576 Shadow Oak Drive – Part 1


I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn’t have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the department store not only because of the discounts, but because I had figured out a way to sneak some of the clothes, that I didn’t have the courage to buy, out the back door without anyone being the wiser. These items consisted mainly of feminine lingerie. Being that I grew up in a strict household, I hadn’t been able to experience much of the life of a typical teenager. I didn’t play sports and wasn’t a member of any particular social group. I had a couple of close friends that I had known since grade school, but that was it. There were few friends, no girlfriends, and no typical high school parties. She was about to change all that. My head was down as I concentrated on scanning the bar code tags on the various items of clothing coming down my line, removing the hangers, and putting them in bags before telling the customers their totals. In the conservative town in which I lived, any woman buying underwear wouldn’t possibly go through the checkout manned by a young boy, and that is why I was shocked frozen when I saw the cutest little pair of lacy black bikini-cut panties come rolling down my line. My eyes went further down the belt and I saw even more of these items, bras, panties, teddies, a garter belt, and some other, more ‘normal’ attire like white short-shorts and tank tops. My hands started shaking as reached for the first pair and fumbled to find the tag. My face flushed and I could feel myself start to Escort ankara sweat. That is when I looked up and saw the most beautiful face I had ever seen. “Easy there. They’re only panties,” she said with a smile. I let a little nervous, embarrassed laugh out as I reached for the next pair. My lack of exercise and sports in school had left me without any muscle definition. I wasn’t fat, or skinny, but I did still have what my mother affectionately referred to as “baby fat” covering my body and face. Needless to say, this didn’t give me much confidence when talking to girls, and I certainly couldn’t compete with the boys at school for dates, so I didn’t have much experience in making small talk with them, let alone anyone as beautiful as this girl. “Sorry,” I stammered, “I don’t ring up many panties.” “My name’s Molly,” she said. “What’s yours? Oh wait. Hi, Sam,” she laughed as she looked at my name tag. “That’s me,” I replied. “Well, it’s nice to meet you, Sam.” I continued fumbling around with each tag until the order was done. Molly was making small talk the whole time telling me that she was getting some new clothes for the summer. When the order was finished, I gave her the total and she swiped a card. The receipt printed out, and she took out a marker to sign it. When I reached down to grab it and make some pithy ‘have a nice day’ or something, she grabbed my hand started to write on it. She wrote her email. I stood there starring at her as she held my hand. She was tall, as tall as me, 5’10”. Her shoulder length brunette hair had bouncy curls that framed her slender face. She had deep, brown eyes, pale skin and a small smattering of freckles on her cheeks. Her pale complexion made her bright red lipstick on her pouting lips pop. She was thin framed Balgat escort with perky B-cup breasts and round hips that gave her an hour-glass shape. “Hit me up sometime, Sam. You’re cute and I think we should hang out.” The next six months were a blur. I had found the courage to write Molly later that night and she immediately replied. We went out a few times and started dating! I had come to find that she was much more adventurous and outgoing than I was. She almost always picked where we would go and what we would do. She definitely wore the pants in the relationship, and I was absolutely fine with that. I enjoyed her vigor for life and gladly accepted letting her being the boss in the relationship. It was clear that she had much more sexual experience than me. She took my virginity after our third date. We had gone out for midnight picnic in the park and she brought a bottle of Pinot Noir. When we finished our walk home and made it into my apartment, she pushed me against the wall and started making out with me. She pulled off my jeans and sucked my cock, leaving it sopping wet before sending to the ground on my back and wrapping her tight pussy around my shaft. She bounced up and down with force, letting her full weight come crashing down on my hips while her hands balanced on my chest. We fucked for about four minutes until I couldn’t hold it in and sent a stream of hot, sticky cum up inside her. Six months of heaven. Then, one Saturday while we sleeping in my bed, she woke up and, for some reason, began snooping in my closet. Hidden the back, she found a shoe box and opened it up, discovering my secret stash of panties. I woke up to her holding the box on her lap sitting on the edge of the bed. My heart started pounding uncontrollably and my face Batıkent escort bayan flushed like the first time we met. “What are these, babe?” “Um. Well. Err,” I stammered, “You see, Molly, sometimes I like to wear those.” I scanned her face trying to gauge any sort of reaction. My mind raced to thoughts of her throwing the box in my face, breaking up with me, and storming out of my life. The seconds seemed like hours. Then, the strangest thing happened. She gave me the most knowing, sly smile. “I knew it!” she exclaimed, “That very first time we met when you rang up my panties and were shaking so bad, I knew that there was more than just you being nervous for a girl!” I felt so vulnerable with my secret exposed. Molly was laughing with excitement like she had just uncovered some earth-changing scientific discovery. Then she looked down and saw my horrified face and immediately changed her tone. She lay down next to me and stroked my hair. Looking deep in my eyes she spoke. “It’s okay, baby. I’m totally cool with this. If this is who you are, this is who I love.” My heart melted. This was the first time she told me she loved me. She leaned in and started kissing me. She was much more gentle and soft than she normally was. She caressed my body and took her time, slowly working her hand down to my stomach to my waiting cock. We made the most passionate love we ever had that morning. Over the next couple of months, Molly really began to encourage my crossdressing. She would regularly come home with new clothes for me to try on. With a little talking and a lot of encouragement, she convinced me to embrace my feminine side and give it a name. I picked Sarah. Once the name was picked, Molly took to calling me Sarah whenever I was dressed, which was becoming more and more. I never dressed in public, and Molly understood that, but she increasingly wanted me to become Sarah when we were at home. She taught me how to put on make-up and encouraged me start growing my already shaggy hair out so that she could play hairdresser on me and style in various girly styles when I was dressed.

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