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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
     Cock Teasing Pt 3 Ts Seduced By Femdom Couple
    8 minutes    		  Cock Teasing Pt 3 Ts Seduced By Femdom Couple - Tsamber seduced by couple pt 3 cock teasing now that tsamber is in bondage, the bulge in her panties is impossible to hide. I find her cock to be hard, smooth and very sensitive! the slightest touch sends her shivering. I love playing with someone so responsive. My slave and I are seducing this bisexual tranny into complete submission. once her arms are bound, her clitty cock doubles in size and hardness. jackpot! We've found a bisexual bondage slut with a great rack and insatiable kinky desires. What happens in vegas stays in vegas... Unless it is on video! for more lifestyle femdom videos, visit http://****aliceinbondageland**** check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!  Dino Dick Giant Strapon Fucking Mistress Aliceinbondageland
    33 minutes    		  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.
     Femdom Footjob Rubber Bondage Full Movie Latex Sissy Maid Fetish
    53 minutes    		  Femdom Footjob Rubber Bondage Full Movie Latex Sissy Maid Fetish - Latex bondage footjob full movie aliceinbondageland today is all about winning my footjob bet! another mistress claimed that footjobs were a myth and were not actually possible in real life. Today 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 keep him locked in chastity for weeks, getting more and more horny. Now he is ready to explode all over my feet, even if it means having to lick up the results! Mmmmm cum-sumption! i dress him in a full rubber sissy maid uniform with latex seamed stockings, high heels, crotchless panties and gloves. We take turns polishing each other sensuously to tighten his chastity belt. Then, I lock him up with huge metal handcuffs, he is helpless before my feet!  Permanently Pantied Jail Cell Pt 3 Crossdressing Asylum
    16 minutes    		  Permanently Pantied Jail Cell Pt 3 Crossdressing Asylum - Crossdressing asylum - part 3: permanently pantied jail cell incarceration silence isn’t golden anymore… it is bright pink! paulette is now double gagged and locked down completely with pink leather straps and even pink padlocks! We’ve gone from “nice and tight” to “nasty and tight!” dr. Wildefyre isn’t gentle as she ****** our captive into yet another layer of sensory deprivation and loss of control. Paulette takes this severe, inflatable, mouth-stuffing gag well for someone who’s never been ****** to suck anything before. The locking pink leather hood has never been worn and requires extensive, forceful “stretching” before it begins to fit our patient. paulette is already wearing a full body set of matching pvc fetish wear restraints. From the custom locking straightjacket, to the hobble skirt we have laced tight, to the tips of her thigh high boots, she is encased completely in pink bondage! complete immobilization is not enough, so we take it to the next level! Time to strap the patient down into an intricate, institutional, full-body reclining wheelchair for transport to her new, ultra-secure jail cell. gone are the pink frilly curtains in her padded cell… and instead she is ready to be encased in steel bars! Paulette is helpless as we wheel her from the transport truck to her new, hard-core prison. after 2 foiled escape attempts, paulette is now in maximum security lock down at our inescapable remote facility as we prepare to peel away yet another layer of “her“ former masculinity! escape is now completely impossible. Paulette will be our sissy slave forever! visit me at http://****aliceinbondageland**** for weekly updates, videos, photos writing and bondage adventures!
     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****  Sissy Public Handjob Chastity Schoolgirl Uniform
    15 minutes    		  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 ****!!!

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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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