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My name's Sissy, I'm a cute sassy lil' girl who loves high heels and crushing dicks to cum in them. Cum to my shoejob and footjob vids!


@sassysissyshoeshop Latest Posts

  • Triple careless ruined orgasm
    Using Sugar Daddy's cockhead as my footstool is so much fun! It definitely cannot stand the sexiness of my feet in black satin high heels that long. But everytime he's about to cum I stop, spitefully ruining his long awaited orgasms, then I go back crushing all there's left of his manhood until he cums again and again. Poor little dick.

  • Bitchy workout on the cockbox
    Fitness time! Oops I almost didn't noticed your stupid penis on the cockbox, right where I wanted to do my workout! Well... This means I will crush your useless dick under my cute sneakers until I squeeze all of the cum out of it doing my workout...

  • Sexy Sgt Sissy's boot camp
    I am sexy Sgt. Sissy, your senior shoejob instructor. Are you ready to get crushed to cum under my knee-high black leather boots? Your little dick definitely doesn't stand a chance against them so be prepared to get your sweet long awaited orgasm ruined under my soles.

  • Triple ruined orgasm under Mistress Sissy's glam pumps
    Using your useless dick as my foot stool is so much fun! I literally can't stop crushing your manhood until you show me your appreciation by cumming multiple times under my sexy lightning bolt pink pumps! Can you stand three ruined orgasms? Will you earn my mercy?

  • Mistress Sissy's foot stool
    Your useless dick is sexy Mistress Sissy's foot stool. Don't whine as she crushes your manhood under her sexy peep toes heels and, please, do not cum early.

  • Ruined three times by bossy Sissy
    Though pleasing my employees is not on my agenda, if ruined orgasms is what they wish for they'll be quite happy knowing I love giving them under my black satin heels.

  • Mistress Sissy's pin-up heels
    Mistress Sissy is gonna tease your poor little dick to cum in her cute black pin-up heels! How long will you last in her sexy cockhead-crushing game?

  • Ruined twice under my platform sandals
    Wearing platform heels always takes the fun part out of it, as I don't feel anything beneath my shoes so it's easier for me not to care about what I crush!

  • Flat shoes vs flat cock
    Teasing, edging, denying your long awaited orgasm is so much fun! Ruining it even more! How about some bittersweet post-orgasm cockhead crush game under my cute flat shoes?

  • Cute Keds cock crush
    Today I'm goin' for a little walk on Step-Daddy's cockhead in my cute Keds and pantyhose stockings, just to show him how much I love crushing his little dick to cum. As I am a bit sassy and naughty I will first ruin his orgasm, then crush his poor cockhead again to more cum.

  • Under Harley Quinn's heels
    You have been taken hostage by the sexy naughty queen of crime Harley Quinn and she's about to crush your defenceless dick just for fun in her 12-inch platform heels. How long will you resist her humiliating game?

  • Pin-up ruins you twice
    This pin-up inspired look is making me feel quite naughty and as a consequence I cannot resist from playing with Step-Daddy's dick just enough! Two ruined orgasms is that bad? Oops...

  • Naughty teacher Sissy makes you cum twice
    As you sweet slaves decided in my Twitter survey, here's the long awaited sexy teacher clip you all were waiting for! Well, at least the 60% of you! I knew my schoolteacher outfit was too hot for Step-Daddy, in fact it didn't take me long to make him cum ruining his first orgasm and then trampling the hell outta it until he did cum again. Did you learn the lesson this way?

  • Transparent heels shoejob
    Here's a long awaited clip for my devoted Slave who bought me these sexy clear pumps! Sounded like a good occasion to wear my virginkiller sweater too and trample the cum outta Step-Daddy's dick on the cockbox. He has no choice but to let me play with his manhood under my new heels, pumping and twisting, until he cannot resist to me anymore.

  • Gamergirl sockjob
    Sexy gamer girl in pink and blue bodysuit is now your - and Step-Daddy's - new obsession. Here I am in my cute D.Va bunny costume and knee socks trampling the cum outta Step-Daddy's defenceless "joystick"! After it's done spurting cum all around I go on playing with it and his sperm for a little while.

  • Lightning bolt heels trampling hot cock pedal pumping
    If you're smart enough to get the reference for the title then you'll probably know how this is gonna end. Sitting in front of Step-Daddy I'm gonna squeeze his cum out in my shocking lightning bolt heels by pumping his cock like a gas pedal, going pedal-to-the-metal on his cockhead and twisting my shoe on his frenulum. Once he humiliated himself by being unable to resist under my sexy heels I play a little bit with his cum on the trample board.

  • Cute sandals cock crush
    This is a long awaited clip for someone... I got these sweet flat sandals from a very devote Slave and I've been dying to try 'em on Step-Daddy's dick. I go from cute teasing his cock between my feet to cruel cock crushing under my heels. I slip his dick inside my shoe and that's when things get hard for Step-Daddy as he cannot resist me anymore and gives up in a surrendering cumshot under my sole.

  • Glam pumps heeljob
    Danger! High voltage! Today I'm gonna trample poor Step-Daddy's dick in my brand new lightning bolt heels! They make me feel so sexy, I'm sure Step-Daddy's cock won't last long under them. I love keeping him on the edge balancing my weight on his defenceless cockhead and eventually he will cum spurting all of his cum on the trample board. Oh, poor boy, you just can't resist me, don't you?

  • Bossy secretary Sissy ruins her coworker
    Bossy secretary Sissy puts his coworker back at his place by giving him a great shoejob. As she kicks his cock with her sexy shoes her pantyhose get all covered in precum but she keeps mocking his colleague's dick with her shoes. She pushes his cockhead down under her high heels and rubs his dick with her feet until he cannot resist anymore and that's when Sissy ultimately makes fun of him by stopping and letting him spurt all of his cum away in a great ruined orgasm. That's what he deserves.

  • Toes tease
    Caution! Fresh paint! I just put on the red nail polish... Let's see what Step-Daddy's dick thinks about it when I crush it under my sexy feet, twisting my toes on his cockhead, leading him to a huge cock dancing cumshot. So... What do you think?

  • Crushed and milked in red platforms
    I bet my red platforms are too much for Step-Daddy's cock so I won't be pleasing him too much today, I will be crushing his poor dick under my sexy shoes instead and see how much he can bear before cumming. Because I'm a sassy bitch I will be also denying him a couple of orgasms and ruining his long awaited one. Oh, did I win my bet? I guess so, you little loser...

  • Wedges shoejob footjob
    It's time to crush Step-Daddy's manhood in my lovely wedges! In this clip I drive him to cum trampling his dick, stomping, twisting my platform flip flops on his defenceless cockhead. As he's up to cum, I finish him with my feet, squishing it under my toes.

  • White Havaianas footjob shoejob
    I got these new white Havaianas as a gift from my #1 fan and to be sure they fit well I'm gonna test them on Step-Daddy's cock. I will start by sitting over him playing with his dick in my flip flops, from gentle teasing between my ankles to rough cockhead crushing under my soles, then I'm taking my flip flops off to tease his frenulum with my toes. But too much pleasure can be bad, so I stand up, get my flip flops back on and start crushing his dick again. When he's about to cum I'll finish him by pumping his sperm out under my bare feet. What do say, do they fit well?

  • Cheerleader's shoejob
    Do you like my new striped knee socks? I love them and I guess Step-Daddy's cock will enjoy them too. They get all dirtied in precum right away as I start teasing his cock with my sexy yellow pumps... I know how to keep him on the edge for a long time, twisting and kicking his cockhead in my heels until it blows off spurting sperm all over my brand new socks!

  • Black ballet flats vs cock
    The new cute ballet flats my Step-Daddy bought me have just arrived, now it's time to crush his manhood flat under them! I'm gonna start by gently teasing his dick between my shoes and once he's aroused I will crush the cum out of it by cruelly squeezing his cockhead under my heel and twisting my shoe on his frenulum.

  • Kicking your cum out in Red Heels
    I really love my 7-inch red plateau heels, they're so sexy, and today I'm gonna play with Step-Daddy's cock in them! I will drive him to orgasm by gently kicking his cockhead with the tip of my shoe, rubbing my feet all against his dick and kicking the sperm out of it, getting my feet and shoes all covered in cum!

  • Summer flip flops cock crush
    Sunscreen and beach towel packed and I'm ready to go to the pool! But before leaving I wanted to give Step-Daddy's cock some bittersweet pain under my flip flops and feet. I love having fun with his dick, sweet his cockhead, crushing it under my soles, squeezing it inside my thongs, seeing him suffer really turns me on. After a long cock crushing game it spits out all of his cum inside my flip flop, so I get it back on - it got all slippery! Now I'm ready to get some suntan.

  • Flower Power footjob
    Summer has finally come and there's no better way to celebrate than milking Step-Daddy's dick under my feet wearing those cute flower anklets I got from last week's party! I'm gonna tease his cockhead with my toes and crush it under my heel as his bittersweet pleasure leads him to a big cumshot.

  • Converse cock crush
    Today I'm going for a walk on Step-Daddy's dick in my white Converse Chucks. I go from soft and cute teasing to naughty cock crushing! I also have fun in edging his cock under my soles and then denying his orgasm so I can go on his cock again. After a long and tough time under my shoes I make him cum crushing his cockhead under my heel.

  • Teased and milked in heels
    I love showing off my legs and playing with Step-Daddy's cock under my high heels. After teasing his hard dick between my feet, I go a little harder on his cockhead, pumping, twisting, crushing it to a huge cumshot!

  • Double trouble ruined shoejob footjob in wedges
    It's so much fun teasing step-daddy's hard dick under my sexy wedges and, oops, stopping right before he's about to cum... After a long and intense cock crush, as I lift my sole his dick starts dancing and shooting cum all around! So I take my wedge off and I start crushing his cockhead again, now with my feet, until I ruin his orgasm twice.

  • Cum under Sassy Sissy Queen of Hearts' heels
    Off with your cockhead! Said the Queen of Hearts. Sassy Sissy's gonna crush your hard dick 'til you cum under her classy heels. This sure is wonderland!

  • Double ruined orgasm under my pretty heels
    Today I'm gonna tease Step-Daddy's dick in my super short shiny blue skirt, fishnets tights and my 5" yellow heels. Sure it won't take me long to make him cum, but as his dick gives up under my sexy heels I stop... Twice haha! I love so much when his dick dances and squirts cum all around as he suffers, so why not crushing his cockhead again right after he cum?

  • Secretary Sissy ruined footjob shoejob
    I feel so hot in my work outfit and I love teasing Step-Daddy's dick with my heels and under my feet as I love stopping right when I see he gave up to my sexy feet, ruining his long and long awaited orgasm. Oops...!

  • Kinky dancing footjob in micro skirt
    Time to party!!! After a couple of drinks I let the lights and the music take me to the podium. I feel so hot in my metallic blue micro skirt and I'm having such a great time dancing, we cannot say the same for Step-Daddy's dick, being trampled, crushed and twisted under my pretty feet.

  • Tattoo pantyhose footjob sockjob
    Today I'm gonna trample Step-Daddy's dick to cum in my tattoo print pantyhose. I love holding it between my pretty feet and crushing it under my soles and toes. I go from sweet slowly teasing his dick to naughty stomping on his cockhead, in a long edging orgasm denial game. Even after he did cum all over my pantyhose I go on playing with his cock a little more.

  • Fishnet sailorette footjob
    What do you prefer? When I squeeze your dick with my toes or when I crush it with my heel? You'll get both you lucky bastard! Don't cum early, I want to sweet you a little more...

  • Black plateau sandals cock trample
    Step-Daddy's been a bad boy today so crushing his cock head to cum under my heel is all he deserves. Unfortunately for him I'm wearing my plateau sandals so it's gonna be a hard time for his dick.

  • Red heels black socks shoejob
    I love heels and my red pumps always give a boost of sexiness whenever I wear them. So why not use them for a nice shoejob, especially when Step-Daddy's cock is luring for some bittersweet pain!

  • Housewife's wedges cock crush
    Housework is very long and hard, just like Step-Daddy's cock when I trample it to cum with my lovely platforms.

  • Edging barefeet cock crush
    I love squeezing Step-Daddy's dick between my feet and under my toes, watch me play with it until it's too much even for him. Poor boy!

  • Ready for the beach flip flops footjob shoejob
    Are you ready for summer?! Just to be sure, I wanted to try my flip flops on Step-Daddy's cock until it explodes.

  • Secretary pantyhose and black heels shoejob
    Working at the desk all day... At least I have Step-Daddy's dick to play with. The sexiest break from paperwork!

  • Classy fishnet and heels cock tease to cum
    I'm going to a party! Sure I'll miss Step-Daddy's cock under my shoes, I'd better not miss the chance of playing a little with it while I'm putting my makeup on... Oh, you did cum?

  • Yellow pumps shoejob
    Step-Daddy's dick gets crushed by my flashing yellow patent heels, I'm sure I'm gonna have fun playing with it under my soles until it explodes.

  • Red plateau heels cock trample
    No dick can stand my sexy red plateau heels, not even Step-Daddy's. After stomping and twisting my shoes on his cock head it squirts out all of his cum.



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