Sissy Chastity: Sissies and TGirls in Chastity

r/SissyChastity • u/SissyLexiLela • Nov 05 '22

My cage caused me to totally accept my fate as an anal fucktoy. Would you use me like one, or would you rather bend over alongside me? NSFW

20.0k Upvotes

r/SissyChastity • u/AngelAvaa • Feb 17 '26

Trans first time cumming whilst caged.. i hope youre proud of me😵‍💫 NSFW

16.6k Upvotes

r/SissyChastity • u/SissyLexiLela • Aug 26 '25

Trans I'm so far gone, I'm not even embarrassed at the thought that everyone knows I'm locked tight with no trace of my former masculinity remaining NSFW

16.4k Upvotes

r/SissyChastity • u/Slygirl997 • Dec 16 '23

Cumming in chastity NSFW

13.8k Upvotes

r/SissyChastity • u/Sissyfem_Jenny • Oct 15 '22

First sissygasm thanks to chastity and locktober 🥰 NSFW

12.8k Upvotes

r/SissyChastity • u/Skylar737 • Mar 12 '23

💕my most intense chastity setup ever💕 NSFW

12.0k Upvotes

r/SissyChastity • u/tsevelyntumbles • Aug 30 '22

PSA: an unlocked sissy maid will always take advantage of a locked one- do your part and be sure that BOTH their cages are secure before you leave for the day ;) NSFW

11.5k Upvotes

r/SissyChastity • u/Technical-Tree237 • Jul 17 '25

Fem Amazing sissygasm compilation.Enjoy! NSFW

9.4k Upvotes

r/SissyChastity • u/nano_nano_ • Mar 08 '22

Lift my legs over your shoulders and make love to me ^-^ NSFW

9.4k Upvotes

r/SissyChastity • u/SissyLexiLela • Oct 23 '22

Chastity reprogrammed my brain. My orgasm is irrelevant. Making men shoot their loads makes me feel better than stroking ever did! NSFW

9.3k Upvotes

r/SissyChastity • u/1amsrry • Nov 06 '25

Going crazy 😵‍💫 NSFW

9.1k Upvotes

r/SissyChastity • u/W0LLIP • May 24 '23

get ready with me! caged and plugged edition 💕 NSFW

8.9k Upvotes

r/SissyChastity • u/MySithLady • Jul 07 '25

Highlights! 24/7 means 24/7! NSFW

8.8k Upvotes

r/SissyChastity • u/Psychokitty666777 • Feb 17 '25

Gotta Work your way from the Bottom🔒 NSFW

8.3k Upvotes

r/SissyChastity • u/Ok-Profession2439 • Oct 16 '25

OF In Bio Locktober 8th -15th NSFW

8.2k Upvotes

r/SissyChastity • u/haselynne • Nov 26 '23

OF In Bio i almost came in my flat cage from anal, but it doesn't count as failing NNN right? NSFW

8.1k Upvotes

r/SissyChastity • u/OpenAccountt • Nov 14 '23

That Cage Is Going Nowhere Now 😳😳 NSFW

8.0k Upvotes

r/SissyChastity • u/smoothbottom1976 • Aug 25 '24

Requested Chastity feminizer belt video demo. NSFW

7.9k Upvotes

r/SissyChastity • u/SissyStephaniex • Apr 24 '21

I've passed the 300 days in chastity 🙈 NSFW

7.7k Upvotes

r/SissyChastity • u/sissicinema • Mar 11 '25

I lasted 70 straight days in chastity until today... NSFW

7.4k Upvotes

r/SissyChastity • u/TooManyPeachess • Jun 10 '25

Highlights! Orchiectomy and flat cage. I guess I’m a role model for yall? NSFW

7.4k Upvotes

r/SissyChastity • u/BoringKate • Jan 03 '24

Hard to beleive I was ever a boy! NSFW

7.4k Upvotes

r/SissyChastity • u/Psychokitty666777 • Aug 14 '25

Raver girl always have tiny Cocks💕 NSFW

7.3k Upvotes

r/SissyChastity • u/AngelAvaa • Feb 10 '26

Trans my roommate filmed then sent me thiswithout me noticing.. idk what to do😵‍💫 NSFW

6.8k Upvotes

r/SissyChastity • u/cageslutjenny • Oct 02 '22

Locking my inverted cage on 🖤 NSFW

6.8k Upvotes