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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
     Cbt Super Slut Part 2 Femdom Mistress Tease Denial Bondage Bdsm
    10 minutes
      Cbt Super Slut Part 2 Femdom Mistress Tease Denial Bondage Bdsm - Superslut audition part 2 cbt aliceinbondageland

my superslut is getting super horny! His cock sprang to attention as soon as his lips touched my breasts and now I need to keep him tied up for obedience enforcement!

the only thing that would make his hard cock look sexier is a pair of panties. His cock seems to get bigger and bigger when I dress it up in pretty pink lace panties. Even when I start slapping his cock and balls, it stays hard and proud.

i bind his feet so he cannot protect his balls by closing his legs. Then the real cbt begins! With slaps from my riding crop, pinching, slapping, scratching and squeezing, I explore just how much his balls can take. I think he likes it... Superslut is living up to his name!  Super Slut Sissy Pegging Strapon Full Movie Strapon Femdom
    41 minutes
      Super Slut Sissy Pegging Strapon Full Movie Strapon Femdom - Superslut audition full movie strapon bondage handjob hd aliceinbondageland

superslut is living up to his name! He took one look at my "advanced" sized strap-on dildo and asked me if that was the biggest that I had. We are pulling out the truly large dicks for this stretchy anal slut.

he worships my breasts, nibbling and sucking on my nipples while I moan. I can tell he enjoys pleasuring me in bondage, because his cock gets harder and harder, leaking precum everywhere. More bondage is always my answer to escalate a fun scene to the next level!

the only thing that would makes a hard cock look sexier is panties. His cock seems to get bigger and bigger when I dress it up in pretty pink lace. Even when I start slapping his cock and balls, it stays hard and proud.

i stretch him with my fingers and fuck his face with my dildo. He has a skilled mouth but I can tell that his throat will need more cocksucker training before it can deepen and take as much as his ass does. Once he opens up beneath my fingers, I flip him onto his back for some vigorous anal pounding. Let's see if I can fuck an orgasm out of him while I stroke his hard cock.
     Ruffle Worship Petticoats Pt 4 Sissy Maid Punishment
    12 minutes
      Ruffle Worship Petticoats Pt 4 Sissy Maid Punishment - Crossdressing maid punishment - part 4
ruffle worship petticoats


i will completely reprogram this straight boy into my perfect prissy sissy princess!

this first-time cross dresser disobeyed my orders and has earned a crash course in ****** feminization!

i know that the soft, sensuous clouds of petticoats are irresistible to this self-described “texture fetishist.” It feels like sexy cotton candy and his cock bulges through the sheer layers. I am compelled to add layer after layer of petticoats until his hardening cock is lost in the fluffy, feminine, lace swirls.

the lessons continue with twirling, posing and prancing, but the tiny slutty panties my sub is wearing do nothing to conceal his embarrassing erection.

i have to double panty my slut to keep his cock constrained and under complete control.

these white ruffled rumba panties add another layer of *********** and arousal, especially while I ***** him to count, one after another, all of the pieces of women’s clothing that he is wearing.

i am transforming this newbie sub to serve my twisted crossdressing fantasies. Step by step I am stripping away his masculinity and training him to be my perfect sissy maid!


for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!  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!
     Handjob In Bondage Pt 6 Ts Seduced By Femdom Couple Threesome Bi
    5 minutes
      Handjob In Bondage Pt 6 Ts Seduced By Femdom Couple Threesome Bi - Tsamber seduced by couple
pt 6 handjob chair tie

my submissive and I give our captured tranny amber a few minutes to recover from her ****** orgasm... But instead of giving her a chance to escape, we tie her to the throne and continue or sensual torment.

her cock is already getting hard again and I noticed that there wasn't a lot of fluid involved with her first orgasm. I am convinced that this ts is still full of cum and I intend to milk it out of her one way or another!

we tie tsamber securely to the throne and continue playing with her through the night...


see more of my real-life femdom videos at http://****aliceinbondageland**** http://****aliceinsissyland**** and http://****aliceinlatexland****  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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      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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      Chastity Check Part 1 Sissy Femdom Mistress Threesome

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      Chastity Panties Strapon Slave Part 1 Femdom Mistress Alice

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