Son for Hire: Chapter 88 (Patreon)

“Mmm, what’s this?”  Evelyn says as if she didn’t know.  “Let’s see.”

From the bag she pulls a white tube of hard shell plastic about a foot along and four or five inches across.  Thinking at first that she was going to try to put that inside of me my eyes bulge and I gulp nervously at the sight of it.  She chuckles at my reaction.  Gripping it on one end she unscrews a cap.  Inside of the shell…is a butt hole!  Made of some soft pale pinkish-beige silicone the end looked like a plump ripe peach.  It was a booty in miniature except with a full sized sphincter smack in the middle.  With her index finger she plays with the hole and stretches the flexible hole this way and that before giving it a kiss.

As I watch her playing with the masturbator toy I wonder how often she’d used it before and whether she fantasized about that booty hole being mine.  I would have bet anything that she had.  In my stroking hand my cock flexes hard at the thought of my MommyDom fantasizing about little ol’ me.  She pinches and pulls and plays with it for a time before sinking her fingers into the tiny butt cheeks to pull the soft, squishy interior out from the plastic shell.  Given her massive girth I surmise that this was how she usually used it as the exterior would constrain her too much.  I laugh at how the insert flaccidly droops and dangles around in her hand like a great big floppy dick.

Without a word she takes the lube and gets the hole good and greasy slick then brings toward me.  Following her lead I stop my stroking and line my cock up with the hole.

“Oohhh.”  I sigh as she guides the fake booty hole onto my manhood.  My dick, slick with lube, discovers the inside of the toy textured with supple ridges and bumps.  “That’s nice.”

“Mmm.”  She smiles and nods.  “It is, isn’t it.”  Reaching up she strokes my face and runs the hand down my chest.  Gazing into my eyes she whispers.  “If you’re really good…maybe we can try the real thing later, hmm?”

“Wha?”

“You don’t want to fuck my bum baby?”

“No!  Yes!  No!  I mean…ohhhh yes please!”

She giggles.  “We’ll see how it goes.”

“Yes Ma’am!”

As she holds the toy in both hands and slowly strokes me she tells me.  “Lube up Mommy’s cock my boy.”

“Yes Ma’am.”

Taking the bottle and reaching around Evelyn’s arms I drizzle a long line of the clear lubricant down the center of her dick.  Putting the bottle down I then begin to stroke and work the big tool in both my hands until her fourteen plus inch organ gleamed.

“Thank you.”  She says.

“You’re welcome.”  I smile.

Gliding the toy in tight to my body so that my dick was all the way inside of it she slides her hands over the silicone tube to the opposite tip.  There she hooks her two thumbs into the drainage hole and stretches it wide.  It was only then I realized what she was doing.  I watch as she pulls the toy over her fat knob and enters it from the other side so that we were spit-roasting the toy between us.  Holding it firmly in both hands she pushes in, the silicone bulges mightily as she enters it.  I feel as her thick slick schlong glides in under mine and suddenly makes the space SUPER fucking tight as the shared tunnel is stretched taut.  She keeps going until her tip pokes out of the stretchy butthole to poke me in the balls.  Whereas I was engulfed by the toy, reaching just past half way inside of it, Evelyn had pierced right through it with a couple of inches to spare.  

“Here we go.”

With that she begins to push and pull the toy forward and back between us.

“Ohhhh.”  I moan as the motion brings those stimulating ridges and bumps to life, made five times more intense by the fact her big shaft stretching everything tight and forcing my cock up against the titillatingly textured roof of the tunnel.

With both of us lubed up the synthetic bussy glides smooth and easy like a slow well oiled piston and cylinder.  Evelyn gazes into my eyes to mix a deep connecting intimacy in with our sexual fun.  I stare back entirely enthralled by her long silky red hair, her soft plump lips, her striking hazel eyes, her subtle but bewitching freckles, and so more.  Her body was a masterpiece by God but just her face alone was enough to enslave me to her natural beauty.  What tiny ‘blemishes’ there were, a hint of a wrinkle here and a barely perceptible worry line there, only enhanced her mature but unfaded grace.  As blessed as she was in her looks though it was the pure love shining through her that truly made me hers.  No fresh faced twenty-something could ever touch the heaven sent perfection of my Evelyn.

“Ohhhmmm.”  I let out another groan as the super snug masturbator runs back and forth and back and forth over the top of my dick as below it Mommy’s warm smooth shaft slides against me.  Those firm yet supple mounds and crevices certainly were doing their job against my tender knob!  The difference that I could feel in density and texture between her rock hard shaft and fat pillowy knob was another wonderful delight.  The way her tip would poke out to nudge my balls, as if to prod them to hurry, just added to the experience.  Thicker than my wrist and many times the weight her cock bullies mine around inside the shared space of the toy and it felt incredible.  I never tired of being reminded of my place with her.  I was the little prince, she was the reigning Queen, as it should be.  “This feels…goood!”

“Mmm, it sure does.”  She says, her voice warm and controlled.  “I wonder who is going to cum first?”

“Hnnnghhh.”  I whimper.

She kisses my open panting lips, sweet and gentle, then whispers.  “Hold onto me.”  Leaning forward I slip my hands around her wonderful hips and rest my cheek on her shoulder as I nuzzle into her soft good smelling neck.  She kisses my head then lays her cheek against it.  “Good boy.”

Evelyn lets go of the toy with her left hand so that she could put it around me, she only needed one hand to keep the stroking going at this point.  Our slippery dicks roll and slide against each other as the taut silicone pleasures us.  The wet squishing sounds of the straining double fucked toy creates a lewd melody.  Back and forth, in and out, pillar and post are stroked with a steady and merciless rhythm.  The minutes pass by like seconds.

“Hmm!  Hnngh!”  I huff as I could feel my orgasm building.

For her part Evelyn was as hard as I’d ever felt her and she was definitely enjoying herself, but she wasn’t nearly as close to popping as me.

“Ohhhh.”  I sigh softly.  “Ohhhh it’s good!  Mmmmm!”

Her arm around me tightens.  She begins to nibble and suck along the outside of my ear sending sparkles of delight down my spine.  My hands grip at hips and ass as the pressure grows.  Not letting up for second to let me recover she keeps going and stroking and nibbling and thrusting.

“Nnnnghmmmm.”  My high voice lets my distress be heard.  “M-ma’am?”

“Yes my sweet?”

“May…may I cum please?’’

“Mmmm, not yet baby.”

“Ohhhh!  Yes Ma’am!”

I lean hard into her, panting in sudden bursts of shallow breaths, as I fight my second climax.  She holds me tight and peppers my ear and hair with kisses.

“A little longer baby.  Just a little longer.”

“Nnngh…mmmm…hahhhh!”  My pitiful moans fill the air as I fight the urge to pull out to relieve the constant stimulation.

“My sweet little Prince.  What music you make.”

“Ohhhhhhh!”  The toy strokes, her cock slides, the mind bending pressure builds.  I knew this feeling.  An intense feeling of heady ecstasy mixed with aching denial as I ride the precipice of orgasm.  She had played with me before like this, bringing me right to edge and telling me to hold it back, but this time there were no breathers or breaks.  This time the stroking just kept going.  “Hnnnngh!!!”  I squirm and whine and nuzzle harder into her as the relentless stroking just kept going.  “Please!”

“Not yet baby.  Soon.”

“HNNNGH!”

Stroke, stroke, stroke.

My body was trembling, my physical limits were at their very brink, but with extreme focus I hold out by sheer force of will.  I impress even myself by not nutting.  It wasn’t so long ago that I would have been helpless to my bodily urge for release.  It was only because of my previous experience and the fact that I was so desperate not to disobey or disappoint my dominant in anyway that I manage it, though I didn’t know for how much longer.  It felt sooooo good!

“HaaAHHH!”  I mewl.  “MUM!  PLEASE!”

“Okay Donald.”  She whispers.  “You may cum.”

Now cumming is always great, but getting permission to cum from my Mommy-Mistress made it so that my submissive soul could achieve bliss along with my body.

“OHHHHHHH!!!” 

The pleasure and relief that hits me as my cock blasts its load with the force of a twelve gauge shotgun is indescribable.  I buck and spasm, holding to her soft body with all I had, as I ride my second orgasm through.  It was every bit as good as the first.  The inside of the toy gets hot and a lot more wet as my creamy load coats the ridges and bumps and Evelyn’s big cock.

“Ohhhhh, nice and warm.  Oh, that’s a good cummy baby.  Making it all warm and slippery for me.  Mmmm, yes.  Good boyyyy!”

“Hahhhhh!”

My pumping climax peaks and soon peters out…and still the stroking continued.

“Hohhh!  Ohhh!”  I blow heavy breaths as my mind returns from orgasmic heaven.

“Take the toy.”  Evelyn tells me.  “Finish me off my pet.”

“Yes Ma’am.”

I keep my head on her shoulder and reach down between us.  With both hands I grip the toy as she lets it go.  Keeping the same pace I continue stroking us.  Evelyn puts both of her arms around me and slowly rocks her hips, holding me close as she lets me take her the rest of the way.  The slick sounds turn downright sloppy as my cum churns within and dribbles frothy ooze from both ends.  Gritting my teeth I steel myself as the heights of pleasure turn into an exercise in endurance as my sensitive post-nut cock continues to be squeezed and stroked.

“Ohhh, that’s it baby.  Just like that.”  She moans into my ear.  “I love feeling you against me.  I love your penis rubbing on mine.  I love your hot thick load all over my cock.  Ohhhh Donald!”

Discomfort or no I keep on stroking.  I would rub my dick right off of my body before denying my woman the bliss she so deserved.  Thankfully the aching tenderness passes in a few minutes.  Even as I soften I am careful to keep inside of the tunnel as I hadn’t been given permission to pull out.  Her sexual fortitude puts mine to shame, but that was no news to me.  More minutes pass by with me stroking and Evelyn holding to me and humping against me.  I could feel her energy building.  I could hear it in her breath, I could feel it in her warming skin and rising sweat, and I could sense it in the urgency of her rocking motion.

“I love you.”  She whispers.  “I love you baby.”

“I love you too!”

“Oh sweet boy.”  She groans. “Beg me.  Beg me for it.”

I hear and I obey.  “Please!  Please cum for me.”  I stroke faster, my grip goes tighter.  “Please Ma’am.  I want your cum so bad.  Please cum for me.”

“Ohhhhh God…here it comes…ohhhhhh!”  Her finger sink into my back and lets out a final gasping cry.  “AHHHHH!”

With my manhood pressed so tightly into hers I can’t not feel the great throbbing pulse that run from her base swiftly up her shaft to the tip.  The first great spout of jizz shoots so hard that it blasts out of the butthole to drench my balls in warm sticky lady cum.  After a few wads her spurts stay inside of the toy to mix with my cum and coat our dicks in a fresh jizzy layer.

“Ohhhhh.”  I moan happily as I feel her cum.  “Thank you Ma’am, thank youuuuu.”

Chapter 89