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r/sissyguide

71,618 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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Challenge Me Feminized Reveal Unapproved Source Plugged Caged Sissy Slut Ass Up, Face Down! Open DMs Sissy Caption watch Femboy Bimbo 👄
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to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Looking for someone femme that motivates me to go deeper down the sissy rabbit hole by positive rationalization. image
Looking for someone femme that motivates me to go deeper down the sissy rabbit hole by positive rationalization.
Challenge Me
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This sissy needs some sissy/trans pee play inspiration image
This sissy needs some sissy/trans pee play inspiration
Challenge Me
to r/sissyguide by Excellent-Policy4819
8 months ago
Preview thumbnail for new outfit what do you think?? image
new outfit what do you think??
Challenge Me
to r/sissyguide by Excellent-Policy4819
8 months ago
Preview thumbnail for student needs a teacher image
student needs a teacher
Challenge Me
to r/sissyguide by TommYWSC
8 months ago
Preview thumbnail for Is anyone hungry🍰 image
Is anyone hungry🍰
Challenge Me
to r/sissyguide by nehirgirl
11 months ago
Preview thumbnail for Am I a College Sorority Girl image
Am I a College Sorority Girl
Challenge Me
to r/sissyguide by tryingitout2023
1 year ago
Preview thumbnail for Wish I had the courage to wear this to the adult theater. 😈 image
Wish I had the courage to wear this to the adult theater. 😈
Challenge Me
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for I want to be your lockscreen! image
I want to be your lockscreen!
Challenge Me
to r/sissyguide by Jennigirl1996
1 year ago
Preview thumbnail for day 22, loving every second. Would love to bemade to sissygasm and eat it image
day 22, loving every second. Would love to bemade to sissygasm and eat it
Challenge Me
to r/sissyguide by Smart_Possible_8807
1 year ago
Preview thumbnail for Send my slutty pawg ass degrading tasks… With an ass like this I was born to serve. image
Send my slutty pawg ass degrading tasks… With an ass like this I was born to serve.
Challenge Me
to r/sissyguide by Jennigirl1996
1 year ago
Preview thumbnail for I'm new to this, day 4 so far :) looking to step up my game. I've never Sissygasmed before or eaten my own cum, how do i make myself do it? it turns me on but i always chicken out; hope the cage helps. Any suggestions? I want to be a good slave image
I'm new to this, day 4 so far :) looking to step up my game. I've never Sissygasmed before or eaten my own cum, how do i make myself do it? it turns me on but i always chicken out; hope the cage helps. Any suggestions? I want to be a good slave
Challenge Me
to r/sissyguide by beertasterb
1 year ago
Preview thumbnail for Don’t be gentle image
Don’t be gentle
Challenge Me
to r/sissyguide by beertasterb
1 year ago
Preview thumbnail for Make me regret this image
Make me regret this
Challenge Me
to r/sissyguide by beertasterb
10 months ago
Preview thumbnail for Looking for any roulettes or pics image
Looking for any roulettes or pics
Challenge Me
to r/sissyguide by beertasterb
1 year ago
Preview thumbnail for Send me anything image
Send me anything
Challenge Me
to r/sissyguide by paigeeebabyyy
9 months ago
Preview thumbnail for i’m so hornyyyy, help me out? dms always open ;) image
i’m so hornyyyy, help me out? dms always open ;)
Challenge Me
to r/sissyguide by TightKinkyBoy
1 year ago
Preview thumbnail for Show me how to be a good sissy image
Show me how to be a good sissy
Challenge Me
to r/sissyguide by hothot_stuff
1 year ago
Preview thumbnail for I'm ready image
I'm ready
Challenge Me
to r/sissyguide by tripleD127
1 month ago
Preview thumbnail for let's have fun 😋 image
let's have fun 😋
Challenge Me
to r/sissyguide by XanderMax125
1 year ago
Preview thumbnail for first time posting like this. send me something good image
first time posting like this. send me something good
Challenge Me
to r/sissyguide by fdfvjhff
4 months ago
Preview thumbnail for Please image
Please
Challenge Me
to r/sissyguide by suffering_adjacent
11 months ago
Preview thumbnail for I really want to not be a virgin anymore,no limits image
I really want to not be a virgin anymore,no limits
Challenge Me