125,496 listings · Page 523 of 1255
- Weight Gain Update JOI-Being stuck in isolation has Jackie eating loads. In this clip she tells you all about her binge eating while showing off her new curves. You're so weak for her plump body...
- Gaining the COVID 19 Part 2-After pigging out on a fattening sandwich and crisps, Jackie with her swollen belly consumes a huge bowl of frosted flakes. Jackie is watching a true crime documentary...
- Reprogramming: Edge Forever-Stare into the spiral, stare at Jackies tits. You have no control over your own mind, your new purpose is here. Edging feel so much better, it’s all you need.
- Make My Big Naturals Sticky-Jackie has on new lingerie and is showing it off for you. She pulls out her huge naturals and drops, swings and teases with them. All that tit teasing gets Jackie horny...
- Stinky Sock Pervert-Jackie has just taken off her shoes and wow do her feet stink. She notices that this makes you hard and laughs at you, Jackie rubs her stinky socks all over your face how she...
- Mommy Takes Control of Your Cock-::This was a custom video for a fan::"Mom im addicted to that voice of you, your eyes so controlling me,your long tongue,your Delicious spit,your armpits, your nice...
- Cum on My Fat White MILF Ass-This clip Jackie playfully teases you by letting you peek up her pretty blue dress. Seeing her big fat round juicy ass will make you start pumping that dick, and Jackie...
- Little Dicks Don't Deserve to Cum-Your little dicklette is hard staring at Jackie’s cleavage, You are desperate to jerk off while looking at her big pink nipples. Not yet, Jackie wants to tease you...
- Home Wrecker Boss Sucks BBC-It’s performance review day at the office, generally your boss is quite happy with your performance but she’s noticed a change in your demeanour. You confessed that...
- BBW Strong Arms & Thighs-Jackie is a big strong girl, and you're just a weak pathetic boy. You know Jackie could squeeze the life out of you easily, but what a way to go. In this clip, Jackie...
- Reprogramming: Loser for Life-Stare into to the spiral, listen to Jackie’s voice. You’ve always known deep down that you are nothing more than a loser. Reprogram your mind, understand that some...
- For Mommy's Birthday Boy-:: This was a custom video for a fan:: “After 3 weeks leaking hard Get mom pregnant on my birthday Mommy gift on my birthday You invited me to your room to gave me my..."
- Cheese Eating Custom-::This was a custom video for a fan:: "Hi Jackie! I want to watch you eat cheese, whatever kind you like as long as it's the kind you have to slice yourself. I want to see you...
- Gym Perv Blackmail Findom-With lockdown loosening up Jackie is eager to get back to the gym. She finds a generous offer in an ad online: “Use my home gym for free!â€Â Jackie walks in and isn’t sure...
- Loser Ignore Phone Call-Jackie has a loser who loves when she ignores him and takes his money on cam. Tonight Jackie decided to record their session and ring her best friend to laugh at him. Jackie...
- Big Dick JOI to PAWG Booty in See Through Leggings-Jackie has on a skintight pair of leggings that are nearly completely see-through. Jackie loves teasing your big fat cock with her huge PAWG booty...
- Obsessed with My Red Lips-You’re so obsessed with Jackie’s beautiful, full lips. She always has them painted bright red, which makes your cock throb. Jackie gives you an up close view of her hot...
- JOI to PAWG in Silver Metallic Shorts-Jackie has on tight tiny little metallic shorts, and she knows how much you love getting hard for her fat white ass. Jackie gives you expert  jerk off instruction
- Leak for Me Slave-:: This was a custom video for a fan::Â You are so addicted to Jackie, there is no turning back now. In this clip Jackie teases you with all those curves, those huge tits, her...
- Aunt Jackie’s Quarantine Release-It’s the middle of the night, and you are busy spying on your sexy BBW aunt Jackie again. You’ve discovered that aunt Jackie tends to get hot in the night and kick...
- This PAWG Booty is for BBC Only SPH Findom-Poor little dick loser, you can’t stay away from Jackie even though you know you’ll never have a chance. Jackie was built to take BBC and she loves showing..
- Secrets at the Sleepover-Tonight you’re having a sleepover with some friends, they’re getting a little bit wild and rowdy but then Mom walks in. It’s okay, she’s a cool mom, in fact she wants to...
- Losers Don't Get PAWG Booty SPH-Look at Jackie's big fat white ass in those tight little metallic shorts. Now look down at your tiny pathetic dick. You know you stand no chance, the only thing...
- Reprogrammed To Spend & Edge-:: This was a custom video for a fan:: Jackie is at it again, teasing and edging one of her good little pay slaves. Jackie encourages him to let his brain leak out of...
- BBW Cums Fast on Vibrator-Jackie has just finished a fun night on cam. Having all those men spend their money on her and show her their big sticky loads of cum they’ve blown over her has Jackie...
- You're Addicted to BBW MILFS-::This was a custom video for a fan::"I would love if you made a video talking about how much I love bbw milfs/olderwomen. Really like the word mommy too so feel free...
- Harsh Virgin Abuse-:: This was a custom video for a fan:: “I really love your style of humiliation and for This video I want you to really get mean. I want you to humiliate me for being a virgin...
- Fleece Blanket Tease-Jackie is ready to relax. She takes off her clothes and rubs her soft fleece blanket all over her body. Jackie teases you with her big ass, rubbing her warm blanket all over,,,
- Teacher Helps PAWG Addict-:: This Was a custom video for fan Jay::“ The Fantasy: You’re my professor and you’ve noticed my work has been slipping since the quarantine started. You decide to invite...
- Edge More for Me Loser-:: This was a custom video for a fan:: Look who’s back again, poor little loser boy can’t stay away. Don’t you know by now you’ll never escape? Time to carry on edging, now...
- Rattle That Cage-:: This was a custom video for a fan:: Oh dear, what have you gotten yourself into this time slave? Jackie has had you edging for so long and you are desperate to release, but...
- Abusing Little Brother Part 1-:: This was a custom video for a fan::“I come to you, my big sister, to ask to borrow your fancy car and some money. You are appalled, you have just spoken to our mom...
- The Magic of Jackie Synn-:: This was a custom video for a fan::Jackie is in your head, she knows exactly what you need. Exactly what you crave. It’s almost like she has a magical power, an energy...
- Make Big Boy Cummies for Mom's Boobs-Mommy  knows how hard you get for her fat tits, your little boner is throbbing right now just thinking about them, isn’t it? In this clip mommy  brings you POV...
- Abusing Little Brother Part 2-:: This was a custom video for a fan::“ your little brother is back Jackie for more abuse! This time you threaten to release the video of all the filth that you...
- Oiling Cunt for BBC in Front of a Loser-You find Jackie boiling up her gorgeous huge boobs, and you see how turned on it’s making her. Jackie worships her own fat tits and start sucking on her big...
- Cum on Your Screen for My Tits-You’re so fucking hard for Jackie’s massive tits. You can’t start jerking every single day for them, her big natural 42F boobs make you throb like nothing you’ve ever...
- Bubble Gum and Big Boobs-::This was a custom video for a fan:: Jackie’s at it again, blowing big, sticky bubble gum bubbles until they pop all over her face! She attempts double bubbles until they...
- Nurse Takes Your Money Findom-You have recently been diagnosed with COVID-19, you're feeling horrible so you go to see a nurse. You've never seen nurse Jackie before, she assures you she is...
- Sexy PAWG BBW Tease-Your favourite BBW, Jackie Synn, Is looking amazing in her sexy nurse outfit! Jackie teases you with her big juicy booty, clapping it and making your cock throb. And then she...
- Nurse Abuses Your Little Dick-You’ve come to see the nurse because your balls have been sore. When you see how gorgeous nurse Jackie is you are a bit embarrassed to admit to her that your little...
- CEI Gay for Pussy-You, Jackie’s best gay friend confess,  that you’re really bisexual and all of these years you’ve been staring at her hot body fantasising about jerking off to her sweet pussy...
- CFNM Ass Worship-Jackie has on a sexy, tight striped dress that really accentuates her perfect ass. Jackie gives you a tease, making you pump on your hard cock while you are completely naked and she..
- Mommy’s Little Troublemaker-:: This was a custom video for a fan :: “You are my sexy curvaceous mom and you’ve been getting me out of trouble at school for years. The principle is a big black stud...
- A Unique Covid Test-You’ve been feeling very ill lately so you decide you’re better going to have a Covid test. Beautiful nurse Jackie introduces herself, but she is a bit embarrassed that she’s run..
- Armpit Pervert JOI-You are such a weirdo, you get off to the thought of sniffing Jackie’s hairy smelly armpits. Jackie tells you what a loser you are while she puts her gorgeous armpits in your...
- Mesmerising Dress Findom-You are feeling woozy, everything is spinning. You can’t take your eyes off of Jackie and her sexy striped dress. She is taking over your mind, without even trying her dress..
- Wife Makes You Gay for Pay-You’ve convinced your wife Jackie to get into porn to pay off all of your debt. You’ve convinced her to put on a sexy red bathing suit and take some pictures to submit...
- Suck My Heels-Jackie is getting ready for a night out on the town, you know she is going to come home with some nice big cock studs for you both to play with! The thought of Jackie teasing all those..
- Whore Seduces Best Friend’s Dad-Your daughter’s best friend has been living on the streets and getting by as a whore. You have always been a religious man, and you and your wife have found the good...
- MILFs Make You Stroke JOI-You’re such a MILF addict, you find yourself hard following them around the grocery store. You imagine what sluts they are, getting creampied and knocked up. You love their..
- Tickle Torture Talk-Jackie hears you are a very ticklish boy! Jackie loves the idea of tying you to the bed and making you squirm, in this clip she tells you in detail exactly what she would do to...
- Morning Findom-Aw, another all night edging session huh? Well while you’re busy sitting in your own sticky filth as the sun comes up, Jackie is just starting her day. Nothing like draining a losers...
- Laundromat Panty Sissy-I don’t know, it’s laundry day again, Jackie hates going to the laundromat, this one seems especially seedy. As she’s sorting her Dirty clothes she left unattended she notices..
- Red Bodysuit JOI-Jackie has all of her sexy curves encased in a bright red sexy bodysuit. Jackie shows off her perfect curves, tempting your cock until it is desperate for release. She gives you...
- Cuck for Your Ex-Jackie has some bad news, turns out that ex-girlfriend of yours that you can’t get out of your head has a new boyfriend. Turns out he is a super hot black stud who works in the porn..
- Chubby Curves JOI-Jackie has the hottest, curviest chubby body you have ever seen! Her big round juicy ass, her chubby belly and those massive tits always make you want to stroke your cock. Jackie...
- Mommy Vlogger Forgets to Turn Off Livestream-Jackie is a famous mommy vlogger Who goes live every week to give her tips and tricks. After this weeks live stream, all Jackie wants to do is turn off...
- Don’t You Dare Touch Your Cock-Jackie looks amazing and her sexy red bodysuit! Her curves are accentuated in it and have you wanting to wank your dick more than anything. Too bad, losers like you...
- Intox Until You’re Damaged-You want to get fucked up and party with Jackie Synn? Jackie doesn’t play fair, Jackie likes it when you’re a mindless loser. You’re going to want to watch this video over..
- Cleavage Makes You Stroke-You love Jackie is sexy, soft, natural huge tits. They look so amazing in her tiny little bra. Seeing her cleavage always drives you crazy and Jackie loves making you jerk...
- Pussy Free Cuck Husband-Your wife Jackie comes home, you’ve been excited to see her all day because it’s finally your monthly date that she lets you put your pathetic Dick in her! Jackie has some...
- Evil Halloween JOI-You grew up with strict parents who never let you celebrate Halloween, poor you. You were always jealous of the trick or treaters, but mom & dad said it was evil! Once you got...
- Mind Fucked By Ass-Jackie has you so addicted to her big booty, you are absolutely mesmerised by it and will do anything for it. In this clip Jackie has you in a trance with her red bathing suit...
- Trick or Treat Blowjob-You’re a bit old to be trick or treating, but you and your mates are out anyway having some good, wholesome fun. The last house you stop at has run out of candy and the milf...
- Your High School Crush is a Femdom-You show up to a specialty club and you are shocked to see the girl you were absolutely obsessed with in high school is there. This isn’t any ordinary club, this...
- Halloween Cuckolding-(this is a sequel to Trick or Treat Blowjob) You come home late on Halloween night to find your wife VERY happy. She confesses her fun, she's gotten to suck off a young trick...
- Thick Makes You Cheat-Your girl is out at the gym again trying so desperately to build her booty and gain some curves so she can keep you. You’ve always been such a playa in the past, you’ve always...
- Aunt Jackie’s Halloween Pegging-Aunt Jackie has a special surprise under her Halloween dress nephew, a HUGE BBC! It's time Aunt Jackie broke you in properly after years of letting you stroke for her..
- Hurry Up, Your Mom Will Be Home Soon!-You’ve been sitting poolside all morning with your aunt Jackie, sneakily peeking at her heart curves. When you guys go back inside and Jackie starts playfully...
- Halloween Party Husband Mixup-Jackie's clearly been having too much fun at the Halloween party, the room is spinning and she's a bit confused. Thankfully, her husband is here to look after her, or...
- There’s No Quitting Jackie Synn-:: This was a custom video for a fan:: You thought you could get away, did you piggy? You ought to know by now that Jackie Synn is in very deep, deep into your soul...
- Pumpkin Booty-Jackie's PAWG pumpkin booty is on full display tonight, what a treat! She teases you & claps it while encouraging you to jerk off to her fat white booty. Bigger than two pumpkins, that..
- Messiest Bubblegum Bubbles Part 2-:: This was a custom video for a fan :: “ Same look as the last one but also the same results as the Messiest Bubblegum Bubbles video.... That's why I titled this...
- Ghost Makes You Cum-You can’t sleep, suddenly a ghostly apparition appears... and her booty is huge! This spooky slut teases you with her PAWG booty, clapping it and encouraging you to nut. Your...
- Dirty Toilet Fag-You are really a disgusting pervert! You’ve always gotten off on the thought of being a nasty toilet slave to a beautiful woman, but recently you figured it out... You just love...
- DÃa De Los Orgasmo-This BBW in a sugar skull mask is horny and needs to cum! Watch her as she grinds her clit on a vibrator, giving herself an intense, wet orgasm!
- Natural Toes for Foot Pervert-What a rare treat for some of Jackie's foot perverts, her toes have no polish today! Jackie's big sexy natural feet in your face make you such a weakling. Go on then...
- CBT Muscle Cream Clothes Pegs and a Hair Brush-Jackie is so cruel, she loves torturing pathetic dicks like yours! You’ll do anything for Jackie even torturing your own penis and make it hurt for her..
- Gay Conversion Therapy Gone Wrong-You’ve had a lot of past trauma you are trying to work through, and it is really affecting your sex life. You come to a therapist for some gay conversion therapy...
- Witch Makes You Cheat-You’ve been trying so hard to be a good husband ever since your wife found out how much porn you consume behind her back. If I’m going to couples therapy and for almost a year...
- Witch Ruins Your New Cock SPH-You have a tiny Dick and you are fed up with it so you go to visit a witch who specialises in cock sorcery. Jackie the witch does not disappoint, she gives you a thick...
- Witch Tease-Jackie is wearing her sexy witch Halloween costume and her BBW curves look amazing in it! Jackie teases you with her big booty and her huge boobs! Jackie tells you she likes it when you...
- Witch Mocks Your Skull-Jackie’s boyfriend has cheated on her for the last time. You see, he didn’t realise that his girlfriend Jackie was a witch! Jackie was sick and tired of being cheated on so...
- Quarantined for Life-When you heard everyone was going to have to go into lockdown, a big rush of panic fell over you. Quarantined?! Oh no what will you do with your busy social life? Oh that’s...
- Bite My Neck-Jackie is about to get it on for the first time with her new boyfriend, but he’s got a confession. Turns out he’s a vampire! Jackie thinks it’s hot and offers up her long, lovely neck...
- Cum with Your High School Crush-::This was a custom video for a fan::“So after a night of drinking and dancing Invite you back to my hotel suite we do a little more drinking and smoking. You were my..
- Booty Clapping in a Long Skirt-Jackie has her PAWG booty covered with a long cotton rainbow coloured skirt. Jackie bends her fat milf ass over and shakes it and tease you with it, before clapping it..
- Cursed Step Mom Inflation-:: This was a custom video for a fan :: “ POV weight gain/inflation roleplay where you play a mean stepmother who gets cursed by your stepchild to rapidly gain weight. You...
- Strip Club Manager Punishes Fuckboy-You’ve had a little too much fun at the strip club tonight, you’ve definitely got in to handsy with a lot of the girls. You thought you can pay your way into...
- Big Naturals Dangling in Tube Top-Jackie busted out of her bra, and you can definitely see her big protruding nipples through her cotton tube top! Jackie dangles them over your face, squeezing them...
- Messiest Bubble Gum Bubbles 3-Jackie has eight pieces of double bubble bubblegum in her mouth, and she sure knows how to use it! In this clip Jackie snaps her gum loudly, Blows bubbles in bubbles...
- Intake Camel Toe Worship-Look who’s back again, Jackie’s little sniffer piggy! You’re down on your knees where you belong ready to worship Jackie‘s perfect cleavage and her sexy camel toe. Jackie‘s meaty hairy cunt is right in your face covered only by...
- I Cheat Because I Love You - It’s Valentine’s Day and your wife Jackie is looking amazingly sexy in her pink dress. When you see the hearts on her dress you assume she is getting ready for a wonderful night out with you, how could you be so stupid? ...
- White Penis Counciling
- Tricked into Becoming a Webcam Whore-Jackie has been visiting with a girlfriend tonight, they haven’t been able to catch up in ages. The pandemic has caused Jackie to lose her job and she’s getting quite desperate for cash she confesses, she also...
- Oiled Booty Clapping in Purple Dress-Jackie has on a tight purple fishnet dress, it shows off all of her major curves. Jackie oils up her fat ass and starts bouncing it nice and hard, clapping it all around letting it jiggle wobble and shake. Jackie’s...
- Intox Brain Fucked for Valentines Day-Another Valentine’s Day alone? Don’t worry loser, Jackie is here for you! Tonight you were gonna really properly fuck that brain up - so much so it might go POP! Grab your supplies, tonight you are going to get...
- Youre Too Young to Look at My Bum-Your teaching assistant Jackie has come round for another lesson. It’s been a while and you are really excited to see her, so excited that you can’t take your eyes off of a big round juicy bum. As Jackie is bending over,
- Making Your Wife Watch While You Jerk Off to Jackie Synn-You are such a Jackie Synn fan, you buy all of her videos and spend thousands on live shows with her! You do all this behind your ugly wife’s back, you don’t even feel bad about it. Your wife...