Pinky has all kinds of panties in her sissy collection! Some are full figured, vintage "granny panty" styles but there are also some string bikinis mixed in to show her naughty side. Some of the panties are beautifully sheer, leaving nothing to the imagination while others are opaque but made of very sensual, slippery satin.

The more I layer on the pairs of panties, the harder Pinky's sissy clitty gets!

Pinky's other favorite sissy pastime (besides wearing panties) is to have her garters snapped by dominant women. She also loves it when we tickle her little rosebud back door, but secretly finds it humiliating to admit how MUCH she enjoys it.

Under pantied interrogation, Pinky admits that some of the lingerie was STOLEN from women and other crossdressers, so I give her stern spanking!

As punishment for stealing panties, Pinky now has to come shopping for panties with me IN PUBLIC and admit that she is a pretty sissy panty slut to the lingerie saleswomen!

I smother and cover her in ruffled lace girly panties and force Pinky to watch herself being humiliated and emasculated in front of a HUGE mirror.

Enjoy this extreme ruffled sissy panty bondage scene using this long-time crossdresser's collection of ultra-custom fetish panties!!!

This full set of metal restraints has been waiting for the perfect petite person to come along to reclaim it. After a year of searching, I think we have finally found the perfect fit - the tiny, young and flexible Bambi Belle!

Bambi is new to porn, but not to bondage, kink or dirty thoughts. Since they are Denali Winter's personal submissive, we start the scene with some punishment. Using spanking, canes and paddling, we bring out the submissive side of the brat. As sexy as their struggling and moans are, my favorite part is playing tick tack toe with scratch marks on their ass. With Denali as our guide, it is going to be fun to push the limits of how easily and how often Bambi's lily white skin can be marked!

Pain and pleasure make such a good combination that we eventually reward Bambi with the Hitatchi Magic Wand vibrator. Eventually their owner Denali might even give them permission to have an orgasm... but only once they have earned it!!!

I also love this custom "butterfly" strait jacket, made from thick black leather. There is not a bit of wiggle room, his arms are forced to fold into tiny "chicken wings" and he is completely defenseless to protect his nipples, his ass or his balls from my onslaught.

Even though he is a big, strong man the rest of the time, there's nothing he can do to prevent me from having my way with him. I brought some MEAN nipple clamps and a metal ass hook that I tie into place as part of his ordeal.

The more bondage I add, the sluttier he becomes. No amount of bondage seems to scare him badly enough that he goes soft. His cock just keeps getting harder and harder instead of being frightened away by the intensity of our bdsm scene.

I let Modenarr exhaust himself struggling in his bondage predicament while I taunt him and post dozens of humiliating photos all over social media using his cellphone. He is the town slut, with quite a reputation! We both have a big following on twitter, reddit and tumblr plus a few other social media sites that appreciate bondage shenanigans with a sense of humor!

There is nowhere he can go to get away from me. Every direction he turns in exposes another part of his body to my torment. Eventually he is too tired to put up much of a fight so I make a bargain with him: He has five minutes to have an orgasm.

If he does not manage to squirt his submissive load in time, I am going to fuck his ass using the gas mask dildo so he will be forced to breath in the experience for a smelly anal breath play scene from hell!

Which will win? His fear or his lust?

Either way, I am going to have a good time...

How well could you perform under this kind of pressure?

. . .

Standing bondage is especially rigorous and intense - a stress position - don't leave a submissive unattended this way, especially when bound by the neck!

My dear submissive "Footsub" has been bragging to me that he could take bigger toys then anyone else on my website so far.

This shoot is my way of seeing if his ass really can handle all that he bragged about. We enjoy some flirty banter while I tie him up and explore his ass with my hands. I always appreciate his wit and charming smile.

Enjoy some hilarious stories of anal hijinx from a true ass slut while I stuff him to the cheeks with a new strap-on toy we lovingly call "the Dino Dick!"

All of the toys we enjoy in this clip came from our local Mr S Leathers in San Francisco.

If you've ever had your mouth washed out with soap, this will stir up powerful and terrible tasting memories!

Bambi starts out looking adorable and even a little vanilla, but we are going to turn them into a hot, bubbly mess by the end of this scene. Denali and I join forces with Sybil Holiday supervising as we initiate Bambi Belle into the world of Bondageland. Soon, they will be ONE OF US!!!

Be careful with mouth soaping! The bubbles are an easy choking hazard, especially when submissives are in bondage. By the time we are done, there will be a mild chemical burns on their tongue. Bambi won't be enjoying any fancy dinners for at least a week but fortunately mouths heal quickly.

We start with the most mild soap, similar to what you would find in a hotel bathroom. Once Bambi's mouth is numb, then we build up to a floral scented moisturizer bar and finally use the most pungent of them all. You can SMELL how intense this soap is from all the way across the dungeon. With real lye, this is a real punishment. Bambi will be tasting detergent for days!!!

This elaborate bondage scenario comes right out of my favorite vintage femdom magazines! The Scavenger's Daughter is a bondage suspension rig inspired by famous bdsm drawings and a real torture device invented during King Henry VIII of England's reign.

The bondage frame is built to fit this loyal slave's proportions. My slave's black rubber catsuit is also made to measure so that every inch is completely covered in form-fitting latex. The booties are exquisite and even more impressive because each individual toe is encapsulated. There are built-in gloves too, no detail is overlooked in this bespoke creation.

One set of locks at a time, my slave becomes more and more helpless. The first wire goes from the tens unit to an electrified cockring. The second wire is attached to a huge butt plug. The best part about the way he is wired is that all the toys are VOICE ACTIVATED!!!

Whenever I give him orders, the shocks get him where it counts! When he cries out in pain, he triggers the noise sensors even MORE for a vicious feedback loop of cbt and anal stretching. Will this make him pay attention or just distract him? Only time will tell.

Does all this bondage and electricity sound like heaven or hell to you?

- Haiku by YourSissyJoy

WE WON "BEST BONDAGE WEBSITE" AT THE BONDAGE AWARDS!!!

Thank you SO MUCH for all of your votes and support! This is the sexiest trophy I've ever seen!!!

I've captured the hearts and groins of fans all over the world and your votes put is on top despite some very stiff competition. To celebrate our award and also to commemorate Denali Winter winning Best New Site (a category without a physical trophy), I'm hosting a kinky Academy Awards inspired party. We are also going to make sure Denali has a special DIY prize to take home.

We strip Sissy Joy down to their chastity cage and bra with plenty of obligatory groping. Taking pains to secure our submissive extra tightly with cling film, we wrap their torso and arms individually before sticking them down against their body. Since the wrap adheres to itself, they are that much more secure before we add the next layer of bondage. Once we wrap them in bright gold duck tape, the bondage will be inescapable. Pay careful attention to the tops of a submissive's shoulders if you're enjoying mummification at home. Some flexible escape artists can pull their arms right out of the "sleeve" formed between the layers if you don't close up the top of the mummy wrappings.

I love that we cover Sissy Joy's FACE with tape in this scene too. There's something invasive and personal about anything touching your face... especially when there is nothing you can do about it!

Cocooned in head to toe tape, standing bondage becomes extra dangerous. Sissy Joy wobbles as soon as their eyes are covered, adding drama to their predicament. For their own good, we put them inside of the standing cage. With all the doors, we can lock and unlock access to various parts of their body. With some time to stew in the bondage under secret supervision our crossdressing subbie has plenty of time to contemplate what we might do next.

When we finally open the center panel of the cage, Sissy Joy startles and practically falls over with fright. Good thing we have them secured where there is nowhere to go. Exposed and helpless, their erection surges so hard while I try to remove their chastity device that I resort to ice to bring down their dick swelling before I can take it off at all! CBT before the device even gets removed. Something tells me this scene won't be getting any easier for our suffering sissy.

Lots of teasing, tormenting, frustration, edging, denial and heavy bondage in this celebration of our femdom and BDSM flavored awards!

This scene involves retching, gasping, suffering and even tears as ZombiePup struggles to take his punishment. Mistress Sybil spells out the names of all the foods he has eaten to wash those flavors out of his dirty, slutty mouth. We even add some LIQUID soap and make him gargle for good measure. No spitting! Swallow all that soap so it can clean you out INSIDE too.

Zombie is the filthiest submissive we know but, for some reason, he still manages to charm even the most discerning of women. Mistress Sybill Holiday is coming out of retirement for this very special "good old fashioned" mouth soaping scene! She was the queen of San Francisco's femdom bdsm scene (along with Cleo Dubois) for most of the 1980s. This is the first time my viewers get to meet the mysterious "Lady of the House" behind the purple dungeon and her vast toy collection.

There's something wonderful about an older, classy femdom initiating younger submissives. Mistress Sybil Holiday is so experienced and powerful that she doesn't even need to get out of her chair to put Zombie in his place. She exudes confident maturity born from hundreds of scenes through the years and she manages to be both loving and menacing at the same time.

ZombiePup is even more humiliated because we are not alone, Denali and Bambi are also here to witness his punishment! This scene is a cruel preview for Bambi since they are up next - more mouth soaping for all our dirty Bondageland subs!

This scene is a great example of how dominating a submissive does not have to involve physical exertion from the top in order to be devastatingly effective. Instead of aftercare, he just gets face slapping. Think of the slaps as special mistress kisses. She leans in close, "Do you remember when I said I would smile while you cry?"

Instead of finding full body immobilization frightening, this leather slave welcomes the feeling of encasement and compression with a sense of safety. Bondage can be comforting as well as arousing. This slave lives by a motto: "the more bondage, the better!

We take extreme bondage to the next level, starting with a beautiful cobalt blue catsuit, then adding custom fitted leather gloves, booties and a sensory deprivation hood with a special built-in gasmask.

This shoot is a visual feast of color in the usually monochrome world of leather fetishists. There is not a speck of human skin visible on my colorful gimp when I start adding the locking straps.

Layers of leather and straps render my submissive completely helpless on the bondage chair. Soon, it is time to add breath play using the gas mask and a valved breathing bag.

Some of you might find this level of bdsm play terrifying, but others will find it sexy. I invite you to consider this extreme side of human sexuality with an open mind and confront your personal fears around being completely OUT OF CONTROL.

I am certain many people reading this secretly long to surrender complete control to a beautiful, dominant woman.

Would it be easier to accept your fate if I added a vibrator?

Would you be willing to trade your breath for a chance at an orgasm?

Even the most deviant, depraved and fetishistic sexual acts can seem normal when a sexy woman suggests them, especially as you are edging closer and closer to an explosive orgasm!

The closer he gets to cuming, the more I restrict his breathing.
Which will give in first?
His dick or his breath?

Through heavy bondage and female led subjugation, I help him find a sense of belonging inside his physical body. I offer him an escape from the constant, swirling thoughts of his intelligent mind and help him find peacefulness in service, feminization and leather objectification.

Bondage helps him to Be Here Now.

Mistress Vyra is also here at the DomCon femdom convention so we have a golden opportunity for a strap-on gangbang between classes. This time we use layered bondage to conquer our new submissive volunteer. We start with my special institutional strait jacket to keep him "safe" from himself but there is nothing that can keep him safe from the three of us!

Once he is partially incapacitated with canvas, it is time to add layers of palate wrap! We wind the cling film tighter and tighter around his torso. Now there is no wiggle room at all! With teamwork, we quickly turn him into a very secure package.

Hooded and with ducktape over his eyes, he is more and more unstable on his feet. We slap his cock and balls but the CBT just seems to make him harder! Before he falls down, it is time to lay him down on the couch for even MORE bondage.

Now that he is completely helpless, our big black cocks come out to assault his formerly tight little hole.

Can he come while being pounded in the ass by three sadistic women?

Could YOU handle dildos this big?

Behold! Our most daring public outdoor shoot yet!

Monika is a naughty schoolgirl but I am even naughtier in my authentic Japanese sailor suit school uniform.

I tie her down on a park bench at the overlook with two look-outs to make sure no one stumbles upon our scene in progress. When she is secure, I relish in humiliating her, taunting, teasing and tickling until I discover her hard cock beneath the many layers of petticoats and panties.

She has a surprisingly big dick for a sissy so there is NO way it will fit into a chastity device while still engorged. I know a "cure" for erections so I make her cum for me and then STUFF her softening cock into the CB6000 before she can change her mind!

This is your last orgasm, from now on you have to cum like a girl!!!

His balls retreat in fear as we TEAR OFF his polo shirt and brown shorts. He stuck out like a sore thumb among all the fetish wear! Nude and in bondage, now he is ready to properly participate in the festivities.

Mistress LittleStar and I chain him against a chainlink fence, making sure he is completely spread eagle so that he cannot move or fight back but especially could not close his legs!

My fantasy included ball busting, cbt and harsh metal bondage... but the crux of my desires was INCDLUING AS MANY OTHER WOMEN AS POSSIBLE.

For the next 2 hours, I invite dozens of women up to kick him in the balls. Some were nervous, so we offered them a riding crop instead. I lost count of the numner of women that stepped up to take out their aggression on our helpless target. Boots of all kinds, high heels and even some barefoot busting took its toll on his sore balls all afternoon.

Countless women tortured his genitals, on and off camera. We had unknowingly set up right next to the women's area of the fair and there were lots of ladies with scores to settle against mankind for the wrongs they have done to our gender. We stayed nearby to make sure no one castrated him!

In the end, we unlocked him and sent him home naked and scurrying with his balls tucked between his legs. I'm sure after what we put him through, he will never dress like a tourist at Folsom Street Fair again!

With a fresh makeover, black stiletto high heels and a skin tight faux leather dress, she is ready to bend over for an intensely humiliating femdom strapon threesome. Denali Winter is here to help make sure that we stretch and stuff this crossdressing submissive slut's ass as far as she can go!

What a little show-off! Tammy loves being the center of attention, especially when there is a camera involved! She especially likes to expose her little clitty to a room full of dominant women. Even when she is completely hard, her little dick is tinier than my smallest boot heels! Some submissives might be embarrassed by such short comings, but TV Tammy flaunts it, taking it as a sign that she is meant to be our SPH (small penis humiliation) sissy forever!

Speaking of shoes... I've been saving up all my smelliest boots to torture this special slut! Breathe deep, my kinky little shoe sniffer!

Good thing she bribed everyone with new makeup before the shoot, now we have at least ONE reason to be nice to her. Using the inflatable butt plug we "make room" for our cocks inside her, pumping it up until we can see her stomach bulging.

I am impressed by her dildo capacity in this shoot - she has clearly been practicing anally since last time. Every thrust gets her closer and closer to the edge of orgasm. I have to back off from playing with her clitty to prevent her from blowing her load too early. I want to get my BIG dick into her before we allow our subbie to have an orgasm.

When she is finally allowed a release, I'm shocked by Tammy's output. Sooooo much cum spurting from such a tiny little cock - it gets everywhere in a big messy finale!!!

Do you envy Tammy or fear her fate?

She lays on more spanking, then advances this sissy to a bigger, bright pink buttplug with more vigorous pegging. We take turns on her, and Felicity's ass gradually opens beneath our insistent pounding but still won't hold the biggest butt plug all the way inside.

Mistress J is intent on getting the biggest blackest dick in Sissy Felicity's collection all the way into her ass next, so she better "think loose thoughts!" This massive double-ended dong is an intimidating challenge.

With her heels in the air and her ass exposed, we prod, torment and penetrate Felicity as deeply as possible in this femdom humiliation threesome with plenty of SPH, tease and denial.

Further ass-stretching is certainly going to be a part of this sexy crossdresser's homework!

Today we are picking on lucky Sissy Felicity! After a very long time talking about maid uniforms, stockings, garters, breast forms and more, she is ready for her first makeover.

Felicity wants to be the BEST SISSY POSSIBLE. She came prepared with bags full of panties, garters, stockings, multiple dresses, wigs, shoes and enough dildoes to start a sex toy shop!

She is so pale that we use the lightest foundation in our arsenal to lay the foundations for a beautiful transformation. Eyeshadow, eyeliner and lipstick go on next with LOTS of blush for our shy virgin. Once she looks properly feminine and fetching, we crown her with a long blonde wig.

She also gets DOUBLE PANTIED to cover that naughty wet spot!

We teach her how to walk in extraordinarly tall pink sparkle high heels, pad her bra and put her into the pinkest sissy maid uniform ever! She could easily pass cosplaying Princess Toadstool from Super Mario Brothers!

The fluttering false eyelashes add a whole new dimension for Mistress J as Felicity gets into sucking her first strap-on. The camera brings out Felicity's inner slut and she confesses how many men's cocks she has sucked. Mistress J uses her mouth and I probe her ass until she is air tight.

Enjoy this full transformation as we take a boy from bike-riding Sillicon valley techie to cock-sucking sissy slut!

Experienced chastity submissives and keyholders alike know that it is not as much fun if you know when you're going to get unlocked! It is also good to remind them that just because mistress unlocks them, that doesn't mean that they get to have an orgasm.

We are in New Orleans for DomCon when I lose a bet against Zombie. I promised him a blowjob as his prize, but I didn't agree that I would unlock him from chastity! How much can he enjoy oral sex while still trapped? Let's find out!

Time to see if I can reach his hardening cock through the grooves in this cock cage. I stretch as far as I can and just barely manage to lick the tip of his dick, only succeeding in getting him harder and more excited. It is a good thing that I have such a long tongue!

I eventually even add a vibrator for maximum tease and denial in this special femdom scene... but nothing I do manages to defeat the device. I guess he is stuck for now!

I have noticed MAJOR discrepancies between how big a man CLAIMS to be online and how big his dick really is once you meet in person!

This video illustrates the difference between a tiny cock that is fit for chastity, cbt and t&D... compared to a nice big studly penis, plus some suggestions for how to extend your assets if fate has been less then kind. Cock extenders are available for you babydicks out there but it will be hard to get off under that thick layer of rubber!

I also detail the punishments for lying about your penis size in your online profiles... you don't want to get fucked with the punishment dildo! It will put your teeny weenie to shame!

Denali Winter is about to collar their first chastity slave, so this is a valuable learning opportunity about the special kind of desperation, horniness and bondage that a lifestyle chastity relationship can bring out in submissives. Even formerly strong, intelligent, formidable leaders turn into jelly after some heavy bondage and cbt with tease and denial!

We put him into a rubber gimp suit with mits underneath so he cannot escape, then up the ante even further by lacing him into a bondage sleepsack! Mistress Valentina is very lucky to have such a dedicated and deeply submissive slave.

The best part is when he screams THANK YOUUUUUUUUU as the pain becomes overwhelming. I wonder what people thought in the other hotel rooms?

DomConLA is a kinky hotel takeover convention with famous lifestyle and prodoms from around the world. Enjoy my ongoing coverage of these incredible people during a unique event!

When Sissy Stephanie shows up with a bulging suitcase, it raises a lot of eyebrows. Look out, all that rubber bondage gear is heavy! She manages to get her luggage up the steep dungeon steps, already passable en femme complete with high heels! I enjoy how Stephanie travels comfortably in public as a woman to our kinky humiliation porn shoots. She passes so well that no one has figured out her bulging chastity secret yet!

We don't know exactly how old she is, so I've teamed up with the cruel Mistress Vyra and Maniacal Mistress Sofia for some special occasion punishment and a sadistic femdom foursome. Our plan is to "spank her until WE are satisfied" since age is just a number.

During the spanking, we "massage" our sissy on the inside with the remote-control vibrating butt plug, while she drools around the ball gag keeping her from mouthing off. This is the most drool I've seen in a long time! Her cheeks "pink up" quite nicely but she is an inexperienced submissive with an especially sensitive ass. Even though her pain tolerance is tiny, her balls are huge! Maybe extended chastity will incentivize masochism for her in a new motivating way.

Once the plug is firmly in place, it is time for MORE Bondage!!! Before she can resist, we put her into a multi-layered hood and even thicker, more restrictive, latex sleepsack. It is so tight that you can see her nipples straining and stretching against the rubber! The more helpless she becomes, the more I want to grope her.

While she struggles, the vibrator buzzes and hammers away at her prostate, I enjoy adding another layer of bondage using my special pink rope. Mistress Vyra plays butt plug DJ with bass vibrations strong enough to rattle the entire bondage table.

With the plug constantly changing vibration patterns and a Hitatchi Magic Wand on her caged clitty, this sissy doesn't stand a chance against us! What will happen next? Stay tuned to the ongoing saga of Sissy Stephanie!

Slave Onyx first needs to be dressed in latex from head to toe latex to protect him from the cold, inescapable metal. We zip him inside an industrial heavy rubber prison suit by Studio Gum that covers EVERY inch of him with built in gloves, all custom made with a built-in gas mask. He'll be totally immobilized once the cage is screwed down. There is absolutely no extra wiggle room for our helpless Onyx.

We share fun stories about chastity adventures along the way, since she and her slave are beta-testers of the Dream Lover 2000 long distance "male management system."

Once the cage is suspended from chains on an industrial swivel mount, we have him at our dizzying mercy.

Mistress Gwen and I use a wide range of "stimuli" to "provoke some responses" from our captive experimental test subject. I wonder how he will respond when we add breath control, pussy sniffing and special gas "treatments" to the mix...