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wimpysissy Profile wimpysissy Profile views: 7627 Fanbase: 169 About Me Tumblr banned my blog of over 2000 original captions because it was to adult so am going to start adding them here. i hope people enjoy them they are mainly sissy, femdom, cuckold, maid, chastity etc. i do take requests if people would like to make requests. Interests bondage , chastity , cuckold , femdom , feminisation , humiliation , maid , sissy Signed up: 6 months and 7 days ago Images viewed: 0 Images uploaded: 569 Gender: TS/TV Birth: 01/01/1990 Location: United States Last Online: 1 month and 5 days ago Connect with wimpysissy Send Message Add Comment Become a fan Add to relations Status updates Comments (2) (See All Comments) tvladyjessica Comments: 614 Commented on Apr 2, 2026 "Now play with the dildo...i'm curious to see if you can reach an orgasm anally"   tvladyjessica Comments: 614 Commented on Apr 2, 2026 "And she fotgot to tell: she will not use lub"   tvladyjessica Comments: 614 Commented on Apr 2, 2026 "Punishment will be: serve the mistress, serve her lover, then hard bondage, big plug, smallest cage, clamps on the nipples all night long"   njcaptionlover Comments: 3,245 Commented on Apr 1, 2026 "would love to be in that sissy outfit and pimped out by Mistress"   Cee-Dee Comments: 668 Commented on Mar 14, 2026 "I can't believe Mistress is wasting my and her time by making me suck a toy. I want the real thing."   Cee-Dee Comments: 668 Commented on Mar 14, 2026 "There is nothing more exciting than to have a husband sent to sissy school and then return home to sissies wife totally sissified and sissy trained. Wife's sex life from now on will bill be open to choose any lover she so desires and sissy husband will assist, watch and love every minute of her sexual activities. Trust me, and make the arrangements."   Cee-Dee Comments: 668 Commented on Mar 14, 2026 "What a waste, confining a sissy pansy fairy is not the way to go. Free the sissy up and permit the sissy to perform at sissies highest peak. Sissy will love it, Mistress will be happy and the clients will return again and again."   ViennaSheraton Comments: 410 Commented on Mar 11, 2026 "Properly trained maid."   wilkoprimer Comments: 208 Commented on Feb 5, 2026 "I want to be owned by a woman who fucks my boipussy to humiliate me and destroy my masculinity."   littlesissytim Comments: 155 Commented on Jan 24, 2026 "Once Aunty caught timmy in her lingerie there was no going back. Over that school holiday timmy learned just what it was to be a sissy and to serve a strong female. Returning to school as a sissy was difficult but not without its benefits."   See All Comments | Add Comment

Galleries (25) (See All Galleries)   Vol 24 Femdom sissy maid chastity feminization captions   20     2026-03-11 16:48:30    Vol 23 Femdom sissy maid chastity feminization captions   15     2026-01-20 14:58:58    Vol 22 Femdom sissy maid chastity feminization captions   20     2025-12-29 19:33:47    Vol 21 Femdom sissy maid chastity feminization captions   15     2025-12-17 19:07:31    Vol 20 Femdom sissy maid chastity feminization captions   15     2025-12-02 14:27:19  Favorites (0) (See All favorites) Clubs (10) (See All clubs) Sissy Slut University (SSU) Femdom mostly orgasm denial (captions only) Feminization captions and stories ONLY Forced Feminization and Sissification Sissification Bois become gurls femdom captions SISSY STUFF Band Of Sissies Maids, French Maids, Sissy Maids Fanbase (169) (See All fans)

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