Penny has signed Sam up for some special "personal training" with mixed wrestling badass, Mia Li. In this case personal training just means pain and sexual humiliation!  The wrenching holds and brutal pins would be bad enough but Mia isn't satisfied with their session until she strips Sam naked, makes him slap himself in the balls, and has him crying for Penny to save him. Fat chance!

Penelope Reed has been making out with you all night at the Halloween party. Once she finally gets you alone, Penelope even does a sexy little dance just to get you nice and hard for the best blowjob of your life. Then she sees your dick and realizes she has been tricked.At first she barely believes how small you are but then she gets pretty annoyed at losing out on her plans to gag on big cock and get fucked all night. She does take your tiny boner in her mouth and bounces her cute round ass on it but just to rub in your inadequacy. The whole time Penelope is making fun of you, she never actually stops playing with your little dick. Despite her giggles and your total humiliation, it is not long before her teasing fingers cause you to embarrass yourself in a whole new way.

Carmen Valentina is in town for her bestie's wedding but the weekend gets off to a rough start when the bride's little step-bro gets too big for his britches. Sam thinks that Carmen will be into him now that he has made a little money, even though she used to give him wedgies and tease all the time. Carmen laughs right in his face when he goes for a kiss and quickly puts the horny and delusional Sam back in his rightful place. Dancing on his tippy toes and begging for mercy with his undies up his butt! She torments him with painful wedgies while rubbing his face in all the most embarrassing memories the two of them share. Carmen wants to make sure he does not forget that he is still just a silly little wedgie boy so she strips Sam out of his CK boxers and puts him in some tighty-whities from his old bedroom. Sam went from hitting on Carmen to begging her not to make him take more wedgies in schoolboy underpants before she even unpacked from her flight.

Sequel to Ella Nova's Premature Ejaculating Pet Ella Nova loves having you as her little pet wanker who does whatever he is told for the privilege of jerking off to your her while she laughs in your face. After her recent efforts to make you publicly cum in your pants were only semi-successful, Ella has a new idea to spice up your unconventional relationship. Putting you in her panties! She wants you wearing girly undies under your pants at all times from now on. You will still get to play with yourself in her presence, you will just be pantied during your stroke sessions. If you are a very good boy Ella might even give you a pair of her dirty panties to sniff when she makes you wank.    

After watching Game of Thrones before bed, Sam's dreams take a odd and kinky turn. He imagines himself in his own bedroom but fighting for the honor of his queen. Too bad he is still a wuss, even in dreamland. He tries so hard but his female opponent is way too powerful. She squeezes the strength right out of him with a series of scissorholds between her thick thighs before spanking his little butt and making him eat her pussy. Sam can't even fantasize about a wrestling match that does not end in humiliating defeat.

Don't forget this clip is only available for one week! Penny and Sam are friends but they are also rival internet streamers who are always trying to make each other payoff embarrassing bets in front of their viewers. Usually, the punishment is something mild like singing a silly song or wearing a weird costume in a video but then one of Penny's subscribers suggested she give Sam a wedgie. Penny gets so into giving out the wedgies that she rips poor Sam's little undies. Once his underwear is destroyed, Sam can't hide that for some reason he has gotten a boner from having his underpanties yanked up his butt. Penny thinks it is hilarious that she gave Sam a wedgie and hard-on in the same livestream. She is also definitely not going to pass up a chance to increase Sam's humiliation and her follower count. Penny has a great idea to use the busted briefs and Sam's little stiffy to accomplish both of those goals.

Robin's Naked Halloween Sam thought matching Robin Halloween costumes sounded like a really cute idea until it turned out that instead of Girl Robin & Boy Robin it would be more like Girl Robin & Naked Robin! By the time he realizes most of his outfit is missing from the package, Penny is already dressed and ready to leave for the party. She has no time to listen to him whine so she strips him naked and makes him wear what is left of the costume. Sam begs her not take him out in just a cape and his underwear but Penny is secretly quite eager to make him show off his tiny bulge to the whole party so she insists he looks fine. When Sam still hesitates Penny decides a little pre-party ass worship is just the attitude adjuster he needs. Of course, sticking his little face under her skirt changes Sam's tiny bulge into an embarrassing boner for Penny to show to the whole party instead! Velma Solves Mystery of the Tiny Boner The best part of Halloween is the costumes but it just isn't the same without a delicious treat to put in your mouth. Since she is already wearing a sweet Velma outfit, Penny decides decides to drag the boy dressed as Shaggy away from the big party to see what kind of candy he has for her. Unfortunately for Velma, Shaggy is only packing a pixie stick in his pants! Jinkies what a teeny winkie! As soon as she pulls the fun sized stiffy out of his underpants, Velma starts laughing and reaches for her magnifying glass to maximize his embarrassment. She may think his dick is a hilarious trick instead of a treat but she still wants to get off before Halloween is over. Velma tells Shaggy to get his silly face under her orange skirt and start licking or she will run downstairs to tell Fred and Daphne about his small cock faster then he can say Zoinks! Cowardly Shaggy lets her sit on his face and obediently worships her ass and pussy even though Velma does not stop humiliating his boner the whole time she is grinding on his tongue!

Ever since Ella Nova pantsed you at a public pool she has basically controlled your life and totally owned your tiny cock. Ella is finally going to allow you to wear boxers again and all you had to do to get her stop making you wear her dirty panties was give her your super nice apartment. You will still be paying the expensive rent but at least Ella won't be pulling the lacy waist band of your thong to show random neighbors anymore. Ella starts to strip down to give your weekly wank time but she keeps getting distracted by all the sweet memories of humiliating you the last few months. No matter what she has done or said to you, Ella still just needs to wiggle her butt and giggle to make your itty bitty boner start aching for her to give you the cum countdown.