Dear Mistress Alexa;
I have not read all the stories, but thus far this is my favorite by far.
I was introduced to cross dressing by my older teenage sister and a friend of hers when I was 7. I remember it like it was yesterday. It was a rainy Saturday and I couldn’t go out and play. I walked by my sisters room and her and her friend were trying on make up and curling their lashes. I had never seen an eye lash curler, and it looked painful. I walked into her room and asked what that was as it looked painful. They both laughed, and said no it wasn’t painful it was an eye lash curler and did I want to try it for myself. I giggled a little and said no its okay. My sister then said my kid brother Sxxxx, he has lashes to die for, he should have been born a girl. And as soon as she said that they both looked at each other, and I guess the idea hit them both at the same time.
My sister said in a very sweet voice, “you want to play dress up with us Stevie, it will be fun and besides its raining outside so you cant play outside.”
They were both smiling at me sweetly and I was enjoying their attention, so I srugged my shoulders and said, as long as you promise not to tell anyone I guess i will play with you. They both smiled and my sister say okay honey, please strip off your boy things for me, because if we’re going to play girly you have to be all girly.
I started to protest and my sister says, on Sxxxx, don’t be such a baby, you are going to love the feel of girly things and you will look so pretty when we finish I promise. So i stripped off everything except my tiddy whities, and she gave me a stern look and said everything, its not like we havent seen a naked boy before.
So I relented and she handed me a pair of soft silky panties and told me to put them on while she gathered some things that would fit me. I remember the sensation of these soft silky panties against my skin was wonderful. She next asked me to hold my hands up and she pulled a full slip over my head and then adjusted the straps to fit. Then she took her full palms and ran them down both the front and back of me to smooth out the slip she told me as she was brushing against and over my little dicky and bum and I started to almost hyperventilate as this new and unexpected wave of excitement began to wash over me.
I had never been sexually arroused before and I was too nieve to understand what or why this excited me so much. My sister next handed me a pair if tights, but then took them back and said, sit on the bed honey I will help you with these so they don’t rip or tear. So I sat on the edge of the bed and watched as she roiled them up my legs past the knees and then said, take my hand to stedy yourself now and slowly stand up and I will pull them up for you. At this point I was practically hypnotized and too excited to disagree. She reached down and slowly pulled them up lifting my slip up telling me to hold it up high as she pulled the tights up and even above my waist. Then she pulled my slip down and repeated the palms running up and down me smoothing out the slip again and with the added slick encasement of my legs ass_and crotch and her rubbing against my little dicky, it was more excitement them I could bare and suddenly without warming I wet myself.
Not really a lot but I was so light headed and panting at this point yet the wet spot appears immediately and I looked down in embarrassment and shame, my sister looked me in the eye first sternly and then when she saw me begin to cry and say I’m sorry Sherry, I didn’t mean to, I’m so sorry. She then hugged me gently and softly said, it’s okay honey, you only wet a little and all us girls sometimes wet ourselfs when we get too excited.
I didn’t realize you were so excited to me girly and that’s okay your dress will cover the spot up and we can clean you up good when we finish. And she kissed me softly and whipped away my tears, saying isn’t that right to her friend and they both hugged me and I looked up and said I really am sorry Sherry, I will clean your things for you, but I couldn’t help it, I didn’t mean to. Then her friend said yeah Stevie don’t worry I wet myself every time I get excited too.
And so we all giggled a little and said, I guess someone really loves being girly and in a moment of immediate realization, I nodded my head in agreement and wispered yeah its way more exciting them i ever thought possible and we all laughed. By then my sister had found a dark colored dress and said raise your arms again honey and I did as she pulled the dress over my head and this time slowly and avoiding directly sliding her plan a over my dicky area she smoothed out my dress and slip.
Next came make up and some jewelry and low 2 inch heels and she again said take my hand again honey until you feel steady in those shoes. And the each took a hand and we pranked around her room together and theysmiled down at me and said take a look Sxxxx, your as pretty and any girl can be and I loved it and was hooked for life.