Videos Tagged with Silly

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

Charlotte Stokely - Sissy Competition 1 thru 4

Sun 19 Jul 2026 05:10:26 +0200

Relax and watch all four sequels without clicking... I've made them into one long video for enhanced brain damage, haha! Sissy Competition Part 1 My best friend is boasting that her husband is the faggiest sissy in town and she’s gonna enter her into the Towns Miss Sissy competition. I just know she’ll win coz she wins everything , and her sissy really is a proper over the top mincing faggot. Sissy Competition Part 2 Good morning princess ! Oh my - u **** for so long. You’ve missed your morning chores and haven’t massaged my feet yet today. Don’t look so anxious sweetie - it’s ok. I fully understand. You had such a busy night last night coming out of the sissy closet. Sissy Competition 3 I’ve uploaded that video so stop even worrying now. Thank me hunny. Go on. Say “thank you so much mistwess Charlotte for outing me to every single one of my followers and friends on social media”. And say it like you mean it you silly little pansy. Hahahahahahaha Sissy Competition 4 Oh, here comes miss 2nd place sissy pansy? You fucking retard. How dare you lose the sissy competition! I expected first place after I made you blow so many of the judges! I have a bunch of humiliating punishments for you!

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.

i fuck myself silly while waiting for game to come back

Tue 17 Feb 2026 00:33:16 +0200

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