Becoming A Crossdresser

First shot at writing, the following events of this series are a mix of true events and fantasy. Up to you to figure out what is what. I will see what the feedback is like to see when the next chapter will be posted after making the required adjustments.

At 23 years of age, I find myself in a position that I never thought I would be in. Living life as a successful crossdresser who runs CD/TG theme nights 3 times a week for a local swingers club and being a hit on live webcam chat pages. However, I guess I shouldn't be too surprised this is where I ended up. My physical appearance since I was young had always been girlish, if not downright feminine in every regard, and from the first time I watched porn and got sexually active, all I could ever think about was being in that "female" role. It just turned me on so much thinking about handling some man's big cock, and having his hands all over me as he fucked me like a dirty little slut (since then I have also grown to love a dominate female with a strapon too). Anyways, without further delay I will bring you back to where this all started, back in my freshman year of university.

Getting to university for me was like a new chapter in life. I was hoping to escape the misery that was high school. You see, I wasn't that popular handsome jock. In fact was I quite the opposite, I stood a very slim 5'2", 110lbs and to make matters worse, my facial features were very feminine. To add insult to injury, I wasn't packing much between the legs either. A thin 4" erection and basically just the mushroom head would stick out when I was soft. Fortunately, about a month into the school year things do brighten up, and this is where my story begins.

It all started with an innocent search of the area on the internet looking for anything related to the LGBT community. Fortunately for me, I found a clothing store that was dedicated to the TG and CD population in the city (thank god for being in a big city school) and I decided that during my first weekend off, I would go give it a visit.

That Saturday morning I was nervous as hell, but I still found my way down to the shop slowly. Once inside, I was like a child in a candy store. They had everything from dresses to skirts, pencil skirts suits to casual day wear, and every type of underwear you could imagine. I was so lost in awe of the place I didn't even realize the shop keeper had come up behind me until she spoke up.

"Hi, my name is Sharon, is there anything I can help you with today" she said.

I answered shyly, "um, I'm not quite sure...... kind of my first time......"

"Well, how about we start here", she took me to the dress aisle and asked "is there anything that catches your eye?"

All I could do was point at a black, fitted, knee length dress. There was just something about it that I couldn't take my eye off of. After that, we headed over to the bra and panty section where she asked me the same question. This time, it was a pink with black polka dots bra and boyshort panty set that caught my eye. By this time, I was getting a little more comfortable and was able to ask her about a pair of breastforms and a wig. She helped me find a cheaper set of each that would still give an amazing finish but wouldn't cost me too much incase this for some reason became a onetime thing. At this point I was giddy with excitement but I still felt like I was missing something and it caused a bit of uneasiness in me. As we were walking up to the checkout machine, the store keeper noticed and asked, "Is there anything else I could help you with? Perhaps something over in this end of the store?" I looked where she was pointing and it was towards a small section of adult toys and all I could do was shyly nodded again. Sensing that I had no idea where to begin, Sharon took over and suggested that I get a small butt plug and dildo to start with. As she put it, "You should probably start small with something you can handle."

After explaining to me how to use the butt plug and dildo in duo so that I didn't hurt myself the first time I tried, she rang me up and I was on my way home. It must have been the fast 20 minute walk of my life. I just couldn't wait to get back to my room to try everything that I had just bought at the store, especially the butt plug and dildo.

Once in my room with the door safely locked, I grabbed the "cleaning kit" and went to prep for some fun. As soon as I was done there, I raced to the dildo and butt plug and tore them out of their package and tossing the garbage aside. With the toys in one hand, and the lube in another, I lay down on my bed and got ready on my back. First I slowly started to lube the butt plug, making sure to get it nice and wet, and with the extra lube on my fingers, I started to tease my hole and finger fuck it for the first time.

I gently slid my middle finger in, thrusting slowly at first, and using my other hand to play with my tiny soft cock. I don't know exactly how to describe the sensation, but all I knew at the moment was I wanted more. I needed something bigger in my ass, so I worked a second finger in slowly, into my now not so virgin hole. As I was fingering myself, I started to spread my legs further and further in anticipation of the butt plug. As I felt myself loosening up a bit, I grabbed the butt plug and positioned it at my hole, and after slowly removing my fingers, I started to push it in. The feeling of it going in was like nothing I ever felt before. I nearly came on the spot with it less than a quarter in. As I regained some self-control, I slowly started to fuck myself on the butt plug, gaining a steady rhythm of thrusting in and out. At this point, I stopped playing with my now rock hard cock and instead went to play with my nipples, twisting and pulling on them while I fucked myself on the butt plug. I continued on like this for a few minutes until my arm bumped into the dildo as I was playing with my nipples. It didn't stop me from fucking the butt plug, but I couldn't help it, so I grabbed the dildo and started sucking like the porn stars I saw in the movies.

At this point with the butt plug almost 3 quarters way in me, I was hornier and more worked up than ever. I was just like those porn stars, one in the mouth and one in the ass. I was so hard, and horny that I was leaking precum and I hadn't touched my cock in what seemed like forever but it didn't matter. I started to thrust the plug harder and suck on the dildo with even more vigor and lust. And then it happened. As I buried the butt plug as far in me as I could, the biggest orgasm I have ever had in my life hit me. It was wave after wave of pleasure as I shot cum everywhere. I had never dropped such a big load in my life before! It was all over my stomach, right up to my chin, dripping over the sides of my body and onto my bed sheets.

Being as horny as I still was, I decided to scoop up a hand full and eat it, just like the pornstars that I watched and admired so much. Let me tell you, it was a bit salty, but there was something about it that made me want more, almost like I craved it.

After I completely regained my senses, I decided it was about time I went to the washroom to clean up (thank god I was in an apartment style dorm and hand my own washroom). I left the butt plug in as I walked over, and noticed the most interesting thing. The butt plug caused me to sway my hips in a very feminine manor. That left a mischievous grin on my face as I looked back at my female clothes and thought how much fun this was going to be.