Jealousy

I had a sister who was 2 years younger than me, who I felt got coddled, while I was always held to a higher standard as the first born. Like, I'd get four A's and one B on my report card and all my Mother would want to know is how come I didn't get all A's. And I had a lot of chores to do, while my sister had very few.

One day when I was around 12, just as puberty was about to begin, I was home basically alone. We lived in a 2-family house and my grandmother was in the other apartment. Anyway, I went into the bathroom and for some reason dug through the laundry hamper and found some of my Mom's things including a girdle, bra and stockings. They felt silky and sexy to me; I always enjoyed the feeling of silky things even as a little kid. For some reason I was always very tactile. Something compelled me to try on my Mom's undergarments. When I put on the girdle I instictively tucked my little penis between my legs. I had an incredible feeling that I never had before when I rolled those silky hose up my legs and attached them to the gridle's garters as I had seen my mother do many times.

Once I was dressed in her undergarments I really wished that I was a girl so that I would have an easier life. I naively decided that if I could get rid of my penis I would then have a better life. So, I decided to try to crush my penis, which was still tucked between my legs, by straddling the rim of the bathtub and trying to rub it away. As I am sure many of you can imagine the rubbing led to an earth shattering ******. The first of many more to come while dressed in female garments. From that day forward I loved to dress and ********** as often as I could. I was forever hooked on cross-dressing and the incredible feeling that I got by putting on silky and sexy female garments.
Sassysuetv Sassysuetv
56-60, M
11 Responses Nov 26, 2012

My aunt gave us a box of hand me down clothes when I was a teenager. As I rummaged through the box I found a body suit. It had a built in bra and a snap crotch. I started sneaking out at night wearing nothing but this body suit. I would walk down the street dressed in just lingerie. This would almost always result in ******* after which I would go back home, take it off, and sleep like a baby.

My mother started me wearing panties and nighties. Because she raised me as a girl for the first six years of my life.

I had similar experience except I was six or so but no ****** of course. In time I was caught, and everything took a strange twist.
I have no regrets, I wrote a book about it. It's called "He's my Little Girl". You can Google the intro if you wish.

Thank you for sharing your story, a very interesting start . I cross dress, but never had a cathartic experience such as yours.

Glad you didn't rub it away.

what we can do in teenage ifour moms dont have so sexy lovely sweet lingere,nowadaysmy..w......she ha sno idea what woman must wear ,,, so Sasa wearing all sweet womans lingtere cloths .heels ,mmmm so lovely

I too discovered how very nice my mom's panties and nighties felt on my **** and balls and have been playing in lingerie ever since.

i found mom's split crotch girdles years ago--wish i still had them. love panties--sleep in them all the time

So sweet and innocent. Liberate yourself with what you know about how this all started. Sort the fallacies from the facts, take what is best about who you are, and celebrate it anew, while you still have life pulsing in your loins and heart. Try to have a little fun while you still can, honey. It's never too late to go fishin' :)

Wow that could be my story!

my wife knew I had feminine inclinaitons and as she discovered me to be more feminine she handed me panties to wear informing me I had earned the right to wear them

Well that was the way i started my sisters night gown and the top of the starirs to *** and wearing bras with stuffing and jumping on the bed to mash my boobs

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