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r/SissyHeaven
135,928 subscribers
A home for anything sissy related including crossdressers, transgenders, traps, ect...

SissyHeaven Moderators

Last updated: 04/28/2024
• Sophia469 added 4 years ago (also mods r/sissypersonals)
• exothrowaway added 3 years ago (also mods r/ForcedFeminization, r/StraightToSissy, r/sissyplace, r/SissyInspiration, r/Feminization, and 16 more...)
• skylab469 added 2 years ago (also mods r/sissypersonals)
• SupremeSissification added 9 months ago (also mods r/bitchsissies, r/sissycaptions, r/sissypersonalscanada, r/SissyInspiration, r/SissysPOV)
• RepostSleuthBot added 7 months ago (also mods r/AquaLewds, r/benzodiazepines, r/CaliforniaSwingers, r/FloridaSwingers, r/Indiana_Swingers, and 787 more...)
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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Preview thumbnail for built to be choked and pounded rough 😫🥺 image
in r/SissyHeaven
built to be choked and pounded rough 😫🥺
Preview thumbnail for built to be choked and fucked rough 😫🥺 image
in r/SissyHeaven
built to be choked and fucked rough 😫🥺
Preview thumbnail for I can’t decide my favourite one image
in r/SissyHeaven
I can’t decide my favourite one
Preview thumbnail for Oops, my panties have fallen down! image
in r/SissyHeaven
Oops, my panties have fallen down!
Preview thumbnail for If I asked you to follow me to the bathroom, would you? image
in r/SissyHeaven
If I asked you to follow me to the bathroom, would you?
Preview thumbnail for failed as a boy so now I’m a good slut 🥺🧎🏼‍♀️ image
in r/SissyHeaven
failed as a boy so now I’m a good slut 🥺🧎🏼‍♀️
Preview thumbnail for Pink and lace are the best. Would you agree? image
in r/SissyHeaven
Pink and lace are the best. Would you agree?
Preview thumbnail for Need more practice to get to the base 🤦‍♂️ image
in r/SissyHeaven
Need more practice to get to the base 🤦‍♂️
Preview thumbnail for Help me become a woman image
in r/SissyHeaven
Help me become a woman
Preview thumbnail for [18] Got compliments on my outfit today and wanted to show some people more😊 image
in r/SissyHeaven
[18] Got compliments on my outfit today and wanted to show some people more😊
Preview thumbnail for Panties night was so much fun image
in r/SissyHeaven
Panties night was so much fun
Preview thumbnail for Super Sissy Sunday 💕 image
in r/SissyHeaven
Super Sissy Sunday 💕
Preview thumbnail for A sissy should always be shaved image
in r/SissyHeaven
A sissy should always be shaved
Preview thumbnail for [18] Just left the gym and super horny. Anybody here can put me in my place? image
in r/SissyHeaven
[18] Just left the gym and super horny. Anybody here can put me in my place?
Preview thumbnail for Fishnet Fun 😘 image
in r/SissyHeaven
Fishnet Fun 😘
Preview thumbnail for Freshly Shaved Friday 🪒 image
in r/SissyHeaven
Freshly Shaved Friday 🪒
Preview thumbnail for Just had to dress up today. 😯 image
in r/SissyHeaven
Just had to dress up today. 😯
Preview thumbnail for Breed Me? image
in r/SissyHeaven
Breed Me?
Preview thumbnail for New outfit❤️ image
in r/SissyHeaven
New outfit❤️
Preview thumbnail for [19] sissy fucktoy begging to be owned and blackmailed image
in r/SissyHeaven
[19] sissy fucktoy begging to be owned and blackmailed
Preview thumbnail for In February this year I put on my first panties, now I look like this. 😳🫦💃 image
in r/SissyHeaven
In February this year I put on my first panties, now I look like this. 😳🫦💃
Preview thumbnail for A little Gallery of showing off some of my skills <3 image
in r/SissyHeaven
A little Gallery of showing off some of my skills <3
Preview thumbnail for Biggest thing I've had in my butt🫨 image
in r/SissyHeaven
Biggest thing I've had in my butt🫨
Preview thumbnail for Hot girl shit only! image
in r/SissyHeaven
Hot girl shit only!
Preview thumbnail for Fitted up image
in r/SissyHeaven
Fitted up