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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 Milking Pt 5 Ts Seduced By Femdom Couple Bisexual Threesome
    4 minutes
      Cock Milking Pt 5 Ts Seduced By Femdom Couple Bisexual Threesome - Tsamber seduced by couple
pt 5 ****** orgasms


ts amber continues to get more and more sensitive and aroused the more we play with her. Soon she is going to loose control and gush her sissy juices everywhere!

both of us have been fondling, pinching, stroking and probing her while she is tied up helplessly in the living room. Her moans have grown louder and louder and her sissy clitty is at maximum hardness. This is the perfect opportunity to take advantage of her.

i think she would do anything for release... Little does she know that we will not untie her simply because she has an orgasm. This is just the beginning of her night with us!


see more of my lifestyle femdom videos at http://****aliceinbondageland**** and http://****aliceinlatexland****  Masturbate For Me Pt 7 Ts Seduced By Femdom Couple
    5 minutes
      Masturbate For Me Pt 7 Ts Seduced By Femdom Couple - Tsamber seduced by couple
pt 7 ****** masturbation

we won't rest until we've milked tsamber for every drop of her cum...

so now that we've already ****** her to have multiple climaxes, now I order her to play with herself in front of us, so we can enjoy yet another orgasm from her, this time exhausting all of her sissy cream in one big cumshot blowout!

with four hands all over her in this bisexual threesome, tsamber's slutty side really shows.

when at last she is exhausted and drained completely of sexual fluids, we make out and untie her, still caressing her helplessly sensitive body. This is a scene none of us will ever forget!


for more lifestyle femdom videos, visit http://****aliceinbondageland**** check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!
     Panty Punishment Pt 2 Sissy Maid Punishment Crossdressing
    6 minutes
      Panty Punishment Pt 2 Sissy Maid Punishment Crossdressing - Crossdressing maid punishment - part 2
pressured into panties!


my lust for feminization is enough to turn my slave on… and confuse him a whole lot in the process. He has never crossdressed before, yet he finds it arousing.

since it turns me on, he cannot help but be turned on. The most difficult part about this scene is how my slave is unable to control his cock’s responses to my sissification.

i love embarrassing this slut by pointing out his arousal, constantly taunting and reminding him that he could have avoided this whole mess if he had only worn the one little slutty dress that I picked out for him in the first place. Now there is no escape and I won’t rest until he looks like a pretty pretty princess!

since my slave always claims that “cleavage is his favorite part” of women, I also dress him in a lovely white bra with breast forms to fill out his blossoming girlish figure.

“enforced” crossdressing movies are such a popular genre, but there is almost never any actual *****. They are more like “please, please, please crossdress me” movies. This is a real straight boy being punished, but aroused, by what I subject him to. I enjoy his confusion and distress as he begins to get hard, wearing panties against his will.

i find a way to make him enjoy this pantied punishment.



for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!  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****
     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!  Sissy Masturbation Vintage Lingerie Pt 2 Pete The Pantyboy
    22 minutes
      Sissy Masturbation Vintage Lingerie Pt 2 Pete The Pantyboy - Pete the pantyboy part 2

sissy masturbation exposure!

poor pete didn't know what he was getting into when he agreed to come play dress up with me! He looks so cute in pink chiffon and satin, with layer after layer of ruffled petticoats and frilly panties underneath.

all of these pretty feminine clothes just turn on my naughty little panty wanker more and more and more... His cock bulges so much through the panties that I can't resist revealing it and stroking him off with yet another pair of panties!

now he is wearing three pairs of panties for me. I masturbate in my white satin panties and then ***** him to wear them on his face. Now he is wearing four pairs of panties. This is more then poor pete can handle, so I make him gush his sissy juices for me.

i like what a little slut he is for my panties. The world would be a much better place if everyone was as honest with their fetishes as pete the panty boy!


for more crossdressing, bondage and kinky videos, come visit me at http://****aliceinbondageland**** and 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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