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!  That and a beer and call it good!  Unless...you can come twice!  So we challenged Payton do all of the above!  And with some excellent concentration and a good little amount of effort...we got to 2 big bangs in the form of 2 Swallows!  Y'all be careful out there and keep all your fingers!  Or better yet let someone else do the fireworks and ask your gal to Blow YOU up in Style instead!  ~SH

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 Asian hands, with their perfect red nails, can barely get around Scott's massive cock.  She uses her mouth, her hands and her tits to bring out his gift of love...a nice load of cum for her to swallow!  Happy Ho Ho Ho's!  ~TWM

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 snow for their adoring red-cheeked faces.

Alexa Night

Xmas Classic Series: Alexa Night

I was decorating and getting ready to hide eggs and in come my hot stud neighbor kid 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.  Kiki stokes while Jocelyn sucks!! What a way to share! Enjoy ~ SH 

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 into it.&nbsp; She turned up for COUGAR SEASON and was looking just as sexy as ever, she has that thick, milfy look going on, nice and juicy and plenty to get hold of. She was really playful before the scene and by the time she came crawling over I was more than ready, her tongue skills inside her mouth were excellent, an absolutely well practiced blowjob! A couple of times I was worried I wouldn’t last, there were so many sensations happening all at once. I think by the time she’d finished swallowing my load she was another step into professional head giver. Nice!&nbsp; Cheers, Frank- Nice&nbsp;

Lola Lee

Well Practiced

New COUGAR SEASONS scene featuring big booty newcumer MILF Alessandra Minutti!&nbsp; More to come!&nbsp; ~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 drained. I was blown away from the instant her 
mouth was on my cock.  Her enormous all natural tits looked too good to 
ignore so I slid my cock in between them.  I fucked them for a bit 
before cumming in her cock craved mouth. And, of course swallowed every 
drop without any hesitation.  ~ ConorThanks Conor!  Wow those are amazing tits!  ~SH

Melanie Hicks

Cock Craved Cougar

The last time we saw Lacy Cummings on COUGAR SEASON it was almost 3 years ago.&nbsp; Now she is back in time for Spring Cleaning by swallowing up loads of cum.&nbsp; And not just 1 scene but 2 ball drainings.&nbsp; Btw, you will notice the near perfect ambidextrous stroking with either hand.&nbsp; Not too many gals can do this well.&nbsp; In fact, its rare.&nbsp; And I can tell you that Lacy is one of the best...with either hand.&nbsp; But she just doesn't miss a beat.&nbsp; This way neither hand gets too tired when shes been stroking your cock for 15 minutes straight and you never notice.&nbsp; Add that to her perfect suck motion and she's one of the best!&nbsp; -SH

Lacy Cummings

Perfect Mother-Stroker

New COUGAR SEASON scene featuring super slender and tall Sofie Marie aka Yummy Sofie&nbsp;@WickedYummy1.&nbsp; Sofie is an ex Triathloner, Volleyball player...and a gal I would bed anytime!&nbsp; Wow.&nbsp; Lucky husband.&nbsp; She has a reminiscent for me of Katherine Ross (for those guys old enough to remember!).&nbsp; Those steely blue eyes, frankly are built for making you cum.&nbsp; I challenged her with a No Hander and she came through like a champ!&nbsp; Loved seeing that butt floss as she steadily sucked hard and sucked all that cum out.&nbsp; I like this gal.&nbsp; Tall, sexy, willing and able.&nbsp; Catch one like this guys and you will never be disappointed!&nbsp; ~SH

Sofie Marie

Catch One Like This!

At COUGAR SEASON we loves us some MILFs!&nbsp; A good Cougar will suck a golf ball through a garden hose to get you your load!&nbsp; Jocyln Stone is no exception!&nbsp; This gal is stacked and loaded for business.&nbsp; You can hit that 5x a day.&nbsp; This thick and substantial gal has tiny little size 5 feet and tiny little hands that can barely fit around her massive DD tits!&nbsp; But this is a girl who likes to please her man as she says to us "make me work for it".&nbsp; Yes maam.&nbsp; Here is a cum-filled cock for you, now get that cum golf ball outta there!&nbsp; ~SH

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 back of her mouth. I couldn't believe how hot this chick was. I
 mean, she looked great in the pics I saw, but when she showed up on my 
door, my fucking jaw hit the floor. She had the most amazing NATURAL 
tits. Ive played with my fair share of big tits, but these things were 
fucking magical. On top of that (well technically below), she had a nice
 plump booty too. Something I'd normally expect to see on a Latina 
chick. If wasn't enough, her accent was to die for. I love a girl with 
an accent, and her was absolutely delightful!! Oh yeah...and she sucked 
my cock too!! LOL. I would have gone to sleep satisfied just seeing this
 chick nude in front of me talking about how much of a little slut she 
is. The fact that she gave my dick a mouth massage pretty much just made
 my week. Forget Moscow Scott, Im heading for Paris! - Kevin SpearsI hear you!&nbsp; Paris it is!&nbsp; ~SH

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 we do just that. &nbsp;No fancy talk, no dinner. &nbsp;Crawl on over here and suck out your protein cum-filled dinner and be a good girl and don't spill. &nbsp;Or at least clean up after your dinner. &nbsp;Great. &nbsp;Now crawl back to the bedroom where I can bang that box! &nbsp;~SH

Leena Sky

Crawl to Dinner

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 stashed away in our Archives.  We will now start to release them as we find them, dust them off, apply some modern editing techniques, and give them a fresh new look.  TODAY'S TWM CLASSIC Before there was Brandi Love -- everyone's favorite new MILF -- there was Janet Mason. This Cougar is pure definition of Cougar!  A body that is truly amazing.  A sexual appetite that needs more than 1 Dick!  And a face made for cum!  Holy shit.  Enjoy this TWM Classic COUGAR SEASON update from the Vaults!  ~SH

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 scenes with Vicky Vixen.  They are correct!  So we dusted it off and re-released it today for a Special Edition of COUGAR SEASON!  Vicky is a flat our Coug!  She is a favorite!  So sexy and dirty that she calls herself "Sticky Vicky"!  Well I can concur.  She gets completely sticky with a deepthroating, tit-fucking, cum-swallowing goodness!  Enjoy guys!  ~SH

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, is a cock-sucking dream.  Loves to stroke, suck, deepthroat her way to a warm facial!  Meow Ms. Kylie, me-fucking-ow.  This the way to celebrate your favorite Cougar cock-sucking day!  ~SH

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 please squeeze her tits, give her a cock, and tell to down a load of your Semen.  Seems like a pleasant English afternoon to me... ~SH

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 COUGAR SEASON.  Brianna is sexy as hell and those shoes...oh yeah I can kinda understand this fetish.  Brianna delivers as always!  And for added measure we had her gulp down her cum dinner off those shoes before she left!  So now she is walking around in those shoes knowing that she slurped a big load off them!  Ok kinda cool...  ~SH

Brianna Bentley

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.  Yuge E tits, super amazing long legs, amazing blue eyes and perfect Dick Sucking Lips (DSLs).  So if that were not enough...shes a total cock-smoking, spit-generating, cum-guzzling Mom-whore.  Our favorite type of Cougars.  I mean who would think this gal -- who you would see in that VIP booth at a club -- would get down and make a mess of her face eagerly waiting for you to bust out your load while she sucks the chrome off your trailer hitch.  Fuckin A.  ~SH

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 stashed away in our Archives.  We will now start to release them as we find them, dust them off, apply some modern editing techniques, and give them a fresh new look.  TODAY'S TWM CLASSIC Gotta love MILFs who have had a kid or two.  That means the backdoor is open.  Anal on the menu.  So that was only real hole, besides that cum-loving mouth, I wanted to fill. Mission accomplished.  Perfection.  Meet Allison Pierce, Anal-ready MILF.  Here to service and serve.  ~SH

Allison Pierce

Here To Service And Serve

Ah Cougars...  Love me a Cougar.  Especially incredibly smoking hot ones like Brianna Bentley.  We first saw Brianna awhile ago.  But now with a whole new camera and set up...we really get to see her for COUGAR SEASON.  And man she is smoking.  Smoking my pole as well.  And getting a perfect helping of cum reward.  A++!  ~SH

TWM CLASSICSWe 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 stashed away in our Archives.  We will now start to release them as we find them, dust them off, apply some modern editing techniques, and give them a fresh new look. TODAY'S TWM CLASSICWe didn't spend enough time worshiping this hot MILF, so we brought her back for round two. What makes Sara James so special? Well, let's start with the body. Curves, curves, curves! She's got an hour glass figure with those wide, baby-making hips that give you something to hold onto when you're plowing her from the back. And her nipples! Those amazing B-cups with nipples the size of gumdrops...and just as sweet too! But of course you don't get to come back for round 2 just because you have a hot body. Her amazing cock sucking is what got her here and this time, we doubled Sara's pleasure with two big cocks. Get your cum rags out and watch this MILF catch a load of cum!

Our Scenes

Total : 175