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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
     Ruffle Worship Petticoats Pt 4 Sissy Maid Punishment
    12 minutes
      Ruffle Worship Petticoats Pt 4 Sissy Maid Punishment - Crossdressing maid punishment - part 4
ruffle worship petticoats


i will completely reprogram this straight boy into my perfect prissy sissy princess!

this first-time cross dresser disobeyed my orders and has earned a crash course in ****** feminization!

i know that the soft, sensuous clouds of petticoats are irresistible to this self-described “texture fetishist.” It feels like sexy cotton candy and his cock bulges through the sheer layers. I am compelled to add layer after layer of petticoats until his hardening cock is lost in the fluffy, feminine, lace swirls.

the lessons continue with twirling, posing and prancing, but the tiny slutty panties my sub is wearing do nothing to conceal his embarrassing erection.

i have to double panty my slut to keep his cock constrained and under complete control.

these white ruffled rumba panties add another layer of *********** and arousal, especially while I ***** him to count, one after another, all of the pieces of women’s clothing that he is wearing.

i am transforming this newbie sub to serve my twisted crossdressing fantasies. Step by step I am stripping away his masculinity and training him to be my perfect sissy maid!


for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!  Red Lipstick Slut Pt 3 Sissy Sex Training Makeup Crossdresser
    11 minutes
      Red Lipstick Slut Pt 3 Sissy Sex Training Makeup Crossdresser - Sissy sex training part 3 - 
slutty red lipstick

i think my sissy will look great in makeup. When we were making out, I accidentally smeared my red lipstick across her lips. I liked the way it looked so much that now i'm going to give her a full makeover! 

before I take my sissy's virginity, it is time to dress her up like a sexy big **** in red, instead of an innocent virgin in pink. I want her in slutty red lipstick and dark eyeshadow before I take advantage of her!

she covers my breasts in red lip prints before we go back to kissing in our sexy red clothes and matching slutty bright red lipstick.

all this transformation play, makeup and girliness has monika helplessly aroused. I know that now she is ready to do anything for me...


for more real-life femdom and sissy adventures, come join me at http://****aliceinbondageland**** and http://****aliceinsissyland****
     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****  Panty Punishment Pt 2 Sissy Maid Punishment Crossdressing
    6 minutes
      Panty Punishment Pt 2 Sissy Maid Punishment Crossdressing - Crossdressing maid punishment - part 2
pressured into panties!


my lust for feminization is enough to turn my slave on… and confuse him a whole lot in the process. He has never crossdressed before, yet he finds it arousing.

since it turns me on, he cannot help but be turned on. The most difficult part about this scene is how my slave is unable to control his cock’s responses to my sissification.

i love embarrassing this slut by pointing out his arousal, constantly taunting and reminding him that he could have avoided this whole mess if he had only worn the one little slutty dress that I picked out for him in the first place. Now there is no escape and I won’t rest until he looks like a pretty pretty princess!

since my slave always claims that “cleavage is his favorite part” of women, I also dress him in a lovely white bra with breast forms to fill out his blossoming girlish figure.

“enforced” crossdressing movies are such a popular genre, but there is almost never any actual *****. They are more like “please, please, please crossdress me” movies. This is a real straight boy being punished, but aroused, by what I subject him to. I enjoy his confusion and distress as he begins to get hard, wearing panties against his will.

i find a way to make him enjoy this pantied punishment.



for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!
     Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom
    19 minutes
      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****  Footjob Cumshot Sissy Maid Part 3 Femdom Mistress Alice Bdsm
    26 minutes
      Footjob Cumshot Sissy Maid Part 3 Femdom Mistress Alice Bdsm - Latex bondage footjob part 3 rubber cumshot aliceinbondageland

ultimately, this is all about one thing... Winning my bet!

another mistress claimed that footjobs were a myth and were not actually possible in real life. Tonight we prove her wrong, with the help of one of my good friends from niteflirt.

to make sure we get the firework cumshot that I am looking for, I have kept him locked up in chastity, getting more and more horny every day. Now he is ready to explode all over my feet, even if it means having to lick up the results!

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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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      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

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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

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      Puddles The Sissy Full Movie Wet Mistress Showers Outdoor

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      Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice

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      Strapon Handjob Cumshot Breasts Part 3 Femdom Mistress Alice

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      Cbt Super Slut Part 2 Femdom Mistress Tease Denial Bondage Bdsm

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      Super Slut Sissy Pegging Strapon Full Movie Strapon Femdom

    Super Slut Sissy Pegging Strapon Full Movie Strapon Femdom

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      Behind The Scenes Rubber Fetish Latex Interview Dress Up

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