I'm sitting here with a very sore butt, writing this up before I go back to my real job. My mother in law, who is supportive of my dressing and helps my wife came over unannounced and wasn't to happy to see my clothing choice. I was wearing a nice pencil skirt, heels hose and a blouse. My mother in law believes I am a sissy and that a sissy should dress in an overtly sexy and slutty manner. Not comical but more a sexy secretary but without the power clothes. i.e. tight pencil skirts or power clothing. Needless to say she called my wife who gave her cart blanch to rearrange me. Needless to say I am now sitting at my desk wearing 5" platform heels with a 3/4 inch lift, stockings, a corset, a very short pleated skirt, black bra, white blouse, large earnings, hot makeup and courtesy of a spanking and plug, a sore bottom.
The spanking was for daring to wear power clothes in her presence, despite not knowing she was coming over, the plug was because I should be wearing one. Dare I say but I have quite a smile on my face not just from the fact that every movement excites the plug in my ***, but because I am right where I want to be and very lucky.
MyFeminineSide MyFeminineSide
4 Responses Aug 18, 2014

Oh my god!! How lucky are you!!! And mom inlaw setting things straight!! So hot!!!

you are so luky to have a wife and mother in law like this!!!

Well sissy should have a plug in their arse and if you did wrong you should be spanked, so I bet you wanted ur mother in law to catch you right?

Pretty much the case now. I must admit that I sometimes miss being able to just throw on a denim skirt and tee shirt and be sloppy. now I can still wear a denim mini skirt but i need my underwear and makeup done right. It is nice to essentially have to dress sexy though, ultimately its about feeling good. Ive lot some say in what I do but have gained so much more. while I'm not a ****, I am a sissy tart and love it!

You are so lucky. Can I work for you or her or them. I'd love to be the bosses slutty secretary and we would both work and please the COO and CEO.