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  • Delivery Boy Pt 1
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  • Crossdressing
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  • Pov Caught
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  • Ruffle Worship
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  • Caged Sissy
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  • Brutalized In
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  • Handjob Cumshot Pt
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  • Hypnotic Panties
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  • Otk Spanking Pt 1
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  • Panty Therapy Pink
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  • Permanently
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  • Punishing A Virgin
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  • Red Lipstick Slut
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  • Spanking Sissy Pt
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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
     Rubber Sissy Maid Uniform Part 1 Femdom Mistress Dressup Latex
    14 minutes    		  Rubber Sissy Maid Uniform Part 1 Femdom Mistress Dressup Latex - Latex bondage footjob part 1 rubber sissy maid uniform aliceinbondageland the more I play with this slave's nipples, the more his cock bulges against the chastity cage. The customized bright pink lock matches my special key and proves he has kept his chastity intact without release for a very long time. we are in for a day of fun! We have been friends for a while, so I know all of his bondage and fetish "buttons." panties first! That is my favorite rule when it comes to crossdressing and they are even more fun when they are made out of rubber! next we outfit him in the sexy sissy maid uniform, complete with apron, latex seamed stockings, opera gloves and sexy high heeled shoes!  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!
     Cum In My Dirty Panties Pt 2 Mutual Masturbation Femdom Pov
    10 minutes    		  Cum In My Dirty Panties Pt 2 Mutual Masturbation Femdom Pov - Caught stealing panties - part 2 masturbating together with my panties i know you covet my dirty panties. when I am done fingering my pussy through these sheer pink panties, they will be the freshest ones you have ever sniffed! so go ahead, take my dirty black lace panties out of the hamper. I know you have been wanting to... Put them on while I watch and masturbate! if you manage to please me, perhaps I will let you have these wet, smelly, panties right off of my body when I am done! If I really want to prepare these panties for my sniffing slut, I should get as turned on as possible while wearing them... It arouses me even more when I can see your reaction. so, show me your hard cock, barely restrained in black lace. I want to see how turned on you are for me and my panties! see more of my real-life femdom video adventures at http://****aliceinbondageland**** for more crossdressing and genderplay, check out 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.
     Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment
    16 minutes    		  Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment - Crossdressing maid punishment - part 5 ballet boots training in uniform now, after being tormented for almost a full hour, finally putting on the pvc sissy maid’s uniform feels like a relief. He submits to the final pvc crossdressing, broken and **********. i ordered my new slave to wear a french maid’s uniform to a kinky tea party and he disobeyed. This elaborate, perverted, forcedcrossdressing scene is his real-life punishment for failing to do as I ordered. to my surprise, the more I ***** this “average joe” masculine submissive into women’s clothing, the more aroused he gets. My newbie sub claims that this is because he gets off on pleasing me and I so obviously enjoy feminizing him. He claims to be “helpless” to prevent himself from getting hard even though the panties frighten and embarrass him. now he is ready for more “advanced” training. i have prepared a pair of ballet boots - the highest of high heels - for his sissy maid graduation! I do so enjoy my fetish heels! i leave him dangling, thoroughly confused about his gender and sexuality, yet incredibly aroused. for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!  Just The Handjobs Femdom Couple Seduces Ts Tgirl
    32 minutes    		  Just The Handjobs Femdom Couple Seduces Ts Tgirl - Tsamber seduced by couple just the handjobs i know what you want to see... You're in it to watch a sexy latex-clad couple torment a captive tranny with sensual handjobs while my male slave ties up her supple body. I won't rest until I have corrupted tsamber into the perfect bisexual slut! first, we tie amber standing up in the center of the living room and enjoy her breasts as well as her growing shemale cock. once I coax one shuddering climax out of her, we tie her securely to the chair for even more milking! join me for weekly updates at http://****aliceinbondageland**** and check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!

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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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