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  • Delivery Boy Pt 1
  • Crossdressing
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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
     Handjob Slut Training Pt 4 Femdom Couple Seduces Ts
    10 minutes
      Handjob Slut Training Pt 4 Femdom Couple Seduces Ts - Tsamber seduced by couple
pt 4 slut training handjob

i love the way amber looks with clamps on her sensitive nipples. I also enjoy the way she reacts to the pain and pleasure.

tsamber's whole body seems to be one big erogenous zone now that we have her tied up completely. Now is the perfect time to take the sensations to the next level!

while my male submissive plays with her tits, I start stroking her cock in a nice, slow handjob. Her moans get louder and louder as we overwhelm her senses in a delicious bisexual threesome.

i'm already making plans for this slut's gangbang! While I describe how many men and women that I am going to make her pleasure, she almost looses control without permission!


for more real-life femdom videos, visit http://****aliceinbondageland**** also check out my very special site, http://****aliceinsissyland**** for more trans, crossdressing and gender play!  Double Penetration Sissy Pt 4 Strapon Threesome Makeover
    9 minutes
      Double Penetration Sissy Pt 4 Strapon Threesome Makeover - Sissyamy arrival part 4 - spit roasting double penetration

while madame suzanne moans, cusses and fucks sissyamy's mouth, I take a turn at her back door, probing her with my fingers.

a little anal stimulation makes her an even more eager cock sucker. I bet sissyamy wishes that we hadn't locked her into that chastity belt!

suzanne talks a blue streak that makes it clear she was born to weild a cock... And I get so worked up that I can't resist dipping my dick into amy's tight little sissy pussy.

my smallest cock is a tight fit in this new sissy's ass, but by the end of her week she'll be taking mme suzanne's big dick in more then just her mouth.

we give this new sissy a thorough working over until she's riding my cock for all she's worth while also struggling to deepthroat suzanne's massive dick, while we egg her on like the champion slut she is. Amy is getting a double dose of femdom pegging and ***********.

i love double penetration, but I love it even more with suzanne on the other side of my fuckmeat, talking dirty.

join us at http://****aliceinbondageland**** for more lifestyle femdom movies.
     Satin Glove Spanking Pt 2 Panty Drawer Sissy Punishment Femdom
    4 minutes
      Satin Glove Spanking Pt 2 Panty Drawer Sissy Punishment Femdom - Panty drawer punishment pt 2
sissy spanking


i can see that my dirty gym panties are not punishment enough. Time for a spanking!

my green satin gloves are a silky torment to sensitize my sissy's skin before delivering swift femdom justice in a bare-handed spanking... Until my sissy boyfriend's pretty pink ass matches the stolen pretty pink panties!

i also notice that "she" is wearing my frilliest floral lace garter belt and sexy stockings...


for more femdom videos with bondage, lingerie play and more, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****  Satin Glove Handjob Pt 3 Panty Drawer Sissy Punishment Femdom
    3 minutes
      Satin Glove Handjob Pt 3 Panty Drawer Sissy Punishment Femdom - Panty drawer pt 3
satin gloves handjob tease

nothing feels better then satin gliding against smooth, sensuous satin... And what better place to enjoy that sexy feeling then against your helplessly hard cock?

now that I have caught my sissy boyfriend going through my panty drawer, I know that I am going to have to start forcing him to wear panties every day.

i use my deep green satin gloves as tools of torment and delight in this teasing handjob. 
i enjoy reprogramming him with pleasure. Now my sissy is helpless to resist the siren call of my panty drawer...


for more lifestyle femdom videos with heart and passion, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****
     Stinky Panties Pt 1 Panty Drawer Punishment Sissy Femdom
    4 minutes
      Stinky Panties Pt 1 Panty Drawer Punishment Sissy Femdom - Panty drawer punishment pt 1
stinky panties punishment


i know my boyfriend has been secretly wearing my clothing while I am out of the house, the furtive glances and tell-tale stretching of my favorite panties hinted at his naughty behavior... But until now I was missing the proof.

i bought a gadget on the internet that would set off a silent alarm when my panty drawer was opened.

i told my slave that I was going to a tea party, but instead secretly waited downstairs. I knew my slut would give in to dark, secret desire, it was only a matter of time. He simply can not resist the siren call of my panty drawer...

watch me spring this trap and catch my sissy boyfriend rifling through my panty drawer! How should I punish this transgression? Definetely stinky panties?

this is the culmination of your biggest fantasy... And your worst nightmare, to be caught red handed???


check out more videos and genderplay at http://****aliceinbondageland**** and http://****aliceinsissyland****  Jail Cell Suspension Bondage Pt 2 Cbt Rubber In Ballet Boots
    10 minutes
      Jail Cell Suspension Bondage Pt 2 Cbt  Rubber In Ballet Boots - “gumbi ******* around in ballet boots… part 2”

now that my slave is helplessly suspended from the ceiling of this custom jail cell, I am ready to take the bondage (and the latex) to the next level. I begin by adding a heavy rubber hood with a built in rebreather. Some people also call it a “breath bag.” This will dramatically reduce the amount of oxygen he gets, rendering him even more dizzy and helpless as he dangles above the floor for me… trussed up in head to toe latex, incredible sky-high ballet boots and tight leather straps! He is completely immobilized for my pleasure and amusement (plus my *****-ment).

i don’t even bother to remove his under hood - which still has an inflatable gag and blindfold in place. Now the layers are getting tighter and tighter. Do the walls feel like they are closing in, yet?

gumbi is a very special slave, with an insatiable love for latex and heavy rubber bondage… as well as for severe cock and ball ******* (cbt for those of you who are acronym fetishists).

before our play began, I made sure to add spikes to the chastity device hidden under his sleek and sexy black rubber catsuit!

i particularly enjoy his helpless, blind, deaf and dumb state in this video. I love caressing him through the layers of rubber, especially how our lubed-up latex encased bodies slide erotically against one another. I also enjoy emphasizing his helplessness as he dangles weightlessly. However, the fun really begins when I tear off his latex codpiece to reveal his hardening cock in its spiked sheath!

“look at how fucking turned on you are!” I exclaim, revealing his substantial member. He moans helplessly as I examine my growing target, squeezing it, testing it against the chastity device (in this case a “gates of hell” with added spiked rings). The more aroused he gets, the more he suffers for me. The harder his cock gets, the more he suffers for his lust!

… and then I start to add the weighted clamps to his cock and balls!

… and then a vibrator to make him even more turned on and sensitive beneath those spikes!

this gives me a great idea, so I add yet another layer of cbt bondage and lace his whole cock (still in the gates of hell) into another layer of spiked agony. Now his whole cock belongs to me - in layers of painful bondage.

i love the close-ups of his cock stretched tightly against the laces… and I especially enjoy the way I can swing him back and forth using the weights attached to his balls as a very intense, intimate leash.


see more videos, photos, blogs and stories at ****aliceinbondageland****

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

i've also set aside all of my cbt play for you heavy enthusiasts over at http://****aliceincbtland****

now you can find whatever side of my femdom universe that you are looking for!

    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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      Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom

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      Sissy Public Handjob Chastity Schoolgirl Uniform

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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

    Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome

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      Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome

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      Chastity Check Part 1 Sissy Femdom Mistress Threesome

    Chastity Check Part 1 Sissy Femdom Mistress Threesome

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      Puddles The Sissy Full Movie Wet Mistress Showers Outdoor

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      Record Setting Strapon Anal Part 2 Mistress Femdom Bondage

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      Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice

    Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice

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      Dino Dick Giant Strapon Fucking Mistress Aliceinbondageland

    Dino Dick Giant Strapon Fucking Mistress Aliceinbondageland

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      Strapon Handjob Cumshot Breasts Part 3 Femdom Mistress Alice

    Strapon Handjob Cumshot Breasts Part 3 Femdom Mistress Alice

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      Cbt Super Slut Part 2 Femdom Mistress Tease Denial Bondage Bdsm

    Cbt Super Slut Part 2 Femdom Mistress Tease Denial Bondage Bdsm

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      Nipple Worship Part 1 Super Slut Femdom Mistress Bdsm

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      Super Slut Sissy Pegging Strapon Full Movie Strapon Femdom

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      Behind The Scenes Rubber Fetish Latex Interview Dress Up

    Behind The Scenes Rubber Fetish Latex Interview Dress Up

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