Josie Cairaway ManyVids Megapack

Collection of Jerk Off Instructional videos, Cum Eating Instructional videos, featuring BBW Josie Cairaway. 95% of it her talking to camera, telling you what a cuck you are and how great it was getting fucked by someone better at it than you. A lot of it is just a close up of her face, a fair bit in lingerie, a fair bit where she is presenting her backside to the camera and very occasionally tits out. Even less occasionally she'll suck some anons dick but usually it's just so she can comment how much better it is that yours.

Main themes are verbal abuse, verbal humiliation.

Mix of 720p and 1080p but picture quality is pretty mediocre.

Sample Descriptions From her Many Vids: Show
I'm The Reason You're In Chastityhi there. no, don't try to put your pants on. i know all about your chastity cage and how your wife makes you stay nude whenever you're at home so she can toy with it whenever she wants. she told me how much fun it is to walk by and flick it or give those balls a squeeze or a smack. she told me that she binge-watched an entire season of her favorite show the other day, with no panties on, and made you lay back with your legs spread in front of her and just stare at her perfect pussy, while she rubbed her feet all over your caged cock and tiny balls for hours. she said she had never seen the shade of blue that your balls turned. my favorite part is that she made you lick up every drop of pre-cum off her foot that leaked out of your pathetically tiny caged cock. i'm here to tell you that all of your sufferings are because of me. well, it's your actions towards me that caused all this actually. remember two months ago at that party when you got tipsy and cornered me where no one could see? you grabbed my tit and tried to kiss me. so i smashed your balls with my knee and left you curled up in pain on the floor. yeah, i told your wife about that. she wanted to divorce you. i told her no....that was far to good for a pathetic bitch like you. i told her about a guy i dated and how much fun we had playing tease and denial and chastity games. he and i mutually enjoyed it, the self-restraint, the self-control it takes to deny, not only the other person, but yourself as well. the problem for him was that i started to enjoy it more than him. he was supposed to be let out of his cage for weekly release. i ruined every one of his orgasms for six months straight. when he came to me crying one day saying he couldn't take it anymore, i called him a pussy and told him that we were through. then i took his chastity key and flushed it down the toilet in front of him. i wonder if he's still locked up…. anyway, she wanted me to come here to allow you out of your cage. don't get too happy. i'm here to ruin your orgasm, not give you one. if you don't ruin it, if you cum, she will send pictures of your tiny caged cock and blue balls to everyone you know. so the choice is yours:ruin your own orgasm or be completely humiliated. let's see what you decide.

Don't Even Think About DatingSo let me guess, you invited me over here tonight to complain about being lonely and no one loving you for you. I've been listening to this whiny spiel of yours for years now. How have you not figured this out? Is the reason that you're always getting dumped and or can never get a date not blatantly obvious? Fine, I'll tell you the reasons since you can't figure them out. You are a loser. You will always be a loser. You&re not smart or funny. There is nothing interesting about you. On top of all those awful qualities, or lack of qualities, you have a micropenis. You should just accept your fate. Stay home and jerk off. Leave those pretty girls alone. It's not just embarrassing for you, it's embarrassing for everyone who knows you - you know, those of us you just sort of glom onto and say we're your "e;friends"e; - to watch you fail time after time with women. You should just accept the fact that you should just be a jerk off junky and give up. I'll make you a deal. I know you've been wanting to fuck me since the moment we met, but just like every other girl, I could tell right away you're pathetic and have a tiny pathetic penis too. For the sake of never having to hear you whine or be embarrassed by your sorry attempts to pick up a girl ever again, I will let you yank your little dick in front of me. Yes, I'm serious. I've started to fantasize about humiliating a tiny dick loser for fun but I only date guys with big dicks. This might be fun for me. I don't know but you should really take me up on this offer because this is probably going to be the closest you ever to get to having sex with a woman again. Go on, take it out. Jesus that is disgustingly small. What are you waiting for? Start stroking. I don't have all day, not that that worthless little thing will take very long to cum. Does something that small cum? Just hurry up and remember our deal. You're just a jerk junky now. No more disturbing pretty girls with your small dicked, loser, weirdness. Oh, one more thing. You will be eating your cum when you're finished. Yes, I'm serious. If you don't we can stop right now? Yeah, I didn't think so. Now work that tiny pecker with your two little fingers and get ready for your snack.

Sissy, Your Bully Is On The WaySo our humiliation games have got a little stale. Dressing you up like a pretty slut, making fun of your tiny penis, just overall humiliating you verbally and physically every day, I&ve been running out of ideas to keep this interesting for me. It will never stop getting old for you, but for me, I needed something to spice it up. You know that guy who picks on you at work and makes your co-workers laugh at you. You know, your work bully. He&s on his way here to pick me up for a date. And yes he knows I&m your wife. Yea, look how red your face got. Aww, you're so embarrassed. I'm just kidding sissy, I wouldn't do that to you, that would be too mean......Ha, Ha, Ha, of course, I'm doing this to you. You're my little sissy bitch and you had to know that someday I would need a real man again. That real man just happens to be your bully. Hold on, let me get a picture of you in your sissy house dress. Perfect. Now, do I send it to him or don't I? No, I'm not going to because he would share it with everyone you work with and they would laugh at you every day. Whoops! I sent it to him. Awww, you look like you're going to cry. I'll tell you what, why don't pull your tiny little clitty out of your panties and yank it for me. See how nice I am, I'm going to let you cum before I go out on a date with your bully. What do you mean, "e;do I have to eat it?"e; Of course, you have to lick that little load right out of your palm when I tell you to finish. You will always eat it, every time you cum, for the rest of your life. This time though I want to get a picture of you doing it. Your bully and I are going to have such a good laugh looking at you licking it all up.

Pretty Feet JOIThis is a very simple game foot slave. You will completely focus on my perfect feet. You will watch every move they make. You will follow every instruction, that I give you, perfectly. You will stroke exactly as you are told. Then you will have the best orgasm your foot obsessed mind and body has ever experienced.

What If I Already DidSo I know we had a crazy night partying last night but do you remember what you asked me to do? No, you don't remember? You asked me if I would cuckold you and then we watched some cuckold porn together. Don't be embarrassed. I thought it was hot actually. I like the idea of still being married to you but fucking other men with bigger dicks. Here's the thing though. What if I already cuckolded you but didn't tell you? Don't be mad. You had to know, on some level, that I've been really dissatisfied with our sex life for a while now. If you didn't know then why are you so into the idea of me having sex with other people? Oh, I see. You think that cuckolding is about you. It's not. It's about a woman being able to find sexual satisfaction wherever she wants with whomever she wants. I found it with a guy I met on my last girls night out. He was hot, he had an amazing body, he was passionate and he gave me the best sex that I've had since college. I haven't cum like that, well, since before I married you. Wow, you really get turned on by this. Oh, I can see that you're angry but your dick is getting hard. You want to jerk off so bad right now, don't you? Do it. Pull out your dick and jerk off in front of your slutty wife. Jerk off while you hear about how hard he fucked me. Yank on your smaller than average dick while you picture his big, fat cock pounding in and out of me. When you cum I want you to thank me for cheating on you. I want you to thank me for making your cuckold dreams come true without you even having to ask. Do you know how lucky you are? Cum while telling me what a lucky cuckold you are and are going to be for the rest of your life.

You Should NOT Have Cheated On MeI&m SOOO PISSED AT YOU! You cheated on me and you didn&t think I would get my revenge. You&re such an idiot. You have a tiny dick and you have the nerve to cheat on ME!. Well now you&re going to pay. I have a huge dick here to suck and guess what…you&re going to suck him too you little bitch.

A Good Sissy Swallows CumYou have become such a good girl for me. Your whole body shaved just like mine. Your makeup technique has become perfect. I doubt that most people would look at you and know that you have a penis. You've done so many things to look so pretty and feminine but to be a real girl you have to keep going. We need to keep pushing your boundaries. We need to make you have an unquenchable desire to swallow male cum. Licking up girl juices is the yummiest thing in the world, I know, and no one is saying you have to give that up. But to be a woman you need to appreciate a hot load from a man sliding down your throat. Today you're going to learn how. Don't worry, I'm not going to rush you into sucking off a guy just yet. You're going to learn by swallowing your own cum first. I want you to pull out your little clitty now and start stroking it. Stroke for me while I tell you what a pretty little girl you are. Stroke while you I tell you what it takes to be a real girl. How you will learn to love the taste of male cum on your tongue. Stroke until your sissy clit cums in your hand then lick it all up like a good girl and swallow it.

You Don't Deserve To Look Up Worship the feet of your Goddess. That's all your good for. You don't deserve to look at the rest of my beautiful body. You don't deserve to look at any part of me other than my soles and jerk your cock. You will never get to touch or fuck your Goddess. You will only ever be allowed to worship my feet. The soles of my perfect feet are the only thing that you will be allowed to jerk off to from now on. Are you peeking? Are you trying to see more of me? Here's a quick flash of my perfect pussy. The perfect pussy that you will never get closer to that you are now. Now get your undeserving eyes back on my feet. I'm going to count you down and you will focus all of your being on my soles. You deserve nothing more.

Media Specs: Show Format                         : MPEG-4
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Codec ID                       : mp42 (mp41/isom)
File size                      : 186 MiB
Duration                       : 5 min 9 s
Overall bit rate               : 5 035 kb/s

Video
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Codec configuration box        : avcC

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Stream size                    : 4.67 MiB (3%)
mdhd_Duration                  : 309440

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Going Out With Cuck Part 1

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Going Out With Cuck Part 2

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Only Ass Worship For You

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You Are So Small

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Queening The Cuck

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Scary Intense Joi

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Stroke With My Strokes

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Mesmerizeeyerollsunglasses Joi Game

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How Badly Do You Want Out

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Mesmerized Into Becoming My Sissy

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Slave Gets To Worship Mistress

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Titty Teasing The Virgin

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Lick His Cum Off My Breasts

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Embezzling Is Wrong Part 2

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Pantyhose Face Sitting

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My Boss Doesnt Like When I Wear Panties

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Cuckolding Ryan Mp4

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Pantyhose Mesmerization

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Kneel Bitch

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Strappy Heels Shoe Worship

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Watch How I Pleased Him With My Tits

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Clean All My Gross Parts Filth Slave

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I Better Cum In Five Minutes

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Open Your Bitch Boy Mouth

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Roommate Foot Slave

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Sissy Social Media Assignments

Josie6girl (2017-06-22)
Mesmerized Edging

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Chastity Anal Training

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Edging Foot Worship

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Punishment For The Premature Ejaculator

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Suck It Weak Bitch Boy

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A Proper Stretching

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Follow Every Inch

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Tongue Fetish Joi

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Fishnet Goddess Worship

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Naked Glove Fetish

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Blow Job Edging Tease

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Too Much Cleavage

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You Cheated Now Youre A Cum Eating Cuck

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Office Jerk Off Slave

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Whipped Balls Jerk Off Session

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Cuckold And The Dirty Gym Socks

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Lick My Sticky Feet Chastity Cuckold

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Lollipop Sph Humiliation

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Ass Worship You Dont Deserve

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Chastity Cuckold Sucks Boot Heel

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Step Son Cei

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Look Dont Touch And Dont Cum

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Foot Worship Cei

Josie6girl (2017-09-30)
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Jerk It Then Eat It You Worthless Worm

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Ignoring You Foot Ass Tease

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Slave Joi Ass Worship

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Lick Your Mess Off My Feet

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Nipple Clamp Cbt Joi

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Close Up Face Sit Joi

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Panty Grinder

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Pantyhose Booty Worship

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Guess Where Your Wife Is

Josie6girl (2017-10-24)
Before You Go

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Only Real Men Get To Fuck Me Now

Josie6girl (2017-10-26)
So You Dont Like My Swearing

Josie6girl (2017-10-31)
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You Better Swallow This Time

Josie6girl (2017-11-11)
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Josie6girl (2017-11-12)
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Josie6girl (2017-11-21)
Show It To Me

Josie6girl (2017-11-21)
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Josie6girl (2017-11-21)
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Josie6girl (2017-12-01)
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Josie6girl (2017-12-13)
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Josie6girl (2017-12-16)
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Josie6girl (2017-12-19)
Not Again

Josie6girl (2017-12-21)
Im Just Here To Pick Something Up

Josie6girl (2017-12-22)
I Know I Said Id Stop But

Josie6girl (2017-12-25)
Big Muscles Tiny Penis

Josie6girl (2017-12-25)
My Sweaty Socks

Josie6girl (2017-12-27)
Ewww Gross

Josie6girl (2017-12-27)
Youre Too Weak To Date

Josie6girl (2017-12-28)
No I Wont Be Wearing The Ring

Josie6girl (2018-01-03)
Misogynistic Husband Mesmerized Sissy

Josie6girl (2018-01-04)
Youre Wearing Panties Today Cuckold

Josie6girl (2018-01-09)
Supervised Masturbation Only

Josie6girl (2018-01-17)
Your Reward A Ruined Orgasm

Josie6girl (2018-02-07)
Your Cage Made You Too Small

Josie6girl (2018-02-09)
You Only Cum With Cock In Your Mouth

Josie6girl (2018-02-13)
Youre My Jerk Off Slave

Josie6girl (2018-02-15)
The Morning After

Josie6girl (2018-02-16)
Youre Funny When Youre Angry

Josie6girl (2018-02-22)
Cock Craving Sissy

Josie6girl (2018-02-22)
Do You Really Want To Be Alone

Josie6girl (2018-02-22)
Ruin It For Me

Josie6girl (2018-02-23)
You Dont Deserve To Look Up

Josie6girl (2018-02-27)
Its All Your Fault

Josie6girl (2018-02-28)
A Good Sissy Swallows Cum

Josie6girl (2018-02-28)
What If I Already Did

Josie6girl (2018-03-01)
Youre A Pathetic Slave

Josie6girl (2018-03-02)
I Own Your Wife

Josie6girl (2018-03-02)
Pretty Feet Joi

Josie6girl (2018-03-07)
Dont Even Think About Dating

Josie6girl (2018-03-07)
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