How long have you known you were born to be a sissy, user?

Asshole pics

Oh that's about the same as mine then, not too small.
>It just looks so much better when it's caged
I'm not a huge fan of chastity per se, but those pink cages sure look cute.

It's a woman? Welp.

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I'm really desperate to have one. I feel like once I finally do there's no coming back

yea its from a video called ultra violence, which is surprisingly tame these days.

xvideos.com/video1574880/ultraviolence_sex

I've only cum using my butt for like an entire year

The porn I consume has slowly been getting gayer and more sissy focused for a long time, but I think it was 3 years ago that I realized I want to be a sissy

I want to be a sissy but I feel as if I'm too manly for it. I'm 6 feet and really hairy.

I've experimented with butt stuff since I was teen, but only recently (~1 year) took the dive into buying toys and cages and girl shit.

Feels great man.

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Usually when I get around the week and a half mark of wearing chastity and not cumming I get weak and jerk off. It seems like it doesn't really matter how much anal training I do, as long as I keep masturbating like a boy I'm not going to sissygasm

Ahhh I see, thanks user. Shame.

Fucking A. You posted in some of the other threads, I saved ^9

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