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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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  • Caged Sissy
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  • Caught Wearing
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  • Sissy Maid
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  • Ballet Boots Jail
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  • Brutalized In
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  • Handjob Cumshot Pt
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  • Hypnotic Panties
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  • Nylon Foot Fetish
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  • Otk Spanking Pt 1
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  • Panty Gagged
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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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  • Satin Glove
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  • Spanking Sissy Pt
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    All content on Kinky Clips is Role Playing Fantasy only.
    All content is consensual and is acted out by models of legal age.
    Random Clips more
     Rubber Sissy Maid Uniform Part 1 Femdom Mistress Dressup Latex
    14 minutes    		  Rubber Sissy Maid Uniform Part 1 Femdom Mistress Dressup Latex - Latex bondage footjob part 1 rubber sissy maid uniform aliceinbondageland the more I play with this slave's nipples, the more his cock bulges against the chastity cage. The customized bright pink lock matches my special key and proves he has kept his chastity intact without release for a very long time. we are in for a day of fun! We have been friends for a while, so I know all of his bondage and fetish "buttons." panties first! That is my favorite rule when it comes to crossdressing and they are even more fun when they are made out of rubber! next we outfit him in the sexy sissy maid uniform, complete with apron, latex seamed stockings, opera gloves and sexy high heeled shoes!  Panty Gagged Breast Worship Pt 6 Panty Drawer Punishment Femdom
    3 minutes    		  Panty Gagged Breast Worship Pt 6 Panty Drawer Punishment Femdom - Panty drawer pt 6 panty gagged breast worship my breasts feel wonderful rubbing against the silky nylon panties, I can't resist taking my top off so we can play with my breasts together. my nipples get so sensitive when I get turned on! my sissy boyfriend nuzzles and suckles them through my dirty panties for a double treat for us both! check out more lifestyle femdom videos at http://****aliceinbondageland**** and http://****aliceinsissyland****
     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.  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!
     Locked Into Lace Pt 2 Caught Wearing Panties
    15 minutes    		  Locked Into Lace Pt 2 Caught Wearing Panties - Caught wearing panties - part 2: locked into lace we discover that our ********* delivery boy is secretly wearing panties! Dr. Wildefyre wastes no time in bringing out even more sexy, pink, frilly and feminine costumes! Our frilly captive has no idea what is in store for him or if he will ever be permitted to return to his day job again! so there can be “no going back” we cut off all of his drab masculine clothing. Now he can only wear what we choose to dress him in! He has no choice but to endure layers of ruffles! the other ladies and I re-dress him “appropriately” in a sexy pink satin camisole, edged with luscious black lace. The doctor insists that we must padlock the clothing onto our new patient, so that he cannot escape. He continues to protest and bargain with us to escape our clutches but to no avail. This sexy feminine outfit has little rings in the bra straps that are just the right size for our pink locks! so we ***** this poor delivery boy into yet another layer, locking him in lace … before we double panty him. we are this poor delivery boy’s last stop of the day. I know that no one will miss him over the weekend. By the time monday rolls around, that life will be a fading memory. By then, “paulette” will have become our perfect pantied pet… permanently! mistress wildefyre is an incredibly sexy dominant woman. She is an expert at harnessing and controlling the male impulse… as well as an expert in altering it to suit our twisted needs. for those of you who secretly crave ****** crossdressing, our mocking laughter and eager encouragement will echo in your ears and haunt your dreams. Just think, this could be you! this is day one of 5 days that paulette spent with us at the headquarters of http://****medicaltoys**** under 24/7 lock and key at the hands of 3 dominant, sadistic women. mistress amanda wildefyre is a one-of-a-kind pro domme and bondage artist that I have had the privilege to train under. He website can be found at http://****castlediabolica**** this amazing video set would not have been possible without the help and expertise of my friends at http://****seriousimages**** either. Thanks again guys, you have the best toys! to see more of me, keep coming back to http://****aliceinbondageland**** for weekly updates, stories, blogs, videos, photos and real bondage adventures.  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.
     Satin Glove Spanking Pt 2 Panty Drawer Sissy Punishment Femdom
    4 minutes    		  Satin Glove Spanking Pt 2 Panty Drawer Sissy Punishment Femdom - Panty drawer punishment pt 2 sissy spanking i can see that my dirty gym panties are not punishment enough. Time for a spanking! my green satin gloves are a silky torment to sensitize my sissy's skin before delivering swift femdom justice in a bare-handed spanking... Until my sissy boyfriend's pretty pink ass matches the stolen pretty pink panties! i also notice that "she" is wearing my frilliest floral lace garter belt and sexy stockings... for more femdom videos with bondage, lingerie play and more, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****  Strapon Cherry Popping Pt 7 Sissy Sex Training Femdom Crossdres
    11 minutes    		  Strapon Cherry Popping Pt 7 Sissy Sex Training Femdom Crossdres - Sissy sex training part 7 - strap on cherry popping it is the moment of truth - time for little sissy monika to loose her anal virginity to my big, hard strap-on cock. i love how her sissy clitty twitches as I show my slave the big toy that will soon be buried in her booty. You can hear my friend taking a few photos in the back ground. This is a big moment that is worth sharing with the world. after all, you only loose your virginity once! monika kisses and sucks my strap-on dick so that I know she is ready to be a real slut for me. Watch how hard she cums once I plunge into her tight little hole! my sissy sex slave is about to be fully trained! for more lifestyle femdom and real life sissy videos, join me at http://****aliceinsissyland**** and http://****aliceinbondageland****
     Dressing Down Femdom Pov Pt 1 Caught Stealing Panties
    9 minutes    		  Dressing Down Femdom Pov Pt 1 Caught Stealing Panties - Caught stealing panties - part 1 - dressing down did you think I wouldn't find out? i discovered your dark secret in the hamper this morning. i do all of the laundry in this house... It was just a matter of time before I figured out that you were masturbating with my dirty panties. How dare you stretch out my favorite lingerie! first, I dress you down for being a lying panty thief... then I tease you mercilessly with an very intimate solo show - beginning with slowly unbuttoning the lace barely covering my nipples, then playing with myself in my black garter belt and delicious pink sheer panties! for more of my videos, visit http://****aliceinbondageland**** check out http://****aliceinsissyland**** for more crossdressing and gender play videos!  Panty Drawer Sissy Punishment Handjob Full Movie Femdom
    46 minutes    		  Panty Drawer Sissy Punishment Handjob Full Movie Femdom - Panty drawer punishment full movie i catch my sissy boyfriend riffling through my panty drawer and decide that this means he is ready for full feminization. 24/7 girly clothes for him from now on. in order to make him ready for his new life as my girlfriend, I ***** him to smell my stinky gym panties, even sucking my nipple through their soggy crotch. he confesses that is not just about panties, but that he is helplessly devoted to all things feminine. Corsets, gloves, garter belts, stockings, the works. my poor sissy gets so turned on and confused during our talks about sexy clothing that I have to punish "her" with a severe spanking. Clearly her training can't progress until I teach her to sexually submit to a truly dominant woman. this movie has a sexy real life dynamic and a very happy ending. for more lifestyle femdom and ****** feminization videos with heart and passion, come visit me at http://****aliceinsissyland**** and http://****aliceinbondageland****
     Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment
    16 minutes    		  Ballet Boots Uniform Training Pt 5 Sissy Maid Punishment - Crossdressing maid punishment - part 5 ballet boots training in uniform now, after being tormented for almost a full hour, finally putting on the pvc sissy maid’s uniform feels like a relief. He submits to the final pvc crossdressing, broken and **********. i ordered my new slave to wear a french maid’s uniform to a kinky tea party and he disobeyed. This elaborate, perverted, forcedcrossdressing scene is his real-life punishment for failing to do as I ordered. to my surprise, the more I ***** this “average joe” masculine submissive into women’s clothing, the more aroused he gets. My newbie sub claims that this is because he gets off on pleasing me and I so obviously enjoy feminizing him. He claims to be “helpless” to prevent himself from getting hard even though the panties frighten and embarrass him. now he is ready for more “advanced” training. i have prepared a pair of ballet boots - the highest of high heels - for his sissy maid graduation! I do so enjoy my fetish heels! i leave him dangling, thoroughly confused about his gender and sexuality, yet incredibly aroused. for more of my bondage adventures, visit http://****aliceinbondageland**** for weekly video updates, stories, photos and the chronicles of my kinky life!  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 The Alice In SissyLand Studio on Kinky Clips
    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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