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 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 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 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.”

I excitedly told her I would like that. I couldn't believe it. My dream was coming true.

“We‘ll go to the mall and play it by ear. Okay, let’s go,” she said. “By the way, you can leave the panties, bra, garter belt, and stockings on under your boy clothes if you want.” She winked at me and smiled.

I went to my room and put on a pair of jeans and a loose-fitting sweatshirt. I was excited.

Off we went to the mall. I acted shy and even embarrassed while she picked out a few bras, letting me nod if I liked the look. She picked out one in pink, white, and black. These would match the ones I already had. She got a garter belt and a couple of pairs of stockings. Then we were off to the dress and skirt section.

She held up a dress in a light blue that she thought would fit. I nodded my approval.

She also picked another in light red and chose two pleated skirts. She paired a grey turtleneck sweater and a white blouse with a bow around the neck.

We went to the shoe department. Mom went to an older saleslady and talked to her quietly. The lady motioned for me to come to a rear dressing room.

“This nice lady has agreed to get some shoes for you to try on.”

The lady smiled and told me to sit down and take off my socks.

“Oh, wonderful,” she said, “you’ve got women’s hose on.”

After measuring my foot, she brought quite a few pairs in different styles. We decided to get a pair of black pumps with a two-and-a-half inch heel, a pair of ballet flats, and a pair of sandals with short heels.

“We’ll try these first,” mom told the sales lady. “Once she gets used to walking in these, perhaps we could come back for something with a higher heel?”

I smiled that she had referred to me as “she.”

“Of course”, the nice lady replied. “Hopefully you will be able to return looking like a girl if you’d like.”

I smiled at that thought. So did mom.

I thanked her for doing this. She said you're welcome and said to me, "You’d be surprised how often this happens. It’s just fine."

Lastly, we went to a wig store. The sales lady again was very accommodating. She took us to a private fitting room. I tried on about ten wigs. We all decided on two: a light brown wavy, shoulder-length one; and a longer one with bangs. The color of both closely matched my natural hair. Mom and the lady agreed that even dressed as a boy, I looked like a cute girl in both. This excited me. She even told us she hoped we would come back.

We were both happy and excited as we carried the packages into the house from the garage. We went to my room and took everything out. Mom started taking off tags. She told me to take off my clothes. I took off my jeans, sweatshirt, and socks. I still had on her panties, bra, garter belt, and stockings. She looked at me and said “that too. You’ve got your things now.”

I took off all but the panties. She looked up and noticed a bulge in the panties. “Oh my honey,” she giggled, “that’s not very feminine. “

“Well, you’ll have to be careful about that if you do go out as a girl. Try to push it back between your legs. I will try to think of what you can do to make it look more feminine down there."

Mom then said, “Of course, you know that girls don’t have penises. A female has a vagina and a clitoris, as I’m sure you know. The clitoris, or clit, as some call it, is a sexual organ, somewhat like a penis. It’s even capable of an erection. But clearly, it’s much smaller.”

“I didn’t know that, Mom.”

Mom went on, “So my point is, if you’re going to be a girl, we need to make it look like you have a vagina. And why don’t we refer to your thing as your clitoris?”

I agreed that it made sense. “I like the idea of thinking of it as a clitoris, Mom. Thanks.”

Mom told me she would look into things that might help me hide my “clit” better, and give me a more feminine appearance. I thought to myself, “Wow, Mom’s getting into this.”

Mom handed me the 36C bra that matched the panties I had on. I excitedly slipped on my new bra. Mom went to a drawer in her room and brought back some old pantyhose and stockings.

"We'll place these in the cups to fill you out for now." She stuffed them into the bra cups.

“There, now you’ve got a nice set of girl’s breasts.”

I don’t know why I hadn’t thought of stuffing my bra, but I certainly loved the look. I slipped on the new garter belt and stockings.

Mom went on, "Let’s put you in that pretty dress. I have to say, I am enjoying feminizing you."

"I'm enjoying it too, Mom."

I slipped on the blue dress. I was feeling more and more feminine. Mom said before we put on the wig, “how about I do your makeup?”

That sounds fun I said, and she directed me to sit on a stool by her dressing table. It had a mirror but she told me to face her. She proceeded to carefully explain every step so “You can learn to do it yourself”. She applied foundation, eyeliner, eye-shadow, mascara, and finally lipstick.

“Wow, you look like a young lady—and those lashes! I have always thought you had feminine eyelashes. Turn around and look in the mirror.”

I turned around and stared into the mirror. I couldn’t believe I was looking at myself. What I saw was a very pretty young lady. I was amazed.

Mom said I looked fabulous. “No one would know you are a boy.”

I stood up and modeled in front of the mirror. I loved my feminine look. I particularly liked the curve of my breasts in the dress.

“How do you feel?” she asked. “I feel very natural and very feminine”.

"That’s wonderful," she said. “You make a beautiful girl."

"Thank you, Mom. I love hearing that.”

"But how can I call you Rob when you look like this? Let's use your birth name - Robin. I know you didn't like it when you were younger because some boys said it was a girl's name, but it seems appropriate now."

I agreed. I hadn't liked it. But now it did seem perfect.

I slipped on the pumps. I was wobbly at first. But soon I could walk. Mom said I had to change the way I walk. She went to her room and came back wearing a pair of pumps that had a similar heel height. She walked across the room. “See, one foot in front of the other, and sway your hips more. Also, keep your shoulders back and keep your arms to your sides, and don't swing them out too far. She instructed, “Just try to be demure."

I did as was told and soon she complimented me on my feminine walk. “Once you get used to those, maybe we will try a higher heel.”

We went to the living room. I continued practicing my walking and movement. Mom showed me how to sit properly and how to cross my legs when I sat. “You’re a fast learner Robin,” Mom complimented me.

We were sitting in the living room when Mom said, “Here we are - a couple of girls all dressed up and nowhere to go” You know what, I think you are completely passable as a young lady. So let’s go out to dinner and celebrate.”

I was surprised. Here I was, fully dressed for the first time, and Mom thought I could go out in public. “I don’t know, Mom. I’m still new at this. I think I need to build up my confidence.”

“Well it’s still early so let’s go back to the mall. We can walk around, shop a little more, and see if anyone notices”. I agreed. It was exciting.

We returned to the mall. Mom kept a close eye on me, occasionally correcting small things about my movement and walking. She suggested that I needed a purse so we went into a department store and looked at some. We picked out a small one, big enough for some makeup and other things. Then we went and picked out some makeup that would be just mine. We sat on a bench and I put my new makeup in the purse.

From what I could observe, both women and men seemed to think I was just a girl shopping with her mother. Nothing unusual. A couple of guys even smiled at me. I shyly smiled back.

I told Mom I had to go to the bathroom. “What should I do, Mom? I don’t think I can hold it till we get home.”

“No problem,” she said. “There’s a public Ladies' Room here.” She told me we would go there, but just remember “You sit when you pee.” She giggled.

I peed, sitting on the toilet. I wiped a drop off my clit and pushed it in between my legs. When I came out of the stall, Mom was looking in the mirror alongside another woman, both of them freshening their lipstick.

Mom turned and said, “Robin, why don’t you freshen your lipstick.” She smiled at me. I went to the mirror and took out my new lipstick. I applied it as Mom had taught me.

The other woman looked over and smiled. She said to my mother, “Is she your daughter?” Mom said yes. “Well, it’s nice to see a young lady that knows how to dress and apply makeup appropriately.” I nodded and smiled at her.

When she left, Mom said, “Well Robin, are you convinced you pass as a girl?”

"I guess I do mom." “Let’s go to dinner,” I said.

On the way to the restaurant, Mom suggested we work on my voice. "You do have a rather high voice so you shouldn't feel afraid to talk." I knew I did. Every time I answered the phone, I was addressed as “ma’am.” "Just be a little restrained and keep it soft." I practiced a little on the way.

When we got to the restaurant, an older gentleman greeted us with "Good evening Ladies. Two for dinner?" Mom smiled and nodded. After we sat, a young waiter came over and asked how we ladies were doing. He kept smiling at me.

We ordered and after he left, Mom said "I think he likes you. How does that make you feel?"

I told her it was strange but that I liked the fact that he thought I was a young lady.

After dinner, we went for a walk in the park. I loved the sound of my heels clicking on the sidewalk. It was a beautiful evening. I thanked Mom for helping me be who I thought I was. When we got home we were both tired from our big day.

"Let me help you take off your makeup honey. That’s also something you need to learn.” We went into the bathroom and I took off my dress. She instructed me on how to use makeup remover. I hated to take it off and I told her.

"You can put it back on in the morning. You need the practice." With that, she turned to go to her room.

"Oh wait, Robin. Would you like to borrow one of my negligees? We should have bought you one."

I said that would be nice and she went and got a cute pink one and handed it to me. "Sleep well, my little girl."

"Good night, Mom."