Daisy Jacobs

You've told Step-mommy before, you don't ever want to move away or have Step-mommy stop taking care of you... so she's figured out how to make you her best boy forever! She pulls out a surprise strapon and you excitedly take every inch in your tight little asshole for you! She gives you lots of Good Boy praises too!

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You catch your StepMom getting changed and decide to watch-- much to her chagrin! She's horrified at first and tries to cover herself up before scolding you and telling you to go away, look away, go to your room, anything! You perv, why do you even want to see your StepMom naked anyway??

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You catch your StepMommy in the middle of her workout routine and she asks you to watch her do squats so you see if her form is right. After a while she decides you're probably not getting the full view of her form from all angles, so she asks you to lay down between her legs so you can see the angle of her legs. But... she's still not sure you can really get a good view like that, so she strips down entirely and does naked squats over your face. How do you think her form looked?

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StepMommy got a call from your principal saying you were acting out. She's had it, she doesn't know what to do with you anymore. Spanking doesn't seem to work on you anymore. So she decides to spank your dick and balls, first with her hands, but then she decides you seem to be liking it a bit too much, so she breaks out the wooden spoon!

Please note this video does go heavy on scolding talk, and it is very much a punishment roleplay, not a funishment roleplay. Non-nude, but I'm wearing a tight crop top and no bra, so my tits are very visible through the shirt.

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Step-mommy caught you peeking in on her while she was showering earlier, you perv! Now it's time for your punishment. Step-mommy decides to lock you in a chastity cage until she feels like you've learned your lesson! She owns your cock now. [This video shows lots of cleavage but is non-nude].

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Are you ready for StepMommy to change your diaper? You made such a mess! I'll just clean your penis up before we put the new one on. Won't that feel better?

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THIS IS MEANT TO BE AN ADD-ON TO MY MOMTOBER SERIES. This video only includes the edging tasks! It does not include any of the videos that it's meant to accompany, but they can be found in my store throughout the month of October 2024 onward.

Welcome to my 31 day Momtober edging challenge! Each day you'll be given an edging task to go along with that day's Momtober video. Most days you'll not be allowed to cum, but some days you'll be allowed either a ruined or a full orgasm! The last day includes a Trick or Treat themed coin flip ending!

Remember to stay within your limits and have fun! Feel free to skip days, replace them with different videos or modify the challenge to fit within your limits.

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I'm on vacation with my boyfriend, and I caught you sniffing and licking my panties on the security camera I put up! What you didn't know was those panties were what I was wearing when I got creampied the other day... and you just sniffed and licked them! I decide to punish you by giving you a week of sissy tasks. You'll be a full blown sissy slut by the end of the week!

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*This video was a custom, message me to get your own! The name "Mars" is also used in this video.*

I've got a surprise for you... I'm wearing a strapon and I want to give you JOI! You'll follow along with what I'm doing and we'll stroke our cocks together! I tease you with some pegging talk (it's not too intense) as well! No humiliation or sissification in this video.

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*This video was a custom, message me to get your own!* Your new sex robot, Daisy, just arrived and you want to test her out! You turn her on and she walks you through setup instructions... but there seems to be something wrong with her, she keeps stopping mid sentence and her eyes are twitching! No matter, you still want to give her a go! She gets you hard by showing off for you and playing with her robot pussy before she sucks your cock and asks you to fuck her!

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(This was a custom, message me to get your own!) I'm your girlfriend, who has to take a cavity check test soon for class! I was hoping you'd help me? It's going to be weird though... I've collected an odd menagerie of items we need to fit up your ass! They range from a sharpie, to dildos, to a huge vase and everything in between! I hope your ass is feeling especially spacious today because we've got lots of work to do!

If you missed the first video in this series, click here to watch it!

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This was a custom video. DM me to get your own! You and I have been friends for a long time, and I know you've always had a secret crush on me! Well... now I have a boyfriend, and I just found out he's bi and super into short, petite, slightly chubby sissy boys, like you! In fact, he wants to fuck you. There's only one catch, you have to call him (step)Step-daddy! Which would make me (step)Step-mommy, which would make you... our little gal! We'll call you Molly. I give you a cute lacey lingerie outfit to wear for us, then when (step)Step-daddy comes home, I instruct you to greet him with a blowjob. I rub my hairy pussy while I watch (step)Step-daddy facefuck you and then fuck that tight, pretty pink little asshole of yours. After I cum and he gives you an anal creampie, I let you jerk off and cum all over (step)Step-mommy's tits, then you get to lick it all off her tits! That was fun, wasn't it, Molly? I also instruct you to suck your thumb throughout the video!

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This is a simple video of me giving you 5 CBT & Degradation tasks. This is all safe CBT, nothing too intense, and no tools or anything that you shouldn't already have on hand! Enjoy!

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[This was a custom, DM me to get one of your own!] I'm your stepmommy, and I've previously conditioned you to cum ONLY when you're playing with your ass, and ONLY when you're thinking about my feet! So I tease you while naked on the bed with my feet and generously let you sniff my dirty socks. I then tell you I want to try something new... I want to peg your asshole! So I break out my strapon and fuck you in the ass while telling you I want to make you my toilet slave! Please note there is a LOT of talk about toilet stuff, but no actual fluids (or solids lol) are shown. There's no humiliation in this video, and I speak in an ASMR kind of gentle tone throughout the video.

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StepMommy catches you jerking off with her pantyhose and she's ready to teach you a lesson! Think you can handle her punishment of sissification, anal masturbation instructions and CEI?

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This was a custom video (DM me to get your own!) and it is SOLO, there are no other physical people in this video, just you and your imagination! • Your and your wife have gift certificates to my cuck coaching course! I explain to you that you're a beta and this course is meant to put you in your place. Then I bring out a few bulls to play with your wife! I instruct you on how to keep the bulls "fluffed" and everyone cleaned up and hydrated while they're fucking your wife! • TAGS: roleplay role play milf chubby bbw cuckold cuckolding cuckolds cuck cucked cuckolded cucks cucking beta alpha wife cheating cheats cheated bull bulls lesson training trains

Look what I have! I've got your pretty little wife, Suzie in my clutches! I decide to cuck you by domming her, so I strip her down and put her in handcuffs. I put her in a spreader bar and make her sit back and show off her pussy for me while I humiliate you. Then I make her stand up and turn her ass towards you so I can spank it in front of you! Then I taunt you some more as I take her out of the room on a leash. • TAGS: girl lesbian domination lesdom femdom female domme petite thin skinny chubby bbw milf tattoos alt piercings alternative goth glasses married cheating cheats cheated cuckold cuckolds cuckolded cuck cucks cucked humiliation spanking spanks spanked bdsm cuffs bondage

You're back for yet another prostate exam. At this point I'm getting tired of you bothering me and coming into the office! So I give you your exam by sticking increasingly comically large items up your ass (such as a flower vase, a fleshlight and a large flower planter)! I also use your shirt to mop up your cum, sorry! ;) • TAGS: doctor nurse roleplay patient medical med prostate exam examination chubby milf bbw chastity cage device peg pegging pegged anal

**This was a custom video! DM me to get one of your own!** I'm newly widowed and in need of some help, so you and your wife hire me as a live-in nanny & maid. I express how grateful I am to you for helping me out, and then go to collect laundry because I'm eager to get started! As I'm collecting laundry, I walk in the bathroom while you're in the shower on accident. I felt really guilty and ran out immediately, but couldn't help myself from touching myself to the thought of you in the shower! • TAGS: roleplay role play milf nanny maid babysitter widow cheating cheats cheated voyeur masturbation masturbating masturbates alt piercings tattoos chubby bbw

I heard that you have a crush on me.... but the only way you could make me happy is by doing me a favor. My boyfriend LOVES blowjobs but his dick is just too big for me and I'm looking to delegate! I lay out in detail what his cock is like and what he likes from a little twink like you. This was a custom video, and the video ends with me "bringing my boyfriend in", the rest is up to your imagination! | TAGS imposed bi bisexual gay taboo crush roleplay role play blowjob blowjobs blow job jobs bjs bj suck sucks sucking dick cock cuckolding denial chubby bbw milf alt piercings tats tattoos