Featuring Aaliyah Stone, Brianna Bentley, Darryl Hannah, Erica Lauren, Francesa Le, Helly Mae Hellfire. Enjoy!&nbsp; ~SH

Aaliyah Stone

Brianna Bentley

Darryl Hannah

Erica Lauren

Francesca Le

Helly Mae Hellfire

Cougar Season Compilation - Volume 2

Cougar Season Compilation - Volume 1 featuring: Aaliyah Ca Pelle, Brandi Love, Candi Coxx, Darcy Tyler, Erica Lauren and Faustine Lee.

Brandi Love

Aaliyah Ca Pelle

Candi Coxx

Darcy Tyler

Faustine Lee

Cougar Season Compilation - Volume 1

Happy July 4th!  We brought back an oldie but goodie PAYTON LEIGH with a special July 4th Challenge for COUGAR SEASON!  Who doesn't need a nice stroking, sucking and swallowing for the Holiday!  Unless...you can come twice!  So we challen

Payton Leigh

Classic 4th: Blowing Up The 4th In Style!

All I want for Christmas...is a Cougar Blowjob! Its that time of year when it feels good to give. Today CougarSeason is in a gift giving mood. So we dialed up the sexiest Cougar, Mia Rider. We left something under the tree for her. Those little Asi

Mia Rider

Xmas Classic Series: Feels Good To Give

Ho Ho Ho! And we do mean Ho Ho Ho! We have a first class Ho Ho Ho Alexa Night here for Cougar Season white Christmas for you! Its a great time to think about the ones we love...awesome big tittied gals who Ho Ho Ho our Christmas into a load of jizz

Alexa Night

Xmas Classic Series: Alexa Night

I was decorating and getting ready to hide eggs and in come my hot stud neighbor with a basket so I do what I always drain young eggs from young balls! They are the most delicious I have found. ~Payton

Easter Classic: Bunny Fuck

New COUGAR SCENE featuring busty twosome Joclyn Stone & Kiki Daire! Double the curves, double the hands & double the sucking power. This twosome blondes suck it out of the park with their double teaming action.  Joclyn hand strokes while Kiki sucks.  K

Joclyn Stone & Kiki Daire

Share the load

Hi Scott -I got to meet Lola Lee again, I was really excited to see her, she’s very new to the industry and the first time she performed on camera with me she was kinda shy, let me tell you she had mostly got over that and seemed eager to get in

Lola Lee

Well Practiced

New COUGAR SEASONS scene featuring big booty newcumer MILF Alessandra Minutti!More to come!~SH

Alessandra D'Asti

Spicy Bootylicious Newcumer

Hey Scott - Check out curvy girl next door brunette Melanie Hicks!  Sucking
guys off makes her especially happy. Once she starts she doesn't stop 
until your balls are d

Melanie Hicks

Cock Craved Cougar

The last time we saw Lacy Cummings on COUGAR SEASON it was almost 3 years ago.Now she is back in time for Spring Cleaning by swallowing up loads of cum.And not just 1 scene but 2 ball drainings.Btw, you will notice the near perfect ambide

Lacy Cummings

Perfect Mother-Stroker

New COUGAR SEASON scene featuring super slender and tall Sofie Marie aka Yummy Sofie @WickedYummy1.Sofie is an ex Triathloner, Volleyball player...and a gal I would bed anytime!Wow.Lucky husband.She has a reminiscent for me of

Sofie Marie

Catch One Like This!

At COUGAR SEASON we loves us some MILFs!A good Cougar will suck a golf ball through a garden hose to get you your load!Jocyln Stone is no exception!This gal is stacked and loaded for business.You can hit that 5x a day.This thick and subst

Joclyn Stone

Working For It

Oh man Scott, I just had another bombshell over tonight for COUGAR SEASON. And this one 
was French! This voluptuous COUGAR Anissa Kate comes all the way from 
Paris, and tonight her role in American was to drain my balls direct 
into the

Anissa Kate

Forget Moscow

Brand new, and by Brand New we mean Brand New Ebony MILF Samantha Smith giving a No Hands Swallow blowjob for COUGAR SEASON!  This gal can suck a golf ball through a garden hose!  Enjoy all you Ebony-loving-No-Hands fans!  ~SH

Samantha Smith

No Hander Coug

I don't know about you, but I like my MILFs stacked and racked like Lenna Sky. &nbsp;Built for fucking speed. &nbsp;I'd crawl all over that and bang the shit out of that box. &nbsp;But gotta show me what you got first. &nbsp;At COUGAR SEASON 

Leena Sky

Crawl to Dinner

Janet Mason

Cougar Season Classics: Janet Mason

Happy Memorial Day to everyone.  Big shout out to our Vets!  And for today's update its a special update for some of our members, specifically MOFFIZ and JONWICH, both of whom are familiar with our work (mine especially), and recall that we have a few 

Vicky Vixen

Sticky Vicky

Happy Mother's Day motherfuckers!  And for a MILF you can enjoy, we brought you a doozy!  Yes indeed, Ms. Kylie Ireland is in the house for COUGAR SEASON.  Kylie is a redheaded fireball!  This petite and stacked perfect piece of Cougar, i

Kylie Ireland

Redhead Fireball

New COUGAR SEASON from the UK with chesty Chessie Kay!  Our mate Frank told us Chessie and her huge tits, perfect ass and pussy was coming around town and wanted a little young cock.  We said... don't mind if we do Madam!  If you would pl

Chessie Kay

Pleasant English Afternoon

We're listening!  So we have a special member -- CHARLESWRI -- who loves Footwear...shoes.  He's a real loyal member.  So it was time to deliver!  We brought back Brianna Bentley (who doesn't like that!) for our Foot Fetish guys out there at 

Loyalty Has Its Rewards

MILFs!  Ahhh... Who doesn't like a hot MILF.  At COUGAR SEASON we are hunting them down!  Today we have a smokin', smokin', super amazing actual MILF (hard to believe) Corinna Blake.  What is not to love about this gal.  Body is Sick.  Yu

Corinna Blake

Amazing Mom-whore

Recently some members asked -- like BUCKY92 -- asked us when we might have some more MILFs.  Good call Bucky!  So we have a fantastic new English MILF Holly Kiss from Frank in the UK for COUGAR SEASON!  ~SH

Holly Kiss

Good Call!

TWM CLASSICS We are now introducing TWM CLASSICS.  TopWebModels was established in 2002.  We have a library of over 2,000 Scenes.  But many of them, having taken the long journey on the Mayflower, have been stashe

COUGARSEASON Scenes

Total : 177