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  • Delivery Boy Pt 1
  • Crossdressing
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  • Caged Sissy
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  • Please Note

    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!
     Puddles The Sissy Full Movie Wet Mistress Showers Outdoor
    27 minutes

    2014-08-31
      Puddles The Sissy Full Movie Wet Mistress Showers Outdoor - Puddles the sissy full movie sd aliceinbondageland

puddles is an extra-kinky sissy with a "thirst" for exotic degradations.

we share taboo fantasies about watersports paired with inescapable bondage so I know it is going to be a good day to stay hydrated. Time to add latex fetish clothing, a sissy maid uniform and also time to invite a friend over for maximum mischief!

mistress minax joins me for a soggy day in the sun, featuring the famous serious bondage "deck cell" for our wet fantasies. We can just hose him down once we are done with him!

after all, no one has "perfect" aim! We are very glad that rubber is waterproof!  Record Setting Strapon Anal Part 2 Mistress Femdom Bondage
    19 minutes

    2014-08-24
      Record Setting Strapon Anal Part 2 Mistress Femdom Bondage - Footsub giant strapon part 2 dino dick aliceinbondageland

sometimes a slave promises a mile but gives an inch...

i am here to settle a bet with footsub to see if he really can beat my anal stretching champion and become the new reigning ass king of my website.

so far, I am impressed by the size of his strap-on toys and butt plugs. I also like his stories of anal exploration, but let's see if his ass can deliver what his mouth has been promising!

i task him with taking all of the brand new "dino dick" from mr s, only then he will get to enjoy my feet as a reward!
     Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice
    15 minutes

    2014-08-17
      Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice - Footsub giant strapon part 1 bondage chastity aliceinbondageland

we have so much in common that it was just a matter of time before I put footsub on camera for some kinky confessions and movie mischief! Both of us love ass play, and have deep appreciation for sexy feet and boots.

the cb series of plastic chastity devices are famous, but he's one of the rare few who have dared to try the pa5000 device because it requires a prince albert genital piercing in order to secure your sexuality.

footsub's series of piercings lets me attach rope bondage to some very "personal" rigging points as I tie him down for some deep anal probing using the "dino dick."  Dino Dick Giant Strapon Fucking Mistress Aliceinbondageland
    33 minutes

    2014-08-10
      Dino Dick Giant Strapon Fucking Mistress Aliceinbondageland - 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.

    Random Alice In SissyLand Clips more
     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!  Masturbate For Me Pt 7 Ts Seduced By Femdom Couple
    5 minutes
      Masturbate For Me Pt 7 Ts Seduced By Femdom Couple - Tsamber seduced by couple
pt 7 ****** masturbation

we won't rest until we've milked tsamber for every drop of her cum...

so now that we've already ****** her to have multiple climaxes, now I order her to play with herself in front of us, so we can enjoy yet another orgasm from her, this time exhausting all of her sissy cream in one big cumshot blowout!

with four hands all over her in this bisexual threesome, tsamber's slutty side really shows.

when at last she is exhausted and drained completely of sexual fluids, we make out and untie her, still caressing her helplessly sensitive body. This is a scene none of us will ever forget!


for more lifestyle femdom videos, visit http://****aliceinbondageland**** check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!
     Sissy Maid Punishment Full Movie Femdom
    59 minutes
      Sissy Maid Punishment  Full Movie  Femdom - Crossdressing maid punishment - full movie


“enforced crossdressing” videos seldom live up to their reputation. In fact, for most sissy subbies, it takes very little pressure at all to put them into panties.

yet still, the fantasy of being ****** into panties by a beautiful woman is incredibly compelling. In this spirit, I present a crossdressing video that is really under duress.

my slave gets more aroused and more confused the more I feminize him.

this newbie submissive disobeyed my order to dress in a pvc sissy maid uniform for my special tea party. He claims to be a straight “manly man.” This is his punishment.

first, I bind his hands high above his head so that he will be helpless to resist. Then, I begin to break apart his rough, tough, straight male exterior piece by piece, mercilessly taunting him with each ruffled, girly, lacy, pretty piece of clothing that I have picked out for him.

i raided the entire costume department of a famous fetish studio to put this incredible feminine outfit together. Panties, stockings, garters, petticoats and more panties… it all culminate in his first ballet boots walking lesson!

watch me take this straight boy and turn him into my perfect sissy slave slut!



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

for more gender play, check out http://****aliceinsissyland****  Panties Corsets Heels Pt 3 Caught Wearing Panties
    9 minutes
      Panties Corsets  Heels Pt 3 Caught Wearing Panties - Caught wearing panties -
part 3: panties, corsets and heels - oh my!

“it was just a panty thing… I never intended for things to go this far!”

now that we have double pantied, corseted and locked this poor delivery boy into pink lingerie, he is bargaining, begging and pleading for release. 

the mad dr. Wildefyre believes that we have finally ********* our perfect experimental test subject. She is certain that pushing him right over the edge of ****** crossdressing insanity will reveal a crucial insight into the workings of the human mind, especially when it comes to gender and sexuality. She will stop at nothing to see this man undone by his own frilly fetishes!

every piece of women’s clothing is locked in place on this hapless cowboy who is now our helpless dress up dolly. The camisole locks behind his back. The corset ties are locked at maximum tightness. His black police-style subjugation hood is offset by a pretty pink satin ***** mask. His delicate hands are protected from vicious steel handcuffs by opera-length pink satin gloves. However, even the s&w handcuffs binding his wrists so unforgivably are custom made in powder pink.

this is only the beginning. The mad dr. Wildefyre is very thorough!

welcome to asylum diabolica… the dr. Is in… sane!


this is day 1 of 5 days that paulette spent with us at the headquarters of 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**** either. Thanks again!

to see more of me, keep coming back to http://****aliceinbondageland**** for weekly updates, stories, blogs, videos, photos and real life bondage adventures.
     Caught Wearing Panties Full Movie Mad Scientist Test Subject
    38 minutes
      Caught Wearing Panties  Full Movie  Mad Scientist Test Subject - This is the ultimate crossdressing fantasy movie.

the mad doctor wyldefyre, aliceinbondageland and laughingsadist have all joined ****** to create a nightmare/fantasy world for this submissive.

he has never met any of us in person.

we ****** this delivery boy, discover he is already wearing panties and then fling him head-first into the deep end of forcedfem, femdom and heavy lingerie play.

corsets, panties, heels, oh my. A cinderella style cage for a twisted game of sissyball. This video is incredible. It has it all. One of the pinnacles of sissy play and my favorite all time scene!!!

for more of my video adventures, visit me at http://****aliceinbondageland**** - and check out http://****aliceinsissyland**** for more gender play, forcedfem and crossdressing!  Pov Caught Stealing Panties Femdom Confrontation Masturbation
    18 minutes
      Pov Caught Stealing Panties Femdom Confrontation Masturbation - Caught stealing panties - full movie - pov femdom confrontation


from now on, you will be buying panties for both of us and I am throwing away all of your boxers!

that's right, only frilly panties for my little panty slut from now on!!!

i walk you through your future as my little panty slut before I ***** you to masturbate with my dirty panties from last night... I can't resist playing with myself, fingering my pussy while I watch you stroke your cock. I'm turning you into my perfect little sissy slut.

a delicious dressing down and lingerie show from your mistress alice...

for more of my videos, visit http://****aliceinbondageland****

for more crossdressing and genderplay, check out http://****aliceinsissyland****

    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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      Puddles The Sissy Full Movie Wet Mistress Showers Outdoor

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