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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
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    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
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    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
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    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!

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     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.  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****
     Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom
    19 minutes    		  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****  Cock Teasing Pt 3 Ts Seduced By Femdom Couple
    8 minutes    		  Cock Teasing Pt 3 Ts Seduced By Femdom Couple - Tsamber seduced by couple pt 3 cock teasing now that tsamber is in bondage, the bulge in her panties is impossible to hide. I find her cock to be hard, smooth and very sensitive! the slightest touch sends her shivering. I love playing with someone so responsive. My slave and I are seducing this bisexual tranny into complete submission. once her arms are bound, her clitty cock doubles in size and hardness. jackpot! We've found a bisexual bondage slut with a great rack and insatiable kinky desires. What happens in vegas stays in vegas... Unless it is on video! for more lifestyle femdom videos, visit http://****aliceinbondageland**** check out http://****aliceinsissyland**** for more trans, crossdressing and gender play!
     Ass Fingering Pt 4 Sissy Sex Training Crossdresser Femdom
    12 minutes    		  Ass Fingering Pt 4 Sissy Sex Training Crossdresser Femdom - Sissy sex training part 4 - ass fingering a virgin my insistent probing slowly starts to open up monika's virgin ass and soon my whole finger is buried inside of her. i am going to teach monika to enjoy her little sissy pussy and it won't take long before she will learn to have orgasms from being fucked that way, by women's strap-ons and eventually even men's big hard real cocks. her sissy clitty cock is certainly massive and hard, too big to fit into her stolen panties, so I pull them aside to stroke it. the more I probe and stroke, the harder and more helplessly aroused my sissy sex trainee becomes. I think she will learn to enjoy her role as sex slave! ... Especially once I start leaving lipstick prints all over her hard cock and ***** her to pleasure my breasts! for more lifestyle femdom and sissy adventures, come join us at http://****aliceinbondageland**** and http://****aliceinsissyland****  Double Penetration Sissy Pt 4 Strapon Threesome Makeover
    9 minutes    		  Double Penetration Sissy Pt 4 Strapon Threesome Makeover - Sissyamy arrival part 4 - spit roasting double penetration while madame suzanne moans, cusses and fucks sissyamy's mouth, I take a turn at her back door, probing her with my fingers. a little anal stimulation makes her an even more eager cock sucker. I bet sissyamy wishes that we hadn't locked her into that chastity belt! suzanne talks a blue streak that makes it clear she was born to weild a cock... And I get so worked up that I can't resist dipping my dick into amy's tight little sissy pussy. my smallest cock is a tight fit in this new sissy's ass, but by the end of her week she'll be taking mme suzanne's big dick in more then just her mouth. we give this new sissy a thorough working over until she's riding my cock for all she's worth while also struggling to deepthroat suzanne's massive dick, while we egg her on like the champion slut she is. Amy is getting a double dose of femdom pegging and ***********. i love double penetration, but I love it even more with suzanne on the other side of my fuckmeat, talking dirty. join us at http://****aliceinbondageland**** for more lifestyle femdom movies.

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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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