Chapter 5: The Diary of a Femdomme – Chapter 6 [Feminization] [Pain] [Anal]

"No no" she purrs, gently but assertively

She drags the tip of the crop from the back of his knee, around the smooth curve of his buttocks.

The slut whimpers feeling the leather touching his soft lace panties. His bulge presses into the gentle fabric, helplessly.

"Pleaseeee, Mistress", he mumbles into the carpet, knowing full well that his current position makes him vulnerable to a crop across his most sensitive areas.

"I'm new to this" he pleads, "how many so far?"

He thought knew what he was getting into when he first asked her, but he didn't quite understand the intensity that each lick of the crop would leave across his skin. Focused energy, expelled at the moment the tip made contact with his flesh. He's determined to earn his reward and prove himself to his instructor.

"Nineteen", smirking; she is definitely keeping count

She's almost stroking him with the crop, teasing him, gently, but there is a tension in the air waiting to be broken.

He feels the crop pull back from his skin, and his whole body tenses, he holds his breath waiting to feel the impending sharp strike, somewhere.

"It's so cute when you tense up, baby"

More mumbles, face down, exhaling.

THWACK.

The sting ripples across the back of his thigh.

"FUCK"

His owner giggles.

THWACK.

THWACK.

THWACK.

THWACK.

THWACK.

"Baby you're starting to look very pink, I'm really not holding back on you either."

He sucks in air through his clenched teeth, a guttural exhale follows, a long drawn out roar.

"Say it" she commands

"N..o... I can't" he responds

"SAY IT!" she says, louder, angrier

"I DON'T WANT TO" he screams, compensating for the fact he's on all fours.

"Just say 'stop' and it's all over" she muses

"Noo please, I can take more" he whines

THWACK.

No anticipation build up, no teasing, no stroking, another crop.

This time the edge of the crop makes contact with one of his helpless balls, which didn't quite fit into the underwear she dressed him in.

He is silent.

There is silence.

"FUCKING FUCK FUCK FUCK Fuhhhuuckkkkkk"

"Who's a horny slut?"

"hnnnghh fuck, I am, Mistress"

The crop moves away from his skin again, and before he has a chance to prepare, he feels her soft finger tips stroking the back of his legs, stroking, inspecting the welts left on his body.

The sensation of her fingers touching his hyper-sensitive, raw skin creates a heat that draws his attention right back to the current moment.

Her hands cup around his thigh, and begin to slowly stroke up and down, allowing him time to breath.

She lifts her leg up, and places her heels against his left buttock from above, keeping him in place, and rotating herself, she lines the crop up again, allowing for a full swing of her arm.

"Please Mistress... no... don't..."

She remains stationary, unmoving.

"Please really please don't that's gonna hurt so fucking bad fucking please"

She doesn't respond.

"fuck fuck please don't don't it hurts fuck fuck fuck"

"So... say it?" she offers.

"aaghhhhh, no. no. I won't"

THWACK.

Across his exposed balls.

The scream echoes around the house and doesn't stop for several minutes.

The slut in front with her has lost all composure, and is unable to hold himself up. His body has collapsed onto the floor, writhing, curling up, stretching, contorting.

The Mistress casually takes a few steps and grabs the sluts phone from the side. She knows the passcode, obviously, and takes the opportunity to record some memories of the occasion.

"Are you ready to say it?"

He's not paying attention.

"AY!", she kicks him. "Are you ready to say it?"

"Hiippp"

"....hipp?"

"hippapot"

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"..hippapot?"

"hipp..hippapott-"

"hippopotamus?"

"hippopotamus!"

"Good girl!" she coos, kneeling down on the floor next to her submissive plaything.

She strokes his strong legs as he curls into a ball around her, his arms grabbing her, not letting go.

"You did so well, baby!", she strokes his hair, soothing his wounds.

Music plays calmly in the background. There is a calm silence. The pain still radiates through his body, but the sharp intensity of the crop normalises, into a dull, slow ache.

"Are you okay, kitten?" she asks, sincerely.

"mhm" he nods, looking into her warm, kind eyes.

"I'm impressed that you managed to take so many", openly musing.

"How many was it, in the end?"

"Twenty seven".

"They were so hard" he whimpers

He squeezes her tightly, proud of himself.

"What would you like for your reward, pretty girl?"

"Could... could you fuck me, Mistress?"

"I can do that – with what?"

"Your strap-on?"

"The big one or the little one?"

"I think I'd... like the big one?"

She hums affirmatively as she reaches into The Happy Bag for the big strap on.

"Come on", she says as she stands up, extending her hand for him to stabilise himself with.

She leads him over to the bed, and gently bends him over, feet on the floor.

"Pull your panties down to your thighs, sweetie" she instructs, as she slides into the harness.

She kneels down behind him, kissing his sensitive pink thighs, whilst her hands grab and squeeze his ass – pushing and pulling his buttocks, digging her fingertips into the soft, perfectly shaped globes.

Pulling his cheeks apart, exposing his tight, fresh hole, she lifts herself to him, and kisses between his cheeks, light, gentle kisses around his entrance.

Her tongue licks in a straight line up from his perineum, over his opening, taking care to lick circles around it, hypnotising him with the movements of her warm, wet tongue; contrasting with the residual pain of his legs.

He's moaning, purring, getting lost in the feelings. The contrast between the pain and the pleasure overwhelms him, relaxes him.

As she works his bunda, through feel alone, she covers her eight inch strap on with lubricant, all the way down to her hilt.

"Relax now, baby" she reassures, and watches as his shoulders relax into the bed and the tension in his legs drops.

Lining up the tip of the toy against his arschloch, and pushes it inside him in one long fluid motion. His trained ass has prepared for moments like these; so little warm-up needed now, he is always ready to go.

As he feels the long, thick probe pushing its way into his body, he lets out a longer breath, a guttural groan with the inflection of pleasure, rather than the pain of moments ago.

His owner grabs his hips, pushing down, and begins to slide her cock in and out of him. As she looks down, she can see his muscles stretching, gripping the cock, responding to the texture and the ribbing of her phallus.

Smooth and steady motions begin, long, deep strokes of her hips pushing in and out of him. Filling him up to the hilt, forcing him to take all eight inches, before pulling back and leaving him feeling momentarily empty and hollow.

He moans and gasps with every movement – the full length of the toy, angled in such a way that the entire length of the textured shaft rubs against his prostate.

"Mmmm Mistress, that feels so good" he moans

"I've needed this" he sighs

"You're so good at fucking your girl" sounds, dreamingly lost

Her hands explore his body, feeling the muscles in his back, holding his buttocks, running her fingers through his hair, pulling his head back as she penetrates him, over and over, and over.

After ten minutes of solid, stable fucking against his prostate, he can feel the desire building up inside him, the need to release is ever present, but the anal alone is just not quite enough to take him over the edge.

She knows. She can tell by his moans.

She can tell by his breathing.

She can tell by the way his cock grinds against her cotton bedsheets with every thrust.

"Mistress, please can I cum?"

"oh, what?"

"..can.. I cum?"

"...err.. no?"

The thrusting doesn't stop during.

It makes it much harder for him to formulate a coherent response.

"..but.. I.. er.. what?" he stumbles.

"You said you wanted to be fucked" she effortlessly expresses as she continues to violate him.

"but-"

"You didn't say you wanted to cum, did you?"

"I.. oh fuck"

His owner laughs, as she grabs his head, pushes it down into the bed, and continues to fuck him, as his cock continues to rub against the gentle fabric of the fabric, helplessly, again.

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