My crossdressing love life

I remember skipping days of school for orgies of firmly girdled masturbation;

…dressing in my lovely things with my collection of lingerie catalog pictures and centerfolds (and my wild imagination) to keep me company. I’d change repeatedly in and out of my zippered basques and girdles either “borrowed” from neighborhood clotheslines or stolen from the lingerie drawers of women I adored.

Mum modeled for Barbizon and when I came along, she captivated me by feigning shock, [accidentally on purpose ?}, while flashing me with her very firm foundations; Other times she beat me. I was hooked. Discovering the pleasures of self-love, I’d  often lock myself in the bathroom for some quick CBT or to zip up in mums’ very newest satin paneled long leg girdle. Over the years I’ve built up quite a collection of foundations and corsetry and have loved both hard boys in fancy bras and panties and older women who preferred me dressed fem. Now I’m just another happy overeducated professional who dresses daily in my intimate apparel …. swooning when my dear wife laces me tightly in my girdle-corset or loving her deeply for suggesting that I plug and lock up before worshiping her.


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 posts discuss the progress I’ve made in large part because of Her insistence that i practice.  Since then, she’s also mentioned what appears to be her 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, she 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 her 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!


Author unknown

Wearing a Bra – A Feminine Feeling

For most sissies, I think their first fascination with crossdressing involves panties. Panties are also probably the most popular item that helps symbolize or reinforce a Femdom/sub sissy male relationship.   Phrases like “She keeps me in panties 24/7…” are very popular when people describe such things.

I’m no different.  I owned many pairs of panties before I got my own bra, and that bra was “outnumbered” by the various styles of panties I  had for many, many years.  As my cd fetish and submission to Her evolved into a lifestyle, more bras were added, and I was made to wear them more often.

Today, they are part of my everyday wear.  This morning while getting dressed, I thought about the first time I wore one, and how difficult it was to put on.  That first time, I was alone and just couldn’t get the darned thing hooked in the back.  I finally decided to hook it together before putting it on and slid it over my head and shoulders and finally got it adjusted correctly.  My struggle that day was far from feminine in appearance!

Fast forward to when She became more “interested” in what I was wearing and the brassiere became a required piece of clothing for me.  When that time came, I was not much more skilled at putting this lovely piece of women’s wear on.  The solution:  Practice, practice, practice.  One evening, in the middle of our living room, She made me stand in front of her with several different bras and made me practice putting them on like a woman would.  I struggled immensely and my frustrations showed.

She would just giggle and tell me to start over.  Once I would get one bra “hooked on” I was given another to try.  This went on for hours, until I got it just right.  I got the hang of it and by the end of the practice session, was slipping the bras on just like a woman.

This morning as I slipped on the bra I’m wearing while looking in the mirror, I realized just how feminine I look while doing it.  It’s all the result of that initial practice session, and all the practice I’ve gotten since then.


Author unknown