Jizz

Howdy! We ain't all cowboys in the Midwest. Dinglehopper in comments!

ladybonersgw

Jean vest, cowboy hat and NOTHING ELSE is also a good look.

nsfw, Trim, CowboyHats

Silhouette Cowboy

NSFW_GIF

Who doesn't like a cowboy?

ladybonersgw

MsMischievous, I believe this is the hat tip you were asking for? Texan cowboy picture number 2 y'all.

ladybonersgw

Does this subreddit like cowboys?

ladybonersgw

Save a horse, ride a cowboy?

ladybonersgw

I'm a cowboy, on a steel horse I ride.

dragonsfuckingcars

Thick booty urban cowboy

curvy

I'm a Cowboy Baby

milf, SexyFrex

So LBGW likes Firefighters, how about Cowboys?

ladybonersgw

Twerking in my boots and fringe. Saddle up, Cowboy. [F] ALBUM

gonewild

Save a Horse, Ride a Cowboy

ladybonersgw

TIL the term cowboy hat was first used in 1895.

RealGirls, bestofcollege

Corsets and cowboy hats

creampies, bestofcreampies

Y'all seemed to like the Cowboys so much thought I'd give you a little more.

gonewildcurvy

She loves the Cowboys

ass

See you Space Cowboy...

anime

Ride 'em cowboy!

NSFW_GIF, Kappa

Faye Valentine [Cowboy Bebop]

rule34

Save a horse, ride a cowboy...

ladybonersgw, GaybrosGoneWild

[C/C] Cowboys and Indians

wincest

The Cowgirls do a take-off on the Cowboys Cheerleaders poster in an Arny Freytag photo. From Playboy, December 1978.

nsfwsports

NRI Dallas Cowboys Fan! [ALBUM]

IndianTeens

NRI Cowboys Fan Nude Selfies [ALBUM]

IndianBabes

Faye Valentine showcases her ass [Cowboy Bebop]

rule34

Faye and Judy (Izra) [Cowboy Bebop]

rule34

Faye Valentine getting fucked from behind - Animated (Pinoytoons) [Cowboy Bebop]

rule34

Waking up the cowboy

Blowjobs, BlowjobsGalore, tipsdonttouch

Random Vegas pool guy fun (cont) reverse cowboy

Hotwife

Gimme your best shot cowboy!

TributeMe

And many horses were saved that day! My boyfriend trying on a cowboy hat at a thrift store. NSFW

gaybrosgonemild

big boobs cowboy girl

Stacked

Kicking off the cowboy boots in bed

Bulges, broslikeus

Do you want my cowboy hat? [F]

18_19

Perfecting my reverse cowboy [F]

gonewild, ButtsAndBareFeet, ass, u_Bigwooly420

Vintage Cowboy cheerleaders

VintageBabes, tanlines, vgb, u_bryandeanscheibe, u_texashellyea

Faye Valentine ? (Prywinko) [Cowboy Bebop]

rule34

Ride 'Em Reverse Cowboy [MM] (Jonas)

gfur, yiff

Naked Cowboys

VintageGayPics, TotallyStraight

Slight mishap in the Cowboys vs Panthers game tonight NSFW

nrl

Ride Em' Cowboy

FreshGIF, u_lepoirefemme

Save a horse...ride a cowboy ? ?

Hotwife, GWCouples

Does anyone else walk around in nothing but cowboy boots? Just me?

TheHangingBoobs, CowgirlsGoneWild

Shirtless Cowboy (vian)

baramanga

Edit - Faye Valentine #2 (Chris Bryer) [Cowboy Bebop]

rule34

A cowboy taming a cow boy

traphentai, DeliciousTraps

Hand bra and a cowboy hat

countrygirls

Ride 'em Cowboy (BadCoyote)

gfur

Faye Valentine (Cowboy Bebop)

anime_hentai, Rule_34, SmilebluesArchive

Faye Valentine - captured and cuffed (Steven Stahlberg) [Cowboy Bebop]

rule34

Saddle up cowboy

collegesluts, VerticalGifs

I need a real legit cowboy hat though...

CamDamage

Judy (kajinman) [Cowboy Bebop]

Haipantsu, rule34, u_KrazyM50