The list below shows the content currently available to members of the site. To become a member, click the JOIN button above.
Click to display videos only
Click to display all galleries
001 - 020021 - 040041 - 060061 - 080081 - 100
101 - 120121 - 140141 - 160161 - 180181 - 200
201 - 220221 - 240241 - 260261 - 280281 - 300
301 - 320321 - 340341 - 360361 - 380381 - 400
401 - 420421 - 440441 - 460461 - 480481 - 500
501 - 520521 - 540


GALLERY: 488 / DATE: 4 Sep, 17 / IMAGES: 43 / VIDEOS: 2

Matching Mistress Mischief!

While getting ready for today's strap-on scene, we discovered that all three of us picked out exactly the same dildo!!!

There's something magical about the "Bandit" model that attracted us at Good Vibrations, even though we went shopping separately. It is not too big, yet not too small. We've got the same nice thick dick in all three skin tones for a triple penetration our subby is sure to remember.

Tonight it is time for anal gangbang fun featuring Mistress Leila Valentina, Trixie and my very lucky cameraman.

These cocks are so fat that he struggles to fit more then one in his mouth at a time. We're going to keep all of his holes occupied, until he begs for mercy (or release!).

Once he's licked and sucked every cock in the room, it is time to spank and tenderize his ass before we fuck him, first one at a time and then all at once. His owner, Mistress Leila, is so aroused by watching us take turns with her boyfriend that she takes another turn! She closes out the scene, stretching his hole and forcing him to ride her, widening his hole even further.

Time to make HIM do all the work. Hope he has not been neglecting leg days at the gym! We make a great team with our matching dicks. This sexy anal gangbang was clearly meant to be! Sexual serendipity is the best kind!

Would you be able to have an orgasm while bouncing on a dick this big? Or would your ass steal the show?


GALLERY: 317 / DATE: 1 Sep, 17 / IMAGES: 18 / VIDEOS: 2

My permanently pantied plaything looks adorable in her new Shirley Temple inspired sissy dress.

The more I humiliate Pinky, the harder her cock gets. With my riding crop, I can enforce my dominance through pain compliance without even having to get off of my throne! I can't resist the urge to touch her for very long, though.

Using spanking, stroking and just the right amount of tickling against her secretly sensitive ass, I am going to make this little sissy into my devoted, humiliated slave.

Once Pinky is feeling deeply aroused and submissive, it is time to add BONDAGE. She can struggle all she wants against the metal Saint Andrew's cross - it isn't going to bend or break!

I almost break my sissy's mind instead when I take off my dirty panties and rub them all over her face. Then, while the sexy ruffled underwear still wet and smelling like my pussy, I put them onto my sissy instead. We wear the same size, so there is no reason we can't share panties from now on!

Since I already gave myself an orgasm in my panties today, I force Pinky to have an orgasm in them also!

Now they are OUR panties.

. . .

Do you want to be my panty pal too?


GALLERY: 489 / DATE: 28 Aug, 17 / IMAGES: 14 / VIDEOS: 2

I love the opportunity to explore new bdsm devices and bondage toys! Inventors make the best play partners!

Enjoy this fun behind the scenes video featuring my friends from the Friendly Little Dungeon. Today, we are showing off an especially cruel homemade toy that can squash your testicles flat.

Using slow pressure to build him up over time, I'm looking forward to finding out just how much cock and ball torture his package can handle... and just how flat I can make his balls!

Those aren't fish but you still shouldn't tap on the glass!


GALLERY: 273 / DATE: 25 Aug, 17 / IMAGES: 38 / VIDEOS: 2

Snugbug and I share a love of heavy compression-inducing bondage and rubber.

My cameraman discovered rolls of ultra thin rubber stored along with a heavy, thick latex straitjacket in a forgotten box inside the dungeon's wardrobe. With these magical discoveries we are sure to have a fantastic rubber romp! What a treat!

My heavy bondage aficionado is immediately responsive to the escalating layers of rubber restriction. The concept of COMPLETE IMMOBILIZATION is a little like chasing a mirage. The complete inability to move any part of our body is a difficult and fleeting target that we may never fully "catch" but we will continue to find extreme bondage fun in the chasing of the goal.

Head immobilization is one important facet of that goal that fascinates me and it is one more fetish that Snugbug and I have in common.

Once he cannot move any part of his body and is encased head-to-toe in rubber layers, with a gag and blindfold cutting him off from the outside world, THEN it is time to bring out my favorite Hitatchi Magic Wand vibrator for some INTENSE tease, denial and forced orgasms!

Enjoy this exploration of compression bondage using heavy industrial rubber layers as well as rope bondage to accomplish some very intense mummification.


GALLERY: 487 / DATE: 21 Aug, 17 / IMAGES: 45 / VIDEOS: 3

We're going back to the bridge!!!

Some adventures are just so much fun and so iconic that they beg for a sequel. I feel the call of the Golden Gate Bridge on every rare sunny day in San Francisco. It is time to tie a sissy to the most famous bridge in the world and see how much we can get away with in my home town!

10,000 people or more will see us today as they drive past our colorful "performance art" scene. Even more will see Sissy Stephanie on the internet once this video is posted on my site. I am training her to be a slutty exhibitionist and this sets a new high water mark of truly public humiliation.

Sissy Stephanie is up to the challenge, so we add a butt plug to make our walk more interesting. Cruel Mistress Vyra also comes with us as an enforcer in case our sissy maid tries to run. I'm wearing my favorite rubber Alice in Wonderland dress and we are ready to give the tourists something to talk about. I love how the wind blows our petticoats up, we are all wearing maximum layers of ruffles to take advantage of the gusty weather.

Sissy Stephanie has on her new very pink, very shiny formal PVC maid uniform with a large white apron plus an extra kinky pair of pink locking high heels. I even have pink rope to colorfully tie her to the famous red bridge. The vibrating remote control butt plug gives me a way to reach out and secretly touch her no matter who is watching, perfect for keeping her in line and properly humble!

Dozens of people stop to take selfies with us and the cops think it is hilarious once we promise them that we are not protesting anything. Party on, San Francisco!

Can Stephanie make it all the way across the bridge while plugged and prancing in her special outfit or will she use her safeword before we're satisfied?


GALLERY: 337 / DATE: 18 Aug, 17 / IMAGES: 16 / VIDEOS: 4

Your anal health is important!!!

Enjoy this femdom medical exxxam celebrating prostate health, a sexy re-imagining of your proctologist visits.

The first half of this video doubles as an educational film that is fun to watch with anal virgins or curious significant others. Our tone is fun and conversational until the bondage starts to tighten down around the vintage gynecological table... then he quiets down and begins to enter subspace beneath my skilled hands!

This movie will help you to better eroticize that yearly ritual visit to the Dr. Good prostate health can save your life! We dedicate this movie to our dear friend currently battling prostate cancer. When attending your appointment gets dull, imagine this kinky rubber fetish scene instead.

The bondage is tight and so is my submissive's ass! He might need more frequent checkups, since once a year is clearly NOT ENOUGH to keep his ass pliable. I start with the smallest of three butt plugs but my goal is to stretch him all the way up to the biggest sex toy before I milk his cock. These plugs have bead-like-bumps to help his hole re-learn how to gape.

Once he can stretch wide enough for the biggest toy, it is time to get high tech today in Bondageland!

Each pulse of electricity from the buttplug clenches his ass and flexes his cock, whether he likes it or not. I highly recommend an electrified buttplug to work your ass into shape if you're watching at home and wondering how porn stars can handle the biggest cocks! Combined with an electric cock ring, you can also turn it into a forced milking!

I can't resist using my hands to add even more stimulation, edging my captive patient closer and closer to an explosive orgasm. A healthy prostate in action with added electrotorture should produce PLENTY of gushing seminal fluids, but there is also so much cbt going on that my submissive might have a real challenge ahead of him.

Will the electricity cause or prevent his ejaculation? How high can I turn up the electrosex before he gushes cum all over our sexy latex operating room?


GALLERY: 318 / DATE: 11 Aug, 17 / IMAGES: 50 / VIDEOS: 2

You can say "goodbye" to boxers and briefs forever!

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!!!


GALLERY: 485 / DATE: 7 Aug, 17 / IMAGES: 30 / VIDEOS: 3

We've discovered a treasure trove of ultra rare custom metal bondage gear in the back of a closet at Sybil Holiday's dungeon. She generously offered it to us, free to a good home, but there is a catch... it is all size extra extra small!!!

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!!!


GALLERY: 294 / DATE: 4 Aug, 17 / IMAGES: 25 / VIDEOS: 1

This shoot launched me on a personal obsession with ass hooks as part of erotic bondage! They are now one of my favorite toys!

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!


GALLERY: 207 / DATE: 1 Aug, 17 / IMAGES: 29 / VIDEOS: 2

Footsub GIANT StrapOn FULL MOVIE AliceInBondageLand

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.


GALLERY: 484 / DATE: 28 Jul, 17 / IMAGES: 33 / VIDEOS: 3

This whole video needs a trigger warning!!!

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!!!


GALLERY: 390 / DATE: 25 Jul, 17 / IMAGES: 30 / VIDEOS: 3

You are in for a treat!

This is one of my favorite videos of all time! Everything came together so right in this super extreme bondage shoot featuring black rubber & electric cock and ball torture.

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?


GALLERY: 364 / DATE: 21 Jul, 17 / IMAGES: 41 / VIDEOS: 6

Wrap me in duct tape
Smooth and Shiny head to feet
I'm your "trophy sub"

- Haiku by YourSissyJoy


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!


GALLERY: 483 / DATE: 14 Jul, 17 / IMAGES: 29 / VIDEOS: 3

Every had your mouth washed out with soap? This is a VERY real punishment, the soap is real and so is the suffering.

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?"


GALLERY: 482 / DATE: 8 Jul, 17 / IMAGES: 31 / VIDEOS: 3

I knew when I first met Miss Freudian Slit that we were going to be friends. Her infectious sadistic glee lends every scene a certain sparkle that I think you will enjoy too.

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?


GALLERY: 224 / DATE: 4 Jul, 17 / IMAGES: 17 / VIDEOS: 1

Our scene unfolds in Golden Gate Park, the birds are tweeting as we open on a helpless sissy trapped in the clutches of a wicked schoolyard bully!

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!!!


GALLERY: 220 / DATE: 30 Jun, 17 / IMAGES: 61 / VIDEOS: 1

Where else can you see public bondage like this in real life except San Francisos' Folsom Street Fair???

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!


GALLERY: 481 / DATE: 26 Jun, 17 / IMAGES: 42 / VIDEOS: 3

TV Tammy is our special whore in training and it is going to take a lot of practice to get her slutted up properly!

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?


GALLERY: 205 / DATE: 21 Jun, 17 / IMAGES: 17 / VIDEOS: 2

Sissy Felicity is all dressed up and it is time for a deeper probing of her slutty ass. Mistress J enjoys inflating the butt plug to maximum before adding a vibrator to help her "open up."

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!


GALLERY: 204 / DATE: 19 Jun, 17 / IMAGES: 36 / VIDEOS: 4

Introducing Mistress J! She shines as a sissy-loving femdom as we undress and redress our special slut from drab to drag. She is one of the most talented femdom photographers and sissy makeup artists I have ever encountered.

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!


Click to display videos only
Click to display all galleries
001 - 020021 - 040041 - 060061 - 080081 - 100
101 - 120121 - 140141 - 160161 - 180181 - 200
201 - 220221 - 240241 - 260261 - 280281 - 300
301 - 320321 - 340341 - 360361 - 380381 - 400
401 - 420421 - 440441 - 460461 - 480481 - 500
501 - 520521 - 540