Mistress Allure and I had a duo session the other day with a client who wanted to serve us as our sissy French maid.
The session was to be at Chez Oz and the scenario was for Mistress and Master to coerce a young straight man, our client, into crossdressing, verbally humiliate him, laugh at his tiny cock and pathetic attempts to serve us and finally to force him to suck my cock and take Mistress's strap-on up his tight virgin ass.
I went on amazon and purchased the necessary items for his sissification a week in advance to ensure delivery in time for his session.
I got him a blonde wig. It comes with a detachable wig cap. I'll wash the cap after every session to keep thing hygienic for my other sissified slaves. The wig itself is washable too. Madam Helle kindly gave me step-by-step instructions on how to hand wash, dry and brush a wig. Cleaning cum out of crossdresser's wigs isn't everyone's idea of a perfect evening in but I'll manage.
A French Maid Costume. It's a women's XL and the fabric is stretchy so it should fit almost any average to large man.
And UK women's size 12 high heels. The size corresponds to about a men's size 10. Not excessively high so that a beginner might totter around on them without breaking his ankles. With open backs so that future sissies can wear them even if their shoe size is a bit bigger or smaller.
I drafted some sissy captions to put here on my blog and to use the quotes in the roleplay =
After you've finished your chores Mistress and Master are inviting some guests over. If any of them want to use you, then just do as you're told. They'll probably take turns fucking you, one after another, all night long and you'd better take it without complaining.
Behave yourself or well revoke next months cum allowance. You'll have to wait two months instead of just one month before we allow you to touch your pathetic little man clit.
A good sissy maid needs to know her place. In your case, your place is on your knees with my cock in your mouth.
Look at you mincing about like a horny little slut. You look like you've been caught with your hand in the cookie jar. Or was it with your cock in Mistress's panty drawer. I'll slam the drawer shut with your little cock in it if I catch you jerking off into my panties.
There, there sissykins, you do look ridiculous and the boys will laugh at you. But don't worry, I'm sure they'll all still fuck you. You'll get more cock than you can handle once the gardeners, kitchen hands, stable boys, and man servants see you in that short skirt. You'll be swallowing more seamen than the Bermuda triangle.
After all that, he showed up, but was so nervous he decided he couldn't cope. He stammeringly informed us he wasn't going to be able to go ahead with the session. These things happen. Sometimes taking something that's a long term fantasy and making it a reality just doesn't work out. One benefit of doing so with professionals is that no harm is done if you choose to back out.
He paid us half our fees to compensate us for the inconvenience which was only fair. Mistress Absolute had travelled across London to be here at my place for his session and had taken the time to dress up and prepare for his roleplay. I'd been shopping for all the props and we'd both reserved the time on our calendars where we could have made other plans.
Honestly, I think after the adrenaline wore off he was probably kicking himself for not going ahead with the session. But it was his decision to make. If he does lose his sissy virginity one day, I hope he has a great time. And if all he got from the experience was the certainty that being a sissy French maid isn't for him, that's fine too.