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Shemales and T-Girls Wearing Hats !! (Very Sexy!!)

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  #251  
Old 08-14-2013
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Carla Cardille in a policewoman's hat. I'd like to be arrested by her and have her conduct a cavity search with her exquisite cock.
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  #252  
Old 08-16-2013
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Ciara, in Cowgirl Cock ...
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  #253  
Old 08-17-2013
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  #254  
Old 09-17-2013
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Luktan cums.
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  #255  
Old 09-26-2013
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This is Gelly ...
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  #256  
Old 09-30-2013
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Bailey Jay playing russian
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  #257  
Old 10-02-2013
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  #258  
Old 10-02-2013
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Holly Harlow...
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  #259  
Old 10-02-2013
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  #260  
Old 12-03-2013
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Karla Desejo ...
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  #261  
Old 12-10-2013
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  #262  
Old 02-09-2014
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Default Joy
What? No hats since back before Christmas?
OK, here's Joy, courtesy of Frank. Nice hat
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  #263  
Old 02-09-2014
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What? No hats since back before Christmas?
OK, here's Joy, courtesy of Frank. Nice hat
She's wearing a hat? I noticed something else that was much more prominent than a hat.
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  #264  
Old 02-09-2014
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Sexy Sierra Ferraro.
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  #265  
Old 02-10-2014
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She's wearing a hat? I noticed something else that was much more prominent than a hat.
Very perceptive, ila!
Of course, it's always nice to find something good under the hat
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  #266  
Old 02-10-2014
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...Of course, it's always nice to find something good under the hat
So very true.
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  #267  
Old 08-28-2014
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Default Riona Aino
No new hats for over 6 months?
Time for a bump, so here's Riona Aino to fix that.
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  #268  
Old 08-28-2014
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Oops... Caught speeding in the Camaro by "Officer Kelly" and will have to pay the price...

Of course I'd let Kelly catch me anytime!
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  #269  
Old 09-23-2014
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Default Infamous
Yes, that's her real porn name but I don't think it's because of her choice in hats. Perhaps some other reason?
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  #270  
Old 08-30-2015
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Soldier girl Kelly removes her hat with the rest of her clothes in this shoot which is a shame because she looks adorable in it!
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  #271  
Old 08-31-2015
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Quote:
Originally Posted by violet lightning View Post
:D I think women look great in hats!! Sexy, Flirty, Sporty, Cool, Elegant.....

Here are some great examples....

Models: Allanah,(2) and Alessandra playing Cops, Sahara,Tara, Unknown,
Alessandra and Terah wearing cowboy hats!!

Yee Haw!!

Comments?
CowGirl Hats ! Save a horse , ride a CowGirl

Yeeeee Hawwwwww !
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  #272  
Old 08-31-2015
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Originally Posted by LuvTSLB View Post
CowGirl Hats ! Save a horse , ride a CowGirl

Yeeeee Hawwwwww !
Cute Cowgirl Kelly could ride me anytime!
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  #273  
Old 08-31-2015
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Originally Posted by violet lightning View Post
I've already posted several pics of Tara.... She loves dressing up, and seems to love hats too!
Here are some more....
Very Classy! :D
Tara was probably the first TS who caught my eye and I haven't looked back.
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  #274  
Old 03-27-2016
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Default Alice
No new hats since last August? Time for a bump, and
I think Alice is just the one to do it
.
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  #275  
Old 03-28-2016
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No new hats since last August? Time for a bump, and
I think Alice is just the one to do it
.
What a great way to start the week with sexy Alice
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  #276  
Old 06-08-2017
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This thread needed a bump.

I'm not sure I'd like this hat on other people but Aubrey Kate looks incredibly sexy in it
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  #277  
Old 10-15-2017
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Why not? Hats are fun.
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  #278  
Old 10-16-2017
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Jessica Host looks very smart with that hat
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  #279  
Old 02-26-2018
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The magnificent Tara Emory!
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  #280  
Old 02-26-2018
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The magnificent Tara Emory!
Lovely, can't go wrong with Tara
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  #281  
Old 02-26-2018
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The magnificent Tara Emory!
Gorgeous. Have never seen these before.

And welcome back Iowaguy82...
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  #282  
Old 02-27-2018
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Since you guys like Tara...here's a couple more!
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  #283  
Old 02-27-2018
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Since you guys like Tara...here's a couple more!
Love it, she's gorgeous. Here's a few from one of the first sets I saw of her a long time ago.
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  #284  
Old 11-12-2020
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Default Jessy Dubai
She looks soooooo sexy in that hat!
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  #285  
Old 11-13-2020
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Ladyboy Bella wears a hat while getting fucked.
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  #286  
Old 11-15-2020
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Default Olivia Love
She looks so cute and sexy- I love her hard body too
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