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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
     Otk Spanking Pt 1 Sissy Sex Training Femdom Crossdresser
    10 minutes
      Otk Spanking Pt 1 Sissy Sex Training Femdom Crossdresser - Sissy sex training part 1 - 
otk spanking

when I come home unexpectedly early, I catch my sissy boyfriend dressed up in my clothes and jacking off! He's wearing my favorite pink rose print sundress and is wearing my favorite pair of pink satin panties.

leave it to a sissy to steal the girliest clothes in my wardrobe!

instead of interrupting her masturbation right away, I decide to spy on monika for a little while and wait until she's fully erect and as turned on as possible. Then, I barge through the door.

i was only gone for twenty minutes and already she's dressed up like a prissy sissy and jacking off without permission!

i make monika show off her pantied hard-on before punishing her with an over the knee spanking... So that she learns what happens to naughty little ***** when they play with themselves without permission.

my love of spanking discipline is obvious as I correct my sissy's behavior the old fashioned way!


for more lifestyle femdom and sissy training videos, come join me at http://****aliceinbondageland**** and http://****aliceinsissyland****  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!
     Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome
    12 minutes
      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.  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!
     Cock Sucking Training Pt 1 Double Mouth Threesome Strapon
    5 minutes
      Cock Sucking Training Pt 1 Double Mouth Threesome Strapon - Brutalized in ballet boots - part 1 two cocks, one mouth

this cocksucking video is really all madame suzanne's fault. I invited her over to test out sissyamy and she just couldn't keep her dick out of my new slut's mouth.

we had so much fun in that initial scene that now she is back for more. This time, I let suzanne direct the scene, all around her new favorite fetish - seeing how much hard cock she can stuff into sissyamy's mouth! You get to see this a lot in straight porn, but there's nothing as hot as making a sissy bitch airtight with femdom double penetration.

sissyamy is blindfolded and must fumble in the dark using only her mouth to pleasure both of our strap-on dildoes or face whatever punishment we devise. Let's see how long her mouth lasts before we wear it out and bend her over!

for more authentic femdom movies, join us at http://****aliceinbondageland****  Mistress Masturbating Pt 5 Human Furniture Sissy Amy Makeover
    11 minutes
      Mistress Masturbating Pt 5 Human Furniture Sissy Amy Makeover - Sissyamy arrival part 5 - human furniture masturbation - mistress's orgasm

now that we've fucked all of sissyamy's holes, I bring out the hitatchi magic wand. It is great for stimulating submissives through chastity belts and I also use it to good effect on the dildo filmly lodged in her hungry ass.

i give a shout out to mistress sindee in this movie, because she sent her personal submissive to me in kinky san francisco for advanced training. Everything we do to sissyamy will be videotaped and sent to her mistress. If she doesn't behave well, there will be triple hell to pay!

all this sissy fucking, talking dirty and humilation has me very turned on... So while sissyamy is still on her hands and knees with my cock in her ass, I decide to use her as human furniture for some of my own pleasure!

i sit down on top of my sissy to play with myself using the powerful vibrator...

since they are getting in the way, I take off my wet panties and put them down over my sissy's face so she can smell my arousal, but I don't let her watch as I masturbate to orgasm on top of her... With nothing but my sensuous nylon pantyhose between my dripping pussy and her body.

my orgasms are always better when there is tease and denial involved!

join me at http://****aliceinbondageland**** for more authentic femdom adventures!

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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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      Chastity Check Part 1 Sissy Femdom Mistress Threesome

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