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  • Delivery Boy Pt 1
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  • Crossdressing
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  • Ruffle Worship
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  • Handjob Cumshot Pt
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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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    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
     Oral Sex Pt 6 Sissy Sex Training Femdom Crossdresser
    12 minutes    		  Oral Sex Pt 6 Sissy Sex Training Femdom Crossdresser - Sissy sex training part 6 - mutual oral sex - pussy licking & cock sucking i make my sissy nuzzle and pleasure my pussy through my red satin panties before allowing her to taste my sex. You can see the growing wet spot as we get more and more sexual with each other. this is a big moment for my sissy - she is going to loose her anal virginity to me today! but first... She has to make me cum with her tongue! i reward my little sissy with a teasing blow job, before reminding her that sissy cocks are for playing with and not fucking. If my sissy wants to get off, it will be with my strap-on cock firmly lodged in her ass. i insist that from now on she must refer to her ass as her "sissy pussy" instead as I educate her about womanhood and female dominant sexual slavery. for more sissy and femdom kinky videos, keep coming back to me at http://****aliceinsissyland**** and http://****aliceinbondageland****  Satin Glove Handjob Pt 3 Panty Drawer Sissy Punishment Femdom
    3 minutes    		  Satin Glove Handjob Pt 3 Panty Drawer Sissy Punishment Femdom - Panty drawer pt 3 satin gloves handjob tease nothing feels better then satin gliding against smooth, sensuous satin... And what better place to enjoy that sexy feeling then against your helplessly hard cock? now that I have caught my sissy boyfriend going through my panty drawer, I know that I am going to have to start forcing him to wear panties every day. i use my deep green satin gloves as tools of torment and delight in this teasing handjob. i enjoy reprogramming him with pleasure. Now my sissy is helpless to resist the siren call of my panty drawer... for more lifestyle femdom videos with heart and passion, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****
     Handjob Cumshot Pt 9 Sissy Panty Drawer Punishment Femdom
    1 minutes    		  Handjob Cumshot Pt 9 Sissy Panty Drawer Punishment Femdom - Panty drawer pt 9 happy endings i've been teasing and tormenting my sissy boyfriend ever since I came home early and caught him in the act of going through my panty drawer. He was even dressed up in my lingerie with a pretty little sundress on! after an hour of talking dirty and planning his permanently pantied future, we are both incredibly worked up... however, if my sissy is to truly be my girlfriend from now on, we can't have sex the way that we used to. My sissy will have to learn how to give up control of her cock and sexuality to a stronger, more powerful, superior woman. From now on, I decide when, and if, she will have an orgasm. fortunately, I am feeling merciful after terrorizing and teasing my poor sissy for hours. Maybe she has earned a reward? the way to a sissy's heart is through her panties, after all... Especially when those panties are creamy! for more authentic femdom videos and lifestyle bdsm explorations, check me out at http://****aliceinbondageland**** and http://****aliceinsissyland****  Sissy Maid Rubber Polishing Part 2 Mistress Femdom Rubber
    13 minutes    		  Sissy Maid Rubber Polishing Part 2 Mistress Femdom Rubber - Latex bondage footjob part 2 rubber polish metal bondage aliceinbondageland putting on the rubber clothing is just the beginning of the fun. as true fetishists know, polishing the latex to a mirrored shine is an important aspect of the kinky rubberizing ritual. mistress aliceinbondageland discusses the pros and cons of using lube or polish to treat your rubber stylishly and without a mess while she transforms her crossdressing sissy maid into a glossy fetish object. then it is time for mistress to get a polish that will tighten her sissy's chastity belt. When a sissy gets grabby, it is time for more bondage using massive metal handcuffs!
     Chastity Breasts Lingerie Pt 2 Sissy Amy Makeover Threesome
    16 minutes    		  Chastity Breasts Lingerie Pt 2 Sissy Amy Makeover Threesome - Sissyamy arrival part 2 - chastity belt, breastforms & lingerie suzanne and I enjoy putting our long-term captive into an "access denied" chastity belt. sissyamy forbidden from touching male clothing and her pesky male genitals must be safely tucked away as well! This custom chastity belt makes sure that orgasm is impossible for our slave, while at the same time presenting a nice smooth "feminine" profile. the unique guards on this chastity belt make sure that cutting the locks is impossible. Since only key is safely nestled in my cleavage, sissyamy must helplessly comply with our sadistic crossdressing fantasies if "she" ever wants to jack off again! i especially enjoy how powerful the breastforms are in transforming sissyamy from a dude to a damsel in distress. With a little chest shaving and see-through lingerie it is impossible to tell that those beautiful breasts aren't really hers. They even feel real! We just can't keep our hands off her tits throughout this whole scene. thigh high nylon stockings, panties, high heels and even a tightly-laced corset all add to her feminization dream... Or is it a nightmare? join us at http://****aliceinbondageland**** for more authentic femdom video adventures.  Handjob Slut Training Pt 4 Femdom Couple Seduces Ts
    10 minutes    		  Handjob Slut Training Pt 4 Femdom Couple Seduces Ts - Tsamber seduced by couple pt 4 slut training handjob i love the way amber looks with clamps on her sensitive nipples. I also enjoy the way she reacts to the pain and pleasure. tsamber's whole body seems to be one big erogenous zone now that we have her tied up completely. Now is the perfect time to take the sensations to the next level! while my male submissive plays with her tits, I start stroking her cock in a nice, slow handjob. Her moans get louder and louder as we overwhelm her senses in a delicious bisexual threesome. i'm already making plans for this slut's gangbang! While I describe how many men and women that I am going to make her pleasure, she almost looses control without permission! for more real-life femdom videos, visit http://****aliceinbondageland**** also check out my very special site, http://****aliceinsissyland**** for more trans, crossdressing and gender play!

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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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      Public Rubber Sissy Palace Of Fine Arts San Francisco Femdom

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      Sissy Public Handjob Chastity Schoolgirl Uniform

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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

    Sissy Puddles Bondage Wetting Part 3 Femdom Mistress Threesome

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      Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome

    Puddles Sissy Wet Bondage Part 2 Outdoor Femdom Rubber Threesome

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      Chastity Check Part 1 Sissy Femdom Mistress Threesome

    Chastity Check Part 1 Sissy Femdom Mistress Threesome

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      Strapon Handjob Cumshot Breasts Part 3 Femdom Mistress Alice

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