Sissy Captions

r/sissycaptions • u/TSposter • Mar 01 '23

Sissy Caption Sissy School Progress NSFW

30.2k Upvotes

r/sissycaptions • u/saragreyxoxo • Dec 21 '20

Hall of Fame Post Sissy Streamer NSFW

27.3k Upvotes

r/sissycaptions • u/MichelleVenus97 • Dec 18 '23

Sissy Caption “forced” NSFW

23.3k Upvotes

r/sissycaptions • u/random_sissy_sub • Aug 19 '21

Female's POV The VR Sissy Test Part1 NSFW

22.3k Upvotes

r/sissycaptions • u/SissyLexiLela • Aug 05 '22

Sissy Caption This is your sign to get out there and SUCK COCK! NSFW

21.1k Upvotes

r/sissycaptions • u/[deleted] • Nov 30 '22

Sissy Caption Good thing I said no homo😮‍💨 NSFW

19.8k Upvotes

r/sissycaptions • u/eat-my-chorizo • Jul 20 '21

Chastity All it took to break your brain was 5 weeks of chastity NSFW

18.8k Upvotes

r/sissycaptions • u/random_sissy_sub • Jul 02 '20

Hall of Fame Post Would you get it right? NSFW

18.5k Upvotes

r/sissycaptions • u/LoveableScrivener • Sep 14 '20

Hall of Fame Post Bathtime Treat NSFW

17.1k Upvotes

r/sissycaptions • u/saragreyxoxo • Jan 13 '21

Doesn't looks gay to me, what do you think? NSFW

17.0k Upvotes

r/sissycaptions • u/W0LLIP • May 25 '23

Chastity Caption get ready with me! caged and plugged edition 💕 NSFW

16.3k Upvotes

r/sissycaptions • u/ComfortableOk652 • Mar 16 '25

Sissy Caption I choose A NSFW

15.2k Upvotes

r/sissycaptions • u/KingKaneWood • Oct 14 '23

Sissy Caption Right Sissy! NSFW

15.0k Upvotes

r/sissycaptions • u/nwc4676 • Jul 26 '21

Sissy Caption Cock Changed Your Life NSFW

14.4k Upvotes

r/sissycaptions • u/TheQrious1 • Nov 07 '22

Sissy Caption If only you knew earlier... NSFW

14.2k Upvotes

r/sissycaptions • u/random_sissy_sub • Aug 20 '21

Sissy Caption The VR Sissy Test Part2 NSFW

13.8k Upvotes

r/sissycaptions • u/[deleted] • Dec 18 '24

Sissy Caption Is it true? NSFW

13.0k Upvotes

r/sissycaptions • u/Sissy-Fiction • Mar 07 '21

Choosing to go sissy full-time was a big decision, but so far, you have no regrets! The only real problem you have with it is that you're super horny 24/7... But a big, thick dick to ride seems to fix that too NSFW

12.7k Upvotes

r/sissycaptions • u/MichelleVenus97 • Dec 15 '23

Sissy Caption Its never just a joke... NSFW

12.6k Upvotes

r/sissycaptions • u/[deleted] • Jun 22 '21

Sissy Caption How I spent the Lockdown NSFW

12.3k Upvotes

r/sissycaptions • u/Blackwidow0619 • Nov 10 '23

Sissy Caption My friend took advantage of sharing a hotel room with me NSFW

12.2k Upvotes

r/sissycaptions • u/sissy-slut-emily • Dec 01 '24

Sissy Caption say it sissy NSFW

11.9k Upvotes

r/sissycaptions • u/ComfortableOk652 • Apr 27 '25

Sissy Caption Chained to his manhood NSFW

11.9k Upvotes

r/sissycaptions • u/OpenAccountt • Oct 29 '23

Sissy Caption Are You Going Balls Deep 🤤🤤 NSFW

11.6k Upvotes

r/sissycaptions • u/ComfortableOk652 • Oct 12 '25

Sissy Caption Your choice sissy NSFW

11.5k Upvotes