Locked into the blindfolded hood, YourSissyJoy must grope through a chalice full of almost identical keyrings to draw out her own chastity key! If she wins, Joy gets a treat but each time she chooses the wrong keys, it is time for a punishment instead!

Every incorrect draw from the chalice increases YourSissyJoy's peril, adding a dozen locks, cruel nipple clamps and a ball gag to her torment in the metal bondage. All this playtime and chastity has pushed her right to the edge. Even after all that, Joy still has to draw her own key from the chalice in order to win a chance to orgasm!

This shoot was brought to you by the power of ALL THREE HOLES.

Welcome to my depraved triple penetration scene! Some of you were confused when I first announced this video, wondering "what is the third hole?" The first two are obvious, I could tell immediately which fans have the kinkiest imaginations and which of you refuse to contemplate the possibility of urethral sounding.

Depending on how the sounds are used and how big they are, I can make this incredibly painful or more like "an orgasm in reverse!" Always remember to use sterile lube for this kind of invasive playtime and follow up with cranberry juice! I change my gloves frequently in this scene, enjoying extra opportunities to snap the medical rubber onto my hands.

Don't confuse "winning" an orgasm with earning one, this sissy has worked hard behind the scenes for an opportunity to get unlocked, regardless of the consequences. An "opportunity" for an orgasm is also not a guaranteed one. Sounding has a way of stealing or ruining orgasms because they are so overwhelming. This scene itself is a reward. My attention is a reward, even when it is cruel.

Let's find out if YourSissyJoy can take this... It won't be long before you will learn to crave sounding with even bigger toys!

Sometimes a virgin ass is a hot commodity and other times it is more like a liability.

Bitchboi has the perfect nickname for someone about to be bent over for the first time. Will this bitch be able to TAKE IT?

He is so nervous! He sent me lots of revealing photos via fetlife while we flirted but reality is a little scarier. I bet I can help him open up with plenty of bondage and prolonged teasing. Gradually, his ass starts to open up for my hands and toys and he gives up that booty cherry to me.

If I collect enough virginity points, I get to redeem them for prizes!

Bitchboi eventually earns a special treat by being a sweet, submissive little sissy bitch and following all of my orders to the letter. He even went out in public to buy multiple pairs of pretty pink panties for his close up. Those panties are getting tighter and tighter the more we play.

Since I like the way the panties look on his bulging sissy cock, I leave them on for a forced bondage orgasm using my powerful hitatchi magic wand vibrator. Cum looks SO COOL squishing out through multiple pairs of panties!

Even all the layers of tight silky fabric couldn't prevent this sissy slave from blowing a huge load for me.

If you watched the 1980's sitcom "Full House" then you will recognize the famous view of the iconic "Painted Ladies" Victorian houses overlooking the park in this exclusive San Francisco neighborhood. We are out for a ride in the unseasonably beautiful weather at one of the biggest, famous and most picturesque public parks in the city, Alamo Square.

Tindala is such a brave exhibitionist pony to go outside in full fetish gear! I think of this as a kind of "positive publicity" or kinky outreach. San Francisco natives and tourists alike take it all in stride as we put this pony through her paces literally and figuratively.

Broad daylight femdom pony play bondage - maybe we should offer rides on the Embarcadero next?

It is hard to keep a human pony in a tiny apartment, they need regular exercising and physical challenges!

"Have you been trading those treats for depraved sex acts with your fellow inmates? The sadistic femdom guards of my special sissy prison are going to torment the truth out of you!"

We know it is someone from the sissy cell block. The only solution is to interrogate EVERYONE using PAIN to motivate snitching. You can hear peals of cruel laughter all the way from the guard shack if you listen carefully, we've been betting on which of you will crack first.

Bambi watches and delivers orders from their fortified location over the crackling loud speaker while Denali and I get our hands dirty roughing them up.

When intimidation alone doesn't lead to an immediate confession, we make them kneel on rice. The first to confess gets to stand up and MIGHT get leniency!

"Is this the meanest thing we've ever done to you?" Minute by minute the pain of kneeling on the hard kernels on the cruel concrete takes its toll.When they say yes, we add spanking and caning with a metal rod.

"Do you miss the rice yet?" We taunt them as they cry.

"A clenched asshole is a sure sign of a guilty conscience!" Time for a body cavity search to get to the bottom of this mystery!

Featuring some of the most experienced lifestyle and professional femdoms in the world, we push the limits in otherwise unshockable New Orleans. We have enormous artistic freedom when it comes to fetish wear in the streets because it is "another day on Bourbon Street."

This year DomCon New Orleans runs October 10-13th 2019. Be sure to check out my Crossdressing Pageant, Sunday at 12:30 on the main stage! Come enjoy classes, play parties and kinky adventures in the Big Easy. We even get our own parade!

Here's a time lapse of the 2018 DomCon NOLA Special Guests - can you spot your favorite mistress in the video?

At no time is Greyhound completely out of bondage. There's no more important time for additional restraints than when unlocking them from chastity. Greyhound is an escape artist and I know we are going to use ALL of the straps on their tightest locked settings.

"Eye contact is a priviledge and not a right!"

You can see Greyhound go through so many different emotions in this video, the full range of fear, arousal, pain and pleasure play out across their face. The special blindfold allows me to see their expression but they only see a confusing blur. I like to see the fear in a submissive's eyes and the flush of arousal on their cheeks when I start to fuck them. This is the first time Greyhound's vagina has been allowed any pleasure or penetration in more than a year!

I use my vibrator on the chastity belt's shield to edge Greyhound, rattling their cage until they start to whimper, struggling not to have an orgasm without my permission. Finally it is time to unlock my prize and have my way with her.

Before pleasure there must be pain and a Wartenberg wheel is perfect for sensitizing her most delicate folds. Pure cruelty but she responds to it with enthusiastic arousal, a TRUE MASOCHIST.

I fuck her virgin-tight pussy until she cums again and again and again. There is something especially sexy about the gurgling noises that Greyhound makes while their mouth is full as they have a body wracking orgasm.

This bonus round is especially for my panty sniffing fans, your fetish is more common than you realize. Pheromones are powerful triggers for sexual arousal! I know some women who secretly dab some of their pussy juice behind their ears for subtle allure and extra control over men!

This shoot is also inspired by the erotic power of red satin! My curve-hugging pinup dress and especially my favorite lingerie!

My well-used panties are already VERY wet and that makes them a delicious gag if you put the gusset over someone's mouth. When you look through the leg holes they double as a makeshift bondage hood. Enjoy this celebration of dirty panties!

Here is Sissy Joy's version of the story:

At Mistress Alice's birthday party, I had the pleasure of talking with Alice about her adventures. I mentioned that I would love to play with her and help bring to life some of her fantasies. Low and behold she said something about a sushi bondage shoot. What we came up with was Sushi Served on a Girl (nyotaimori) with a Sissy Bondage spin.

Alice has plenty of kinky friends. She originally planned on sharing me with one other lady. As word spread about what we were plotting, interest grew and in very short time our little shoot became a full lunch party of 5.

I set out to create a menu with plenty of cucumber, avocado and tempura shrimp rolls with some nigiri to add variety. I am sushi chef in my vanilla life, sharing my skills is something that I love doing.

I put together the food and after all the guests arrived, it was time for some serious fun! The women ordered me out of my sissy maid uniform. I was almost naked except for some frilly panties but, under the panties, I wore my Mature Metal Jail Bird chastity device.

Mistress Alice, with the help of all the other Mistresses, proceeded to mummify me in palette wrap. When I was fully immobilized, phase 2 began. With banana leaves, for added aesthetics, they went about placing the sushi all over my body. I saw the pictures after, and it looked better than I imagined!

Now, fully objectified as a human platter, I had to remain still, so that the sushi didn't fall off me and onto the ground. As the food disappeared, more inviting targets, like my nipples, became necessary to satisfy the guests. The air gaps actually were very welcome, in my personal sauna, the cool air felt amazing! Of course with targets exposed, nipple twisting, pinching, and poking ensued. I couldn't even wiggle my toes, since another Mistress was busy painting them.

As time wore on, another target, my locked up "clit", became the subject of debate. Did I satisfy my guests with good food? Did I deserve an orgasm? Would it be a ruined orgasm? Would I ever get my chastity key back???

Jenna Rotten expertly had me on edge 3 or 4 times before handing control over to Mistress Alice, who added to the edging too. It was easy for them to keep the torment going on and on and on. Hands became confusing after that, I think at one point all 10 hands of all 5 mistresses were edging me simultaneously.

I was losing my mind, knowing that I hadn't been granted permission to cum yet and being kept on edge for such a long time!

When they finally allowed me to deliver the "dessert" course, I came about as hard as I ever had cum before. 5 wonderful women, all thanking me for feeding them. I even converted someone who hated sushi, so I fully embraced the reward that they granted me.

Then the real torture began. If you've ever had a hand job continue AFTER such a hard orgasm, you know how sensitive things are. They decided to keep tormenting me, until it went soft or until some ice forced me to shrivel. As soon as my cock was small enough, I felt a familiar cage being placed on me, and heard the all too familiar "click" of the lock on my chastity device.

One by one, Thierielle pierces herself with special candles, turning herself into a human birthday cake with lines of needles running up her left leg and arm (one of the most sensitive places). When she finally has enough piercings and is running high on the rushing endorphins, it is time to light them on FIRE.

This scene combines piercing, wax play, fire, music and light in a unique celebration that fulfills this lifestyle submissive's kinky birthday fantasies. Domina Jenna Rotten is also here for the festivities and helps blow the candles out to make her wishes come true!

Enjoy this self-piercing art project featuring music by Aural Incarnation, using flaming birthday candles mounted on thick piercing needles.

Hope you get exactly what you wished for this year too!

We prepare by enjoying gentle and prolonged enema preparation together. I start building slowly with several enemas followed by stretching, cleansing and then refilling her with warm saline to open her up even further.

I narrate the scene with a tutorial about enemas, how to give them and how to enjoy them! Since we're going deep into her ass for the first time today, we want to make sure she is nice and clean.

Once she is completely cleaned out, it is time for tightlacing corsetry and bondage before she finally loses her anal virginity to me.

Ripping panties off of virgins is one of my favorite kinks, a fetish to be savored, since you can usually only do it once (per hole). I tease and examine Didi as I tie her down, but I can't resist destroying her panties since we can't take them off without undoing all of my bondage.

I have so much fun ripping and cutting up her panties that I decide to make them double crotchless, exposing both her hungry ass and her hardening cock.

Once I penetrate her, every pump and thrust into her ass just inflates her cock harder and harder. I make her beg for a pounding before I give her a mind-blowing handjob orgasm. Didi finally gets fucked like the girl she's secretly been all along...

I think she is going to have an anal fetish from now on.

. . .

Didi likes to mix her pronouns, sometimes preferring to identify as male or as female, depending on her mood. In honor of the significance of losing her virginity, she is female-minded for this shoot but identifies as gender fluid.

"You have a little forest down there... time to get rid of all this unsightly body hair and SHAVE YOU DOWN!" Fortunately, I have a sturdy set of electric clippers. One way or another, I am going to make this sissy presentable.

Crossdressers are often stereotyped as small but this video slut has an impressive cock. All the more reason to DOUBLE PANTY them in ruffled butt rumba panties paired with a naughty whale tail thong underneath. I hope g-strings come back into style soon!

If you're a fan of erotic hair brushing, you'll love the moment when I let down "Rapunzel's" long hair. While wigs offer variety, real hair allows a huge range of sensations. Even if you are bald, the scalp itself is sensual in its own right.

Using the same hairbrush on her sensitive clover clamped nipples almost pushes her over the edge, soaking through BOTH pairs of panties as she gets bigger and harder. I can tell she's going to need a LOT of spankings!

Like Delilah with Samson, I am going to strip you of that pesky masculine power through hair humiliation. Enjoy this feminization romp, I want to find someone to WAX next!

I think all men (not just sissies) should take time to allow themselves to appreciate the unique sensuality of being smooth. Time to say goodbye to your own body hair and enjoy the ride! Remember to moisturize too!

Keep breathing, even though we're going to make that difficult!

Total head to toe control must be ours if you want to earn an orgasm.

We've saved the best for last at Studio Gum Headquarters in Germany... if by "best" you mean the MOST SEVERE of the hoods in their inventory.

Strange Hobbies has endured a wide variety of severe rubber bondage, gags and hoods but hasn't been allowed an orgasm... yet.

Elise Graves suggests a kinky bargain - torment for pleasure. It seems so simple, but it is so devious! He can only enjoy the vibrator if we get to control every part of him! The built in gag in this iconic hood is massive and those are TINY breathing holes.

I'm lusting after their whole collection! I've never seen any other company work with latex THIS THICK and I was stunned to learn that they offer EVEN THICKER customized rubber through internet special orders. This also means that, once inflated, the devices become even more unforgiving.

Deep inside the basement dungeon at Studio Gum Headquarters, we set out to see just how severe their extreme gear can get.

The workshop smells deliciously fetishy with rolls and rolls of latex ready to be turned into bespoke bondage. The incredible sights and smells have everyone in the mood for exploration. Studio Gum creates a panapoly of ultra severe rubber sleepsacks but the WALL OF HOODS is especially irresistible.

It only took a little rest and a good meal after BoundCon in Munich before the whole team was eager to investigate the prototypes and archives of these legendary rubberist inventors. Extremely generous and indulgent hosts, they cheerfully allow us to romp through their gummi wonderland, communicating sometimes in English, sometimes in German, often in gestures and the "universal language" of fetish.

We sang "99 Gummi Hoods on the Wall" to the tune of "99 Bottles of Beer" and the joke took on a life of its own. How could we resist this opportunity to indulge in SO MUCH RUBBER? Elise Graves from Bondage Liberation brought her friend nicknamed Strange Hobbies and we can tell that he is hypnotized by the possibilities.

First, the rubber catsuit to prevent welts from the vacuum cube. Then, once he is completely immobilized, his head is uniquely vulnerable. We start with what we think should be the easiest to handle, then ramp things up drastically.

Controlling his breathing helps him process the pain in this femdom threesome but the vibrator really gets his attention!

Come with me down the red carpet at DomCon Los Angeles and meet some of the participants in the largest gathering of lifestyle and professional femdom BDSM enthusiasts in the world! Let's get to know the fetish fashionistas, heavy corporal players, movers and shakers of this unique community.

Goddess Samantha is the Mistress of Ceremonies this year and shines with over a decade of experience, strength and power.

Ms Monday Jones is a Shamanatrix and mischief maker, they had such a good time at DomCon New Orleans that they knew it was time to double down.

Lucille Ballbuster's favorite activity is obvious but she has a great sense of humor about a huge variety of kinks.

Mist Maze is at DomCon for the first time but she has an excellent mentor and is a newbie specialist when it comes to sessions.

Madame Rose especially enjoys roleplay and unique experiences that let her pull from an extensive theater background.

Goddess Nyx has a lot to teach naughty little submissives but also helped make sure that everyone could find their classes this year by working on the convention's program. There are SO MANY things going on during one of these events that it helps to plan ahead!

Ms Elena De Luca is sometimes called "the hardest working femdom" because she is famous for taking NiteFlirt calls during all kinds of situations. If you're ready to talk about it but not explore she offers both options.

Lady Victoria has no hesitation about her love of crossdressing and transformation scenes as well as ladies and COUPLES. Ever consider getting your partner something truly special that you can enjoy together?

Guest of Honor Master Leigh waxes enthusiastic about heavy rubber in their revealing latex catsuit and everyone seems to agree that part of what makes DomCon so special is the magic of community building in person with one another.

Mistress Satanus is new to DomCon but already feels excited about the opportunity to hang out with dommes from all over the world and celebrate successes with like-minded friends.

Goddess Phoenix, gracious hostess of the Red Carpet Social, indulges us for a brief interview before the start of the awards ceremony.

Our final interview before the big show, Porcelain Midnight also volunteers on the advisory board and emphasizes that it is LOVE that keeps bringing her back. The members of the femdom community have a lot to offer one another. We are not alone.

Consider attending DomCon New Orleans or Los Angeles or one of the other many real life BDSM events happening all over the world. It is worth it to learn about the lifestyle in person if you've only seen examples on the internet so far!

It isn't enough to just surrender and be a good submissive...
A truly GREAT submissive must also be USEFUL!!!

Many people have a fetish for latex because of the special sensualism of the material. It conforms to your body and clings to you so tightly that dressing aids like lube or powder are necessary to help slide and squeeze everything into place. However, rubber is also very delicate!

What kind of soap should you use?
How should you wash this unique clothing?
What about spray-on vs soak treatment shines?
How do you use vivishine, if you manage to find it?

Time to deepen your training to please your current (or future) Mistress!

Learn about how to care for your femdom's precious rubber clothing in this behind the scenes educational video filmed during the True Desires retreat. Goddess Phoenix and Jean Bardot join me along with our host Maitresse Renee in Dallas, Texas.

Goddess Sydney is a vision of Venus in Furs with a sexy manicure, a kinky imagination and a fox stole. She is a true sadist with a wicked sense of humor, especially when it is at a submissive's expense. I find that she is cruel to sissy sluts in a way that makes them BEG for MORE!

I relish this opportunity to use the TIGHTEST setting on the locking institutional straps. We're going to give Sabrina lots of reasons to struggle today! She is terrified of our cocks ripping her tight ass to shreds so we start with a humiliating purple jeweled buttplug to help her stretch.

Our satin sweetheart is also a little shoe fucker! When we bend her over it is immediately obvious that these shoes have been covered in sticky semen over and over again. Her shoes are disintegrating! This calls for extra punishment! Paddling emphasizes her helplessness with pain but it is the emasculation that truly stings. We terrorize her so much that her cock fully retracts, escaping from the chastity device without needing to open the lock. She quakes with fear, knowing more punishments are coming.

Once Sabrina is close to crying, we take turns fucking their mouth until her makeup is running. If we can't fuck her ass yet, it is time to perfect her deep throat blowjob skills! Remember, "a gag is almost as good as a gape from a sissy slut!"

Subby Sabrina is so hungry for cummies that she is willing to lick it off her old jizz-covered shoes. Goddess Sydney knows a perfect shoe gag bondage trick to make sure there's no escape from the smell and taste of those fucked-out heels.

Let's make a bargain: for every pair of shoes we pick out for you, we will let YOU choose a pair of shoes for each of us. Think of it a foot fetish/enforced feminization 2-for-1 deal.

What will the heart and breathing monitors look like when I start to use the cattle prod on their sensitive feet? Will her heartbeat speed up or slow down when I spread her legs for a ruthless pussy spanking? With this level of vital signs monitoring, I will be able to tell what Greyhound fears and desires. There will be no hiding the truth in this medical interrogation, her own body gives her away.

She has not been allowed to have any orgasms, or even any vaginal stimulation, in more than a year. Pain has fully taken the place of sexual pleasure in her 24/7 slave lifestyle. After spending so much time locked in chastity, almost any attention feels like good attention, even if it is excruciating. If Greyhound wants any pleasure, she is going to have to EARN it through suffering.

Enjoy some special behind the scenes banter with the creator of Serious Bondage featuring assistant Dart Tech during this clip, several sites collaborated to make this bondage week all it could be. There's no way to fake it when we are monitoring Greyhound's heartbeat, breathing, oxygen levels and more!

This fun "gender queer pride flag" mummification video began as a fan mail exchange regarding my previous movie featuring a similar scene where I duck taped Denali Winter as a rainbow flag to the Castro Pride Flag in downtown San Francisco. Things quickly escalated from email to real life friendship since this lucky submissive is local.

This is Didi's video debut but I think it won't be her last time in the dungeon. Everyone present before, during and after the scene remarked upon how profound her transformation was when she went from "male" in street clothes, through a chrysalis of duck tape and into makeup while still in bondage.

I redress her in butterfly themed feminine clothing after extracting all of her masculinity through a sissifying handjob. The most efficient way to drain someone of male energy is through their cock so I am going to "milk the man out of her!"

I enjoy some intense female-style orgasm training, then I CUT her out of both the mummification bondage and her old male clothing for a truly freeing experience. We demolish her former gender and she is reborn as a beautiful woman!

The shift in Didi's demeanor, body language, vocal patterns and all around presentation is amazing. True metamorphosis in action!

Come join us on this profound and sexy journey from masculine to feminine!

"I am going to haunt your sexual fantasies. Sometimes 'almost' is worse than none at all. ALMOST is the ultimate torment for an entitled man who THINKS he is in control, an ongoing humiliation for someone who believed he was destined to rule the world."

My specialized treatments are based on overwhelming you with femdom BDSM until you are driven mad with lust. Once broken, then you can be rebuilt!

This Asylum isn't about becoming normal, it is about deepening your perversion! We specialize in secrets here, especially fetishes because, deep down, we share your deviancy

This case of a privileged but unhappy wealthy submissive will take some effort to crack. When you are used to getting what you want, then you forget how to be humble.

It begins simple enough, with a bargain: he can TASTE my nipples, but I get to take away his sight.

I smother him with my breasts once there is nothing he can do about it. My nipples are responsive and sensitive so it isn't long before his cock starts to respond to my pleasure.

I add some cbt rope bondage to the mix while I enjoy a long, slow, tease and denial handjob.

Once we are both at peak arousal, I put on some gloves and lube up his massive hard cock for more vigorous stroking. I alternate gentle and soft with rough and fast strokes, always keeping him on edge, never letting him fully release his load.

Tease and denial can be so much fun because it keeps the edging and arousal going for hours. Add more bondage and alternate pleasure with cbt (cock and ball torture) like this for a mind-blowing combination that your male submissive will never forget!