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Jessica Ryan 295

Jessica Ryan is a 39-year-old actress from United States | See her IAFD Profile, Babepedia page or follow her on Twitter(X)

Jessica Ryan's Newest Videos

Jessica Ryan - Pornstar Collection

Jessica Ryan Mega Collection
121 Videos | 173.66 GB

Jessica Ryan, or Jess as she is sometimes credited in her videos, was born on September 3, 1986, in Colorado. She is a mix of German and Irish origin. Before she dedicated herself to her porn career, Jessica worked as a babysitter and at a movie theater. Besides that, she worked in a chiropractic office, doing tissue massage.Jessica’s porn debut happened on Halloween in 2012 when she was twenty-six years old. The petite porn star with big breasts has a successful career of five years during which she has performed in genres such as interracial, bondage, blowjob, handjob, hardcore, striptease and even teen (thanks to her young looking face).So far, Jessica has shot scenes for productions and website such as Twistys, Mofos, and Naughty America.

Missa X - Jessica Ryan

Jessica Ryan - Jealous Mommy 2
Released: March 2, 2026

Jessica Ryan is a gorgeous single stepmom who’s been feeling touch-starved for quite some time, although she doesn’t want to admit it. Her stepson’s [Parker Ambrose] sweet talk awakens her desires, ending with steamy and sensual lovemaking, a facial, and her creamy pussy dripping with his cum. This scene with Jessica Ryan will have you entranced and desperate for more. What starts as a gentle back and forth between her and her persistent stepson turns into a seductive dance sequence and kisses from her tender, motherly touch, luring you into her private garden. Jessica has been resisting her aching arousal, but Parker knows just how much her pussy needs him. Tonight, he doesn’t hold back, pounding up into her over and over until she’s quivering and clenching around his cock. Which made for a very happy mommy and an exquisite, sloppy creampie.

Missa X - New January & February 2026 Updates

Elizabeth Skylar & Jessica Ryan - The Photoshoot Incident
Bambi Blitz, Gigi Dior - Life After Divorce pt. 3
Nicole Rae - Run Away With Me
Released: January & February 2026

Girlfriends Films - Jessica Ryan & Kaci Kennedy

Jessica Ryan & Kaci Kennedy - My Lesbian Masseuse - Scene 3
Released: February 5, 2026

Black Massive Cocks - New November 2025 Updates

Whitney OC - Blonde Housewife Whitney OC Begs And Bows For BBC
Jessica Ryan - Gorgeous MILF Blonde Jessica Ryan Gets Her Ass Stretched By Big Black
Katrina Colt - Sexy Small Tits Brunette Katrina Colt Wants BBC In Her Ass
Released: November 7, 2025

Housewives Gone Black # 16

Cast: Jessica Ryan, Katrina Colt, Natalia Starr, Whitney OC

Penthouse Gold - Jessica Ryan

Jessica Ryan - Horny for Her Houseguest
Released: November 3, 2025

Jessica Ryan wasn’t looking for anything, she just needed to rent out her guest house. But when Will Pounder strolls in with his suitcase and bulging muscles, the blonde bombshell can’t help but watch his every move through the sliding glass door. As he swims laps, the nympho is lost in the fantasy of her new tenant. Tune in as the horny hottie is caught pleasing herself before the hunky houseguest takes over and plunges himself deep inside the busty beauty on the sofa only on Penthousegold.

She Loves Black - Jessica Ryan

Jessica Ryan - Lovely Handyman
Released: October 28, 2025

Blonde and stunning Jessica Ryan appears truly divine in her white dress and high heels. The blonde babe in glasses exudes natural charisma that makes it difficult to look away once people lay their eyes on her. She’s an alluring woman, and it’s not a surprise that many are attracted to her. Aside from her looks, Jessica Ryan also has a serious demeanor when she’s working. But once she drops the work mode, the lovely beauty is a bright and approachable person who is a delight to talk to.

Horny Household - Jessica Ryan

Jessica Ryan - New Step-Siblings Explore Anal Kink
Released: July 31, 2025

Following the recent marriage of their respective step-parents, sexy young adults, Jessica Ryan and Conor Coxxx, are step-siblings meeting for the first time, and ignite a forbidden spark in this tantalizing encounter. This taboo tale begins in a cozy living room, where Jessica, in a dress with no panties concealing a butt plug, teases her new step-brother with bold confessions about her love for anal. Conor, intrigued but hesitant, admits that he has never explored the backdoor kink, and when his sexy step-sister insists she is a squirter, his sexual skepticism prompts her to lead him to the bedroom to prove it. Jessica then takes charge, stripping to reveal her sparkly anal plug, and spreading her cheeks to flaunt her kink...

Mom Swapped - Jessica Ryan & Justine Jakobs

Jessica Ryan & Justine Jakobs - The Halloween Jizz Games - S5:E2
Released: October 17, 2025

Parker Ambrose and Enzo East are eating their Halloween candy when their stepmothers Jessica Ryan and Justine Jakobs come in and take their treats away. They tell the boys that they're going to play a game. Next thing they know, they're dressed for the Jizz Games and playing dalgona with dick cookies. The milfs win that round.

Missa X - Jessica Ryan

Jessica Ryan - Movie Night with Jessica
Released: August 4, 2025

Liam (Ricky Spanish) is being bossed around by Donnie Rock, who likes to call him "Booger". Donnie also bosses around Liam's stepmom (Jessica Ryan), and is generally a pain-in-the-neck. It's Thursday: movie night where the family settles down in front of the TV to watch a film together. Jessica has a romance film scheduled, but Donnie would rather watch a Wisconsin football game instead. Seeing his family relaxing on the living room couch, he says sarcastically: "If I didn't know any better, I'd think you two are lovebirds".

The Swinger # 8

The.Swinger.8.XXX.720p.WEBRip.MP4-COCKiNE
Cast: Alex Coal, Bunny Madison, Freya Parker, Jessica Ryan

The ghost of Swingers past! When two curious couples check into a Bed and Breakfast for a fun weekend away, one of them discovers a diary left behind by a previous guest. It reveals a series of twists and turns about swinging and swapping and ultimately cheating, leaving our new guests to wonder whether their weekend adventure has too many risks involved.

Mom Wants Creampie - Jessica Ryan

Jessica Ryan - Put My Pussy Where Your Mouth Is - S7:E2
Released: June 11, 2025

Jessica Ryan is on the phone complaining about how she wants a creampie but her husband won't stop pulling out. Her stepson, Gunnar Bishop comes in and tries to get Jessica's attention to sign something for school. To shut him up, she shoves Gunnar's face in her pussy while she disengages from the phone call.

The part of the conversation Gunnar overheard plus Jessica's willingness to have his face in her twat gives Gunnar the courage to come on hard later. He claims he doesn't know what a creampie is and talks Jessica into helping him learn. They start with Gunnar palming and nibbling those titties. Then Jessica urges him to put those hands to work on her pussy. In turn, Jessica gives Gunnar a nice BJ to finish warming up for the main event...

Mommy Blows Best - Jessica Ryan

Jessica Ryan - Meat Day!
Released: June 10, 2025

Lucky Fate thinks he's going to learn how to cook with his girlfriend's Milf, Jessica Ryan. But she doesn't want to cook as much as she has a big craving for eating sausage.

Mommy's Girl - Jessica Ryan & Ophelia Purr

Jessica Ryan & Ophelia Purr - A Spanking Secret
Released: May 17, 2025

A stepmom, Jessica Ryan, confronts her teen stepdaughter, Ophelia Purr, after Jessica's husband finds intimate items from a secret lover in Ophelia's room. The husband disapproves of this and it's up to Jessica to punish Ophelia with a spanking while he's in another nearby room.

Bad Milfs - Jessica Ryan

Jessica Ryan - The Best Mother's Day Gift for His Stepmom? His Virgin Cum
Released: May 11, 2025

I’m a hot mom. It’s no secret that every guy wants to fuck me, and I’m as hot as it gets. At least, my Magic Mirror seems to think so… But he game me an ominous message - To remain as hot as I am right now, I need virgin cum all over my face. I wondered if my sweet little angel of a stepson was a virgin, so I decided to have “the talk” with him, and he confessed that he hadn’t even seen a pair of breasts before. He was shocked when I uncovered my big tits as soon as he said that, but when I grabbed his hand and placed it over my boob as I rubbed his dick, he seemed to be warming up to the idea of fucking me.

Mylf Of The Month - Jessica Ryan

Jessica Ryan - May Spotlight: Jessica Ryan’s Orgasmic Desires
Released: May 3, 2025

MILF lovers! Let’s celebrate May with Mylf of the Month, where we bring one incredible model into the spotlight and see why they’re the best of the best. There are few hotter and more orgasmic than the always beautiful Jessica Ryan. We’ve been working with this drop-dead gorgeous stunner since 2020, and we can’t wait to keep the good times going. We knew we wanted Jessica to have her MYLF spotlight, so we invited her in for an interview and a chance for her to show us why she’s #1. Jessica lets fans in on her desires, her hobbies, all before getting fucked by Gunnar. Jessica shows off her incredible body and loves getting fucked with passion and intensity. Love Jessica? Make sure to tell her in the comments!

Anal Mom - Jessica Ryan

Jessica Ryan - My Pagan Stepmom’s Anal Tribute
Released: April 19, 2025

Jessica and her stepson Will are ready to pay tribute to Eostre, goddess of fertility. They’ve been preparing for this moment their entire lives, and are following the sacred instructions to a tee. Read the words from the ancient book, pray to her will, and get Will’s cock nice and hard so he can complete the ultimate task: pound his stepmom’s asshole as hard as he can so the goddess can hear her primal screams of pleasure.

Teen Swingers!

Cast: Angelina Moon, Athena Heart, Jessica Ryan, Thea Summers

Throated - Jessica Ryan

Jessica Ryan - Jessica Ryan Has An Oral Fixation
Released: March 14, 2025

Jessica Ryan really loves sex. She used to do all the things she was supposed to do, she was engaged but she decided to dump the fiance and get into porn. One of the reasons she did it is because she has access to big dicks to suck. She claims she has an oral fixation and she is about to show it with Donny Sins' prick.

Shoplyfter Mylf - Jessica Ryan

Jessica Ryan - A Mardi Gras Gangbang
Released: March 6, 2025

Rion really screwed up this time! Not only was he caught shoplifting, but he did it right before Mardi Gras, his stepmom Jessica’s favorite event! Dressed in her carnival attire, Jessica arrives at the mall’s security back office to fetch her stepson, now being questioned by not one but three officers: Mike, Chad, and Rion V. The tough security guards know that the young man is hiding something, and their metal detector tells them it might be inside his pants. Unapologetic, Jessica pulls down her boy’s pants to find that his no-good-stepson tried to steal a cock ring...

Missa X - Charlie Forde & Jessica Ryan

Charlie Forde & Jessica Ryan - Persuasion Pt. 3
Released: March 2, 2025

Mom Wants Creampie - Jessica Ryan

Jessica Ryan - Stepmoms Panties - S6:E3
Released: March 5, 2025

Jessica Ryan is doing laundry when her stepson Jimmy Michaels comes in to ask her a question. He confesses that he is interested in his hot teacher while also fondling Jessica's thongs. Eventually, Jessica realizes that Jimmy really has a thing for older women and their panties. When Jimmy asks Jessica to share a secret to make him feel better, she admits she wants a guy to cum on her panties for her...

Missa X - Jessica Ryan

Jessica Ryan - Persuasion Pt. 2
Released: February 21, 2025

In Part 1, Derrick (Ricky Spanish) seduced Angelica Johnson (Charlie Forde), on a dare from his best friend, Angelica's stepson Billy (Nick Strokes). Now, in part 2, it's Billy's turn. Derrick's stepmom (Jessica Ryan) is upset when Billy intimates that her son is up to some hanky-panky with his mom. She wants to go to see what's going on, but BIlly prevents her and gets more aggressive in his flirting with her...

Milf AF - Jessica Ryan

Jessica Ryan - Ripped jeans fuck
Released: January 29, 2025

Jessica Ryan may have been disappointed when she saw the rip in her favorite jeans, but it didn’t take her long to find a way to make the most of it. That sexy MILF put them on to tease her handsome neighbor, and a few minutes later, she finds herself fucking him in the living-room of her house.

Naughty America VR - Jessica Ryan

Jessica Ryan - Jessica Ryan unzips your pants for that thick cock of yours - VR
Released: January 31, 2025

You’ve had your sights set on her a while, and now she’s here for you: Jessica Ryan. Stockinged, with blonde hair flowing, and horny as fuck, the petite diva is going to make you feel good, just the way you want. But first she wants to tease you before she pleases you. Reaching into your pants for that snake of a big thick cock you’ve been hiding, Jessica knows just how to wet it. Her flicking tongue dances all over your massive cock until she slurps up and down it and around the head. When she’s good and ready you’ll find her smooth, fine ass in your sights, prepared to sit right on your dick.

Jay's POV - Jessica Ryan

Jessica Ryan - The Magical Power Of Jessica’s Jeans
Released: January 29, 2025

Club Tug - Jessica Ryan

Jessica Ryan - Cum Hard with Jessica Ryan
Released: December 31, 2024

Give a girl a big dick and she’ll jerk the hell out of it until it explodes. The girl in this equation is the fabulous Jessica Ryan of course. Shes hell bent on making you nut from her intense, yet sensual handjob in this new POV scene from ClubTug. Her handjob skills are epic and when you blow your wad she gets super exited to see cum flying five feet in the air.

OnlyFans Mix December 2024 # 4

Another mix of selected scenes from OnlyFans, ManyVids or other creator platforms released recently.

POV Masters - Jessica Ryan

Jessica Ryan - Curvy MILF Jessica Ryan Rides Hard Cock and Swallow Cum POV
Released: December 2, 2024

Thick MILF Jessica Ryan loves good sex. She is here today to have a good POV sex. Jessica sucks the big hard cock before riding it. She enjoys getting pounded in every position and finally getting the taste of a thick load of cum inside her mouth.

Cuck Hunter - Jessica Ryan

Jessica Ryan - Curvy Blonde MILF Jessica Ryan Rides Friend’s BBC
Released: December 2, 2024

Thick curvy asexual MILF Jessica Ryan calls her big masculine friend to help them move and let them drill her hungry wet pussy. Her pussy is pounded rough as her cuck husband watches. Jessica enjoys the BBC and let him cum all over her thick round ass.

My Stepmoms A Squirter # 2

My.Stepmoms.A.Squirter.2.XXX.1080p.WEBRip.MP4-VSEX
Cast: Alura Jenson, Jessica Ryan, Sarah Vandella, Texas Patti

These hot stepmoms are wet, willing and ready! They love getting fucked and they'll leave you soaked!

Intimacy Productions - Jessica Ryan

Jessica Ryan - Stepbro Questions My Squirting & Anal Skills
Released: November 25, 2024

MILF Dreams

Cast: Jessica Ryan, Penny Barber, Rachael Cavalli, Reagan Foxx

Elegant Angel - Jessica Ryan

Jessica Ryan - MILF Rebound
Released: November 11, 2024

OnlyFans Mix October 2024 # 12

Another mix of selected scenes from OnlyFans, ManyVids or other creator platforms released recently.

Mylf Selects - Swap My Stepmom

Jessica Ryan, Miss Raquel, Silvia Saige, Carmen Valentina, Lilly Hall, Crystal Rush, Brandi Love, Ryan Keely, Penny Barber, Bunny Madison, Crystal Clark, Katrina Colt, Millie Morgan, Lindsey Lakes, Angel Wave, Alaina Taylor, Justine Jakobs, Savvy Suxx, Selina Imai, Ebony Mystique & Annie King - Swap My Stepmom
Released: October 24, 2024

Do stepmoms love to swap? Uh, fuck yeah, they do! If you’ve been with us a while, you know swapping is always on the menu. If you’re new here, strap the fuck in because we’re constantly swapping moms. The stepmoms around here are always teaching valuable lessons, showing their stepsons how to pleasure a woman’s pussy and how to bring her to crazy squirting orgasms. This compilation features some of our favorite stepmom-swapping moments and showcases all of your favorite horny milfs. You won’t want to miss a single second of these mature bombshells getting sexual and playing with forbidden fruit. Big tits, the juiciest asses, and sloshing wet pussies await you in this Selects scene!

Team Skeet Selects - Testing My Stepmom's Ass

Skylar Snow, Jessica Ryan, Katie Morgan, Sofie Marie, Angelina Diamanti, Jackie Hoff, Vivianne DeSilva, Alyssia Vera, Misty Meaner, Jeny B, Sienna Rae & Bree Brooks - Testing My Stepmom's Ass
Released: October 13, 2024

The title says it all! Who wouldn’t want to take their stepmom’s ass for a spin? At TeamSkeet, we have a massive collection of stellar stepmom porn, and you know that collection is getting bigger and better. Within that collection is a ton of fucking wild and downright perverted anal moments. Young studs getting to rock their stepmom’s ass for the fuck of it - what’s not to love? Sometimes, these women need more than their pussies pounded, and nothing is more taboo than slipping it in the backdoor! Whether it’s their first anal experience or they are seasoned pros at taking it up the ass, these women will do anything to have their stepsons inside of them. Butt plugs, ass pounding, clit rubbing, threesomes, and all other types of fucked up, perverted moments await in this bangin’ Selects update!

Naughty Office - Jessica Ryan

Jessica Ryan - Hot blonde boss Jessica Ryan wants to play with your pickle and balls
Released: October 9, 2024

Jessica Ryan stops by Sam's office to ask a favor. She's looking for someone who's athletic to join her Pickleball team. Sam's not really amused until Jessica whips out his pickle and balls to suck and fuck until she gets what she came for.

Mommy Blows Best - Jessica Ryan

Jessica Ryan - Oral Fixation For The Handy Fixer
Released: October 8, 2024

Johnny Palms just finished his repairs in Jessica Ryan's bathroom when she offers to give him a tip. She's a bit sexually frustrated that her husband doesn't love blowjobs. Win/win situations are always a great thing.

Adult Time - Jessica Ryan & Chloe Surreal

Jessica Ryan & Chloe Surreal - Intimately POV Intimately POV - Wet Passion
Released: October 7, 2024

Jessica Ryan and Chloe Surreal nuzzle up to each other as they sit outside in the setting sun, reflecting on their relationship. The older-younger relationship had caused some uncertainty between them in the beginning but has since blossomed into something they both wholeheartedly embrace. As the air begins to chill, they share one more kiss before Jessica leads Chloe inside. From that point on, you experience the world through Jessica's eyes as they fall into bed together and make sweet love, showing all their relationship has to offer.

Perv Therapy - Jessica Ryan & Vanessa Marie

Jessica Ryan & Vanessa Marie - Secret Admission: Our Therapist Wants Us To Fuck
Released: October 5, 2024

Vanessa and Rico are two loving step-siblings who have distanced from each other lately. Their step-parents have sensed that tension and decided to send them to see a therapist. Dr. Ryan has a session with the two teenagers to see what’s going on. It seems that Rico had been going out with a nice girl until Vanessa sabotaged her stepbrother’s relationship. She claims that his cheap ex-girlfriend wasn’t good enough for him, but Rico is mad as hell with his stepsis for meddling.

Gangbang Creampie - Nicole Rae, Jessica Ryan & Sadie Summers

Nicole Rae, Jessica Ryan & Sadie Summers - Reverse Cowgirl September 2 Edition 2024 + Deep In Cream September 2 Edition 2024
Released: September 27, 2024

Gangbang Creampie - Jessica Ryan

Jessica Ryan - Blowbang 427 with Jessica Ryan
Released: September 16, 2024

Mylfwood - Jessica Ryan & Annie King

Jessica Ryan & Annie King - Edward Dildohands
Released: September 23, 2024

Edward Scissorhands is a pretty lonely guy, but his stepmom Annie wants to show him he can do all sorts of wonderful things for people, so she brings her friend Jessica over so he can work on her plants and make them look beautiful. Impressed by his skill, the redheaded beauty asks him to trim her bush next! When he does, she’s so turned on she wants to try a different approach… so the two milfs trade Edwards's fingers for small rubber dildos and suck his cock together on the couch, before he starts fingering their wet pussies with his new and improved hands! Annie gets so horny she bends over and eats her friend’s pussy while his stepson Edward fucks hers. Then it’s Annie’s turn to get her pussy pounded and she goes on all fours before they both take turns riding his big cock until he cums all over their tits!

All Her Luv - New 2024 Updates

Brooke Barclays & Olive Glass - Getting It Back pt. 1
Cadence Lux & Sadie Summers - Falling For a Married Woman
Charlie Forde, Jessica Ryan & Penny Barber - Book Club pt. 2
Cherry Candle & Penny Barber - Is Something Wrong with Me?
Dharma Jones & River Lynn - I Think I Love You

Gangbang Creampie - Jessica Ryan

Jessica Ryan - Gangbang Creampie 427 with Jessica Ryan
Released: September 13, 2024

Lesbian Performers Of The Year 2024

Cast: Freya Parker, Gizelle Blanco, Jessica Ryan, Lauren Phillips, Maya Woulfe, Penny Barber, Serene Siren, Vanna Bardot

Director Pat Myne bring you 8 of the industry's hottest, wettest girl-girl starlets in their annual showcase series "Lesbian Performers of the Year 2024"! This year's batch of awards season favorites get candid about their passion for other women and explore each other's bodies with fingers, tongues, and toys to produce earth-shaking orgasms in the way only a Sapphic can. AVN MILF Performer of the Year Penny Barber gets a taste of Performer of the Year Vanna Bardot; XBIZ MILF Performer of the Year makes love with Freya Parker; Sultry Jessica Ryan gushes over her love of women with sweet Maya Woulfe; finally, renowned lesbian Serene Siren seduces this year's Lesbian Performer of the Year Gizelle Blanco.

Perv Mom - Jessica Ryan

Jessica Ryan - Exhibitionist Stepmilf Likes Being Caught
Released: August 18, 2024

Jessica has a dirty secret, and she never thought her stepson, Tyler, would find out about it. The truth is, Jessica is horny at all times, and being alone at the house all the time, she needs to take out her dirty thoughts using toys. One night, when Jessica thinks Tyler is asleep, she sticks a dildo to her bedroom door and goes for a ride. The fake cock filling up her pussy feels great, but it’s nothing compared to the real thing.

Private - Jessica Ryan

Jessica Ryan - Jessika Ryan Debuts with an Interracial Anal Fuck
Released: August 8, 2024

Brunette and sexy, Jessika Ryan lands at www.private.com today ready to board our brand-new airline in We Fly Mile High, and after meeting the black stallion, Rocket Powers, on the plane, she’s quickly on her way to his place for an afternoon of interracial fun! Upon arrival, there’s no time to waste as Jessica offers up her delicious hairy pussy for a taste before showing off her oral skills with an incredible gagging blowjob. Then it’s time for the real fun to begin as she prepares her tight little ass for a spectacular anal pounding that has quivering with pleasure all the way until a facial cumshot!

Cheating Mommy - Jessica Ryan

Jessica Ryan - Getting Stepmom On Film - S1:E6
Released: July 31, 2024

Jimmy Michaels and Jay Romero listen at the door to see if Jimmy's stepmom, Jessica Ryan, is camming. They open the door to check and realize that Jessica is indeed giving Internet strangers a taste of her goods. The phone glitches, prompting Jimmy and Jay to knock on the door and invite themselves in for a closer look at the goods before she ushers them out...

Oops Family - Jessica Ryan

Jessica Ryan - You Are The Boss Here, Stepmommy
Released: July 26, 2024

This summer, the talented CEO Jessica Ryan arranges an internship at her company for her stepson. However, she warns him not to fuck up this opportunity. As the stepson leaves home for the office, the stepmother eagerly prepares to enjoy her first vacation in years. But for such a workaholic, there’s only one way to unwind. Relaxing on the sofa, the beautiful cougar begins to caress her lovely body and slowly fingers her pussy.

Family Swap - Jessica Ryan & Serena Hill

Jessica Ryan & Serena Hill - Swap Family Doubles Match - S9:E5
Released: July 24, 2024

What would happen if four families each contributed one member to create a new family? In this episode of Family Swap, Serena Hill and her swap mom Jessica Ryan have just gotten nice and sweaty playing tennis. They walk into the living room where Will Pounder is hanging out. The minute Jessica's attention is diverted, Serena begins lifting her tennis skirt and talking dirty to her swap daddy. Jessica insists that Will accompany her to their bedroom to help her with something right now...

Got Filled - Big Tits and Creampies

Maya Farrell, Jessica Ryan, Kenzie Love & Melissa Stratton - Big Tits and Creampies Compilation
Released: July 9, 2024

Big titties and Creampies! Who doesn't love those two together? I decided to make up a collection of some of my favorites for you to watch all in one place!

Glory Hole Secrets - Alexis Abbey & Jessica Ryan

Alexis Abbey & Jessica Ryan - cum comp 06-22-24
Released: June 22, 2024

In the latest Cum Compilation at Gloryhole Secrets, we have Alexis Abbey and Jessica Ryan, who both sucked every drop of cum during their visits with us. Alexis Abbey is first, and her lips and mouth are painted with massive loads of cum out men shared after her excellent cocksucking visit. Alexis Abbey enjoyed seven loads of cum as she pleasured our men & her skills are off the charts. Jessica Ryan also joined us with her blowjob artist skills and blew cum bubbles after our men shot loads of cum down her throat. She enjoys cocksucking, and her blowjobs plus cum bubbles are tremendous. With her seven loads, Jessica Ryan is a Gloryhole dream come true. If you love fourteen loads of cum swallowing, then enjoy this Cum Compilation at Gloryhole Secrets today.

Bellesa Blind Date - Jessica Ryan

Jessica Ryan - Episode 85: Jessica & John
Released: May 25, 2024

Mom Swap - Jessica Ryan & Savvy Suxx

Jessica Ryan & Savvy Suxx - Swapping To Teach a Lesson
Released: May 20, 2024

Anthony comes home tattered and humiliated, and he admits to his stepmom, Jessica, that he is being bullied at school. Jessica demands Anthony reveal who his bully is. Soon after, Jessica calls Savvy, the stepmother of Anthony’s bully, Dylan. Jessica isn’t going just to sit around idly while her stepson gets the snot beat out of him. Jessica and Anthony pay Savvy and Dylan a visit. If Dylan wants to be a bully, Jessica will show him what a real bully looks like.

Glory Hole Secrets - Jessica Ryan

Jessica Ryan - Jessica Ryan's First Gloryhole
Released: May 17, 2024

Her Limit - Jessica Ryan

Jessica Ryan - Anal Addiction
Released: April 15, 2024

Vince Karter is charmed by Jessica Ryan's beauty, wild red hair, and love of gangbangs. She teases him with erotic stories of her past, slowly turning him on before the fun begins. The elegant beauty likes a little pain with her pleasure, and Vince is more than happy to comply, punishing her ass and pussy, making her moan and scream even before he has started to use his massive cock. When the actual fucking begins, the results are truly wild.

Oops Family - Myra Moans & Jessica Ryan

Myra Moans & Jessica Ryan - Take It Off Now!
Released: April 19, 2024

Cutie Myra Moans is a stunning beauty who struggles with self-confidence. How to awake the sexuality hidden inside this chick? Her stepbrother, a fashion expert, overhears her lamenting about her inability to choose the right clothes and attract a boyfriend. In a bid to help, he offers his fashion expertise, and Myra eagerly accepts. Happy Myra quickly takes off her drab clothes, showing all the reasons guys should adore her gorgeous body.

Mylf Selects - MILFs Doing Anal Compilation

Christie Stevens, Miss Raquel, Sheena Ryder, Angelina Diamanti, Cherry Kiss, Shay Sights, Sydney Paige, Armani Black, Sedona Reign & Jessica Ryan - MILFs Doing Anal Compilation
Released: April 11, 2024

What’s up, Mylf lovers? Let’s jump right into the fire and have some fun with this new Selects update! We have a lot of fans of anal sex here, so we wanted to show you all some appreciation with this “MILFs Doing Anal” compilation. These horny milfs love taking it up the ass. For some, maybe it’s their first time. For others, anal sex is the kinky fun they’ve been looking for. We love capturing back-door action and always try to make it daring and taboo. No matter what anal scene you choose from us, you’re always in for a good time. See babes like Armani Black, Christie Stevens, Sheena Ryder, and more!

Mom Wants To Breed - Jessica Ryan

Jessica Ryan - Stepmom Wants Cream Filling On Easter - S4:E5
Released: March 22, 2024

Nick Strokes is eating candy as his stepmom Jessica Ryan cleans up. He asks Jessica why chocolate bunnies are hollow. With a sultry smile, Jessica suggests that it's so they can get filled with cum. It's like a treat for milfs.

Family Sinners - Jessica Ryan

Jessica Ryan - Stepson Seductions 2 - Scene 2 - Sleeping With My Stepson
Released: March 15, 2024

Shoplyfter Mylf - Jessica Ryan

Jessica Ryan - Case No. 6615434 - Model Thief
Released: March 9, 2024

No one escapes the law, not even hot models with long trajectories such as Jessica Ryan. The bodacious milf has been struggling lately to land new gigs because she’s been asked to lose some weight. Unfortunately, she cannot really afford the dieting pills, so she tries stealing them, triggering the mall’s security alarms. Now, she’s taken back for questioning by Officer Vegas, the lustful guard who can’t resist a sexy milf.

Aunt Judy's XXX - Jessica Ryan

Jessica Ryan - After Being Stood Up, Jessica Ryan Sucks & Fucks Her Stepson
Released: March 3, 2024

Redhead MILF Jessica Ryan was hoping to go out to dinner with her husband, but unfortunately he stood her up. Lucky for her, as horny as she is, her stepson just got dumped and has his night free as well. Putting the pieces together and promising to keep it a secret, they decide to stay in and have a little fun together instead. What starts with a little making out quickly escalates as she gets on her knees to suck his cock for a bit, then strips off her green dress to let him suck on her all-natural MILF tits, then spreads her legs to lick and finger fuck her hairy pussy. He fucks her missionary on the edge of the couch, then on the cushions, before switching to doggystyle, then reverse cowgirl, and finally back to missionary when he fills her up with a nice big creampie load

Elegant Angel - Jessica Ryan

Jessica Ryan - Hungry for Squirt
Released: February 26, 2024

Aunt Judy's XXX - Jessica Ryan

Jessica Ryan - Catching Your Stepmom Jessica Ryan Reading A Dirty Adult Novel
Released: February 21, 2024

Your stepmom Jessica Ryan thought she was all alone in the house, trying to soak in a dirty adult novel on her phone, only to look up and see you standing there watching her. Feeling a bit embarrassed after all the moans and facial expressions, she's also shocked to see that bulge growing in your pants. Shocked, but intrigued, she decides to have a little fun with you and invites you to take out your big, hard cock as she drops to her knees to give you a blowjob. Not satisfied with just sucking your dick, she stands and lifts her dress and bends over the chair to get fucked by you from behind, then lifts the dress all the way up to expose her perky natural MILF tits and full bush, to get fucked by you in missionary position, then rides your cock cowgirl style, and you finish blowing your load in her back in missionary position again.

My First Sex Teacher - Jessica Ryan

Jessica Ryan - Professor Jessica Ryan is feeling naughty and wants to be pleasured in class
Released: February 7, 2024

Professor Jessica Ryan asks Joshua to stick around after class to let him know about his school progress. She has been tutoring him on the side so he can catch up on some topics to be learned. She now wants to be paid back for all her hard work helping Joshua out -- and her idea of payback is his stiff cock deep inside her wet professor pussy.

Aunt Judy's XXX - Jessica Ryan

Jessica Ryan - 37yo MILF Jessica Ryan Makes Her Sizzling AJX Debut in this Naughty Taboo Stepmom Scene!
Released: February 2, 2024

Horny redhead MILF Jessica Ryan thought she had plenty of privacy, alone in her bedroom, fully naked, and finger fucking her hairy pussy. However, she looks up to find her stepson has wandered in with a rock hard erection, pretending to be concerned for her safety. Sensing an opportunity to get her needs met, she reaches out and pulls out his hard cock and immediately gets on her back to get fucked hard - missionary, doggystyle, cowgirl, and more, he fucks her hard and gives her an offscreen creampie.

DP Diva - Jessica Ryan

Jessica Ryan - First DP for Naughty Rockstar Jessica Ryan
Released: July 18, 2023

Jessica Ryan is ready for her first DP and to prove she has what it takes to be a DP Diva. The gorgeous redhead with natural tits and booty is full of angst and lust in her rockstar outfit. Her spike brassiere highlights the beauty of her perky tits while her latex skirt makes her round booty appear more appealing. The naughty hottie teasingly takes off her clothes to reveal the full splendor of her naked body. Jessica teasingly spits on her erect nipples, making them more sensitive. Watching the naughty redhead show off her body makes Michael Stefano and Milan want to fuck her as soon as possible...

Mommy Blows Best - Jessica Ryan

Jessica Ryan - Oral Fixation
Released: January 17, 2024

Jack Vegas just lost his job and his passing an interview for a new kind of work as a personal assistant. It seems to go well, but his new boss Jessica Ryan wants to be sure he can fulfil a very special task. She confesses that she has an oral fixation and that she NEEDS to suck dick to keep her mind in the game. The interview ends with a test run of their skills.

Breed Me - Jessica Ryan

Jessica Ryan - Nurse Jessica Ryan
Released: January 10, 2024

Sweetheart Video - Jessica Ryan & Nicole Aria

Jessica Ryan & Nicole Aria - Squirting Lesbians # 7 - Scene 2 - She Squirts
Released: December 11, 2023

Get ready for the hottest, wetting lesbian action! Jessica Ryan and Nicole Aria are brining you the wettest pussies, this is all girl fucking at it’s finest! Dripping squirts keep you cumming like never before!

Naughty America VR - Jessica Ryan & Reagan Foxx

MILF hotties, Jessica Ryan and Reagan Foxx, get a special serving of stuffing this Thanksgiving - VR
Released: November 24, 2023

I live next door to one hot MILF, Jessica Ryan. She calls me out of the blue on Thanksgiving to come by and check her stove that's on the fritz. I show up and it's her and her good friend, Reagan Foxx, whom I've never met. After I fix the issue, these MILFs are so grateful and appreciative. So much so that they'd like to have a little naughty fun while the turkey bakes and before their friends arrive. What a Happy Thanksgiving, indeed!?

All Her Luv - Jessica Ryan & Lacey London

Jessica Ryan & Lacey London - Sgt. Ryan's Home for Wayward Girls pt. 2
Released: August 26, 2023

Previously, Lacey London and Scarlett Sage arrived at the home of Sgt. Ryan (Jessica Ryan), to stay with her in lieu of incarceration at a reform school due to their bad behavior. After laying down the law to them of how she is intent on instilling discipline, Lacey quickly decides to escape and never come back. But her friend Scarlett will miss her, and the two girls make love on the eve of parting. In Part 2, Sgt. Ryan encounters Scarlett in the hallway, and then goes to Lacey's room to check on her.

Mommy Blows Best - Jessica Ryan

Jessica Ryan - Tasty Cock For Jessica
Released: September 13, 2023

Slutty redhead Jessica Ryan cannot control herself and wants to suck on Anthony Pierce's cock!!

Penthouse Gold - Jessica Ryan

Jessica Ryan - Jessica Ryan Craves Repairman's Big Dick
Released: August 22, 2023

Jessica Ryan is the kind of lonely housewife that calls repairmen to her house to fill her horny needs and today Ramon Nomar is the lucky stud that does just that. The horny Penthouse MILF slyly asks him to join her on the couch and soon reaches for his big dick. After she wraps her warm lips around his girthy shaft for a blowjob, he is more than willing to give her the balls-deep fucking that she craves in her hairy pussy. Watch the redhead nympho's natural tits bounce as she rides his rod.

Hustler - Jessica Ryan

Jessica Ryan - Teens Swing With Couples 4
Released: July 29, 2023

Jessica lures Nick into her house with the promise of water, but then makes him drink it off her hairy pussy. She and her husband are both swingers so he loves what he sees. When Khloe comes in, she's shocked to see her boyfriend licking Jessicas's pussy but gets distracted by Jessica's husband. That gives Jessica all the time she needs with Khloe's boyfriend!

Mom's Family Secrets - Jessica Ryan

Jessica Ryan - Keeping Stepmom Happy - S3:E1
Released: July 27, 2023

When you have a hot stepmom like Jessica Ryan, it's important to keep her happy. Ricky Spanish does his best, but Jessica is super hot and he can't help staring at her. Jessica is making coffee in a towel when she drops the cloth to the floor in what she calls a nip slip. Ricky plays it off and claims he saw nothing. Jessica says she'll make a girl very happy, but Ricky only wants to make one girl happy right now...

Distorded - Jessica Ryan

Jessica Ryan - Lounge Encounter
Released: July 14, 2023

She Seduced Me - Angel Dark & Jessica Ryan

Angel Dark & Jessica Ryan - Interview With A Lesbian Vampire
Released: July 3, 2023

Curious girl Jessica Ryan got a once in a lifetime offer, to interview a vampire that goes by the name of Angel Dark! She met her in a dark alley, but soon Angle invited her to her place. It was all mysterious and dark, but Jessica wasn't convinced of it until she saw her fangs while feeding. Little...

Penthouse Gold - New June 2023 Updates

Alektra Blue & Katie Morgan - Lesbians Cum Hard In The Kitchen
Vannesa Sky - Is Stepdaddy'S Big Slut
Madison Wilde - Knows What Daddy Wants
Braylin Bailey & Jessica Ryan - Hot Yoga
Missy Luv - Focuses On Teacher'S Big Dick
Alexis Love & Katie Morgan - Make Lust

Busty brunette Alektra Blue and blonde vixen Katie Morgan are two of the sexiest kitchen staff around in skimpy cosplay outfits, and they are also the horniest. Everyday they find an excuse to have hot lesbian sex and in today's premium Penthouse porn flick, you get a glimpse of their raunchy rendezvous. Watch the big titty babes ravish each other, sensually French kissing and exploring with their tongues and fingers. Then they get even naughtier and bring out the sex toys to cum really hard.

Blacks On Cougars - Jessica Ryan

Jessica Ryan - Jessica Ryan Gets Pounded By Isiah Maxwell
Released: July 2, 2023

She Seduced Me - Ginger Grey , Jessica Ryan & Scarlett Sage

Ginger Grey , Jessica Ryan & Scarlett Sage - Hands On Therapy
Released: June 5, 2023

Lesbian girlfriends Ginger Grey and Scarlett Sage are having issues in the bedroom, which ruins their relationship and sex life, so they decided to go and see a sex therapist. Professional therapist Jessica Ryan pointed out to try her method and kiss in front of her, so she can see firsthand where the...

Anal Mom - Jessica Ryan

Jessica Ryan - To Make Up For The Lost Time
Released: May 13, 2023

Redhead mylf Jessica overhears her stepson Spikey as he’s talking on the phone with his girlfriend about wanting to try anal, but it seems like she’s not up for it. When Jessica goes to talk to him he asks her about her reunion and she mentions that it made her realize that she’s not as adventurous as she used to be. She then reveals that she overheard his conversation and, tapping into her adventurous side, suggests that he could try anal with her!

Elegant Angel - Jessica Ryan

Jessica Ryan - All Natural Anal MILF
Released: May 8, 2023

Family Sinners - Jessica Ryan

Jessica Ryan - Mothers & Stepson - Episode 1
Released: May 5, 2023

The Lesbian Experience - Jessica Ryan & Olivia Madison

Jessica Ryan & Olivia Madison - Olivia Is The Reason For Jessica's Endless Lust
Released: April 15, 2023

Lesbian milf Jessica Ryan cannot eat or sleep and all she thinks about is her beautiful lover Olivia Madison and basking every moment with her touch and sweet dripping wet urges. Jessica rushes home filled with her endless lust to taste Olivia's hot wet pussy and to feel Olivia's big tongue between her lips and sucking on her clit. Jessica, having more experience, opens up her drawer of toys and one by one brings Olivia to orgasms as this lucky day hopefully never ends! - INTERACTIVE TOY READY!

Naughty America VR - Jessica Ryan

Jessica Ryan - MILF nurse Jessica Ryan is trained to drain you balls - VR
Released: April 7, 2023

The 'Dick Diagnosis' is in! Looks like nurse Jessica Ryan is the only one available to take care of you, but luckily she knows how to handle these situations. This naughty nurse is going to have to drain your balls the best way she can. So relax, drop your pants, and let Miss Ryan nurse you to CUMfort.

She Will Cheat - Jessica Ryan

Jessica Ryan - She Will Cheat
Released: March 31, 2023

Mommy Blows Best - Jessica Ryan

Jessica Ryan - Sucking The Student
Released: March 29, 2023

Celtic Iron gets his cock sucked by Teacher Jessica Ryan to help motivate him to do better in class.

Everything Butt - Jessica Ryan & Lily Lane

Jessica Ryan & Lily Lane - Lily Lane Handles Jessica Ryan’s Ass
Released: March 22, 2023

Lily Lane and Jessica Ryan get it on for the first time in this super hot EB update. Princess Lily saunters into the dungeon in her sexy lingerie and high heels to find Jessica is all tied up and eager to please. She starts with the crop on Jessica’s butt, thighs and tender feet getting her all warmed up for a day of all the way girl on girl ass play with lots of big toys. Lily stretches Jessica’s tight hole with bigger and bigger butt plugs and then fucks her ass good with a strap-on dildo causing her to cum hard. Then Princess Lily lures her filthy little toy into her own sexy, curvy ass. Jessica licks Lily clean and then fucks her ass with a thick pink dildo and then an even bigger toy and finally stretches Lily’s ass wide open with an industrial speculum. What a fun play day!

Tag Teaming The Teacher # 2

Cast: Whitney Wright, Paige OwenS, Jessica Ryan, Lolly Dames

Penthouse Gold - Jessica Ryan

Jessica Ryan - Horny Cop Jessica Ryan's Personal Touch
Released: February 20, 2023

Raunchy redhead Jessica Ryan is a police officer seeking donations from local resident Alex Mack using a more personal approach - by giving him a glimpse of her banging body underneath the cop's uniform and a hand on his crotch with a quickly stiffening cock. The stud can't resist the offer of the horny Penthouse MILF when she gets down on her knees to give him a phenomenal blowjob and strips down revealing sexy lingerie and hairy pussy, then shakes her curvy ass while cowgirl fucking him.

Anal Mom - Jessica Ryan

Jessica Ryan - Her Naughty Past
Released: February 9, 2023

After missing an exam, Jessica tries to lecture her stepson Robby but he just ignores her saying she’s only his stepmom so she takes his phone away. Later, Robby is looking for his phone in Jessica’s bedroom and he finds a pair of bunny ears and a naughty letter sent to “Mrs. Bunny Butthole”. Robby decides to confront Jessica about doing porn and ends up asking for a private show! Jessica gives in and changes into her bunny outfit before showing Robby how she takes in a butt plug!

Mommy's Boy - Jessica Ryan

Jessica Ryan - Yogasm
Released: February 8, 2023

Breed Me - Summer Vixen & Jessica Ryan

Summer Vixen & Jessica Ryan - Summer Vixen Becoming Pregnant after Creampie
Released: January 6, 2023

Summer Vixen wants her pussy to be filled up right here, right now, and the sperm clinic is the right place for her. This blonde sexbomb gets naked and grabs the doctor's dick asking him to fuck her in front of his nurse. Summer is screaming and squirting, asking for some buckets of cum deep inside her pussy and won't leave until she gets what she wants.

Breed Me - Vanessa Moon & Jessica Ryan

Vanessa Moon & Jessica Ryan - Real Insemination Fucking
Released: January 3, 2023

Vanessa Moon has decided to have one and wants to speed up the procedure. Thankfully this doctor has the way to make that happen, which means he will fuck her right now. That handsome man puts his cock deep inside her pussy and fucks that beautiful Latina big time before cumming in her.

Mommy's Girl - Jessica Ryan & Hazel Moore

Jessica Ryan & Hazel Moore - World Tour From Home
Released: January 21, 2023

Jessica Ryan is walking down the stairs when she is stopped by her stepdaughter, Hazel Moore, coming out of the bathroom and closing the door quickly behind her. Jessica is surprised and curious as to what Hazel is up to. Hazel explains that since Jessica has gone to so much effort to save up for Hazel's college - so much, in fact, that Jessica has been unable to afford a vacation for herself - Hazel has decided to show her gratitude with a special surprise!

Hustler - Jessica Ryan & Haley Spades

Jessica Ryan & Haley Spades - My Lesbian Mother In Law # 2
Released: January 18, 2023

Jessica hasn't had a woman in a long time and she's quite taken with her daughter in law, Haley. While Haley is sun bathing Jessica rubs some tanning lotion al over her sexy little body and is quickly taken into a hot, girl on girl fantasy!

Mommy's Girl - Rachael Cavalli, Jessica Ryan, Madi Collins & Charli Phoenix

Rachael Cavalli, Jessica Ryan, Madi Collins & Charli Phoenix - One Extra Step
Released: January 14, 2023

If having two stepmoms isn't different enough, what happens when a THIRD gets added into the mix? Well, that's exactly what Rachael Cavalli and Charli Phoenix, a married couple, are thinking about doing. The only problem is... their stepdaughter Madi Collins isn't taking the news quite well. Madi's afraid of change, so it might take a bit of getting used to, but hopefully she'll come around.

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