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  • Delivery Boy Pt 1
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  • Crossdressing
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  • Pov Caught
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  • Ruffle Worship
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  • Brutalized In
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  • Handjob Cumshot Pt
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  • Hypnotic Panties
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  • Otk Spanking Pt 1
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  • Panty Therapy Pink
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  • Permanently
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  • Punishing A Virgin
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  • Red Lipstick Slut
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  • Spanking Sissy Pt
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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 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!  Hypnotic Panties Pt 5 Sissy Panty Drawer Punishment Femdom
    5 minutes    		  Hypnotic Panties Pt 5 Sissy Panty Drawer Punishment Femdom - Panty drawer pt 5 hypnotic feminized fate this is a different kind of "bedtime story." as my sissy boyfriend cuddles in bed with me, I describe the sexy fate that awaits him in the world of femininity. i lull this slut-to-be into an aroused state describing all of the clothing I expect her to wear in order to be a good and proper **** for me. it isn't just panties... Now I expect my slave to be dressed as a young **** for me 24/7. In time, with good behavior, I will allow her the thrill of sexy and grown up clothes, like a prom dress, corsets and garters. for now, I expect my new "****" friend to enjoy the process of "blossoming" into a young woman under my training. for more lifestyle femdom and transformation videos, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****
     Nylons Lingerie Breast Worship Pt 5 Sissy Sex Training Femdom Cd
    12 minutes    		  Nylons Lingerie Breast Worship Pt 5 Sissy Sex Training Femdom Cd - Sissy sex training part 5 - breast worship in stockings and garters now that monika is wearing makeup and dressed in sexy merrywidow lingerie and garters, she is really ready to loose her virginity like a real slut! i have to teach her about the proper ways to be a good **** and please her partner. She will have to learn all about my breasts and receive special instruction in how I like to be touched in order to become my perfect sissy sex slave. i also dress her in sexy sheer stockings to make her as sensitive and sensual as possible while my friend takes photos of her ongoing transformation. for more lifestyle femdom and feminization videos, keep coming back to me at http://****aliceinsissyland**** and http://****aliceinbondageland****  Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome
    8 minutes    		  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.
     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!  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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      Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome

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