Office ass-istant Lily Lovecraft punished with dondage & spanking
Release Year: 2015
Cast: Lily Lovecraft
Genres: Rimming, Asslicking, Bondage, Spanking, Oral, BDSM, Domination, Humiliation, Toys
Video language: English
Pervert man is definitely going to have some fun with her. He takes on sub Lily Lovecraft in this erotic BDSM play session.
-After explaining the concept of the safe word, Master dominates the pretty babe! She really likes to spice up sex with a tiny bit o
Format: mp4
Duration: 1:01:02
Video: 1280x720, AVC (H.264), 3401kbps
Audio: 122kbps
File size: 1.5 GB
Lily Lovecraft - Office ass-istant
Release Year: 2015
Studio: Assylum
Cast: Lily Lovecraft
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Foot licking, Gaping, Painal, Rough oral, Spitting, Bondage, Caning, Face slapping, Pain, Punishment, Spanking, Amateur, Blond, Two guys
Video language: English
Lily is a real submissive anal pain slut. So we gave it to her extra rough. Very hard anal, deep ass to mouth with long anal beads, a harsh caning and ass beating, etc. Then Dr. Mercies turned her into his office assistant and made her take notes in a bondage contraption with a pen up her ass. She did a lousy job, so he punished her by sending in Orderly Sinn.
Format: mp4
Duration: 1:01:02
Video: 1280x720, AVC (H.264), 3401kbps
Audio: 122kbps
File size: 1.5 GB
Assylum - Office ass-istant
Release Year: 2015
Studio: Assylum
Cast: Patient Lily Lovecraft
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Foot licking, Gaping, Painal, Rough oral, Spitting, Bondage, Caning, Face slapping, Pain, Punishment, Spanking, Amateur, Blond, Two guys
Video language: English
Lily is a real submissive anal pain slut. So we gave it to her extra rough. Very hard anal, deep ass to mouth with long anal beads, a harsh caning and ass beating, etc. Then Dr. Mercies turned her into his office assistant and made her take notes in a bondage contraption with a pen up her ass. She did a lousy job, so he punished her by sending in Orderly Sinn.
Format: mp4
Duration: 1:01:02
Video: 1280x720, AVC (H.264), 3401kbps
Audio: 122kbps
File size: 1.5 GB
Kinky Blonde Lily Lovecraft Go To The Painal Theater
Release Year: 2016
Cast: Lily Lovecraft
Genres: Bondage, Spanking, Oral, Anal, BDSM, Domination, Humiliation
Video language: English
Lily Lovecraft is a beautiful girl that has starred in several BDSM scenes. Here she's trying our punishments and tortments!
Format: mp4
Duration: 24:15
Video: 1920x1080, AVC (H.264), 6914kbps
Audio: 124kbps
File size: 1.2 GB
Lily Lovecraft - Painal Theater
Release Year: 2016
Studio: Assylum
Cast: Lily Lovecraft
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Gaping, Painal, Spitting, Bondage, Crying, Face slapping, Pain, Spanking, Suspension, Blond, Two guys
Video language: English
Lily earns a theater trip, but her own anal destruction turns out to be the show. Dr. Mercies ties her up and makes her ride Orderly Sinn´s big cock while she watches in the mirror and eats popcorn. Then Sinn powerfucks her gaping asshole while she kneels like a dog and then lies helplessly on her back. She also eats the doctor´s ass and takes a load of his cum while Sinn fucks her. Then Dr. Mercies beats her ass, and he and Sinn walk out, leaving Lily crying in her cell.
Format: mp4
Duration: 24:15
Video: 1280x720, AVC (H.264), 2239kbps
Audio: 124kbps
File size: 421.4 MB
Hot Lily Thot Punished Hard With Slapping & Spanking
Release Year: 2022
Cast: Lily Thot
Genres: BDSM, Ass Licking, Rimming, Blowjob, Cumshot, Facial, Crying, Slapping, Spanking
Video language: English
Alas, we have reached Lily's final session from her recent stay at the Assylum. What this one lacks in creativity it gains in authenticity. You see, Lily did something bad: she slept through one of her previous sessions. So she and Dr. Mercies agreed she needed to be punished. Dr. Mercies punished her PAWG ass very hard with the vicious rubber tawse. He slapped her face. And he used her mouth roughly. You don't see many sessions like this at the Assylum, but Lily is a real-deal submissive masochist, and it was the right session at the right time.
Format: mp4
Duration: 30:43
Video: 1920x1080, AVC (H.264), 5581kbps
Audio: 119kbps
File size: 1.3 GB
Francesca Accepts Her, One of Us
Cast: Lily Lovecraft ,Francesca Le
Genres: Hair Pulling ,Bondage ,Strap On ,Dildo ,Anal Stretching ,Speculum ,Lesbian ,LezDom ,Anal Fisting ,switch
Video language: English
Francesca Le has found a little slut following her freak show from town to town trying to get freaky with the stars of her show. She puts this little slut into bondage and spanks her ass until it’s bright red. She spreads her ass wide with a speculum and then puts her fist in her ass. Since Lily Lovecraft is such a splendid anal whore, Francesca teases Lily with a taste of ass. Lily is gaged with a penis gag and made to fuck Francesca in the ass while she gets smothered by Francesca’s beautiful cheeks. Lily gets a good hard doggie strap on fucking with Hair pulling. To finish the little anal whore off, Francesca turns Lily into part of the freak show. She is now The Human Dick and Francesca fills her with cum and strokes the dick until it oozes cum
Format: mp4
Duration: 54:52
Video: 1280x720, AVC (H.264), 4878kbps
Audio: 122kbps
File size: 2.0 GB
Punished Lily
Release Year: 2024
Genres: BDSM, Bondage, Humilation
Video language: English
Alas, we have reached Lily's final session from her recent stay at the Assylum. What this one lacks in creativity it gains in authenticity. You see, Lily did something bad: she slept through one of her previous sessions. So she and Dr. Mercies agreed she needed to be punished. Dr. Mercies punished her PAWG ass very hard with the vicious rubber tawse. He slapped her face. And he used her mouth roughly. You don't see many sessions like this at the Assylum, but Lily is a real-deal submissive masochist, and it was the right session at the right time.
Format: mp4
Duration: 30:43
Video: 1920x1080, AVC (H.264), 5581kbps
Audio: 119kbps
File size: 1.3 GB
Assylum - Painal Theater
Release Year: 2016
Studio: Assylum
Cast: Lily Lovecraft
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Gaping, Painal, Spitting, Bondage, Crying, Face slapping, Pain, Spanking, Suspension, Blond, Two guys
Video language: English
Lily earns a theater trip, but her own anal destruction turns out to be the show. Dr. Mercies ties her up and makes her ride Orderly Sinn´s big cock while she watches in the mirror and eats popcorn. Then Sinn powerfucks her gaping asshole while she kneels like a dog and then lies helplessly on her back. She also eats the doctor´s ass and takes a load of his cum while Sinn fucks her. Then Dr. Mercies beats her ass, and he and Sinn walk out, leaving Lily crying in her cell.
Format: mp4
Duration: 24:15
Video: 1280x720, AVC (H.264), 2239kbps
Audio: 124kbps
File size: 421.4 MB
SevereSexFilms - The New Maid - Part 1
Cast: Lily Lovecraft, Vixen Valentina, Jimmy Broadway
Ms. Vixen and her maid/secret girlfriend Lily have a plan to get Vixen’s husband Jimmy out of their hair. When he comes home, Lily pretends Vixen isn’t home. Being horny and none too bright, Jimmy hits on the maid and she acquiesces, giving him a seemingly enthusiastic blowjob. Jimmy licks her pussy and fucks her in several positions. But the moment he cums on her pretty tits, Vixen reappears and threatens to take everything via her excellent divorce attorney. Jimmy says the magic words, “I’ll do anything!” And then he’s Vixen’s bitch. She starts by making him lick the cum off Lily’s tits. But that’s only the start. She has a lot of other torments in mind…
Format: mp4
Duration: 20:25
Video: 1920x1080, AVC (H.264), 24831kbps
Audio: 147kbps
File size: 3.6 GB
Golden fund bdsm video Punished Lily
Release Year: 2022
Studio: Assylum
Cast: Lily Thot
Genres: Ass Licking, Rimming, Blowjob, Cumshot, Facial, Crying, Slapping, Spanking
Video language: English
Alas, we have reached Lily's final session from her recent stay at the Assylum. What this one lacks in creativity it gains in authenticity. You see, Lily did something bad: she slept through one of her previous sessions.
Format: mp4
Duration: 30:43
Video: 1920x1080, AVC (H.264), 5581kbps
Audio: 119kbps
File size: 1.3 GB
Lily Lane - Held Accountable
Release Year: 2017
Cast: Lily Lane
Genres: BDSM, Bondage, Torture, Humiliation
Video language: English
Lily Lane is a naughty accountant who is punished for her misdeeds. At INSEX we pay our debts. Lily Lane was hired as our accountant pay our bills. She couldn't even do that correctly. When OT checks the books he finds that several affiliates haven't been paid in a timely manner. It's a good thing Lily is pretty. OT finds a new way for her to be of use. As he strips her of her clothes and dignity she apologizes and pleads for forgiveness. It's not so easy. Now that he's seen whats under her skirt he's not about to let her get away without having a little fun. She needs to be punished for her transgressions and OT is going to enjoy every second of it. Stuck in stocks Lily has her legs spread wide. A bit gag holds her mouth open and the drool flows freely. OT wants to make her face as hideous as her soul. He puts a dental gag in her mouth to open her face up and then wraps her head. She's now just a face hole.
Format: mp4
Duration: 32:58
Video: 1280x720, AVC (H.264), 7296kbps
Audio: 109kbps
File size: 1.7 GB
Office sleeping beauty
Cast: Sinn Sage, Lily Adams
Genres: Lesbian, Petite, Natural tits, College, Brunette, Mature & Milf, Tattoo & Piercing, Bubble Butt, Ass
Lily's the sexy new temp for the insurance office, but juggling the job and her college night classes are leaving her exhausted. Supervisor Sinn Sage catches Lily 'meditating' one too many times while on the job and secretly watches the hot brunette nod off at her desk yet again...she knows it's time to confront the sleeping beauty. Lily confides in Sinn that she is doing night classes while working because she is drowning in debt. Lily throws herself at Sinn's mercy...and Sinn is very understanding. In fact, she won't tell a soul and is impressed with the young woman's dedication. Lily is relieved, hugging Sinn, thanking her profusely. Sinn's attraction to the tight young body can't be ignored when pressed against her...she kisses Lily, igniting the pent-up attraction the two have. Their kissing turns urgent as they explore one another's wet pussies; Sinn draws pulsing orgasms out of Lily. Soon Sinn's cumming from Lily's mouth and eager fingers too!
Format: mp4
Duration: 32:15
Video: 1920x1080, AVC (H.264), 4252kbps
Audio: 187kbps
File size: 1.0 GB
Office Sleeping Beauty - FullHD 1080p
Release Year: 2018
Studio: SweetHeartVideo
Cast: Sinn Sage, Lily Adams
Genres: Lesbian, Petite, Natural tits, College, Brunette, Mature & Milf, Tattoo & Piercing, Bubble Butt, Ass
Video language: English
Lily's the sexy new temp for the insurance office, but juggling the job and her college night classes are leaving her exhausted. Supervisor Sinn Sage catches Lily 'meditating' one too many times while on the job and secretly watches the hot brunette nod off at her desk yet again...she knows it's time to confront the sleeping beauty. Lily confides in Sinn that she is doing night classes while working because she is drowning in debt. Lily throws herself at Sinn's mercy...and Sinn is very understanding. In fact, she won't tell a soul and is impressed with the young woman's dedication. Lily is relieved, hugging Sinn, thanking her profusely. Sinn's attraction to the tight young body can't be ignored when pressed against her...she kisses Lily, igniting the pent-up attraction the two have. Their kissing turns urgent as they explore one another's wet pussies; Sinn draws pulsing orgasms out of Lily. Soon Sinn's cumming from Lily's mouth and eager fingers too!
Format: mp4
Duration: 32:15
Video: 1920x1080, AVC (H.264), 4252kbps
Audio: 187kbps
File size: 1.0 GB
Lily Lane - Naughty Accountant
Genres: BDSM, Bondage, Rope Bondage, Submission, Domination, Torture, Spanking
Video language: English
Lily Lane was hired as our accountant pay our bills. She couldn't even do that correctly. When OT checks the books he finds that several affiliates haven't been paid in a timely manner. It's a good thing Lily is pretty. OT finds a new way for her to be of use.
As he strips her of her clothes and dignity she apologizes and pleads for forgiveness. It's not so easy. Now that he's seen whats under her skirt he's not about to let her get away without having a little fun. She needs to be punished for her transgressions and OT is going to enjoy every second of it.
Stuck in stocks Lily has her legs spread wide. A bit gag holds her mouth open and the drool flows freely. OT wants to make her face as hideous as her soul. He puts a dental gag in her mouth to open her face up and then wraps her head. She's now just a face hole.
Format: mp4
Duration: 32:58
Video: 1280x720, AVC (H.264), 7296kbps
Audio: 109kbps
File size: 1.7 GB
Jack and Jill - LilyKawaii's First Double Team
Release Year: 2021
Studio: Jack and Jill
Genres: Gonzo, Hardcore, Group Sex (FFMM), Petite, All Sex
Lilykawaii said she wanted to come back and visit us and try something new! We decided to set her up with our friend SamShockX for their first show and her first ever double team/spit roast. Lily said she was a bit nervous, but the show went perfectly! Lots of fun clips in the public show of us all spanking eachother, stripping our clothes off, massaging Lily and Lily giving her first double handjob. Show starts with Jill sucking Jack, Lily sucking Sam. Jill helps Lily with Sam, Jill sucks Sam's balls and feeds Sam's dick to Lily. Lily then gives her first ever double blowjob. Next Jill and Lily get fucked side by side riding cowgirl facing away and towards the camera and then in missionary. Sam then fucks Lily in while she sucks Jack's cock. Jack then fucks Lily in side- while Lily sucks Sam. Lily then tries the fuck bench for the first time and gets spit roasted by both guys. Show ends with Sam and Jack cumming all over Lily's perfect boobs and Jill licking off both guys cum. Multiple camera angles not featured in live show are shown in this recording. Jill and Lily give pussy close-ups before we say our goodbye's.
Format: mp4
Duration: 1:49:31
Video: 1920x1080, AVC (H.264), 2803kbps
Audio: 62kbps
File size: 2.3 GB
Busty Babe Lily Lane Restricted & Punished Hard
Release Year: 2018
Cast: Lily Lane
Genres: BDSM, Bondage, Humiliation, Torture, Vibrator
Video language: English
Lily's every bodily function is restricted. Lily is used to sucking dick when she comes to visit Insex. However, OT has a bit of a twisted sense of humor. He shoves several hard inches of cold steel down her throat. She drools and coughs as it triggers her gag reflex. Her tight body flinches and twists as she tries to get off of the rod. OT Lily's ass with more steel. Her back is made to arch pushing her ass out in the most exquisite manner. Her tits are exposed and she's left to create a puddle on the floor. The theme of the day is restriction and Lily is definitely restricted. From the orgasm denial, to breath control, to sight restriction, to the strenuous bondage positions Lily is given no freedom. She is ours to play with. The bondage positions start hard and they only get harder.
Format: mp4
Duration: 40:07
Video: 1280x720, AVC (H.264), 7330kbps
Audio: 106kbps
File size: 2.1 GB
Gyno What You Did Last Summer (2022)
Release Year: 2022
Cast: Kenna James, Kenzie Taylor, Serene Siren, Lily Larimar
Genres: Lesbian
Video language: English
Serene Siren and Kenzie Taylor are accompanying their Lily Larimar for an appointment with their family gynecologist, Kenna James. Kenna begins the checkup with some routine questions and when everything seems to check out, asks Lily what has brought her in today. Lily reveals that she's recently become sexually active, so she thought now would be a good time to do a checkup. Kenna is supportive of this new development in Lily's life and agrees to perform the checkup. But before getting started, she makes sure that Lily is comfortable going through it with her stepmoms in the same room. Lily nods- absolutely, she's totally cool with that.
Kenna begins the checkup by inspecting Lily's mouth, throat, and ears. She then undoes the back of Lily's gown and inspects her breathing. Everything seems normal, so Kenna asks Lily to remove her gown completely for a more thorough examination. Lily strips naked and spreads her legs, giving Kenna a good view of her vagina. Kenna puts on some gloves and moves Lily's panties to one side, sticking one of her fingers inside of her. There are hints that both Kenna and Lily are enjoying this, but they wouldn't dare admit it- especially when Lily's stepmoms are watching from the side of the room.
Speaking of Lily's stepmoms, Kenna notices that both of them seem to know quite a bit about Lily's sex life... Maybe a bit TOO MUCH, actually. Serene and Kenzie try to play it off- Lily tells them everything, so of course, they know some details about what she gets up to. But Kenna can read through the lines and it becomes increasingly clear that Lily is in fact in sexual relation with her stepmoms! But Lily assures Kenna that it's completely consensual... and FUN. Well, Kenna doesn't have any issue with that, as long as she gets to join in! Serene and Kenzie are taken aback for a moment, though become intrigued when Lily seems to be into it. Why not? They have an energetic and playful foursome in Kenna's office, making this one doctor's appointment they'll talk about for all the summers to come.
Format: mp4
Duration: 41:56
Video: 1920x1080, AVC (H.264), 4541kbps
Audio: 187kbps
File size: 1.4 GB
Gorgeous 19 Year Old Punished and Fist Fucked by Sinn Sage
Cast: Lily LaBeau ,Sinn Sage
Genres: mixed ,switch ,shaved ,Dominatrix ,Humiliation ,Strap On ,Leather Gloves ,Pain Slut ,Vaginal Fisting ,Facesitting ,Fingering ,Spanking ,Leather ,Sub
Video language: English
Lily LaBeau; beautiful face, gorgeous long legs, all natural perky tits and she’s dying to get fist fucked by a girl! Sinn Sage is hot as ever and makes Lily earn her attention with heavy punishment and hot girl on girl BDSM. She’s made to worship ass, takes two painful zippers, ass hooked, fisted and fucked in tight bondage with a large strap-on cock.
Format: mp4
Duration: 1:02:21
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 122kbps
File size: 1.4 GB
Lily Starfire, Madison Wilde - Both had huge orgasms (2023)
Release Year: 2023
Cast: Lily Starfire, Madison Wilde
Genres: Lesbian, Interracial
Video language: English
Lily was on a dating app looking for guys to hook up with. She noticed that none of the guys looked hot to her. She started wondering if she even liked guys anymore. So Lily called in her roommate Madison to ask her how would she know if she liked girls. Madison said that’s easy. Let me kiss you and see if you like it. So Madison gave Lily a deep kiss and Lily seemed to like it. Then Madison asked Lily if she could undress her and play with her huge tits to see if she liked that. Lily seems to love how that felt. Madison seeing that Lily was all about it she went down and started licking Lily's pussy. Lily ended up having an orgasm and she asked her to eat her pussy from behind. Then after that Lily wanted to taste Madison's pussy. With Madison guiding Lily on what she liked, Madison had a huge orgasm. Then Madison busted out a vibrator that they both took turns on. Both had huge orgasms and Lily seemed all about girls now.
Format: mp4
Duration: 35:33
Video: 1920x1080, AVC (H.264), 9767kbps
Audio: 95kbps
File size: 2.5 GB
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