The Making of Monica

I knew. Looking back now, I realize, I always knew. I just never did anything about it, until I was ready mentally, emotionally and physically. I was born Matthew J. Smith in the mid 70's in middle America USA. I grew up in an off beaten, middle class, mid-sized town in the center of the United States. My parents, as loving as they could be, were not the best of role models. Most of the time my father was drunk and my mother always seemed to be ironing something or making dinner. I spent my time playing in fields, in barns and along the creek, usually alone and trying to find my place in the world.

I was always smaller in stature, blonde hair, deep green eyes, with a skinny physique. I was always the person nobody picked for their team. The person that was always on the outside looking in. The person that didn't have many friends and the person that (secretly) was fascinated by women's clothing. I couldn't tell you how many times I saw intimate women's clothing hanging across clothing lines on the houses in my area. My mom's bras were intriguing and as much as I was dressed in bell bottoms and a vest -- the fashion of the that era - I knew I was longing for something different.

I would spend hours thumbing through the Sears and Woolworth catalogs looking at women's clothing. I'd pretend I was looking at toys or boy clothes, but every time I saw a long skirt, or a fancy dress, I felt sensations throughout my whole body. I loved how the model's looked, their hair, their make-up, their thin sexy bodies. I was enamored in things I couldn't even begin to fathom.

I did manage to find girlfriends time to time and just after, "I became a man", I lost my virginity to a long-time girlfriend. It was amazing being with her, but as the years went on and we went off to college, our relationship ended. I dated in college and I guess for the time and that point of my life as it was, I was "successful" with women. When I graduated, I wasn't going back home. There wasn't anything in that town for me. There wasn't a happy homelife to go home to and there surely weren't any good jobs.

As the 90's came to an end, I found myself in southern California. I went there with a friend from college who was bound and determined to get me away from the farm life and get into a big city atmosphere. I stayed with her family while I was finding a job and getting a place of my own. I managed to land a decent job in advertising and shortly after, secured my own little apartment in big city America, but something was still missing.

Wearing Nancy's panties.

The first girl I dated in California was this tall, fairly big-boned girl named Nancy. She was just a bit taller than me, had big voluptuous tits and had hips that spread a mile wide. She was a constant in my life and as much as I loved her being around, I still found my heart longing for something else. But I didn't know what? As our relationship developed more, Nancy would spend long weekends with me. She'd leave behind her dirty laundry by me and I'd wash it for her and that way she had a change of clothes at my place.

One night at the laundromat, I was washing her stuff (as usual) with mine and I pulled a pair of her panties out of the dryer to fold them up. The feeling of holding her silky, cute pink panties in my hand, lit a fire inside me I had never felt before. I was mesmerized holding them looking at them and feeling the soft smooth material in my fingers. I didn't know it at the time, but those panties began to change me.

I started to feel horny, I felt excited, I felt dirty, but most importantly I felt like they needed to be on me. I wanted to wear then, I wanted to feel what it was like to have a hot tight sexy pair of women's panties touching my skin. Holding in my dick and balls in; and how erotic it would be to sleep in them.

I must have looked like an absolute pervert in the Laundromat. I know I was licking my lips, staring at these panties, holding them up, feeling them. I realized what I was doing and I quickly folded them up, placed them in my basket and finished gathering the remainder of the clothes from the dryer and getting out of there. I felt like I was in the spot light and everyone in the place was watching me. I rushed home almost in a panic, feeling embarrassed being caught fondling Nancy's panties.

As I started putting all the washed clothes away, and as I got to the panties in the laundry basket, the fantasy and feelings began again. How sexy they were, how hot they looked, how unbelievable they felt in my hands. I couldn't fight it, I had to put them on. My heart raced and my stomach was doing flips as I walked into the bathroom, dropped my pants and boxer shorts and slid them on. The feeling was overly erotic, dirty, sexual, stimulating and amplifying. My dick got partially hard and I could not concentrate on anything but feeling those silky, sexy panties on.

I continued putting the laundry away wearing her panties. I walked around my place, got a bite to eat, got ready for bed and eventually slid into bed wearing them. I tossed and turned forever that night, feeling how close, how tight and how comforting they were. There was something inside of me screaming out in lust, in pleasure and in longing while being in them. I felt like I could slide across the mattress in them. They were surely tighter than men's underwear, of course they were, they're not made for men, but what an incredible feeling to be lying in them. I couldn't sleep. I was so horny, so turned on, so aroused and so overwhelmed that I finally had to masturbate in them.

I slid my hand down over them, just feeling the silky-smooth material, holding my dick and balls in. I rubbed around them, up and down them, around to my ass cheeks, just feeling how incredibly sexy they were. How hot they felt, how erotic they felt on me and how much I felt more alive -- at that second -- than I had in a long time.

Finally, I slid my hand inside of them. My cock was rock hard, sticking straight up and bulging. I cupped and pulled on my balls. Dry stroked my cock. Ran my hand around to the back side grasping my ass cheeks. Tossing and turning, rolling backwards and forwards. What was going on with me? Why was I feeling this way?

I was ready to explode already. I stroked myself inside the panties, I never slid them off. I wanted to feel myself inside them throughout the whole fantasy. I masturbated slowly for a length of time, spitting on my palm, time and time again, getting my shaft soaking wet and slippery. I was taking in every feeling, every sense and every thought. I wasn't thinking about anything but those sexy pink panties wrapped around my waist.

When I got close to cumming I'd stop pulling myself and would just rub up and down my crotch, just feeling my hard cock bulging inside them. How my balls were cupped and were sitting slightly higher inside the panties, than they sit in my regular underwear. How sexy it felt to rub my hand over my crotch feeling a hard cock and balls, instead of Nancy's pussy. I felt desires and passion I had never known. My asshole tingled, my cock throbbed and my body was releasing hormones, I had never felt before.

When I couldn't take it anymore, I started stoking myself again harder and harder, feeling the tightness of those panties wrapped around my skinny little body. I came inside the panties exploding all over the inside top of them and all over the top of my hand. I came hard, long and in the most sensual way. I was hooked. There was no doubt about it.

As Nancy would come more, I would talk her into leaving more and more stuff by me. It wasn't long until she had more panties, bras, pajamas, shirts and boy shorts in her own little dresser in my apartment. And It just started with the panties, but then as I became more brave, more adventurous and more open to wearing other things of hers that I could fit into, things changed. And it wasn't long until I was wandering around in her bra's, her panties, her shorts and her favorite night shirt. I'd wash it all again, before she came for her weekend and since she was just as big, if not bigger (in certain areas) than I was, I never stretched any material out, so she had no idea that I was wearing any of it.

Every time she'd leave, I would almost instantly get into her articles of clothing she left behind and wear them all week, only to quickly wash them Thursday night before she'd come back over the weekend. I was enthralled. I couldn't get enough of wearing her panties under my jeans, have her bras wrapped around my chest, with two pairs of socks in the cups to imitate tits. I'd wear her favorite night shirt to bed and jack-off almost every time, as to alleviate my overwhelming desires. But I wanted more. I just still didn't understand my passion, my desires and my needs.

In my mind I justified wearing her stuff as a way to be closer to her, when she wasn't around. To feel her love, be in the things she wore, as a remembrance of an erotic, loving night with her. But, when Nancy and I split about two years later, I didn't want to return her stuff. But she came and took all of her belongings back and I went on with life. Nothing seemed to help me feel the way I did when I was wearing her clothes. I started to believe that my passion wasn't for the clothes, but for her. Only to realize once she had left and those clothes were gone; it wasn't her, it was the clothes.

I set my sights on finding my own stuff, but I was way too embarrassed to go into a store and buy women's panties and bra's. Let alone pantyhose, high heels and lingerie. My mind was racing on things I wanted. I'd spend hours on line shopping women's clothes, but could never hit that "buy' button and have them shipped.

To relieve my stress and anxiety and to have comfort knowing that some women's clothing were inside my apartment, I started dating only bigger girls, like Nancy was. I'd talk each of them into leaving clothes at my place. A few were really open to my suggestions, while others thought it was weird that I wanted to do their laundry. I tired to play it off as, "If I left my stuff at your place, I'm sure you'd wash it". But in the end, it never panned out in the length of time I dated Nancy and the number of items, she was keeping by me. And nothing as erotic, sensual or as pleasing as Nancy's intimate apparel.

It was time...

I knew it was time. As embarrassed, shy, perverted, or even psychologically wrong as I thought it was. I knew it was time. Through online shopping, home delivery and access to every thing I wanted via the internet I started to acquire my own items. Slowly at first, but gathering more and more things... some fit, some didn't... Some were hot sexy night club clothing; others were your everyday wear items.

There was no doubt about it. I knew. I started to accepted it; and I realized, wholeheartedly and undoubtedly, I was a crossdresser.

I'll tell you all about my transition and the making of Monica in the next few chapters.