Son for Hire: Chapter 23 (Patreon)

Evelyn pulls my near leg outward and orders with that touch of authority she so easily to put into her warm tone.  “Spread open for me baby”  I do as she commanded.  Spreading my legs so that one went up onto the back and one down onto the floor.  She slowly shakes her head.  “Mmm mmm.  That will not do my boy.  Show me that sweet little ass of yours.  Don’t be shy.”  

I hesitate just a second, I was not accustomed to exposing myself so completely.  One look at Mom though calms my worries.  I bring my knees all the way up so that my thighs touched my flanks.  I then hold them there with my hands.  In this position my anus was completely open to the air.  It felt dirty but Evelyn’s smile made it feel like the most natural thing in the world.  “Like this?”

“Yes!”  She says warmly.  “Hold your legs there.  Give yourself a nice big hug.”

Looping my arms around my legs I do as I’m told.  My feet I splay to the sides as best I can so that I could see my beautiful Mistress.  “Yes Ma’am.”

“Good boy.”  She says as she kneels closer and slowly brings the lubed finger lower.  “Can you reach your special little guy?”

“My…?  Oh.”  I wriggle a bit and I am indeed able to snake a hand down so that my fingers and thumb at least touched the tip of my dick.  “Yes Ma’am.”

“Go ahead and stroke it she says.”  At just that moment…contact is made.

“Oh!”  I flinch.

“You can cum whenever you want.”  She says as verrrry tenderly she rubs the lube against my hole in slow small circles.  “You have my permission.”

I gasp and nod.  For a few seconds I cannot move but eventually I let my body relax and I begin to stroke the tip of my dick as best as I am able to.

“There you go.”  The finger at my anus continues its lazy circles.  “You’re doing so good.”

Moving her weight over me she looms closer, leaving her rubbing finger behind to do its work.  Leaning in over my legs she pulls open the left side of her robe, her massive fat titty spills out.  Holding it in her hand she guides it to my mouth, only the large size and weight of her teat allowed it to hang low enough for my lips to reach it…but reach it they do.  Eagerly I latch to her fresh pink nipple and begin to nurse, just as I had done with the other.

“Ohhhhhh God damn!”  She sighs and her eyes roll.  “You can’t know what that does to me.”  She looks back down into my eyes happily staring back at her.  “Or maybe you do.”  She squeezes and strokes her breast as if trying to milk it into my mouth.  I could see how keenly she wished to feed me with her own body.  I do everything I can to mimic feeding, pretending that I am suckling life giving milk from her tit.  Her body relaxes into me.  “Just like that.  Mmmm.”

The position was a bit awkward but I really liked the feeling of having her weight leaning into me from above.  It brought with it a heady feeling of submission and inferiority, especially since her big dick had slipped from the crack of her robe to press into my leg.  I liked her being on top of me, I liked that she was bigger than me, I liked how she was touching me.  I was HER boy and that made me feel good.

“Hmmm.”  I let out a suckling moan into her breast, my hips unconsciously tilting up to offer my ass to her.

“Breathe.”  She whispers as her finger stops and centers itself.  “Big deep breaths.”

Through only my nostrils, my mouth too busy on her nip, I take in slow deep breaths.  “Mmmm.”  I coo submissively as I feel the pressure at my back door gradually increase.  “Hmmm!”

“Shhhhh.”  She smiles.  “It’s okay.  It’s okay.  Don’t be scared.  I promise baby, it’ll just hurt a little.”

Holding my gaze in hers she enters me.

“Hmmmmmm!”  

“Good boyyyyy!  Ohhhhh good boyyyyy!”  She praises me as she slides her finger inside of my ass.  “My brave prince.”

“Hmmmmm.”  I mewl at the unfamiliar sensation.  She was right when she said there would be a pinch.  It did hurt a little, mostly because my bum was trying to reject it.

“Breathe baby.”  She whispers.  Freeing her hand from her breast she uses it to pet my hair and soothe my virgin fears.  “Keep stroking yourself.  Concentrate on the good feelings.  Relax.”

I go from holding my breath to panting quickly through my nose.  She is so gentle with me though, holding her finger in me just to let me feel it and adapt to it without any extra motion.  It was weird feeling something down there, feeling something inside of me in general, but it really wasn’t that bad.  As promised it just hurt a little.  And even that was quickly fading.

“Mmmm.”  I hum, allowing the easing feeling come through in my voice.  Still we gaze into each other and with each passing second our bond grows stronger.

“You are so beautifulllll.”  She strokes my face.  “Mommy loves youuuu.”

“Mmmmmm!”  What was it about this woman that made me continually want to cry!?  I felt like one great raw nerve in her presence, sensitive and open to every emotion.

“I’m going to move my finger now, okay?  This might be the worst part.  Okay baby?”

I nod and nuzzle into her breast for additional security and comfort.  Again she was right.  As her finger glides out then presses back in again my sphincter spasms and clenches to fight her to my sharp discomfort.  “Ngh!”

“Shh, shh, shh, shhhh.  I’m right here.”

She lets her finger rest a few seconds then does it again and again and then again.  “Hnngh.”

“That’s it.  I can feel you relaxing.  Good boy.  Relaaax.”

In and out her finger begins moving in slow but steady smooth thrusts.  Whether it was fatigue or by my will my butt’s involuntary resistance eases, stroke by stroke.  It is not long before she is fingering me with no struggle at all, the thick slick lube doing its job admirably.

“There it is.”  She grins proudly.  “That’s not so bad, is it?”

“Mmm mmm”  I shake my head.

“Whose my brave boy?”

“Mmmm!”  I beam.

“That’s right baby, you are.”  Her finger goes a little faster and a little deeper, all of it now inside of me when she pushes in.

“Keep stroking your dick.”  She says.  “Just think about the good feelings.  Just let yourself go with what your body is telling you.”

“Mmmm.”  I am suckling faster and hard now as my brain instinctively timed the suckles to her probing finger and my rubbing hand.  It really was starting to feel good.  All of it.  The sexual feelings from my playing with myself mixing up and melding with the increasingly nice feeling of having my bum fingered, and the soothing nursing and gazing wrapping it all in a extra special feeling of love.  As I stare into I start to pretend that this was her penis inside of me.  It was just a finger, her cock orders of magnitude larger, but for right now I dream it she was fucking me properly.  Precum oozes from my dick like I’d never experienced before as she press into its root from the inside.  Oh my goodness that was nice!  Everything just felt better and better and better.  “Hmmmmmm.”

She is absolutely glowing as she watches me give myself over to the bliss.  “That’s your prostate sweetie.”

“Hnnngh.”

“Feels nice, doesn’t it?”

“Mmm.”  I confirm.

“Feels nice for me too.”  She says.  “Ohhh.  Your tight little asshole gripping my finger so good.  I can imagine other parts of me inside of you.”  She licks her lips and swallows.  “Mmmm.  You feel better than Alan ever did.”

“Mmmmm!”  I suckle even harder and my hips start to rock to move with her as suddenly I found myself wanting more and I wanting harder.

She gasps, her face flinching with growing pleasure but also pain.  “Easy baby, go easy on me.  You’re a strong boy, be gentle with Mommy.  Okay?”

“Hmmmmmm.”  I moan in total and complete submission as I ease up on the sucking and lapping though keep my sucking pulls firm.

“Hahhh.”  He smiles again.  “Yessss, just like that.  I like that you know how to touch me.  I like it when you’re gentle with me.”

“Hmmmmm!”

“Look at you.”  She giggles.  “Your blush is the cutest thing I’ve ever seen.  Getting close already?”

“Mmm hmm.”  I nod.

“Who is my big brave sexy man?”

“Hnngh!”

“That’s right!  You are.”  She gently pinches my nose.  “You are Donald.”

“Ohhmmmm.”

“Listen to me now.  I want you to stop just before you cum.  Okay?  Don’t worry though, I’ll take you the rest of the way.”

“Hmmmm!”

Bringing her right knee up she pins my left ankle against the back of the sofa causing her junk to shift over to press against my balls.  Her right arm is her anchor, her hooked finger gliding smoothly in and out.  “You are taking it so good.  That’s it baby.  I see how close you are.”

“Hnnngh!  Hnnngh!”  I was struggling to maintain my suckle as air hisses in and out of my nostrils due the demands of my rising orgasm.  I stop my stroking and just move to rhythm of Evelyn’s anal fingering.  My body desperate tries to hump back into her finger but in my current position I could barely move.  “Hnnngh!”

Her eyes are intense as they gaze down into me powerfully.  “That’s it.  Focus on the good feelings.  Mommy is fucking you baby, she’s fucking you so good.”

“Hahhhh!”  My mouth breaks its seal and I let out a mewling whine.  “I’m so close!”

“I know baby.  Be patient.  Don’t touch yourself now.”

Urgently I latch back onto and suckle like crazy as my climax grew in this infuriating yet intoxicating gradual way.  Had I kept stroking I would have nutted by now, but as it was I just rode the edge.  My whole body is on fire, my ass glows with a new kind of delight.  I wanted more!  I needed it harder!  That one little finger that had stung on the way in now seemed wholly inadequate.  But Evelyn knew what she was doing.  She knew JUST how to touch me.  With strong steady thrusts and an unerring rub against my prostate she has me a quivering jelly.

“Hnnnnngh!”

“So close.  Just give in to it.”  She urges me.  “Think about cumming…and you will.  Go ahead my boy, cum for Mommy.  Show me good you can cum.”

My quivering becomes full on trembling.  I am nearly out of my mind in this all consuming pre-orgasmic high when, as if by magic, I cum.  It wasn’t what I was used to.  Normally my orgasms are a massive spiking burst of sexual rapture, this one sort of swelled and swelled…then all let go at once in a rushing flood that consumed my entire nether region.  The only noise is my rapid shallow breaths.  Hot wetness spreads over my tummy from the thick gobs of jizm burbling from my dick.  I thrust up against her as I cum and cum and cum, far longer than I’d ever cum before.  

All the while my red-headed angel watches me and pets my sweaty forehead.  “Ohhh, good boy.  You did it!  Your very first time.  I feel you cumming baby.  I feel you!  Throbbing around my finger.  Good boy!”

“Hnnnnnngh…”  I find my voice at last only to let out the most pathetic whimpering whine I’d ever heard.

It wasn’t pathetic to her though.  For a Domme like her, hearing a man like me make that sound was the most beautiful of music.  “I am so proud of youuuu.”