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  #801  
Old 06-01-2018
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 Jay

Some Bailey captions.
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1196853090.jpg   339216876.jpg   Sissy_94.jpg  

Sissy_98.jpg   Sissy_100.jpg  
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  #802  
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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Sissy_85.jpg   Sissy_82.jpg  
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  #803  
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 Various captions

And more. remember all post are for entertainment only.
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daddy.jpg   3.jpg   Shemdom20.jpg  

Shemdom14.jpg   ShemDom5.jpg   a5.jpg  

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  #804  
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 Various captions

Upload some more.
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ID72243_1384.jpg   ID72243_1508.jpg   530365630.jpg  

untitled_folder_1561238738.jpg   tumblr_ne04y9vyBo1sk0c6lo1_500.jpg   225978888.jpg  

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  #805  
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 Various captions

A few more to contribute.
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tumblr_o2kaxhwJxz1ul1o7qo1_500.jpg   F_59.jpg   8.jpg  

1_00.jpg  

Last edited by ila; 06-02-2018 at 09:23 PM. Reason: Removed dodgy pic
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  #806  
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 Sissy

Sissies have goals, and for this I am grateful.
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  #807  
Old 06-12-2018
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cumshooter69 is a jewel in the roughcumshooter69 is a jewel in the roughcumshooter69 is a jewel in the rough
Default Hot Ladyboy

I would definitely take a walk on the wild side with her.
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  #808  
Old 06-13-2018
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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

Dirty talk.
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1470195713830.jpg   tgcaption35.jpg   tumblr_mrtn37mEjh1rty243o1_1280.jpg  

tscaption177.jpg   tscaption167.jpg  
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  #809  
Old 06-13-2018
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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

More dirty talk.
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cap06.jpg   Picture1 (1).jpg   0_1803828708.jpg  

shemale_captions_3_006_1000.jpg   Picture3.jpg   Picture1.jpg  

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  #810  
Old 06-13-2018
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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

Bend over baby!
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  #811  
Old 06-13-2018
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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

Reasons to date a sissy.
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sarahsissygirl-rac9e-c707a2.jpg   pbrguy-i0ltd-31f263.jpg   shame85-ntj9f-9ec85b.jpg  

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  #812  
Old 06-13-2018
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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

Sissy girls are so much fun.
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13434838931.jpg   26813122129_a2b8c4b0c6_o.jpg   228_1000_copy.jpg  

F_70.jpg   925_1000.jpg   247748664.jpg  

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  #813  
Old 06-13-2018
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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

Sissy caps.
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a9.jpg   x5.jpg  
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  #814  
Old 06-13-2018
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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

More dirty talk.
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078_1000.jpg   057_1000.jpg   shemale_captions_(10).jpg  

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  #815  
Old 06-15-2018
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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 Captions

Captions with various themes.
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871487863.jpg   tumblr_mjanmffymB1rloispo1_500.jpg   z223.jpg  

remember_me.jpg   a6.jpg  
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  #816  
Old 06-15-2018
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cumshooter69 is a jewel in the roughcumshooter69 is a jewel in the roughcumshooter69 is a jewel in the rough
Default Hot Ladyboy

I'd work her pole anytime
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ladyboy caption 45678.jpg  
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  #817  
Old 06-16-2018
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Howsoon Howsoon is offline
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Howsoon will become famous soon enough
Default Wow

I won't waste a moment!
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684_1000.jpg  
__________________
Amy is the girl for me !!
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  #818  
Old 06-16-2018
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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 Various captions

Varying themes for these caps. The 3rd is one of stranger ones I've found, but I have to give the creator an A+ for imagination.
Attached Thumbnails
17136139.jpg   14808721.jpg   16979234.jpg  

16093834.jpg   14989715.jpg  

Last edited by dauls; 06-24-2018 at 11:03 AM. Reason: ... fake Tg picture removed (see Rule #5).
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  #819  
Old 06-16-2018
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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 Captions

Some captions with dom themes.
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8559865.jpg   10715554.jpg   8559597.jpg  

6325990.jpg  
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  #820  
Old 06-16-2018
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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 Captions

Captions with various themes.
Attached Thumbnails
17156571.jpg   17136147.jpg   lusciousnet_tumblr_mqw3zmf0yy1rty24_1757812729.jpg  

lusciousnet_tumblr_mt1vrhhq1k1rty24_393911423.jpg   70295554ae9194db5c5.jpg   18319327.jpg  

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  #821  
Old 06-21-2018
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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 Captions

Sissies I would love to fuck.
Attached Thumbnails
captions_1555996556960c842305.jpg   captions_1555996556960c6d7bbc.jpg   captions_106513354ba28a62dcec.jpg  

009.jpg   005a.jpg  
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  #822  
Old 06-21-2018
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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 balls

she's very inviting ….
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'          caption TLB  89558_6.jpg  
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  #823  
Old 06-24-2018
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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

Dominating ladies.
Attached Thumbnails
70295554ae9193d4fe9.jpg   70295554ae918d150e2.jpg   70295554ae918e37be3.jpg  

70295554ae918f5554a.jpg   0 (1).jpg  
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  #824  
Old 06-24-2018
Boss's Avatar
Boss Boss is offline
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Posts: 188
Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default Transwomen in charge

He must obey ….
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'        000     061.JPG  
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  #825  
Old 06-24-2018
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Boss Boss is offline
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Posts: 188
Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default Miran

Lovely pain
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miran squeezing.jpg  
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  #826  
Old 06-24-2018
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Boss Boss is offline
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Join Date: Nov 2014
Posts: 188
Boss is just really niceBoss is just really niceBoss is just really niceBoss is just really niceBoss is just really nice
Default too late ...

Just had to take a breath and then she came.
Missed to suck her cum up. All my hard work sucking in vain ...
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Too Late Sucker.jpg  
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  #827  
Old 06-28-2018
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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

3 dom, 1sissy.
Attached Thumbnails
1633891556b823a7d980.jpg   1633891556b8239b2503.jpg   1633891556b822b1b13b.jpg  

tumblr_ow8b0dzw9v1vm5n66o1_500.jpg  
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  #828  
Old 07-01-2018
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cumshooter69 cumshooter69 is offline
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cumshooter69 is a jewel in the roughcumshooter69 is a jewel in the roughcumshooter69 is a jewel in the rough
Default Ladyboy Jasmine

Jasmine is the perfect woman for any man
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JASMINE 0001.jpg   JASMINE 0002.jpg   JASMINE 0003.jpg  

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  #829  
Old 07-01-2018
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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

2 dom caps. The second is Gabriella Silva, a very pretty tranny.
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  #830  
Old 07-23-2018
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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

Yes I am, pretty lady.
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  #831  
Old 08-08-2018
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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 caps I have found lately.
Attached Thumbnails
340_1000.jpg   079_1000.jpg   254_1000.jpg  

tumblr_p8ng64nZbh1wjls1oo1_1280.jpg   358_1000.jpg   357_1000.jpg  

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  #832  
Old 08-22-2018
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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 Sissy

Some sissy caps.
Attached Thumbnails
T-Gurls_022.jpg   CD_24.jpg  

Last edited by dauls; 08-22-2018 at 09:58 AM. Reason: ... fake Tg picture removed (see Rule #5).
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  #833  
Old 08-22-2018
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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 Caption

Well I guess this could happen ?
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TS_44.jpg  

Last edited by sailove; 08-22-2018 at 02:19 PM.
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  #834  
Old 08-23-2018
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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 Pics with a story.

Various captions. Yes Bailey I have.
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16.jpg   al10.jpg   0000001.jpg  

005b.jpg   088uyiyg.jpg  
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  #835  
Old 08-24-2018
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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.

Well the story goes......
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cap1314441264.JPG   11.jpg   cap1949173629.jpg  

0shemcaps_(16).jpg  
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  #836  
Old 09-04-2018
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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

Beautiful ladies.
Attached Thumbnails
9 (1).jpg   z20.jpg   z157.jpg  

z155.jpg   z227.jpg   z225.jpg  

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  #837  
Old 09-04-2018
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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

Always lovely, with an attitude. Sweet.
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2 (1).jpg   22.jpg   001_0.jpg  

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  #838  
Old 09-09-2018
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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

Lovely ladies showing off.
Attached Thumbnails
6 (1).jpg   1 (1).jpg   15.jpg  


Last edited by sailove; 09-09-2018 at 04:39 PM.
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  #839  
Old 01-16-2019
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sailove sailove is offline
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Join Date: Jan 2010
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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 Sexy captions

Some tranny captions.
Attached Thumbnails
tumblr-o63sbssbqp1tufgrpo1-540.jpg   fat-ass-pounding.jpg   untitled-2.jpg  

tra-shiri-bulge.jpg   kitchen-maid.jpg   0009.jpg  

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  #840  
Old 01-16-2019
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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 Tabby caps

Some more caps.
Attached Thumbnails
0012.jpg   rebecca-white-bulge.jpg   rebecca-white-dom.jpg  

arden-bulge.jpg   sara-bulge.jpg   lusciousnet_lusciousnet_16-capset1_1064781982.jpg  

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  #841  
Old 03-12-2019
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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

Girls just want to have fun.
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  #842  
Old 04-11-2019
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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

Some captions I have found.
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  #843  
Old 04-18-2019
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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

Caps with various themes.
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  #844  
Old 09-03-2019
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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 Sexy captions

Bailey caps yummy.
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  #845  
Old 09-04-2019
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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
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Sexy captions.
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  #846  
Old 09-04-2019
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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

Some more sexy caps.
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  #847  
Old 09-04-2019
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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

Even more sexy tranny captions.
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  #848  
Old 11-15-2019
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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 Naughty captions

I love caps.
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  #849  
Old 12-23-2019
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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 caps

So many thoughts
So stimulating
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  #850  
Old 01-03-2020
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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 with various themes.
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