https://www.freepornflix.com/sites/miss-ruby-marks/ Sat, 02 May 2026 07:42:18 UTC https://www.freepornflix.com/video/892590/aroused-boys-are-easily-distracted-a-firm-hand-and-a-hard-cane-for-a-fast-fix-1080-hd-miss-ruby-marks-caning-english-corporal-punishment-traditional-victorian-punishment-domestic-discipline-scolding-corner-time-otk-spanking/
Miss ruby is responsible for keeping many boys in line. and she finds them to be easily aroused without thought. aroused boys are also easily distracted and it takes a firm had to keep them in check. luckily miss ruby is well known to have one of the firmest hands around and she will always be ready to put it to good use. she has been sent a slave by miss m, whose slave husband has been sent over to be disciplined, and used as miss ruby wishes. bent over before bed for 6 of the best - 6 hard strokes land upon his backside before he's put in the corner with a very traditional english punishment - corner time with a victorian backboard to keep him standing straight. miss ruby is a cruel sadist though and she teases and torments her slave, causing him to become more aroused in his cock cage - he is sent to her fully caged and is permanently denied. and when his corner time is over she still feels like he's in need of a sharp reminder to stay in check; so she has him lay over her knee for a good, hard spanking. a hard hand spanking and a hard paddling with an ironically cruel book.    he is spanked so hard, her own hand is bright red, glowing from the effort and symbiotic exchange. a beautifully karmic punishment. but this does not deter miss ruby who spanks him yet harder. in fact her throbbing hand only seems to make her go harder on the slave's bottom. and she still continues to tease him, stroke his behind and turn him on even more, thus increasing his punishment. his moans are a mixture of ecstasy and agony as he submits fully to the occasion. and when asked he of course cannot say he is not aroused. her long nails scratching into his hot, red behind.  ]]> Wed, 29 Apr 2026 13:06:19 UTC https://www.freepornflix.com/video/892590/aroused-boys-are-easily-distracted-a-firm-hand-and-a-hard-cane-for-a-fast-fix-1080-hd-miss-ruby-marks-caning-english-corporal-punishment-traditional-victorian-punishment-domestic-discipline-scolding-corner-time-otk-spanking/ https://www.freepornflix.com/video/866672/exquisitely-spanked-1080-hd-miss-ruby-marks-spanking-otk-paddling-bath-brush-panty-sniffing-human-furniture-cfnm/
Miss ruby has had the slave husband of miss m sent to her again. he is of course a very willing, locked submissive who becomes her property for the whole weekend. he is spanked softly at first, building to a blistering intense spanking that not only turns his bottom red but it turns miss ruby's hand red in the beautiful symbiotic relationship that is a hard spanking. exquisitely beautiful, miss ruby looks stunning in her negligee and her blonde hair long and shiny - slave p submits across her knee as she spanks and paddles him. as the punishment finishes she has him inhale her scent from her panties, increasing his desire and his frustration from his chastity cage. filling his head with nothing but her pheromones and the dream of an orgasm he will never have. ]]> Fri, 17 Apr 2026 11:14:07 UTC https://www.freepornflix.com/video/866672/exquisitely-spanked-1080-hd-miss-ruby-marks-spanking-otk-paddling-bath-brush-panty-sniffing-human-furniture-cfnm/ https://www.freepornflix.com/video/828202/pounded-in-her-pussy-for-60-minutes-straight-1080-hd-miss-ruby-marks-milf-lesbian-domination-big-dicks-cougar-femdom-sex/
Miss ruby has waited to make the most epic pussy pounding clip for a whole year nearly - last year back from her martial arts training she realised her stamina had increased ten fold and she could bang marlie into the bed for as long as marlie's pussy could take it. but one thing led to another and a whole year has gone by without making the clip! however miss ruby has just returned from yet another trip for martial arts training and she can bang even harder now - and this time marlie doesn't escape so easily. looking gorgeous in her beautiful drawing room, miss ruby bends marlie over the chaise longue and proceeds to pound her pussy, long and hard and very deep. using bigger and bigger dicks and filling her face and her pussy.... and even turning her face intoa  pussy with a fabulous fleshlight gag..... there's no escaping the dick for marlie - not that she'd want to! spanked, paddled and bruised it's 60 minutes of none stop hard fucking! ]]> Tue, 10 Mar 2026 12:27:07 UTC https://www.freepornflix.com/video/828202/pounded-in-her-pussy-for-60-minutes-straight-1080-hd-miss-ruby-marks-milf-lesbian-domination-big-dicks-cougar-femdom-sex/ https://www.freepornflix.com/video/817930/a-merciless-mouthsoaping-wmv-miss-ruby-marks-mistress-baton-blonde-dominatrix-cfnm-femdom-prison-play-spit/
Prisoners 971 and 972 have been seen dick sucking on the femdom prison cctv. not only that but neither of them can stop swearing and so the wardens mistress baton and miss ruby marks decide on a disgusting punishment, they must instead suck the dick soap, a gruesomely tasting soap that soon has them spitting and wretching on the floor. but we're not finisihed yet, next we carry on scrubbing their filthy tongues with carbolic soap. the traditional english punishment still works the best when it comes to foul mouthed cellmates. am indescribably horrible taste that eventually numbs the mouth but still doesn't take the taste away - for days after the memory will be fresh in the minds and mouths.   this is the full 4k version. to buy this clip in 1080 hd for a smaller file size see here   more mouth soaping clips: marlie chokes on soap strict teachers bully the brats soaped & sodomised wash her filthy mouth out caned across the tits and thighs doxy denial ]]> Fri, 06 Mar 2026 10:43:57 UTC https://www.freepornflix.com/video/817930/a-merciless-mouthsoaping-wmv-miss-ruby-marks-mistress-baton-blonde-dominatrix-cfnm-femdom-prison-play-spit/ https://www.freepornflix.com/video/817903/every-hole-apart-from-the-one-she-wants-1080-hd-milf-lesbian-domination-throat-fucking-anal-hair-pulling/
Back from their holidays, miss ruby is finally able to give marlie some much needed dick. it was offered to her the night before but she decided to wait until she could get fucked properly the next day. only the next day arrives and marlie's body betrays her..... pussy is off limits... but of course she has more holes! and miss ruby wants to fuck her slave. it's time for marlie to get throat fucked and butt fucked until miss ruby is satisfied. she can even sulk whilst it happens - miss ruby doesn't care. face slapped, hair pulled, holes filled - every hole apart from the one she wants! ]]> Fri, 06 Mar 2026 10:42:45 UTC https://www.freepornflix.com/video/817903/every-hole-apart-from-the-one-she-wants-1080-hd-milf-lesbian-domination-throat-fucking-anal-hair-pulling/ https://www.freepornflix.com/video/808674/marked-by-a-milf-1080-hd-lesbian-domination-hand-tawsing-brat-girl-punishments-older-woman/
Mmmljhgv ]]> Mon, 02 Mar 2026 10:31:31 UTC https://www.freepornflix.com/video/808674/marked-by-a-milf-1080-hd-lesbian-domination-hand-tawsing-brat-girl-punishments-older-woman/ https://www.freepornflix.com/video/776444/beaten-belted-caned-and-finger-fucked-1080-hd-miss-ruby-marks-lesbian-domination-corporal-punishment-brat-girls-milf-scolding-disciplinarian/
There is one major problem when it comes to long distance servitude - particularly when the one serving is a spoiled princess and huge brat. the issue is that the punishment list becomes so long, it’s a question of how on earth does miss ruby’s marks deal with it. and what a list to deal with. angelica had a little shopping issue and now has to face the consequences of her spending. the penalty? a long blistering scolding from miss ruby, (something no one ever wants to be on the receiving end of). the scolding was swiftly followed by a very hard, cold caning. but that isn’t it; miss ruby then drags her over her knee, beats her with a now infamous bath brush continuing to scold her. this is followed by a hard belting on the bed and an equally hard finger fucking (for my innocent and rarely touched, good little catholic dolly, this isn’t the hot and horny experience for her that you might be imagining).   the only silver lining is that as always miss ruby gives a beautiful and viscerally cruel scolding and looks stunning whenever she is this angry - not much fun to be on the receiving end, but it's extremely enjoyable to watch; no wonder these clips with miss ruby's owned bratty dollies and their dollhouse escapades are always miss ruby's best selling clips. dressed in an elegant silk jumpsuit and gorgeous designer stilettos, miss ruby once again delivers harsh discipline with style and elegance. will angelica learn her lesson, or will miss ruby need to keep a close eye on her spending habits from afar? one thing is certain, this young lady's bottom will definitely be sore for a while. ]]> Tue, 17 Feb 2026 10:12:24 UTC https://www.freepornflix.com/video/776444/beaten-belted-caned-and-finger-fucked-1080-hd-miss-ruby-marks-lesbian-domination-corporal-punishment-brat-girls-milf-scolding-disciplinarian/ https://www.freepornflix.com/video/775364/the-shorter-my-skirt-the-harder-i-cane-1080-hd-miss-ruby-marks-caning-corporal-punishment-tease/
Miss ruby marks has long since noticed that whenever she has someone bent over for a caning, the person being caned just can’t seem to help themselves to take a peek at her legs or feet - particularly when things start to get painful. it appears to be a little loophole of pleasure for them to cope with this cruel and especially painful punishment. anyone who has ever been bent over to be caned will tell you that this is the most painful punishment to endure. a fear enduring moment that leaves most people sweating; when the cane hits, it will take anyone’s breath away as they try to deal with the shock and heat that course through their body as they feel the welt rising. all of these things of course feed a sadist’s desire for pain and suffering. any attempt to avoid this level of pain or lessen it’s severity takes away miss ruby’s pleasure and therefore diminishes the affectiveness of it meeting her sadistic needs. and so miss ruby has decided to close this loophole and has devised a way to have this tactic cause more pain - the shorter her skirt, the harder she’ll cane. kevin must find a way to endure the harder and harder strokes miss ruby delivers with her traditional whangee cane. a particularly painful implement due to the natural ridges that occur in the rattan, creating knots the whole length down. and she teases kevin mercilessly, not only changing into shorter and shorter skirts but also caning him in just her lingerie has she delivers her signature style of extremely hard unrelenting strokes on his backside. her accuracy meaning that each stroke lands where she wants it to; sometimes landing stroke after stroke in the exact same spot. her outfits only add to the beautiful scene. miss ruby smiles as only she can, her joy and happiness whilst she delivers unmet cruelty is well known. any submissive or slave who has bent over infront of her, know the feeling and moment of submission when they know truly and deeply that they would allow her to do anything so long as she smiles at them with true joy whilst she does it. after finishing a fearsome and extremely hard caning, miss ruby’s is not yet done, she will now drag kevin over her knee as she is dressed in vintage lingerie, sat on her chaise longue. producing a vicious and much hated bath brush, she proceeds to beat him hard upon his already sore and punished bottom. when she is finally satisfied miss ruby allows kevin to rub her sore feet as she relaxes. ]]> Mon, 16 Feb 2026 11:40:51 UTC https://www.freepornflix.com/video/775364/the-shorter-my-skirt-the-harder-i-cane-1080-hd-miss-ruby-marks-caning-corporal-punishment-tease/ https://www.freepornflix.com/video/733713/corporate-cougar-spanks-her-employee-for-office-morale-boosting-activity-1080-hd/
I've been sent an employee who seems a bit down in the dumps and i decide to boost his energy and morale by delivering a nice therapeutic spanking by hand and with all my implements. over my knee, dressed in my suit and silk blouse it's not hard to see why i favour this method for morale boosting in the corporate office... i'm sure this employee's productivity will be back to it's usual high level in no time! ]]> Thu, 29 Jan 2026 11:20:31 UTC https://www.freepornflix.com/video/733713/corporate-cougar-spanks-her-employee-for-office-morale-boosting-activity-1080-hd/ https://www.freepornflix.com/video/731066/bitch-boss-pegs-him-for-punishment-1080-hd-miss-ruby-marks-office-domination-mini-skirts-pegging-strap-on-femdom/
Called into the office for multiple complaints from female staff members. the femdom office of administration doesn't take such accusations lightly and decides that this boy must have a taste of his own medicine and experience what bullying harassment actually feels like, both inside and out. bent over the desk he finds himself legs spread. and a pastel pink dick is suddenly filling up his once unused hole. the employee feels at once embarrassed but insanely turned on - he could never admit that to his bitch boss though. especially not when she towers over him in heels and stockings and that mini skirt. the intimidating look in her eye always brings him to his knees mentally. and now she's going to own his arsehole too - could this day at the office get any worse?  ]]> Wed, 28 Jan 2026 10:47:46 UTC https://www.freepornflix.com/video/731066/bitch-boss-pegs-him-for-punishment-1080-hd-miss-ruby-marks-office-domination-mini-skirts-pegging-strap-on-femdom/ https://www.freepornflix.com/video/728164/helpless-gooner-gets-what-she-deserves-1080hd-miss-ruby-marks-fetters-wheel-huge-labia-extreme-bondage-multiple-orgasms-lesbian-domination/
Marlie has been turned into a slave for the summer - a self professed princess and brat girl, she misbehaved and attracted the ire of miss ruby to the point that her dolly status was revoked and she was turned into a mindless slave. and there's one thing this slave definitely does really well - she's become an unstoppable gooner for all things miss ruby.  ]]> Tue, 27 Jan 2026 10:23:26 UTC https://www.freepornflix.com/video/728164/helpless-gooner-gets-what-she-deserves-1080hd-miss-ruby-marks-fetters-wheel-huge-labia-extreme-bondage-multiple-orgasms-lesbian-domination/ https://www.freepornflix.com/video/726369/a-corrective-caning-class-dismissed-1080-hd-miss-ruby-marks-school-role-play-teacher-fetish-punishment/
At miss ruby's cruel school for boisterous brats, discipline is the order of the day. these 3 students got themselves into all kinds of trouble earlier in the day; messing around, putting their feet on the desks, writing in miss ruby's punishment book, wearing her teachers gown and having a very disorderly food fight. and so miss victoria and miss ruby decide enough is enough - it's time to deliver a severe punishment. a cruel and corrective caning. 24 strokes for each student. both miss victoria and miss ruby deliver harsh strokes across the bared backsides of these naughty students.      ]]> Mon, 26 Jan 2026 10:59:50 UTC https://www.freepornflix.com/video/726369/a-corrective-caning-class-dismissed-1080-hd-miss-ruby-marks-school-role-play-teacher-fetish-punishment/