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wimpysissy Profile wimpysissy Profile views: 6829 Fanbase: 162 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: 4 months and 21 days ago Images viewed: 0 Images uploaded: 549 Gender: TS/TV Birth: 01/01/1990 Location: United States Last Online: 21 days ago Connect with wimpysissy Send Message Add Comment Become a fan Add to relations Status updates Comments (2) (See All Comments) wilkoprimer Comments: 210 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: 143 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."   PerryW Comments: 10,323 Commented on Jan 22, 2026 "my girlfriend used to dress me up, because her fantasy was to fuck another woman, we got married and then it turned into having men fuck me dressed as a woman. When she got bored with that, she left because she wanted to be fucked and abused by another woman"   denise_p Comments: 691 Commented on Jan 21, 2026 "i am a Cocksucker"   Sissy-Whore-Ni Comments: 176 Commented on Jan 2, 2026 "Yes Mistress. *curtsies"   blowpipe10 Comments: 735 Commented on Dec 30, 2025 "Oh god yes! So hot.... nghghghh"   PerryW Comments: 10,323 Commented on Dec 29, 2025 "it started so innocently, a bit of dress up, then a bit of make up, then a wig, the shoes, then more heavy makeup, the high heeled shoes, the cage, the pegging"   Sissyformommya Comments: 4,979 Commented on Dec 29, 2025 "Please fuck me more and harder, Mistress."   Sissyformommya Comments: 4,979 Commented on Dec 29, 2025 "Yes Mistress. I will remember that from now on."   Cee-Dee Comments: 467 Commented on Dec 28, 2025 "My lovely Mother-in-law did exactly this to me on a Halloween weekend. She took me into the back room, placed a soft cushion on the floor and watched me give blow job after blow job. I was in sissy heaven and the lady at the checkout counter occasionally stopped by to watch. I loved it."   See All Comments | Add Comment

Galleries (24) (See All Galleries)   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    private   1     2025-11-29 22:47:24  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 (162) (See All fans)

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