Detention Part Two: DP The Principal Way - GirlsTryAnal
Release Year: 2015
Studio: GirlsTryAnal
Cast: Samantha Rone, Dana DeArmond, Dana Vespoli
Genres: Toys, Blonde, Brunette, Girl on Girl, Hardcore, Threesome, Anal, Natural Tits, Small Tits, Rim Job, Fingering, MILF Mature, Tattoos, Strapon
Video language: English
Poor Samantha Rone cant catch a break...Between sleeping in class and getting detention, the hours pass but didn´t seem to be. It´s a good thing that Samantha has a voluminous imagination to pass the time, and the only thing that will keep her sane in Miss Vespoli´s class. Samantha´s imagination continues to go on a rampart, holding onto her daydreams and memories of Miss Vespoli pleasuring her with anal dildo´s and sleek fingers. Samantha didn´t realize she fell back into reverie, costing her a visit to the Principal, Dana DeArmond. Now Samantha was in for it big time!Samantha enters Miss Dearmond´s office, indifferent to her situation. Samantha only cared about a fantasy world where she could be allured and dominated by her superiors. Miss Dearmond lectured Samantha letting her know her actions were to be punished once again with another detention. Samantha obeys going back to class, but is overcome with exhaustion and overruled with sexual thoughts. This time Samantha didn´t know how far her imagination would go .Samantha´s eyes slowly close, bringing her to a place very familiar to the one she was already in. The principals office. She watched from behind, Miss DeArmond and Miss Vespoli kissing each other half naked on the desk, eager to get in on the action.
Format: mp4
Duration: 27:36
Video: 960x544, AVC (H.264), 1732kbps
Audio: 187kbps
File size: 389.9 MB
Detention Part Two: DP The Principal Way-Interview - GirlsTryAnal
Release Year: 2015
Studio: GirlsTryAnal
Cast: Samantha Rone, Dana DeArmond, Dana Vespoli
Genres: Blonde, Brunette, Masturbation, Anal, Natural Tits, Milf, Tattoos, Toys, Lesbian, Interview
Video language: English
I see Samantha with a huge ruler, ready to punish me for being a bad girl, asking me if I want her to lick my ass. Where will my mind wander you ask? Watch today and find out!
Format: mp4
Duration: 5:24
Video: 960x544, AVC (H.264), 1696kbps
Audio: 187kbps
File size: 74.8 MB
Detention Part One: French Profanity - GirlsTryAnal
Studio: GirlsTryAnal
Cast: Samantha Rone, Dana Vespoli
Genres: Toys, Blonde, Big Tits, Girl on Girl, Anal, Natural Tits, Small Tits, Anal Fingering, Fingering, College, MILF Mature, First Time Anal, Older Younger, Pussy Licking
Video language: English
Apparently I´ve been a bad girl in school and it landed me in detention with Ms Dana Vespoli. So what If I pointed out the obvious! I mean, French class is not only boring, but meaningless, I mean, it´s not as if I´m going to go to France and tell someone I know how to say what an apple is...I mean give me a break! So, because I opened up my big mouth, I´m here, being punished after class. Well, on the upside, our principal Ms DeArmond has great taste in woman; she must´ve fucked the hell out of her to land this job. I can´t help my imagination running wild, dreaming of Dana DeArmond and Madame Dana Vespoli semi naked licking each other´s faces, but my day dreaming only makes me get into more trouble with Ms Vespoli, ordering me to sit down and finish my homework. Looking at the time go by doesn´t help either, the ticking of the dial seems too surreal. Music and clouds of smoke embrace my thoughts, clouding what I cannot perceive as reality or hallucination. I see Dana with a huge ruler, ready to punish me for being a bad girl, asking me if I want her to lick my ass. Where will my mind wander you ask? Watch today and find out!
Format: mp4
Duration: 35:56
Video: 960x544, AVC (H.264), 1738kbps
Audio: 187kbps
File size: 509.0 MB
Girl
I find it odd how much I end up in detention. I mean, I turn in all of my assignments on time, don't get into fights, use my manners, etc. But, today, I am here again! Wait a second, I am the only one in detention today and there are no chairs here. I take a seat on the top of the desk and wait for the proctor to arrive. When, principal Johnny arrives with rope, I know I am in deep trouble this time. He leads me over to the loft floor above the second level and has me sit in the corner. Wearing my school uniform, thigh high socks and red saddle shoes, I take a seat in my assigned spot. The principal proceeds to tie me in a secure ball tie with rope and attaches my legs to the nearby railing. Then, he places a thick over the mouth cloth gag on my face and starts a timer for one hour, the length of my detention sentence. I struggle around back and forth and mmmphhh and moan into my gag until he finally lets me go at the one hour mark. Hmmmm...detention has gotten easier. I guess it is not so bad having to spend so much time here.
Format: mp4
Duration: 10:56
Video: 1280x720, AVC (H.264), 5840kbps
Audio: 153kbps
File size: 480.0 MB
PunishedBrats - Popping Gum In Detention
Kitty was made to report to detention for stealing candy from Miss Bianca's office. Upon her arrival, she attempted to use her cuteness and get out of this punishment. She noted that she had already been spanked, but she found Miss Bianca unmoved. Being the brat she is, Kitty could not help herself and while sitting in detention started popping gum. She soon found herself bent over the desk for more punishment. She was given thirty stokes with the meter stick. Ten over her skirt, ten on her panties, and then ten on her bare bottom. The tearful girl was shocked when she learned that this was but part of her punishment.
Format: mp4
Duration: 7:57
Video: 1920x1080, AVC (H.264), 24951kbps
Audio: 148kbps
File size: 1.4 GB
Spencer Scott - The Principal's Terms
Release Year: 2024
Cast: Spencer Scott
Video language: English
Spencer visits her ’s principal after an urgent call. It seems that Spencer’s has been secretly stealing money from the PTA, an expulsion-worthy offense, something the proud just can’t allow. Principal Rebel was about to spend some solo quality time with a nice porn vid, but he had to call it off because of this meeting. A flexible man, he is willing to look away from what happened if Spencer enacts some of the stuff the principal was hoping to see in his porn. Making her fall to her knees, Mr. Rebel tells her to suck his cock and praise it. Bending the hot milf on his desk, the principal fucks Spencer’s pussy passionately, making the blonde moan loudly. As she rides her ’s principal’s dick on the guy’s chair, Spencer is to call her boy and tell him that everything will be ok.
Format: mp4
Duration: 30:27
Video: 1920x1080, AVC (H.264), 2075kbps
Audio: 125kbps
File size: 492.6 MB
Penelope Woods, Britt Blair, Kallie Taylor - Good Girls Gone Wild
Release Year: 2023
Cast: Penelope Woods, Britt Blair, Kallie Taylor
Video language: English
Britt, Kallie, and Penelope have always been A-students at school. However, senior year is here, and they want to experiment before going to college because they don’t want to be prudes. Their goody-goody image suddenly changes when the girls post sexy photos of them showing their butts inside the classroom on the first day of school. Mr. Mason, the school’s principal, gives them detention for it and decides to have a serious talk with them about their sudden change. The girls love Mr. Mason, as he used to be their favorite teacher last year, so they confess their desire to experiment before going to college. Trying to save them from bad guys and failing senior year, the principal decides to help his favorite students experiment sexually so they can get it out of their systems and go back to being the sweet school girls they were.
Format: mp4
Duration: 53:42
Video: 1920x1080, AVC (H.264), 3532kbps
Audio: 125kbps
File size: 1.4 GB
Penelope Woods, Britt Blair, Kallie Taylor - Good Girls Gone Wild (2023)
Release Year: 2023
Cast: Penelope Woods, Britt Blair, Kallie Taylor
Genres: org
Video language: English
Britt, Kallie, and Penelope have always been A-students at school. However, senior year is here, and they want to experiment before going to college because they don’t want to be prudes. Their goody-goody image suddenly changes when the girls post sexy photos of them showing their butts inside the classroom on the first day of school. Mr. Mason, the school’s principal, gives them detention for it and decides to have a serious talk with them about their sudden change. The girls love Mr. Mason, as he used to be their favorite teacher last year, so they confess their desire to experiment before going to college. Trying to save them from bad guys and failing senior year, the principal decides to help his favorite students experiment sexually so they can get it out of their systems and go back to being the sweet school girls they were.
Format: mp4
Duration: 53:42
Video: 1920x1080, AVC (H.264), 3532kbps
Audio: 125kbps
File size: 1.4 GB
Detention
Mina has been a bad girl in school, she continually plays games and ties herself up in class! The teacher had enough so she had to spend some time in detention writing lines, gagged. It seems her naughtiness follows her around as she finds herself bound very tightly sitting at her desk. Who know maybe detention is what she wanted all along, Is it a punishment if you enjoy it?
Format: mp4
Duration: 16:54
Video: 1920x1080, AVC (H.264), 6574kbps
Audio: 124kbps
File size: 830.2 MB
Skyler Storm - There is a Storm Brewing (2023)
Release Year: 2023
Cast: Skyler Storm
Genres: HD Video, All Sex
Video language: English
Skyler is a known troublemaker - fucking dudes and sending nudes in school chats. Naturally, she lands herself in detention often. But Joshua is not supposed to be in detention. He is a goody-two-shoes who was in the wrong place at the wrong time. Mr. Jaye leads the detention and doesn’t want to hear a peep out of either of them. Skyler, causing trouble once again, shows Josh that she isn’t wearing any panties - he can see her shaved pussy right up her skirt! Skyler knows Josh is hiding a big cock in his pants, and she wants a piece. When they have a chance to go at it, the unlikely nerd scores with the smoking-hot babe. Skyler is surprised Josh is as good at fucking as he is, and Josh can’t believe he’s getting laid right there in detention.
Format: mp4
Duration: 38:46
Video: 1920x1080, AVC (H.264), 2648kbps
Audio: 125kbps
File size: 789.7 MB
Skyler Storm - There is a Storm Brewing
Release Year: 2023
Cast: Skyler Storm
Video language: English
Skyler is a known troublemaker - fucking dudes and sending nudes in school chats. Naturally, she lands herself in detention often. But Joshua is not supposed to be in detention. He is a goody-two-shoes who was in the wrong place at the wrong time. Mr. Jaye leads the detention and doesn’t want to hear a peep out of either of them. Skyler, causing trouble once again, shows Josh that she isn’t wearing any panties - he can see her shaved pussy right up her skirt! Skyler knows Josh is hiding a big cock in his pants, and she wants a piece. When they have a chance to go at it, the unlikely nerd scores with the smoking-hot babe. Skyler is surprised Josh is as good at fucking as he is, and Josh can’t believe he’s getting laid right there in detention.
Format: mp4
Duration: 38:46
Video: 1920x1080, AVC (H.264), 2648kbps
Audio: 125kbps
File size: 789.7 MB
Kendra Heart - You Shouldn't Be A Principal FullHD 1080p
Release Year: 2022
Cast: Kendra Heart
Video language: English
Schoolmom Kendra gets called into her son’s Principal office for an urgent meeting. Principal Green tells Kendra that her son has been airdropping inappropriate pictures into other students’ phones which is considered sexual harrasment and warrants expulsion. Kendra tries offering some money to help fix the problem but what Principal Green really wants is to fuck this pretentious mylf!
Format: mp4
Duration: 35:15
Video: 1920x1080, AVC (H.264), 6067kbps
Audio: 125kbps
File size: 1.6 GB
Kimmy Kimm - Cute Kimmy Makes Detention Worth It!
Release Year: 2023
Cast: Kimmy Kimm
Video language: English
Kimmy Kimm is convinced that having something in her mouth will make detention less boring. She makes this detention worth it with Tyler Cruise's big cock!
Format: mp4
Duration: 27:07
Video: 1920x1080, AVC (H.264), 4694kbps
Audio: 187kbps
File size: 971.0 MB
Sandy Love - A Good Exchange (2023)
Release Year: 2023
Cast: Sandy Love
Genres: HD Video, All Sex
Video language: English
Schoolmom Sandy is called into Principal Green’s office after her is caught stealing test answers and cheating. Principal Green explains that something like that merits an expulsion so Sandy begs him not to do that, and says she’s willing to do anything to prevent her from being expelled. Principal Green then approaches her from behind and starts feeling her up! Sandy understands what she must do now and starts sucking the Principal’s huge cock!
Format: mp4
Duration: 38:44
Video: 1920x1080, AVC (H.264), 6656kbps
Audio: 125kbps
File size: 1.9 GB
Kendra Heart - You Shouldnt Be A Principal (2022)
Release Year: 2022
Cast: Kendra Heart
Genres: Milf, Big Tits
Video language: English
Schoolmom Kendra gets called into her son’s Principal office for an urgent meeting. Principal Green tells Kendra that her son has been airdropping inappropriate pictures into other students’ phones which is considered sexual harrasment and warrants expulsion. Kendra tries offering some money to help fix the problem but what Principal Green really wants is to fuck this pretentious milf!
Format: mp4
Duration: 35:15
Video: 1920x1080, AVC (H.264), 6067kbps
Audio: 125kbps
File size: 1.6 GB
Sandy Love - A Good Exchange FullHD 1080p
Release Year: 2023
Cast: Sandy Love
Video language: English
Schoolmom Sandy is called into Principal Green’s office after her is caught stealing test answers and cheating. Principal Green explains that something like that merits an expulsion so Sandy begs him not to do that, and says she’s willing to do anything to prevent her from being expelled. Principal Green then approaches her from behind and starts feeling her up! Sandy understands what she must do now and starts sucking the Principal’s huge cock!
Format: mp4
Duration: 38:44
Video: 1920x1080, AVC (H.264), 6656kbps
Audio: 125kbps
File size: 1.9 GB
21sextreme - The Principal's Lecture
Release Year: 2012
Studio: 21sextreme
Cast: Nikky Thorne, Melon
Genres: lesbian, bdsm, femdom, fetish, teen, black hair, blonde
Video language: English
Principal Nikky Thorne is not really happy with Melon´s behavior. She acts like a slut, dress like a slut, and her makeup and nail job communicates a message which doesn´t belong between the walls of a school. But Principal Thorne has enough of Melon and she invites the girl into her office to teach her a lesson: if you act like a slut, you´ll become one. This time, poor Melon´s become the principal´s slut.
Format: mp4
Duration: 32:40
Video: 960x540, AVC (H.264), 2734kbps
Audio: 153kbps
File size: 692.0 MB
Detention Overload
Video language: English
A troublemaking student, Lawson Jones, keeps landing himself in detention but clearly isn't bothered by it. His many teachers (Lolly Dames, Rachael Cavalli, Sarah Taylor, Cassie Del Isla, and London River) squabble over whose detention he should serve first. Things get a bit heated until the teachers realize that they are FIGHTING each other when they should be WORKING together to punish Lawson! That's when the teachers band together to try and work out Lawson's pent-up troublemaking energy in a steamy reverse gangbang.
Format: mp4
Duration: 59:12
Video: 1920x1080, AVC (H.264), 8711kbps
Audio: 187kbps
File size: 3.8 GB
Nikky Thorne, Melon - The Principal's Lecture
Release Year: 2012
Studio: 21sextreme
Cast: Nikky Thorne, Melon
Genres: lesbian, bdsm, femdom, fetish, teen, black hair, blonde
Video language: English
Principal Nikky Thorne is not really happy with Melon´s behavior. She acts like a slut, dress like a slut, and her makeup and nail job communicates a message which doesn´t belong between the walls of a school. But Principal Thorne has enough of Melon and she invites the girl into her office to teach her a lesson: if you act like a slut, you´ll become one. This time, poor Melon´s become the principal´s slut.
Format: mp4
Duration: 32:40
Video: 960x540, AVC (H.264), 2734kbps
Audio: 153kbps
File size: 692.0 MB
Lose Your Balls
Cast: Brittany Andrews, Whitney Wright, Tony Orland
Genres: Femdom, Hardcore, Handjob, Pantyhose, CBT, Cum Eating, Cumshot, Ass Licking, Rimming, Pussy Licking, Masturbatio
Video language: English
Whitney Wright is a very hot and extremely slutty student in Tony Orlando’s class. He’s trying to play it cool while she fingers her own pussy while sitting on her desk in his classroom. The Principal (Britany Andrews) storms into his class and confronts him about fucking his students. He swears he would never… Then Principal Andrews tells him it’s ok, he should fuck his hot student. Whitney spreads her legs wide on her teacher’s desk while Principal Andrews shoves Tony’s face in her young pussy. Whitney asks, “Principal Andrews, is this like the last teacher who you told me to fuck and then we cut his balls off after…?” Right then Whitney clamps her thighs around her teacher’s neck, trapping his mouth on her pussy. Principal Andrews explains that he will be fucking his student, but after he cums they will be destroying his balls for good… Whitney begs for his cock, and smiles when he quickly wants to cum. She knows her young pussy is too much for him to handle. Every time he gets close to cumming, Principal Andrews pulls him away and the two ladies torture his balls with hard squeezes and bites. Eventually they let him cum all over her pussy. They make him lick it all up while they discuss a few terrible ways to castrate him in the shop class with power tools.
Format: mp4
Duration: 19:53
Video: 1920x1080, AVC (H.264), 7789kbps
Audio: 221kbps
File size: 1.1 GB
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