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from #thread (https://reddit.com/r/keyholdercaptions/comments/cfy7p0/trying_something_new/) by @SpikesandAsians

Well....sadly this is when my chastity becomes nearly permanent. I know her "friend will work for me.

Becoming a phone sex operator helped me realize that it's okay if I love myself, even with my stomach. Not that I'm not still trying to kickass and lose weight! Please jack off to the thought of cumming on my tits

imgur.com category @TOASTER-KIN

Trying new pants

imgur.com category @Lobo2ffs

Trying to stuff it all in

imgur.com category @pepsi_next

Mom was confused why I wanted to click a picture of her trying on some boots

imgur.com category @[deleted]

First time trying this out. 43M & 38F

imgur.com category @TapirJockey

Sat for 20minutes trying to come up with a clever title but i failed

imgur.com category @IsItBigEnough1

Your girlfriend loves trying new things

gfycat.com category @OCcuck

I was really trying not to get caught

imgur.com category @softtwinky

Trying to suck that thick cock

tumblr.com category @GayGiles

First post, trying things out. Let me know what you think (42)

imgur.com category @Senepicmar

Trying to be Quiet and Fucking my Roommate Friend

gfycat.com category @wezegan

Trying to get that creampie [OC]

gfycat.com category @fun_in_love