Confessions of a Crossdresser

Erica’s reveals his REAL life crossdresser  secrets for the first time

Erica says, “I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself”…read on to discover…

I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing as a female, masturbation, and inevitably, seeking men to please.

I started out as a pre-teen as a panty fantasizer and have progressed to where I am today. I do not consider myself gay, and outside of my fantasy character, I am attracted to women, not to men. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a family. But, I have evolved to a cock sucking crossdresser (sorry for being so graphic).

I’m writing this to try to understand how I have evolved.

If I was a woman, I would be intelligent, attractive, clean, classy, a good dresser, subtly sexy, and fit… but obsessed with pleasing men! I have been unable to control myself wanting to be a woman.

But, I am a crossdresser. I’m married, with kids and I have even been through years of therapy, first for the pornography, and then for the crossdressing. I love my wife and want to stay married. The reality is that I enjoy dressing as a woman, including make-up and a wig. I find this “fantasy” personality dangerously exciting. I like to call myself “Erica”, or sometimes, “Susan”. I think my wife suspects, but we have never talked about it directly. I didn’t intend for this to happen; it just did, and I’m still a work in progress.

I’m not passable, and admit that, although I try to look attractive, I am not in a position to take hormones, shave myself smooth, or otherwise become the woman I fantasize about.

I’m just a normal guy. Well, for the most part…

Here is my story…

The beginning “history” is my best recollection of my crossdressing, from young adulthood until 2004. I started out not really thinking about what I was doing, or why. Later in my “dairy” files, I transition to real-time recording of my acting out as I evolved into role playing as a woman. I love it so…

Wet Dreams to Driver’s License

I had no clue what was going on when I awoke after my first wet dream. My pajamas were a mess, but I felt good somehow. I wondered if I had wet myself. I just didn’t understand. Finally, at a Scout campout, I overhead some boys talking about having “pop parties” and “jerking off”. I realized that they were talking about becoming a man and how one’s penis grew into a sex object. A “pop party” was where a small group of boys would all jerk off and race to see who could climax first!

I was too scared to ask any questions. I had 7th grade health class where they talked about “intercourse” and how boys were different from girls. I heard about “getting pregnant” and about “VD”. I noticed girls developing and starting to wear bras under their blouses. Then I discovered the pleasure of having an orgasm.

I can remember learning about how to fantasize and pleasure myself while looking at the women’s underwear photos in the Sears catalog (yes, this was many years ago). Some of them were very sexy for a teenage boy. I particularly enjoyed the matching bra and bikini panty sets, and the pale pink and blue baby doll nighties.

I masturbated regularly behind the closed door of my bedroom as I looked through the catalogs. I don’t know how many boxes of Kleenex I went through! I have loved woman’s panties, bras and intimate apparel ever since.

Then, on the way home from high school one afternoon, I stopped at the local convenience store. In their magazine section was an assortment of “girly” magazines! On the front cover of “Club”, was the most beautiful girl I had ever seen: reddish blond shoulder length wavy hair, bright green eyes, innocent smile, arms crossed over her smallish breasts as if to hide them, and wearing a pair of sheer, white, lace paneled nylon bikini panties! My cock hardened on its own. I could have cum right there! I bravely took the magazine to the woman cashier, she looked at me but didn’t say anything. I secreted that magazine away, rushed home, and jerked off looking at the cover and inside photos! Awesome!

Once, my mother walked in on me. I had a Sears catalog open to the panty page and I had a Time magazine open with photos of the inside of a Playboy Club, complete with a photo of several topless Bunnies sunning themselves on the roof top. These were “real” women who obviously wanted sex! I was jerking off, using my usual tissue, when she came in.

I quickly rolled over and attempted to close the catalog. She may have known that I was looking at the pics, but I don’t think she knew that I was jerking off. Nothing was ever said. I tore out the Playboy Club photo of the bare breasted beauties, rolled it up, and hid it in a secret compartment of my desk lamp. Between the catalog photos, my porn magazine, and my Playboy pic, I had hours of fun (okay, “hours” comprised of 3-5 minutes of masturbating!)

Then, I discovered the real thing: panties in the clothes hamper! My older sister had several pairs of frilly bikini panties, my favorites were a pair of pale pink ones with white lace trim.

I used to take her panties out of the clothes hamper while the shower was running to cover any noise. I would put them on and jerk off as I watched myself in the mirror. I loved the soft feel of the panties against my cock, and the look of my hard-on stretching against the front panel of the nylon. I would stand in front of the mirror and watch myself. I could shoot a multi-spurt fountain of the mysterious liquid and almost hit the mirror, if I wasn’t careful. Looking back, I guess this was the beginning of my cross dressing lifestyle.

When she wasn’t home, I’d also go through my mom’s stuff and put on her stockings and bras. Panty Hose hadn’t totally taken over at that point and she had gartered stockings. I ran some of her hose trying to find a way to configure a makeshift garter belt, so she may have known of my exploring. I never got caught, but I sure did enjoy dressing-up. I still don’t fully understand why I have this fascination with panties, bras and sexy lingerie, but I am certainly hooked.

I also enjoyed lying in bed masturbating when I could hear the bed creaking when my parents had sex. I tried to listen to hear what was being said, but I couldn’t really tell. I could hear some laughter, so they must have been enjoying themselves. Anyway, it made me hard, and I would jerk off.

Even during these early years, I did like to masturbate a lot. I could cum 3-4 times a day if I wanted to, and I frequently did. When I was jerking off, I could shoot my load up my chest, not quite reaching my chin, and fill my belly button with cum. I wanted to taste it, but couldn’t bring myself to do so. The erotic idea of tasting my own cum would evaporate just as my climax came to an end.

I found it exciting thinking about being caught whether it was in my bedroom, in the shower, or going through dresser drawers. As far as I knew, no one suspected my explorations. And I’m not sure I fully understood what I was doing.

I wanted to taste my own sperm so bad, but I was scared. I didn’t want to think of myself as “gay” and I was worried that it was a perverted thing to do. I could cum in a big way and could fill the little bathroom paper Dixie cups half-way with sperm! Right after I had climaxed, I just couldn’t get myself to drink it! I did dip my finger in and then taste the warm, white liquid, but I just couldn’t make myself tip the cup into my mouth.

I masturbated at home regularly. But once, in the need for excitement, I took my new Polaroid instant camera with me on a bike ride in the woods. When I was alone, I stopped. No one was around and the woods were quiet. I unzipped my jeans to reveal my stiff cock, pressing against the nylon of my sister’s pink panties! What a thrill! I took photos of my cock and the panties with the instant camera, and then couldn’t help myself, and I jerked off, my seed shooting into the wilderness! To my regret, I wasn’t able to snap a photo at the moment of my ejaculation, but it wasn’t for the lack of trying! I just couldn’t cum and take the photo at the same time. I enjoyed the feeling of the panties under my jeans and cumming in the open air. I thought about tasting my cum all the time, but right after orgasm, this just doesn’t seem to work. I guess one could consider this my first journey out in public as a newbie crossdresser! And my first sexual self-photos! I was more worried about not wanting to be “gay” than what I was really doing wearing female underwear. Was I a fag?

Confessions of a Crossdresser