Drew’s First Mistress – Erotic Short Story

My favourite time of day is upon me. I’m kneeling in my new barn, hands resting on my thighs.

My old Master milked me for the last time yesterday, before selling me to someone new. I’ve not met them yet, but it’s time to be milked.

As time goes by, I can feel myself harden. My body knows what time it is, and the growing pressure in my cock and balls needs to be released.

I crawl towards the barn door, peeking through the crack and see light emanating from the farmhouse – the window glowing in the early morning darkness. I hear the farmhouse door open, and I hurry back to my bed, kneeling again in my soft pile of hay. I can no longer contain the hard length. With my hands on my thighs, the head now poking through the gap between my arms. My stomach is churning, a combination of nerves and excitement causing me to tremble. Staring straight ahead, I hear the barn door open. A woman stands in the doorway with a mason jar and a lantern.

“Oh, look at you,” she says, stepping in and letting the barn door swing shut behind her. “I’ve kept you waiting, haven’t I?” She closes the distance, allowing me to see her better. Standing no taller than five feet, she’s nowhere near as tall as my previous Master. Stopping in front of me, she pets me. Stroking my hair away from my face, she tucks a loose strand behind my ear. The gentle gesture making my heart flutter.

I look her over; wearing thick black boots matched with a denim skirt and white shirt, she looks like a typical farmer’s wife. Her black hair in pigtails on top of her head, her face round and soft, and her lips red. “Your Master isn’t coming today, but he still needs his milk. So, you’re going to have to make do with me.” She smiles softly. “Is that okay?”

I nod. “Yes, Mistress.”

Her smile grows as she reaches down and takes my arm, leading me to the milking table. “You’re going to be a good boy for me, aren’t you?” 

“Yes, Mistress.” I climb onto the table, my cock and balls barely fitting through the small hole allocated for them. As I relax, my dick begins to drip while she buckles me in – forcing me to lay with my left cheek against the hard surface, allowing me to look at her. 

“Aren’t you precious,” she says, warmth in her words as she taps my nose and pats my head. Then, reaching under the table, I feel her hand brush against my erection before it’s enveloped in the milker. Hearing the machine roar to life, the suction on my member immediately makes me want to thrust, but I’m unable to. The buckles are too tight for any movement. 

I groan, the machine sucking the life out of me.

My new Mistress comes to stand by my head. “Oops,” she says, noticing some of my precum on her hand. She raises her hand to her mouth, laps it up and moans. I watch her eyes widen as she looks over me, watching as my muscles tense and spasm under the intense suction of the machine beneath the table. 

I whimper uncontrollably, feeling my cock ache as I’m milked.

She licks her bottom lip, lust in her eyes. “Let’s stop this,” she says, reaching under and turning the machine off.

The loss of suction and lack of climax leaves me panting. The pump is pulled off within a few seconds, and I’m left wanting. I’ve never had the machine stop mid-milk; I’ve only ever finished in the suction. My last Master ensured I could never finish without being in it. 

Mistress stands next to my face again, slowly unbuttoning her blouse and revealing her udders, large and pink. She takes them between her thumbs and index fingers, squeezing and tugging. “Here you go,” she says, leaning down and putting a nipple in my mouth. 

I take the large bud, sucking and chewing softly, earning moans of pleasure. I close my eyes, enjoying the plump nub – licking and sucking, feeling it harden further in my mouth. I’ve never had a Mistress before. I can get used to this. 

After a few minutes, she switches breasts – allowing me to continue. Moan after moan, my cock continues to leak. She leans, pressing her large breasts against my face. I breathe through my nose as I continue tugging and lapping at her nipple, the scent of roses coming from her skin. 

Mistress steps back, pulling out of my mouth. Her lower lip between her teeth as she looks at me, her eyes low – looking at my cock under the table. “Let’s get your Master some milk. Then I’m going to have my way with you…” I see her kneel beside the table, and I feel her grasp me, slowly stroking.

My dick is huge compared to her small, delicate hand. “Gosh, you’re so big,” she giggles. She grabs my balls, tugging at them before massaging them – my cock dripping. “Good boy,” she gasps as I shoot a soft load. 

She comes back to stand by my head, licking one hand while the other holds a half-full mason jar. She moans around her fingers, eyes rolling. “You taste so good. No wonder Master bought you.”

I smile while watching her lap up the excess on her hand. I’m milked every day, and have been for the past eight years, but I’ve never seen someone enjoy my produce. 

She closes the jar and jumps on the spot in happiness, her breasts bouncing before my eyes. “I’m going to go take this to your Master. Stay still for me, okay?” She says, winks and leaves the barn – the door slamming behind her. 

I can’t see anything from this area of the barn. I’m tucked behind a wooden wall panel.

After what feels like an eternity, my cock throbbing from the lack of release, I groan loudly. Finally, the barn door bangs and Mistress is back in sight – her bountiful breasts still hanging from her shirt. A long object sticking out of her skirt pocket.

She slaps my behind, sending a pulse of pleasure through me. “Quiet now, you’ll wake the kids,” she giggles before vanishing under the table. 

Within a few seconds, I feel her lips on my erection. She kisses up my shaft, and her nose buries itself against my bollocks. I hear her moan underneath me, a wet sound echoing in a steady rhythm around the barn.

“You’re so delicious,” Mistress whispers before taking me in her mouth.

Sucking delicately on the tip, both hands moving on the shaft, carefully pulling my foreskin back and forth as she milks me into her mouth. 

I moan, unable to hold back as her tongue flicks over the tip and plays with the hole. It’s not long before she takes me deep into her mouth, her lips almost touching the base of my cock – only limited by the table between us. I jerk in her mouth, my stomach spasming, and my hands clenching into fists. Don’t cum. Fuck. Don’t cum.

I shoot a soft load down her throat, hearing and feeling her gag beneath me. Wanting to thrust but not being able to.

When she finally pulls away and stands next to the table, I feel lost without her around me. I want more.

Mistress grabs my ass cheeks, pulls them apart and spits against my arsehole. “You’ve got such a beautiful bum,” she whispers. Suddenly, something is inside me, pushing deep. It’s already wet. She must’ve enjoyed it while drinking me.

I moan. My cock jerks and drips as the object rubs against my prostate. I haven’t been milked this deeply in years. 

As the motion quickens, bashing me against the table, I feel myself getting close. “Mistress, please.”

She stops, leaving the object inside me and leans so that her face is next to mine. “Just a little longer, and I’ll finish you off. Just don’t climax, okay?” She says softly, lightly kissing my nose before returning and pounding my ass. 

Feeling my balls and cock swell and throb, my dick spasming underneath me as she milks my prostate, I shoot another load – bigger and thicker this time. The item is swiftly removed and leaves me feeling empty. Fuck. What’s next?

The buckles are undone without a word. Mistress moves to stand by my head, grinning mischievously. “Roll onto your back,” she commands. 

I do as I’m told, and she buckles me back in, keeping me flat on the table. 

“You’re not going to tell your Master about this, okay?” She whispers, climbing onto the metal table and squatting above me. “It’s our little secret,” she adds, grabbing my hard length and guiding it into her. 

My dick is engulfed, her warm and soaking pussy squeezing me as she slowly lowers herself. “Fuck,” she hisses, taking me to the hilt and beginning to roll her hips. “You’re such a good boy,” she cries, eyes rolling back as she rides the pleasure of my cock touching every wall of her innards. 

She pulls her skirt up, holding it around her hips as she begins to bounce, her beautiful cunt tightly framing my cock. “Mistress,” I moan as I watch and grip the sides of the table. Then, with one hand on her skirt, holding it in place – her other hand reaches for her left nipple. Tugging it, biting down on her bottom lip as she fucks me.

This is my first time. I’ve never been in a Mistress before. I’ve only ever been milked by a machine. But this is much better. 

I moan, almost a scream, and her eyes are back on mine. Holding eye contact as she speeds up, the slapping of her ass against my thighs echoing around the barn. 

She whines as her hand moves from her breast to her cunt, her index and ring finger pulling her lips apart, allowing her middle finger to work in circular motions over the tight nub. 

Mistress erupts, a flood spraying across my thighs, abdomen, and chest.

I groan as her cunt grips my cock like a vice while she pushes down, holding me deep inside her. 

I jerk in her as she routinely squeezes and releases around me, milking me with her tight cunt. Feeling her drip onto my balls and thighs, my eyes roll back, and my body relaxes.

She slowly pulls off me, releasing my cock from her tight twat. I look up to find her eyes still hungry. It’s not over yet. I want more. I need more.

Mistress moves up the table. “Open that pretty mouth,” she demands, lowering her pussy onto my face. As I lap at the entrance, cleaning her labia, I feel her tensing and relaxing. Finally, I see it – my milk seeping out of her. I reach up as far as I can, my tongue lashing at her pussy as our sweet load escapes her and drips into my mouth.

Our cum mixes together to make the best milk on the planet. “Fuck. You’re my new favourite cow,” she growls before lowering herself further to sit on my face. My nose presses against her clit as my tongue delves into her, licking her precious little cunt. She grinds, using my nose to stimulate her further. 

It’s not long before another gush is released, the final few drops of my milk seeping out. I gulp us down, the sweet nectar filling my belly. The best breakfast.

Mistress sighs, scooting off me, getting down from the table, and letting her skirt hang free. She begins to button her shirt.

I watch her in awe while I pant, trying to catch my breath. Her honey on my face, chest, stomach and thighs. I can smell her – nothing but her. We taste so good together.

She steps closer, smooths my hair back and smiles softly. “I’m so happy Master bought you,” she whispers. Mistress leans down and licks my lips. My whimper, tingling under the touch of her tongue. “Don’t we taste amazing…” Mistress sighs while she begins to unbuckle me, releasing me from the table. 

She grabs my limp cock and tugs it. She leads me off the table and back to my hay bed. I kneel and stare up at her, her eyes holding mine.

She cups my face, kisses my nose, smiling sweetly. “I’ve never taken one of his cows before… I might need to make a habit of milking you,” she whispers. Her tongue flicks out and licks my nose, residue of us still on my face. “Maybe I’ll just have to keep you all for myself.” Mistress pauses, her eyes searching mine. “How would you feel about that, Drew?”

I smile, tears welling in my eyes, my chest tightening, and my cock throbbing again. “I’d love that, Mistress.”