The Making of Monica Ch. 02

Moving forward.

After Nancy and some of the other girlfriends moved on, I started to do a bit of soul searching. I had begun to realize I felt more comfortable and surely more turned-on wearing women's clothing. I started to accept in my own mind that I was a crossdresser; or at least that I liked wearing women's clothes. I wasn't sure why, or even knew what caused this sudden change. All I knew was I wanted it. I desired it. I needed it. I still loved women, still loved being with them, but I wanted someone to accept me for who I was, but I was still searching for who I was. As I now know from experience, (in a lot of cases), most women do not want to date crossdressers. So, for a while I broke off all dating. I kept to myself and just began to comprehend where this lifestyle and this change would bring me.

I started ordering more clothes online. There were days I'd rush home from work to find packages in the foyer of my building for me. I'd haul ass up to my condo, drop my stuff and start ripping boxes and envelopes open. Panties, Bra's, Nightgowns of varying colors, designs, lengths and styles were coming in faster than I could comprehend. I had already - at that point -- acquired more clothes than Nancy or anyone else had ever left at my place. I bought a second big dresser and had drawers full of panties, matching bras, body suits and alike.

But I was still missing something. I started looking up crossdressers and crossdresser lingerie online to see what they were wearing. What they looked like and what fashions stood out. I pondered on what would fit my physique and look sexy on me. I was enamored by the models standing there in a cute pair of panties and bras with their black pantyhose and high heels on. Their panties holding in their bulges, or in some cases standing there with their dick sticking out. I would almost drool at the computer, fantasizing about it all.

That's when it hit me. I needed pantyhose, high heels and sexy negligees. Nancy never left those here, nor did anyone else. But I had never purchased pantyhose or heels and surely never a negligee. I had no idea(s) about sizes, or kinds. I spent hours researching these things online, while sitting at my computer wearing my panties, a bra and a silky nightgown. Hard as a rock, dreaming of what they would feel like, fit like and how erotic it would be.

When thing started to arrive, I would rush to try them on. Feeling how silky they felt along my legs, how unique and exquisite it was to be wearing them. But my hairy legs, would make the pantyhose look stupid on me. But I must say, feeling those silky nylons on my legs and around my hips with a pair of thong panties on, wearing a classy nightgown was so incredible, that I would cum in minutes jacking off.

It was time...

Moving forward I realized that all of the models, actresses, transgender and crossdressers online all had shaved legs and shaved pubic regions. I was a little leery at first to shave my crotch, my legs and around the "back door," feeling like I was leaving a big part of my manhood, being a man, or looking like a man behind. But I knew I had to do it.

I had just ordered some elastic top, stay up thigh highs and a new pair of black 3-inch heels, along with a long black dinner dress (my first dress). And I wanted that moment to be perfect. I wanted to put it all on in one big ensemble and wear it around the house all day. I wanted that moment of drees, heels and undergarments to be perfect. I wanted to look like the "women" online, be clean shaven like them and be sexy like them.

I was committed to making the change, so one night I drew a hot bath, climbed in and I shaved my legs, my crotch, my ass and even my arm pits. All knowing the next day the items I sent for would arrive and I could wear them and be more feminine. I went into work the next day, wearing a thong under my slacks, feeling nothing covering my ass cheeks, coupled with my sexy clean-shaven legs all day, made the day go by way better. With the want brewing to just get home and put all my new arrivals on.

Once I arrived home that Friday night, I ripped open the packages. I slid on the thigh high panty hose, which by the way, FELT AMAZING on my shaved legs; put on a matching black bra, placing some socks in the cups. Pulled the tight dress (unfortunately, I had ordered it about a size too small) over my body and slipped on my new heels. It took me a few minutes to get used to walking in them, my balance was uneasy, as I had never done it before. But after a bit, I adjusted.

I stood in front of my full-length mirror admiring myself. Here I was in a beautiful long flowing dress, nylons showing from the lower portion of my legs, three-inch-high heels adorning my feet and a small set of tits poking out at the top of the dress, like I actually had tits. From the neck down I looked amazing, but the neck up still needed more work.

I was so hard and horny. I was so turned on. I was so ready to meet someone dressed like this. I wanted to go out in the world like this. Go to the grocery store like this. Hang out at a bar like this. But who was I kidding, I was just an average looking guy, still nowhere near passable, standing in the bedroom of my condo, dressed in "drag."

I did my after-work routine that night, dressed in my new outfit. I made dinner, did the dishes and even watched some TV for a while, before the overwhelming desire to get off took me over.

I went into my bedroom and threw on a lesbian porn watching the girls make love. It wasn't anything out of the ordinary, until I got to the scene of two women at a wedding who snuck off to have sex. Their dresses were long and flowing, like mine. They both had on heels and nylons and they both had sexy panties and bras to match. As their dresses fell and the undergarments were shown, I about exploded. Is this what I could look like? Is this what I want to look like?

Their beautiful hair and make-up done perfectly. Their big ample breasts, their tight panties, sexy asses and dripping wet pussies made me want it more. The lip stick, the jewelry, their thin, perfect sexy bodies. Those clothes! Those images! The exoticness' of (not only) the lesbian sex, but slowly undressing each other, out of their intimates. Holy fuck I was hooked. I wanted to be them. I wanted to be in that moment. I wanted someone unzipping my dress. Unhooking my bra, sliding my panties off.

They were hot! And I wanted to be every part as much of a woman as they were.

I reached down under my dress and started rubbing my hands (yes both) over, around, up and down my panty hose, feeling how sexy they felt against my fresh shaven legs. My cock was bulging so hard in my panties, I was pulling the thong string that ran up the crack of my ass, so far into my crack, it was almost hurting. The heels on my feet making my legs complete.

I started dry stroking myself slowly, feeling my cock pulse and throb. My hand gently cupping and caressing my balls, feeling how sexy and erotic they felt hairless. I got off my bed and walked femininely, over to my dresser where I grabbed some lube. As I returned to my bed, focusing on these to women, heavily engaged in sexual deviation, I reached back and unzipped my dress. Letting it fall to the floor. I slid onto my bed wearing, my bra, panties, heels and hose.

As I watched the scene more, the girls were naked except for their thigh high pantyhose and heels. I wanted to emulate them, feel like them and be them. I slid my panties off, letting my cock pop free, but leaving everything else on. I squirted a generous amount of lube on my hand sliding it up and down my shaft. I cupped and grasped my sock breasts, feeling the bra cups, the material and the socks in my hand as if I was playing with my own tits. I stroked myself deeply and thoroughly, until I came all over my stomach. My toes curling and sliding back and forth inside those heels.

The girls in the scene were still going strong, as I sat and watched more. And even though I had already cum, I was still stroking myself, in absolute awe. I kept rewinding to when they were unzipping their dresses revealing their intimate undergarments. The seduction, the taboo of it, the lust, the passion, the sexual fire of it all had me engrossed.

My hands shook, my ass tingled and I felt like I had never felt before. Before the night was over, I stroked myself to three orgasms watching these two girls. And through my intimate alone time that night, at times, my hand would slide down past my balls and in between my ass cheeks and I would rub, tease and tantalize my asshole. It was such a great feeling, having my fingers rub around an area, newly discovered and never played with before, while my legs were raised up, my cock hard, watching lesbian porn, becoming more and more; or at least feeling more and more like a woman.

By the time the night was over, there was cum everywhere. On the bra, on my dick and balls. On the top of the thigh high panties hose. There was seven some on my headboard. It wasn't the lesbian sex -- in some ways maybe it was -- but it was more the pleasure of seeing those beautiful women in their beautiful outfits. It was the experience, the fascination and exoticness' of being slowly undressed in women's clothes. It was the feeling of want. Of need. Of succumbing to it all.

I couldn't take it anymore. I didn't know how or why, or even when this fetish took over my life, but I was hooked. I needed more of this. I needed more clothes. I needed tits, I needed make-up, and wigs! I needed everything a woman had. I fell asleep in bed wearing everything but my panties. I awoke the next morning in disarray, but excited I still had my bra and pantyhose on. I needed more feminine time. I needed more things.

I spent the next few weeks ordering myself more clothes, several different sized breast forms, wigs and make-up (I needed Make-up) to complete my ensemble. All of which added up quickly and put me into credit card debt. I went to second hand stores and bought dresses and heels from the sales floor. I bought women's jeans, tops, belts, and a boat load of inexpensive accessories, like rings, bracelets, earrings, explaining to the register clerks that it was for my girlfriend. I don't know they believed me or not. Looking back, I don't think I even cared.

I needed it all. I wanted it all. And I was going to have it all.

There probably weren't too many nights, I wasn't on line, out shopping or watching lesbian porn; dressed in my new clothes, feeding the monster that came alive inside of me and that was now consuming me. Like a drug addict, I had to have it. I was changing and as scary and confusing as it was; I was loving it.

The next deep submersion, the big "next steps" came months later with the un-expected discovery of a helping hand, some online crossdresser friends and Transexual porn. It fostered me more and sent me launching into a whole new direction of my life.

To be Continued...