125,496 listings · Page 525 of 1255
- Your Castration Fantasy-Jackie knows your secret fantasy, you are such a fucking weirdo! You get off on the thought of being castrated. The thought of getting your balls taken off by a sexy woman like Jackie has been your fantasy for years, I’ll today...
- Gloves and Tits-Jackie put on her sexy satin and lace gloves, then she pulls out her huge 42F natural tits. She squeezes her tits while she tells you how good her gloves feel. Jackie describes what she would do to your cock while she wears her gloves...
- Quickie Fat Hairy Pussy Morning Cum-Jackie has just woken up and the Sun is shining! She puts the camera right down at her fat hairy juicy cunt and goes to work on her sweet little clit. She rubs her clit until her pussy starts to drip with cum...
- Teaching Step-Mom to Twerk-It’s your graduation party and Step-Mom seems to be having a lot of fun! Perhaps too much. Step-Mum comes into the room that you and four of your best mates are hanging out in. You saw her dancing earlier and decide you should..
- Your Ex Tricked Your Girlfriend Into Becoming a BBC Slut-Your ex-girlfriend Jackie, who you miss so much, has allowed you to stay at her place as a friend… How pathetic! Well it seems you’ve made a big mistake, you see Jackie has befriended your lovely...
- Jerking Off to Step-Mom's Snoring Ass-Step-Mum is snoring in bed, you walking to see her huge fat around ass exposed completely. You immediately pull out your big boy cock and start jerking it while step-mummy moves around and snores. When Step-Mom...
- Long Tongue Drooling On Oiled Tits-Jackie is all oiled up, her tits are super shiny and ready to get messier. Jackie takes out her long tongue and let’s it drool all over those mega tits of hers. She spits several times all over them until they are...
- Fat Belly Goddess JOI-You can’t get enough of Jackie’s big round belly and she loves that! Jackie’s fat belly gets slathered in lime scented lotion. She rubs it in until her sexy stomach is covered and soft.  she grabs her big belly and jiggles her fat...
- For Tit and Booty Obsessed Losers-Another night of edging to Jackie’s huge boobs and perfect fat ass, you know that’s what losers like you do best! You’re so obsessed with Jackie‘s perfect body, her hairy cunt, her huge tits, and that big fat ass make...
- Patchwork Dress Tease-Jackie has on a sexy patchwork looking dress, and it really amplifies her big booty and her big tits. Jackie shows off her ass, bending over so you can see up her dress. Spoiler alert, she’s not wearing any panties! Watch Jackie...
- Foxy BBW PAWG Yoga-In this clip Jackie has on a tiny pair of foxy pyjamas, and her ass looks absolutely amazing in her shorts! Jackie is stretching and doing yoga, you get to watch her from all angles bending over in her satiny tight shorts, this gives...
- I’m Not Going to Show You My Tits-In this clip Jackie is right up close to you, teasing you with her gorgeous face and her sexy cleavage. She knows how badly you want to see her big perfect natural tits, but she is not going to show you! Jackie flirts...
- You’ll Never Kiss My Lips-Jackie knows how obsessed you are with her sexy red painted lips, but most of all she loves Taunting you with them. You know she only fucks men with big cocks, so you’ll just have to sit there playing with your little dickie...
- Horny Big Step-Sister SPH-Your big step-sister Jackie is so horny that you walk in on her fucking herself with a hairbrush. Seeing your step-sister spread eagle and furiously fucking her cunt gets you hard as a rock! Your big step-sister Jackie is so...
- Jeggings Worship-Jackie has on her sexy blue jeggings. When she bends over you can see that she’s not wearing any panties. Jackie teases you by bouncing that big ass in your face, she pulls down her jeggings so you can see her big white booty. Jackie...
- Step-Aunt Jackie’s Sports Bra-You walk in to find your Step-Aunt Jackie struggling to put on her tight sports bra. Her massive natural tits barely fit! She notices you and is surprised to see you are hard. Go on then step-nephew, pull it out and get to...
- Stupid for Ass Findom-Go on gooner, you know your life revolves around stroking for Jackie’s huge ass. You get so stupid for her, nothing you can do can stop your urge. All you want to do is pay Jackie’s big fat ass. You don’t even need to cum, you just..
- Cum For My Neck-:: This was a custom video for a fan::“I really liked the neck biting clip you did for Halloween, but I want something a little different. I want to admire and worship your long neck I want you to flex it and tense it up if you know what..
- Loving Pegging-Jackie discovered the other night that you really enjoy getting your ass hole licked. Jackie loves you so much, so she decides to bring you a present, an 18 inch big black dildo. It’s a double headed dildo, she wants to put one end in her..
- Mum Tum Worship-You love looking at sexy chubby milfs, their curvaceous bodies and their thick chubby bellies always get your cock so hard. In this clip Jackie is wearing a tight satin purple negligee that really shows off her big round belly. Jackie...
- Tiny Bra Try On-Jackie just got a new clothing haul, and one of the bras that she bought is ridiculously small. She tries it on in front of you and really struggles to get her huge heavy hangers inside it. Once she finally crams them in though her tits...
- Step-Aunt Jackie Makes You Cum Twice-Step-Aunt Jackie is busy getting ready to go out, but she knows that you really need some relief. Step-Aunt Jackie tells you she’s too busy at first, but then she discovers a little hole in her tights. She decides...
- Humiliation Task Series 1-So you want to be a real, true slave to Jackie Synn? Everybody says that darling, but only some of you follow through. That’s why Jackie has created this new series, you must start with episode one. This clip here is going to...
- Loud Booty Clapping in Satin JOI-Jackie is in a sexy, tight, purple satin negligee. It barely covers her big fat white booty, but it looks fucking amazing. Jackie bends over and shows off her booty before she starts clapping it and encouraging you to...
- Sensual Boob Oiling-Jackie is topless and sitting with her huge boobs and her gorgeous face in front of the camera. Jackie slowly and sensually oils her huge boobs, taking time to really massage each one. Jackie makes lots of eye contact while she...
- Big Hippy Tits in Tied Top-Jackie has her huge heavy hangers dangling down in your face. She has on a long sleeve hippy shirt that ties up, making her huge tits look even bigger she jiggles her big boobs right out of her top and right into your face...
- Mean Date Takes Your Wallet-You are on a date with a gorgeous goddess, Jackie. You guys are having a great time when suddenly she asks to see your wallet, you hand it to her and she gets up and walks away. When she comes back she acts like she has no...
- Step-Mom Took Care of Your Bullies-Three boys at school have been really nasty to you and it’s been very upsetting. Last night before you went to bed you were so upset that you cried to yourself, little did you know that step-mummy was busy sorting out...
- CEI No Chickening Out-You’ve been fantasising about swallowing your cum for years, but each time you chicken out. Not this time, Jackie tempts & teases, she knows exactly how to make you do as she says. Jackie tells you how to stroke and when to let it...
- Worship My Tits In a Tiny Top JOI-Jackie has on a tiny white top that is nearly see-through! You can see Jackie‘s big perfect naturals through her top, those big pink nipples and areolas is on full view. Jackie teases you with her big jugs and Instruct...
- Your New BlackmailFantasy Fetish-You’ve recently discovered that the idea being blackmailed gets your cock so fucking hard. In this clip Jackie exploits that, mocking you for your brand-new fetish, and telling you all the trouble you can get into. Get...
- Stop Staring!-:: This was a custom video for a fan:: “ you catch me staring at your cleavage, I will leave it up to you to do what you want with the details. After you catch me you get really angry and start yelling at me to stop staring at you. When I...
- Armpit Hair Growth 2 Weeks-Jackie has been growing out her armpit hair for two weeks. Two weeks ago Jackie let you watch her shave her six months worth of armpit hair growth, time to check in on how her sexy pits are regrowing all that pretty blonde hair
- Are You Sure You Want to Be My Personal Sissy? -Jackie has lots of men that say they love to be sissy boys, they would do anything to be her sissy slut. What they don’t understand is Jackie is not playing around. In this clip Jackie tells you all...
- BBW Trying on Tights-Jackie is getting ready for a big event, she needs to put on some thick black tights. Jackie does not realise that she has outgrown her favourite pair of tights! Oops. Jackie struggles to fit her fat ass and her belly into her tights.
- Break Your Step-Daughter’s Heart Findom-You’ve always been such a hard-working good step-daddy. You’ve always gone without, you’ve scrimped and saved for your step-daughter’s future for years. But lately you’ve noticed that she is growing up to be a bit..
- Forget Your Troubles JOI-Things have been so hard lately, and so uncertain. Jackie knows you have been stressed out, but now it’s time to forget your troubles and focus on her big fucking tits and her expert jerk off instructions. Relax, let go of your...
- I'm Taking Your Money-It feels so good to give all of your money to Jackie Synn, but this time it’s a bit different. Jackie is going to make you give her every last dime in your account, you don’t get a choice in this darling. Prepare to be violated...
- Booty in Sheer Shorts Tease-In this clip Jackie is wearing a sexy pair of sheer shorts. You can see right through them to her perfectly round perfectly jiggly fat ass. Jackie shakes her ass and claps it before pulling them down to expose her bare bottom.
- Hot Wife Tells You About Her Gangbang-Your wife walks in the door early hours of the morning, you know exactly what she’s been up to. Your wife is a hot wife, and you absolutely love it! Jackie tells you about all the fun she’s had with her girlfriend...
- Step-Aunt Jackie’s Taking You on a Picnic-Step-Aunt Jackie is getting ready to take you out for a lovely day, the Sun is shining and she has a picnic basket ready. Step-Aunt Jackie has on a long sleeve shirt that ties up, showing off her sexy chubby...
- BBW Biggest is Best-You are so sick of stroking to silicone injected skinny bitches, the only thing that truly makes you calm are chubby fat women. Jackie knows that BBW is best, she shows off her BBW curves and make you pumped for them. Give in to fat...
- Your Girlfriend Has Small Tits-You have made a huge mistake, you have broken up with Jackie Synn. It’s been over a year but you can’t get Jackie’s big soft tits out of your mind. The way she used to let you fuck them, the way she used to cum when you...
- BBW Leg Shaving-Jackie is also soapy & sexy in her bath. Jackie shaves her shapely legs right in front of your eyes. Jackie’s legs are going to be so soft and smooth!
- BBW Big Wet Bath Tits-Jackie is in the bath in this clip and washing her big natural jugs. Jackie soaps them up good and gives them a nice jiggly tease right in your face! Her tits look so hot when they’re all wet and slippery, would you like to help...
- Goon for BBC-You’ve tried to deny it, but you know that you are born to be a GOONING big black cock slut! In this video Jackie is going to prove it! Jackie shows the pictures of huge black Dick‘s, she encourages you to stroke your dick all night long...
- Week 3 Armpit Hair Growth 3-Jackie just got back from the gym, and she noticed how prickly her armpits felt and how sweaty she is. Jackie shows you her three weeks worth of growth, her pretty little blonde hair coming in nicely! Jackie encourages you to..
- Humiliation Task 2- It’s task number two time! You were such an obedient boy last time, let’s see if you can do it again. This task is pretty extreme, if you have not completed task one go buy that video first. If you find task 2 too humiliating for you..
- Afternoon Bath Ignore-Jackie is lounging in the bath enjoying a good book this afternoon, while you are stuck at work like a sucker. Knowing Jackie gets to spend her days enjoying herself while you slave away paying for her luxury gives you purpose...
- Long Tongue and Big Tits JOI-You have a fetish for long sexy tongues, and big hot natural tits. Jackie has everything you need, she shows off her long tongue and drools all over her big tits. Jackie encourages you to stroke to her perfect naturals and...
- Cowboy Boots JOI-Jackie has on a sexy pair of cowboy boots. She pulls out her big tits and encourages you to start stroking to her boots and her boobs. Jackie knows that you like seeing her dirty boots right in your face, but you also love smelling her...
- Bubblegum Chewing: Double Bubble-Jackie has seven pieces of double bubble bubble gum in her mouth already, but she has room for one more. Jackie chews a nice big hunk of pink gum between her sexy sharp white teeth. Watch Jackie and listen to her smack...
- BBW Hair Washing in the Bath-:: This was a custom video for a fan :: Step-Mom is washing her beautiful blonde hair, and like a good boy, you get to watch & wank to her sexy face and wet hair!
- Sister-in-Law Has a Better Ass-You walk in on your sexy sister-in-law looking a bit upset. It seems she’s had another fight with your wife. Your wife thinks her shorts are too revealing and that she's dressed like a slut. Jackie shows off...
- Red Lipstick Sissy Humiliation-You are such a sissy loser, you get off so hard watching Jackie apply her beautiful red lipstick to her perfect mouth. You will always just be a closet sissy won’t you? Now you’re sat there rubbing your little sissy clit...
- BBC Saves Our Marriage-You come home to find your wife Jackie fucking herself with a bbc dildo, but she stops when she spots you. She’s mad you’re home early, she really wanted to cum! She shows you how creamy she got on her bbc toy, and as punishment...
- Round Rump Oiling-Jackie is oiling up her big booty in this clip, One of your favourite things to see her do with her ass. Jackie makes her buns nice and shiny, bending over and clapping them, spreading them and showing off her sexy body for your....
- Kicking You with My Cowboy Boots-You are such a fucking loser, you are so horny for Jackie’s big fat ass that you will still wank in front of her even while she kicks you in your stupid face and your stupid ball sack. Jackie has on sexy cowboy boots and..
- I Pegged Your Step-Father, Now I’m Going to Peg You Too!-You come home to find Step-Mom yelling at step-dad, you ask what’s going on and step-mum tries to hide it from you but you are persistent. Your persistence pays off because step-Mom has agreed to...
- Strip Club SPH-:: This was a custom video for a fan ::“Hello! I really liked your sph humiliation video (and your hot outfit) where you danced to the song "dont want no short dick man" Could you make me similar kind of clip so the humiliation would feel..
- Bate Buds-Good boys, you took Jackie’s advice and started masturbating together finally. You and your best friend are going to be bate bros, you are going to masturbate together all the time. Jackie encourages you both to stroke to her big sexy porn...
- BubbleGum Freak 3-Jackie is back at it again, she is blowing huge double bubble bubblegum bubbles all over her pretty face. They pop and get all over her, her entire face is covered! Jackie gets sticky blowing bubbles inside of bubbles, snapping her...
- Spending is Your Fetish-You’ve tried to find other fetishes, you’ve even tried to watch alternative porn. You know nothing will ever do the same as giving all of your money to Jackie. Your fetish is spending, you just need to look at Jackie’s perfect...
- Long Leather Skirt Booty Clapping-Jackie has on something unusual for her, a long leather skirt! Normally Jackie likes to wear short skirts to show off her big round ass, but she knew this skirt was so sexy that it would control your cock like crazy...
- Loud Nose Blowing into Tissue-:: This was a custom video for a fan ::Can you make me a nose blowing video where you inhale very deeply and blow your nose as hard and loud as you can, using 2 hands instead of your one handed blows. Loud , long Honking...
- Armpit Hair Growth Week 4-Checking in on Jackie’s pit hair growth 4 weeks after shaving them!
- Make Your Wife a Porn Widow-You know nothing makes you happier and more fulfilled in life then the way that watching porn makes you feel. Jackie wants you to make your wife a porn widow, she’s a useless waste of existence anyway. The only thing you...
- Sissy Tricked By Lady Pimp-Jackie has invited you over under false pretences, she said that she has lots of experience helping sissys like you, that much is not a lie. When she has you looking like a real sissy slut, Jackie confesses that she’s going...
- Coughing Loudly and Spitting Up Phlegm-Jackie has a bit of a cough, actually it’s a really big cough with lots of chest congestion. This morning she has a pretty nasty coughing fit, she spits her fly a man to a Kleenex and shows it to you. Jackie coughs..
- Throat and Neck Fetish-:: This was a custom video for a fan ::“ I would love to watch you swallow some liquid, just watching your throat contract as you swallow gets me so turned on! If you could swallow a couple of pints of water so I can see your...
- Walking, Booty, and Cowboy Boots-In this clip Jackie is walking back and forth showing off her big booty, her sexy cowboy boots, and her thick thighs - walking back and forth pausing to bend over and clap her fat ass in your face. Jackie looks so sexy...
- Cucked by Step-Mom and Jackie Synn-Cucked by Step-Mom and Jackie Synn:: This was a custom video for a fan ::“Hey, I was wondering if you could do a clip similar to “it’s wrong to fantasize about your stepmother†where you talk about you and my Step-Mom...
- Slut Confessions-:: This was a custom video for a fan ::“I want you to sit down and look right into the camera. I want you to tell me how much of a slut you are, and how much you love being a dirty little fucking slut. Tell me how you love to suck dick...
- Tiny Cock Ass Job-:: This was a custom video for a fan ::“your clip titled "small cock bj" covers my fetish like perfectly. I was thinking something that starts out like that using the small dildo with mouth teasing, but then moving to an assjob with...
- Armpit Hair Growth +3 Months-It’s been over three months since Jackie last shaved her armpits! In this clip Jackie tells you about all of the differences between having the hair or not. She loves the way it smells, she has to wear more deodorant, but...
- Step-Daddy Cums for Step-Daughter's Porn Ass-Your wife confronts you after she caught you rifling through your step-daughter's thong drawer, she knows you like to take sneaky peeks at your step-daughters big fat ass. She has developed into quite a...
- BBW PAWG Booty in the Bath-Jackie has her big ass on full display in this clip! Watch the water and bubbles as they wash over Jackie is huge around fat ass. Jackies booty is so hot, and when it’s slippery and wet it’s even more sexy… your cock doesn’t...
- BBW Cums Twice with Feet in Your Face-In this clip Jackie has her vibrating wand on her clit while her big size 10 US feet are right in your face. Jackie shakes and quivers as the buzzing vibe sends her into ecstasy over and over. Watch her feet wiggle...
- Mature is Best-You have a thing for milfs, you always have. Something about a soft doughy mature body, all those curves, it just drives you absolutely wild. In this clip Jackie teases you with her soft curves, pulling up her T-shirt to reveal her round...
- Yoga Pants Creep-You’ve decided to take up yoga to get more flexible, you were not expecting your yoga instructor to be a voluptuous incredibly sexy woman like Jackie! Every time she bends over in her tight yoga pants you can see right through them and...
- Make Me a White Trash Breed Slut-:: This was a custom video for a fan :: “ this is a role-play video where you tell me that you want me to breed you over and over. I want you to make it look like we are fucking at one point, no toys just POV...
- Fat Tits and Belly Oiled Up-Jackie’s huge tits and her big fat belly on full display in this clip. Watch as Jackie sensuously oils up her soft body. Jackie encourages you to jerk off while you watch her get nice and shiny. Jackie‘s big belly and fat...
- Step-Mommy's Porn Zombie-Your step-mum got you a new phone for your 18th birthday, your very first smart phone! You were very excited to see the gift that she left in the phone too, step-mummy loaded your phone with lots and lots of porn! All different...
- Bent Over My Vibrator-Jackie is horny and wants to cum! Jackie bends over and gives you a nice view of her booty cheeks while she grinds hard on her vibrator. Jackie moans she teases her clit before her pussy contracts and gives her an intense orgasm!
- Cum in Your Pants at the Dinner Table-You have such a porn addiction, you can’t tear yourself away even for a minute, not even at the dinner table. You find yourself hard as a rock with your headphones in staring at your screen looking at Jackie. You...
- Expensive Pussy is the Best-You always thought you would try to get away with spending as little as possible on sex workers, you always went to the cheapest camgirls and the cheapest street whores you could find, that was until you discovered Jackie...
- Loser for Armpit Hair-Losers don’t get to see tits, all they get is to worship Jackie's hairy pits! Jackie has grown out her armpit hair out for months now, she knows what a fucking loser you are for her hairy armpits and that you’ll do anything just to..
- My Fat Belly Controls Your Cock-You’re obsessed with Jackie Synn’s curvy, voluptuous fat belly and Jackie loves to tease you with it. Jackie jiggles her fat gut, bending over and giving you a side view of it hanging down. Jackie jiggles it right in your..
- Neighbour Shows You Her Tits-You decided today to drop by to see your neighbour Jackie and have a cup of coffee and a catch up. You were surprised to see Jackie is dressed very inappropriately, but your cock is loving seeing her curves in her tight...
- Fat Ass Oil and Bounce-Jackie fancies teasing your cockwith her huge fat ass! Jackie pulls down her pants, revealing her huge juicy white ass cheeks. She oils them up with baby oil before bending over and clapping that sexy ass right in your face. And...
- Never Fuck Your Wife Again-You have been a devoted wanker to Jackie Synn for a long time now, but Jackie wants to take things up an notch. Jackie insists that you jerk off to her big tits and her perfect fat ass in her tight see-through leggings...
- Step-Aunt Loves Squirting on BBC-Step-Aunt Jackie is super horny today, she can’t wait to make herself cum with her vibrator! You walk in on your chubby step-aunt grinding hard on her vibrator, right on the edge of cumming! You have brought your friend...
- Cozy PJ Ass Worship-Jackie has on a pair of sexy fluffy pyjama leggings. She bends her huge booty over right in front of your face and claps her ass in her pyjama bottoms. She shakes her hips and her booty making your cock throb, then she pulls down...
- Pumpkin Pie Lipstick-It’s autumn so Jackie is switching up her look a bit. Jackie knows how much you love watching her paint her sexy lips, and in this video she shows you her sexy new Jeffree Star pumpkin pie coloured lipstick. Jackie paints her full...
- Sissy Tits Harden Boys Dicks-You have become such a good sissy slut over the years for your perfect goddess Jackie. You have learn to dress like a real slut, put on lots of make up, and take cock like a champ but it’s not enough. If you truly wanna be...
- Step-Daughter Boyfriend Virginity Steal-You and your girlfriend are naked and about to have sex for the very first time when her step-mother walks in the room! Jackie is shocked to see her step-daughter and you, her step-daughter's boyfriend completely...
- Make Your Wife Your Porn Toy-Your wife never wants to have sex anymore, and when she does she is a super lame fuck. You’ve been jerking for Jackie for years, nothing makes you cum harder than staring at Jackie and you would rather jerk your cock looking..
- Fuck off, I’m Trying to Masturbate-Jackie is horny and has her vibrator on her clit, but she is super annoyed that you are here. Jackie tells you to shut the fuck up and just watch her, you don’t get to touch your cock you’re lucky you even get to see...
- BBC Only For Me-This is a quick confessional, Jackie needs to get this off her chest. Jackie absolutely loves black men, she can’t get enough BBC! Jackie shows off your curves in this clip and tells you how she’s constantly got BBC on her mind. Nothing...
- Take Another Hit of Porn-Jackie is horny and wants to get you nice and hard, all while making your head nice and fuzzy. Jackie tells you to jerk your cock and take a hit, hit by hit you get closer and closer. Jackie starts to tease her pussy with her...