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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!

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     Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome
    12 minutes
      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.  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.
     Sissy Amy Arrival Full Movie Stripped Fucked By Strapon
    53 minutes
      Sissy Amy Arrival Full Movie Stripped  Fucked By Strapon - Sissy amy arrival full movie strap-on threesome


mistress sindee has shipped her slave cross country for advance training with me!

since she lives so far away, I am filming all of sissyamy's captivity to share with "her" mistress who can't be here in person. Join us as we embark on the opening of what for this poor slave will be three full days of 24/7 feminization and captivity.

mistress sindee, madame suzanne and I all conspire to make sure that sissyamy has three days of unforgetable public sissification, bondage, chastity and strap-on training! At no point will she be allowed free... Even spending her nights in bondage.

... But first we have to strip this sissy slut of her masculinity and teach her to enjoy both sucking and taking our strap on cocks.

this is just the beginning of sissyamy's "advanced" training.

join me at http://****aliceinbondageland**** for more femdom video adventures!  Pete The Pantyboy Full Movie Femdom Dress Up
    35 minutes
      Pete The Pantyboy Full Movie Femdom Dress Up - Pete the pantyboy full movie


vintage lingerie fun with the sluttiest little pantyboy I have ever met!

he's totally a slave to satin panties and vintage lingerie. He can't get enough of the feel of silky feminine clothing against his skin. Even through three pairs of panties, he is making quite a bulge... Not to mention a puddle of precum.

i get myself off first, then make him wear my dirty, smelly, wet panties on his face.

that's more then poor pete can handle and he soaks my panties with his sissy squirts.

this is a fantastic scene of two real-life fetishists enjoying each other and playing dress up in an incredible collection of real vintage lingerie! Lots of laugher and lots of lust... Just how I like it!


for more crossdressing, bondage and kinky videos, come visit me at http://****aliceinbondageland**** and http://****aliceinsissyland****
     Ass Fingering Pt 4 Sissy Sex Training Crossdresser Femdom
    12 minutes
      Ass Fingering Pt 4 Sissy Sex Training Crossdresser Femdom - Sissy sex training part 4 -
ass fingering a virgin


my insistent probing slowly starts to open up monika's virgin ass and soon my whole finger is buried inside of her.

i am going to teach monika to enjoy her little sissy pussy and it won't take long before she will learn to have orgasms from being fucked that way, by women's strap-ons and eventually even men's big hard real cocks.

her sissy clitty cock is certainly massive and hard, too big to fit into her stolen panties, so I pull them aside to stroke it.

the more I probe and stroke, the harder and more helplessly aroused my sissy sex trainee becomes. I think she will learn to enjoy her role as sex slave!

... Especially once I start leaving lipstick prints all over her hard cock and ***** her to pleasure my breasts!


for more lifestyle femdom and sissy adventures, come join us at http://****aliceinbondageland**** and http://****aliceinsissyland****  Cock Sucking Training Pt 1 Double Mouth Threesome Strapon
    5 minutes
      Cock Sucking Training Pt 1 Double Mouth Threesome Strapon - Brutalized in ballet boots - part 1 two cocks, one mouth

this cocksucking video is really all madame suzanne's fault. I invited her over to test out sissyamy and she just couldn't keep her dick out of my new slut's mouth.

we had so much fun in that initial scene that now she is back for more. This time, I let suzanne direct the scene, all around her new favorite fetish - seeing how much hard cock she can stuff into sissyamy's mouth! You get to see this a lot in straight porn, but there's nothing as hot as making a sissy bitch airtight with femdom double penetration.

sissyamy is blindfolded and must fumble in the dark using only her mouth to pleasure both of our strap-on dildoes or face whatever punishment we devise. Let's see how long her mouth lasts before we wear it out and bend her over!

for more authentic femdom movies, join us at http://****aliceinbondageland****

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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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