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  #751  
Old 05-05-2018
sailove's Avatar
sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default

Bailey caps.
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  #752  
Old 05-05-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy caps

Sorry don't know the models names.
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  #753  
Old 05-05-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default

Models names unknown.
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  #754  
Old 05-12-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Dom Captions

First one is baily, don't know the models in the last 2.
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  #755  
Old 05-14-2018
fligy1021 fligy1021 is offline
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Default

Quote:
Originally Posted by sailove View Post
First one is baily, don't know the models in the last 2.
#3 is Miranda Meadows
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  #756  
Old 05-14-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Not sure of models names.
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  #757  
Old 05-14-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

A couple more.
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  #758  
Old 05-14-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy caps

I don't like the use of the pronoun "him" for a sissy who has obviously gone through a great deal of trouble to make herself pretty, but I do enjoy the photo!
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  #759  
Old 05-15-2018
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Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default better ...?!

in honour of all sweet asses
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  #760  
Old 05-15-2018
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Howsoon Howsoon is offline
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Default Ooooh

She's right there
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  #761  
Old 05-15-2018
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Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default Missed a sweet taste ...

would really fancy to suck her dry
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  #762  
Old 05-15-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default A better world for all

Quote:
Originally Posted by Boss View Post
in honour of all sweet asses
Yes much better!
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  #763  
Old 05-15-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Tranny captions

Vicky Rickter and the always adorable Patricia Araujo. (sorry if misspelled either of their names, been some time since I've seen them)
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  #764  
Old 05-15-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Don't know the models names, sorry.
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  #765  
Old 05-15-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

More caps I've found.
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3.jpg   never_go_back.jpg  
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  #766  
Old 05-15-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Caption

Like all of us, I have birthday coming up. "all you need is Vaniity baby"
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  #767  
Old 05-15-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Kitty captions

I love Kitty's fuck hole.
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  #768  
Old 05-15-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Don't know the models names. I think the 6th is Gia, not sure though.
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  #769  
Old 05-15-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy caps

Smooth is good.
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  #770  
Old 05-15-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy caps

Don't know the models names, but they make me hard.
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tumblr_p03d61m92m1wwr5y6o1_500.jpg   tumblr_p174ox4epf1wio8bro1_540.jpg   tumblr_p15t17rFss1wwr5y6o1_540.jpg  

tumblr_p04n5juhs51uhsv3uo1_1280.jpg   tumblr_p0587mXMrR1wio8bro1_1280.jpg   18.jpg  

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  #771  
Old 05-15-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Cum eating captions

No such thing as too much cum.
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  #772  
Old 05-16-2018
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Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default Miran says ....:

boy to play with .....
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  #773  
Old 05-16-2018
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Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default My favorite Mistress

Playboys must be trained
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  #774  
Old 05-16-2018
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Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default The battle

How a proud well hung boy will be conquered in the end
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  #775  
Old 05-16-2018
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Howsoon Howsoon is offline
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Default Definitely

What are we waiting for
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  #776  
Old 05-16-2018
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Default

I've enjoyed these so much I made a couple of my own. I hope everyone likes them!

The models are Ariel Everitts, Alejandra, and Tara Emory
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  #777  
Old 05-16-2018
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Default

[QUOTE=Boner;270677]I've enjoyed these so much I made a couple of my own. I hope everyone likes them!

Yes I do like these.
Let's all celebrate fatasy
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  #778  
Old 05-16-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy cap

Don't know the models name, but she does have a nice gape.
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  #779  
Old 05-17-2018
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Howsoon Howsoon is offline
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Default oooo

Well, I'm not going to argue.
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  #780  
Old 05-18-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

A few more captions. The 4th pic is Hazel Tucker.
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  #781  
Old 05-19-2018
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Default

Three of my favorites....Johanna, Jesse, and Kelly Shore!
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  #782  
Old 05-20-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Captions with various themes. Wish I knew the 1st and 2nd girls names. Yum Yum. (Hopefully they aren't fakes)
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  #783  
Old 05-21-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Sissy caps

Some caps with a sissy theme.
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  #784  
Old 05-22-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Not sure of the first, but the second is Hazel Tucker.
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  #785  
Old 05-22-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Various captions

Some of the models look familiar, but I can't remember their names.
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  #786  
Old 05-27-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Not sure if this will upload

A sissy story.
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  #787  
Old 05-27-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default More captions

I Love captioned pics.
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  #788  
Old 05-27-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Captions

Some more captions.
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  #789  
Old 05-27-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default I love sissies

Sissy captions.
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  #790  
Old 05-27-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Captions

Even more captions.
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cap-sissy-180504-03.jpg   cap-sissy-180504-04.jpg   1_0.jpg  

05.jpg   3_0.jpg  

Last edited by dauls; 05-29-2018 at 06:33 AM.
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  #791  
Old 05-27-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Captions

Post more captions.
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Last edited by dauls; 05-29-2018 at 06:33 AM.
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  #792  
Old 05-27-2018
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sailove sailove is offline
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Rectum cock

I have to admit, I Love a cock in my ass.
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  #793  
Old 05-27-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
Default Captions aren't smart by design

One of the stupidest captioned pics I have found. Unbelievably stupid.
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Last edited by sailove; 05-27-2018 at 10:49 AM.
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  #794  
Old 05-28-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Did my best to weed out the fakes.
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  #795  
Old 05-28-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Found a few more caps on my hard drive.
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  #796  
Old 05-28-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Hope I don't dupe any.
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  #797  
Old 05-28-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Let's try a few more.
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  #798  
Old 05-28-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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A few more. THE THIRD PIC I WOULD LOVE TO KNOW HER SHE IS GORGEOUS.
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  #799  
Old 05-29-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Sissies always make me hard
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  #800  
Old 05-29-2018
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sailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud ofsailove has much to be proud of
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Various themes.
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