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r/sissydressing

218,862 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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to r/sissydressing by oilgains
5 days ago
Preview thumbnail for Little butts deserve luv too šŸ’• image
Little butts deserve luv too šŸ’•
to r/sissydressing by jessicaskyheel
2 weeks ago
Preview thumbnail for In my selfmade catsuit image
In my selfmade catsuit
to r/sissydressing by Lanky_Incident_2865
1 week ago
Preview thumbnail for If I was your girlfriend would you let me go out dressed like this?šŸ˜ image
If I was your girlfriend would you let me go out dressed like this?šŸ˜
to r/sissydressing by Ok_Mall_5311
2 weeks ago
Preview thumbnail for just a little clitty edging image
just a little clitty edging
to r/sissydressing by Switch_us
2 weeks ago
Preview thumbnail for Love my short dresses and heels šŸ„° image
Love my short dresses and heels šŸ„°
to r/sissydressing by betafinn969
2 weeks ago
Preview thumbnail for Whiteboi here watching too much BBC hypno latelyā™ ļøŽ image
Whiteboi here watching too much BBC hypno latelyā™ ļøŽ
to r/sissydressing by cdslutmariee
1 week ago
Preview thumbnail for Leggings looking good image
Leggings looking good
to r/sissydressing by jessicaskyheel
2 weeks ago
Preview thumbnail for Do you like my pigtails? image
Do you like my pigtails?
to r/sissydressing by SissyCatie1994
1 week ago
Preview thumbnail for Just got a new outfit image
Just got a new outfit
to r/sissydressing by DescriptionPhysical5
1 week ago
Preview thumbnail for What would you do to be my first cock image
What would you do to be my first cock
to r/sissydressing by ThongBoiJess
1 week ago
Preview thumbnail for What happenedā€¦? I swear hypno doesnā€™t work! image
What happenedā€¦? I swear hypno doesnā€™t work!
to r/sissydressing by Starscreamnight14
1 week ago
Motivationā€¦who wants these boots wrapped around there neck
to r/sissydressing by jessicaheavents
1 week ago
Preview thumbnail for don't argue. everyone can come in image
don't argue. everyone can come in
to r/sissydressing by auroradott06
1 week ago
Preview thumbnail for The fact the turkey was stuffed this thanksgiving but I wasnā€™t is so unfair! šŸ˜« image
The fact the turkey was stuffed this thanksgiving but I wasnā€™t is so unfair! šŸ˜«
in Turkey
to r/sissydressing by jessicaskyheel
2 weeks ago
Preview thumbnail for I love Blowjob image
I love Blowjob
to r/sissydressing by Siss_Sophia
2 weeks ago
Preview thumbnail for Grateful for this body image
Grateful for this body
to r/sissydressing by Kaylasweets25
2 weeks ago
Preview thumbnail for Howā€™s my fit? image
Howā€™s my fit?
to r/sissydressing by Sissy4BBCuk
2 weeks ago
Preview thumbnail for Lingerie is top tier sexy šŸ˜ˆ image
Lingerie is top tier sexy šŸ˜ˆ
to r/sissydressing by sissy-fantasyyy
2 weeks ago
Preview thumbnail for My gf left me because she was jealous I looked sexier!!! image
My gf left me because she was jealous I looked sexier!!!
to r/sissydressing by sissyfag4579
3 weeks ago
Preview thumbnail for New panties image
New panties
to r/sissydressing by sissyfag4579
3 weeks ago
Preview thumbnail for A good sissy will wear bra and panties image
A good sissy will wear bra and panties
to r/sissydressing by Sensitive_Bee5382
2 weeks ago
Preview thumbnail for šŸ™ˆ image
šŸ™ˆ
to r/sissydressing by Siss_Sophia
3 weeks ago
Preview thumbnail for Do I look like an angel image
Do I look like an angel
to r/sissydressing by OliviasSecrets
6 days ago
Preview thumbnail for My ass sweats all day. I guess Iā€™m in heat. image
My ass sweats all day. I guess Iā€™m in heat.
to r/sissydressing by Cute-Repeat-3270
2 weeks ago
Preview thumbnail for Finally back in some pink panties and a bra. I feel so good šŸ˜ image
Finally back in some pink panties and a bra. I feel so good šŸ˜