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  • Delivery Boy Pt 1
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    All content on this site is Role Playing Fantasy only.
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    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
     Punishing A Virgin Pt 2 Sissy Sex Training Femdom Cd
    10 minutes
      Punishing A Virgin Pt 2 Sissy Sex Training Femdom Cd - Sissy sex training part 2
 - 
punishing & probing a virgin


my little sissy monika confesses that she's never had anything in her sissy pussy?

and what exactly is a sissy pussy? It is when a sissy is specially trained to take mistress' and men's cocks up her tight little ass. When a sissy is properly trained her ass becomes just like a real ****'s pussy, sensitive and pleasurable to the point of orgasmic!

the more I play with her tight virgin hole, the more erect monika becomes. We make out and she gets harder and harder until I can tell that she is ready to have her cherry popped.

i fondle and probe her through the pretty pink stolen panties until she begs me to take her sissy pussy virginity with my big strap-on cock. She blushes so preciously as I get her ready to be deflowered. 


for more lifestyle sissy training and femdom videos, come join us at http://****aliceinbondageland**** and http://****aliceinsissyland****  Ts Seduced Into Bondage Full Movie Femdom Couple Threesome
    49 minutes
      Ts Seduced Into Bondage Full Movie Femdom Couple Threesome - Tsamber seduced by couple
full movie

we brought home a sexy tranny from a club in las vegas and couldn't resist teaming up on her as a couple. This is a sexy bondage seduction with a bisexual mtf shemale.

amber has very sensitive breasts, which we first bind with white rope... She enjoys the bondage so much that we tie the rest of her up before exploring the growing bulge in her panties.

how many orgasms can we coax from our captured slut in a single night?

what happens in vegas stays in vegas... Unless it is on video!


for more lifestyle femdom movies, keep coming back to http://****aliceinbondageland**** and http://****aliceinsissyland****
     Locked Into Lace Pt 2 Caught Wearing Panties
    15 minutes
      Locked Into Lace Pt 2 Caught Wearing Panties - Caught wearing panties -
part 2: locked into lace

we discover that our ********* delivery boy is secretly wearing panties! Dr. Wildefyre wastes no time in bringing out even more sexy, pink, frilly and feminine costumes! Our frilly captive has no idea what is in store for him or if he will ever be permitted to return to his day job again!

so there can be “no going back” we cut off all of his drab masculine clothing. Now he can only wear what we choose to dress him in! He has no choice but to endure layers of ruffles!

the other ladies and I re-dress him “appropriately” in a sexy pink satin camisole, edged with luscious black lace. The doctor insists that we must padlock the clothing onto our new patient, so that he cannot escape. He continues to protest and bargain with us to escape our clutches but to no avail. This sexy feminine outfit has little rings in the bra straps that are just the right size for our pink locks!

so we ***** this poor delivery boy into yet another layer, locking him in lace
… before we double panty him.

we are this poor delivery boy’s last stop of the day. I know that no one will miss him over the weekend. By the time monday rolls around, that life will be a fading memory. By then, “paulette” will have become our perfect pantied pet… permanently!

mistress wildefyre is an incredibly sexy dominant woman. She is an expert at harnessing and controlling the male impulse… as well as an expert in altering it to suit our twisted needs.

for those of you who secretly crave ****** crossdressing, our mocking laughter and eager encouragement will echo in your ears and haunt your dreams. Just think, this could be you!

this is day one 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 guys, you have the best toys!

to see more of me, keep coming back to http://****aliceinbondageland**** for weekly updates, stories, blogs, videos, photos and real bondage adventures.  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!
     Dressing Up Together In Panties Pt 1 Pete The Panty Boy
    13 minutes
      Dressing Up Together In Panties Pt 1 Pete The Panty Boy - Pete the pantyboy part 1
dressing up together in panties and vintage lingerie


i think that pete's slutty little skirt is just a little too short. His cock is dangling just beneath the layer of pretty lace frills. We can't have that! Panties are just the thing to protect my new sissy's modesty. We can't have that cock dangling down with his garters!

pete is has secretly been a panties masturbator for years and I love this journey of exploration because you can see his excitement, embarassment and eagerness as I make him prance for me and show off his new frilly panties.

we dress in vintage lingerie together, including full coverage satin panties, garters, fully fashioned stockings and even a sexy nylon slip so that we can slide silkily against each other, together in our panties.

poor pete gets so turned on that he starts to make a puddle in his panties - time to double panty him!


for more crossdressing, bondage and kinky videos, come visit me 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!

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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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