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r/SissyInspiration

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to r/SissyInspiration by betafinn969
2 weeks ago
Preview thumbnail for Got a new chastity cage last week image
Got a new chastity cage last week
to r/SissyInspiration by betafinn969
3 weeks ago
Preview thumbnail for This is my new chastity cage🫦 image
This is my new chastity cage🫦
to r/SissyInspiration by betafinn969
3 weeks ago
Preview thumbnail for Would you know I was a boy, if my little bulge in a chastity cage couldn't be seen? 🫢 image
Would you know I was a boy, if my little bulge in a chastity cage couldn't be seen? 🫢
to r/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for I read about erotic forced feminization stories a year ago.. That was before I started crossdressing. Now I feel like one of those bois I read about. image
I read about erotic forced feminization stories a year ago.. That was before I started crossdressing. Now I feel like one of those bois I read about.
to r/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for I've been inspired by a lot of pics in this subreddit image
I've been inspired by a lot of pics in this subreddit
to r/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for Bought my first dildo a month ago, nervous to actually try one. 😬 But I don't regret it now. 🫢 image
Bought my first dildo a month ago, nervous to actually try one. 😬 But I don't regret it now. 🫢
to r/SissyInspiration by betafinn969
1 month 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/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for I feel a bit needy tonight🫦 image
I feel a bit needy tonight🫦
to r/SissyInspiration by betafinn969
1 month 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/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for Which one do you prefer I gag myself with and why? 😯 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 and why? 😯 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/SissyInspiration by betafinn969
1 month 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. 😶 I guess it's the fear of losing my masculinity and end up becoming a sissy. 😯 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. 😶 I guess it's the fear of losing my masculinity and end up becoming a sissy. 😯
to r/SissyInspiration by betafinn969
1 month 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/SissyInspiration by betafinn969
1 month 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/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for Never thought of myself or wanted to be a sissy, but feeling 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 feeling 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/SissyInspiration by betafinn969
1 month ago
Preview thumbnail for Should I spend the whole weekend in chastity? image
Should I spend the whole weekend in chastity?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Shaved a landing strip😙🩷 image
Shaved a landing strip😙🩷
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Exposing myself for you😯 image
Exposing myself for you😯
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Being more often in a chastity cage lately, makes me buy more feminine things. 😶🩰 image
Being more often in a chastity cage lately, makes me buy more feminine things. 😶🩰
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Always been inspired by a lot of sissies I've seen online. Can I manage someday to inspire someone? image
Always been inspired by a lot of sissies I've seen online. Can I manage someday to inspire someone?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Got my first dildo(s). 🎇👅🍆 Couldn't make up my mind which one to buy, so I bought both. 🤭 Which one do you like more? image
Got my first dildo(s). 🎇👅🍆 Couldn't make up my mind which one to buy, so I bought both. 🤭 Which one do you like more?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for What should I buy next? Any suggestions? image
What should I buy next? Any suggestions?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for How do I look? image
How do I look?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Pussyfree over a year and now I behave like this. Is this how I deserve to look now? image
Pussyfree over a year and now I behave like this. Is this how I deserve to look now?
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Have tried to quit crossdressing to be masculine again, but constantly fail. Am I a fake guy as I've had no girlfriend in over a year? :X image
Have tried to quit crossdressing to be masculine again, but constantly fail. Am I a fake guy as I've had no girlfriend in over a year? :X
to r/SissyInspiration by betafinn969
2 months ago
Preview thumbnail for Guess my age? If you're right, I randomly select one of you and send a closeup pic of my tight hole<3 image
Guess my age? If you're right, I randomly select one of you and send a closeup pic of my tight hole<3