Jessica’s First Time

My experience is a bit scattered (as I imagine many stories are).

My absolute earliest memory of being intrigued by female attire (and why there was such a strict line between male and female clothing) was looking at my mom's heels in the closet when I was maybe 5 or 6 and looking at one blouse in particular. I think she mostly wore it during Halloween; it was a super shiny reflective silver top and I remember thinking how cool it looked reflecting so much light. All my shirts were dull fabric t-shirts.

Fast forward, oh maybe to age 14 or 15… My older brother had many girlfriends, and I remember trying on bras that were left behind; that didn't really thrill me much. Then this one time a girlfriend left behind an earring (couldn't wear it of course, just held it up to my ear and pretended) and a scrunchie (hair wasn't long, but I put it on my wrist as a bracelet which many girls at the time did when they let their hair down).

Then there was the holy grail of clothing, black nylons. I felt the fabric between my fingers. I wanted to try them on so badly, but I knew she was skinny and I was a somewhat plump kid. I didn't care, I had to know what they felt like. After putting them on I won't lie, I got excited. So much in fact that I "went" without even touching anything. I believe that ingrained my transgenderism, but more importantly my crossdreaming.

About a year later, my brother finally convinced my dad (parents divorced for a few years at this point) to let his girlfriend to move in. This was both a blessing and a curse. Blessing because I now had access to female clothing on a regular basis (a beautiful woman, in fact).

It was a curse because she too was smaller and I had to be very careful how I put things on. The worst sound in the world is stitching stretching until it makes that sound of cracking, which was the point where you take that article of clothing off, hang it back up and pray she doesn't notice. I remember a moment when she was arguing with my brother about how the washer and dryer was somehow ruining some of her clothes and stretching them out. I don't think I had felt more guilty up to that point in my life and to this day, I never confessed to it.

Of course, this only led to me wanting to acquire my own things. About age 17, I was entering local community college and had a part-time job while still living at home. I decided to acquire a PO box so things wouldn't be shipping directly to me at home. That way I could get female clothing catalogs like Lane Bryant and Fredericks of Hollywood delivered to a discreet mailbox and begin ordering clothing.

I could pick-up my order at the post office, walk into my room and hide them away. I had exciting moments in my life like anyone, nothing could possibly top placing an order for dresses and stockings, and then waiting the 5 to 7 days for those items to arrive. When it got closer to the time I thought it might arrive, I would stop by and check for a notice everyday (this was the days before tracking notifications to know when it was delivered).

I rented the smallest box I could get knowing if I had packages, they would store them in a bigger post office box for delivery. When my bag of clothes finally arrived, I rushed over to the box, opened it, grabbed the package and nervously put the key back in. I threw package on my front seat, not even opening it up to sneak a peek.

I arrived home, and my dad either wasn't home yet or he was sleeping on the couch like he often did since he worked third shift. I rushed into my bathroom, pulled that black dress out and excitedly tossed it over my head after I removed all my clothing. It was a cheap dress made mostly of nylon, but that shape hugging my body and giant flowing neckline in front was like nothing I had experienced before. It was probably on par with the first “oh.” It felt like a woman was wrapped around my whole body.

Since I had the typical bathroom with the giant mirror attached directly to the wall, I looked at myself and couldn't believe how just a dress could change my look so much. I remember getting weak-kneed and having to sit down on the toilet from excitement and just bending over with pleasure of how I finally got to enjoy this feeling for the first time in my life.

For years I collected all sorts of female clothing from bras, wigs, makeup, leggings, shoes, etc. I kept it all in a big cardboard box at the back of my closet buried under other miscellaneous boy things and my dad never found any of it.

To this day, neither of my parents know about my secret life. Only my wife knows my secret.

I invite all femulators to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Wearing Polo.

Actor Patrick Stewart