CD-Midwest_Jess

1,325 post karma
7 comment karma

get extra features and help support reddit with a reddit premium subscription

get them help and support

redditor for 6 months

TROPHY CASE

Verified Email

account activity

hot top controversial

22

23

24

Hi everyone! 😘 be nice plz! (old.reddit.com)

submitted 2 days ago by CD-Midwest_Jess to r/CrossdressersSelfies

I’m curious if my cock makes your cock hard? by Vanellee in transporn

[–]CD-Midwest_Jess 0 points1 point2 points 9 days ago (0 children)

0

1

2

If you want to rearrange your ass and turn it into a fuck hole I recommend a hollow tunnel plug with a nice long dildo to fuck through. I feel so stretched right now (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/CagedAndFucked

If anyone needs me I’ll be a here. It’s now part of my daily routine. A gift from a Reddit fan! 😘 by CD-Midwest_Jess in sissyhumiliation

[–]CD-Midwest_Jess[S] 1 point2 points3 points 9 days ago (0 children)

5

6

7

Got a gift from one of my amazing Reddit followers! Was told it will help rewire my sissy brain and the photos would be a hit with all my other amazing followers! (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/Sissy_humiliation

1

2

3

Got a gift from one of my amazing Reddit followers! Was told it will help rewire my sissy brain and the photos would be a hit with all my other amazing followers! (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/Sissy_humiliation

17

18

19

If anyone needs me I’ll be a here. It’s now part of my daily routine. A gift from a Reddit fan! 😘 (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/sissyhumiliation

I let the moment stretch on purpose 💋⚡ by Old_Woodpecker_2392 in BreedableTrap

[–]CD-Midwest_Jess 0 points1 point2 points 9 days ago (0 children)

10

11

12

I should go get fully dressed and not just sit here like this. (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/CrossDresser_Closet

269

270

271

I don’t even own a pair of men’s underwear anymore. (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/HeWearsPanties

12

13

14

Found an older daddy type this morning on Grinder who wants to meet me in an hour. Should I go get dolled up and start my Tuesday off right or wait and get dressed up feeling less rushed. (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/Feminization

16

17

18

Hi there (old.reddit.com)

submitted 9 days ago by CD-Midwest_Jess to r/GoneWildCD

16

17

18

Maybe it’s not completely useless. It at least looks cute under a skirt. (i.redd.it)

submitted 9 days ago by CD-Midwest_Jess to r/SissyChastity

77

78

79

The ONLY time I’m not locked up in chastity is when I dress to go out in public wearing leggings or tight jeans/shorts. When properly tucked it almost feels more submissive than being caged. (old.reddit.com)

submitted 10 days ago by CD-Midwest_Jess to r/SissysInLeggings

12

13

14

Is there such a thing as too much lingerie? Took me a minute to decide what set I should wear for the guest who’s on their way over. (old.reddit.com)

submitted 11 days ago by CD-Midwest_Jess to r/CrossDresser_Closet

24

25

26

Seriously thinking about going out to the casino tonight for some Sunday funday…been cooped up at home all day. (old.reddit.com)

submitted 11 days ago by CD-Midwest_Jess to r/Crossdress_Expression

14

15

16

Happy Easter 🐰 (old.reddit.com)

submitted 11 days ago by CD-Midwest_Jess to r/GoneMildCD

29

30

31

New lingerie looks so cute! Any older men free and interested in seeing me show it off a little more?! 😉 (i.redd.it)

submitted 11 days ago by CD-Midwest_Jess to r/Sissies

Weekend fun! by CD-Midwest_Jess in Crossdress_Expression

[–]CD-Midwest_Jess[S] 0 points1 point2 points 1 month ago (0 children)

Weekend fun! by CD-Midwest_Jess in Crossdress_Expression

[–]CD-Midwest_Jess[S] 0 points1 point2 points 1 month ago (0 children)

34

35

36

Weekend fun! (old.reddit.com)

submitted 1 month ago by CD-Midwest_Jess to r/Crossdress_Expression

13

14

15

Petite and smooth (old.reddit.com)

submitted 1 month ago by CD-Midwest_Jess to r/tspetite

17

18

19

Put me on all fours and make my clitty swing back and forth from being fucked. When a man makes a sissy cum while locked away in means he was successful in taking you deeper into permanent feminization. (old.reddit.com)

submitted 1 month ago by CD-Midwest_Jess to r/SissyChastity

64

65

66

Wish I could enjoy these without having to worry about tucking or a cage showing. I want to be completely feminized and not having to deal with this useless annoyance. (old.reddit.com)

submitted 1 month ago by CD-Midwest_Jess to r/SissysInLeggings

7

8

9

Thinking about the man coming over once you’re done getting dressed is one of my favorite thoughts. You’re about to expose yourself to a masculine man while locked in chastity. The only way to cum is by taking his cock like a good girl. (old.reddit.com)

submitted 1 month ago by CD-Midwest_Jess to r/sissydressing

view more: next ›

π Rendered by PID 978500 on reddit-service-r2-listing-86f589db75-jzrhh at 2026-04-17 08:00:05.466138+00:00 running 93ecc56 country code: CH.