Fist First

I am in Evelyn’s bedroom. The only light comes from a trio of scented candles, their warm glow and syrupy rich aroma filling the room. Soft, romantic instrumental music plays in the background. Over the bed was a soft fuzzy blanket upon which she would take me and on the corner of the mattress some gloves, towels, wipes, and a bottle of our favorite anal lube. The mood was set and everything was ready.

Naked and bound I am on my knees on the floor just past the foot of the bed. The bondage was simple, just my wrists bound together, but it was enough to elicit the feeling that I was hers and she was in charge. After the turbulent day I’d just had I could think of nothing that would have felt nicer than feeling helpless and under my Mommy’s care. In our time together I had come to learn that being all tied up in this special space was the safest and most wonderful place in all the world. Nobody could touch me here…except her.

With my dick as hard as diamond and my butthole being opened up with a thick plug I stay kneeling with my head bowed in total supplication as I await my Mistress.

She was in the washroom and through the closed door I could hear her humming softly, a merry little tune that I’d heard her sing many times before. Somewhere along the way she must have come to associate that sweet melody with me just as I had come to connect it with her. For my ears the song meant acceptance and warmth and love. I tug against my cuffs just to feel the comforting constraint as I tremble with anticipation.

The humming stops and a moment later the bathroom light turns off and the door slowly swings open. Stepping out from the shadow of the darkened room into the golden glow of the candlelight steps my Queen, my Angel, my Goddess. And what a goddess she is!

I had never seen her look more radiant and ravishing. From head to toe she was pure female perfection. She had done her long, vibrant, wavy red hair so that fell over both of her bare shoulders like vermilion waterfall. Framed by her red locks her glossy ruby lipstick bedazzled in its intensity. Around her large stunning hazel eyes and her fine cheeks had been accentuated and highlighted with a light application of makeup. Her body…her thick, fleshy, curvaceous, voluptuous body was my every fantasy distilled into a single woman. She wore lingerie of emerald green and black. The bra was made of delicate lace that held her large plump breasts up and in. I could see her tawny nipples through the swirls. Her garter belt and the top of her black sheer hose matched the fine lace of her bra. And where a set of panties would have been had she worn the entire ensemble…there was nothing at all. Opting not be constrained tonight of all nights Evelyn let her beautiful cock and balls swing free.

Keeping my head bowed slightly I take in her raw physical beauty with upturned eyes. Twenty three years old and I had already found what many spent a lifetime seeking and never finding. I knew how blessed I was. I knew I could spend a million more and I would never find another like her. To this lovestruck guy she was quite simply the most gorgeous woman that had ever lived.

Her mind was in a similar place as she takes a step toward me before stopping and looking me up and down with a ravenous gaze. “You are such a beautiful man.”

“Thank you.” I whisper.

Reaching down she take a grip of her thick, meaty schlong and swings it back and forth. She wasn’t fully hard but she was hardly flaccid either. Clearly she’d been thinking about me. “Open up my Prince.” She says with gentle authority. “Make me hard.”

“Yes Ma’am.” I smile then, like a hungry baby bird awaiting a meal, I raise my chin and open my mouth as wide as it would go.

Lifting her dick she feeds it into my open maw and slides a few inches in. “Mmm, so warm and wet.” She croons. Standing over me and running her fingers through my hair she says. “Hold onto my leg baby and suck it the way I like.”

“Mmmmm.” I moan my affirmation as I gobble down as much of her as I could handle. That very particular submissive joy I always felt while cock sucking fills me up, heart and soul. With my wrists bound I grip onto just one of her soft, shapely legs just above the knee and begin to suckle gently and steadily, just how she liked it.

“Yes. That’s it.” She tenderly combs her fingers through my hair again and again. “Just like that. Good boy.”

“Mmmm.” It is an incredible feeling to know your partner so intimately. Nobody else could sexually pleasure her as well as I could because nobody else knew and embraced her tastes as well I did. And nobody else would have trained as hard at their skills either. As the submissive of such an incredible woman I took real pride in my work. When not actually going down on her I had been reading articles and watching videos and honing my oral talents on my training toys. I could eat pussy and suck dick like a real pro now, as the rapidly swelling cock stretching my jaw could attest. “Mmmmm.”

“Ohhh baby.”

My eyes closed and my wet lips tight around her shaft I rock forward and back, savoring the feel of her sliding in and out. “Mmm. Hmmm. Lrrmm.” I mewl and purr just how we both liked it, high and soft and submissive. “Mmmmm.”

“Sooo beautiful.” She caresses my temple. “My precious Donald, you do that so good.” She praises me. “Now let your hands wander. Touch me baby.”

“Mmmm.” Together my hands glide up her leg, the right along the supple inner thigh and the left along the smooth outer thigh. Keeping the rhythm of my head steady as I suck her now hard penis I guide my hands by touch. When my fingertips find the bottom of her heavy hanging balls I shift my hands over so that I may fondle her.

“Hahhh!” She gasps softly as my hand gently tighten around her testes.

I feel their girth and weight, so much greater than my own, and pray that their creamy contents would be inside of me before the night was through. I wanted so badly for her to cum inside of me, for her to fill me up with her hot seed. Enjoying the feel of the loose velvety skin and feathery soft pubes I fondle and massage and gently tug at her plum-sized nuts. Her cock flexes to its full hardness, straining my jaw but feeling incredible as it stuffed my maw. Down below my hole hungered for her. As good as the plug felt…I was greedy for more! Somewhere along the way I had become a size-prince. Luckily for me my hung Queen had all the size a boy could ever handle.

“Mmmmmm!” Opening my eyes I gaze up at her needily. “Hmmmm.”

“Soon baby, real soon.” She smiles down on me, her hips slowly pumping in and out. Pulling out she smears some precum across my lips as she lets me rest my jaw then feeds her oak hard rod back in once more. “I promise.”

“Mmmmm.”

Slurping and sucking I slide my hands up to stroke her shaft before running them back over her balls to tuck in behind them. There I find her warm, wet pussy. She spreads her legs a little to give me space which I use to rub with one hand while with the other I push two fingers into her slit.

“Ohhh, yesss.”

I suck her. I finger her. I rub her clit. All tenderly and lovingly while cooing softly. “Mmm. Mmm. Mmmm.”

“Good boyyyy.” She pets my head as she arches her back seductively. “Ohhhh.” For a few minutes she savors the pleasure I am giving her before letting out another long sigh. “Ohhhmmm. Very good baby. I’m ready now. Are you?”

“Mmm.” I nod with a mouthful of lady cock.

“Come on then. Up you go.” She slips her knob from my slurping lips and dabs her tip across my smile once more. I pull my fingers from her moist cunny and lower my hands into a posture of subservience. She smiles and glances to a spot between my knees. “Messy boy.”

I look down to see a dark spot in the rug. Such was my excitement that, without me even realizing it, my dick had been leaking a steady drip of precum. “I’m sorry.”

She chuckles as she helps me to my feet. She kisses me firmly on the lips and whispers. “I will always be here to clean up your messes my boy. Always.”

“Oh!” I swoon into her arms.

Holding me close she walks me to the bed and sits me down on the fuzzy blanket before laying me back onto it. By pure instinct my legs automatically spread wide and pull up to my sides. Not so long ago I would have been embarrassed to be seen so open and **** but now I wanted to be seen like this, by her at least. There was no place for shame in this room. My Dommy-Mommy only ever made me feel beautiful.

She stands over me slowly stroking her monster cock and just admiring my body. I hold my bound hands in close at my chest just below my neck as I knew my hands would only get in the way. She would take control of everything from here on. Reaching down she taps the flat base of the buttplug that stuck of my tush. “How’s it feel?”

“Good.”

“Mmm.” She beams, her fingers and thumb gripping around the circular base. “Okay, big breath in.” I do as she says. “Now slowly out and relax.” Again I obey. As I let the breath escape my lungs I concentrate on relaxing my sphincter. I grunt as the thick part of the plug stretches me but that quickly passes as Evelyn pulls the toy out and away. “Good boy.”

“Hmmm.”

She giggles as she watches my gaping bum wink a few times at her. “Just one last test.”

“Yes Ma’am.” I say, already knowing what was coming. She had always told me that before she would truly take my ass that she would fist me first to make sure I was ready for her cock, which was even thicker than her wrist, and that moment had finally come. When she first told me that I thought it so nasty and raunchy, and a part of me still did, but that only made me want it all the more. The way Evelyn made the even most insanely erotic thing seem so wholesome was a part of her magic.

She sets the plug down and puts on one of the blue medical gloves. Holding it up so that I could see she then slowly drizzles the lube, glimmering in the candlelight, over her sheathed hand. I clench my hands into fists and tremble with anticipation. She chuckles as her fingers and thumb smear the clear lubricant around her hand. “Relax baby. Be calm.”

“Yes Ma’am.” I focus on settling my breathing and heartbeat.

“Better.” She says. Squirting an extra dollop over my hole she returns the bottle back to where it was. Stepping in, her left thigh pressing tight against the back of my right leg and her hard heavy schlong resting over top my dick, she pushes the fingers of her gloved hand against my anus and begins to rub.

“Ohhhh!” I moan.

She nods approvingly, always eager to hear my pleasure. With her dry hand she teases and plays with my tight scrotum. “Ready?”

“Yes’m.” I nod.

“Here we go.”

I could feel her four fingers and thumb converge to a point right at my opening and begin to press. Having just had the plug in me she finds little resistance for the first couple of inches, my booty parting for her like the Red Sea to Mose until the width of her knuckles begins to stretch me. Even this wasn’t so bad though as the plug that had just been removed from me had a girth greater than Evelyn’s elegant hand. And then, as if sucked in by some vacuum, the entirety of her fist slips inside of me!

“NNNGHHH!” My sphincter tightens around her wrist as her hand balls up into a proper fist to fill the space. She twists her hand and wriggles her fingers giving me sensations that an inert plug or dildo never could. “Oh God! Nnnnngh!”

“Feel good?”

“Hmmmm.” I whimper and nod. “So full! Ohhhh!”

“I could tell.” She giggles. “Your toes alway curl up when it’s good.” She carefully spreads her fingers then clenches them back together again. Whether on purpose or not she had just booped my prostate as she often did my nose. “Mmm, you’re so warm and tight my boy. And you’re taking it so well!”

“Ohhhh!” The feeling of something moving inside of me is…indescribable. I squirm and moan, overwhelmed with pleasure. “MNNGH!”

“Ready for more?”

“Hmmmm! Yesssss!”

“Atta boy. Deep breath. Relax.” She places her free hand on my belly as if to pin me in place. Putting one knee up on the bed she leans over me, staying low so that her penetrating arm had a proper angle. More lubricant is applied then slowly and gingerly she presses into me, driving her fist deeper and deeper as the meat of her forearm stretches my ring.

“OHHHHH GOD!” I cry out. “Hahhhh!”

“That’s it. Just a little more. You’re doing so good baby.” She leans down and kisses my tummy. “Here we go.”

“NNNNNGHHH!!!” My eyes roll back as my cock quivers, hard as steel and leaking nonstop. Occasionally I would smear across Evelyn’s fine lace bra as her full breasts would brush over my manhood. “HNNGHHH!!!”

Her fist, her wrist, and the better part of her lower arm stuff my bowels like nothing before. I use all of my skills to relax and open up still yet still she stretched me to the point of a low burn. It wasn’t painful just extremely intense. Now I appreciated why we’d taken so long to get to this point. Despite my desire to hurry things along I never would have been prepared for this until now. Her fist deeper than my longest dildo, her arm stretching me more than my thickest plug, she had me on her arm like a hand puppet. The pressure was intense, more than I ever believed I could bear, but so to was the pleasure. I was stuffed to the brim and that feeling of total fullness was…HEAVEN!

“OHHHHHHH!!!” I groan as she starts to gradually pump her arm in and out of my straining hole.

“It’s good?”

“HMMM!” I nod.

Good? Good!? There were no words to describe this ecstasy. And it went so much deeper than the merely physical. It was so strange to have another persons entire hand inside of my body. So invasive. Yet it was because of this that made it feel so right. This was total surrender. Total submission. Total intimacy. Total trust. I could not be more **** or in a more compromised position and that me feel wonderful! I was hers, completely.

“I LOVE YOUUUU!!!”

“Ohh, I love you too my sweet Donald.” In and out her arm pumps. “I love you so much.”

“HAAAHHHH!!!”

“Look at me baby.” She whispers. “Let me see those beautiful eyes.”

Trembling and panting I **** myself to focus and look at her. She searches my eyes, looking for signs of falseness or suffering. But she sees only a boy’s bliss. As good as her arm was though this had only been a test. The final hurdle before the thing that we both desired most. “I…want…youuu.” I manage to gasp. “Please Mommy! Fuck meeeee!”

“My boy, you did it.” She says at a hush, her face full of joy and wonderment. It was just now really hitting her that after a lifetime of settling for alternatives she was at last about to use her mighty cock as it was meant to be used. “You did it!”