The Awakening, Ch. 01

Ok, I'm "back in the saddle", with a story that I feel many of us have lived. All are over 18. Comments, as always, are welcomed.

I didn't start out wearing women's clothes, but, as far back as I could remember, I was fascinated by sexy dressed women. Short skirts, thigh highs, high heel shoes got my attention instantly. I would steal my sister's clothing magazines anytime I could, and, before you ask, yes, I would sneak peeks of her, in various stages of undress. What red blooded boy didn't? The first years of my life, I chased girls, landing a few. Don't get me wrong, I loved it. The first blowjob I got? I thought I'd died and gone to Heaven. First girl I got to fuck? Pretty much the same. I DID learn, though, all girls were not created equal. NOT by looks, but by desire. A few seemed to enjoy sex, but for many, it was just an unstated obligation. So, the novelty wore off some. Yes, I still took any opportunity to score, I just didn't set any expectations. If I got lucky, cool, if I didn't? I knew I could go home, lock my bedroom door, and log on to the internet, and escape reality.

The internet can be a blessing and a curse. SO much there to feed a horny mind. I think we ALL start with vanilla sex, then "branch out". You know, each new door is a "what the fuck" moment, but, you find yourself going back...and back. Until that, too, gets bland or boring, so you explore more. As fate would have it, my sister went off to college, JUST about the time I stumbled upon Boys in dresses. Only, THESE boys could fool their moms, I swear. Amazingly beautiful, only, with cocks. I wasn't attracted to their cocks, as much as amazed that they could look SO completely female, but for that one thing. It wasn't long before I obsessed over "chicks with dicks". It was all I watched. One thought overrode all others. WHY is it that girls dutifully suck cock, or fuck, but femboys absolutely CRAVED sex. I needed to know why.

Oh, yeah...and back to my sister's absence. I'm quite sure by now, you know my curious nature got to me. It started with any measure of time that I was home alone, I would explore her room. Ok, not her ROOM, but the contents within. Does EVERY brother with a sister go through her things? Tell me yes, even if you have to lie. Because I sure did. At first, it was just LOOKING, touching, then, jerking off in undies, and eventually, trying them on. Geez, that was almost as good as sex. SO soft, smooth. I was conscientious about washing EVERYTHING I touched, or, more accurately, USED, so my mom wouldn't notice, or my sister, should she pop in home. Wearing her undies became a daily thing. This actually went on a few months before I went waist deep in the deviant pool, and decided to try dressing. Her pantyhose (which I later switched to stockings, mostly because they are so sexy), then one of her dresses, and, even though they were a size small, heels. I played for HOURS! What a rush. I spent EVERY available free, alone, hour, being someone else. THAT phase went on for several months, before I got brave enough to try her makeup.

Oh! the first attempts? NOT pretty. I looked like a Rodeo clown. Still, I was patient, methodical. I studied Youtube video after video, gleaning every thing I could, until I could finally look in the mirror and not cringe. I felt I looked enough like a girl. It upped my playtime fantasies a hundred fold. I really thought of myself as the girl in the video, getting fucked, instead of the guy filling her ass.

The NEXT big step was going to a department store for my OWN makeup. I knew that if I used up all my sister's, they would catch on. I went to a store on the other side of town, where I felt safe that no one would recognize me. I purchased everything I needed, but, as I was walking through the women's department, I saw fake breasts. Realistic, in every size you could imagine. I was not braze enough to buy any, but rushed home, found them online, and ordered a set. I didn't want to go crazy, so I got B cups, with extra adhesive. I had been filling out my sister's bras with rolled up socks, but was anxious for "my" breasts to get here. Having something that FELT like the real thing excited me, the days seemed to crawl by. Luckily, no one else was home when I got a notice of a delivery. I was already "dressed", and had to be careful, peeking out my door, making sure no nosy neighbors saw a strange girl opening our door.

I literally ripped the package open, quickly scanning the directions, before pulling my dress off my shoulders, and pulling my (I know, not really "MINE", but by this time, I was claiming ownership) bra up, and brushed on the adhesive. It took a few minutes, trying to position them just right, THEN more minutes making sure the adhesive had enough grip. I stood in front of the mirror, gazing at my new body. I twisted and wiggled, and yes, fondled myself. I LOVED the weight of them. I immediately start thinking of ways I could leave them on, without getting caught. I zipped my dress back up, and almost cried with joy when I saw my reflection. It had taken months, but I knew in my heart, I could pass... IF... I could get the nerve to go out, in public, AND, WHERE would I go?

Well... NOW what? In all my preparation, I hadn't considered how far I was willing to go. In my fantasies, while watching the trans videos, I had imagined me being the girl sucking a big cock, and getting filled with cum, but, COULD I? If you had asked a year ago, if I'd suck a cock, or even WANT to? Hard pass, but now, LOOKING like this, and FEELING so feminine, the idea was growing on me. Looking in my mirror, I'D fuck me! Would someone else? I felt that this is the process femboys go through. I figured that few gay guys actually went into dressing, unless it was to make money in the "drag" shows.

I went back to my computer, checking the trans sites for possible meet-ups. I went into SEVERAL chat rooms before I started feeling at ease. It's easier to be brave behind your keyboard, instead of in front of a real person. I quickly learned that I would need a personal name, obviously NOT my male one. I tossed names around in my head, from the typical porn names, to plain Janes, and finally settled on a derivative of my name, Shane, to Shana. Easy to remember. So, SHANA started jumping into the flow of conversation. I was amazed at the response, when I exclaimed that I was new to dressing, but eager to meet people. (Yes, I left it vague) Of course, there were crude ones, I expected that, AND, it seemed EVERYONE wanted to see pictures.

That made sense, why hadn't I thought of that? So, I stepped away, grabbed my phone, almost ran to the full length mirror in the master bathroom, and took several, in various poses. Nothing too risque, but a couple did feature my long slim legs. I hurriedly loaded them into my profile, and my computer blew up. 400 responses in 20 minutes? Could that BE right? I popped back in the chat room, where suddenly I was overwhelmed by personal chat requests. I was flattered, mostly, even from the scuzzies that were nothing but lewd. I mean, yes, I'm considering sucking cocks, and offering up my virgin ass, but, DAMN! I want to feel like a pretty girl getting hit on, NOT a piece of meat. I did the "BRB" in the chat room, and one by one, opened the private chats. Most, I closed quickly, but did chat with a few guys.

All of them went from ages 18, to even a 60 year old guy. Um, he seemed nice, but, I just couldn't see myself sucking a granddad. I finally trimmed it down to three chats, all well mannered, and seemingly very interested in meeting me. One was single, one divorced, one still married. I started to close that one, but he said his wife had no interest in being feminine, and wore very androgynous clothing and, over time, marriage was just stale. I kept his personals, to consider that. All three, though, had stumbled into the femboy porn thing like I did, and were intrigued how a boy could look so much like a girl. I liked that. All three ALSO were very complimentary about how much I looked like a real girl. Besides bolstering my ego, it wired up my hormones. When we DID veer into talk of sex, not one wanted to suck cock, they wanted a "girl" who would like it. I told each that I had never tried it, but was at least open to the idea. Quite honestly, the more I thought about it, the more I WANTED to know what it would be like. The anticipation was nerve wracking. I looked back on the blowjobs I'd received, and tried putting myself in her position. I could DO this!