Humiliation Questions While Sissy Shopping

Humiliation questions to a lingerie store sales associate is essential for sissy training. It is useless to skulk around the panty tables and sheepishly pay for your sissy panties with head bowed as you leave. Sissy pride, I say! Victoria’s Secret associates are well trained with transgender clients so don’t be afraid . Here are some examples, and a few may be a bit bold if you dare. Have a hand held recorder because I need proof. Be sure to post more questions in the comment section. This is part of sissy training to keep you sharp, fearless, and humiliated with humiliation questions.

  1. Will my bum look big in these panties?
  2. Do you sell panties with a visible panty line?
  3. Will these panties hold in my butt plug when I am out shopping?
  4. Should I wear panties under pantyhose? or over the top?
  5. Which panties look good under sheer nude pantyhose?
  6. Will you hold my handbag while I find my tampons?
  7. What color pantyhose goes with my skin-coloring/hair?
  8. Will this bra show through my blouse?
  9. Do you have many sissies coming in to shop?
  10. Do you have DDD breast forms?

Humiliation Questions At The Lingerie Store: Ms Cassandra 1-800-730-7164

Painful Nipple Play

Let’s move on to FFB’s nipple torture game. I have to keep the fag on her toes from now on. So I get this e-mail:

Mistress, I have a confession to make. The slut has not been placing nipple clamps on it’s nipples prior to phone calls.
It has been slack Mistress, and I think the only solution is to have a weekly photo check so that you can see that clothes pegs have been placed on its nipples in the correct position, that is the most painful position (position 3).
The slut will in future send you a photo prior to every call at the same time as the normal chastity photo check.
FFB
I decided it would be best to have surprise spot checks in the morning before she goes about her business, here and there, unpredictably.
I send me an email, and write” Position 3,  10 minutes” and she has to place nipple clamps on at position 3 and take 2 time-stamped photos. the first photo no later than 5 minutes after she sends me the email, and the second photo 10 minutes later. (refer to photo for positions)
Of course the time I say can be any time I like, 5 minutes (easy), 10 minutes(not so easy), or 30 minutes( quite hard). If I want to make it really painful, I can say ” double clamps!” which means nipple clamp on top of nipple clamp, really, really, really painful. but this is good for her, because it makes her reflect on her faggotry and ineptness as a male.
Mistress Cassandra 1-800-730-7164