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r/AmateurSissy

15,549 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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Sissy OC
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to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Just lounging image
Just lounging
to r/AmateurSissy by uklingerielover
3 months ago
Preview thumbnail for All dressed up ready for bed who wants to join me image
All dressed up ready for bed who wants to join me
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for 7 months a closet cd now, and it feels like time flies by. Been pussyfree over a year now and hoped to quit crossdressing, be a man again and find a gf. But it feels like I'm going further and further away from that. 😶 image
7 months a closet cd now, and it feels like time flies by. Been pussyfree over a year now and hoped to quit crossdressing, be a man again and find a gf. But it feels like I'm going further and further away from that. 😶
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for Does anyone like femboi tits? 🫢 image
Does anyone like femboi tits? 🫢
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Feel right in white image
Feel right in white
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for No willpower left today to act manly or masculine, going to be dressed as a girl today until I go to sleep.👄👚💄🩷 What kind of pictures do you want to see of me? image
No willpower left today to act manly or masculine, going to be dressed as a girl today until I go to sleep.👄👚💄🩷 What kind of pictures do you want to see of me?
to r/AmateurSissy by uklingerielover
3 months ago
Preview thumbnail for Happy Friday everyone can tell am already excited image
Happy Friday everyone can tell am already excited
to r/AmateurSissy by Fuktoiii
4 months ago
Preview thumbnail for Almost got caught by my parents today! image
Almost got caught by my parents today!
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for I edged a few times before locking myself up.🫦 I'm a very sexual person so I masturbate almost every day.😨 So it will be very difficult for me today.😣 But asking you, am I allowed to cum tomorrow at least? Or should I stay locked longer? Please consider that I haven't really tried this before.😵‍ image
I edged a few times before locking myself up.🫦 I'm a very sexual person so I masturbate almost every day.😨 So it will be very difficult for me today.😣 But asking you, am I allowed to cum tomorrow at least? Or should I stay locked longer? Please consider that I haven't really tried this before.😵‍
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Stay plugged image
Stay plugged
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for This is the first time I post a pic of my dick on the internet. 🫣 I have feared that it's one of the reason I became a closet crossdresser (I'm sorry I'm small). But also because I'm petite and can't compete with real dominant men. 😨 image
This is the first time I post a pic of my dick on the internet. 🫣 I have feared that it's one of the reason I became a closet crossdresser (I'm sorry I'm small). But also because I'm petite and can't compete with real dominant men. 😨
to r/AmateurSissy by Imaginary_Lion_5828
3 months ago
Preview thumbnail for yes or no 🥵🤤😈🔥 image
yes or no 🥵🤤😈🔥
to r/AmateurSissy by OwnSwimming1993
3 months ago
Preview thumbnail for My goal is to build a following on here and then make content by being fucked by my followers all round the UK! Male/Female/Dom's/Trans everyone! image
My goal is to build a following on here and then make content by being fucked by my followers all round the UK! Male/Female/Dom's/Trans everyone!
to r/AmateurSissy by TransportationTime18
4 months ago
Preview thumbnail for Bris femboy image
Bris femboy
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for Never thought of myself or wanted to be a sissy, but feelings very addicted to dressing and thinking about men lately.😯 Many have asked for my name, but I don't have any girly name. Posting this to ask your opinion what kind of name would suit me? 🫢🫣 image
Never thought of myself or wanted to be a sissy, but feelings very addicted to dressing and thinking about men lately.😯 Many have asked for my name, but I don't have any girly name. Posting this to ask your opinion what kind of name would suit me? 🫢🫣
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for I see you peeking image
I see you peeking
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Back side view image
Back side view
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Can I wrap these around you? image
Can I wrap these around you?
to r/AmateurSissy by uklingerielover
3 months ago
Preview thumbnail for Happy Saturday what's everyone doing today image
Happy Saturday what's everyone doing today
to r/AmateurSissy by betafinn969
3 months ago
Preview thumbnail for My masculinity keeps failing me image
My masculinity keeps failing me
to r/AmateurSissy by xplosive_az
4 months ago
Preview thumbnail for Can I lay with you? image
Can I lay with you?
to r/AmateurSissy by candyapplecrisp
4 months ago
35[M4MF] Friends
M4MF
to r/AmateurSissy by uklingerielover
3 months ago
Preview thumbnail for Fuck me it's friday image
Fuck me it's friday
to r/AmateurSissy by Key-Nobody-1001
4 months ago
Preview thumbnail for What a sissy does when she’s home alone image
What a sissy does when she’s home alone
to r/AmateurSissy by betafinn969
4 months ago
Preview thumbnail for Got myself my first vibrator. 👀 Always been a man, but putting on a wig and taking this picture, and seeing myself... it feels like a lie. 😧 image
Got myself my first vibrator. 👀 Always been a man, but putting on a wig and taking this picture, and seeing myself... it feels like a lie. 😧