Doing Dirty Debbie

Story Info
Punishment and messy anal.
2.5k words
4.2
108.7k
44

Part 1 of the 5 part series

Updated 10/30/2022
Created 11/01/2009
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jpb209
jpb209
57 Followers

I need to introduce you to Debbie. A natural submissive and pain slut who I became involved with a few years ago.

She is in her early forties and has a perfect hourglass figure. A twenty six inch waist, thirty four inch hips and a beautiful thirty eight C pair of tits. Not firm, but big floppies, soft, malleable and perfect for torture. You can work her tits for ever, the more you do the more turned on she becomes. Hard pinching and vicious twisting, whips, clamps, paddles – they leave her sore and bruised but she just comes back for more. When her nipples are so sore she can barely put her bra on, she'll be twisting them herself when she rubs herself off only a few hours after I have finished with her.

Her ass is soft and malleable. It reddens up beautifully under any assault – hand, paddle, flogger, whip, cane, she can handle them all. Not much bigger than you can grab with one hand, but she thinks its too big. She gets off on the mental scene in a big way so telling her it is a huge flabby ass will cause her pure mortification as I spank and paddle her.

She never screams or cries – far too tough for that. A smart ass sub who is proud of the pain she can take and wants to be humiliated and degraded. She does though have one lovely mental block. Her asshole. Now she buggers beautifully – 15 minutes without complaint easily, all moans, orgasms and encouragement, but try to examine her hole up close or insert things in it or make her perform her toilet in front of you and she is mortified. She will try anything to get out of it – her conscious mind is repelled and disgusted, her subconscious wants the humiliation. A wonderful quandary to be exploited.

We meet at our usual motel. She gets there first and undresses down to her black panties and lies on the bed with a half smile on her face and her tits hanging down. Brown nipples – not that big, just big enough for clamps.

I walk in and undress silently. "Stand up bitch," I say and she pouts, rising to her feet slowly. I slap her face – twice on each side. "When I say move, you fucking move you stupid cunt," I tell her. I grab her nipples and squeeze hard and twist. I pull up on her tits, making her stand on tiptoe. I relax then squeeze and twist some more before finally pulling down on her nipples to make her get to her knees. My cock is in front of her face and she can smell it. My foreskin and cock reek of stale piss – I smear it on earlier in the day and now she puts her tongue out to slowly lick it clean. Only when it is clean do I allow her to get it all in her mouth as she loves, then grab her hair on either side and pull her onto me, fucking her face, pulling her hair and slapping her face occasionally.

I reach down and yank on her nipples commanding her to stand. I turn her around and rip her panties off her. I tell her to bend over and grab her ankles – she complies giving me a shot of her beautiful long graceful legs and her lovely pear shaped ass. I part her ass cheeks and she whimpers – "What are you doing?".

The answer is "Whatever I fucking want you slag," and half a dozen hand whacks on her ass remind her who is in charge. I spit on my middle finger, lightly lubricate her shit hole and stick my finger in. Today I'm in luck – I can feel a piece of shit well up her hole. "I've found some dirt up you, you dirty fuckslut – we're going to have some real fun today".

"Nooooo," she moans, but I yank my finger out quickly, bringing forth a gasp then spit on her hole again and start to shove my cock up her. Enough lubrication to get it up, not enough to make it painless. It sticks in her tight sphincter muscle but a final hard push and it burrows up her gut and she squeals like a pig. She's not used to it up her ass quite this early on. I give it five or six strokes then pull out –a small brown deposit is on the end of my cock, so I turn her round, force her to sit on the bed and tell her to eat her own shit. Her eyes go wild and she shakes her head. A slap to her face then I hold her by the hair with one hand and pinch her nose with the other. Her mouth opens and my cock starts to go in. Keeping a hand on her head to stop her pulling away, I reach down and rub her clit. Now she is caught - this bitch comes quickly and often and only needs a few strokes on her clit to have her come. I shove my cock down her throat as she starts to come and keep telling her she's a shit eating whore. She comes, choking on my shitty cock and I pull it out.

Now I stand her up and start working on her tits. Twisting and pulling her nipples while she quietly gasps. I check her mental state – "Having fun?" she nods and gives a small smile. So I take out one of my whips – rubber strands – and start to hit her tits. I swing from over my shoulder and the whip lands on those big floppy tits with a satisfying thwack each time. As they start to redden and her nipples are now dark brown and engorged, I halt and take out some rope, I make her a tight rope bra – floppies like hers can be roped tight leaving the rest of the tit bulging out – the skin much tighter now. I resume my attack – windmilling the whip repeatedly on each tit until they are both painfully red. After that I bring out a plastic ended spatula and beat her nipples and tits with it. This is designed to leave her bruises to look at for the next week or so until we can meet again. She looks down at her sore tits and I reach down to her shaved cunt, lean her head on my shoulder and rub her off until she comes twice. Now I produce the clamps – put them on then a couple of weights hanging from the chain between them to distort and distend her nipples. I need to make them sore for days yet. I flick the weights and make them jiggle – I turn round and spank her ass as a warm up – just to make those weights pull her sore nipples ever more off her tit. Reach down again – another come then just before she comes I open a clamp and watch the agony on her face as the circulation resumes. I laugh at her expression but then I take the weights off – she breathes a sigh of relief.

I order her to lie back on the bed, face up. I pick up a couple of small whips then kneel and settle over her, facing down her beautiful body. Flat stomach leading to a shaved cunt. Her cunt lips are the smallest I have ever seen – not much there for clamps or clips, but her hole opens and gapes and is so easy to slip my cock into – or anything else for that matter. Her tits are between my thighs and I pull them up with the clamp chain – a few jerks and I get a squeal.

We call this position "Heaven" for good reason. I pull her legs up over my shoulders – in that position her cunt hole is agape, her brown asshole is well in view and my own shit hole is right over her face. The Marquis de Sade once said that the only use for a woman's tongue is to clean a man's arse, so I habitually fail to wipe properly after my morning shit and leave some for Debbie to find and clean. Today is no exception and I slowly lower my smelly and shit streaked arse hole onto her pretty face. "Eat shit you fucking whore," I tell her slamming my hole onto her mouth and starting to whip the inside of her thighs. I feel her tongue start to lick and clean so I whip harder. I feel her stiffen her tongue and try to push it up my hole to clean more. I help by pushing out – "I'm going to shit in your mouth you cunt," I tell her and whip her harder. This is her fear – she can take a little left over, likes the taste, but the idea of anything coming out is too much. "I'm pushing," I tell her and hear her distress – her body tenses and I choose that moment to deliver a blow from the whip straight onto her cunt. It gets her right in the inner meat – no juicy lips on this bitch – all inner red meat to whip. Again and again I descend on her, all the while pushing out as hard as I can with my ass and telling her that I'm going to do it this time. I'm riding her tongue up my ass and now start to whip into her ass hole and ass cleft making her squirm even more.

For her reward I bend down and start to bite her clit – her juices are very mild and so I suck on her cunt, bite her firmly and finally push a finger up her ass and play with that piece of shit and all the while she is trying to keep tonguing and cleaning my ass. Heaven indeed. As she comes I pull the clamps off her tits and she gasps hard but comes and comes until with her exhausted, I rise from my throne. She looks up at me and licks her lips in defiance – then has a swig of water from the bedside table.

I make her get up now and come lean over my knee. Time to be spanked – for being a shit eating slut. I start slowly – two slaps per side, move over, increasing slowly the cadence and force. Her ass cheeks wobble madly as I hit her and I keep telling her what a fat ass she has – that hurts her, she issues denials but I keep right on, smacking and insulting her until her ass is a bright pink. I stop then and reach down to quickly rub her off – the more I do that the harder I can hit. Now the paddle – two hard each side in a quick rhythm. 50 swats is the goal and after the first quick twenty I stop and smooth the furry side of the paddle over her bum cheeks. She wriggles happily, then I turn it over and hit really hard – three per side. She jumps in the air – I rub her off, stroke her then hit again. Now I get her up – hands on the bed and start to hit her as hard as I can. Ten more, then I shove my cock up her cunt – fuck her hard and fast and withdraw. 10 more and another fuck before I reach for our flogger. Four with the flogger – hit from over my shoulder and see the weals appear. Then up her cunt and reach round and rub her off – "Come on my cock you little cunt," I tell her and she does. Out I come and pick the flogger up again – "Whack Fuck" we call this and after the flogger I have one more surprise – a birch length cut that morning. Six hard unyielding cuts into her ass, each one a new bruise and she has a beautiful red bum now – the heat off it is amazing. I fuck her one more time and make her come again before telling her to go get a towel to kneel on.

She comes back meekly and spreads the towel on the bed – kneeling on it with her beautiful red ass stuck up. Still, she must ask for it. "Ask for it", I say – she pauses – I hit her.

"Please fuck me," she says

"Where?" I ask

"In my ass," she says.

"Say shit hole," I say (she hates that term).

She whimpers. "Please fuck my shit hole," she finally whispers. With a quick smear of spit I position my cock before her brown ring and start to push. She opens up beautifully – I get to the edge of her sphincter muscle and then push again – dropping into the empty space behind it. A few strokes and I can now feel the far end of her rectum – it wraps round the end of my cock and I start to bugger her. A minute or so and I pull my cock out to look at her gaping hole – this really embarrasses her "Your shit hole is gaping wide I tell her," and she burrows her head in her pillow in shame. I pull out and push all the way in to stimulate her shitting action – then I go deep with hard thrusts to the far end. I use a new action – I stay still and grab her hips, pulling her back onto me. This way I can use the whole of my shaft without popping out and she feels that much more used. (She will masturbate thinking of this on lonely nights at home). Now I pull out again and there is shit on my cock – brown and smelly. I wipe my cock on her ass cheeks – marking her as a shit slut. I tell her I have hit paydirt and she cringes with embarrassment. I push in and keep pulling out as she covers my cock in shit each time. Next time I pull out she starts to dribble liquid shit – I scoop it up and reach round to smear it on her tits. She gags and moans and I keep plunging in and smearing the results on her ass, her tits and finally all down her back. It has run down her thighs and stained the towel. Now I pull her hard onto my cock ramming up her with all my strength. All she can say is "My God, My God," over and over until I finally shoot my come deep up her smelly rectum.

I push her off me and she lies on her stomach, shit smeared with her gaping asshole bubbling gently and exuding dirt and cum. I go round the bed, grab her by the hair and for one last time, shove my filthy cock in her mouth. She gags and almost retches as she cleans me off and I reach down one more time and bring her off..

Now I need to think up something better for next time!

jpb209
jpb209
57 Followers
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AnonymousAnonymousover 12 years ago
Disgustingly

beautiful.

buttcheeks777buttcheeks777over 12 years ago
Whoa!

I almost came several times reading this dirty, nasty story! Well done. That's what I was sort of going for but I only got negative comments on my first story submission.

I can't wait to read the rest of this nasty series!

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