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Overview  Sissy  Pretty gurls and...  Sissies get caught   tranny on top altered...  My Sissy Fantasies 12  I want to be your...  Locked up bitches  Other people's...  fuck me like a bitch  obedient  sissy boy  BBC sissy slave  Web Found Sissy Dildo...  My Sissy Fantasies 14  For my sissy gurl...  Indulgent Mommies  [ShadowJack] Practice...  Some sissy captions I...  Prissy Art Favorites  Sissy Cap Findings 4  Panties Caption 01  Accepting Mommy Sissy...  The Best of Shadowjack  DEAREST MOTHER IN LAW 9  Femdom Humiliation Sissy  Gallery Name   Images   Size   Added    Pretty gurls and bondage 4   39  Large  2016-04-04    Sissies get caught   52  Large  2022-01-05    tranny on top altered drawings 4   66  Large  2021-12-22    My Sissy Fantasies 12   618  Large  2013-06-06    I want to be your sissy faggot bride   52  Large  2021-11-20    Locked up bitches   650  Huge  2018-01-02    Other people's humiliated sissy husbands   113  Large  2013-01-31    fuck me like a bitch   200  Large  2015-08-23    obedient    124  Small  2020-04-13    sissy boy   56  Large  2021-11-17    BBC sissy slave   4041  Small  2016-03-18    Web Found Sissy Dildo Gifs   46  Small  2021-10-30    My Sissy Fantasies 14   378  Medium  2013-07-30    For my sissy gurl housewife   949  Large  2014-03-19    Indulgent Mommies   12  Medium  2014-03-17    [ShadowJack] Practice Girl   10  Large  2019-09-02    Some sissy captions I missed    243  Large  2021-02-17    Prissy Art Favorites   36  Large  2020-04-09    Sissy Cap Findings 4   60  Large  2015-12-19    Panties Caption 01   24  Large  2020-10-21    Accepting Mommy Sissy Sons   85  Large  2018-09-30    The Best of Shadowjack   51  Large  2020-03-17    DEAREST MOTHER IN LAW 9   49  Large  2019-07-23    Femdom Humiliation   41  Large  2014-04-17   :: prev ::   | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |  :: next ::