On Being a Shy Girl and Dressing Up


Being an innately shy person naturally I wasn’t going to blog about this particular event. BUT this magazine is all about pushing yours and my sexual borders and so I shall tackle a rather embarrassing topic for myself. I am a cute person, with a pretty face and great legs… I wear short skirts and tight trousers to demonstrate this to the best of my ability. Because of this “confidence” (or vanity, call it what you like) I am not used to people, teasingly or otherwise, requesting that I hide my best assets under a heavy layer of clothing. So, when the guy with whom I would currently very much like to sleep with suggested I wear something akin to a pair of men’s trousers when I go to bed with him I was bemused. And then I questioned why he would like me to dress like a man, and then I called my best friends… all 10 of them.

Hence it was during one of these many phone calls that ate away at both my Friday and Saturday study hours that I made the following self-discovery; I am not as open-minded about role-play as I thought I was. I don’t know if this stems from the fact that my own sexual fantasies involve locations and not dress-up or if I’m just exceedingly uncomfortable with this aspect of sex. Mayhap it was the actual costume itself that threw me off. I understand schoolgirl outfits (again, I love my legs) and I understand naughty nurses, maids etc. so why was it that I simply could not grasp the fascination with baggy trousers with nothing worn under them.

I’m not even capable of fathoming this interest… perhaps it’s this rough and tumble like outfit that really gets him going. Perhaps it is the idea of a girl seeming sort of unkempt and untamed on the outside and obliging and ingratiating on the inside. I don’t really know, honestly… although I do think I’m nearing the truth here.

What I realised halfway through conversation with best-friend number 6 was that it wasn’t even the costume itself that through me, it was this idea that I was just going to show up in a uniform when I wished to sleep with him. Listen, buddy, the first time I sleep with you is not going to involve me in a pair of men’s dungarees. The first time I sleep with you is going to be MAGICAL (okay, maybe not so much) but it will be for the most part unplanned. I hate the presumptuousness that would be me showing up in a predetermined outfit when I felt the need to have sex with him. I’m not being paid and so I’m not wearing a bloody uniform!

And so, finally when I had reached this firm conclusion somewhere between conversations with best-friends number 6 and number 9 best-friend number 10 made this insightful comment; “The first time you have sex with someone is best done without planning and without assumptions on either side. Also, Jehan-sweety just be happy he didn’t ask you to wear a diaper and baby costume.”

She’s right, atleast when it comes to what I desire, a little bit of impulsiveness goes a long way. Indeed I am also quite grateful that he didn’t request the baby outfit, it’s all a bit too Freudian for me. I am not saying I won’t dress up for him, I will… I enjoy it. I’m just going to wait a bit before I tackle androgynous clothing in the bedroom… everything needs to be worked up to. Or maybe I just need to redefine what I think “sexy” is.



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