https://pornfaze.com/tags/headmistress-mackenzie/ Sun 10 May 2026 17:53:36 +0200 https://pornfaze.com/videos/5777076/ivy-headmistress-you-will-apologise-while-jerking-off-ejaculating/
Ivy and headmistress have just got back from riding on your estate and when they arrive in headmistress’s office they are still wearing their tight jodhpurs. they are slightly surprised to see you and when they learn why you are here they are outraged. apparently your butler has accused ivy of stealing from you! headmistress is not impressed that anyone dare accuse any of her students of such a thing. headmistress will make you apologise for such an accusation and they both start to manipulate and tease while ordering you to get your cock out and start jerking, which you do without question. while you jerk your cock to them you apologise again and again and, knowing they control you, they seal the deal as headmistress takes you in hand and makes you blow your load all over ivy’s big tits. ]]> Sun 25 Feb 2024 04:41:16 +0200 https://pornfaze.com/videos/5777076/ivy-headmistress-you-will-apologise-while-jerking-off-ejaculating/ https://pornfaze.com/videos/4822069/headmistress-her-cute-student-pixiee-make-you-cum-without-touch/
You have tried to do a naked streak through a st mackenzie’s netball match, however you were easily caught and now pixiee has brought you to see headmistress to be punished accordingly. you stand naked in front of headmistress, who is dressed in sexy satin, and pixiee, who is still wearing her cute little netball kit, with your hands cupped over your stiffening cock. you are told to move your hands and put them behind your back, headmistress wants to see what exactly you were so happy to show off as you streaked. pixiee giggles while headmistress explains how you will now be made to cum, as you stand in front of them. they will both tease you to such an extent you will blow your load and empty your balls without even touching your cock. then you will be walked through the school still naked and covered in your own spunk. ]]> Fri 18 Aug 2023 22:36:13 +0200 https://pornfaze.com/videos/4822069/headmistress-her-cute-student-pixiee-make-you-cum-without-touch/ https://pornfaze.com/videos/4732586/cum-without-touch-as-i-destroy-my-pantyhose/
I have stupidly agreed to oversee a few st hugh’s detentions, the things i will agree to for your alpha male headmaster, well he is the most amazing fuck. today it is only you in detention and i can feel that your eyes are heavily on me. are you wishing you could fuck me? what an erotic thought for you, imagining bending me over the desk, an older woman and a teacher, to show me what a ‘man’ you are. your most intense fantasy. while you fantasise i run my hands over my pantyhose, but oh no! i have a long ladder on the back of my curvy thigh! how frustrating. while i fiddle with the ladder wondering what to do i can tell you are excited. so what is it that is arousing you? my pantyhose, the ladder creeping down my luscious legs, seeing my panties as i bend over or all of the aforementioned? seeing your arousal i cannot help but feed your excitement, it will definitely make the detention more interesting. i start to tear into my pantyhose, creating more ladders and ripping big holes. the more i tear the more you can see and your excitement grows and grows, especially as i open my legs wide to tear the gusset. soon  my pantyhose are shredded but with your cock bulging you are too close, there is no going back and you blow your load, without even touching your cock. how embarrassing for you! f0693 ]]> Wed 09 Aug 2023 13:21:27 +0200 https://pornfaze.com/videos/4732586/cum-without-touch-as-i-destroy-my-pantyhose/ https://pornfaze.com/videos/4732570/cruelly-tormenting-you-your-tiny-dick-with-matron-kay/
You have been caught with your accomplice, donkey dick, streaking once again. now you both stand in front of myself and matron kay. you look as pathetic as ever, mr puniverse, sheepish and worried about what is to come. whereas donkey dick looks smug and confident. i know this was more than likely donkey’s idea, after all he knows he can get you to do anything he asks. you really are the opposite ends of the male spectrum. donkey dick being a top student at st hugh’s, incredibly handsome, tall and tanned with the body of a greek god, oozing confidence and a big swinging dick adding to his alpha male presence. you on the other hand are short, below average intelligence, weedy, pale and worst of all you are hung like a micro carrot and two petit pois! donkey knows when he pulls these stupid pranks he will have all my students and teachers watching closely imagining what they could do with him if alone. whereas you are just the pathetic jester that follows for all to laugh at. it is common knowledge that donkey has an obsession with myself meaning he cannot stay away. you also have an obsession with me so you agree to join him even though you know you will be ridiculed. now you are both alone with myself and matron we plan to humiliate you further, but not only will we laugh at your tiny dick and remind you how no woman will ever fuck you, but we have an even worse torment planned. we will break your heart as you have to watch and hear us fawn all over donkey. we will stroke and caress his big cock, matron will even strip naked and suck on his length before reversing on to him as he fucks both of her holes while you surgently look forward. she will of course show you her fucked holes as she bends over in front of you. no matter how hard you try you cannot stop your tiny dick getting hard which just causes even more amusement. however as we torment you matron and myself realise we both want to fuck donkey, but you will have to face the wall to make sure you do not get to see our full on threesome. all you can do is listen as he pleasures us both, the threesome you can only ever dream of knowing your tiny dick is incapable of giving pleasure! f0634 ]]> Wed 09 Aug 2023 13:21:00 +0200 https://pornfaze.com/videos/4732570/cruelly-tormenting-you-your-tiny-dick-with-matron-kay/ https://pornfaze.com/videos/4597060/fucking-your-virgin-ass-with-my-strap-on/
Ready to rent (part 4): you are back to see me for your final session before your first client. i need to make sure you can really take a cock in your tight virgin asshole without any issues. your first client will have bid on your virgin ass and will be paying a vast amount so you need to make sure you are ready to please. you please your client and you please me, your one and only mistress. you know this is the only way you can satisfy me as i rent you out to anyone and keeping all the money you earn. most of your clients will be men so as a straight male this is hard for you, but if it pleases me you will do it and do it well. i slip on my strap on and bend you over my desk. you will look deep into my blue eyes as i spread your ass and penetrate your asshole for the first time, sliding it all the way in. don’t worry i will be gentle… to start with anyhow! as i fuck your ass you take it well, i can see you are rock hard which creates many questions. are you hard because you are secretly bisexual, because you are aroused at the thought of taking your first clients cock and pleasing me or is it as you gaze into my eyes as i fuck your ass with a strap on? whichever it is i can see your cock straining and your balls tighten. you had better not cum without my permission! if you do you will be made to lick it all up! f0714 check out the following clip(s) from the same series: ]]> Sat 15 Jul 2023 11:11:24 +0200 https://pornfaze.com/videos/4597060/fucking-your-virgin-ass-with-my-strap-on/ https://pornfaze.com/videos/4561720/made-to-piss-your-pants-jerk-off-on-stage/
You have  been caught in the girls toilets, not only is this inappropriate because you are male but also this is an all girls school! still in your st hugh’s boys school uniform there is no hiding where you are from but that will not stop me punishing you accordingly. worst of all not only were you in the toilets but you were standing on a toilet basin to peer over the divider into the next cubical. you said you were just going to go to the toilet but with your trousers unzipped and your cock hard it was obvious what you were hoping to see. you wanted to watch a girl piss didn’t you?! you disgusting pervert, how dare you invade my girls privacy in this way. you will be punished in the most fitting way and now you are on stage for my school assembly, in front of all my girls and staff members. i explain how you have been bound in my office and not allowed to use a toilet. i have also been making you drink endless bottles of water. you have taken on litre after litre and i know your bladder is fit to burst. now you are on stage you stare at me shifting your weight from one foot to the other. everyone can tell you are desperate to pee and i torment you as i slosh around my water bottle while talking to you about the relief you must be desperate to feel. the relief of making it to a toilet and letting go. you desperately do not want to pee your pants on stage, that would be so humiliating in front of everyone at st mackenzie’s, but as my cruel torment continues i can see a small wet patch start to appear on your trousers and it rapidly grows down your legs as a puddle forms at your feet. you pathetic pee pants! i will make you do a walk of shame in your wet trousers and squishy shoes, back to your school where they will also bully and humiliate you, but i have not quite finished yet. seeing as you were planning to jerk off over one of my girls peeing i will now let you masturbate here and now, up on stage in front of everyone. you will jerk off and cum onto your pissy pants and trousers, spraying your massive load all over yourself. when your balls are empty you will stay on stage as your trousers grow cold and wet with the cum soaking into your mess. from now on you will be known only as ‘pissy cum pants’ forever so you had better start stroking hard and fast! f0691 ]]> Thu 13 Jul 2023 20:33:37 +0200 https://pornfaze.com/videos/4561720/made-to-piss-your-pants-jerk-off-on-stage/ https://pornfaze.com/videos/4561681/worshipping-my-beautiful-thigh-high-satin-stiletto-boots/
Satin slavery (part 3): it is time as my satin slave you learned to be useful and today you will worship and clean my thigh high satin stiletto boots. i remind you why you are my obedient satin slave as i show you my sexy satin covered body before drawing your attention to my perfect boots. i explain how you will suck the slim elegant heel and lick the soles clean. i may even let you touch the lower part of my legs of which the satin boots cover. i call you closer and order you to your knees. i hope your tongue is feeling strong and you are ready because i expect only the best for my boots and from my dedicated satin slave. f0708 check out the following clip(s) from the same series: ]]> Thu 13 Jul 2023 20:32:21 +0200 https://pornfaze.com/videos/4561681/worshipping-my-beautiful-thigh-high-satin-stiletto-boots/ https://pornfaze.com/videos/4561665/wearing-satin-gloves-making-you-cum-repeatedly-with-miss-lalay/
Miss lalay has been kind enough to agree to give you out of hours special tutoring to help you through your exams. st mackenzie’s are being paid a lot to have you over here but it is still a blight on miss lalay’s time. however you have not been quiet and obedient in your lessons, in fact you have been somewhat of a gobshite. you seem to believe that because miss is a woman she is interested in you… she isn’t and she decided dealing with you would be a job for the both of us. so she has brought you to my office. now you are looking less cocky as you stand in front of us both. you are just like all the other mouthy st hugh’s boys, all talk with no backbone. knowing you have a thing for satin we both slip on a pair of satin gloves, you might think this is a good thing but i assure you it is not. i order you to get your cock out. you look surprised and start to get aroused but when i handcuff your hands behind your back and gag you with more satin gloves i can see the fear in your eyes. we grab your rock hard cock and jerk you off vigorously, you will cum for us as fast as you can, this is functional not enjoyable. you soon cum, proving you are nothing like a real man, but now it will become increasingly uncomfortable and soon very painful as we take it in turns to cruelly make you hard enough to cum repeatedly, as many as five times in total! you may not think this possible but we have out ways and by the end you will never want to cum again as your cock throbs unbearably and your balls shrivel away to nothing. f0653 ]]> Thu 13 Jul 2023 20:31:47 +0200 https://pornfaze.com/videos/4561665/wearing-satin-gloves-making-you-cum-repeatedly-with-miss-lalay/ https://pornfaze.com/videos/4561599/allowing-you-to-cum-to-my-pvc-shorts-after-repeated-edging/
My dedicated pvc slave, you have been a good boy and obeyed my command to not jerk off as you worship me in my pvc. well at least i hope you have obeyed me! assuming you have  been an obedient pvc slave i am going to allow you to cum to my pvc today. i am wearing my usual pvc over the knee boots and naughty high waisted pvc shorts. they are very tight and my ass looks amazing. however it is not going to be a quick release. even though you have been waiting for this moment for a while i will make you edge over and over while i tease you with my pvc ass and pvc covered gusset, not to mention my legs in pvc boots. as i encourage you to stroke you will make sure you stay in control, you would not want to disappoint your pvc goddess would you? especially when i am expecting a large load exactly when i command! f0688 ]]> Thu 13 Jul 2023 20:30:27 +0200 https://pornfaze.com/videos/4561599/allowing-you-to-cum-to-my-pvc-shorts-after-repeated-edging/ https://pornfaze.com/videos/4547790/made-to-suck-my-strap-on-take-it-deep/
Ready to rent (part 3): you are back to see me for your next session to make sure you are ready to rent. you will be the perfect rent boy because you want to please me and earn me large sums of money. it is the only way you can satisfy me, by allowing me to rent out your body. today i need to make sure you can take a decent sized dick in your mouth and suck it with enthusiasm, to take it down your throat and gag on it while drooling like a good boy. with the bids rolling in for your anal virginity you need to make sure you are the perfect lay for whichever guy pays the biggest fee, and those fees for your ass just keep growing! part of this will mean sucking cock well so now it is time to practise. you will have to suck all sizes of cock, big, small and average. so today i have a slightly larger than average size strap-on cock to test you. as i slip off my satin skirt and slide the strap on over my pantyhose i can tell you are apprehensive, and so you should be. when i order you to your knees you obey and you open your mouth wide and start sucking, but will you get hard, and if you do is it because you are secretly bisexual or because you know you are pleasing headmistress?! f0713 check out the following clip(s) from the same series: ]]> Thu 13 Jul 2023 08:09:22 +0200 https://pornfaze.com/videos/4547790/made-to-suck-my-strap-on-take-it-deep/ https://pornfaze.com/videos/4524164/sexy-headmistress-mackenzie-strips-relentlessly-tickles-cute-lily/
Lily has been sent out of her gym class for not trying and sent to see the headmistress. miss tells her how she must try in her gym class, it is very important for her to stay fit even if she does not enjoy it. lily is being very grumpy about having to go to gym class so headmistress starts to tickle her to make her smile. lily cannot help laughing and wriggling underneath headmistress’s fingers and when miss starts to slip off lily’s gym kit lily begs for her to stop tickling. miss explains how every time lily is sent out of gym she will be tickled as a punishment, plus it will also be a good workout for her as she wiggles around. lily tries to resist but when she is completely naked, with her legs spread and  having her feet tickled she caves in and says she will try harder in her gym class just to make the tickling to stop. ]]> Wed 12 Jul 2023 07:22:24 +0200 https://pornfaze.com/videos/4524164/sexy-headmistress-mackenzie-strips-relentlessly-tickles-cute-lily/ https://pornfaze.com/videos/3898730/look-in-to-my-eyes-while-i-finger-your-tight-ass/
Ready to rent (part 2): you are back in my office so we can start the process of turning you into an elite high class rent boy. your infatuation with me is so deep that you will do anything to please. you cannot please me sexually and have no money of your own so i will have to put you out to rent to other men (and maybe the occasional woman) and i will take all the money you earn. even though you are entirely straight you know this is your only option to satisfy me and spend time with me. so today is another step closer to starting the process. i have already used previously taken pictures to advertise you and your anal virginity, plus there is now bidding on who will take your virginity and the bids are already sky rocketing. you will make me extra rich! the first step is to loosen that tight ass hole and today i will be fingering your ass to loosen you up and get you used to being penetrated. i will start with one finger, then two and then three and finger fuck your ass gently. the whole time you will look deep into my blue grey eyes and be reminded why you are allowing me to put you out to rent like a naughty little anal fuck slut. the real question is will you get erect, and if you do is it because i am fingering your ass or are you actually excited by the thought of being fucked by a man to please me?! f0712 check out the following clip(s) from the same series: ]]> Thu 27 Apr 2023 22:13:11 +0200 https://pornfaze.com/videos/3898730/look-in-to-my-eyes-while-i-finger-your-tight-ass/