Chapter 3 – Robin’s First Date

I had just turned seventeen years old. I was in the second semester of my junior year in high school. I was somewhat of a loner, although I did get together in a study group regularly with four girls from my advanced classes. That was pretty much the focus of my social life.I was an only child and very close to my mother. My father had a job that took him out of town for weeks at a time. So most of the time, it was just us.I was aware that guys at school, particularly the jocks, thought I was gay. I didn’t believe I was because I had no interest in guys. On the other hand, I was seventeen and hadn’t dated a girl. I guess I didn’t know what I was. I do know now that it was at this time I became obsessed with her lingerie. I’m not sure how this fascination started. My guess is it had something to do with seeing her in lingerie.The first time I saw her in underwear, the door to her bedroom was open. I had gone in to ask her something. My head was down, and when I looked up, she was standing there getting dressed. She was wearing only a black bra and panties. I apologized and immediately turned around to leave.She told me not to leave and asked what I wanted.“Seeing me in my underwear is no big deal,” she said. “It’s no different than a two-piece bathing suit. I’m not embarrassed and you shouldn’t be. I don’t want you to feel that you can’t come and talk to me if you need to.”I admit I occasionally did time my visits to coincide with her getting dressed. I was careful not to do it too often, but I did do it. If she noticed, she didn’t seem to mind.On one “accidental” visit, she was wearing a pink bra and panties. I just loved that look. I asked her why women got to wear such pretty, colorful underwear, while male underwear was so boring. She giggled at that. She was always giggling.Surprisingly, she said, “You’re right. I really can’t think of a good reason. And if you want, I don’t see any reason why you shouldn’t wear pretty panties.”She walked to her lingerie drawer and took out a pair of pink lace panties. She handed them to me.“Now you have some pretty underwear.”I didn’t know what to say. I just took the panties. I brought them to my room and put them in my underwear drawer.A few days later I decided to try on my new underwear. Fortunately, I had a slight build. I was only five feet, seven inches tall, and weighed only 130 pounds. Her panties easily fit me.Slipping them on Şerifali Escort was surprisingly exciting. I loved the feeling. I figured if mom thought it was okay, I might as well wear them regularly. With only one pair, they needed washing. Because mom knew, I threw them in the wash hamper. She later commented that I must like them because they are in the wash every week.”You know what? Because you like those panties, I’ll get you some of your own.”She smiled at me. I just smiled back. I certainly didn’t talk her out of it.Two days later, after a shower, I opened my underwear drawer and found five pairs of lace panties in various colors. From then on, I wore panties almost all the time.Perhaps because of seeing her in lingerie, and her acceptance of me wearing panties, I became curious about wearing lingerie. Panties made me feel different. It was as if I was escaping into a different, more feminine persona. I liked that feeling.One day when mom wasn’t home, wearing just white lace panties, I went to her bedroom. I opened the drawer from which she had taken the panties she had given me. It contained panties and quite a few bras.I removed a white lace and admired it. I tried it on. Wearing her bra increased the feeling of femininity I got from wearing only panties.The urge to wear a bra when she wasn’t home became intense. I simply couldn’t resist it. In a short time, I was wearing a bra and panties every time I was home alone. I decided if wearing a brassiere increased this enjoyable feminine sense, why not try on other things? I put on a garter belt with stockings. My feeling of femininity increased. The feeling was exhilarating and I wanted more.I started wearing her dresses, skirts, and tops. I realized I loved the feeling of “being” a girl. Mom knew I was wearing the panties because I regularly put them in the wash. She was a nurse and was gone all day and often on the weekends. Since my father was always away for work, I was dressing quite frequently. I simply enjoyed looking, and more importantly, feeling feminine.I reached a point where I couldn’t satisfy my desire. I long as to wear a wig and girl’s shoes. Mom’s heels were nice but too small. I tried lipstick but didn’t know what to do with makeup beyond that. The urge to dress feminine was becoming insatiable.At this time, a critical event happened that would alter my life. It was a Şerifali Escort Bayan Saturday morning. After breakfast mom told me she was going shopping with a girlfriend and wouldn’t be home till the evening. “Let’s go out to dinner tonight,” she said as she went out the door.Oh boy, I thought. I can be dressed all day. Soon after she left, I made a bee-line to her bedroom. Within no time, I was in a bra, panties, garter belt, and stockings. I put on a full slip. Over that, I slipped on a dress that fit fairly well. I planned to be like this all day.I was sitting in the living room concentrating on some homework when suddenly the front door opened. Mom walked in. I jumped up. I froze. There was nowhere to go.“Oh my,” she uttered.“Geez mom, I’m so sorry. I don’t know what to say.” I nervously stammered, “I’ll go take these off.”Mom immediately said, “Wait honey, let’s talk.” She told me to sit and calm down.I sat on the couch and she came over and sat next to me. She told me that her friend wasn’t feeling well and they decided to cancel their shopping. She then told me that the fact that I was dressed like this didn’t surprise her. She explained that she suspected that I had been wearing her things.Mom went on, “First, I saw how you liked wearing panties. I don’t think you’ve worn boxers since I bought them for you. I also noticed that my things weren’t where I had put them away. My bras also seemed a little stretched.”“Oh mom, I’m sorry. I won’t do it again,” I blurted.She looked at me kindly and said she didn’t think that would be necessary.“Be honest honey. Do you want to stop? It’s apparent you like dressing in feminine things.”She explained that she didn’t see anything wrong with it.“It’s harmless, and if it makes you happy, I have no problem with it.”Mom asked, “Why do you like doing this? Do you want to be an actual girl or do you just like dressing in feminine things?”I stammered and hesitated, but finally said that I just liked the way it made me feel.“I guess I like feeling feminine. It lets me be someone else who I feel is buried inside me.” I went on, “I’m not sure I want to be a girl, but I do like looking like one. I wish I looked even more like a girl than I do now. It’s just a feeling. I feel it’s just me.”I went on, “I know it’s wrong, but I like being feminine.”She told me there was absolutely nothing wrong with it. “It Escort Şerifali doesn’t hurt anyone. And if that is what makes you happy, you should continue. But…” She hesitated.“But what mom?”“But, I think if you want to dress and look like a girl, you might as well have your things.” She smiled and said, “You can’t just keep wearing my things. Would you like that?”Again I hesitated but admitted I would. I could barely contain my excitement.“It’s funny,” she said. “I had planned to go shopping today for lingerie and clothes. So why don’t we do that for you?”She could tell I was excited by this proposal.“Let’s discuss this before we go. First I need to measure your chest because my bras are a little too small for you. I’ll explain sizing in a minute.”Mom told me to take off the dress. I stood up and took it off.“Oh, I see you are wearing one of my slips. Take that off too.”I did as told.Mom smiled as she saw her bra, panties, garter belt, and stockings. “Well honey, you sure do like girly things.” She just smiled at me.She obtained a cloth tape measure from a kitchen drawer and measured my chest under the bra cups. Mom told me that I would need a size 36 bra. She explained how brassieres came in different cup sizes, depending on the size of the breasts.“For instance, I wear a size 34C. So you get to decide what size you want. Would you like to have breasts like me?” She giggled.I said maybe. “They are a nice size,” I said.“Okay, so we should get you a size 36C. We’ll see how that looks.” She went on, “I think with that size, you would look quite natural.”Mom then asked, “How far do you want to go with this? I mean do you want to try to pass as a girl? Maybe leave the house looking like a girl? Go places where everyone thinks you’re a girl?”The thought excited me. I said that I had thought about that, but didn’t know if I could pass as a girl. “And I suppose even if I looked like a girl, I’d have to learn to act like one too. Honestly, mom, I think it would be so exciting to go out in public and have people think I was a girl.”“Okay then,” she said, “Let’s work on that. I can certainly teach you how to act like a girl if that’s what you want. And there are things we can do to improve your feminine appearance.”Mom continued, “Your height and build certainly help. Don’t take this wrong, but your height and slight build are more like a girl’s.”I didn’t take it wrong at all. I was thrilled to hear it.“First off, you should get a female wig. And you will need a girl’s shoes. Want some high heels? She said excitedly.Mom almost seemed as excited as I was about my transformation. “I need to give this more thought,” she said. “Oh, and of course, you have to learn to do makeup.”