Ann Summers Party Scenario with my vanilla friends

Last week, my vanilla friends and I had a particularly entertaining CFNM session with a sissy slave who was possibly the most entertaining sub I've had the pleasure of humiliating!  We're already looking forward to the next one.

Here's a teaser of what happened...

A couple of weeks ago I was delighted to find this application from a sub in my inbox:

"My interests include cfnm, anal play & sissy humiliation. I have been lucky enough to enjoy some fantastic experiences so far, but there is something about Mistress plus Vanilla Friends dynamic that is just the ultimate for me. 
I have always been interested in femdom & I particularly enjoy the feeling of being outnumbered - the vulnerability, the teasing, the feeling that there's a joke that I'm not in on, and I guess the embarrassment of having my kinkiest secrets revealed to a raucous/rowdy (or classy, I'm not fussy!) group of women - that I love.

I think you could probably draw enough from me earlier answer, but I'll reveal maybe a fantasy/role play idea that I think would be fun...
One of my oldest fantasies is being unexpected guest at an Ann Summers party/girls night in - I could be the lodger that arrives home early, for instance. But the girls decide I can be some use - maybe modelling some of the male garments, but from there it escalates to more humiliating things, like the feminine clothing too, being dressed up as a sissy, and then maybe being a guinea pig for the women to try out the Dec toys, I'm sure you get the idea.
I love the humiliation of sissy play, and I would say I enjoy a playful style of domination."

I knew that my friends would absolutely love this scenario and that we would have a lot of fun teasing him and using him for our entertainment.  

I invited one of my closest friends who has never watched a session before to join us.  She's naturally dominant and we always have fun together on nights out teasing men and seeing what we can get away with saying or doing to them, while they still keep chasing!  The second vanilla friend to join us has watched a number of sessions over the past couple of years.  She's mischievous and sometimes simply outrageous, making for memorable moments in every session she joins.

My girls and I had so much fun with our sissy, playing dress up, making him dance for us, quizzing him, transforming him with make-up, nail varnish and a wig...There were so many funny moments, that I don't know if I can pick a favourite.  

I think one of the most humiliating moments for my sissy was when I made him get down on all fours in front of the girls to test his blow job skills.  Sissy training involved a lot of critique!  Though sissy listened well and we were impressed with sissy's ability to booty shake and suck on my strap-on; an essential skill bringing you to an intermediate BJ level and proving that sissy's can multitask.  

The session very nearly came to a cruel ending when sissy didn't manage to cum for us within my ten second countdown.  As sissy had been so entertaining, I decided to pass the decision to my vanilla friends.  After listening to slave m's pleas, and looking at the despair on his face, they showed mercy and allowed extra show time!  I can think of many, many humiliating things, but wanking with an audience and to a countdown ranks pretty highly...

Sissy's relief was palatable when he managed to cum within the second countdown...but his elation was short lived as I grabbed the hand I made him catch his cum with and forced him to clean up and swallow, at which point my vanilla friends were truly disgusted!

I will post slave m's perspective soon...

I have so much fun when my vanilla friends join me for sessions like this, based around playful humiliation.  We'd love to hear from more subs who are feeling brave!

Kinky regards,

Miss Helen