tagBDSMLucky Bastard Ch. 08

Lucky Bastard Ch. 08


Author's note:

In previous chapters: Annie hooked up with Rye, her long-ago gymnastics coach, aboard a trans-Atlantic flight to NYC where they played kinky games and fucked in the cramped bathroom. Their play continued in Annie's hotel room shower where Rye fingered her ass and taught her how to deep-throat. He later tied her to the bed, edged her and fucked her with a beer bottle while playing roughly with her tits. The next morning Annie broke Rye's rules and got her first punishment spanking.

In this chapter: Annie's ass-fucked in punishment, but will it be too much for her to take?

A HUGE thank-you to my editor, the Brit, who had whipped me as well as this chapter - indeed this whole story - into shape with his keen insights. I owe you so much more than a beer. Thank you.

Enjoy the read!


"Yes sir. I'm ready for my second punishment."

My bottom is still hot and sore from the hard spanking it had just received and I can feel my heartbeat throbbing in my pussy, my clit and my anus, the whole area swollen and tender from Rye's expertly-placed slaps. Still I stand tall and still, if slightly shaking, and accept the fact that I have not yet completed paying my dues. I broke his rules twice, so I have a second punishment coming.

Coach Rye takes my face in his hands and bends down to place a soft caress of a kiss on my lips.

"That's my brave girl. Very well sweetie, let's get you ready then. For this second punishment I want you to turn back to face the chair and put your knees onto the seat all the way back so your weight is on the length of your shins. Yes, exactly like that. Now rest your collarbone and shoulders along the top of the back pillow and clasp your hands behind your back. Good. Stay."

I hear him move over to the bed behind me and fumble with something though I cannot tell what it is. In a moment he is back and moves into my field of vision between the chair and the wall to show me the two terry-robe sashes in his hand.

"I am going to tie you up again Annie, and then I am going to gag you because your mouth is no longer buried in the seat and I don't think you'll be able to keep your voice down for the duration of this punishment. The gag won't block your voice completely and you'll be able to breathe around it, as well as through your nose, but it will effectively muffle your screams. Understand?"

My eyes grow large as saucers and my throat constricts as fear slashes through me.

He's going to gag me in order to muffle my screams?! What the FUCK?!!

And yet...

...and yet here I am, not yet bound but keeping my position over the chair all the same. I could stand up, get dressed and check out. I could safeword right here, right now. And yet I choose not to. He thinks I can do this. I can do this.

Coach Rye crouches in front of me looking into my eyes over the back of the chair. "I need an answer Annie. Use your words."

"Yes, sir. I got it. You're going to tie me up again and you're also going to gag me to keep me quiet. I understand sir."

"Good girl. Now we need an alternate to safeword seeing that you'll be gagged. I'm going to give you something small to hold in your hand; If you drop it I'll know I need to stop and check-in with you, all right?"

I gulp again and answer: "Yes sir, thank you."

He glides his fingers gently down my pale cheek in a strangely reassuring gesture before moving behind me to tie my wrists together behind my back. Once finished I hear him moving away from me towards the bathroom, some muted shuffling around, and then he's back at my side and placing a small plastic tube in my right palm, closing my fingers tightly around it.

"It's your lipstick, sweetie. Hold onto it. If you drop it that would signal for me to stop, okay?"

"Yes sir."

With my weight divided between my shoulders and collarbone on the cushioned backrest and my knees and shins on the wide, padded seat the position is surprisingly easy to take, and I will myself to relax into it.

Whatever it is he's going to do to me, he thinks I can do this. I can do this.

Coach Rye re-appears in front of me and crouches down again.

"Now your gag. Open your mouth sweetie."

I open and he wraps the sash around my head placing it between my parted lips before pulling it behind my nape so that it settles in between my teeth pushing my jaw open. He repeats the process twice before tying the makeshift gag securely behind and I relax my jaw letting my teeth sink into the thick cotton now lodged in my mouth.

"Breathe through your nose Annie, we've practiced that before. You should have no problem breathing through your mouth either but I'm sure it would feel strange so focusing on inhaling through your nose should be easier. Yes, very good. Go on, take even breaths and exhale all the way... Good girl. Don't forget this during your punishment. Remember I don't want you passing out on me."

Getting up and stepping around to stand behind me he starts rubbing his hands gently against my bright-red ass cheeks, drawing small whimpers from my gagged lips.

"You have no idea how gorgeous you look right now Annie... Bound and gagged, red and sore from your previous punishment yet completely submissive and ready to take more, whatever it may be. I've never seen a woman more beautiful in my life."

He continues to stroke my abused ass as he speaks, sending fresh sweet pleasure/pain into my needy cunt. My palms are sweaty and I relax my fingers a little around the plastic tube, but still make sure it wouldn't accidentally fall. I want this.

His hands leave me momentarily and I hear him opening and unzipping his jeans and sliding them off his legs, and then the unmistakable tear of a condom wrapper. In another heartbeat he steps right up to me and I feel his heavily erect cock rubbing up and down my inflamed, still-stinging slit.

He uses just the spongy crest of his dick, clad in the pre-lubed condom, to glide up and down along my sensitized labia and over the hood of my clit, pleasuring me now, the soreness from his spankings only a distant undertone. I arch my back in response and he continues playing me, teasing us both, making my need come back to the fore and my pussy to cream again.

"Yes, that's right sweetie, let's get you nice and lubed, we're gonna need all that juice for your next punishment."

I don't quite understand what Rye's saying but right now I don't really care because his cock head is rubbing me so, so right. In spite of the post-spanking burn in between my legs -- or maybe because of it? -- I feel myself building towards a peak and my juices flow again to coat my folds, making them smooth and slippery.

Mimicking his own movements from before but using his dick instead of his fingers this time Rye dips only the thick head into my honeyed opening, and glides it up my crack to rub around my tender asshole. Again and again he repeats this process, spreading my cream all over my rosebud while driving me mad with unfulfilled need at the same time. In my bound, bent-over position I have no leverage to push back and I am left to simply take his slow, hypnotic, precise moves over and over again.

I try to squeeze hard around his cockhead to keep it inside of me, to suck it in further. I know it won't work but oh, does it feel good to try. And the way Rye's fingers tighten their hold on me every time I do so tells me he's not immune to it, either. His voice sounds strained when he speaks.

"Almost ready sweetheart, now all we need is a good amount of lubrication all along my dick..."

And with that he grabs onto my hip bones and thrusts slowly, fully into my pussy and I feel my inner walls unfold and stretch to accommodate him as he slides all the way in. When he bottoms out he pauses and grinds against me, his thick head bumping against my cervix and his hard pubis pressing roughly against my tender, just-spanked flesh, causing fresh pain to rip through me and spill out of my lips in a squeal just barely muffled by my gag:


At the same time my pussy clenches and floods around Rye's hard meat and he lets out his own guttural growl: "Arrrgggghhhh yessss... squeeze my cock with your pussy... get it all wet with your girl juice sweetie... Oahhh yeah that's right, just like that. More..."

He grinds himself deep inside me and I squeeze myself around him, the acute pleasure of being filled and stretched by him enhanced by the sting of his coarse body hairs scratching my sensitized skin. I rotate my hips and feel the movement echoed inside causing even more honey to flow and gather around his base.


I'm not sure if he directs the word to me or to himself. Either way Rye pulls out and I know his cock must be shining with my juices and jutting rock-hard and painfully engorged before him. He rubs it again along my crack and over my rosebud and then lets the very tip of his head rest against my tight rear entrance.

"Okay Annie, I am going to start your second punishment now. I am going to fuck your ass. I'm not going to be gentle about it and I am not going to stop until I cum deep inside your belly."

I nod my understanding. "Nieh hir."

"Good. Now it's going to be uncomfortable - probably going to hurt - but not because of my cock in your ass since you'll be well-lubricated and I'll take care not to tear you. However as your asshole is still sensitive from your previous punishment I expect there will be some pain involved. Understand?"

Fuck. "Nieh hir."

"Okay. Like I told you before your previous punishment I want you to focus on taking it in, absorb the sensations and the feelings and keep breathing through your nose, and you may not cum. You will submit yourself to this punishment and at the end of it you will probably be hurting and frustrated and feeling completely and utterly used... and you will also be fully forgiven for breaking my rules. Understand?""

Heart lodged in my throat I nod and answer again around my gag: "Nyeh hir"

"Good. Now you know what to do, right? You told me you do this often... Relax your sphincter and push out a little. Here we go."

I let my head hang down, close my eyes and exhale slowly through my nose, and consciously relax my tight back entrance. Immediately I feel Rye's velvety cockhead push insistently in, his palm flat on the small of my back holding me steady. My anus is already sore and a little swollen from the direct spanks it got earlier and the pressure on the still-raw nerve endings is more than a little uncomfortable.

It hurts, dammit!

Involuntary sounds of distress tear from my gagged mouth but his cock is like a force of nature, relentless and unstoppable. Rye keeps pushing slowly and I feel a burning sensation as my ring of abused muscle is forced to stretch ever wider around his rock-hard, slick, engorged head.

Incoherent pleas try to make themselves heard over the ever-increasing burn but cannot be deciphered through the thick cotton between my teeth, and I frantically shake my head and flex and point my feet trying to release some of the tension pooling heavily in my body. At the same time my fingers keep gripping my lipstick securely. He thinks I can do it. I can do it.

Coach Rye seems to ignore me completely and just keeps pushing slowly and forcefully in, the thick, creamy girl juice coating his member aiding him in his quest, until suddenly his mushroom head pops fully in. Immediately the edge of the burning pain subsides.

Ahhh! Phew. The worst of it is over.

I realize I had been holding my breath, so I re-focus on drawing air into my deprived lungs through my nose as instructed. Rye holds himself still for a few breaths and I know that despite his earlier warning he's not completely indifferent to my discomfort, and that he's giving me this small pause so that I can adjust and prepare myself for what's coming next. I relax a little further and breathe more easily through my nose and around my gag.

With both hands Rye now grabs the tops of my fleshy butt cheeks, his thumbs and fingers sinking into my shining red globes, and he uses these handfuls of my heated flesh to keep me in place and slowly plow all the way in. Tightening his hold even further he immediately starts pulling out until only the head remains in me and then plunges deep right back into me. He grinds against me and then withdraws almost fully only to push all the way in again. As he does I am pushed forward into the chair and feel its coarse material rub roughly against my nipples, adding to my sensory overload.

Rye picks up his speed and soon he's holding nothing back, using his whole body mass and his powerful thighs and hips in deep, forceful thrusts. He bottoms out on every plunge and when he does his thicker base painfully stretches my abused sphincter, his hard pubic bone smacks my tormented cheeks and his heavy balls slap against my tender, red, puffy perineum and outer lips. On top of it all with every push my nipples get another rough rub from the cushion fabric.

It hurts. It really hurts.

The pain isn't sharp enough to make me scream -- I mostly whimper and moan -- but it's insistent and constant and seems to come from every nerve ending at once. And at the same time the feeling of being stretched and filled is not all bad, either. Every time his cock is stuffed forcefully into my bowels it feels like some of those deep tissues in my pelvic floor get pulled and massaged and it actually feels good -- nowhere near enough to make me cum, but enough to confuse my system with all these strange mixed signals.

I am swamped by the sensations and his rhythm doesn't leave any space to think, only to feel, and so instinctively I do what I'd always done when Coach Rye stretched me -- I relax into the pain, open myself to it, to him, lose myself to his touch and to his demands from my body. I hear my mantra playing itself over and over in my mind in perfect sync with Rye's thrusts.

He thinks I can do this. I can do this. He thinks I can do this. I can do this.

Time ceases to exist and I find myself in a semi-conscious space where there is nothing but sensation and I let myself dissolve into it, succumb to it, fully submitting to the pain surrounding me, pounding into me, filling me. Dimly I recognize and welcome the sounds of our bodies slapping wetly together and our breaths coming out in short, shallow gasps.

I don't exist anymore, all I am is a bundle of acute sensations floating, rocking, rising and flowing in time to his fucking. I want to stay like this forever...




Sensing my withdrawal Coach Rye slows his movements and bends down to speak directly in my ear.

"This isn't a reward Annie. Don't you dare cum. This is the price you pay for not being honest in a session with me. You'll do well to remember this, or next time I will add alligator clamps to your nipples..."

And with that he reaches down below me to painfully pull, pinch and twist my hard red nipples, holding them tightly clinched between thumbs and forefingers as he resumes his hard rimming of my ass.

Jostled out of my sub-space I am suddenly overwhelmed by it all and start crying, my choked sobs absorbed by the cotton gag.

This fucking hurts!

Soon tears and snot start pooling in my nose and it's getting hard to breathe. I can't breathe... I can't breathe! All of a sudden panic sneaks over me to grab me fully in its clutches and I start struggling with all of my might, bucking violently and kicking and screaming through my gag.


It takes Rye a moment to realize something is actually wrong, but by my third scream I feel him go completely still behind me and then pull out immediately, all the way out.

With his left arm he holds me tight to keep me from hurting myself in my frantic struggles, and with a single tug of his right hand the knot at the back of my head releases and my gag slackens and I hear Coach Rye speak quietly and urgently right into my ear.

"Holy FUCK, Annie, STOP. Stop NOW. I gotcha. It's all right, you can breathe. Shhh... you can breathe."

With jerky, shaky movements he pulls the terry gag completely out of my mouth and throws it away onto the floor in front of me.

"There, you can breathe. Take deep breaths for me Annie. I gotcha, it's all right... shhhh... it's all right. Breathe Annie... Shhhh... Just breathe."

I gulp and cough and sputter until I catch my first few deep breaths. Gradually my panic subsides to the point that I stop struggling and instead I go limp, leaning back against his chest, still kneeling on the chair. The forgotten lipstick tube rolls out from between my listless fingers and lands on the carpet with a small 'thunk'. I can only focus on filling my lungs with air, over and over again.

Rye leans back just a little to tug at my wrists and free my arms from behind my back and he brings them forward to rest on the back of the chair and starts to slowly rub my neck and shoulders.

"That's it Annie... in through your nose, out through your mouth, sweetheart, slowly... Shhhhh.... It's all right. I gotcha. It's all right..."

Coach Rye keeps murmuring reassurances in my ear, his palms soothing and gentle on my back. Suddenly I get a flashback from our years training together to one of the many times he'd caught me flying off the top uneven bar after missing a new maneuver I was trying to learn, how he'd saved me from what was surely going to be a nasty fall and told me the same thing over and over as he held me securely in his arms. I gotcha Annie. I gotcha, it's all right.

This is Coach Rye. He'd always kept me safe. I know he's going to keep me safe.

Suddenly I am swamped with embarrassment at my outburst and a huge sense of failure washes over me. I couldn't do it. He thought that I could, but I couldn't. I've failed him. I've failed him miserably. The tears come again and this time they won't stop; big fat tears rolling down my face.

Coach Rye steps back and pulls me away from the chair, sits down, and pulls me onto his lap to cradle me in his arms, my head resting on his chest, tucked under his chin. I feel him kissing the top of my head and my sense of despair and failure intensifies, my sobs coming from the depth of my soul and wracking through my body, my warm tears dampening his bare skin.

"Shhhhhh... it's all right Annie... it's all right..."

His trying to comfort me only makes me feel worse and I try speaking between my sobs:

"I a-am s-so sorry! Y-you thought I-I c-could d-do it and I-I just p-panicked! I am s-so sorry and I feel so ash-ashamed o-of myself f-for failing y-you..."

I cry hard into his chest unable to look him in the eye. I feel his hand cupping my chin and pushing my head back and in the next moment his lips find mine and he kisses me tenderly -- which confuses me enough to stifle my crying. Once I quieten down to the occasional hiccup he leans back and cradles my face in his palms again and I know I'll need to meet his gaze, like it or not.

"Annie, sweetheart... You are so not the one who should be apologizing here. I pushed you too hard. Way too hard. I got carried away, sweetie. I'm the one who's sorry."

I shake my head, even more confused -- I'm still stuck in my sense of failure and shame so I can't quite grasp what he's telling me, but the stricken look on his face twists at my guts even more. Without thinking I try to reciprocate the comfort he'd given me a moment ago and reach up to cup his face and place a soft, careful kiss on his lips.

"It's all right, Rye. It's okay."

Rye half-smiles at me and shakes his head, wrapping his arms around me to hold me close, breathing in my scent before speaking again into my hair.

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