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 a cute neighborhood girl’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, she 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 basement and no one ever found out about it.
Now I’ve also become rather skilled at putting on a bra as well as taking it off. and my expertise is being noticed; the other day my love mentioned what appears to her to be my infatuation with brassieres. 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, my love 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, cock cage and nothing else and get her strap-on ready. She came to me wearing nothing but Her own bra and once the strap-on was secured onto Her, she unlocked my cock. Then I found myself on all fours in front of her; she impatiently poking 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!"
— adapted from anonymous