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The Clothes Don't Just Fit the Girl...

Posted by: Author: Age: 19 Posted on: 2 comments
0 likes 408 views Category: Masturbation Male Solo Tags:

The last message I posted was about my awakening to a person of the same sex, but now I will focus on my experiences of cross-dressing...


I am the oldest of three children, and my two younger sisters are seven and sixteen. The older of my sisters is well-built (to put it politely), and she has developed quite an attractive body... specifically her breasts!
When she is out working and I am home from college (very rare, but still frequent enough), I sometimes sneak into her bedroom and try on some of her clothing. My favourite activity involves putting on her bra and pants, with a skirt and shirt over this. For some reason, my sister finds the need to further enhance her cleavage with small pads that fit into her bra - these help me to catch up with her blossoming assets! A pair of leather boots, her glasses and some jewelry complete the look, though on some rare instances (when I know that I am alone in the house and there is enough time to clean up after) I have even applied make-up in the same style as my sister. For that moment, it is almost like I have become my sister!
I enjoy standing in front of her mirror and stripping down, before sitting on the floor and masturbating. For most of the time I end up ejaculating on the (male) faces looking up from her glossy magazines, though sometimes I enjoy putting her glasses on a dummy head she uses to hold wigs - this helps me to imagine that I am giving my sister a facial (something that she definitely would not agree to). Yes, of course I clean up when I have finished!
This might sound a little odd to some people, but I sometimes even wish that I was born a girl. The sensations of imagining myself as a female would ensure that I fit in more around the house, as my two sisters always seem to be treated better.
Who knows? Maybe one day I will be posting here as 'Janine' or something...



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