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Lily O'Riley - Search Results


  • Gloves & Boots & SQUIRTING

    Sometimes I just want to pack as many of my favorite kinks into one clip as possible, so I started out with my sheer black pantyhose, added my tall satin gloves and knee-high leather boots and finished it all off with a neat little collar and one of my njoy wands so that I could make a SQUIRTING mess for you. I tease you, running my hands over my soft breasts and sensitive pink nipples, then slide my dark hose down just enough to toy my needy pussy until I'm soaking the bed with a series of moaning orgasms. If you like fetish clothing, sexy stripping and watching me cum until I can't function, well, this is a very good clip for you.

  • Fishnet Countertop SQUIRTING

    Sweet, slutty Lily is all dressed up in her thigh-high fishnets and cute little collar with her little pink pussy on display. Watch her finger herself before sucking on a big black dildo and stuffing herself completely full. You can hear every sloppy noise as she fucks her wet pussy and you get a great eyeful of her fishnet wrapped toes and calves as she makes a mess SQUIRTING all over the counter. By the time she's done everything is a sloppy, soaked mess.

  • Sidetable SQUIRTING

    I'm so in love with my Bad Dragon devil this short little clip from my chubby girl days I climb up on my bedside table and indulge in a SQUIRTING orgasm before bed (featuring my bad dragon devil dildo and a slim vibrator).


    If you've seen my YT channel you know that I spend a lot of time playing with sexy things on screen. Sometimes all those big toys I touch get me so turned on I have to do something about it, so I climb up on my desk and take my one of the dildos I've been reviewing for a very NSFW ride. Features: fingering, dildo sucking, dildo fucking, SQUIRTING

  • Shy Girl Squirted

    Cute vintage Lily - back from her braces-wearing college days - is so awkwardly eager to show off for you. She exposes her her puffy pink nipples and shows off her gently hairy bush (and underarms) before climbing on the bed and toy-fucking herself to a SQUIRTING orgasm.

  • Self Bondage SQUIRTING

    I adore the tension and restraint of struggling against my ropes, so I take a moment to set up a simple frog tie (double column, thigh to ankle) and show off my cute little feet before settling in to fuck myself thoroughly and squirt all over the place


    When Lily's nearing shark week she starts to crave your dick, so all you need to do is watch as she lubes you up and begs you to fuck her in missionary. Soon enough your pale cock is spearing between the folds of her pretty pink pussy as she mooans and grinds up against you. She's super vocal as you fuck her to orgasm over and over again, eventually grabbing her little Doxy wand and sweet talking you until she repeatedly squirts all over herself. It's not enough to satisfy her, so next you get to watch as she forces your cock past her tight rosebud and cums one last super intense time with you buried in her ass. If you'd like something special, why not contact me for a custom?

  • Squirt Permission Seeking

    I know you love to hear me beg...and oh, nothing's sweeter than when you make me beg to squirt. I do my best to be a good girl here - telling you how delightful the toy feels and how badly I want it - while I fuck myself with one of my big Bad Dragon dicks. It's even sweeter at the end when I finally get to pull it out and make a mess everywhere

  • Sleipnir SQUIRTING

    A quiet day at home, my favorite bad dragon toy and an adorable little butt plug is just what I need to lose myself in an indulgent masturbation session I start by exposing my perky tits and playing with my puffy pink nipples until they're hard, then fingering my lightly hairy pussy until I'm soaking wet. When I can't take it anymore I slip my cute little plug in my ass and grab my girthy dildo for an orgasmic ride. Watch me pound my pussy until I squirt - giving you a front row seat to every pulsating contraction - and cum over and over until I can't take any more. You also get an amazing view of my wrinkled soles and sexy arches as my toes wiggle and spread with each orgasm.

  • 4K Post-Pumping Edging & SQUIRTING

    Picking up where UP CLOSE PUSSY PUMPING left off, Lily starts with showing you her incredibly puffy pink lips before lubing up her tight little asshole for a sexy glass plug in anticipation of an extended edging session. Watch as she slowly shoves the plug inside, moaning and describing the stretch as she goes. With the see-through toy filling her up Lily goes back to showing off her fat, wet labia before fucking her sensitive pussy with a metal g-spot toy that rubs her hot little cunt just right as it wiggles the plug inside her ass. She's too sensitive to edge herself while getting fucked like that, so she pulls out a doxy wand and feathers the vibrations on her clit while moaning and begging. Every time she gets close to cumming her well-pumped lips pulse and you can see the cream drip out of her needy cunt. As the minutes crawl past she gets more and more incoherent, begging so prettily for you to let her cum as she brings herself to the edge over and over again. When she's finally allowed to cum she grabs the metal toy and soaks the bed over and over again as she fucks her creamy pussy hard and deep until she physically can't take any more.

  • Toy Tryout: Self-Thrusting Dildo

    One of my most popular YouTube videos regards a self-thrusting dildo and I just happened to find a recording of my very first toy tryout with it! I start off giving it a very thorough blowjob to test the texture, then spread open my soft pink lips and let it deep inside. Once I've tried it out in the traditional way (rubbing my clit and thrusting it deep inside to make me squirt) I can't help but turn on the thrusting feature and give it the opportunity to bury itself cervix-deep in my pussy. I wind up in a neverending loop of orgasms until all I can do is rub my hard clit and let it fuck me until I can't help but squirt all over the bed.

  • Exactly What I Wanted

    I might be a holiday grump, but that doesn't stop me from gifting myself with exactly what I want for Christmas (mostly, lots and lots of SQUIRTING orgasms). I settle myself in front of the tree and give you a front-row view as I squirt into my panties and then repeatedly spray right into the camera as I cum over and over with my holiday-appropriate red dildo.

  • Submissive GFE

    I'm aware that work has kept you away - and I know that working hard to provide for us is important - but I miss all the kinky sex we have! I dress up in my cutest black lingerie and try to tempt you into coming home early in this little video message... I talk about all the things I miss about you and all the little things you do that make me feel so submissive to you before pulling out my collar and asking you to make me yours. Once the collar is on I can't help but break your no-masturbating rule as I play with my perky breasts and sensitive nipples. Things escalate quickly after that - nipple clamps go on, I spank my inner thighs until I'm grinding against the bed with desparate need and then paddle my pale ass until I can't help it and have to slide my fingers into my wetness. I end up begging you for your dick as I fuck myself to a SQUIRTING orgasm with one of my black dildos...won't you come home and put me in my place? If you love submissive redheads, fishnet thigh highs, sloppy SQUIRTING and being called need this video.

  • Snap Show: Pre-Date Masturbation

    First dates make me nervous and when I'm nervous I get all kinds of horny, so I settle in with my Doxy to take the edge off before I leave to meet my dinner date. One orgasm isn't enough to satisfy me, so I strip away my leggings and sloppily finger myself before grabbing a small dildo and fucking myself to a series of messy, SQUIRTING orgasms, all while showing off my sexy soles.

  • Secretary Clothes Destruction

    Secretary Lily can't help but get naughty on the desk, sliding her hands into her soft silk top and letting her skirt ride up to show off her pussy. She teases you with her tits, tugging on the fabric to try and get them free before finally giving in and ripping the dress open so that she can get to her sensitive nipples. Shredding the dress just got her even more turned on so she continues to tear it, getting wetter and wetter with each rip of the fabric. Soon her stockings are in danger as well, as she digs her manicured nails into the nylon just to watch it shred apart. Soon she's ripping her clothes with one hand and fingering her sweet pussy with the other, but by the time she's destroyed both thigh highs she needs something more and she uses her shiny patent heel to fuck her clit to a noisy, messy orgasm. If you love destroyed clothes, shoe fucking, sexy fingering secretaries and SQUIRTING , this is absolutely the clip for you.

  • Fuck Me on Campus

    Even smart girls need to get laid sometimes - I show off the cute little buttplug that I wear to class and then tell you about how I'd love you to fuck me in the lecture hall or over a desk or anywhere else that a little slut like me deserves it. All this talking gets me worked up enough that I just have to fuck myself with my pretty pink dildo and ends up with a delightful SQUIRTING orgasm all over my thighs.

  • Toy Tryout: Indra

    When I had the chance to try out a knotty dragon dildo from a local company I just couldn't say no, so that's how I wound up in front of all my Premium subscribers as I get myself all worked up in preparation to take the toy for a ride. After some intense nipple pinching play I can't help but pull out my cordless magic wand and cum a few times through my panties before impatiently stripping and showing off my soaked pink pussy and thick clit. Once I've cum again it's time to lube up the textured, veiny toy and ride it in cowgirl so that you get the perfect view of my big clit and the way my lips spread to take the girth as I struggle to fit the knot inside me. I turn into a mess as I desperately ride the knot and cum, letting you watch from the front and back as I squirt over and over again. feat. Indra the dragon from Fantasticocks *Discounted Due To Moderate Audio Glitches*

  • Toy Tryout: Fun Factory Bouncer

    Another toy tryout! I've been lusting after the Fun Factory Bouncer dildo ever since it showed up in my mailbox, so I couldn't help dressing up in some matching lingerie (mostly because my puffy pink nipples look so sexy when they're cupped by a balconette bra) and giving it a very thorough trial run. I start with a little nipple play to get myself nice and wet, then fuck myself with the thick, ridged toy in a variety of positions as I explore all the ways it makes me squirt. You get to watch up close as it slides inside and makes me cum with my wrinkled soles on full display.

  • Snap Show: Slime Play

    I love playing with slime - feeling it ooze along the curve of my breasts and pool sticky and slick between my thighs - so I fill up a carafe with the slimy pink stuff and pour it all over, coating everything from my hair to my toes. By the end I'm incredibly wet and messy, completely slippery and so turned on that I can't help but grab an uberrime dildo and fuck myself to some intensely SQUIRTING orgasms while showing off my sexy soles.

  • Speculum Masturbation

    In an attempt to recalibrate my feelings around speculums I've decided to do a little erotic exploration with a metal one I recently acquired, so I start out by slowly racheting my pussy open with its metal screw (and the clicking as it presses my walls apart is disturbingly sexy). Once I'm held wide open I bring the camera close so you can watch my walls pulse as I contract around the device. Once the preliminaries are out of the way it's time to get adventurous, sliding my metal toy inside to grind against my g-spot until I can't help but cum around the invading appliance (and with how it holds me open you can see everything). I'm aching to be filled up, so I drive a sleek dildo deep inside and hold my doxy wand against my clit until I squirt everywhere.