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  • Delivery Boy Pt 1
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    All content on this site is Role Playing Fantasy only.
    All content is consensual and is acted out by models of legal age.

    Most Recent Alice In SissyLand Videos! more
     Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom
    19 minutes

    2015-01-07
      Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom - Today daisy ducati and mistress denali winter join me for a devious artistic adventure as we ***** sissy stephanie out into the public spotlight! A little bondage keeps her in line and gives the tourists something to talk about. I think she secretly enjoys all the attention in her ultra-short purple sissy maid uniform!

someone started a rumor among the tour buses that we were a famous band here to shoot an album cover. It turned out to be the perfect "cover story" for anything that we wanted to do!

the palace of fine arts is my favorite iconic san francisco tourist destination!

the "ruins" were manufactured on an epic scale for a world's fair by an artist who fervently believed that americans were at a cultural disadvantage compared to europeans, who were constantly surrounded by stonework reminders that bigger and better civilizations have come and gone before them.


when I was new to kink, it was a famous image of fetish diva midori taken by steve diet godde here that took my breath away and made me realize I loved rubber as more then just clothing. I love rubber as a fetish.

it is perfect latex weather for a romp through the most beautiful park in the city!

for more movies putting fun back into femdom, join us at http://****aliceinbondageland****  Sissy Public Handjob Chastity Schoolgirl Uniform
    15 minutes

    2014-10-05
      Sissy Public Handjob Chastity  Schoolgirl Uniform - 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 ****** 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 *********** 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 ****!!!
     Sissy Shower Drinking Femdom Mistress Outdoor Rubber Latex Kink
    5 minutes

    2014-09-28
      Sissy Shower Drinking Femdom Mistress Outdoor Rubber Latex Kink - Puddles the sissy bonus scene aliceinbondageland

mistress minax and I enjoy a sunny but windy day in kinky san francisco.

we are playing at the serious bondage institute so we enjoy taking advantage of their unique cement cell hidden in their deck.

metal restraints, heavy locks and heavy rubber are the flavors of the day so far but we taunt and humiliate our thirsty sissy with threats of what will happen to him once he is helpless.

earlier, we soaked our sissy in the center of a puddle but we cannot be sure if he ingested any of our nectar or not. Time for a funnel in this "bonus" threesome drinking scene featuring both mistress minax as a special femdom guest star.  Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome
    8 minutes

    2014-09-21
      Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome - Puddles the sissy part 3 wetting aliceinbondageland

we are incredibly well hydrated today... Maybe too well hydrated. Desperation has set in and it is time to put puddle's nickname to the test.

our sissy is going to get soaked in this ***********, messy and fun shower scene! How much liquid can two rubber mistresses hold?

the heavy metal bondage keeps our sissy maid locked in place while we enjoy an opportunity for release at his expense.
     Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome
    12 minutes

    2014-09-14
      Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome - Puddles the sissy part 2 bondage aliceinbondageland

mistress minax and I enjoy a sunny but windy day in kinky san francisco.

we are playing at the serious bondage institute so we take advantage of the unique cement cell hidden in their deck.

metal restraints, heavy locks and heavy rubber are the flavors of the day so far but we taunt and humiliate our thirsty sissy with threats of what will happen to him once he is helpless.  Chastity Check Part 1 Sissy Femdom Mistress Threesome
    6 minutes

    2014-09-07
      Chastity Check Part 1 Sissy Femdom Mistress Threesome - Puddles the sissy part 1 intro chastity check aliceinbondageland

i team up with mistress minax in this video shot in the kitchen of the serious bondage institute.

we check in with puddles the sissy to make sure that his chastity device is secure. Along the way, we also discover just how sensitive his nipples are when exposed to a little bit of *******.

he is led out to the deck cell on a sunny day in san francisco by a pair of laughing and very well hydrated femdoms!

    Random Alice In SissyLand Clips more
     Panty Therapy Pink Straitjacket Pt 2 Crossdressing Asylum
    8 minutes
      Panty Therapy Pink Straitjacket Pt 2 Crossdressing Asylum - Crossdressing asylum -
part 2: panty therapy, pink straightjacket & hobble skirt

paulette is still trapped in our clutches and the pressure of her corset is mounting. Knowing the mental state of our patient, we are taking no chances with this latest male-to-female acquisition. She talks incessantly of escaping, claiming that no mistress has ever been able to keep her in bondage and women‘s clothing for long.

no matter how severe the side effects might be… her controversial panty therapy must continue! 

that is precisely why paulette must be kept in the most stringent of locked pink bondage possible… no matter how much “she” protests.

at no time is paulette ever free. She must always be kept under lock and key as part of her feminization treatment, leaving her helplessly out of control of her own circumstances. She has only the jingle of padlocks and chains to comfort her beneath the darkness of two pink blindfolds.

clapped into leg irons, gagged and ****** into custom pink handcuffs, she must now endure an ultra-sexy pvc fetish hobble skirt. This way she’ll learn that “good ***** keep their legs together when they sit down!” Of course, the padlocked pink leather straps are also a wickedly effective reminder!

my favorite part of the ensemble is the custom, locking pink pvc straightjacket! I love the way the jacket’s panty straps padlock over those perfect sissy ruffles!


visit me at http://****aliceinbondageland**** for weekly updates, videos, photos writing and bondage adventures!  Locked In Pink Bondage Pt 1 Crossdressing Asylum
    8 minutes
      Locked In Pink Bondage Pt 1 Crossdressing Asylum - Crossdressing asylum -
part 1: locked in pink bondage

“paulette” has begun to loose track of time spent incarcerated under our “tender” care.

paulette is a top security patient here at asylum diabolica. “She” must have extensive and stringent bondage, 24/7. We have also taken extensive measures to ensure that she is not permitted to touch or wear mens clothing at any time, under any circumstances!

paulette has become the perfect pantied plaything of three dominant and dangerous women.

she has been incarcerated completely under lock and key. After several failed escape attempts, the intensity of the bondage and her ongoing transformation continues to increase. Paulette has been unable to ***** at night, chained to the bed and thinking desperately of release!

in this video, we see the recalcitrant patient being transferred into our maximum security wing! This branch of the asylum is specifically dedicated to our experimental sexuality research, headed by the infamous (and mad) dr. Wildfyre.

though paulette is already locked into her pretty pink panties, we must secure the patient completely before transport. We begin this scene in the back of a rented cube van, after driving for many hours to a secure facility. The bondage chair in which we so enjoy tormenting our sissy captive came from the set of “con air.” Created for a big budget action movie, we found it maximized for artful and effective immobilization.

bondage artifacts like that tend to find my friends and i. Does that mean we qualify as “notorious?”

we ***** this resisting patient into a wig and fuchsia gag, then we padlock and handcuff her into place with pink handcuffs! This is a great taunting and *********** scene as we goad our emasculated patient with the promise of escape.

only dr. Wildfyre and I are crazy enough to take a cowboy, strip him of his cowboy boots… and ***** him into thigh-high hot pink stilletos!


visit me at http://****aliceinbondageland**** for weekly updates, videos, photos writing and bondage adventures!
     Just The Handjobs Femdom Couple Seduces Ts Tgirl
    32 minutes
      Just The Handjobs  Femdom Couple Seduces Ts Tgirl - Tsamber seduced by couple
just the handjobs

i know what you want to see... You're in it to watch a sexy latex-clad couple torment a captive tranny with sensual handjobs while my male slave ties up her supple body. I won't rest until I have corrupted tsamber into the perfect bisexual slut!

first, we tie amber standing up in the center of the living room and enjoy her breasts as well as her growing shemale cock.

once I coax one shuddering climax out of her, we tie her securely to the chair for even more milking!


join me for weekly updates at http://****aliceinbondageland**** and check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!  Nipple Worship Part 1 Super Slut Femdom Mistress Bdsm
    10 minutes
      Nipple Worship Part 1 Super Slut Femdom Mistress Bdsm - Superslut audition part 1 breast worship aliceinbondageland

i met superslut online and we immediately hit it off when we saw each other in person. He has bragged about his anal capacity and kink level. Only time and testing will tell if he was exaggerating or not.

he has a delightfully spankable ass, but I want some pleasure from him before I have my way with his ass. If he's lucky, I will  have my way with his balls for some cbt.

superslut worships my breasts, nibbling and sucking my nipples while I moan. Then he gets more bondage! I can tell he enjoys pleasuring me in his bondage, because his cock gets harder and harder, leaking precum everywhere. More bondage is always my answer to escalate a fun scene to the next level!
     Caged Sissy Plaything Pt 4 Caught Wearing Panties
    6 minutes
      Caged Sissy Plaything Pt 4 Caught Wearing Panties - Caught wearing panties -
part 4: caged sissy plaything

dr. Wildefyre opens this scene with the hottest, most sexually charged, padlocking scene - and the biggest padlock - i’ve ever seen. The highly specialized sissy cage is the centerpiece of her twisted laboratory and has been the subject of much speculation.

once poor “paulette” is ****** into sheer thigh high sparkle pink stockings and ballet boots, we reveal the secret to “cinderella’s cage” - it is on a powered hoist!

this unfortunate sissy was foolish enough to taunt the doctor, claiming that he would be able to escape. Now she has challenged him to remove his hood… the only piece of bondage that isn’t locked in place with a pink padlock!

he has never seen the dungeon before and is rewarded with an incredible view from the ceiling of the enormous medicaltoys facility, now the secret location of asylum diabolica‘s most insane experiment yet!

the doctor rewards his escape artistry with a “spin” around the dungeon, pointing out the bondage cart, spanking bench, rigidcuffs cage and fiberglass iron maiden. The pvc, satin, latex and ruffled sissy and sexy women’s clothing lines the entire length of the warehouse, ******* and ready… waiting for its sissy target.

there are high heels, wigs and doll hoods the likes of which to drive any “masculine” man insane and still the list goes on and on in a dizzying array of highly specialized feminization fetish gear. This cowboy has no idea what he has gotten himself into!

now our sissy is a helpless, bouncing ball - literally - our plaything for the most delightful and surreal game of catch the fetish world has ever seen!


this is the first day of 5 that paulette spent with us at http://****medicaltoys**** under 24/7 lock and key at the hands of 3 dominant, sadistic women.

mistress amanda wildefyre is a one-of-a-kind pro domme and bondage artist that I have had the privilege to train under. He website can be found at http://****castlediabolica****

this amazing video set would not have been possible without the help and expertise of my friends at http://****seriousimages****

to see more of me, keep coming back to http://****aliceinbondageland**** for weekly updates, stories, blogs, videos, photos and real bondage adventures.  Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment
    16 minutes
      Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment - Crossdressing maid punishment - part 5
ballet boots training in uniform


now, after being tormented for almost a full hour, finally putting on the pvc sissy maid’s uniform feels like a relief. He submits to the final pvc crossdressing, broken and **********.

i ordered my new slave to wear a french maid’s uniform to a kinky tea party and he disobeyed. This elaborate, perverted, forcedcrossdressing scene is his real-life punishment for failing to do as I ordered.

to my surprise, the more I ***** this “average joe” masculine submissive into women’s clothing, the more aroused he gets. My newbie sub claims that this is because he gets off on pleasing me and I so obviously enjoy feminizing him. He claims to be “helpless” to prevent himself from getting hard even though the panties frighten and embarrass him.

now he is ready for more “advanced” training.

i have prepared a pair of ballet boots - the highest of high heels - for his sissy maid graduation! I do so enjoy my fetish heels!

i leave him dangling, thoroughly confused about his gender and sexuality, yet incredibly aroused.



for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!

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    Welcome To Alice In SissyLand
    I’m a real life dominant woman with a real life fetish for feminization. I have dated many women, but my first boyfriend revealed to me that he secretly liked to dress up like a girl. I was thrilled! Since those highschool days, I have been falling deeper and deeper down the kinky rabbit hole. Welcome to my website devoted to one of my very favorite fetishes - gender play, crossdressing, transvestites and trannies! Cheerfully, - Alice .AliceInBondageLand.com .AliceInSissyLand.com

    Featuring 83 Clips / 1302 minutes of video!

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      Sissy Shower Drinking Femdom Mistress Outdoor Rubber Latex Kink

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      Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome

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      Chastity Check Part 1 Sissy Femdom Mistress Threesome

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