The contrasting combination of the sleeveless feminine gown detailed in light pink embroidered lace flowers with the shiny black latex catsuit and rubber dollification hood turns me on SO MUCH. I love the juxtaposition of bridal virginal innocence with the inner sluttiness of my sissy rubber doll.

We shopped for this wedding gown in person in the San Francisco Bay Area and were treated with great respect when we were honest that the dress was for him. They were able to help select a lovely dress with a flattering fit and a cathedral length train. That kind of bravery should be rewarded!

However, I also want to make sure that my crossdressing rubber bride is like a virgin for her husband-to-be, so I make sure to lock her cock up in a black silicone chastity device. This way, I know FOR SURE that she will be a good girl until her wedding night.

Until then, we still have a lot of sissification shopping to do! I am going to take her out to the mall for matching shoes, a new wig and the perfect veil. I wonder how the saleswomen at the bridal boutiques will respond? She will also need something old and something new, something borrowed and something blue.

Is every transvestite bride this horny before their wedding?

Mistress Evadne is in her big armchair by the fire, ready for you to sit on her lap like our good little sissy girl. Since a sitting on a cock for the first time is such a special moment, we want to make sure you do it RIGHT. We wouldn't trust that special first time to just anyone, so let us guide and nurture you into the world of sexuality.

Our little Monika is clearly ready to blossom when we catch her playing with her clitty. We enjoy exploring her growing body together in this threesome. Evadne's rigid strapon driving into her might hurt at first, but soon she will learn to sit right down on our dicks and bounce like a good slut. We're going to raise our little sissy RIGHT.

"If you can take Mistress Evadne's whole cock in your virgin-tight sissy hole, then maybe I will reward you." It isn't often that a mistress gives a blowjob, but this is the kind of day that deserves a celebration. I've also found that a little oral pleasure can help make your first pegging a little easier to handle.

Remember, if you get close to cumming, you have to tell me! If you can get that dildo is balls-deep in your hole without crying, then I will let you cum all over my breasts and then suckle your juices off my nipples. They call it sissy milking for a reason! We wouldn't want those cummies to go to waste...

With every piece of feminizing clothing, I notice that my captive gets more and more aroused. I trace the edge of their secret hole through the layers of panties and suddenly they're writhing and moaning. Good thing I've already got them in bondage!

I pull each pair of panties to a different side in order to expose bitchboi's uncut clitty. The combination of different panty styles act like a cock ring made of lace!

There is a magical moment in this video when my sissy submissive starts wringing their hands with fear and excitement. I can tell they are aching to be filled up by the way they respond to the slightest tough. I sensitize them by more and more by running my fingernails up and down their inner thighs. Sometimes a light touch can cause more torment then a cruel lashing, but my sensuous side eventually gives way to sadism.

Clothespins are easy to find and inexpensive, it is also hard to permanently injure someone with them. Though they are easy to use and newbie-friendly to dominants, they can be VERY intense and painful for submissives, especially beginners like bitchboi.

Today, I am conducting an experiment! I found bamboo clothespins instead of the usual cheap wooden ones and I want to find out which style is more painful. They certainly feel harder and make a much more menacing clicking noise, but will they be more painful than the classic clamps? Let's find out!

The feeling of the blood rushing back to bitchboi's sensitive skin is like "pins and needles from hell" when I remove any clamps. Adding a vibrator makes it even more tortuous!

Unfortunately for them, the MEANEST part is when they come OFF...

Sometimes it isn't just a craving for oral penetration that drives kinky men, but an overwhelming need to put ALL of their holes to use. Anal penetration is often next on an explorer's list. Strap-on sex can provide some gratification or relief thanks to the reaction of the prostate glad to certain stimulus, including the possibility of being pleasurably milked! However, I am more intrigued by the forbidden holes and their arcane pleasures...

How do you feel about your urethra?

That precious, delicate, sensitive hole is not something that most men think about very often, unless they are lucky enough to have a piercing. It is also able to stretch to receive a specialized urethral sound. I have heard sounding described as everything between "burning pain" to "an orgasm in reverse" according to other patients. In this medical play threesome, my nurse and I are ready to stretch your holes in ways you might not have expected when you first woke up in our special hospital.

How would YOU react if a beautiful doctor prescribed this advanced CBT treatment ASAP?

My cameraguy won the first round of the Sub War so he gets locked into the Queening Chair. I strap cocks onto his face and chest so that we can enjoy different sized dick options.

I ride his face while sexy switch Alexis gives him a handjob. To make sure we're not being too easy on him, she uses the chains like a twisted cbt fleshlight to torment and arouse him to orgasm.

Will this break him or bring him to a new level of kink?

This is going to be a fun day! Since one of our models is feeling less-than-dominant, I give them a chance to fight among themselves to see who will be the most submissive. My cameraguy gets a chance to see if he can flip the scene with Alexis the switch.

First, I tie her up, then I tie him up. They're both horny and out to dominate each other for my amusement. WHO WILL WIN? Is having an orgasm "winning" or "losing" in this kinky game?

His secret weapon is using pleasure to distract her, since she can't hold on to the top for very long once she gets close to orgasm. This "race to the bottom" scene is magical because it is so erotic to watch Alexis struggle to hold her own and dominate her fellow submissive even with one hand tied behind her back AND while getting fucked...

Is this "topping from the middle" instead of topping from the bottom?

Would you want to be part of this subby sandwich?

Remember folks, SLUT is gender neutral!

They thought they could get away with shoddy henching. Sit and spin! Buttplugs, paddles and spankings for all of them!

Some of the henchies were more successful than others today but to teach them all a lesson, they all must be punished, one after another, in front of each other! Each slut has to watch the sluts before them suffer. Sometimes anticipation combined with imagination can be the most terrible of tortures. This kind of collective torment can be a good bonding experience.

If you are afraid of clowns, then you might want to skip this kinky homage to the Joker.

From now on, maybe they will keep each other on their best behavior? Unless one of them LIKES to be punished...

There are three categories in the Crossdressing Pageant:
- Gown/Catwalk
- Interview
- Talent Competition

If you don't have a prepared piece for your talent, you are "assigned" a talent, putting a condom onto a strapon using ONLY your mouth! I don't know which I like more, the well crafted performances or the enthusiastic sloppy blowjobs!

Judged by world famous femdoms including Porcelain Midnight, Goddess Fae Black, Mistress Ellen and more! I feel honored to be among them on this illustrious stage.

Each of our contestants has given careful thought and effort into crafting their look, perfecting their makeup and learning how to move in their stunning high heels. I appreciate their enthusiasm and their bravery as they put themselves on display in front of the BDSM community.

Some of them are beginners, others have been dressing up for their entire lives. Our pageant features a wide range of ages, styles and passability - all are welcome to join in the competition for the tittle of Miss DomCon LA.

As gender roles and expectations become more fluid, the focus on "passing" has shifted to a focus on being FABULOUS where everyone is accepted as a part of spectrum.

It is exciting to be living in a world where events like this can take place in the open and be celebrated by everyone!

It is going to take a true team effort to stretch Sissy Joy's ass wide enough and deep enough to take this massive strap-on. We start warming her up with their largest butt plug for several hours, including while we go out to lunch! Now that she is DEEP into subspace, it is time for more probing and penetrating!

We have a bet going about how far Joy can deepthroat the dildo, using the colored stripes as a depth gauge. To maximize her potential sword swallowing, we invert the sling. Blindfolded and hanging upside down, she has to find the dildo first before she can suck it. Putting her head lower than her ass means she is in a perfect throat fucking position... as long as she doesn't choke!

After slobbering all over Denali's dick and making a mess, we finally adjust her to the proper fucking position. Since the plug has been stationary for so long, we take a moment to play tentacle monster. All three of us put fingers into Sissy Joy and wiggle them at the same time.

Once we've maximized her chances at being loose enough, the moment of truth arrives. Just getting past the head is an accomplishment! Once inside her, Denali quickly slides deeper than Sissy Joy thought she could take. Nearly halfway in on just the first thrust!

Despite all her fears, Sissy Joy wins the second half of my bet. We increase the pace once her chastity device comes off, making her really work for it, edging her with a handjob but also distracting her with the pounding.

Hitting a new level of pleasure high, Sissy Joy utters the fateful words "anal orgasms are just as good!" Be careful what you say in moments of ecstasy!

Stay tuned for the consequences...

Even for a well hung submissive stud, the threat of chastity is still VERY real. Having a beautiful cock and toned body isn't enough to make you entitled to an orgasm in Bondageland. You have to earn any pleasure you receive, once you're helpless in my leather sling.

I take my time in this slow-building tease scene. It is extra fun to play with a nice big cock because, even though it is a two-hander, I can drive him wild with just one finger tip.

This stunning specimen of masculinity proves that submissives do not need to be feminine in order to be obedient and subservient to female authority. It is a refreshing change of pace to have a slave with thick muscles and a perfect member. It is also perfect for cbt!

I prefer to fuck a submissive with a dildo that is BIGGER than their own, but we are going to need to do a lot of stretching before you will be able to take a copy of your dick!

Everything good comes with practice so maybe you might get to come someday too...

Once you cum, the torment isn't going to stop. Post-orgasm torture is one of the meanest things you can do to a man...

How many orgasms can you have before you BEG ME TO STOP?

Zombie Pup has the dubious honor of being our birthday boy each May and our "celebrations" get more and more outlandish as we make more and more friends among my fellow mistresses.

Tonight, we've squeezed as many people into our playspace as we can (including off-camera folks and guest stars) for a party and now it is time to deliver some very lucky "crowdsourced" birthday spankings! Even just bare-handed, the punishments get intense, leaving handprints with their force.

Miss Freudian Slit and Cricked Rose have scores to settle with our slutty sub and Jenna Rotten kisses his ass (yes, really) after beating him to the edge of what he can handle.

Sadie Synn learned how to paddle by going swat-for-swat against fraternity boys in college! She's got a heavy enough hand but she's truly devastating with a paddle... especially since she made the paddles we use in this scene! Her toys are beautiful and VERY painfully effective.

Mistress Genevieve also likes the paddles she made and you can see the bruises start to form on Zombie's ass as the video goes on. Denali Winter joins in with a smaller, meander toy to deliver their allotment of punishment.

If you watch closely, you'll also see Devan de Sade deliver some blows along with Jackie Blue...

Remember, its not a real birthday until you're cowering in a corner!

Vyra has been teasing us for months with photos of her newest device and we're excited to reveal it to you too. It is a wooden toy with a loud metal ratchet that can pull your balls tight or can give you more wiggle room if you earn a break. The retractable spikes inside of the jaws where the balls are captured are ready to add some extra SPICE.

Most humblers are clumsy to apply, needing more than one domme or an extra hand to hold their balls in place while you tightens the two pieces of wood together. This design lets you capture their balls before tightening the bondage, making it easier and faster to be captured. The ratcheting SOUNDS this thing makes are the best part, adding to the suspense, creating a great "mindfuck" for a nervous submissive.

CBT has always been touch and go with Sissy Joy. Fortunately, the humbler allows her a reprieve without removing the device by loosening the cords. I also like the ability to quickly re-apply the vice with minimal fuss or complicated effort.

Once fully ratcheted down, her balls are painfully crushed and she is held deliciously in a subservient position - unable to stand up or do anything besides crawl. In that frightened, vulnerable position, we enjoy a chance to spank, paddle and torment her, even adding a nice big butt plug.

When the device is tight, any small movement tugs on her balls. Even involuntary winces translates to cock and ball torture. Happy struggling, little sissy slut!!!

Mistress Genevieve missed out on this deliciously messy tradition last year, so she is in rare form tonight, gorgeous, blonde, cruel and polished to a high gloss latex shine. Licking crushed chocolate cake off her rubberized ass hardly seems like a punishment until she starts smothering Zombie with chocolate covered face-sitting.

Our feedee victim chokes and gags while he struggles to breathe, swallow and lick her pussy all at the same time!

One cake is never enough so curvy Mistress Jenna Rotten & Miss Freudian Slit have a delicious red velvet cake with beautiful cream cheese frosting to ruin all over him too. This time, Zombie Pup must eagerly lap all of the sticky mess off their perfectly pedicured filthy femdom feet.

Did the mean ladies step on your birthday cake? Poor puppy! You can salvage some crumbs if you're brave...

If he doesn't have a foot fetish yet, we are one step closer to creating one!

AliceInBondageLand won "Best Bondage Website" and Denali took "Best New Website!" but only one of us got a real trophy. Time for some kinky arts and crafts!

We made an awesome trophy out of Sissy Joy to celebrate our two Bondage Awards but our first Oscar-inspired bondage statue looked nothing like the real trophy. Time for a sissy sequel! Mistress Casanova joins in this time and the four of us will rectify this award show injustice.

This statue has a very extreme stress position so circulation, muscle fatigue, cramps and more will all be an issue. Sissy Joy's goal is to endure for as long as she can for our amusement. For a sleek black look to match my statue, she is encased in a black nylon catsuit with a brand new bright red ball-gag. To keep her in the proper slave position, we add pallet wrap and black duct tape.

Starting with Sissy Joy on her back, we quickly work as a team to trap her legs in a cocoon of palate wrap before we reinforce the bondage with layers of tape and lift her back into a kneeling position. This is where teamwork becomes important, since Joy is helplessly immobilized by bondage on top of bondage!

We take turns with a vibrator, trying to get her to whimper or giggle nervously. Sissy Joy's giggles are infectious and indicate a happy submissive, but also an anxious one. Mistress Casanova is skilled at finding all those special spots that are both painful and pleasurable, but not entirely unenjoyable, even through the l locked chastity cage.

Sissy Joy is a rare flexible submissive who can put her hands fully behind her back, matching the statue's position with no cheating or special effects. Good sluts are hard to find, we're going to keep her!

Some bondage enthusiasts find bondage enormously comforting and a complete kink in its own right, instead of a means to an end. Enjoy this afternoon celebrating sustainable and completely inescapable bondage in a custom leather sleepsack with strategic padding to maximize immobilization and duration.

Eventually, all bondage scenes will develop "hot spots" that limit the length of the lockup. Our goal here is to completely eliminate all movement while still allowing SnugBug to be strapped down for an entire afternoon (or more!) to enjoy the curing and calming effects of true helplessness.

Zip it up, lace it tight, strap it down and then order him to struggle so that I can find and eliminate the wiggle room. I want him to be able to exhaust himself without the bondage giving an inch! That lack of escapeability becomes even more important when I start to control and restrict his breathing too!

While I love to spice things up with pain and pleasure, there is something meditative and sexy about this heavy bondage scene. I think you will eventually learn to like it!

"After a long day of being fabulous, what better way to relax then sit back and enjoy a smoke. I like to keep a little slutty oral ashtray submissive handy for these special relaxing moments.

"Sometimes, when my human ashtray is especially good and swallows every bit of my ashes, I blow smoke in its face. My second hand smoke is quite a treat for a lowly object. Sharing smoke this way can be very intimate and erotic.

"I bet you smoking fetishists at home are so kinky that you even like it when I cough because my big titties bounce so much!

"This is what I do to unwind at the end of a long day of ass beatings, putting men in their place and being a famous dominatrix."

- Domina Jenna Rotten, ProDom from New Orlean

Don't ask what happened to the other 3 henchies...

I love how legitimately freaked out #4 is for most of this scene.

True fear is a powerful and toxic aphrodisiac when you're invoking the Joker. Some of you with a fear of clowns, a dislike of cosplay or an aversion to camp might want to avoid this film. For the rest of you kinky Batman fans, CHOW DOWN ON THIS EPIC BDSM CROSSDRESSING CROSSPLAY HUMILIATION InSaNiTy!!!

I'm going to reprogram him to like what I like - step by step until he is my perfect fetish minion. Since I prefer my captives to be feminine damsels in distress, let's start with panties!

I like panties so much that I add more than one pair, layering a tiny lace g-string beneath a pair of silky full coverage satin panties. Building up feminizing bondage through clothing means she gets more aroused and vulnerable, especially when I add a nice tight corset to hold up her homemade pantyhose breastforms. Once I add makeup and start festooning her with flowers, she starts to enjoy the process a little more. You can see her surrender to her new role eventually, as I make her look more and more like my sexy super-villainess rival.

Once my extreme feminization transformation is complete, it is time to strap her down on the table for a thorough milking. Just like a deadly cobra needs to be milked of its venom, it is safer for the whole evil team if her trouser snake cannot bite anyone! Then she will be safe to enjoy in other ways... Poison Ivy is helpless without her poisons.

Using every means at my limited attention span's disposal, I reforge my once drab henchman into my best approximation of the seductive and deadly POISON IVY. This "new and improved" version will be kinkier, more docile, less toxic and a LOT MORE FUN TO TORMENT!!!

The need to make these mental pictures and scenarios "real" drives my movie making obsession. This controversial scene is one of my favorite personal fantasy fulfillment shoots of all time.

For years, I was inspired by a video of a submissive eating cum out of used condoms. There were so many of them! I couldn't tear my eyes away and it would make me gush every time I imagined doing that to someone. When I finally met the performer at an adult industry convention, I was CRUSHED to find out that it had all been faked using a drink mix. I was so devastated by this "insider knowledge" that I could no longer enjoy the video, knowing that it was all just a huge act faked for the camera.

However, the mental image of a beautiful female submissive (or sissy) drinking the cum out of a huge collection of used condoms wouldn't leave me alone. I'm still looking for an adventurous sissy to endure the sequel, but this amazing kinky woman would have FOUGHT YOU for the right to go first. She wanted it THAT BAD. It is so hot when ultimate fantasies coincide!

We spent months saving up cumshots inside of knotted condoms in the freezer for this very special girl. She has the most genuine whole-hearted cum fetish that I've ever seen. This is the real thing. These really are used condoms. She is really drinking all that semen. She really enjoys it.

Together, let's make porn that is empowering, sexy and authentic.

This is as real as it gets.

Finally, I can masturbate again!

The moment I start dressing down Sissy Monika for arriving late, her clitty starts to swell. I can barely get her bloomers pulled down for a punishment spanking because she is already so big and engorged! It is 100% clear, even before she licks my boots, that Monika Hottie is developing a fetish for being humiliated by dominant women. She is in for an impressive series of "firsts" with me in this throwback episode, including her on camera anal sex debut.

Once I lock Monika down onto the metal bondage stocks, she has to learn how to take my silicone cock deeeeep in all of her sissy holes, one way or another. If she is a good slut, she might even learn to enjoy it!

I love the sissy paradox - the more feminized you become, the bigger and harder you get! Your cock gets so rigid but your ass becomes so yielding. The more insistent your erection, the more warm and inviting your holes become. Crossdressers can be the best of both worlds!

If you need to be comforted during this pegging scene, here's a good mantra:
"It isn't your fault that you're getting so turned on while I fuck you, I'm MAKING you like it."

Using the webcam mounted to my head, Taylor Dawn sees whatever I see. Strapped into special goggles, the 3D technology becomes disorienting very quickly. Once he is confused and pliable, it is time to tighten up the bondage by inflating it with an air compressor. I love how thick Studio Gum's latex is and how good the seals are, allowing me to fill the bladders to their maximum tightness beneath more and more straps.

We can no longer hear or see him beneath the imposing gasmask, so the hospital-style patient monitors become especially important. In some ways, his heartbeat is one of the only tools of communication left. I can see how every touch and every tease effects him. It takes a team to put together this level of medical and sexual equipment. I am grateful to the San Francisco Serious Bondage Institute and also to Dart Tech for helping make this shoot real.

Taylor gets increasingly frantic as we control more and more aspects of his body, soon his mind will follow. We add a bubbler to the mask's hose, making it easy to hear when his breathing speeds up or slows down.

When I begin to play with his cock and balls, his physical response is immediate and extreme. It only takes a little while with my vibrator before he gushes cum all over our heavy rubber gear. I can't resist a little post-orgasm torture but it is almost more than he can handle. Sometimes it isn't pleasure or pain that breaks a man while he is eager and hard but what you do after his orgasm subsides that counts!

How would you feel watching yourself in 3D virtual reality from MY point of view? Would it help you learn to see yourself as sexy?