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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
     Locked In Pink Bondage Pt 1 Crossdressing Asylum
    8 minutes
      Locked In Pink Bondage Pt 1 Crossdressing Asylum - Crossdressing asylum -
part 1: locked in pink bondage

“paulette” has begun to loose track of time spent incarcerated under our “tender” care.

paulette is a top security patient here at asylum diabolica. “She” must have extensive and stringent bondage, 24/7. We have also taken extensive measures to ensure that she is not permitted to touch or wear mens clothing at any time, under any circumstances!

paulette has become the perfect pantied plaything of three dominant and dangerous women.

she has been incarcerated completely under lock and key. After several failed escape attempts, the intensity of the bondage and her ongoing transformation continues to increase. Paulette has been unable to ***** at night, chained to the bed and thinking desperately of release!

in this video, we see the recalcitrant patient being transferred into our maximum security wing! This branch of the asylum is specifically dedicated to our experimental sexuality research, headed by the infamous (and mad) dr. Wildfyre.

though paulette is already locked into her pretty pink panties, we must secure the patient completely before transport. We begin this scene in the back of a rented cube van, after driving for many hours to a secure facility. The bondage chair in which we so enjoy tormenting our sissy captive came from the set of “con air.” Created for a big budget action movie, we found it maximized for artful and effective immobilization.

bondage artifacts like that tend to find my friends and i. Does that mean we qualify as “notorious?”

we ***** this resisting patient into a wig and fuchsia gag, then we padlock and handcuff her into place with pink handcuffs! This is a great taunting and *********** scene as we goad our emasculated patient with the promise of escape.

only dr. Wildfyre and I are crazy enough to take a cowboy, strip him of his cowboy boots… and ***** him into thigh-high hot pink stilletos!


visit me at http://****aliceinbondageland**** for weekly updates, videos, photos writing and bondage adventures!  Punishing A Virgin Pt 2 Sissy Sex Training Femdom Cd
    10 minutes
      Punishing A Virgin Pt 2 Sissy Sex Training Femdom Cd - Sissy sex training part 2
 - 
punishing & probing a virgin


my little sissy monika confesses that she's never had anything in her sissy pussy?

and what exactly is a sissy pussy? It is when a sissy is specially trained to take mistress' and men's cocks up her tight little ass. When a sissy is properly trained her ass becomes just like a real ****'s pussy, sensitive and pleasurable to the point of orgasmic!

the more I play with her tight virgin hole, the more erect monika becomes. We make out and she gets harder and harder until I can tell that she is ready to have her cherry popped.

i fondle and probe her through the pretty pink stolen panties until she begs me to take her sissy pussy virginity with my big strap-on cock. She blushes so preciously as I get her ready to be deflowered. 


for more lifestyle sissy training and femdom videos, come join us at http://****aliceinbondageland**** and http://****aliceinsissyland****
     Stinky Panties Pt 1 Panty Drawer Punishment Sissy Femdom
    4 minutes
      Stinky Panties Pt 1 Panty Drawer Punishment Sissy Femdom - Panty drawer punishment pt 1
stinky panties punishment


i know my boyfriend has been secretly wearing my clothing while I am out of the house, the furtive glances and tell-tale stretching of my favorite panties hinted at his naughty behavior... But until now I was missing the proof.

i bought a gadget on the internet that would set off a silent alarm when my panty drawer was opened.

i told my slave that I was going to a tea party, but instead secretly waited downstairs. I knew my slut would give in to dark, secret desire, it was only a matter of time. He simply can not resist the siren call of my panty drawer...

watch me spring this trap and catch my sissy boyfriend rifling through my panty drawer! How should I punish this transgression? Definetely stinky panties?

this is the culmination of your biggest fantasy... And your worst nightmare, to be caught red handed???


check out more videos and genderplay at http://****aliceinbondageland**** and http://****aliceinsissyland****  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!
     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****  Ballet Boots Jail Cell Pt 1 Hogtie Suspension Femdom
    16 minutes
      Ballet Boots Jail Cell Pt 1 Hogtie Suspension Femdom - “gumbi ******* around in ballet boots…”

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 even begins, I make sure to add spikes to the chastity device hidden under his sleek and sexy black rubber catsuit. The codpiece built into this suit allows me to ******* his cock and testicles as much as I want to without having to undress him from his latex encasement.

i particularly love the sexy purple and blue halter-top catsuit that I am wearing in this video. It bares just the right amount of skin and the hidden zipper allows me perfect access to my pussy when I want to pleasure myself (too bad my slave doesn’t get to enjoy it fully yet).

the spikes that line his cock ring mean that ever touch, every bit of arousal, ever ounce of lust is immediately and painfully punished. Gumbi is extraordinarily sensitive and responsive and I love tormenting him; torturing him until he whimpers, begs and even screams for me. Those of you who enjoy gag-talk will love our special language of grunts and growls because he isn’t getting out of his inflated rubber gag any time soon!

i ***** him to wear sky-high sexy high heel ballet boots for me, rendering him helpless to even stand up straight without assistance. There are so many layers of bondage in this scene! These shoes are so severe that they alone could assure inescapability if you locked them on with a matching pair of mitts… but these incredibly shoes are only the beginning of what I have in store for my lucky slave.

when I see how much he is turned on by being ****** to wear sexy shoes for me, I decide to tease him with my own sexy black high heeled pumps. These classic patent leather beauties are my favorite shoes both in and out of the dungeon. I crush his puny cock with the stiletto heel while he moans through the gag and then smother his face with my sexy latex covered ass. I finger my pussy and wipe my juices all over his face… knowing, the whole time, that every piece of pleasure that I give him is also increasing his pain against the spiked cock ring!

but I am still not satisfied with his level of helplessness, so I take it up a notch and put him into a highly specialized leather harness… suspending him securely in an elaborate hog tie! These buckles can’t be beat… especially once I render his hands helpless with inflatable latex mitts that lock down tight!

once he is blindfolded, mittened and dangling from the ceiling, I use his helpless body to pleasure myself and then ***** him into even more layers of bondage.


see more videos, photos, blogs and stories at ****aliceinbondageland****

for more crossdressing and forcedfem, check out http://****aliceinsissyland****

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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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      Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome

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