https://pornfaze.com/tags/headmistress/ Sat 02 May 2026 14:49:16 +0200 https://pornfaze.com/videos/7712865/caned-to-tears-by-miss-olivia-in-detention/
Miss olivia canes a naughty boy who has been put in detention. she severely canes his bare bottom until he cries. once the naughty boy is crying she carries on caning him, while enjoying every cruel stroke that she applies to his upturned bottom. filmed from multiple angles in broadcast quality 4k ]]> Fri 17 Apr 2026 11:54:06 +0200 https://pornfaze.com/videos/7712865/caned-to-tears-by-miss-olivia-in-detention/ https://pornfaze.com/videos/7587663/sent-to-miss-strictland-pt2/
Part 2 headmistress miss strictland severely caning a pupil. she breaks several canes on his bottom while she canes him with such severity to make sure he gets maximum benefit from each and every stroke. this is a severe caning filmfilmed from multiple angles in broadcast quality 4k ]]> Fri 09 Jan 2026 19:47:00 +0200 https://pornfaze.com/videos/7587663/sent-to-miss-strictland-pt2/ https://pornfaze.com/videos/7487772/a-lesson-in-german/
Strict miss stinger is sam johnson's german teacher and sam hasn't done her homework learning german verbs. the strict, sexy school teacher pulls sam across her lap for a sound spanking, first over her white cotton panties and then on her bare bottom. she then uses a leather strap over the knee, before getting sam to stand up and bend over for the cane. she makes sam count in german, which dramatically improves as she is being caned! it's obvious that these 2 ladies have great chemistry and had a lot of fun filming this clip.  ]]> Wed 05 Nov 2025 10:22:28 +0200 https://pornfaze.com/videos/7487772/a-lesson-in-german/ https://pornfaze.com/videos/7470093/terra-mizu-delights-pro-richard-lennox-with-his-own-medicine/
]]> Fri 24 Oct 2025 00:33:10 +0200 https://pornfaze.com/videos/7470093/terra-mizu-delights-pro-richard-lennox-with-his-own-medicine/ https://pornfaze.com/videos/7464085/pegged-at-your-graduation-the-faculty-s-final-exam-headmistress-vivienne-l-amour-fucks-your-hole-and-milks-your-cum-1080p/
You thought you were graduating today, but headmistress vivienne has other plans. dressed in a formal cap and gown, with a sultry secret underneath, i'm not impressed with your academic achievements. to earn your degree, you'll need to prove your obedience and dedication to my every command. get on your knees and prepare to suck my strapon, feeling every inch of it slide down your throat. don't think you're done yet, because next, you'll be taking it from behind. that's right, you'll be getting pegged like a good little student. but that's not all - you'll also be servicing all the female faculty members in the gloryhole, one by one, as they take turns pegging you and asserting their dominance. and while you're at it, jerk off to my instructions. i want to see you stroke that cock, feeling the pleasure and pain as you're dominated by your headmistress and the entire female faculty. will you pass the test and earn your graduation? or will you fail miserably and be held back for another year of discipline and punishment? the choice is yours... but let's be real, you have no choice. graduation day just got a whole lot more... penetrative. ]]> Sun 19 Oct 2025 19:41:27 +0200 https://pornfaze.com/videos/7464085/pegged-at-your-graduation-the-faculty-s-final-exam-headmistress-vivienne-l-amour-fucks-your-hole-and-milks-your-cum-1080p/ https://pornfaze.com/videos/7437039/sent-to-miss-wood-and-caned/
Miss jessica wood severely punishes a naughty boy who has been sent to her for truancy and skipping detention. she administers 2 very severe bare bottom canings and is utterly venomous when applying the cane to his bare bottom. lots of strokes, all administered with the utmost severity.filmed from multiple angles in broadcast quality 4k ]]> Wed 01 Oct 2025 01:41:55 +0200 https://pornfaze.com/videos/7437039/sent-to-miss-wood-and-caned/ https://pornfaze.com/videos/7385937/sent-to-miss-cavendish-again/
Miss rose cavendish taking detention. although she utterly thrashed this naughty boy the last time she saw him, she wanted to repeat it his ordeal because she enjoys caning naughty boys so much. as expected the strict african disciplinarian bares his bottom and canes him very severely.filmed from multiple angles in broadcast quality 4k ]]> Fri 29 Aug 2025 06:56:18 +0200 https://pornfaze.com/videos/7385937/sent-to-miss-cavendish-again/ https://pornfaze.com/videos/7345845/fuck-the-bitch-from-the-headmistress3/
]]> Sat 02 Aug 2025 16:19:28 +0200 https://pornfaze.com/videos/7345845/fuck-the-bitch-from-the-headmistress3/ https://pornfaze.com/videos/7176945/a-swiss-headmistress-and-an-african-professor/
]]> Sat 26 Apr 2025 11:39:51 +0200 https://pornfaze.com/videos/7176945/a-swiss-headmistress-and-an-african-professor/ https://pornfaze.com/videos/7125067/sent-to-miss-olivia-to-be-tawsed-and-caned/
Strict miss olivia deals with a pupil very severely. she tawses his hands hard then bends him over and applies her dragon cane to his bare backside, both times showing no mercy when applying the cruel punishments.filmed from multiple angles in broadcast quality 4k ]]> Mon 31 Mar 2025 11:59:43 +0200 https://pornfaze.com/videos/7125067/sent-to-miss-olivia-to-be-tawsed-and-caned/ https://pornfaze.com/videos/7009128/girls-finishing-adult-school-the-final-test-a-severe-caning/
Lady dark angel has called me into her (the headmistress's) office for my final training. walking in wearing my gingham summer dress. bent over her chair mistress delivers my final punishment. a severe, brutal caning using two extremely harsh canes. head mistress tells me i will be taking as much as she desires. there is no number, she will continue until she feels that i have finally learnt my lesson and can be sent home. instant screams and tears from the canes on my already very sore bottom, before the 5th in and i'm already crying from the pain. but tears are not a safe word. mistress continue to cane harder and harder, the welts raising on my sensitive bottom as i try to cover them with my hands only to be bent back over the chair to receive the neverending list of cane strokes. the pain near unbearable but i want to go home and so must prove how well behaved i am now and take my punishment like a good girl. a very harsh caning clip from lady dark angel leaving me in anguish and agony before i am finally dismissed from her school. ]]> Mon 03 Feb 2025 23:19:47 +0200 https://pornfaze.com/videos/7009128/girls-finishing-adult-school-the-final-test-a-severe-caning/ https://pornfaze.com/videos/6990285/a-lesson-well-learnt/
]]> Sat 25 Jan 2025 02:26:57 +0200 https://pornfaze.com/videos/6990285/a-lesson-well-learnt/