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Dr. Barber understands that you claim to be suffering from an overactive libido but that is definitely no excuse for the rude comments you made toward her. The good doctor does have some very special medicine that might just solve your perverted little problem though. She actually thinks you might need a double dose to decrease the size of your... libido.
The med does not take long to start working and Dr. Barber invites you to show her the results. Actually she orders you to whip out your dick and then bursts into laughter, both at your pathetically diminished dick and the look of shock on your face. You made her angry with your sexually inappropriate language so she made your cock so tiny it's now inappropriate for sex. It might become too small even for wanking by the time her serum makes its way through your system. There is no telling how long your minuscule member will take to grow back to its normal size but it should be enough time for you to learn your lesson. Dr. Barber is willing to help you jerk off before your dick shrinks any further but only if you can get off to a naked woman laughing at your tiny penis.
Penny is very surprised when Sam shows up for her hot tub party since guys with small dicks usually avoid skinny dipping. Sam did not realize it was a no clothes allowed event so Penny explains that his little penis is going to be a huge embarrassment. To prove her point Penny suddenly yanks his pants down to his ankles to show that he blushes just from getting pantsed in front of one person. Penny knows shyness is not the only reason he should avoid a pool full of naked women-Sam will definitely pop a little beta boner as soon as the bikini's come off. He would probably spooge in the water if a girl bent over in front of him and Penny tells him so right to his face!
As a final demonstration of his total lack of cock control Penny strips naked herself and starts to tease him to show how easily he gets excited. She proves her point a little too well though when Sam completely humiliates himself almost instantly!
Penny is in desperate need of a last minute stripper replacement for her friend's bachelorette party and the only guy she could get on short notice was her scrawny friend Sam. He definitely does not like the idea but Penny begs and bribes him to at least consider it. She still has to strip Sam herself to get him naked so he can try on the stripper briefs. After she finally gets his undies off him though, Penny realizes that she has made a teeny tiny little mistake. Sam has an absurdly and pathetically small cock!
Being a team player at work sometimes means submitting to tasks that are outside of your normal job description. When Sam volunteered to play mascot at a business conference, he knew he would have to wear a sailor's uniform but he did not realize it was a humiliatingly juvenile sailor suit! Too bad his supervisor, Adriana, does not care one little bit about his dignity.
When Sam refuses to put on the embarrassing costume, she just yanks away his towel and jams the ridiculous garment onto her helpless co-worker. Adriana stifles his protests by sitting her big, round ass right on his face. Twerking on the weak whiner is pretty amusing to her but she wants to make sure he will be completely obedient before they head to the conference. Adriana knows a spanking session over her knee will get Sam to fall in line. The only thing more embarrassing than dressing up like a sailor boy is having to do it with a bright red butt peeking out of his little outfit.
Principal Barber feels really bad that you have been sitting naked in her office for so long after what those mean girls did to you but the school has not found any clothes for you yet. She feels a little less guilty when she finds out exactly what you did to deserve being ganged up on by four girls in the first place. Principal Barber is so offended, she even decides to add to the humiliating graffiti that the bullies left all over your body.
Instead of a stiff punishment, she wants to let the girls off with an apology as long as they promise not to tell anyone all the embarrassing things they did to you. They also have to promise to keep your small dick a secret. You won't get justice but you at least get to keep your pathetic reputation from getting even worse. Principal Barber is not going to give you clothes before the girls come to give their very sincere apologies but she will at least help you get rid of your silly little boner before they arrive.
Magical Stripping and Small Penis Humiliation from Zatanna
When Justice League magician Zatanna catches you in her dressing room she decides to teach you a magical lesson in the importance of privacy. First she freezes you so you can't move or even speak, and then she zaps off your clothes one item at a time. Zatanna is not satisfied with stripping you and making fun of the tiny boner that you popped despite your fear. She wants to cast a charm on your little cock that will make it just as humiliating as it is exciting when she starts to tease you with her big tits and round ass. Zatanna is going to make sure you are hard, helpless, and covered in shame before she kicks you out of her dressing room.
Ella Nova was so excited to get you back to her apartment after your amazing date together She was planning to consummate the flirting that you two had been doing all night. Then she sees that you had good reason to take her to such a nice restaurant. You have the smallest cock she has ever seen! Ella might feel a tiny bit bad for laughing after she unzips you but not bad enough to suck your tiny cock.
Ella is a very sweet girl so she decides to take pity and offer to indulge in some mutual masturbation with you. Ella does not want to send you home with a little stiffy and tiny blue balls. She flashes her perky little tits and wiggles her nice round ass in your face. Eventually her giggles subside as she actually gets a little turned on herself. There is something pretty hot about making a guy so hard and so embarrassed at the same time. You should feel lucky that the date still might end with you both cumming in her bedroom.
Two short spanking punishments in one. In the first part, a thief is chased down then stripped down on the streets of San Francisco. This public humiliation scene is presented silent film style with captions. The second spanking features the gorgeous Kat Soles, who feels that her submissive boytoy wasn't properly appreciating her perfect ass so she turns his bright red.
Charging porn to your hotel room on a business trip is pretty dumb but jerking off to that porn while your co-worker is only ten feet away is next level stupid. Adriana is sharing a suite with Sam during their work conference when she walks in on him, dick in his hand and adult pay per view on the TV. She is furious at his unprofessionalism but also amused at his embarrassment. Instead of retreating to let Sam cover his body and recover some dignity, Adriana grabs his exposed cock and berates him for daring to play with the tiny thing in HER room.
Making fun of him for being a pervy wanker with a little dick is pretty fun but Adriana wants to make more of an impact on Sam than just verbal teasing. An immature decision deserves an immature punishment so she puts the naked boy over her knee for a spanking that is just as painful as it is humiliating. Adriana does not stop after she turns his butt bright red though, she just makes him stand up for a round of spankings on a much smaller target.
Bored and horny MILF, Penny Barber, has decided to make the cute (in a geeky sorta way) neighbor boy her new plaything. Penny asks him over to her place to help with some computer troubles but she has him unzipped and throbbing before long. Everything is going according to plan until her new boytoy proves he is more "boy" than "toy" by cumming all over himself almost instantly!
Of course he is completely humiliated by his little accident but Penny is more amused than annoyed. She does laugh in his face at his total lack of cock control but she is still going to use him to get off. It will just have to be his little mouth instead of his pathetically quick squirting dick! While she is making him lick her pussy Penny makes sure to maximize his embarrassment by commenting on "his cute little erection" and how he lasted "less than two minutes". Before she cums on his face Penny explains that to improve his disappointing dick she will be putting him on a strict wanking schedule!
Penny never imagined that her submissive boyfriend, Sam, would ever dare get his little cock near another woman behind her back. So when Penny finds a brand new pair of panties in Sam's drawer that are not in her size she is furious. Sam tries to sputter out an excuse that they were for her but Penny does not listen long before grabbing him by the hair and burying his face in her pantied butt. She tells him that she doesn't believe such a dedicated little ass worshiper like Sam would ever forget what size panties she wore. Either Sam is cheating or... the panties are for him! No matter which is true Penny will not be satisfied until Sam is feminized, totally humiliated, and squealing about how much he "likes to wear girl panties"!
Starting nasty rumors about your co-worker, Mona, seemed like the perfect way to edge her out for a promotion until she brought in your ex-girlfriend Mia. The two girls seem to have really bonded over the prospect of humiliating you and they even mockingly act out some of your more embarrassing bedroom failures. They plan to make sure the entire office knows about your unimpressive package and sexual inadequacies...unless you remove yourself from the running for that promotion. If you ever want to be able to show your face at work again then you better realize there is going to be a lot of ass kissing in your future.. starting right now.
Never lie about the size of your cock and definitely don't pretend your pea shooter is a magnum if you are planning to hook up with Penny Barber. She might just tie you to the bed, turn on her webcam, and show the world the pathetic truth! After Penny's dating app booty call shows up with way less than the promised seven inches she makes up for the disappointment by documenting the humiliating tease session she is going to put him through. Penny belittles his dick while rubbing off on him like he was a dormroom body pillow. Even a tiny-cocked twink can provide useful friction if you just cover his whole body in babyoil! Once he is panty-gagged, slick with lube&juices, and utterly degraded Penny starts to actually fuck him just so she can laugh in his face about barely feeling his itty bitty boner!
Penny has two little subbie boys to entertain herself with today, Sam Solo and YOU! Penny makes you both strip for some cock mockery and humiliating jerk off instruction. Once she has you naked she orders both betaboys to get hard so she can bust out the ruler- first to measure your exact smallness then as a CBT paddle to punish you both for being so little. Penny may not want much use for such inconsequential cocks but at least she does find your itty bitty stiffies hilarious!
Penny Barber and Mia Lee have been hired to give a celebrity nude photo scammer a humiliating taste of his own medicine. They are not just going to strip him naked for a few embarrassing pictures. The two women overpower him before slowly removing his clothes to make sure he knows he is completely helpless. They play with his cock to get it hard just so they can make fun of his below average boner. Mia and Penny take turns snapping selfies while they spank, wedgie, and even punish his little balls with his own belt!
Once they get him completely naked Penny puts him over her knee for a double hand spanking but they reserve an extra special humiliating group photo for the big finish!
Every mobster loves money but Penelope Barber, aka Lucky Penny, also loves to torment the unlucky losers who end up in her debt. When degenerate gambler Sammy Solo shows up a grand short on his pay off for her, Penny is more excited about punishing him than she is mad about the missing cash.
She makes him stand with his pants down while she counts his payment and then offers him a real devil’s bargain to erase some of his debt. Penny will credit him a hundred bucks for every inch of dick he has above the average but he owes two hundred per inch if he is below. This little challenge is just Pennys first step towards making sure Sammy’s account stay deep in the red and his little nose stays deep in her ass.
Wedgies And Spankings For Submissive Stud Alrik Angel
Penny is excited for a day of lounging by the pool with her submissive hunk, Alrik, rubbing sunscreen on her legs and showing off his muscles in the speedo she bought him. The only problem is her sweet eye candy forgot his wrapper and left the new speedo at home. Penny is not pleased and she takes her frustrations out on Alrik's bubble butt
After plenty of begging and spankings she sends him down to buy a new swimsuit from the hotel gift shop with undies wedged up his very red bottom!When he returns from from the hotel gift shop with some ugly, baggy swim trunks as a replacement Penny right back over her knee for another spanking!. She got him a speedo so she could admire his cute bulge and bubble butt in the hot tub and Penny gets what Penny wants. If she can't ogle him by the pool then she is going to strip him naked and take her time groping him before they leave.
Of course this leaves Alrik with a very noticeable boner tenting up his shorts but Penny has no intention of letting it go down anytime soon. If he does not want everyone to see his stiffy that is just too bad because Penny is going to spend sometime with her ass on his face and his cock in her hand before she drags him to the hot tub!
Poor little Sam has been getting bullied so bad at school that he has to beg smoking hot MILF, Penny, for protection from her mean step-s. Penny is very upset that her boy has been picking on this cute wuss so she decides to have a some fun while teaching her little bully a lesson. Penny straddles the nervous nerd and starts stripping him to his undies but it is obvious Sam is definitely not equipped to handle a sexually powerful woman like her. She still has some fun playing with him and even making fun of him a little herself. Sam just tries to hang on as Penny pins him down and rubs off on him like a schoolgirl humping her favorite pillow! When Penny realizes Sam can't take much more before he is going to squirt into his shorts she calls up her bullying step-s to tell him Sam is in her bed! Now Sam can pretend he fucked his bully's step-m even though she really just used him as a sex toy...
Penny Barber was not very happy when she found out the school recommended her as a tutor for you. Then she got a great idea to have some fun with the awkward dork that was being put under her power. Penny is going to be wearing her absolutely sluttiest little cosplay outfit and you will be spending the entire study session naked. Since you are here to bring up your science grades then Penny plans to start with a biology question. Can a male specimen with a tiny penis ejaculate without physical stimulation if he is being visually teased by a female specimen with an amazing ass and huge tits?
Nika Venom is a professional man ruiner and her latest target is a businessman with a terrible attitude and a tiny cock. His own secretary has hired Nika to obtain humiliating pictures of his ridiculous little dick. Nika has no problem seducing, stripping, and tying him down for his career destroying photoshoot. She even smashes her amazing round ass in his face to make sure he is nice and hard widdle dick pic. The only question is what will Nika do with him once the job is done and she just has a jerk with an itty boner at her mercy?
Now that her co-worker, Ella, tricked their boss into giving up some amazingly embarrassing material to use against him, Kat knows he will do whatever she says on their business trip. She is supposed to be assisting him during their work conference but she is taking his big hotel suite and teasing his cock to her heart's content. Kat finally gets a chance to put her boss to some use now that he is in chastity. Ella has made sure his cock stays locked and that the key gets passed around the office to any woman who wants a crack at him. The moment they get up to the room, Kat teases him with her beautiful, round ass until he is willing to pay her any price for the key. She even wiggles her big butt right on top of his little plastic prison until the loser coughs up five figures for five minutes of freedom for his little dick.
You have been so thoroughly demoted from boss to office slave that your secretary loans you out as a pantied maid on the weekends. Penny Barber is going to let you out of chastity if your cleaning job is good enough. You might regret the few minutes of freedom for your tiny cock once Penny is done teasing it, though. You will get to feel her soft tits and round ass on your cock but only to get your balls a brighter shade of blue.
Penny has been helping her best pal get a girlfriend with shopping tips and dating advice. She already took him out to buy some new underwear and get some hot undie photos for his online dating profile. That was when she found out about his small dick. The next step in her plan is to help him learn how to deal with girl's reactions when they unzip his pants and only half a cock comes out. Penny starts making her friend come up with new ways to say he has a tiny penis and secretly loving it as he gets more and more embarrassed.
Then the real humiliation begins when "roleplay" different hook up scenarios that mostly consist of Penny laughing at his boner and then either storming out or demanding he lick her asshole. He is quite surprised to find out Penny is serious about that part when she grabs him by the hair and puts his face between her cheeks! Penny finally ends their little learning session with the most degrading orgasm of his life!
Penny Barber has been "helping" her shy little friend, Sam, create an online dating profile so he can get a girlfriend. After a day of shopping to improve his wardrobe Penny insists she needs to take some pictures of him in his new clothes to put on his dating profile. Starting with modeling the skimpy underwear she made him buy! Penny does not take "No" for an answer and soon Sam is standing in front of her in tiny briefs trying to hide his little bulge with his hands. Penny takes pictures like she promised but she also gropes and teases him until he gets an embarrassing tent in his new undies. Penny does not hesitate to reach into his briefs and pull out his little stiffy for further inspection. Just when Sam thinks it could not be a more humiliating day, Penny starts lecturing him for not telling her sooner that he had a small dick. It is going to make the job of finding him dates much harder. She explains that with a cock like his he had better have other skills... right before she pushes his head under her skirt!
Penny had tried to help her buddy Sam get a date while also having a lot fun teasing and embarrassing him about the reason he can't get a girl in the first place. His cock is just so little! Penny can't help making fun of him, even though she does really want Sam to find a girlfriend.
She has finally set him up on a blind date with a cute girl who already knows his boner is itty bitty! Penny is helping him get ready when the girl texts to say she wants to see pictures of his undersized unit before the date. Must have had some second thoughts about willingly accepting a puny penis. Penny is definitely not going to waste this final opportunity to humiliate an extra small stiffy! Will he even make it out to the date or will it be another night of pussy sniffs and pity wanks?
Face Sitting and Small Dick Reminder from Daisy Ducati
Sam has majorly screwed up by forgetting to pick up the male top for a cuckolding scene. Daisy decides Sam needs a little reminder to why he is not qualified to play the part of stud. Since boys always learn better with butts in their face, Daisy perches her yoga pants covered ass right on Sam before beginning the lesson on his inadequacy. She peels down his little PJ pants and boxers while she explains that they need a cock that looks like it can fuck a women and his little thing is only good for "locking up in a pretty pink cage". Daisy cracks herself up at the idea that they could find a cuck with a dick small enough for Sam to be the stud.
After the humiliating lecture Daisy makes Sam promise not to mess up like this again but his punishment is not over until Daisy makes full use of the chastised little submissive under her butt.
Penny is not really surprised when she catches her roommate, Sam, with his face buried in a handful of her panties. She thought he looked like a panty sniffer from the start but she liked living with someone who let her run the house so Penny gave him a shot. Now that she has caught him in this embarrassing position, he will just be even more under her thumb and she will get to have some fun humiliating him for being a panty perv.
Sam is too scared to really argue when Penny gives him a panty mask and starts to strip him. She is delighted to find Sam is already wearing lacey undies and that he has a dick that definitely belongs in girl panties. Her roommate is going to be too humiliated to ever talk back to for the rest of his life. Now Penny just has to decide how to get the most enjoyment out of her new pet pantyboy.
Penny Barber has started quite a few humiliating initiations and hazing traditions on campus but her favorite is making every boy from the new class come to her room to get his dick measured. Are you ready to drop your pants and submit to the ruler? Penny and her assistant Ella Nova have a feeling you would make a great candidate for "Little Man On Campus".Now that you have been living the total humiliation of being named "Little Man On Campus" Penny calls in her friends Siouxsie and Star to help decide if you need to be punished for your weak efforts at pleasing them. How can they embarrass you more than the entire university laughing at your tiny dick?
Bringing home a guy from a dating site is usually not the best to bet for great sex but Penny Barber has a secret trick to increase her odds of a good lay. If Penny does not like what she feels when she reaches into a man's pants then she just turns around and reaches under bed for the strap-on. Not so she can peg him and do all the work but for him to wear so she gets the dicking she deserves. All the verbal humiliation of explaining to him that he really does need to put it on to have any chance of getting her off is like its own kind of foreplay. The sight of his hilarious little boner sticking uselessly in the air paired with the full feeling of a nice fat cock sliding in is also pretty fun.
Penny sometimes still likes to play with their little toy cocks whiles she rides the full size one. A little teasing to go with the constant mockery is about all they get though. The closest their tiny dicklets will get get to her pussy is sucking the strap-on dildo when Penny needs a dick break.
Late Night Beatdown and Ballbusting with Cheyenne Jewel
Sam is keeping Cheyenne from her beauty rest with his late night workout but he blows her off when she asks him to cut it out. Big mistake. She decides to teach the insolent little pipsqueak a lesson, starting with a pantsing. She get him down to his little white jock-strap before really amping up the bullying with some stomach punches and knees to the balls. She even makes him worship her superior biceps. In the end she leaves him bruised, humiliated and begging for his clothes.
Amarna thought she had a moment to herself for a little private girl time with her vibrator but turns out there was a pervy little dweeb watching her vibe her pussy to orgasm! Amarna is furious at first but starts to laugh once she realizes that the peeper is very embarrassed and very, very scared of her. Amarna makes him lie on the ground so he can see how it feels to have some watch you vibe off. She pins him down and grinds her vibrator into his crotch while the boy whimpers and squirms underneath her. Between a naked cutie sitting on his chest and the buzzing toy on his cock it is not long before the horny little loser has a humiliating accident right in his pants! Amarna thinks it is hysterical how fast he made that embarrassing little wet spot but she has plans to make sure jizzing his jeans is not the end of the humiliation.
They say running from your problems just makes them worse and that is definitely true when your problem is a bully named Penny Barber. Tired of being tormented by the hottest and meanest girl in school, you decide to play sick and avoid the humiliation for just one day. Huge mistake. Penny shows up at your house and demands to know why you were not at school to entertain her with your pleas for mercy and blushing cheeks.
You wanted to avoid the sting of stolen lunch money but now Penny is helping herself to your step-mom’s purse.
You wanted to avoid the embarrassment of a pantsing but now Penny is making you strip completely naked in front of her.
You wanted to avoid the pain of a wedgie going up your butt but now Penny is tightening the harness of her strap-on cock.
You wanted to avoid being owned by Penny for just one day but now she is in your home, ordering you to play with your tiny dick for her amusement.
Penny knows you were staring at her butt during her entire workout but lucky for you, she was amused not offended. Teasing your feeble little erection is the perfect cool down after an afternoon of intense exercise. She is happy to let play with yourself while you drool over ass as long as you let her humiliate you the whole time. You will be wearing her sweaty shorts over your face while you sniff her perfect ass, and hump her gym towel. Penny knows she can do and say whatever she wants to you because little dick boys will take almost infinite embarrassment for the privilege of having a big dominant butt in their face.
If you really wanted to keep your most embarrassing secret from your girlfriend's mean roommate, Penny, you probably should not have let her borrow your laptop. You do kind of owe her since you are always hanging around their house but you should have guessed that Penny is the type of her girl to check your browsing history for stuff to tease you about. When you ask for your laptop back she just starts reading some of your recent searches aloud in between giggles Everything from "penis growth possible?" to "hot girls laughing at small dick".
Now Penny knows that your cock is little and that you have a humiliation fetish. She jokes that she is going to start making fun of your girlfriend for having a small dick boyfriend if you don't let her see it for herself. Penny flashes her tits and ass at you to make it more fair but she really is just doing it to make your itty bitty boner twitch. Then she realizes that saying mean and embarrassing things about your dick is what makes it twitch the most. Penny is not going to stop teasing your tiny cock until she finds your humiliation limit.
Ella Nova tried to give you a chance, she really did. She hoped your premature ejaculation would get better with practice. She thought maybe your small dick would be balanced out by great pussy eating talent. All Ella got for her patience was more disappointment. Now, all you are getting from her is some pretty pink panties to put on and a new role as her obedient little butt boy.
Butt boys worship ass all day and take strap-on cock all night. Get used to it.
When Bella and Penny catch their friend Sam jerking himself off they don't just giggle and look away so he can cover his shame. The girls actually demand that he finish playing with his cock right in front of them. When the humiliated wanker tries to resist they just grab his hands and make him stroke himself. Sam keeps ruining their fun by whining and begging for privacy so Bella and Penny decides he deserves a wicked case of blue balls instead of a chance to show off his dick in front of two hotties. They tie his hands behind his back and rub their tits and asses in his face until poor little Sam wishes he had just given them their embarrassing masturbation show.
Some boys need to learn to keep their mouths shut unless they want them filled with strap-on cock. Sam made a bet with Penny that he could "easily" do fifty squats but the little wuss falls over after forty-nine. His penalty is giving her a strap-on blowjob but of course Penny doesn't stop at a little imposed cocksucking. She makes sure to embarrass the little weakling as much as possible, mocking his manhood in every sense of the word. She even takes out his timid little stiffy and holds it next to her big, thick strap-on dick before sitting on his face to make him apologize to her ass for bragging. Penny pins him down and rides his face to an orgasm to finish their "training session".
PART I
Silly little Sam thought he might get through his punishment of cleaning Penny's house naked without too much torment and humiliation. Penny notices right away that he has walked in with an attitude. An over the knee spanking, along with some ballbusting to make his timid little boner go down, help Penny get Sam in the proper submissive mind set.
Part II
Poor little Sam still has not worked off his debt to Penny Barber so he is in for another humiliating day of naked house cleaning. After warming up her mean girl muscles with some mockery and teasing Penny makes Sam lick her ass while she finishes his chore list.
Part III
Sam has finally finished his nude servitude to Penny Barber. Penny might miss having a little maid boy around to humiliate but she won't pass up one more chance to tease him. She is going to give him his little reward while he does one last chore... shining her ass with his tongue!
Penny Barber likes to enjoy a little sun on her skin so she sometimes walks around her balcony in just a bra and thong. Unfortunately her twerpy little neighbor, Sam, enjoys her tanning time as well. She has caught him peeping one too many times and this time she is going to punish him herself! She grabs him by the balls and threatens to tell his step-mommy what a little pervert he really is if he doesn't do exactly what Penny says.
Sam is soon over her knee with his pants down counting spanks. Penny starts out letting him keep his undies and just using her hand but that is only the warm-up. She lets him up just to make him remove the rest of his clothes so she can discipline (and mock!) his little cock. Penny wants to make sure he is at least ten times more humiliated than she was by his peeping. She will not stop until he is stripped totally naked with his skinny red butt in the air taking her belt where anyone could see!
Penny Barber's style as a personal trainer is more like personal tormentor and she loves every minute of it. Her workouts will leave you just as embarrassed as you are exhausted. For Sam she has planned a fitness strategy of ballbusting and cock teasing! First, she makes him slip on pink boxing gloves to see if he can dodge her face slaps. After getting in plenty of good smacks Penny pulls down Sam's shorts so she can laugh at him struggling to pull them up with the boxing gloves on. Next, she makes him strip down to just a cup so she can "test his toughness" by kicking him in the balls over and over! For the final exercise in humiliation she puts him on a balance board and then teases his cock to see how long he can last without losing control... of his balance or his little dick!
Stripped Naked And Humiliated For Peeking On Penny Barber
Penny is getting ready to head out to a costume party when she notices a friend has been watching her change into her kitty costume. Jay claims it was an accident but Penny isn't going to let the little dork get a free peek at her bare ass and tits without some severe consequences. She puts Jay onto his hands and knees so she can spank him while she squeezes his head between her thighs. Jay keeps making excuses and begging for mercy but Penny does not let up until she has the peeping perv stripped completely naked with his timid little cock and balls at her mercy. After she is satisfied with the amount of ball smacks he has taken and the number of apology ass kisses she has received Penny decides to let the broken boy go free. Just soon as he agrees that his costume for the rest of the night will be Naked Loser!
Penny thinks it is hilarious that her step-bro's geeky little friend, Sam, has tried to change his look to all black and leather now that he is at college. When Sam comes over Penny decides to show him he still just a loser who can't protect his lunch money or pants from her. She easily throws him down and pins him underneath her for a nice bullying warm-up of wet willies, face spitting, and nipple torment. Sam is too weak to stop Penny from taking his wallet and too scared to argue when she makes him say that he is not a man yet. Once Penny gets bored of teasing she turns attention to taking down Sammy's pants for the REAL humiliation.
Sam need rest after he staye up all night playing video games at his college buddy, Jay's house. Sam had been warned not to come around any more by Jay's step-sister and roommate, Penny. When Penny finds Sam snoring on her living room floor with morning wood hilariously tenting up his little undies she decides he must need an even more humiliating reminder to stay away. First, she sits above his face and gives him a nice hard smack between the legs to get Sam's morning started by having his cries of pain muffled by her ass in just a thong! Once she has his attention Penny straddles the terrified Sam while she explains that he has screwed up big time by showing his face here again. The only place she will tolerate his face his under her butt and that is right where she puts it!
After he is pinned by her ass Penny easily snatches his boxers and takes turns punishing and then teasing his little morning boner right to the edge until she has him almost as eager to cum as he is to escape her clutches. She then gives Sam a choice between an orgasm with an extremely humiliation consequence or blue balls with just a mildly humiliating one. Either way she makes sure this his last sleepover at her house... unless she needs a butt boy for a seat cushion again.
Penny's little boytoy interrupts her rest by begging for attention with worshipful ass kisses. He should know better than to bother her without permission but she decides she actually is in the mood to use his mouth... after humiliating him for his impertinence. Maybe being stripped, spanked and made to put on a panty fashion show for his Mistress will help him remember his place.
Penny Barber likes to rent her spare room to young male tenants for a little extra money and occasionally a little entertainment. One of her lodgers decided to entertain himself one day and tries to sneak a quick wank in her room. Penny walks in and catches him completely naked with cock in hand on her bed. Of course, Penny takes great delight in spanking, scolding, and teasing the naughty young man for playing with himself in her room but she also wants to take advantage of the sudden appearance of a nude boy in her bed.
Penny does not see any need to let a stiff cock go to waste so she pins him down to take herself for a little ride. The dirty little wanker is an even bigger disappointment than she thought though because it only takes a few seconds of the curvy MILF bouncing on him before he humiliates himself. The annoyed but amused Penny has no intention of giving up her plan to use this little perv for her own pleasure. She is still going to cum but now it is going to be much more degrading for the little jerkoff boy!
Erection Endurance and Handjob Squats are just a few of the drills Penny Barber plans to inflict on her favorite twink to torment, Sam. She makes him try to keep his dick stiff while she pummels him all over with pink boxing gloves before testing how well he eats pussy under stress. Penny provides the stress by punishing his little balls!
For his final challenge, Penny wants to see how far she can push him before he is too exhausted to achieve his reward orgasm!
Penny Barber likes to rent out her pink and girlie spare room to little pretty boys willing to do anything for free rent. She has strict rules for the young men living in her house, including no clothes allowed, no talking back, and she can use any part of their body whenever she wants. Penny has a new boytoy moving in and he is pretty embarrassed to discover he will be living in a pink princess bedroom and even more so after Penny strips him naked! After Penny explains his new life of humiliation and sexual servitude she collects her first rent payment... in the form of ass kisses and pussy worship!
Professor Barber does not know why you are taking so long to finish your term paper since you are going to fail anyway. You are one of the worst students she ever had and she is not afraid to let you know. You grumble under your breath that Professor Barber can "suck my dick" and she openly wishes for a chance to kick you in the balls. This mutual loathing leads to a nasty little bet between the two of you. If you can write a decent paper Professor Barber will actually suck your cock but if not, then you will be the one with a mouthful of cum PLUS she gets to kick you in the balls.
Looks like your obsession with asses has finally got you in real trouble. The whole school has seen the video of you getting stripped naked in the girl's locker room and getting kicked in the balls by every person you tried to spy on. Your best friend Penny at least wants to make sure you are ok but she actually spend most of the conversation scolding you for being a creep and making jokes about the size of your dick/love of butts.
Penny does want to make sure your undersized cock and thoroughly busted balls still work though so she is willing to give you that glimpse of her bare ass you've longed for since forever.
MILF next door isn’t just the hottest woman on the block, she is probably the hottest woman you know. When you saw the tiny new bikini she was wearing in her backyard you followed your boner toward a huge mistake. Now you are getting an up closer look at her amazing but only because she made you show her your dick after she caught you masturbating in her backyard. Instead of calling the cops or her husband, Penny makes you keep jerking-off while she makes fun of you.
She teases you with her tits while instructing you exactly how she to touch yourself. Whenever you get close she tells you to stop and she demands you agree to mow her lawn if you want permission to finish. Penny also knows you are classmates with her step-d and she jokes about telling her all about your little backyard walking adventure. She was annoyed at having her sunbathing interrupted but Penny is actually thrilled to control the cock of a little loser boy that got caught with his pants down.
What do you get when you combine a desperate sub with an undersized erection and a basket full of Mistress panties? The answer is hilarity, if you ask Penny Barber. Her boytoy, Sam, is so eager for his special day when he gets permission to wank (or even a pity hand job if he is lucky) but Penny has decided today is for playing with panties and teasing (not pleasing) little cocks. Penny lets Sam know that she will give him one stroke for each pair of panties that she can slip over his tiny boner.
They both know Sam is way too small to serve as an effective panty holding peg but that just makes it way more fun for her (and humiliating for him) to try.
It is always exciting and terrifying when Penny decides to give you permission to wank. The terror comes from knowing she likes to make your orgasms as humiliating as possible. She is always pushing the limits of how much you are willing to embarrass yourself for a chance to cum. When she starts wiggling her bare ass in your face you can't miss the shiny plug twinkling between her cheeks. Penny can't stop giggling as she explains what she wants you to do with her butt plug. You are super desperate for a jerk session but Penny might have pushed you too far this time. Sure, she has sat on your face and made you lick her ass plenty of times before but even tiny dick beta boys have SOME dignity. Or do they?
Nobody likes being the butt of a big joke at a party but it is part of being friends. Getting pantsed at a pool party by one friend and then having another one yell out, “Woah, look at his little dick.” in front of everyone might be a bit beyond normal teasing. Pouting about your public embarrassment is not a great way to shift the conversation away from your tiny penis though.
When Penny comes to find you and apologize for her “little dick” scream that made everyone laugh, you totally act like a whiny brat about the whole thing. Even when she shows you her tits as payback/ bribe to cheer up, you still want to sulk and wallow in your humiliation. Penny wanted going to give you a chance to reclaim your dignity but now she is annoyed. The punishment for being a little dick boy with a bad attitude is going to be a lot worse than a pantsing.
Spankings and Chastity Teases with Riley Reyes and Ella Nova
Spankings and ChastitRiley Reyes keeps her submissive boyfriend on a pretty tight leash. Sometimes literally. Take a sneak peek into a household where female domination is the rule, whether it is bare bottom spankings for using his phone too much or making him stand naked in chastity while she has brunch with friends.
It is not all discipline and humiliation for Riley's boytoy, though. Sometimes, she and her hot friends tease his cock mercilessly too! Two beautiful, naked women grinding on his chest while his cock is all locked up is just another day in the life of a subby hubby.y Teases with Riley Reyes and Ella Nova
