r/sissycaptions

476,130 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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Epilepsy Warning Sissy Caption Memes (Not Caption) Animated/Toon/Hentai Good Sissy Keeper of Captions Pansexual Faggot Caption Bad Sissy Race Play Caption Chastity Caption Obvious Cis-female Race Play Bisexual Incest Games (Not Caption) Incest Caption Faggot/Fag Slur in Caption Transgender Request to be Captioned Faggot Faggot Quality Post Straight Caption Request Hall of Fame Post Bottom/Taker POV Low Effort Caption Chastity Sissygasm view more

Showing posts with Chastity Caption flair to r/sissycaptions

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to r/sissycaptions by Secret_Sissy11

2 weeks ago

302

Be honest… If u could look like her would u do it?!

Chastity Caption

Posted by Secret_Sissy11

Account Strength

50%

Account Age

1 month

Verified Email

Yes

Verified Flair

Total Karma

1,677

Link Karma

1,578

Comment Karma

Profile updated: 3 days ago

to r/sissycaptions

3 weeks ago

to r/sissycaptions by Spreadoutlikebutter

3 weeks ago

329

Squirt like a girl

Chastity Caption

Posted by Spreadoutlikebutter

Account Strength

80%

Account Age

7 months

Verified Email

Yes

Verified Flair

Total Karma

6,973

Link Karma

5,480

Comment Karma

1,493

Profile updated: 4 days ago

to r/sissycaptions

4 weeks ago

to r/sissycaptions by gooner4bootsluts

1 week ago

222

Look at what porn and hypno have turned me into! 😈🤤

Chastity Caption

Posted by gooner4bootsluts

Account Strength

70%

Account Age

3 years

Verified Email

Verified Flair

Total Karma

8,439

Link Karma

8,030

Comment Karma

394

Profile updated: 2 days ago

to r/sissycaptions

4 weeks ago

to r/sissycaptions by fapInteractive

1 week ago

260

A good fucking

Chastity Caption

Posted by fapInteractive

Account Strength

100%

Account Age

4 years

Verified Email

Yes

Verified Flair

Total Karma

29,258

Link Karma

29,052

Comment Karma

153

Profile updated: 2 days ago

to r/sissycaptions

2 months ago

to r/sissycaptions by JessicaSissyCaptions

1 week ago

294

Sissy's favorite piece of jewelry💓

Chastity Caption

Posted by JessicaSissyCaptions

Account Strength

80%

Account Age

4 months

Verified Email

Yes

Verified Flair

Total Karma

7,360

Link Karma

7,346

Comment Karma

Profile updated: 18 hours ago

to r/sissycaptions

2 months ago

to r/sissycaptions by Mastersissytrainer

2 months ago

137

Are You Ready?

Chastity Caption

Posted by Mastersissytrainer

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

9,697

Link Karma

9,255

Comment Karma

427

Profile updated: 5 days ago

to r/sissycaptions

2 months ago

to r/sissycaptions by JessicaSissyCaptions

1 week ago

334

Having a Sissy BFF is so much fun!💗

Chastity Caption

Posted by JessicaSissyCaptions

Account Strength

80%

Account Age

4 months

Verified Email

Yes

Verified Flair

Total Karma

7,360

Link Karma

7,346

Comment Karma

Profile updated: 18 hours ago

to r/sissycaptions

2 months ago

to r/sissycaptions by fapInteractive

1 week ago

380

Its Meant To Be!

Chastity Caption

Posted by fapInteractive

Account Strength

100%

Account Age

4 years

Verified Email

Yes

Verified Flair

Total Karma

29,258

Link Karma

29,052

Comment Karma

153

Profile updated: 2 days ago

to r/sissycaptions

3 months ago

to r/sissycaptions by stuckinawoman

1 week ago

464

He's made you into the PERFECT SISSY on your knees & locked

Chastity Caption

Posted by stuckinawoman

Account Strength

70%

Account Age

9 months

Verified Email

Yes

Verified Flair

Total Karma

5,495

Link Karma

5,403

Comment Karma

Profile updated: 1 day ago

to r/sissycaptions

3 months ago

to r/sissycaptions by Mastersissytrainer

6 months ago

509

The magic words

Chastity Caption

Posted by Mastersissytrainer

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

9,697

Link Karma

9,255

Comment Karma

427

Profile updated: 5 days ago

to r/sissycaptions

6 months ago

to r/sissycaptions by cyndeden

6 months ago

176

Being caged by a real man changed me

Chastity Caption

Posted by cyndeden

Account Strength

80%

Account Age

3 years

Verified Email

Yes

Verified Flair

Total Karma

2,998

Link Karma

2,947

Comment Karma

Profile updated: 3 days ago

Posts updated: 4 months ago

to r/sissycaptions

7 months ago

to r/sissycaptions by TheCheshireDog

6 months ago

126

Head empty...well almost

Chastity Caption

Posted by TheCheshireDog

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

13,044

Link Karma

3,290

Comment Karma

9,685

Profile updated: 3 days ago

Posts updated: 5 months ago

to r/sissycaptions

7 months ago

to r/sissycaptions by CuriousStudent_

4 months ago

156

Collared, plugged and ready to serve

Chastity Caption

Posted by CuriousStudent_

Account Strength

100%

Account Age

5 years

Verified Email

Yes

Verified Flair

Total Karma

1,717

Link Karma

1,642

Comment Karma

Profile updated: 5 days ago

Posts updated: 4 months ago

to r/sissycaptions

7 months ago

to r/sissycaptions by Sissy-Swe

2 weeks ago

170

Whoops 🤷🏼‍♀️

Chastity Caption

Posted by Sissy-Swe

Account Strength

100%

Account Age

4 years

Verified Email

Yes

Verified Flair

Total Karma

13,386

Link Karma

12,580

Comment Karma

595

Profile updated: 2 days ago

Posts updated: 2 weeks ago

to r/sissycaptions

7 months ago

to r/sissycaptions by kyliesinsxxx

6 months ago

714

It’s amazing what blackmail, chastity, and hypno can achieve

Chastity Caption

Posted by kyliesinsxxx

Account Strength

80%

Account Age

1 year

Verified Email

Yes

Verified Flair

Total Karma

5,285

Link Karma

4,617

Comment Karma

668

Profile updated: 3 days ago

Posts updated: 6 months ago

to r/sissycaptions

7 months ago

to r/sissycaptions by Bigcockjock2023

7 months ago

409

Which number are you slut?

Chastity Caption

Posted by Bigcockjock2023

Account Strength

Disabled 7 months ago

Account Age

11 months

Verified Email

Verified Flair

Total Karma

8,105

Link Karma

7,970

Comment Karma

135

Profile updated: 1 day ago

Posts updated: 7 months ago

Disabled

to r/sissycaptions

7 months ago

to r/sissycaptions by AshleyAnytime

6 months ago

112

Finally made it! lol

Chastity Caption

Posted by AshleyAnytime

Account Strength

Disabled 5 months ago

Account Age

1 year

Verified Email

Yes

Verified Flair

Total Karma

707

Link Karma

526

Comment Karma

181

Profile updated: 2 days ago

Posts updated: 6 months ago

Disabled

to r/sissycaptions

9 months ago

to r/sissycaptions by AlexisSissygirl

9 months ago

Tiny and pathetic

Chastity Caption

Posted by AlexisSissygirl

Account Strength

100%

Account Age

4 years

Verified Email

Yes

Verified Flair

Total Karma

26,665

Link Karma

26,102

Comment Karma

107

Profile updated: 2 days ago

to r/sissycaptions

9 months ago 1 comment

to r/sissycaptions by cyndeden

7 months ago

204

Real men don’t lock their clit up 😖

Chastity Caption

Posted by cyndeden

Account Strength

80%

Account Age

3 years

Verified Email

Yes

Verified Flair

Total Karma

2,998

Link Karma

2,947

Comment Karma

Profile updated: 3 days ago

Posts updated: 4 months ago

to r/sissycaptions

9 months ago

to r/sissycaptions by TheCheshireDog

6 months ago

It's important to keep eye contact while men cum on you!

Chastity Caption

Posted by TheCheshireDog

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

13,044

Link Karma

3,290

Comment Karma

9,685

Profile updated: 3 days ago

Posts updated: 5 months ago

to r/sissycaptions

9 months ago

to r/sissycaptions by TheCheshireDog

6 months ago

I'm I as pretty as your GF daddy?

Chastity Caption

Posted by TheCheshireDog

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

13,044

Link Karma

3,290

Comment Karma

9,685

Profile updated: 3 days ago

Posts updated: 5 months ago

to r/sissycaptions

9 months ago

to r/sissycaptions by Mastersissytrainer

1 week ago

156

Be Proud of Daddy’s Mark

Chastity Caption

Posted by Mastersissytrainer

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

9,697

Link Karma

9,255

Comment Karma

427

Profile updated: 5 days ago

to r/sissycaptions

9 months ago

to r/sissycaptions by cyndeden

7 months ago

163

I can’t believe my friend caged me!

Chastity Caption

Posted by cyndeden

Account Strength

80%

Account Age

3 years

Verified Email

Yes

Verified Flair

Total Karma

2,998

Link Karma

2,947

Comment Karma

Profile updated: 3 days ago

Posts updated: 4 months ago

to r/sissycaptions

10 months ago

to r/sissycaptions by elementalamalgam

1 week ago

220

You were made to be feminized

Chastity Caption

Posted by elementalamalgam

Account Strength

100%

Account Age

2 years

Verified Email

Yes

Verified Flair

Yes

Total Karma

140,326

Link Karma

139,234

Comment Karma

371

Profile updated: 1 hour ago

to r/sissycaptions

10 months ago

to r/sissycaptions by Mastersissytrainer

1 week ago

159

One Night to Submit

Chastity Caption

Posted by Mastersissytrainer

Account Strength

100%

Account Age

7 years

Verified Email

Yes

Verified Flair

Total Karma

9,697

Link Karma

9,255

Comment Karma

427

Profile updated: 5 days ago

to r/sissycaptions

10 months ago