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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
Models names unknown.
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13.jpg   1.jpg   001.jpg  

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  #752  
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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  #753  
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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  #754  
Old 05-14-2018
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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 models names.
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12_1.jpg   22_0.jpg   12_00.jpg  

cuck_ir_676a.jpg   8 (1).jpg   8.jpg  

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  #755  
Old 05-14-2018
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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 couple more.
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01.jpg   PB_38.jpg  
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  #756  
Old 05-14-2018
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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
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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  #757  
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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caption 001_01.jpg  
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  #758  
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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  #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 Missed a sweet taste ...
would really fancy to suck her dry
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  #760  
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 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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  #761  
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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102.jpg   Sissy_Shemale_caps_1_211153537.jpg  
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  #762  
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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2.jpg   CAGED.jpg   maids.jpg  

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  #763  
Old 05-15-2018
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 Various captions
More caps I've found.
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3_0.jpg   2_0002.jpg   debut.jpg  

3.jpg   never_go_back.jpg  
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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 Caption
Like all of us, I have birthday coming up. "all you need is Vaniity baby"
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001.jpg  
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  #765  
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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9.jpg   every.jpg   xxx_tumblr_ofumvc8joq1s2ykobo1_1280.jpg  

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  #766  
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. I think the 6th is Gia, not sure though.
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926_1000.jpg   924_1000.jpg   15 (1).jpg  

22.jpg   4.jpg   2_0.jpg  

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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 Sissy caps
Smooth is good.
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8.jpg   1b88b0e5-ae8d-411a-a456-ccca4265fde3.jpg  
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  #768  
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
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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  #769  
Old 05-15-2018
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 Cum eating captions
No such thing as too much cum.
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Picture7.jpg   Picture8.jpg   Picture5.jpg  

Picture4.jpg   Picture2.jpg   Picture6.jpg  

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  #770  
Old 05-16-2018
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Boss Boss is offline
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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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miran squeezing.jpg  
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  #771  
Old 05-16-2018
Boss's Avatar
Boss Boss is offline
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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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' 000 061.JPG  
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  #772  
Old 05-16-2018
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Boss Boss is offline
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Posts: 189
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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' 000 062.jpg  
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  #773  
Old 05-16-2018
Howsoon's Avatar
Howsoon Howsoon is offline
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Default Definitely
What are we waiting for
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438_1000.jpg  
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  #774  
Old 05-16-2018
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Boner Boner is offline
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Boner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant future
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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20775_11.jpg   albj.jpg   tecap1.jpg  

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  #775  
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
[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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  #776  
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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0_01.jpg  
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  #777  
Old 05-17-2018
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Howsoon Howsoon is offline
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Howsoon will become famous soon enough
Default oooo
Well, I'm not going to argue.
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732_1000.jpg  
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  #778  
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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11.jpg   10.jpg   3.jpg  

7.jpg   16.jpg   9.jpg  

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  #779  
Old 05-19-2018
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Boner Boner is offline
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Boner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant futureBoner has a brilliant future
Default
Three of my favorites....Johanna, Jesse, and Kelly Shore!
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  #780  
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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001.jpg   07.jpg   5_001.jpg  

007.jpg   001_00.jpg  
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  #781  
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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tumblr_p0gcu1CeXz1wio8bro1_400.jpg   tumblr_oojxy4RWkm1v0p8eno1_540.jpg  
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  #782  
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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1.jpg   1_000.jpg  
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  #783  
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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CAPS_2095135938.jpg   CAPS_473700758.jpg   z43.jpg  

z44.jpg   z42.jpg   22.jpg  

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  #784  
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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cap-sissy-180410-01.jpg  
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  #785  
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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09.jpg   7.jpg   3 (1).jpg  

24.jpg   05 (1).jpg   10.jpg  

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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 Captions
Some more captions.
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0001_1.jpg   5_0.jpg   02.jpg  

2.jpg   1_0002.jpg   1_5.jpg  

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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 I love sissies
Sissy captions.
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16.jpg   2 (1).jpg   14.jpg  

5.jpg   3 (2).jpg   01_2.jpg  

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  #788  
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.
Attached Thumbnails
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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  #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 Captions
Post more captions.
Attached Thumbnails
01_001.jpg   001_0.jpg  
Last edited by dauls; 05-29-2018 at 06:33 AM.
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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 Rectum cock
I have to admit, I Love a cock in my ass.
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001_5.jpg  
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  #791  
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 aren't smart by design
One of the stupidest captioned pics I have found. Unbelievably stupid.
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YjwRF1526758283.jpg  
Last edited by sailove; 05-27-2018 at 10:49 AM.
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  #792  
Old 05-28-2018
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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
Did my best to weed out the fakes.
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2 (1).jpg   001.jpg   2.jpg  

05.jpg   24.jpg   23.jpg  

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  #793  
Old 05-28-2018
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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
Found a few more caps on my hard drive.
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03.jpg   captions1670.jpg   096_1000.jpg  

12185577_184753471862202_2837346658076287367_o.jpg  
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  #794  
Old 05-28-2018
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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
Hope I don't dupe any.
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  #795  
Old 05-28-2018
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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 Captioned pics
Let's try a few more.
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  #796  
Old 05-28-2018
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sailove sailove is offline
Senior Ladyboy Lover
  
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Location: NEW YORK USA
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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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  #797  
Old 05-29-2018
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sailove sailove is offline
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Location: NEW YORK USA
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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
Sissies always make me hard
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  #798  
Old 05-29-2018
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sailove sailove is offline
Senior Ladyboy Lover
  
Join Date: Jan 2010
Location: NEW YORK USA
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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
Various themes.
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  #799  
Old 06-01-2018
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sailove sailove is offline
Senior Ladyboy Lover
  
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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 Jay
Some Bailey captions.
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  #800  
Old 06-02-2018
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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 Bailey Jay
A couple more Bailey caps.
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