Addicted to AddisonAddison leads Ryan to the bedroom, ready to get her pussy fucked deep. She knows how to handle that dick right, taking it balls deep down her throat…

Morning Joe 4Large mocha with extra whipped cream for Ryan! Maserati is back to rock Ryan’s world with her all natural, huge ebony tits. After getting messy with cream in…

TF’s Real Life 20Aubrey brings her perky young tits and fine teen ass over to the Madison’s to get some of Ryan’s good dick. Of course he has the cameras…

Bad Neighbor 3Alix Lovell makes a trip to the grocery store, but doesn’t notice that she’s being followed by her new neighbor. Ryan waits in her bushes as she gets…

Nerd Girls Part 9HER FIRST CREAMPIE! As Jenna wakes up and is ready to start working at her desk in their studio apartment, Ryan decides to jerk off while she’s…

Cheery CheerLayla is the star of her school’s cheer team, or more accurately, her massive ass that the little skirt can’t contain is. When she’s not practicing, she’s putting that…

Real Life #14Skyla Novea returns for a Real Life episode and she’s ready to get dined and dicked deep! After dinner they return to their hotel and quickly get down…

Band Practice 2Kristen needs a lot of help if she’s ever going to be a decent trumpet player. So she goes to Mr. Madison to get some tutoring. He promised…

Nerd Girls 11Gracie loves spending her time reading and studying all sorts of topics. When she’s alone she’ll find an especially steamy topic to research, always leading to her hands…

Take Me NowJessie has been playfully teasing Ryan for weeks now that she’s 18. With her nipples poking out and her panties visible under a knit sweater, Ryan has finally…

Red Hot ShowerAfter her morning yoga routine, Megan steps into the shower to cool off, except things only heat up from there. Lotioning up her fit body turns her on…

Morning Joe 2Kandace Kayne’s FIRST CREAMPIE! Waking up with a hot piece of ass like Kandace Kayne next to you is truly the American Dream! Especially when she’s willing to…

Pool PartyJessa hangs out by the pool, waiting for the pool guy to come by so she can tease him with her perky tits. Watching him clean the leaves from…

Popping Selena’s BubbleWhat better way to spend a summer afternoon than playing with some bubbles while taking a bubble bath outside? Selena works herself up into a lather before heading…

Seduction So SweetDirect from Spain cums Nekane Sweet! This Spanish siren has an all-natural body any red blooded man would be a fool to resist. Her seduction skills are put…

Dirty DancerKira Noir shows off her pole dancing skills to get Ryan hard before going to work on his pole with her mouth. When she said anything goes in the…

Music Box 2, TheWhat’s a lonely clown to do on Halloween? Well if there’s a sexy right down the street, you can always try to lure her into the woods…

No Birth Control CreampieGotta get clean before you can get dirty! Skylar makes sure her pussy is nice and fresh before Ryan comes over to pound that fuckbox. Putting all…

Winter Tail 3On a cold winter night, Izzy thinks about curling up next to the fire with a book, but calls Ryan over instead. There’s nothing like hot, passionate sex…

HeatwaveOf course, the AC goes out on the hottest day of the year! Esperanza is trying to stay cool, even stripping down to just her panties and standing in front…

Music Box 3, TheCute little Ivy Aura falls under the spell of the music box driving her to explore her dark side. Her sexual desires become burning passion as she…

TFSN Cheerleaders 2Head Cheerleader Nicole is about to graduate at the top of her class, not because she works hard and studies. She’d much rather get her pussy filled by…

TF’s Real Life 19All natural blonde cutie Jade Amber wants her pussy full of cream! So she gets all dressed up and heads over to Ryan’s to get exactly what…

Anal Exchange StudentLuna comes all the way from France to study in America. While getting comfortable in her new home, her host’s boyfriend shows up as she’s undressing. Luna notices…

Aerial AngelCome one, come all! See the amazing acrobatic feats of the Aerial Angel Arya Fae! Her acrobatic skills with hoop and silk ribbon are only surpassed by her ability…

Pay the PriceHER FIRST CREAMPIE! To get a girl like Priya Price, you better have the money to spend. She doesn’t come cheap but when a woman this hot starts…

41 Min 11 Sec2 down, 2 to go! After fucking Anna in the ass, Mr. Madison ventures upstairs to find his third victim. An hour has gone by but we’re…

34 Min 16 SecThe countdown begins on this epic day of fucking for Ryan Madison! Riley Reid knows that there is no time to waste and gets down on his…

Clearing the PipesKarmen has some blockage in her bathroom sink, and she gets a recommendation for a handyman from a friend. When Ryan arrives she sees why he was so…

Hard Passion 5HER FIRST CREAM PIE! The stunning Kacey Quinn teases in a tight little white dress, showing off her natural tits and plump ass. It’s no surprise that she’s…

Music Box 4, TheLittle Ivy turns eighteen today and her father’s farm hand has been planning for this day for quite a while. Once she opens the Music Box, Ivy…

Real Life 22Charity might be one of the tightest bodied teens we’ve ever shot! Her fit, young body gets manhandled and treated right by Ryan as he plows her pussy…

Curve AppealPinup babe Lena Paul lives like a modern day Marilyn Monroe. Driven around by Ryan as she goes about her daily shopping. He has a surprise for her back…

42 Min 49 SecThe final chapter! Marica has been waiting for Riley, Anna and Blake to finish with Ryan for over 2 hours! Once he gets her, she slurps up…

29 Min 32 SecThe clock continues to tick as Ryan Madison meets his second girl of the day with Riley still panting on the hallway floor! Anna De Ville has…

TF’s Real Life 21Sierra doesn’t like to waste time she unzips Ryan’s fly and starts sucking him off right on the patio. Looking up at him with her big, blue…

“Pop this DVD in, grab a bucket of popcorn and a bottle of lube and get ready for Teenfidelity’s Teen Matinee. Four hot scenes where Ryan makes the movies you…

All Natural Huge 34FF Tits! Believe it or not, her tits keep growing! Kelly Madison and her world renowned 34FF breasts are pushing 34H NOW! These all natural, perfect proportion,…

The WhiteRoom is a sanctuary for those who like it rough. These 4 girls walk in the door not knowing what to expect but quickly realize that once they leave…

Pump That Rump # 6 Starring AJ Applegate! Pump that Rump is back in it’s 6th installment of Ass-tacular, Ass-tonishing, Ass fucking action! This DVD features more booty shaking and…

“Make’em Sweat returns with even more hot, teen, sports girls getting worked up and sweaty while getting fucked. Whether it’s stretching out in hot yoga, hitting a few balls at…

Some teen girls love to get thrown around aand Ryan takes full advantage of it! These tight bodied chicks get tossed about and get fucked hard in every position. He…

Dress Up

The Sports Edition!Nothing is sexier than beads of sweat running down supple young skin. Carter gets her blood pumping while kicking a soccer ball and running around the field before…

Teen Fidelity’s Perky # 2 Starring Willow Hayes! 2 DISC Set! Over 4 Hours! Plus A Kelly Madison Bonus Scene! We found 4 pairs of the perkiest young tits in…

Break My Hymen returns with volume #3! We’re back with more tight, young, teen twats ready for their first hard fucking! We’re ready to pop these girls’ cherries and show…

Subject to change without notice When you want something bad enough, sometimes you just have to take it. Ryan Madison has his sights on a number of beautiful women, they…

We picked up the hottest street walkers we could find and put them to the test. These working girls own the night and spend it selling their specific set of…