John Meets Amy, Finally Pt. 01

First, a little bit about me. Amy is my pseudo-femme, you see I have been living a double life for quite some time now. I'm a male to female pre-op transsexual, meaning I haven't had sexual reassignment surgery yet and really, I don't know if I ever will. You see I want to be a girl but a real born as a girl, girl, not a surgically created girl but that's just me. I do however enjoy dressing as a girl and having fun. I'm very passable, measuring a petite 5'5" and 120 pounds with long blonde hair and deep blue eyes, a flat toned stomach and a hot curvy ass. My girlfriends always tell me they wish they had my ass. Slender toned legs and long slender fingers. I keep my body smooth and hair free, not that I have much to start with. High cheekbones and full luscious lips. I live as a guy for my work and my family but almost everything else I live as Amy.

So, as you might guess none of my family has ever met Amy. I don't think they would approve and I guess that's alright, but it makes me being happy a little more difficult. I know my work would never understand, they have a very strict morality clause in our contracts, and while it may sound prejudicial it has been tested in the courts and upheld every time. Because of this, I live in the next town over away from my work and even farther from my family so that when I'm off I can be Amy as much I need or want to be. As time goes by, she is becoming more and more common. I transform as soon as I get home and remain her until it's time to go back to work every day and all weekend. I go out with Amy's friends, none of whom know her secret, and have lots of fun and lots of sex, mostly with straight unknowing men that I meet out. Usually not the same guy more than a couple times as he would probably get suspicious of my reasons for not having vaginal sex. I do my best to keep them satisfied with oral and anal sex and great reasons why I can't do the rest, LOL.

When I go to visit my parents or any of my siblings, I go as my drab self but always carry a change for Amy for the trip back home. I am one of five children, 2 boys and 3 girls. The oldest is my brother John, followed by 3 sisters, 1 single, Cheryl, and a pair of twins, Kim and Donna, then me, the youngest, Brad. We're only 3 years apart, youngest to oldest so we were all very close growing up. My brother is the typical macho guy, tall, rugged, great with girls, good looking, and funny to boot. He's 6'5" with broad shoulders and dark hair and baby blue eyes, great smile, big hands and feet, and what they say is true for his other things too if you know what I mean. My sisters are all beautiful, blonde hair and blue eyes, the oldest is 5'8" with a killer body and the twins while more petite at 5'2" and smaller proportioned, still great bodies. Then I come along and favor more the female side of the family with a smaller frame, blonde hair and blue eyes, just no boobs or vagina. I got picked on by guys in my class at first but my oldest sister and my brother warned them off so that little issue went away.

When I was younger, I always hoped I would get to be a big guy like my brother but one day I began to realize I didn't want to be a big guy like my brother anymore I wanted to be a girl like my sisters. And even more confusing I developed a major crush on John, like all the girls in town. Later he went off to college on a football scholarship and I was left to fantasize alone with my sisters. I dated some girls in high school but it was more to throw everyone off of what I really wanted. I watched as my sisters each grew up and went to proms and homecomings in beautiful dresses with their hair and makeup done just so and I was so incredibly jealous.

When I went off to college, we all ended up at different schools for some reason, I started to explore my femme side with a little crossdressing but usually something kind of obscure like wearing girl's jeans or something and wearing eyeliner which was all the rage back then. One day I was out shopping and decided I wanted to dress completely, so I bought a pair or panties, a bra, some pantyhose, a skirt and blouse, a pair of low heels and some makeup. When I got to my apartment, I immediately took off all my clothes and was frantic to get all my new things on. My bra and panties were a matching purple and black set, my pantyhose taupe, my blouse was a cap sleeve single button in back in yellow, and my skirt was a red mini that came to about mid-thigh, and my shoes were red pumps with a 3-inch heel. Once dressed, I was looking in the mirror and decided I didn't look too bad but I still had hair on my legs and no makeup. So, I got undressed and went to the shower and shaved everything from my upper lips to my toes. It felt so strange but so delicious at the same time. I got dressed again but this time all the smooth materials felt so electric on my skin. I stood in front of the mirror and did my makeup and then checked myself out and thought I looked pretty good and very convincing as a girl. I decided to see if anyone else bought it too and grabbed my keys and headed out to a local club.

The guy at the door let me in for free, which had never happened before, and I walked around the club for a few when this guy stops me and starts talking to me. After talking for a few he asks me to dance and off to the dance floor we go, 2 fast songs and then a slow song. I didn't know what to do really so I just held onto him as we swayed, he started with his hands on my back but as the song progressed his hands slid down to my hips then to my butt. I really liked the attention and pulled myself tighter into his body. I looked up into his face and he was looking down at me and he moved his head down till our lips met and he kissed me and I kissed him back. I was so hot for him right then and I moaned into our kiss as we swayed and made out. His hands were in my hair pulling me into this kiss and my hands were up his back over his shoulders pulling myself into him. He stopped and smiled down at me and whispered in my ear. That was really hot and you've got me really turned on, do you think you could give me some head to take care of it.

I was shocked at how forward he was but so turned on, so I just shook my head yes and he led me back to the restrooms and found a corner and backed me up against the wall. He began kissing me again and unzipped his fly while we kissed. He pulled out a very hard, average size, leaking penis and pulled my hand down to it and told me to stroke it. I did for a few minutes as we continued to make out. Then he pushed me down to my knees in front of him and rubbed his penis across my lips and smiled as he said go ahead as he pushed it into my mouth. I was shocked at first and didn't know what to do. I had my fingers wrapped around the base kind of controlling the movement but he was still thrusting in and out my mouth. I had seen porn before so I tried to remember what the girls would do as they sucked off the guys. I started sucking some and moving my mouth up and down on him and in a few short minutes he exploded in my mouth. I gagged on his cum at first and coughed some of it out all over his penis but managed to swallow some too and he seemed to enjoy the whole thing but once done he zipped up and disappeared without another word.

I just knelt there with my hair and makeup all messed up and cum dripping down my chin, thinking wow that was so fucking hot.

I got myself up off the floor and went into the ladies' room to try to clean myself up as much as possible. I went back out to the bar and bought a drink to wash my mouth out and as I sipped my drink another guy came over and started hitting on me. We talked for a bit then went to dance to a few songs and then I told him I was tired and needed to head home. He thanked me for the dance and leaned in and I moved my lips to his and kissed him. I thought it was softer and more passionate than the first guy and I put my arms around his neck and became more aggressive in the kiss. I smiled as we broke the kiss and told him I enjoyed the dance and the kiss very much and that I hoped I would see him here again, he said he hoped so as well.

That was pretty much how the rest of my college years went, I bought a lot more outfits and by the time I graduated I pretty much lived as a female 90 percent of the time even going to class sometimes enfemme. One of my professors figured out that we were the same person and one class when Amy showed up he asked her to stay after class as he needed to speak with her. After class, I stayed behind and once everyone was gone he told me he knew I was really Brad. He told me that it excited him to see me dressed and that I looked incredible. He went on to tell me, he would allow me to continue coming as Amy if I would have sex with him. I smiled because I found him attractive and would have been happy to have sex with him. But before I said yes, I had something else in mind so I told him I would have sex with him if he would give me an A. So, I did and he did, on multiple occasions.