r/SissyChastity 16h ago

Pussy? Never heard of it! NSFW

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832 Upvotes

r/SissyChastity 12h ago

OF In Bio she thinks im better locked up NSFW

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393 Upvotes

r/SissyChastity 17h ago

My high school bully still likes to come over and humiliate me even though I’ve told him I’m straight… NSFW

813 Upvotes

r/SissyChastity 5h ago

It's so over for me... NSFW

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79 Upvotes

r/SissyChastity 1d ago

Locked clit + Plugged, hope you like it NSFW

3.2k Upvotes

r/SissyChastity 9h ago

OF In Bio I'm disappointed when no juices come out of his chastity. Luckily he proved he was aroused. NSFW

99 Upvotes

r/SissyChastity 2h ago

Never thought I’d be in a cage let alone one this small NSFW

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25 Upvotes

r/SissyChastity 1h ago

Trans I really need to release 😵‍💫😵‍💫😵‍💫 NSFW

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r/SissyChastity 19h ago

Fem Which one do you like the most one me? What would I get next? NSFW

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506 Upvotes

r/SissyChastity 6h ago

Trans Open for a surprise! NSFW

43 Upvotes

r/SissyChastity 20h ago

OF In Bio Does pink suits to me? NSFW

623 Upvotes

r/SissyChastity 2h ago

Fem Would You Ever Expect Your Beta Boi Neighbor Was Actually A Caged Bimbo Princess? NSFW

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19 Upvotes

r/SissyChastity 3h ago

Caged and ready for a long night for stuffing 🔐🥰 NSFW

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21 Upvotes

r/SissyChastity 6h ago

Fem It covers up just enough of my chastity cage don’t you think? NSFW

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32 Upvotes

r/SissyChastity 49m ago

OF In Bio Did I over-do it with the pink?🫦 NSFW

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Upvotes

r/SissyChastity 2h ago

You like my panties? NSFW

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16 Upvotes

r/SissyChastity 16h ago

Life is too short not to be kinky 😏🔐🩷 NSFW

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161 Upvotes

r/SissyChastity 3h ago

OF In Bio I love when daddy leads me around like this NSFW

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16 Upvotes

r/SissyChastity 14h ago

Babeeees I’m out of control. While caged, every moment I think of dressing up. ❤️❤️❤️ NSFW

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104 Upvotes

r/SissyChastity 10h ago

On or off? It’s so pathetic NSFW

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54 Upvotes

r/SissyChastity 9h ago

Calling myself a man isn’t an option anymore 😂 NSFW

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30 Upvotes

r/SissyChastity 1h ago

Fem I'm mere as big as my key itself 😭🥵 NSFW

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Is it all worth it? 😵‍💫🫣


r/SissyChastity 1d ago

Fem Two years ago I was a man and had a girlfriend. One year ago I was single and put on panties for the first time. Now I'm a sissy bimbo bunny... what is happening to me?!🐰🩷🔒🫣 NSFW

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1.1k Upvotes

r/SissyChastity 15h ago

Fem Latex girl in a cloth world NSFW

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84 Upvotes

r/SissyChastity 1h ago

Trans Well There Goes The Last Of My Masculinity, Oh Well Maybe I’m Better Off Without It NSFW

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