A Boy and his Bra

i can't say for sure, but i probably have a greater fascination with bras than most crossdressers.  It hasn't always been that way.  Like most cd's or tv's growing up, panties were the object of my desire and the easiest things to sneak away and even wear on rare occasions!

i remember sneaking my sister's bra out of her drawer when no one was home and discovering how difficult it was to put on.  By the time i had the courage to try and wear it, my sister had graduated from training bras and the larger cup sizes had me fantasizing about what it would feel like to have small budding breasts!  Later, during one of my more daring "searches" i came across an older white training bra of hers and decided to see if she would miss it.  i hid it in a secret hiding place in the attic and no one ever found out about it.

i've also written about how i've become rather skilled at putting on a bra as well as taking it off.  These two posts (here and here) discuss the progress i've made in large part because of Diane's insistence that i practice.  Since then, Diane's also mentioned what appears to her to be my infatuation with brassieres.  Yesterday, She stated that She wants me to wear one all the time while i'm at home, and to start going out in public with one as much as possible.  "Doesn't it make you feel more feminine" She asked me? It certainly does.

The brassiere isn't something that remains out of sight as easily as so many other items of feminine clothing.  Panties, pantyhose, thigh highs, even corsets can be worn much more discreetly than a bra.  In addition, the tightness of a bra around your chest is a feeling that is with you the entire time it's on.  It's hard to forget you're wearing it.

Late yesterday afternoon, Diane decided that it was time to get intimate and sent me upstairs to get a few things ready.  i was to strip down to just my bra and nothing else and get her strap-on ready.  Once the strap-on was secured onto Her, She also was wearing nothing but Her own bra.  After the foreplay, i found myself on all fours with Diane behind me, teasing me with the tip of Her rubber cock while She gently touched my bra.

Once She was firmly inside of me and stroking back and forth, She ran Her hands over the straps of my bra, even snapping them back in a teasing sort of way.  "You love wearing a bra don't you sissy?" She asked me as She leaned over and stroked me.  i came instantly, once again exhibiting little if any self control.  It was an awesome feeling!