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r/SissyChastity

297,609 subscribers

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

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to r/SissyChastity by SissySuki
15 hours ago
Preview thumbnail for Chastity & Unicorns! image
Chastity & Unicorns!
to r/SissyChastity by betafinn969
2 hours ago
Preview thumbnail for Does this bunnyboi suppose to be in chastity? 🐰🔒 image
Does this bunnyboi suppose to be in chastity? 🐰🔒
to r/SissyChastity by SissySuki
15 hours ago
Preview thumbnail for Spot inspection! image
Spot inspection!
to r/SissyChastity by betafinn969
2 hours ago
Preview thumbnail for Sleeping in this image
Sleeping in this
to r/SissyChastity by SissySuki
15 hours ago
Preview thumbnail for Chastity shrunk my clitty! image
Chastity shrunk my clitty!
to r/SissyChastity by betafinn969
6 days ago
Preview thumbnail for I haven't tried to pull off a landingstrip many times. But I did. It's not so easy to get as I don't have much body hair. 🫢 image
I haven't tried to pull off a landingstrip many times. But I did. It's not so easy to get as I don't have much body hair. 🫢
to r/SissyChastity by betafinn969
6 days ago
Preview thumbnail for I got this cage a week ago. Have used it several times now, feel like it's regressing all of my masculinity I have left. 😦 image
I got this cage a week ago. Have used it several times now, feel like it's regressing all of my masculinity I have left. 😦
to r/SissyChastity by betafinn969
1 week ago
Preview thumbnail for Hi. Closet cd from Finland here. (I'm sorry my chastity doesn't really show here in this picutre )💖🔒 image
Hi. Closet cd from Finland here. (I'm sorry my chastity doesn't really show here in this picutre )💖🔒
in Finland
to r/SissyChastity by betafinn969
1 week ago
Preview thumbnail for I got invited to a party today, also got a new chastity cage in my mail. I skipped the party; stayed home just to try my new chastity cage. Was that the wrong decision? 👀😯 image
I got invited to a party today, also got a new chastity cage in my mail. I skipped the party; stayed home just to try my new chastity cage. Was that the wrong decision? 👀😯
to r/SissyChastity by jakku327
3 weeks ago
Preview thumbnail for Keyholder made me post proof today image
Keyholder made me post proof today
to r/SissyChastity by EvieSissy
4 weeks ago
Preview thumbnail for Day9, finally some relief image
Day9, finally some relief
to r/SissyChastity by EvieSissy
1 month ago
Preview thumbnail for Day 6, keyholder gave me a good hard fuck. Lots of leaking now. image
Day 6, keyholder gave me a good hard fuck. Lots of leaking now.
to r/SissyChastity by EvieSissy
1 month ago
Preview thumbnail for Day 4 in a sexy new negligee image
Day 4 in a sexy new negligee
to r/SissyChastity by max777783
2 weeks ago
Preview thumbnail for Locktober 2024 :) image
Locktober 2024 :)
to r/SissyChastity by EvieSissy
1 month ago
Preview thumbnail for Do you think the boys at the gym will notice? image
Do you think the boys at the gym will notice?
to r/SissyChastity by Lost-Base-4166
1 month ago
Preview thumbnail for Should I keep him locked up the entire month 🤔 image
Should I keep him locked up the entire month 🤔
to r/SissyChastity by EvieSissy
1 month ago
Preview thumbnail for Day 3, keyholder made me watch porn for over an hour last night with my lovense edge in. I was leaking a little by the time it was over. image
Day 3, keyholder made me watch porn for over an hour last night with my lovense edge in. I was leaking a little by the time it was over.
to r/SissyChastity by Viviolettt
2 months ago
Preview thumbnail for This is how I cage my clitty! 🔒 image
This is how I cage my clitty! 🔒
to r/SissyChastity by spookyspookybooty
2 months ago
Preview thumbnail for Nothing more comfortable :3 image
Nothing more comfortable :3
to r/SissyChastity by SatansHoe6
2 months ago
Preview thumbnail for I'm sorry for cumming, but did I do it right? 🥺 image
I'm sorry for cumming, but did I do it right? 🥺
to r/SissyChastity by Cutie1663
3 months ago
Preview thumbnail for GF material? 😇😽 image
GF material? 😇😽
to r/SissyChastity by zeddhunter
3 months ago
Preview thumbnail for Love Riding While Locked Up image
Love Riding While Locked Up
to r/SissyChastity by Lockedaway95
2 months ago
Preview thumbnail for New shiny outfit~ image
New shiny outfit~
to r/SissyChastity by SubbyA1ex
3 months ago
Preview thumbnail for FINALLY upgraded to flat 🤯🥵 image
FINALLY upgraded to flat 🤯🥵
to r/SissyChastity by Cutie1663
4 months ago
Preview thumbnail for Oops, is my skirt too short? 😇😘 image
Oops, is my skirt too short? 😇😘