Category: Cuckolding

  • Cuck Driver Gets Punished (episode 3 season 1 of Cuckold Cruelty)

    Cuck Driver Gets Punished (episode 3 season 1 of Cuckold Cruelty)

    Do you want some ice for your wrist? Hahahaha. Cuz my pussy is so sore from that pounding I took while you waited in the car. Did you mind serving as my loser driver for my booty call while you were ordered to stroke and thank me nonstop? What is the reward you deserve? Should I just drip his cum all over your face and hair or should I make you lick it directly out of my pussy? You just earned yourself a night in the small closet… not the big one… the small cubby hole under the stairs! I want you covered in dried cum as your back starts to ache and you wish you could straighten your legs! Oh and your gonna give me another three hours of “thank yous”!

    Duration: 10 min | Price: $10.99

    Starring: Penelope

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  • The Full Fuckover (Entire Season 1)

    The Full Fuckover (Entire Season 1)

    This is all 8 episodes of "The Full Fuckover" season 1. Experience all the episodes back to back as one long series (1 hour and 20 minutes) without having to click a button. Save over $20 compared to buying each episode independently. Includes: Financial Control. The Full Fuckover (season 1 episode 1) Fag Fuckover. The Full Fuckover (season 1 episode 2) Cum Eating Fuckover. The Full Fuckover (season 1 episode 3) Door Dick Cuckold. The Full Fuckover (season 1 episode 4) Primp And Pimp. The Full Fuckover (season 1 episode 5) Blackmail Fuckover. The Full Fuckover (season 1 episode 6) Public Humiliation Fuckover. The Full Fuckover (season 1 episode 7) Chastity Asswipe Fuckover 8. The Full Fuckover (season 1 episode 8)

    Duration: 80 min | Price: $59.99

    Starring: Adriana Chechik Tip Adriana Chechik Directly

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  • Closet Cuck In Panties (episode 5 season 1 of Cuckold Cruelty)

    Closet Cuck In Panties (episode 5 season 1 of Cuckold Cruelty)

    How exciting for you cuckie… you get to watch me and a real man fuck tonight! I know I've told you about how me and your boss laugh at you behind your back… especially while we're fucking… but now you'll be able to hear it for yourself! Isn't that hot! You're gonna be so pissed off at this that it's gonna take every ounce of strength to not cry. You're gonna be in that closet wearing pink panties and lipstick. I mean you could burst out of that closet and try and claim to be a man and claim that you deserve to be treated like a big boy but it's not gonna mean anything with you looking like that, hahahaha.

    Duration: 9 min | Price: $9.99

    Starring: Penelope

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  • Ruined And Trapped (episode 4 season 1 of Cuckold Cruelty)

    Ruined And Trapped (episode 4 season 1 of Cuckold Cruelty)

    You do realize the only reason you’re allowed to stay in this house is cuz you give me your fuckin paycheck, right??? Right??? Yea, that’s right cuckie… oh and by the way, every time I rub that in your face is the right time to thank me for giving you food to eat. So what the fuck are you waitin’ for? Get on your knees and stroke that that fuckin tiny dick. I know that your food is covered in cum half the time. You’re lucky it’s not all the time! If anyone at the office that hasn't seen the videos I already posted of you, are gonna see them now. In fact, I’ll have your boss make you prepare a fuckin slideshow of your cuck status! Congratulations… you’re a Fucking disgrace!

    Duration: 7 min | Price: $7.99

    Starring: Penelope

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  • Stomped Stupider (episode 6 season 1 of Cuckold Cruelty)

    Stomped Stupider (episode 6 season 1 of Cuckold Cruelty)

    Oh, I’m sorry… did you expect a hand job??? Cuz losers get shoe jobs, hahahaha. Awe, I see my cruelty and laughter is already getting your tiny faggot cock nice and hard. Each time I say “Fuck You” is an extra day that your gonna spend over my lovers place polishing his shoes. You’ll beg him to become his shoe cleaning house servant! I expect you to be Kneeling by the door to greet him.

    Duration: 9 min | Price: $9.99

    Starring: Penelope

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  • Cruel Chastity Cleaning (episode 8 season 1 of Cuckold Cruelty)

    Cruel Chastity Cleaning (episode 8 season 1 of Cuckold Cruelty)

    The only time I let you out is to clean it. And of course by clean it I mean I pour girly shampoo on it and step on your cock and balls with my high heels. Tell me, fag, have I turned you into a little shoe freak yet??? I mean the only contact your inferior cock ever seems to get is when I'm stepping on it in my sexy high heels, hahahaha. Does that mean this is now sex for you? Now that your hands are cuffed behind your back and you're out of that teeny tiny chastity cage… your gonna flop that little fag cock of yours on the stool and prepare for your cock stomping… I mean cleaning, hahahaha.

    Duration: 8 min | Price: $8.99

    Starring: Penelope

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  • Chastity And Laughter (episode 7 season 1 of Cuckold Cruelty)

    Chastity And Laughter (episode 7 season 1 of Cuckold Cruelty)

    You’re in luck cuck. I’ve actually thought of a new reason to laugh at you. And I know that you can’t get hard unless I’m laughing at you. I’m gonna take away your tiny penis! Hahahaha. Yup, it’s true! I mean I’m not chopping it off… yet… but for now a steel chastity cage will make me laugh at you just fine. See these chastity cages come is smaller and smaller sizes. So I’m gonna keep reducing the size as the months and years go on. You’re not only gonna lose your ability to get hard, but your gonna have a one inch micro penis! Hahahaha. Awe, don’t cry, fag. So now it’s time to put it on you… oh that’s the spike strip… yes hand it to me, that goes on the inside. Yes it’s gonna hurt, stupid, hand it to me.

    Duration: 9 min | Price: $10.99

    Starring: Penelope

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  • The Office Of Extinction (episode 1) The B1 Beta Program

    The Office Of Extinction (episode 1) The B1 Beta Program

    You're in a female led society… captured and find yourself in a chair at the government "Office of Extinction". The place where inferior males are sent to be castrated or "disposed of". Suddenly the sexy office girl turns around and reveals that it's your ex-girlfriend! Yes, She works there at the beta seed disposal division! You've been paying her bills and funding her travels for a year and have depleted your savings… and then you finally got the guts to take your pants off in front of her. Too bad you were a "full inch under" the state penis size minimum and she turned you into the "Office of Extinction". What will she recommend for you… Castration??? Penectomy??? Disposal??? She phones the Governess and they devise a humiliating plan. They give you a government "B1 Beta Visa" which means you will be put you in a spiked chastity cage and be humiliated on State Propaganda TV. You don't know what's in store for you but you will be completely sissified and made into a household name. Your degradation will be used to strike fear into the minds of any wimps the are still in hiding and get them to turn themselves in for processing.

    Duration: 14 min | Price: $9.99

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  • Cuckold Cruelty by Penelope (Entire Season 02)

    Cuckold Cruelty by Penelope (Entire Season 02)

    The wait is over. Binge Watch Season 2. Over 82 Minutes of cuckold humiliation for only 59.99. Plus you get to see all the episodes before they are available independently. EP1- Detained And Drenched EP2- Beg For Your Banded Balls EP3- Tied Tattooed And Pierced EP4- A Thanking For A Spanking EP5- Cuckold Snipped Smooth EP6- Clowned And Kicked EP7- Your Boys Are Goin Out With A Bang Ep8- Serving Cuckold Scraps EP1- Detained And Drenched Experience the journey of helping your new girlfriend out at her stripper job while I entertain some bachelorettes as a sexy cop… I need a volunteer to arrest and you must fill in! Someone's gotta suck off the hunks. EP2- Beg For Your Banded Balls Being your new girlfriend, I feel insecure about telling you my deepest sexual fantasy so I want to tie you up first so you don't run away… Then I proceeds to gag you and put some very tight rubber bands around your balls. I admits that I think it's really hot if your balls suffered permanent damage while I was in the next room fucking a hot guy. EP3- Tied Tattooed And Pierced Happy Birthday! As your new girlfriend, I went snooping through your computer to find the perfect gift for you. And it seems you don't even have any straight porn on there… It's all humiliation, chastity and female superiority stuff. Oh well, that's why your waking up to find out I had a chastity cage pierced onto you… oh and the hot tattoo girl added a few more things that she thought would be funny. EP4- A Thanking For A Spanking You were experiencing a moment of weakness when you asked to be released from chastity and well.. It's times like this that I have to be strong for the both of us. I graciously allow you to grovel at my feet and thank me after the beatings. EP5- Cuckold Snipped Smooth I could get thousands if you donated a testicle or two. Luckily I have a hot nurse friend that thinks it's super funny to snip off beta balls. Oh and my new boy toy is coming over and would like some of that cash too. Make sure you kneel at the door and offer him your cock and balls, ok wimp? EP6- Clowned And Kicked Your invited the the party… as the humiliated entertainment. I'm gonna dress you up as sissified nut kickin clown. You'll stand right there and all your allowed to say is "please kick me in the balls", haha. Oh and lift your frilly shirt and curtsy while you say it so your balls are exposed for all those kicks to the nuts you're gonna get.. EP7- Your Boys Are Goin Out With A Bang A gang bang to be specific, haha! I invited my new boy toy to come over here with a bunch of guys to pond youir asshole while they snip your nuts off for good! Me and my hot friends wanna masturbate to you begging to turn fag for our entertainment. Ep8- Serving Cuckold Scraps Now that your nuts are gone and you just work around the house for me and my NEW boyfriend… I give you your only meal for the day served up with suspense and humiliation. You never know if I'm gonna just dump your food on the floor… or step on some of it… or grind all of it into oblivion and make you lick my heels clean. It's chow time! Goddess Penelope

    Duration: 82 min | Price: $59.99

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  • Cuckold Cruelty (Season 2 episode 2) Beg For Your Banded Balls

    Cuckold Cruelty (Season 2 episode 2) Beg For Your Banded Balls

    Being your new girlfriend, I feel insecure about telling you my deepest sexual fantasy so I want to tie you up first so you don't run away… Then I proceed to penis gag you and put some very tight rubber bands around your balls. I admit that I think it's really hot if your balls suffered permanent damage while I was in the next room fucking a hot guy. Goddess Penelope

    Duration: 9 min | Price: $9.99

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