Videos Tagged with Silly

Cruel Girlfriend - Panty-Blocked By Your Bratty Ex-Girl

Fri 18 Sep 2026 01:37:11 +0200

Does she even know about your embarrassing fetishes? Like don't even pretend to not know what I'm talking about loser - I heard all about the date you have tonight and if you think for one second I'm gonna let you off the hook and trick another girl into dating you - you are totally fucking mistaken! I bet you haven't told her you're a secret submissive, right? You've pretended to be a real-man haven't you? The truth is, just like I found out and dumped you, so will she eventually so why even try Mr Humili-Porn Creamer? And now that I know all about you, I'm making it my new hobby to destroy all your chances with other girls because submissive little pansies like you deserve to be panty-blocked. I'll fuck up your dates and cut-off your relationships with girls before they even begin... starting with little Miss Unaware tonight. So, loser, if you don't want your bratty ex-girlfriend to call her up and tell her all about your fetish for being bossed around and bullied by snarky popular girls, then you have to agree to wear these emasculation panties on your date with her tonight. Uh-huh loser - I'm PANTY-BLOCKING you - which means as long as your laughable little pee-pee is tucked inside your sissy-panties, you won't be getting it out in front of her will you? Not unless you want your fantasy of being totally fucking humiliated to come true! I mean it's one thing jerking off to humili-porn in front of your screen like a fist-creaming little pig, and quite another being exposed as a panty-wearing sissy for real! So if you don't want me to call her right now and tell her you're an actual sissy - wear the fucking panties!And that's not it panty-boy. I want you to wear a butt-plug on your date too. Under your panty-blocker panties and buried deep inside your ass - she'll never suspect a thing sissy! She might not be able to see it but you certainly won't be able to ignore it loser. That panty-encased plug will remind you all night long that you're not good enough for your date. You'll fidget and wriggle on that big ass-stretching plug as you try not to leak a pathetic sissygasm into your panties... now that really would be embarrassing wouldn't it? Can you imagine being sat with your date as that big plug hits your little sissy g-spot and you get that silly look on your face and org-spasm right in front of her! She'd probably think you've made cummy-panties just by looking at her! Haha! So what's it gonna be you little dweeb - do you want me to ruin your date or are you gonna wear your panties and plug

Cruel Girlfriend - So You're My Boyfriends Bitch Right

Sun 16 Aug 2026 04:24:20 +0200

So you're the wimp my boyfriend turned into his bitch huh? You're the pansy he blackmailed into become his sissy. How humiliating! He said you're not even gay - is that true?.. That after he caught you in panties you didn't have any choice - that the photos he took were so embarrassing that you just had to keep doing even more humiliating things... which gave him even more to blackmail you with until here you are... answering to me - his hot, bitchy girlfriend who's about to make your nightmare even fucking worse! Rule number 1, sissy... don't get caught! You failed and now you're my boyfriend's bitch - dressed up like a girl - keeping his place clean and tidy while we live our best lives.He told me everything he does to you - I should feel sorry for you but I don't - it's your own fault. He told me he makes you suck his cock twice a day. Haha! That's so funny - sucking his cock because you have no fucking choice! And all the chores he makes you do in that silly little maid's uniform. Dusting and cleaning and scrubbing all day long while he thinks up even mores to keep you in check. Even more embarrassing things to make you do - even crueller ways of controlling you. He knew you've always had such a crush on me - which is why he asked me to be his girlfriend... and then... he showed me the photos of what he did to you. Photos of you getting used by his friends - dancing for them - sucking their cocks - getting pushed around and bullied by his real-man buddies. You looked so fucking pathetic - I'm so grateful he asked me to be his girlfriend and not you!It doesn't seem fair to me that my boyfriend and his buddies have had all the fun with you... So guess what's coming next for you sissy?... I'll give you a clue - it's 10in long, made of silicone and I wear it like a harness around my waist while you suck my boyfriend's cock... Yuh-huh sissy - you're gonna get spit-roasted by me and my real man - when he gets home you're gonna give him his second blow-job of the day while I'm filling your ass full of strap-on cock. I wanna see what all the fuss is about - I want to fuck you in the ass and turn my boyfriend's bitch into MY bitch. We're gonna humiliate you together from now on - starting with an emasculating roasting - him balls-deep in your mouth and me balls deep in your ass!

Kendall Olsen - Commit To Sissification

Fri 07 Aug 2026 05:00:05 +0200

I don't want you to be a real man. There's no fun in that. I'd much rather you be more like... a fun gay toy for me to play with. A silly little bitch for me to train. That sounds more fun, doesn't it? I love the idea of training you to suck cock and take a dick up the ass so well, that I can actually use you as a Rent-A-Hoe. A set of lips and an ass for real men to fuck and use for their own pleasures. That's where my pleasure comes in- watching you get used like a common sissy slut

Kendall Olsen - Pay My Rent

Tue 04 Aug 2026 07:29:47 +0200

You know what really stresses me out? Spending my own money. It makes me anxious to see money coming out of my account. I don’t want to feel anxiety. Stress causes wrinkles, and I don’t want my gorgeous face to wrinkle. You don’t want that either! You love my perfect good looks. I should never lose my own money to silly things like living expenses. That’s your responsibility! You need to ensure my comfort and spoiled lifestyle by covering my rent every month. That money should always be coming out of your bank account, and never mine. My numbers should always climb, while yours dwindle with your sacrifices and generosity to Goddess Kendall. Pretty girls should never feel obligated to pay their own rent. I have loyal slaves like you to take care of that for me. <3

Kitzis Clown Fetish - Lonely Virgin

Thu 16 Jul 2026 04:58:23 +0200

Silly, stupid little virgin! You are always going to be a dummy stroker for Kitzi. Always shoving that unfucked cock into your first, squeezing and stroking, always wishing it was a pussy instead of a lonely loser hand. Your dick doesn't deserve a woman's warm wet hole. Tug yourself until you chafe. Pump for Clowns because this is the ONLY sex life a reject like you can manage!

Kitzis Clown Fetish - Lick It Up Dummy

Thu 16 Jul 2026 04:09:25 +0200

You are so obsessed with pleasing Ringmistress that you'll do anything for me. Anything to please me. Even if it's... icky... and... sticky... anything to be deemed my good boy. Your silly little brain goes staticky at the prospect of putting a smile on my pretty Clown face. Which is great, because I want to watch your THROAT get staticky and sticky tonight! You will swallow your load for me tonight with a big Clownesque smile of your own!

Kitzis Clown Fetish - Clowns Make You Swallow

Wed 08 Jul 2026 07:05:19 +0200

You are a slime sucking dummy! You are so obsessed with pleasing Ringmistress that you'll do anything for me. Anything to please me. Even if it's... icky... and... sticky... anything to be deemed my good boy. Your silly little brain goes staticky at the prospect of putting a smile on my pretty Clown face. Which is great, because I want to watch your THROAT get staticky and sticky tonight! You will swallow your load for me tonight with a big Clownesque smile of your own!

Kendall Olsen - Bicurious Trigger Training

Wed 08 Jul 2026 06:16:28 +0200

I hear it all the time from boys just like you. You're not gay, you're not a perverted little faggot, you're simply bi. Maybe even bicurious, sure. I've heard it all a million times, and you delusional cocksuckers never fool me. You're only fooling yourself. I know you're not some silly kinkster tolerating my imposed bi clips because I'm a hot bratty blonde. You are totally and completely addicted to big dick. I know it. You can deny it, but I know how hot you get when I make you jerk off to giant cocks. You're boiling over with penis envy and the absolute at being instructed to stroke to such hot studs.

Kitzis Clown Fetish - Big Top Homewrecking

Fri 19 Jun 2026 20:21:16 +0200

It's all worth it! Risking your marriage for me, sabotaging it stroke by stroke, is such FUN. Every pump into your fist reminds you of what a bad husband you are. How delicious! Don't bother feeling guilty. Ringmistress has such a confusing hold over you- it's not like you could RESIST me. You HAVE to indulge in me. I'm just so hot and weird. I'm exciting. I'm new. I'm all the color and fun your current life (and marriage!) lacks. You NEED to pump your silly-willy dick for me.

Princess Ellie Idol - Service My Servers Tonight

Tue 16 Jun 2026 13:53:32 +0200

What makes you think you can be a good slave for Ellie Idol? After you briefly explain, Ellie commands you to strip naked so she can assign you to your position. Will you be a video sub, a sex slave, or something else entirely? You were doing so well until this part of the interview... You're terrified of her seeing your small pecker but not wanting to miss your chance to be her slave, you drop your trousers. Oof. Well, Ellie still has a position for you even though you're severely lacking in the peen department. She's going to have you serve at her party tonight. No, not food or beverages, that's for the bulls to serve-- along with their MEAT of course!! You'll serve her bulls, silly. Soon you will be servicing Ellie's servers tonight for the entertainment of her guests!! Big dicks get pleasure from the little ones and all Ellie's short dicked men will be there at the party sucking off those well hung bulls. Big cocks get to cum, little cocks get to leak and twitch! Tonight cocks will be in your hands and spunk will be on your tongue!! Bring those men to orgasmic bliss, subby pet!! Do your best, even if it's your first time. You must give it your all... IF you want to be Ellie's slave of course. Are you ready and willing to put on your best performance?

Kitzis Clown Fetish - Bankrupt Paypig

Tue 09 Jun 2026 12:17:40 +0200

I won't be happy until you are completely broke. Until I have taken every last penny from you, I won't be satisfied. I don't want a silly little tribute here and there. I'm aiming to drive you into BANKRUPTCY for the CIRCUS. I like the idea of financial submission actually hurting you. It shouldn't just be a fun tribute every now and again, something silly to indulge in. I want it to hurt. I want it to have lasting effects on your psyche and your body. You will be exhausted. You and your bank account will be at my mercy. It's more fun for me to treat my human wallet sadistically. I am going to destroy you as I drain drain DRAIN you of everything you have

Spreading My Thick Thighs & Fucking Myself Silly on Cam

Mon 23 Feb 2026 18:51:25 +0200

I reach for my favorite toy, that thick, veined dildo that's seen me through so many lonely nights, its silicone surface cool against my palm before I warm it up by rubbing it along my inner thighs, letting the chat hear my breathy moans as I build the tension.