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wimpysissy Profile wimpysissy Profile views: 5918 Fanbase: 152 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: 3 months and 6 days ago Images viewed: 0 Images uploaded: 534 Gender: TS/TV Birth: 01/01/1990 Location: United States Last Online: 13 days ago Connect with wimpysissy Send Message Add Comment Become a fan Add to relations Status updates Comments (2) (See All Comments) Sissy-Whore-Ni Comments: 158 Commented on Jan 2, 2026 "Yes Mistress. *curtsies"   blowpipe10 Comments: 725 Commented on Dec 30, 2025 "Oh god yes! So hot.... nghghghh"   PerryW Comments: 10,272 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: 4,622 Commented on Dec 29, 2025 "Please fuck me more and harder, Mistress."   Sissyformommya Comments: 4,622 Commented on Dec 29, 2025 "Yes Mistress. I will remember that from now on."   Cee-Dee Comments: 296 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."   jad7444 Comments: 21,789 Commented on Dec 21, 2025 "But, but Ma'am, what if someone recognizes me??...."   jad7444 Comments: 21,789 Commented on Dec 21, 2025 "Ok, ok, Princess -- I'll suck it first -- there's NO WAY my poor virgin sissyhole could taking a pounding from your HUGE cock for the entire movie!...."   slutmaidrobert Comments: 2,707 Commented on Dec 3, 2025 "I know better than to bet against you, Mistree, for once you have your mind set up whatever it is will happen. I just fear you will ruin my pussy ass for any man you wish to use it in the future."   slutmaidrobert Comments: 2,707 Commented on Dec 3, 2025 "While you are that, your Mistress will be picking out the new toys she wishes to purchase to help with your ongoing training. In that way you will have no idea of what they are and she surprise you when you get home."   See All Comments | Add Comment

Galleries (23) (See All Galleries)   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    Vol 19 Femdom sissy maid chastity feminization captions   15     2025-11-28 02:35:57  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 (152) (See All fans)

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