Lennox Fetish Videos & Clips
I'm here to put you in your place. I love the feeling of my stilettos pressing into you during trampling sessions. Whether I'm using my big butts for face sitting or ass smothering, I make sure you know who is in control.
I specialize in sissy training and feminization to turn you into one of my sissy sluts. You can start by giving me some boot worship or shoe & boot worship while I use verbal humiliation to break you down.
If you have a tiny dick, I'll enjoy some small penis humiliation before I decide if you're fit for cuckolding. I might put you on all fours for some ponyplay or make you suffer through some jumping.
I enjoy using a strap-on to dominate, and I'll leave you wanting more. I'm all about boot domination and the look of pantyhose/stockings while you're performing cock worship for me. Come see how I handle my slaves.
Lennox Fetish Videos & Clips
I'm here to put you in your place. I love the feeling of my stilettos pressing into you during trampling sessions. Whether I'm using my big butts for face sitting or ass smothering, I make sure you know who is in control.
I specialize in sissy training and feminization to turn you into one of my sissy sluts. You can start by giving me some boot worship or shoe & boot worship while I use verbal humiliation to break you down.
If you have a tiny dick, I'll enjoy some small penis humiliation before I decide if you're fit for cuckolding. I might put you on all fours for some ponyplay or make you suffer through some jumping.
I enjoy using a strap-on to dominate, and I'll leave you wanting more. I'm all about boot domination and the look of pantyhose/stockings while you're performing cock worship for me. Come see how I handle my slaves.
Lennox XXX Latest Videos
Hormones, Waxed, Chastity, Makeup... and her first Cock
10/16/26 5:00 PM•5 min•433 MB•mp4•1080p
Hormones, Waxed, Chastity, Makeup... and her first Cock
10/16/26 5:00 PM•5 min•433 MB•mp4•1080pPrice$5.99 USDStoreClub Stiletto FemDomCategorySissy SlutsRelated CategoriesCock Worship,Female Domination,Sissy Training,Transformation Fantasies,Transformation FetishPerformersMistress Kandy, LennoxDescriptionKandy was in the garden inspecting the efforts of her young new gardener. Typical male, he tries to come on to her not realizing who he is dealing with. Now, as this scene opens we find the young fellow sitting on a chair a victim to Kandy’s magical powers as she has altered his outlook on life so he now sees himself as a sissy that longs to suck cock, no longer a manly man trying to get into a girls panties. Kandy has invited her friend Winter over to use her makeup skills to transform him into a pretty girl.
In this clip you see the full transformation of the sissy. A fully waxed body, locked in chastity, small breast development, and then makeup applied, wig added and topped off by a pretty sissy dress until we eventually see the sissy on her knees taking a studs cock into her mouth. Along the way Kandy and Winter talk about plans for the sissy, how many cocks she will be expected to service daily, and so on. This sissy can't imagine days in the outdoors planting flowers and trimming trees anymore, all she wants is cocks. Cocks, cocks and more cocks and the thought of the weekend party, and a lineup of studs, has her dripping in anticipation.
Slutty Sissy Samantha Spit-Roast
2/24/26 11:56 PM•6 min•571 MB•mp4•1080p
Slutty Sissy Samantha Spit-Roast
2/24/26 11:56 PM•6 min•571 MB•mp4•1080pPrice$6.99 USDStoreClub Stiletto FemDomCategorySissy SlutsRelated CategoriesCock Worship,Cum In Mouth,Feminization,Sissy Training,Strap-OnPerformersViolet Jackson, LennoxDescriptionLady Lennox has given sissy samantha a makeover as seen in 'Sissy Samantha transformed and turned into Cock Hungry Slut' and in this scene after she makes Samantha suck her dildo for a while, and a pep talk, she hands her over to Goddess Violet and her male stud friend Lucifer for some old fashioned spit roasting. The weekend party is just around the corner and they want to make sure this slut can handle cocks and strap-ons alike, one after another and for hours on end. Up to twelve hours, Violet tells her.
Violet fills the sluts cunt with a giant black cock while Lucifer feeds her his hard cock. Violet says if Samantha takes 100 cocks Saturday she might let her cum too. Maybe! "All that protein, you'll be so healthy" she says. The action and the verbals make for a super hot scene and as a climax Lucifer fills the sissies mouth with a hot steamy load of cum that the sissy lets run onto his cock before sucking and licking it all up. Every drop, of course. This action has Violet aroused so she asks Lucifer if he wants to go upstairs and fuck her. He has unlimited stamina and is only to happy to oblige. Samantha is left there in case they want to fuck her again or maybe some of the other girls around the house would like to use her.
Big Luscious Ass, Scrawny Pony
1/22/26 10:30 PM•7 min•967 MB•mp4•1080p
Big Luscious Ass, Scrawny Pony
1/22/26 10:30 PM•7 min•967 MB•mp4•1080pPrice$6.99 USDStoreRiding WomenCategoryPonyplayRelated CategoriesFemale Domination,Femdom,Ponyboys,Shoulder Carry,Shoulder RidingDescriptionLady Lennox has been out riding her pony boy and although he is already looking a bit weary, she is not done with him yet. She directs him into the woods and even though it’s late autumn it’s warm so she removes her jacket and throws it at the camera man to carry. All men are below her and she expects they will all bow at her feet or she has no use for them. She runs her hands over her big luscious ass and asks the pony how it feels. “He’ll carry me all day just in the hope I let him kiss each butt cheek once” she proclaims. She tells him he’s her ass. “You’re my ass, carrying my ass.”
As they walk through the forest they eventually come to the secret park in the forest. She has the pony go to a bench and do some squats with her still on his shoulders. She compliments him for doing a good job then steps up on the bench and tells him to get down on all fours. She then jumps onto his back for some all fours riding. He carries her to another bench and again she gets on his back to be carried again on his shoulders, this time all the way home.
Sissy Samantha transformed and turned into Cock Hungry Slut
12/27/25 3:41 AM•11 min•904 MB•mp4•1080p
Sissy Samantha transformed and turned into Cock Hungry Slut
12/27/25 3:41 AM•11 min•904 MB•mp4•1080pPrice$12.99 USDStoreClub Stiletto FemDomCategorySissy SlutsRelated CategoriesCock Worship,Cumshots,Gender Transformation,Sissy Training,Transformation FantasiesPerformersViolet Jackson, LennoxDescriptionGoddess Violet has been disgusted with her slave Samantha who was once a dutiful sissy and cock sucker but who lately has really slid backwards. At times like this Violet knows there is only one way to correct things and that's with the 'magic' touch of Lady Lennox. Violet brings her sissy to her and says she has a party that night and her slut has to be anxious to suck as many cocks as she can. She leaves the sissy with her and Lennox asks what the problem is. "I don't like cock" sissy Samantha replies. Lennox reaches into a little pouch on her skirt for her sissy powder and as she sprinkles it the magic happens. "So you don't like cock?" she asks. The sissy, a few octaves higher, enthusiastically says "I love cocks."
Lennox then snaps her fingers and suddenly Samantha is naked with big tits and a pussy, another snap of the fingers and she is now suddenly in a cute little sissy dress. Next comes the makeover and Lennox applies foundation, contour, eyeliner and eye shadow, lipstick, a complete makeover until she looks stunning. She knows all the men and women will want to fuck her later. Lennox is so impressed she even says she might let Samantha fluff her boyfriend later and lick her pussy after to eat up all the cum. Now she returns her to Violet and as it turns out a stud has arrived early. The ladies guide Samantha to suck the studs cock, lick his balls and touch him until he blows a huge load of cum into her mouth. Samantha is ordered to open her mouth and show the cum and then is told to swallow. Samantha loves the taste and now can't wait for all the other guests to arrive. It's a sissy dream cum true.
Lennox's Trampled Toilet slave
10/2/25 9:05 PM•7 min•460 MB•mp4•1080pPrice$7.99 USDStoreClub Stiletto FemDomCategoryTramplingRelated CategoriesBig Butts,Fishnets,Stilettos,Toilet SlaveryPerformersLennoxDescriptionLady Lennox is doing her business on the toilet while a slave lays on the floor enjoying the sound and the odor. He’ll get to lick her clean but will also suffer for the honor. “They say it’s good to have your feet up when using the toilet” she says, so she rests her stiletto’s on her slaves head. She makes him lick her soles while she does her business. Once finished she proceeds to step on the slaves chest. She then realizes she needs to wipe so gets off the slave and sits on his face. The slave gets his tongue in her ass and her crack and licks lustfully.
“I hate using toilet paper, I’d much rather use a slave” Lennox says. Now it’s time to resume trampling because that sort of gift comes at a cost of course. She steps full weight on his chest and stomach and says she loves leaving marks so everyone knows he is her property. The slave moans and groans as she steps on him. She brings one sole up to his mouth to lick as his chest gets all her weight on one heel. Lennox’s ass looks amazing in this scene and the slave is happy to suffer for the view. The camera zooms in to show the deep indents on the slave flesh. Satisfied she decides to reward him by trampling him in only her fishnet stocking covered feet. “I know he loves our bathroom time” she says.
Small dick husband Becomes Her Cuckold Sissy Cock Sucker
5/15/25 1:29 AM•23 min•2330 MB•mp4•1080pClick for gif
Small dick husband Becomes Her Cuckold Sissy Cock Sucker
5/15/25 1:29 AM•23 min•2330 MB•mp4•1080pPrice$16.99 USDStoreClub Stiletto FemDomCategorySissy SlutsRelated CategoriesCock Worship,Cuckolding,Feminization,Sissy TrainingPerformersMistress Mercy Rage, LennoxDescriptionMercy is sitting on the couch laughing while her husband has his head in his lap crying his eyes out as she tells him that she just can't tolerate his tiny dicklet any longer and she has been cheating on him. One of her lovers is his boss which makes him cry even more. "I know this is hard for both of us but I'm filing for divorce" she tells him. Mercy says "I don't know if this will make you feel better but your boss has a really big cock." He cries harder and begs her not to leave and says he'll do anything if she stays. "Anything?" she asks!!! The scene rolls over and while Mercy is playing with her studs big cock and talking about going up to the bedroom she mentions to him that she has sent her husband to her friend Lennox a world renowned makeup artist to continue his transformation to being her sissy cuckold. "I'll be able to lay on the bed with my legs spread waiting for your cock and laugh while he sucks you to get you ready to fuck my tight little pussy" Mercy says with a twinkle in her eye.
Now we see Lennox, who is a cruel bitch in her own right, applying makeup to hubby, who is now called samantha, and getting him, or should we say her, looking very cute and sexy. Lennon mentions that Mercy has said she has hubby watching sissy mesmerization clips non-stop and he admits that the thought of fluffing her boyfriends and cleaning up repulsed him at first but lately all he can think about is hard cocks, taking them up the ass, sucking them and swallowing gallons of cum. Lennox pulls out a dildo and says she wants to see samantha practice sucking it. There is some good advice here for sissy wannabes as Lennox shows samantha how to service a cock. It's not all about sticking the cock in the mouth, it's the use of the tongue and hands, as well as the mouth, that will make the man feel bliss and be super horny to fuck his wife. Pay attention and you might get some ideas for makeup as well as you see Lennox working on the sluts eyes and face. Lennox is happy to offer makeup services to any sissy wannabee in Vancouver, btw!
Lennox is pleased that her friend can now have as many sexual adventures as she wants while having a sissy around to not only prepare and clean up after her lovers but to do all the domestic chores as well. It really has become a story book marriage and who knows Lennox might even borrow samantha from time to time as she always has many hung lovers that are always horny and looking for a whiling mouth or ass. Once the makeup is complete, Lennox presents 'sissy samantha' to Mercy and they talk about how obsessed she has become with cock. Samantha smiles, now eagerly looking forward to spending hours every day sucking cocks. Next Mercy brings samantha in to play with one of her studs. She compares her lovers cock to samantha's and says she is planning to get her breast implants and increase her hormone intake to insure she is as feminine as possible. Watch as samantha sucks cock then takes Mercy's strap-on up her boygina and as well as her boyfriends cock and also how they spit roast her. THE BOYFRIEND CUMS IN SAMANTHAS ASS THEN GOES ASS to MOUTH. As a GRAND FINALE the boyfriend strokes his cock until he unloads his balls, for a second time, all over samanthas face and into her mouth. Lennox and Mercy give some real good tips in this clip for any sissy to insure there is no one better when it comes to oral servitude, and you'll love how a bored husband is transformed into a cum hungry sissy slut and with your imagination it could very well be you.
- 5/27/20 7:26 PM•7 min•495 MB•mp4•1080p

You can kiss This Bootie
5/27/20 7:26 PM•7 min•495 MB•mp4•1080pPrice$6.99 USDStoreClub Stiletto FemDomCategoryTramplingRelated CategoriesBoot Fetish,Jumping,Shoe & Boot WorshipPerformersLennoxDescriptionLovely Lady Lennox comes into the room and finds her slave right where she left him. This is a unique trample scene with Lennox having a chair on the slaves legs to use as a platform to jump off of. When she steps on the chair the leg support pieces of the chair seriously dig into the slaves legs adding even more pain and discomfort. Lennox is wearing her rainbow boots. “I wore them because I was at the gay club” she tells her slave and then says she couldn’t believe how much cum she was stepping in. She makes the slave lick the soles of the boots. She then gets up and stands full weight on the slaves face. You get a great upwards view of the Lennoxs ass so you get a sense of what the slave is seeing.
When she gets off she steps up on the chair and jumps on it a few times before jumping down onto his stomach. She stomps him hard with her boots and then squats down so her ass is inches from his face. The slave asks if he can kiss her booty and she laughs and says “You can kiss this bootie first” as she sticks the toe of a boot into his mouth. Again she squats down and brings her ass inches from his face but as he reaches to kiss it she hops back up on his stomach and this time uses her boots to kick him in the balls. She tells the slave she is tired and sits on the chair to relax, loving how the chair crushes his legs. She lays back and relaxes, no booty for him, only boots.
- 1/21/20 10:04 PM•8 min•519 MB•mp4•1080p

Where's Dirty?
1/21/20 10:04 PM•8 min•519 MB•mp4•1080pDescriptionLady Lennox calls her slave over after having had him spend half the day kneeling in the corner. She tells him her boots are dirty and she wants them kissed, worshiped and licked clean. He lays on his back and she rubs the soles over his tongue delighting in the fact she knows they are very dirty from her night out at the gay club. Not wanting him to get lazy she tells him to sit up so he can better attend to every inch of both boots. “You’re a dirty slave and dirty slaves like dirty things” she tells him. She then says she wants to see the entire boot wet with his saliva. The slave eagerly licks away as if kissing his first girlfriend.
Lennox tells him tomorrow at her party he will be licking everyone’s boots. “And I’m not just talking about the women” she adds. She tells him he’s just a dirty boot licker. “Everyone will be asking, where’s dirty” she tells him. She asks him if he loves being her slave even though she keeps him naked and in her cold dungeon every night. “I love being your slave he replies. “I need to keep you cool for your hot Mistress” she tells him, adding “suffering is part of the job after all.” Lennox has an amazing ass and she knows it as much as anything keeps the slave motivated so she shifts on the couch so her ass is hanging over the edge and allows him to kiss her cheeks while she thinks about the fun she will have tomorrow night at the party.
- 12/25/19 3:05 AM•7 min•455 MB•mp4•1080p

Cruel Heel Trampling
12/25/19 3:05 AM•7 min•455 MB•mp4•1080pPrice$5.99 USDStoreClub Stiletto FemDomCategoryTramplingRelated CategoriesBoot Domination,Face Sitting,JumpingPerformersLennoxDescriptionThis scene opens with Lady Lennox running across the room and leaping onto her slave with her boots. This slave loves Lennox and will stop at nothing to please her. She knows it and does some severe trampling and jumping on this slaves chest and stomach. He urges her to hurt him more and she doesn’t disappoint. She holds on to the overhead bar and pulls herself feet up from the ground before pounding down on his body.
She squats her ass over his face and then sits on it. Her ass looks amazing. She runs her hands over the marks she has left on his body and tells him they please her but they are just getting started. Now she starts jumping on him but makes sure she lands only on her heels until finally she breaks him and he starts to beg for mercy. “I’ll give you a little reward” she says as she puckers her lips above his face. “A kiss?” he asks. As if! She drops a nice big ball of spit from her mouth into his and says “It’s better than a kiss.” She gets up and leaves the broken slave there longing for even more.

I don't want you Thinking, just Doing
9/9/19 10:10 PM•6 min•440 MB•mp4•1080pPrice$5.99 USDStoreClub Stiletto FemDomCategoryFace SittingRelated CategoriesAss Smothering,Cuckolding,Feminization,Verbal HumiliationPerformersLennoxDescriptionLady Lennox has been sitting on her hubby slaves face a lot lately and it really seems to have dummied him down even further. She slaps him gently across his face and tells him she is pleased with his improved disposition. She can’t take things for granted so tells him it’s time for even more time under her ass. “The dumber you are the more money you will make me” she says, as she is slowly starting his transformation into a tranny bimbo cocksucker as seen in the clip ‘ I'm Fucking Your Best Friend But You Can Be Our Sissy Cuckold And Whore ’. Once the hormones kick in ‘goldy’ will develop finer facial features and breasts and then with the right makeup will be getting fucked a lot and making money for Lennox and her boyfriend Francesco who just happens to be goldy’s boss. She kicks his little ‘clitty’ and tells him it will never feel a woman again and it is no good to anyone.
Now she sits down on his head in forward position and with a nice straight back makes sure he is feeling all her weight on his face. The fishnet stockings are sure to make an impression on him too. As she lingers on her head she says she will have to tell her boyfriend about this later. With a bit of luck he’ll be going to work with red lines across his face that look like someone sat on his face wearing fishnets, lol. Lennox gets up long enough for you to get some nice views of her voluptuous ass. She then sits on him in forward position and lifts her legs off the ground so he gets here full 150 pounds. The camera swings around to give you a great view upwards of her ass and body. She just loves seeing his legs kick about. While he struggles for air she tells him that everyone is laughing at him at the office as her boyfriend tells everyone stories about what happens in the house between the three of them. “I wouldn’t be surprised if Francesco starts to face sit you at work too” she says with a laugh. How humiliating! After a breath Lennox sits on him again, this time swinging her legs forward off the ground. When she gets up goldy moans and cries in pain. She tells him to take a breath and as she sits down again she tells him “The worst is still to come.”

Lennox's Cruel Stilettos
8/31/19 9:45 PM•5 min•350 MB•mp4•1080pPrice$5.99 USDStoreClub Stiletto FemDomCategoryTramplingRelated CategoriesStilettosKeywordsStilettos,Trampling,Lady LennoxPerformersLennoxDescriptionLady Lennox admires the marks on her slave’s torso as this scene opens. She steps back on him and then squats, to give him the full impact of her body. She places one stiletto on his head and lifts her other foot into the air. Lennox is a full-figured woman and the slave is subjected to a lot of weight, especially when she stands on one foot.
She steps around on his body and admires the large impressions she leaves on his flesh. She says it’s so much fun to see him suffer like this. Finally, she steps on his neck, then looks directly at you and blows you a kiss.

Your Friend Gets My Pussy, You Get My Feet
7/19/19 2:04 AM•6 min•392 MB•mp4•1080pPrice$5.99 USDStoreClub Stiletto FemDomCategoryCuckoldingRelated CategoriesFoot Worship,Small Penis Humiliation,Stilettos,Verbal HumiliationPerformersLennoxDescriptionLady Lennox has transformed hubby into her pathetic cuck. The poor wimp kneels outside the bedroom, where he hears her getting ravaged by his ex-best friend turned boss, who he works for as a used car salesman. As Lennox appears from the room, she sighs with pleasure and asks, “Did you hear me getting fucked by Francesco?” Hubby’s face turns crimson red with humiliation, and he replies, “Yes, Dear.” To really arouse her new boyfriend, Lennox has had her stilettos on all day, and tells hubby she needs a little foot worship from him to help ease the pain she feels in her feet. She makes him bend down on all fours to kiss her shoes, then suggests that he lick them as well, because she wants them nice and shiny since Francesco will be taking her out for dinner later.
After he has licked for a while, she tells him to suck her heel and rams it into his mouth. As he sucks, she reminds him that his future is full feminization and a lot of sucking, while she turns him into her femmy slut. She orders him to remove her shoes and says, “My feet need a good rubbing, just like Francesco’s cock rubs the inside of my pussy.” Lennox obviously never fucks hubby anymore, and she asks if Francesco ever tells him about their lovemaking at work. The cuck is further humiliated when Lennox says that she and her boyfriend are considering buying hubby a blow-up doll, and that they want to see him make love to ‘her’ when the two of them fuck. She humiliates him further by saying the blow-up doll won’t necessarily be female but could be male instead. “Just don’t pop a hole in it or there goes your love life,” she says, and laughingly adds, “It won’t stay inflated just like you don’t stay inflated.” The camera pans down to show you how tiny hubby is. “His future is to be a street whore,” she says. His tiny cock will be nothing more than a clitty, and his ass a big, gaping cunt.

