Alex Becomes Aly

My name is Alex. I am 21 years old and I have an older sister that I resemble so closely that most people who don't know us think we are twins. Cindy is 2 years older than me and because we lived in a rural area growing up, we were each others best friend until our early teens. By anyone's standards, she is very pretty. She has shoulder high blonde/brown hair, dark brown eyes and a natural blemish free complexion.

We shared the same dark brown eyes and were about the same size. This meant that her clothes fit me and vice versa. One of our favorite game was dress up. I ended up in dresses, skirts and heels while she wore my jeans and boots. She also liked to use me as live mannequin l. I would put on her clothes and model them for her. This grew into more accessories and as time went on, included hair-dos, painted nails, jewelry, etc. She constantly commented on how pretty I looked and said I should have been a girl. At the time, it went in one ear and out the other.

Our mom worked until 6 most days, so when Cindy was away I had the house to myself quite a bit. I used this time to continue our dress up game. I would go into my sisters room and pick through her clothes and change into what fancied me that day. I was mostly fond of wearing skirts with bright tops. I liked the way it felt, having my bare shaven legs exposed with nothing between the outside air and my privates except a thin layer of cotton or silk. I would parade around house in my girly attire, unless it was nice out, and then I would sit on our patio and read a book or something.

One day Cindy came home from school early and caught me in one of her skirts. After a lot of quizzing, I opened up and told her that I liked dressing as a girl better than a boy. Since we were so close, she said that she would help me "figure this out". She told me to dress up in my favorite outfit the next day and that she would find something for us to do.

I was nervous all day at school and rushed home to change. I picked out a denim mini skirt with a bright yellow top and wore black heels. I put on a few finger rings, an ankle bracelet and several loose fitting bracelets on my arms. When my sister came home all she said was, "Wow, you look great". She told me to jump in her car and away we went. She took me to a mall kind of far from our house so we didn't run into anyone we knew. I was scared to death walking around in girls clothes where other people could see me, but at the same time it was amazing. It was a good thing I tucked myself tightly into a pair of panties because I was hard the whole time.

I quickly noticed that all the boys and men stared at my sister and me as we walk by them. I never noticed this before. Cindy picked up on this and asked how I liked being stared at by all the guys. I wasn't sure how to answer, I hadnt given it much thought actually. "I guess I like it", is about what I told her. Then she asked the tough question - "do you like boys?" There was no easy way to tell her the truth and I wasn't sure either. So, I told her I liked girls and boys, and as far as I knew at the time - that was the truth.

All through high school, until Cindy went away to college we would go out to the mall or movies with me dressed as a girl. I shopped for my own clothes, jewelry and makeup. Cindy taught me how to use make up, paint my nails and do my hair so I looked as much like a girl as possible. Even at 18, keeping my legs and body shaved, I looked completely feminine. I had girl friends on and off through school, but I never entertained getting together with boys. The town was too small and the trips with my sister satisfied my girly urges. This all changed when I went away to college.

I attended a small private school about 200 miles from my home. I was able to get a small apartment near school where I could walk to class most days if it wasn't raining or too cold. On the nastier days I took the bus. There was a very nice mall a short bus ride away, so between that and internet shopping I was able to keep myself in clothes, though at this point I bought uni-sex clothing when possible. All of my jeans, tops and shoes were from the Junior girls section and as time went on, I spent more and more time in girls clothes. The anonymity of college made it easy to blend in any way you wished. I maintained a feminine appearance all of the time by keeping my hair in a girlish style and my nails clear polished. I used a light skin tone lipstick that accented my lips, but didn't call attention to them. I got looks from both boys and girls and probably could have had my pick of either.

One day in my English class a guy came up to me and asked my name. He was a little like me, not especially masculine, but he clearly carried a guy's persona. He was about 6' tall and thin, and he had a very soothing smile; I found it hard to look away from his face. There was an instant attraction that I had never felt before. I stumbled telling him my name, and before I knew it, "Aly" came out of my mouth. I had never used the name Aly before, except maybe with myself. I just wanted him to think of me as a girl. We chatted for a few minutes and after class was over, he asked me to have lunch with him.

We sat together in the cafeteria for over an hour, chatting away about all kinds of things. I was playing the girls part and it felt perfectly natural. We both had to get going, but before parting he asked me out on a date. I immediately said yes and told him where I lived. We arranged to meet later that evening to go to diner.

When I got home after classes I started getting ready. I had never had a date with a guy before and had no idea how to prepare. I decided to wear a flattering pair of jeans, a pretty pink top and a black pair of low heels. I put on red lipstick and accented myself with light jewelry. I was not gender neutral. He arrived right on time and we left for dinner.

I found it easy to speak with him and we talked for several hours before going home. We decided to walk back to my place, which was about a 20 minute hike. I could feel his hand dangling near mine and I knew what he was about to do. He took my hand in his and we walked the whole way back holding hands. It was hard to keep my mind on our conversation and when we arrived at the door I didn't know what to do. He was quite a bit taller than me so when I started bending down, I knew I was about to be kissed by a boy. Our mouths met gently and I reached out and put my arms around his neck. When he started to pull back up, I softly pulled him back in and slid my tongue into his mouth. We kissed for several minutes and afterwards I composed myself and invited him in.

I had never felt this way before and I knew I didn't want the evening to end just yet. I walked him into my apartment, sat him on the couch and got us both a glass of wine. After a sip or two we started kissing again. His hands started wandering and I knew I wasn't ready for him to find out what I really was. I gently took his hands in mine and slipped my way onto the floor and between his legs. I looked up into his eyes as my fingers undid his belt and zipper. I tugged on his pants as he helped me wiggle them to the floor. He was neatly trimmed with a little hair just above his cock. It was the first one I had ever seen this close except for my own. It was long and thin with a beautiful full head. I stared at it for a few seconds before I lowered my lips to take it in my mouth. This was another first as I kissed and licked my way around his growing dick. It was probably a little new to both of us because I had him ready to cum in just a few minutes. I could taste and feel his pre-cum and just kept on sucking. Within a few seconds he was pumping cum down my throat. I didn't hesitate to swallow all of it down and kept sucking several minutes after he was done.

I looked up to find a smiling face. I gently kissed the head of his now soft cock, rose up and kissed him on the lips. All I said was, "that was fun, but it is time for me to get to bed." I helped him with his pants, kissed him at the door. I told he we'd do it again soon. I went to bed and smiled as I reminisced about my first blow job.