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Sissy Role Play Advice      Miss Violet 800-601-6975

The Question

I am a straight male who enjoys some cross-dressing sissy play, but I do not think I fit the “textbook” definition of sissy, I do not want to be a girly girl who craves cock. I like it when a Mistress dresses me as a sissy and even coerces cock-sucking, where the erotic thrill of cock-sucking in that scenario is not the cock, but rather an opportunity to demonstrate my obedience and devotion to the Mistress who asks it, and maybe bring a smile to her face if watching a sissy suck cock is what she enjoys.

Another Desperate Sissy

Recently I was contacted on facebook by another sissy desperate for role play. Since I do use a feminine name on facebook, it is not too uncommon for people to think I am a Mistress. I notify them, and usually they reply with something like “Well this is awkward” and that’s that.

This one didn’t, we ended up talking and now are going to attempt a role play. The scenario, which I came up with, is that a Mistress is organizing a bachelor party except instead of having anatomical females dancing for the rowdy drunk boys, she is going to have two sissies dancing for them, me and the other person.

Dancing for the Boys

Since guys like to see girl on girl action at bachelor parties, me and this other sissy have been instructed to become familiar and comfortable with each other so that when we are dancing for the boys, we can do girl on girl action for them and look comfortable doing so.

So it’s a coerced bi scenario.

Part of me doesn’t want to do it because I am straight and this isn’t a scenario where I am following a Mistress’ command, but part of me is really excited to do it because it is an opportunity to explore how I would really respond if a Mistress did put me into this situation. This will be done via chat with no video, so it is safe. 

Tips for Preparing

I want to do this, but I am having trouble mentally preparing and I hope that maybe you might have some tips that can help. It is a role play and I see it as a way to prepare for the possible event of someday being able to do this for a Mistress and that is what makes it exciting, but there are still mental blocks I need to overcome. I want to have fun and I am hoping the other person has fun too.


My Answer

I am glad you contacted me about preparing mentally for sissy roleplay.  A really fun opportunity has come to you for coerced sissy play and you want to take advantage of it.  This is very exciting!  I can understand the part of you that is feeling nervous.  Being mentally prepared can make a big difference in the enjoyment you get from a new situation, like this one.

There are some things you can do in advance to prepare yourself for the role play.

Gearing Up

  • Visualization:  Take some time to close your eyes and visualize yourself in the scenario.  See yourself cross dressed, feeling excited and nervous, and having a great time.  If a situation arises that causes you to feel nervous, visualize yourself calmly handling it with ease.  Doing this will allow you to feel more comfortable when the role play is happening, because you would have done this before in your mind.  Preparing mentally for sissy roleplay begins with you getting comfortable with the idea.
  • Facing your fears:  Write down three worst fears you have about this role play.  Then write down a plan for how you will handle it, should it come up.  Having a plan makes you better prepared.
  • Psyching Yourself Up:  Just before you do this role play, tell yourself “This is going to be a lot of fun”, “I am going to love this role play”, “This is something I really want to do”.  What you tell yourself becomes your reality.

The Big Event

When you are in the middle of this roleplay, remember that it is acceptable and healthy to be firm with your boundaries.  If you said in advance that you are not comfortable with anal sex, and the other sissy tries to bring that into the scene, you can say “I am not comfortable with that.  Let’s leave that out of this scene.”  And then get back to the fun.

Knowing you can do this may even eliminate some of your worries.

Sissy Chat

Preparing mentally for sissy roleplay helps to ensure you have a great session.  Please do let me know how your role play goes.  I am sending you positive intentions for a very exciting, successful first sissy role play.  You will find that I enjoy a little chat with sissies; hearing about their adventures.  Have fun!