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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
     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****  Pov Td Mistress Alice Talking Dirty Vibrator Masturbation
    25 minutes
      Pov Td Mistress Alice Talking Dirty Vibrator Masturbation - Pov true desires masturbation full movie aliceinbondageland

welcome to the true desires femdom fantasy retreat weekend. For 3 days and nights 9 dominant women enslave 10 submissive men for what feels like eternity of full time bdsm service.

the men are being kept naked and in chastity for our pleasure while serving us, but now that it is evening they are all locked into kennels for the night. The mistresses have gone to bed but I am still wide awake and horny.

something about the thought of those 9 men in chastity eagerly waiting downstairs in their cages makes me sooo wet... Since they cannot masturbate, I decide to give myself one orgasm for each of my weekend servants.

i told them exactly what I was going to do after locking up their cages. I wonder if they can hear my moans echoing through the dungeon.

maitresse renee certainly does and catches me masturbating at the end of this fun, *********** pov video with a twist.
     Ass Fingering Bondage Pt 2 Sissy Strapon Threesome Ballet Boots
    9 minutes
      Ass Fingering Bondage Pt 2 Sissy Strapon Threesome Ballet Boots - Brutalized in ballet boots - part 2 ass fingering bondage

i bind sissyamy into a tight reverse leather straitjacket to keep her arms out of the way. With her feet in those sky-high ballet boots, I know it is impossible for my sissy captive to escape.

madam suzanne is eager to pound our little slut with her huge cock, so I make sure to stretch her sissy pussy out with my fingers. She's about to take the biggest dick of her whole life, and suzanne doesn't like to be gentle!

we coax, prod and probe our crossdressed prisoner's ass until it opens wide for our strap-on dildos!

join us at http://****aliceinbondageland**** for more authentic femdom movies.  Behind The Scenes Rubber Fetish Latex Interview Dress Up
    16 minutes
      Behind The Scenes Rubber Fetish Latex Interview Dress Up - Behind the scenes cmm latex interview aliceinbondageland

... Any last words before you officially turn 30?

enjoy this fun behind-the-scenes interview with my camera man turned model, chainmaille mike, as he reflects on turning 30 and the wild year he has had on both sides of the lens since becoming our bdsm intern.

he is our special camera-gimp!

we discuss rubber, bondage, femdom bdsm and crossdressing as well as boundary pushing and ***********.
     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****  Locked Into Lingerie Pt 3 Sissy Maid Punishment
    13 minutes
      Locked Into Lingerie Pt 3 Sissy Maid Punishment - Crossdressing maid punishment - part 3
locked into lingerie 


i am re-programming this slave to enjoy the erotic thrill of wearing women’s clothing… especially lingerie, panties and sexy, frilly, forbidden fetish fashions!

the curve of his ass looks delicious, framed by the feminine white lace garter belt and slutty white fishnetst this new sissy recruit could almost pass for a real woman, from behind, especially in that red flowing wig!

his furry chest and bulging panties give him away as being decidedly masculine so I decide to add yet another layer of lingerie to this confused and aroused young straight boy. The lace bodysuit will disguise his breast forms and chest hair, making him look seamlessly feminine.

instead of acting as a gaffe, however, the lingerie just serves to get this first-time crossdresser even more turned on and his cock stays bulging against the bow of his panties!

the real finale of this film is the high heel boots. Before my slave is ready for petticoats and the pretty pvc uniform i’ve picked out, he needs to be put in his first pair of high heels.

i don’t want to waste any time with nonsense like flats, so I have selected a pair of tall, sexy, slut boots! My slave gulps with fright when he sees the height of the heels I expect him to wear but soon he starts to enjoy the feeling of firm leather encasing his stocking-clad legs. I enjoy the 6-inch platform heels forcing his toes into delicate, feminine points..

join me as I implant my personal fetish for crossdressing deep in this young newbie’s mind!


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

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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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