Robin's TG Captions: #bad-boy

Hello, I'm Robin! Being a consistent reader of TG and sissy captions, I thought I'd contribute to the communities, which provided many great stories through the years. My posts will vary on topic, but they will always contain sissy, forced feminization, body swapping, and varying TG topics. I post every week. If you like what you see, give my blog a follow and comment because feedback is appreciated. I hope you enjoy. Etc. 18 - 07 - 2020

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Showing posts with label #bad-boy. Show all posts

Friday, July 24, 2026

Punishment Points at the Bar

By Howelling_Robin at July 24, 2026 No comments:

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Labels: #bad-boy, #before_and_after, #blackmail, #bondage, #co-worker, #college, #crossdress, #feminization, #forced, #forced-feminization, #humiliation, #punishment, #revenge, #SFW, #show-and-tell, #sissy_caption, #sissy_situation

Friday, July 3, 2026

4th of July Fireworks

By Howelling_Robin at July 03, 2026 1 comment:

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Labels: #acceptance, #bad-boy, #before_and_after, #coerced, #cousin, #crossdress, #feminization, #humiliation, #panties, #pet, #pic, #punishment, #set_up, #SFW, #show-and-tell, #sissy_caption, #sissy_situation

Friday, May 8, 2026

A Bright Pair For a Not So Bright Future

By Howelling_Robin at May 08, 2026 No comments:

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Labels: #bad-boy, #before_and_after, #boyfriend, #crossdress, #ex, #feminization, #girlfriend, #humiliation, #magic, #panties, #punishment, #revenge, #set_up, #SFW, #sissy_caption, #sissy_situation

Friday, April 17, 2026

The Skirt Ripper

By Howelling_Robin at April 17, 2026 No comments:

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Labels: #bad-boy, #before_and_after, #bodyswap, #caught, #feminization, #humiliation, #magic, #panties, #SFW, #show-and-tell, #sissy_caption, #transformation, #witch

Friday, March 27, 2026

Exposeasissy - Thane

By Howelling_Robin at March 27, 2026 No comments:

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Labels: #bad-boy, #bully, #caught, #classmate, #crossdress, #discovered, #feminization, #humiliation, #MyFave, #online, #panties, #punishment, #revenge, #set_up, #SFW, #show-and-tell, #sissy, #sissy_caption

Wednesday, October 15, 2025

30 Days of Captions – Day15_Proper

By Howelling_Robin at October 15, 2025 No comments:

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Labels: #30_DoC, #bad-boy, #before_and_after, #brother_to_sister, #crossdress, #feminization, #forced, #forced-feminization, #humiliation, #makeover, #pic, #punishment, #revenge, #set_up, #SFW, #sibling, #sissy_caption, #sister, #sisters_friend

Monday, October 13, 2025

30 Days of Captions – Day13_Harbor

By Howelling_Robin at October 13, 2025 No comments:

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Labels: #30_DoC, #acceptance, #bad-boy, #before_and_after, #caught, #crossdress, #feminization, #halloween, #highschool, #humiliation, #MyFave, #panties, #punishment, #SFW, #show-and-tell, #sissy, #sissy_caption, #sister, #spanking

Wednesday, October 8, 2025

30 Days of Captions – Day7_Custody

-I'm sorry I'm late. I was busy yesterday. Friday I'll set up auto posting so I don't forget-

By Howelling_Robin at October 08, 2025 No comments:

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Labels: #30_DoC, #bad-boy, #blackmail, #bondage, #caught, #cheating, #college, #confession, #crossdress, #feminization, #forced-feminization, #girlfriend, #humiliation, #panties, #punishment, #revenge, #SFW, #show-and-tell, #sissy, #sissy_caption

Monday, October 6, 2025

30 Days of Captions – Day6_Pound

By Howelling_Robin at October 06, 2025 No comments:

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Labels: #30_DoC, #bad-boy, #before_and_after, #blackmail, #bully, #college, #costume, #crossdress, #feminization, #forced, #forced-feminization, #halloween, #humiliation, #MyFave, #party, #set_up, #SFW, #show-and-tell, #sissy_caption, #sorority

Saturday, October 4, 2025

30 Days of Captions – Day4_Difficult

By Howelling_Robin at October 04, 2025 1 comment:

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Labels: #30_DoC, #acceptance, #bad-boy, #caught, #college, #confession, #costume, #crossdress, #feminization, #halloween, #MyFave, #SFW, #sissy, #sissy_caption, #sissy_situation, #sister

Thursday, October 2, 2025

30 Days of Captions – Day1_Acquit

By Howelling_Robin at October 02, 2025 No comments:

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Labels: #30_DoC, #acceptance, #bad-boy, #before_and_after, #coerced, #crossdress, #feminization, #forced, #forced-feminization, #operation, #panties, #set_up, #SFW, #show-and-tell, #sissy, #sissy_caption, #spicy, #transformation

Thursday, May 1, 2025

Extra Skin

By Howelling_Robin at May 01, 2025 No comments:

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Labels: #acceptance, #bad-boy, #before_and_after, #bikini, #crossdress, #feminization, #girlfriend, #MyFave, #SFW, #show-and-tell, #sissy, #sissy_caption, #sissy_situation, #swimsuit, #willing

Saturday, December 21, 2024

30 Days of Captions – Day21_Lock

By Howelling_Robin at December 21, 2024 No comments:

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Labels: #30_DoC, #bad-boy, #before_and_after, #bondage, #boyfriend, #caught, #cheating, #crossdress, #ex, #feminization, #forced, #forced-feminization, #girlfriend, #humiliation, #panties, #punishment, #SFW, #show-and-tell, #sissy, #sissy_caption

Friday, December 20, 2024

30 Days of Captions – Day20_Compliance

By Howelling_Robin at December 20, 2024 No comments:

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Labels: #30_DoC, #bad-boy, #before_and_after, #bra, #bully, #coerced, #crossdress, #feminization, #forced, #forced-feminization, #humiliation, #parents, #pic, #SFW, #sissy, #sissy_caption

Sunday, December 8, 2024

30 Days of Captions – Day8_Duty

By Howelling_Robin at December 08, 2024 No comments:

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Labels: #30_DoC, #bad-boy, #blackmail, #bully, #crossdress, #feminization, #forced, #forced-feminization, #highschool, #humiliation, #panties, #pic, #punishment, #revenge, #set_up, #SFW, #show-and-tell, #sissy_caption, #sister, #teenager

Saturday, December 7, 2024

30 Days of Captions – Day7_Chart

By Howelling_Robin at December 07, 2024 1 comment:

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Labels: #30_DoC, #bad-boy, #crossdress, #feminization, #forced, #forced-feminization, #highschool, #humiliation, #parents, #punishment, #SFW, #sissy_caption

Sunday, December 1, 2024

30 Days of Captions – Day1_Flour

By Howelling_Robin at December 01, 2024 1 comment:

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Labels: #30_DoC, #acceptance, #bad-boy, #crossdress, #feminization, #girlfriend, #SFW, #sissy_caption, #willing

Tuesday, August 6, 2024

Camp Sissywalka – Harlan v2

By Howelling_Robin at August 06, 2024 No comments:

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Labels: #bad-boy, #bully, #Camp_Sissywalka, #crossdress, #feminization, #forced, #forced-feminization, #humiliation, #MyFave, #panties, #punishment, #SFW, #show-and-tell, #sissy, #sissy_caption

Saturday, June 29, 2024

30 Days of Captions – Day29_Dependence (CS) v2

By Howelling_Robin at June 29, 2024 1 comment:

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Labels: #30_DoC, #bad-boy, #bikini, #Camp_Sissywalka, #caught, #crossdress, #feminization, #forced, #forced-feminization, #MyFave, #punishment, #set_up, #SFW, #sissy, #sissy_caption, #SP, #spicy, #swimsuit

Thursday, June 13, 2024

30 Days of Captions – Day13_Investment (CS) v2

By Howelling_Robin at June 13, 2024 1 comment:

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Labels: #30_DoC, #acceptance, #bad-boy, #bully, #Camp_Sissywalka, #crossdress, #feminization, #MyFave, #set_up, #SFW, #sissy, #sissy_caption, #sissy_situation, #willing

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I am still developing as a writer, so any constructive feedback, complements, and story ideas, please post them in the comments! Also let me know if there are certain captions or tags you'd like to see more of in the future.

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Howelling_Robin: I'm Robin Howell! I like crossdressing, wedgies, spankings, & embarrassment. I write when the time permits and I look forward to publishing content soon!

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All images used in this blog are used under "fair use" doctrines. I do not claim any copyright ownership of the pre-existing material. All images obtained are found on other public photo websites. If you are the owner of an image and would like for the selected content to be removed, send a note and it will be removed immediately. This content on this blog is not intended for any other use other than transformation fiction ideology and entertainment. None of the stories are intended to reflect said models.