A transformation from boy to Sissy
I have always wanted to wear pretty things since I can remember. I watched my older sister getting ready to go out with her friends, to school, or just hang out. I watched her pamper herself with soft sexy lingerie, stockings, garter belt and everything else a pretty girl would wear. I wanted to be a girl, just like her. I started my journey into womanhood in my teen years by borrowing a pair of my sister's panties, then it was her bra, then her stockings and garter belt. This borrowing went on for a while until I was discovered, not caught but discovered. The memory is as clear today as it was when it first happened. I was in my sister's room, standing in front of her full length mirror admiring how I looked in her bra, garter belt, stockings and panties when she walked in and discovered my secret. She just stared at me for a while and said that I should have asked her for her lingerie before I just look the liberty and wore it. She stepped back a few steps and said that I did look kinda' cute wearing her stuff but that I needed some help in the boob department, hair style and make-up. She then proceeded to do my make-up and re-style my longish hair into a more feminine style. After she was done with all this she rolled up some stockings and inserted them into "my" bra. She had me stand up and walked me to her mirror so I could see "the girl". What I saw was a girl looking back at me and I LOVED what I saw. From that day forward I started to dress in feminine underwear and loved the sensation(s). My sister helped me buy high heels and helped me to learn how to walk in them. She helped me buy my own clothes, make-up and to do my own hair. One of the most important lessons she taught me was how to satisfy a man. She showed me how to get a man to climax with my hand, how to get him to climax with my mouth and how to entice a man to stick his "love stick" into my "pussy" These lessons were learned by "hands on experience", she doing me while I was dressed, me doing her while I was dressed and the two of us doing each other while dressed. I LOVED sucking cock and did it quite often with my sisters' boyfriend and his friends also. I became her cousin Jaye from out of state and was a very popular "girl", all the boys did not know the truth and I really don't think it mattered to them just as long as they got their cocks sucked. There was one day in particular when my sister and I were having a few drinks and our inhabitions were lowered dramatically when she said that she wanted to get my "cherry" and that it was time for me to enter womanhood. I agreed very quickly and both of us went into her bedroom and she told me to get out of my skirt and take off my panties but leave my stockings and garter belt on. I was out of the articles of clothing in record time and was on my stomach with my ass high in the air. I felt something cold being rubbed into my ass and then I felt something being pushed into me. My ass accepted the invader with a bit of a struggle and then my sister pushed the entire 6 inch length of fake cock into me. At first it hurt like hell but as she started to pump me the pain stopped and pure pleasure started. She stopped long enough to tell me that she wanted to fuck me face to face, who am I to argue. She rolled me over, put my stocking covered legs on her shoulder and slipped that plastic cock deep inside me, HEAVEN, JUST PLAIN HEAVEN!!!! I exploded and my cum was all over the both of us. she had me lick up my cum from her which I did and then I licked her pussy and she came as well. I am now a full time woman with a small cock between my legs which has proved to be a real asset at times. I still wear sexy lingerie and am helping other "girls" like me develop into the woman who lives inside them.
6 år sedan