Why I love crossdressing sessions

by | Apr 17, 2012

I just started writing this post about shorter sessions because I’ve been talking quite a lot about my extended and multi-day sessions but not mentioning all the shorter sessions I do as well. Then somehow when discussing how two hour bookings are taking over from one as most popular length in my diary I got distracted writing about crossdressing and I realised that I really just want to talk about playing dress ups :)

This week I’ve been having a lot of fun playing with my “special girls” – the careful application of beautiful makeup, lingerie and outfit changes, shoe choice and a perfect shining hairpiece… then we often descend from the decadent surrounds of the North Floor to the schoolroom for deportment lessons or to dungeon or sling room for some other sorts of explorations.

I would say that a majority of my crossdressing sessions are full transformation – last week one “special girl” who’s been seeing me for quite some time found out just how different it feels to see yourself with carefully applied makeup… s/he was actually doing an extended session instead of the usual shorter playtime, and instead of dressing herself quickly before we focus on our SM play. This time sitting upstairs in my makeup chair the transformation was more of a focus – s/he was astonished at how glamorous the right makeup and some pretty false eyelashes were!

I think that is one of the main reasons that I enjoy these sorts of sessions so much. I’ve been thinking about it recently – why exactly do I love playing dress ups? In some ways it’s not necessarily what you would expect from me – I’m well known for enjoying “heavy” activities like singletails, caning and piercing. Severe leather or rope bondage – that sort of thing…

But I think it’s the intensity of the experience that captures my attention. In a similar way to why I love playing with novices and introducing them to BDSM and Female Domination.

With full transformation the look in someone’s eyes when they see themselves in the mirror for the first time is amazing. The girl who was there all along hidden somewhere in their everyday masculine life. It makes me feel special to be able to see her too and bring her out of hiding to play. And there’s such a variety of “girls” also – from cheeky girls in a school uniform, sissies in pretty pink dresses, sexy french maids, rubber dolls, tramps in leather miniskirts, ladies in pretty dresses – though there’s no reason to restrict exploration to one sort of look or personality – changing your mind is supposed to be a ladies’ prerogative!

That said I’m feeling very frustrated with my cross-dressing area up on the North Floor. It seems to have got out of control – maybe because I keep buying new things! But there are just so many different looks that I want to be able to select – and of course a range of sizes that need to be covered. The clothes rack is so full I can barely see what’s there and the corset drawer is overflowing as are the boxes of lingerie and stockings. Plans afoot for renovations which are very exciting – though these things always seem to take a lot longer than expected…

In fact there are some very exciting changes planned for Carisbrook when I get back from my US travels at the end of May!

Originally published at Mistress Servalan on tour. You can comment here or there.