My Life as a Crossdresser Ch. 01

Hi,

This is my first ever attempt at writing a story so I would appreciate constructive feed back. Also, this is just mainly set up and background info with only a masturbation scene. Some of the following events are true and did happen to me.

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It has been five months since I turned 18 and thankfully, high school was in my rear view mirror having just graduated with honors. Being as physically small as I was for a guy (5 feet and 110lbs) you can imagine how much fun it was going to school every day. To make matters worse, my facial features were a bit more feminine then they should've been for a normal teenage boy. I also had a lack of any real facial or body hair but it didn't matter anymore, high school was over forever and I was freed from my torment. Plus, this summer had the makings to be something special. You see, I was a closet cross-dresser and very bi-curious, two things I dearly wanted to explore but didn't have the means to do so until now that I was 18.

The first thing I did when I turned 18 five months ago was get a credit card, and since I was a very shy person, the credit card made a huge difference. It allowed me to shop online and buy the women's clothes and shoes that I wanted so badly without having to go into a store and actually interact with people. Through a bit of trial and error I was able to assemble a few different outfits that fit me perfectly and buy a few pair of high heels to go along with them.

And since my summer job allowed for me to be home alone a lot during the day I found myself walking around the house in women's clothing all the time. One day it would be a skirt and a blouse, another day it would be a nice two piece bikini, but regardless of what I was wearing that day, it made me feel great. It was also during this time that I discovered what I thought to be a very embarrassing fact actually had its upside when I was wearing panties, bikini bottom's or more form fitting women's clothes. Since my cock was so small (only 5 inches hard and 1.5inches soft) I had a really easy time "hiding" it. In fact, even when I was wearing something as revealing like a bikini, to anybody who didn't know any better, I would look like nothing more than a very flat chested girl.

About a week into summer and cross-dressing all day, I decided that I wanted to really explore my bi-curiosity. So one night, after getting dressed normally, I left for work early so I could make a stop at sex shop on the way in. As I got into the parking lot, I started to get very nervous, and sat in my car for 10 minutes or so before I had the nerve to move. When I finally made it into the store, there were one or two people in there and the store clerk was busy helping them out, so I made my way to the section of dildos and butt plugs hoping that nobody had really seen me. I was starting to look at the collection of sex toys and decide which one I would by when sudden from over my shoulder I heard

"Hello, is there anything I can help you with?"

Turning around red faced, I saw it was the sales lady and as quickly and calmly as I could I replied, "Hi, I was just....... Just... looking for.... A dildo.... And a maybe... a butt plug."

She replied, "Is who this is for new to anal?"

I couldn't verbally answer, so I just nodded my head. After seeing me nod, she quickly took one butt plug and one dildo and handed them over to me.

She said, "Well these should be a good place to start. Is that all you wanted?"

I replied "Yes" and a few minutes later I was leaving the shop heading off to work with a 7 inch dildo that wasn't very think, a 5inch long butt plug that had a 2 inch diameter at the largest point and a bottle of lube sitting in my car. The whole time at work I couldn't help but think of how turned on I actually was by the whole situation and how I really wanted to get home to try at least the butt plug that night.

And when my shift was finally over, I rushed home with more energy than usual, and went straight to the bathroom, figuring it would be easier to clean up in there if I made a mess. I quickly stripped out of all my clothes and placed the butt plug on the edge of the bath tub. As I was lubing it up, I was a bit surprised to see that I was completely hard and was getting really excited to try this.

After the butt plug was completely lubed, I positioned myself over the butt plug straddling the edge of the tub. Slowly I lowered myself until I felt the tip of the plug at the edge of my hole. I paused for a moment, and continued, moaning softly as I took in the first inch of the plug. Stopping there, I slowly started to ride the plug up and down, taking in more of the toy and getting stretched further and further on every down stroke. I was in heaven; it felt so good riding the toy. I started to leak pre cum when I made it half way down and I didn't even stroke my cock once. I continued to ride the toy, speeding up the pace, fucking myself faster and faster with the plug. All the while I got more and more turned on and my cock got harder and harder. I continued to fuck myself as hard as I could with the toy before suddenly the whole plug was in me except for the flared base. At that moment, when I took the whole plug inside of my ass, I experienced the most intense orgasm in my life. I shot rope after rope of cum all over the tub leaving a sticky mess and when I tried to get up, I had to steady myself because my knees and legs were weak from it. Now I masturbated like any regular teenager, but I have never cum so hard, and never ever have I been able to cum without touching my cock. This was the most intense orgasm of my life at that time.

After my legs regained their strength, I slowly walked across the bath room to get a towel to clean up the mess. After cleaning up the mess, I started a warm shower. Standing underneath the shower head, I reached down in-between my legs to find the base of the plug. Slowly I started to pull it out, enjoying the sensations of it sliding out of my hole slowly. After I came back to my sense, I slowly soaped my body, and washed myself and my toy clean. Still riding the high of the orgasm while I was drying myself, I thought, "If the plug was this good, I can't wait to try my dildo."

At this point I wrapped the towel around my waist and headed back to my room hoping nobody was up and catch me carrying a butt plug in the house. Inside my room, I found a pair of thong panties and put them on, making sure to tuck my cock away properly to complete the perfect silhouette. I was now finally beginning to feel tired, and climbed into bed. I fell asleep thinking that I had to get onto that swingers site I found so that I could further explore my desire to cross-dress and my bi-curiosity. After all if a toy was that good, the real thing must be better right?

To be continued........