by Sissyville | Oct 12, 2018 | Ms Constance, Sissy Assignments
← Previous Next → Hey, girls! Well, it is the perfect time of the year for you to go out in public as your authentic sissy self! I want you to take full advantage of the season and your ability to go out feminized without fear…..after all Halloween is...
by Sissyville | Oct 19, 2014 | Sissy Assignments, Sissy humiliation
What better time to unleash your inner slut? Unfortunately, not every day is appropriate for fishnet stockings, PVC miniskirts, and long colorful wigs. If you have to deal with the burdensome restrictions of living discreetly, Halloween might offer some respite. After...
by Sissyville | Oct 7, 2010 | Feminization, Sissy Assignments, sissy dressing
So the area parochial schools have been back in session for nearly 2 months now. And I must admit the flurry of pleated mini skirts, patterned knee socks, and tight knit polos have made me long for my days in uniform and I can’t help but wonder, did I look that...
by Sissyville | Oct 31, 2009 | Feminization, Panty Boys, Sissy Boys, sissy phone sex, sissy school, Sissy Stories, sissy training, Sissyville Phone Sex
I love Halloween fun, and just wow… Ms. Cecilia and Ms Cassandra make dressing up sound like so much fun! Now that you have picked your outfit and you have chosen the perfect make-up. I will be sending you on a sissy scavenger hunt. First you will need the below...
by Sissyville | Oct 26, 2009 | Feminization, Panty Boys, Sissy Boys, sissy phone sex, sissy school, Sissy Stories, sissy training, Sissyville Phone Sex
It’s my favorite holiday… Halloween! And I’ll bet anything it is yours too, gurls. Let’s plan this year’s outfit. I won’t make you into a fairy princess this year as I did last. I have something racier in mind, but I will let you...
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