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They/them. "Chicago's Own Community Chest". Dominant muse, burlesque, findom, modeling, porn, art, and more!


@cruelvalentinefree Latest Posts

  • I’ve been even more into breast play than usual lately. What’s your latest fixation?

  • Where’d all this come from? Unlock to trace it back to the source. <br /><br />Soft. Warm. Wet. Slick. <br /><br />This pussy is where you belong. <br /><br />Send me some fun money for Vegas so I can be extra slutty? 😜💦

  • 3 bucks gets you the full drop. Or you can just torment yourself with this preview gif, if you prefer. 😘

  • Feeling devilish under this red light in my bedroom. Do I look the part? Would you let me put that mouth of yours to work on my luscious tits? Tip and let me know. 😉

  • I find these blue lights super calming. Relax with me for a bit?

  • A little treat for the cleavage lovers… 😘😘😘

  • We’re long overdue for some fun, aren’t we?

    Check out this fun little self play video here for $7, OR, head over to my subscription page, OnlyFans.com/CruelValentine, and get access to my entire library of nearly 3k pieces of slutty, smutty media for only $7 A MONTH!

    P.S. Special cameo by the big ol’ rope marks on the backs of my thighs, courtesy of my new office chair. 🤪

  • Happy holidays, lovers!

  • This week, I created this alternate cut of my decadent vibe masturbation video from last year, "Heart Eyes for Hitachi". I think it's a far more potent and mesmerizing edit. What do you think? Unlock to see what all the fuss is about! 😻

  • Enjoy this super slutty shower strip with a twist! Good things usually come in threes, don't they? 😉

  • Front or back? Tip an odd dollar amount for front or an even dollar amount for back. 😇💕🍑

  • What’s your favorite thing about spring?

  • If you’re not one of my recurring subscribers on my paid page @cruelvalentine, you missed out on my cute St. Patrick’s Day photo set and that sucks! Treat yourself! Unlock it here or subscribe to my paid and I’ll send it to you today!

  • Interested in seeing more, more, more of me? Why PPV here again and again when you can have a feed full of all the smut with no additional paywall? 2,268+ images, videos, and gifs are waiting for you, plus new posts coming all the time!

    Also, I’m running a little extra special sale right now, so your first month is only $3! That’s 80% off!

    Come hang out with me and see what you’ve been missing!

  • These Obsession brand leggings are everything and I need them in every color. Tip to contribute to My leggings fund to keep my ass perfectly accentuated like this always. 😍

  • Begging someone to finish this law school paperwork for Me like...

  • When I think about you, I.... 😏

    It’s been a stressful week and I just had to finally release all the pent up energy and frustration that it brought. Unlock to watch me absolutely melt as I show off for you, flicking my clit, fingering my juicy pussy, and playing with my tits. I moan and urge you to be a good slut for me and to come here to do your part, as I work myself into a wet, hot orgasm. 😍🥵💦

  • A little behind the scenes action from My show with SanctuaryTheClub.com tonight! Wet and messy acts require a lot of cleanup. There was slime everywhere! 🤪

    This was a fantastic way to spend My birthday! I love performing so much. You should join Me next time. And don’t worry, belated birthday tips still count!

    Tip if you think I should post the full act video! (To those of you who were there, my phone footage has much more vibrant colors in the black light than My webcam did. You can see every little drip...

  • Happy birthday to Me! Unlock for a little POV action of me straddling you, towering over you as I grind and tease you with My full breasts.

    Also, swipe over for info on where to find Me and shower Me with affection tonight! Join Me at Sanctuary? 😍🎊💸

    How else would you like to help Me celebrate?

  • Booty lovers, swipe over for a treat!

    Tip if you’d like a front row seat underneath me while I’m doing squats. 😏

  • Unlock this cute photoset to see Me spreading and playing on My living room floor. Cozy up by the fake fireplace with Me? 🤪

    My birthday is coming up on March 11th! What are you getting Me? Tip below and visit My wishlist in My bio to help Me celebrate! Anyone who shows Me some birthday love in the form of a $50+ tip and/or a wishlist gift will get a special, personalized thank you video! 🥰

  • One minute in heaven. 😇 😉

    My tits are super swollen and tender right now, and aching to be loved on. I’m feeling generous tonight and thought I might show them off for you with a little bit of jiggling, bouncing, and caressing for good measure. Lucky you!

  • This is what I look like in Zoom meetings. Just saying. 😏

  • Good afternoon, beauties. Now say it back.

    Tits + adorable cardigans are the cutest combo, aren’t they? It’s cold as Hoth here and I cold use a cuddle buddy.

  • Happy Cruel Valentine’s Day, My dears. I took some pretty photos for you after My show last night, so I couldn’t let the holiday pass without sharing them. I especially hope you adore the spread shots as much as I enjoyed taking them!

    Thank you for being the angels that you are. I appreciate each and every one of you!

  • Here’s the second half of this radioactive set from Tuesday! Scroll on over for My beautiful kitty. 😸😼

    Let Me know how it makes you feel, yes?

  • What’s your favorite way to worship Me? I love teasing you in these sheer black panties. How does it feel to have My sweet warmth just a breath away?

    The eerie green lighting in this set feels tempting and dangerous. Intoxicating, even. What do you think?

    Second half of this set coming tomorrow! 🤩

  • Some may think I'm greedy, but really, I just know what I want and go for it. Watch me play with two of My favorite vibes and cum over and over again in bed. I definitely wore Myself out that day. It was well worth it, though, believe Me.

  • Join Me for a quick shower? I just got some new mint shower gel that smells amazing, so I wanted to share my excitement with you. Can you feel the steam? 💦

  • Anyone who knows anything about Me knows that I have a huge financial kink. There are many ways to please Me, but the quickest path to My heart truly is through My bank account. Financial domination is a majorly misunderstood kink, but it's definitely something that riles Me the fuck up in a very real way and gets Me wetter than anything. I love the absorption of power that comes along with it. The redistribution of wealth not only gets Me off, but it also helps to move us all toward a more equitable world, one bit at a time. Many birds, one stone. 🥰

    Anyway! This is from a shoot based on one of My signature burlesque acts, "A Meditation on Money". I had so much fun frolicking around downtown Chicago in the Financial District with TKM Photography bringing these images to life. Tip for a treat!

  • Railings and scaffolds are some of My favorite playthings onstage.

  • Who here enjoys erotic audio? Lay back, close your eyes, and enjoy an aural masturbation session with Me. Some chit chat, My infectious giggles, and vivid descriptions as I bring Myself to bliss for 27 minutes. What more could you ask for?

    Please note that this is a video formatted file, but this is an audio only clip. Just let My voice wash over you.

  • I love how gorgeous lingerie feels. The only thing that feels better is taking it off. Swing by My other page for lots of nudes and other fun! http://OnlyFans.com/CruelValentineFree

  • Simona Signoret really knows how to capture My best side. I adore the way these luxurious ostrich feather fans feel as they brush across the most sensitive parts of My skin. It's impossible not to smile when experiencing that sensation. What textures and sensations drive you wild?

  • God, I love the curves of My body so much.

  • Here's a fun Dominant strip I did for Sanctuary a few weeks back! Careful, it may sting a bit... 😏

  • A shot from My "Mirror, Mirror" photoshoot and full-length video, shot by The Lust Garden.

  • Take a peek at My private champagne room performance from Sanctuary Virtual Strip Club last month! A lucky patron got to have a nice, close up look while I danced sensually, stripping nude and playing with Myself for 24 minutes. I'm so happy I left My phone camera recording so I could share the fun with you! There's something so overwhelming and sensual about performing for someone so intimately. Don't you agree?

  • A gorgeous shot by Erik Michael Kommer from Kink It! in Chicago.

  • I love combing through old performance photos. I miss live burlesque shows so much! What would you give for a private dance with Me?

  • I love this shot by Amanda Tea so much. She's one of my favorite collaborators. I think I look quite regal at this angle. Wouldn't you love to be worshipping at My feet and gazing adoringly up at Me?



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