting.  Was she still warming me up?  As I look up into her face, focused with adoring concentration, I realize that this really was my spanking.  This woman, this wonderful woman, didn’t have a genuinely violent bone in her body.

“You okay baby?”  She asks softly as she strokes my butt and grips my hand.

I nod.

“This won’t take long.”

I nod again.  Bringing her hand to my face I nuzzle into it and close my eyes.

Pap.  Pap.  Pap.  Pap.

My smile widens with each carefully controlled strike.  Her power wasn’t enough to make a baby cry, it almost tickled.  She rubs my tushy again, making sure it was feeling good.

“Mmmm.”  I moan happily as I squirm and feel that silky sheer slide around my penis.

Pap.  Pap.  Pap.  Pap.

Her soft palm claps into my rear repeatedly.  Never harder, never softer, and spaced out at a predictable interval.  While nowhere near hard enough to hurt it does jostle me every so slightly, meaning it made my dick slide a little.  My bum happy, my dick happy, I lay there a very happy boy.

“Ohhmmmm.”

“More?”  She asks as she pets my ass.

“Yes pleeease.”

Pap.  Pap.  Pap.  Pap.

“Mmmm.”  My hips start to rock.  I was already close to cumming before this started and this spanking was near to finishing the job.  “That feels goooood.”

Pap.  Pap.  Pap.  Pap.

Instead of rubbing my behind this time she slides her hand down and instead rubs my tight balls in just the same tender way.  “You gonna cum for me now?”

“Yes please!”

“Okay baby.”  With just two fingers she starts patting my nuts in a miniature version of the spanks she’d just given me.  “A nice big one for Mommy?”

“Yeesssss.”  My hips are thrusting, my dick gliding through the squeezing soft satiny space between her thighs.

“Okay, cum for me.”  She massages my nuts.  “Give Mommy a nice big load now.”

“OHHHHHHHhhhhhhhhh!”

“Ohhh yes!”  She sighs as she watches my ass flex as I thrust down between her legs and blow my wad.  She continues to gently rub my tender throbbing nuts as they shoot their load.   “Atta boyyy!  Gooood boyyyy!”

“Ohhhhhhhh.”  I pule softly.  My whole body shudders as the powerful orgasm gradually eases away.  “Hohhhh.”

“Allll done.”  She says happily, petting my scrotum like a beloved pet.  “You did so good!  I feel your warm messy load between my legs.  Mmmm.  Good boy!  Such a strong, virile, powerful young man.  You took your spanking so well, you listened to Mom so good.  My good, good boy.”

“Hnnngh.  Are you for real?”  I whimper blissfully, more a statement of disbelief than an actual question.  “Ohhhhh.”