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r/sissydressing

216,575 subscribers

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

Filtering for posts by u/user123lols
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to r/sissydressing by user123lols
4 months ago
Preview thumbnail for I love this outfit image
I love this outfit
to r/sissydressing by user123lols
4 months ago
Preview thumbnail for Let’s go to the beach image
Let’s go to the beach
to r/sissydressing by user123lols
6 months ago
Preview thumbnail for They wouldn’t let me play with Barbie’s so I became Barbie image
They wouldn’t let me play with Barbie’s so I became Barbie
to r/sissydressing by user123lols
6 months ago
Preview thumbnail for I’ve finally got my hands on some vintage style lingerie image
I’ve finally got my hands on some vintage style lingerie
to r/sissydressing by user123lols
6 months ago
Preview thumbnail for Baby I just wanna wear a skirt for you image
Baby I just wanna wear a skirt for you
to r/sissydressing by user123lols
7 months ago
Preview thumbnail for Say “yes mommy” if you missed me image
Say “yes mommy” if you missed me
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for Feeling pretty in pink image
Feeling pretty in pink
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for If you couldn’t tell blue is my favorite color. What’s yours? image
If you couldn’t tell blue is my favorite color. What’s yours?
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for Pink wig, pink lace, a perfect match image
Pink wig, pink lace, a perfect match
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for Be honest…. Would you? image
Be honest…. Would you?
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for This might be my favorite lingerie set ever image
This might be my favorite lingerie set ever
to r/sissydressing by user123lols
8 months ago
Preview thumbnail for Eager to be touched by a real man image
Eager to be touched by a real man
to r/sissydressing by user123lols
9 months ago
Preview thumbnail for The perfect bra does exist image
The perfect bra does exist
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for Slutty Secretary is definitely my vibe image
Slutty Secretary is definitely my vibe
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for Hotter than your ex with a little bit more to play with. Breed me? image
Hotter than your ex with a little bit more to play with. Breed me?
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for The holidays may be over but my presence is still a gift. Would you unwrap me? image
The holidays may be over but my presence is still a gift. Would you unwrap me?
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I just love wearing red image
I just love wearing red
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I LOVE wearing lingerie image
I LOVE wearing lingerie
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I think i have mastered the Secretary look image
I think i have mastered the Secretary look
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I am OBSESSED with this set image
I am OBSESSED with this set
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for Good morning lovers image
Good morning lovers
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I love wearing lingerie image
I love wearing lingerie
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for I will forever be a button up blouse and shirt skirt girly image
I will forever be a button up blouse and shirt skirt girly
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for There’s just something about a skirt and a wig that feels incredible image
There’s just something about a skirt and a wig that feels incredible
to r/sissydressing by user123lols
10 months ago
Preview thumbnail for Would you rather play with the front or the back? image
Would you rather play with the front or the back?