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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
Filtering for posts by u/betafinn969
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to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for I've been crossdressing for 10 days straight. Kind of getting addicted to it. 🫢 image
I've been crossdressing for 10 days straight. Kind of getting addicted to it. 🫢
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for Do you approve of my Saturday outfit? image
Do you approve of my Saturday outfit?
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for Had my first two dildos a month now. Do you want to guess which one is my favorite? 🥰 Left or Right. image
Had my first two dildos a month now. Do you want to guess which one is my favorite? 🥰 Left or Right.
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for It feels like femininity is taking over my failed boi body... 💅💄🩰 image
It feels like femininity is taking over my failed boi body... 💅💄🩰
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for Three days in a row playing with this toy image
Three days in a row playing with this toy
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for I'm glad I found the courage to buy a dildo a month ago💋 image
I'm glad I found the courage to buy a dildo a month ago💋
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for Got my first dildos a month ago, never thought it would feel this good🫢🫦💥 image
Got my first dildos a month ago, never thought it would feel this good🫢🫦💥
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for I have started to get a feeling that I need to expose myself online more. image
I have started to get a feeling that I need to expose myself online more.
to r/AmateurSissy by betafinn969
3 weeks ago
Preview thumbnail for Which one do you prefer I gag myself with? 😯 1) Mouth gag 2) Cock gag 3) Ball gag? 🥵 PS: I've been using my nipple suction cups now couple of weeks. They make my nipples so sensitive🫦 image
Which one do you prefer I gag myself with? 😯 1) Mouth gag 2) Cock gag 3) Ball gag? 🥵 PS: I've been using my nipple suction cups now couple of weeks. They make my nipples so sensitive🫦
to r/AmateurSissy by betafinn969
3 weeks 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 weeks ago
Preview thumbnail for Does anyone like femboi tits? 🫢 image
Does anyone like femboi tits? 🫢
to r/AmateurSissy by betafinn969
3 weeks 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 betafinn969
3 weeks 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 betafinn969
3 weeks 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 betafinn969
3 weeks 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 betafinn969
3 weeks ago
Preview thumbnail for My masculinity keeps failing me image
My masculinity keeps failing me
to r/AmateurSissy by betafinn969
1 month 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. 😧
to r/AmateurSissy by betafinn969
1 month ago
Preview thumbnail for This is my first picture playing with a dildo. 😶 Do you like it? image
This is my first picture playing with a dildo. 😶 Do you like it?