Son for Hire: Chapter 53

Her hazel eyes roll and Evelyn lets out a long happy sigh as her climax fades.  “Ohhh God.”  She whispers.

“Was it a good one?”  I ask.

“Yes baby, it was a good one.”  She smiles, her gorgeous face aglow with good feelings.  “I think I quite like having my own camboy.”

I giggle.

She takes another deep breath and composes herself.  The hand on her breast stops rubbing.  The other one comes back into sight, a sheen of moisture on the inside of the fingers, and she reaches to the side the wipe it with a tissue.  She then pulls the shoulder straps of her nightie back up to cover herself.  As much as I hated to see her boobs covered I understood the risk she was taking.  Her husband might walk in at any moment and while he wouldn’t be able to see the screen of her phone if he saw his wife with her tits out suspicions would surely be raised.  Besides, I was her boy.  I was the one giving the show.  She could enjoy me anyway she wished.  

I continue to slowly finger my ass with two fingers.  The sting was long gone and it was only feeling good now, the steady dribble of precum leaking onto my belly was evidence of that.  Subtle slurping noises accompany my penetrating fingers.  I was as loose and as warmed up as I was going to get and I was eager for more.  My shoulders propped up on the blankets and pillows, my head up to look down toward the screen, my legs splayed wide I await my next instruction.

“Okay my prince.”  She says as she picks up her phone to bring it closer to her face.  “Now I can focus.”

“Yes Ma’am.”

Her gaze takes me in, paying particular attention to my probing fingers.  “Does that feel good baby?”

“Yes Ma’am.  So good.”  I huff.  “Really, really, really good.”

“Mmm, I can see.  Damn you are looking so sexy baby.”

“Ohhh Mom.  I wanna get fucked so bad.”  I trill.  “I want to feel you inside of me.”

“Oh my sweet boy.”  She beams.  “It will take time for you to be ready for that.”

I pout.  “If you say so.”

“I do say so.”  She says firmly.  “Mommy’s very big.  I’ll need to see you take a whole hand before I know you can take me without me hurting you.”

“A…whole hand?”

“Yes my boy.”

“You want…to fist me?”

Her face scrunches.  “That’s a crude way of saying it, but yes.”  She says.  “Does that scare you?”

“No Ma’am.”  I say with false bravado.  

She leans in with a prescient maternal stare, seeing right through my fib like it were fresh water.

“Maybe a little.”  I confess.  When I wasn’t looking at her penis it was easy to forget just how huge it actually was.  She wasn’t wrong, if I couldn’t take a hand and wrist I probably couldn’t take her.  But the idea of being fisted was so…raunchy.

“We stop when you want.”  She reminds me.  “You only do what feels good.”

“I’ll do anything for you!  I’ll do it!”

“Shhhh.  No baby.  Not like that.  You are my soft boy.  You are my prince.  If we do it, we do it for you.”

“Mum…”

“Shhh.  If we are able to make love in that way it would be wonderful.  If not, it will still be wonderful.  Let’s keep our expectations realistic.”

“I want to make love to you.”  I plead.  “I want you in meee!”

“Shhhh.”  She soothes.  “You have my gift?”

“Yes Ma’am.”  I reach with my free hand and plop the cock atop my chest.

“Good boy.  Why don’t you get that nice dick all lubed up for me.”

I slip my fingers out and find the lube.  Impatient as I am I end up spurting out way too much onto the silicone toy.  Smearing it all up and down the knob and shaft the excess lubricant flows down over my chest.  With my other hand I rub the glistening goo all over my chest and stomach until my body gleams in the overhead light.  I lube up my own dick as well, giving it a few long strokes.

Evelyn is delighted by it all, she laughs and smiles and shakes her head.  “Boys.  So messy.”

I giggle again.

“Alright silly.  Enough playing around.”  She says.  “Time to fuck that cute ass.”

“Eeee!”  I grip the toy and try to lift it.  Slippery as grease it squirts from my hand to tumbled down over my belly and onto the floor.  Mom laughs more as I scramble to find the super slick dick and get a proper grip on it.  Her laughter makes me laugh and I ham it up a bit just to keep the jubilant feelings high.  At last I have it by the base and down between my legs.  Knowing it was about to be inside of me I look at its shiny length and, though smaller than me, it suddenly didn’t look so little.  “Oh boy.”

“I think you are going to like this.”  She tells me.  “Just be gentle baby.  You stop if anything feels bad, okay?”

“Yes Ma’am.”

“Alright.”  Her face is right up to the screen now as she gets as close as look as she can.  “Put it against your tush.”

With one slippery hand I pull a butt cheek wide as the other probes to find my juicy entrance.  The smaller picture on the screen acts as mirror to help me.  Soon I feel the rounded tapered tip of the toy pushing against my anus.  Oh my, that was much bigger than a finger!

“Good boy.”  She says.  “Remember baby, that’s me there.  That’s Mommy knocking on your door.”

“Mmm.”  I nod.

“Take a deep breath.  Relax.  I’m right here with you sweetie.”

“Hahhhhh.”

“Okay, slowly start to push it in.  Your bum might fight it.  Just pause and relax.  Let yourself open up.  Then push a little more.”

Hunched forward, my thumb across the balls and my fingers hooked around the base, I pull the dildo in toward me.  The pressure builds and, just as she told me it would, my butt clenches at first.  But I was getting used to this feeling now and with a deep breath I am able to at least partially relax and open myself to it.

“HAH!”  I gasp as it doesn’t glide but pops in a couple of inches all at once.  “Ohhh.”

“How you doing baby?”

“Hnnngh. It’s thicker than I’m used to.”

“I bet it is.”  She says warmly.  “Oh, you look so pretty baby.  You are doing so good.”

“Nnnnngh.”  I slowly pull the dildo into me, feeling every detail of the veiny surface as it pushes through my taut sphincter.  “Mum!”

“Shhh.  It’s okay.  I’m right here.”  She says as her gaze takes in not only the toy entering me but overwhelmed expression on my face as well.  “You can do it baby.  I’m right here with you.  You are doing soooo good.”

With Evelyn’s encouragement nothing was going to stop me.  The toy’s thickness was another level to a finger or even two.  It really, REALLY opened me up more than I was accustomed.  Physically it was a new sensation.  A bit like pooping but way better, and in reverse.  Emotionally though it was a powerful sensation as it let those wonderful feelings of submission and vulnerability come out in me.  I hunker lower and bring my knees up to my sides, feet up off of the ground, to go into a full ready to mount bottom pose.

“Oh Donald!  Look at you!  That’s it.”

“Mmmmm.  Nnnnnngh.  Ohhhhh!”  I moan unabashedly as I pull the last few inches in.  “Nnnngh!”

I discover that the new depth is just as heady as the girth.  I let out a shuddering breath as the head of the toy delves into new and unspoilt regions.  I stare at the screen, at Evelyn’s caring focused expression, and hold the dildo right in to the fake balls.

“How you doing baby?”

“Ohhhhh.”

“Yeah baby?”

“It’s…so…good.  So good!”  I groan in my special high supplicating voice.  “Ohhhhh.”

“Good boy!”  She praises.  “You are doing so good.  Just hold there.  Get used to it.  No hurry.  No hurry.”

I hold it deeply and clench down to feel it’s unrelenting firm thickness.  The cock gave me something to really bear down on.  It didn’t simply touch me or probe me, it filled me in an incredible new way.  The rectal invasion was unfamiliar and sensitive but also…satisfying.  The finger had been an lovely appetizer but now I was finally getting a proper filling meal.  By instinct my hips hump back against it, my straining cock letting out a steady stream of precum.  I grind into it, every tiny shift and twist a fresh bliss.  

Having a cock inside of me, stretching me and filling me and delving deep into me, is a submission unlike any other.  How much more could a man give himself to someone than this?  How much more could he yield to his Mistress?  I had given her my body in the most humbling and intimate way imaginable.  My body was hers, inside and out.  In the buzz of my powerful submissive high I let my imagination soar.  The hard penis in my ass comes alive!

“Hahhhhh.”  I whimper as my head swims with this brand new pleasure.  “Oh…you’re deep.  I feel you inside of me.  I feel youuu.  Ohhhhh.”  

“Yes!  That’s it.  That’s Mommy cock inside of you.”  She gasp.  “Ohhh, you feel so good on my dick baby.”

“Ohhhh God!”  I groan loudly.  “YES!”