Tag: Josie Cairaway

Josie Cairaway – JOI StepMom Wants To Top Off Her Fun Night

Hey, stepson. I went out with the girls tonight and had a crazy night. I danced with a bunch of hot guys and more than a few of them were grinding their hard dicks on my ass. I’m so turned on but you know who is useless this late at night for any kind of sexy fun. I’ve been watching you watch me around the house and I think tonight we should have some sexy fun. Your stepmom wants you to pull out that young, thick cock and stroke for me while I touch myself. I’ve been thinking about this a lot and I can see you’re into it too. So, whip that cock out and let’s have fun.

JOI, TABOO, CUM COUNTDOWN, REDHEADS, BIG TITS, MASTURBATION

Continue to download

Josie Cairaway – JOI Stepmom Caught You

Hi, I was just coming to…woah! I didn’t know you were doing that, you should lock the door when you’re jerking off. I’ll just go and…I’m not staring, young man. I’m just noticing that you’re more well endowed than I thought. No, don’t cover up just yet. What do you mean, what do I mean? We have a few more minutes before we have to start getting ready to take you to school. I want to watch you finish. Taboo sex turns me on and watching my step-son stroke his big cock for me is definitely taboo. Since you’re showing me your dick I’m going to show you my sexy parts too. We’re going to play a game while I do though. When I show you my big, 36 DD tits, or my curvaceous ass, you’re going to stroke fast for me. When I put them away you stroke slowly. You will also stop stroking and just play with your balls anytime I tell you to. You will be a good boy for your step-mother and wait until I give you a cum countdown before you shoot that hot load all over. Now start stroking for me, step-son.

JOI GAMES, JOI, TABOO, CUM COUNTDOWN, OLDER WOMAN / YOUNGER MAN, BIG BUTTS

Continue to download

Josie Cairaway – Stepmommy’s Feet Hurt JOI

Oh good, you’re home. I have had the hardest day today. I was on my feet way more than I planned and these heels have made my feet so sore. Would you mind giving me a foot rub? I hate to ask but I could really use one. You don’t mind? Great, let me get these heels off. I have been wearing them all day so sorry if my feet smell a little. Oh, you like the smell? Interesting. Hmm, just like that. Rub harder, really work your thumbs up and down my arches. Now, rub and tug on each one of my toes individually. Yes, just like that. Now, work the ball of my foot. That feels so good. It’s so relaxing, Are you okay? You just suddenly got very red in the face and you look embarrassed. Oh! I see. It’s okay, I like it. In fact, I figured this would happen. I’ve noticed how you’ve been watching me around the house lately. Especially when I wear skirts and heels. All those panty flashes that you think were accidental were nott. I wanted you to look. I’ve been fantasizing about you, in your room, jerking off to my feet and panties. Well, we’re both going to live out a fantasy right now. We’re going to play a little game. You’re going to pull out your cock and stroke it for me. When I put my foot in your mouth, you will stroke slowly and concentrate on pleasing me with your tongue. When I spread my legs and flash you my panties, you will rest your nose against my foot, inhale my scent, and stare at my panties while you stroke faster. You will keep doing this until I give you a cum countdown, naughty boy. Now, open wide and let’s begin.

FOOT FETISH, TABOO, PANTY FETISH, JOI, FEET JOI, JOI GAMES

Continue to download

Josie Cairaway – Stepmom Makes Stepson Wear Panties

So, stepson, how was your day at school? Did you enjoy wearing your stepmom’s panties all day? I think you did. You know you wouldn’t have had to do that if I had not caught you sniffing my dirty panties this morning. That was your punishment. You did do exactly what I told you though and sent me a pic every hour, on the hour, to show me that you were wearing them all day like I instructed you to. So, I think you deserve a reward. Has a girl ever given you a handjob before? No? Well, I think, even though you were bad, you deserve your very first handjob from a girl. Now I’m going to pull these pretty panties to the side, lube up that big cock, and show you just how good a handjob can feel from a woman who knows how to work a dick. Now, I’m going to edge you a few times and play with your balls before I let you cum. You will know when I want you to cum because I’m going to give you a cum countdown. I’ve got a whole other game we’re going to play tomorrow since you’ve taken your punishment so well. I’m going to wear the panties I have on all night, then I’m going to cum in them in the morning, then you’re going to wear my wet, cum soaked panties all day. If you’re good tomorrow I’ll give you your first blowjob. Now let’s start stroking that cock that’s been stuffed into my pretty thong all day.

TABOO, SISSY TRAINING, PANTY FETISH, CUM COUNTDOWN, CUMSHOTS

Continue to download

Josie Cairaway – Rude Stepson’s Ruined Orgasm

Hey there, stepson. We’re all alone in the house tonight, just like every night during the week. I know this is usually when I come up here and strip naked for you. I pull out my big tits and let you play with them. I put my luscious ass in your face. Then I stroke and suck your cock before riding you until you cum deep in your slutty stepmom’s pussy. Not tonight. Tonight you were horribly rude at dinner. You think just because I fuck you that you can be rude to me? There’s nothing further from the truth. I use you as a fuck toy because I want to. You need to be taught whose in charge of this relationship. So instead of giving you a blow job and fucking you, I’m going to use this lube to stroke your cock and edge you over and over. I’m going to deny your orgasm until your body is twitching all over. Then you’re going to take your dick in your hand and ruin an orgasm for me. If, when you start stroking yourself, you cum, I’m going to punch you in the balls so hard that you’ll cry. Oh, and before we get started I’m going to give your ungrateful cock a few hard slaps to show you just how upset I am with you.

RUINED ORGASMS, FEMDOM POV, TABOO, DICK SLAPPING, EDGING GAMES, HANDJOBS

Continue to download

Josie Cairaway – Not Without Permission

Hey, step-son. You and I have to talk. I’ve noticed that you have been acting differently lately. Not in a bad way, just in a way that says you’ve grown up a little. I’m guessing that you’ve started masturbating. Don’t be embarrassed. Everybody does it. Yes, even me. I do it a lot. It feels good and it’s perfectly natural. While it is perfectly natural, we do have a bit of an issue. The reason I noticed that you’ve started masturbating is that you do it a lot. A whole lot. Whenever I pass by your room I hear you letting out quiet little moans, or you have the porn you’re watching turned up a little higher than you thought and I can hear it. The most serious thing it’s affecting is your academics. You’ve been missing school, just so you can stay home and jerk off, and now your grades are slipping. Now, there are two ways we can go about fixing this. The most severe way is for me to buy you a chastity cage and lock your cock in it. Yeah, you should look scared. That means that you will only be able to take it off if you have the key and I will be holding on to that. You will have to wear it everywhere. At school, when you go swimming with your friends. Or, you can willingly give me control of your orgasms and I will jerk you off from now on. The second option sounds much better, doesn’t it? Having step-mommy’s hands all over that big cock instead of it being locked in an embarrassing chastity cage? So, now that we’re agreed, we should start right away.

OLDER WOMAN / YOUNGER MAN, TABOO, HANDJOBS, POV, BIG DICKS, CUMSHOTS

Continue to download

Josie Cairaway – Stepmom Say’s: Edge First Then Cum

Hey stepson. We have the house all to our selves for the night. You know what I want to do. I want to play with your big, rock hard cock. I want you to cum in my mouth. I need to taste a really big load from you so first I’m going to edge you over and over. I want your balls to be really full when I finally let you cum. I’m going to suck, lick, stroke and tease your cock and balls until you’re twitching. Then, when I’ve tasted your pre-cum over and over, I’ll give you a cum countdown. I’m going to lick your balls and show you my tits until I get to one and then you’re going to unload in stepmommy’s mouth so she can swallow your yummy cum.

TABOO, BLOW JOBS, CUM SWALLOWERS, CUM COUNTDOWN, OLDER WOMAN / YOUNGER MAN, REDHEADS

Continue to download