The Superiority of Girls

by

Pamela

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I live with my mom and twenty-one-year-old sister Terry. My dad took off long ago to have another family with a different wife. (Asshole!) I’ve grown up being the ‘man’ of the family, but only in a theoretical sense. Practically speaking, as the youngest in the family, now sixteen, my mom and sister lord over me. Terry is a lesbian and for quite some time she’s been dating a very lovely girl named Clara. I should say that I’m pretty used to only being around women in my house. Between my mom and Terry there’s an informality that reigns that I’ve had no choice except to become accustomed to. One can say that my mom runs our house as if it were a sorority or women’s commune. None of the rules of a normal family are followed here. For example, my mom and sister make no effort to prevent me from seeing them in their underwear and even, sometimes, stark naked. They often don’t close the door to their bedroom or to the bathroom when they’re naked or undressed and I’ll just be walking by and through no fault of my own I’ll get a suggestive glimpse of them. They might be wearing just a bra and panty, or it could be bra, stockings and girdle or garter belt. They might be wearing a slip and pantyhose or I’ll see their naked breasts and even sometimes their bush. There are times I’ve wondered if my mom and sister actually know that I’m a boy, because they sure don’t act like they know it!

From everything I’ve seen in movies or read in books, there are usually boundaries separating the males and females in a house as far as privacy goes. Girls keep their personal things to themselves as do the boys. My house has never been that way. The lack of privacy is so rampant that not a day goes by where I’m not confronted with the spectacle of women’s lingerie and clothing lying around the house in full view. Moreover, I’m often present when my mom and Terry take off their underwear. For example, very often my mom, Terry and I might be sitting on the sofa watching a movie together. While we’re watching I might notice my mother squirming and if I look over I see that she’s reached behind her back to undo the clasp of her bra. She then pulls the straps off her shoulders and then magically lifts the bra out of her blouse through the neck hole. She does this while watching the movie. When the bra is in her hand, she might just lay it on the sofa next to me or on the coffee table in front of us. My sister is guilty of doing the same thing. It’s not just bras that Mom and Terry take off in front of me. They might unhook their stockings from their garter belt or girdle and drape them on the sofa next to me. After their stockings are off, they’ll then work their hands up inside their skirts and unhook their girdles and the next thing I know they’re pulling off their girdle while I’m watching the movie. When it’s off they’ll plop it anywhere. It could be on their lap or the arms of the sofa. My sister laid her girdle on my leg once. Sometimes my mom and sister take off their panties or vigorously wriggle around getting their pantyhose off. Invariably the pantyhose ends up clinging to my arm or leg.

I assume that taking off one’s clothes is all about getting comfortable. After wearing a bra and girdle all day long, women like to unwind by taking them off. In a normal family presumably they go to their bedrooms and take them off discretely. In mine, it can be anywhere. You can see why I think of the house as a sorority. Eventually my mom and sister collect their clothing. It can be the next morning or in a few days. I saw a bra hanging from the hall coat rack for a week once. On those occasions when I’m alone watching TV there is very likely going to be a bra or panty or stocking or even a slip or dress or a pair of high heels in full view of me.

When I hit puberty a couple of years ago I began to wonder how a boy, and especially me, was supposed to navigate the female atmosphere that surrounded me. You might not believe it but the constant presence of lingerie has the pernicious effect of causing the extinction of the male psyche. Having bras and girdles and other intimate apparel, as well as skirts and dresses constantly surrounding one causes an erosion of one’s boyhood, testosterone molecule by testosterone molecule. One can fight it, and I half-heartedly did, but in the long term my boy self slowly and surely drowned in the sea of estrogen that nurtured and nourished me. To give one of many examples: Under the influence of my mom and Terry I developed a preference for romantic movies that featured brides and bridesmaids. Action-adventure movies lost their appeal. They belong to the world of men, a world which I was no longer a part of.

I used to wonder how it was that girls have the power to nullify the masculinity of boys until I figured it out one day. Girls are much superior to boys. Sure, boys have muscles but that is only one small piece of the total. Girls are smarter, wiser, kinder, and certainly have far more desirable bodies than boys. A boy's flat chest is no match for a girls' breasts which they proudly hold in their bras. Girls have larger and shapelier butts than boys. They have sleek and well-situated vaginas as against the oddly dangling penis and balls. From what I know, vaginas are capable of receiving more exotic and drawn-out pleasure than the hysterical mad dash that penises run through only to spit and collapse. Vaginas are timeless works of art out of which new life flows, while penises are swords that fall apart upon use. In addition to all of this, I've seen firsthand the self-confidence and dominant world view that my mom and Terry share. I have none of those qualities. They know so much and I know so little.

I’ve come to realize that the female dominated atmosphere of my house acts like a flow in one direction. Girls fit right into it and go with the current. Boys that want to be boys find themselves flailing away against the tide in a losing battle. The best I’ve been able to do is tread water and occasionally float in the girl universe in which I am embedded. The last male vestiges of my mind - if indeed I have any left - will soon be history. Though my masculinity has slipped away, I have not become female in its place. It’s not a zero-sum game. Right now I feel like I'm between sexes, neither boy nor girl. Since I can’t win back my boyhood against the superior forces of girls, if I want to be a sexual person, I have no choice except to try and become at least partly female.

After pondering this situation for some time, it came to me that my being a boy had isolated me from my mom and sister. My boyhood had been a definite divide between us and now that it was gone it meant that I had an opportunity to become emotionally closer to them. I hunger for that connection. I'm weary of being the odd man out in our household. I want to be part of the vital center of the family. I want Mom, Terry, and me to be equally close to each other.

It was after I had resolved to figure out how I could become closer to Mom and Terry that I realized that this was a task that was easier said than done. If I am to close the gap between me and them then I have to find a way to make up for my male inferiority. The most obvious course of action is to let the female-centric atmosphere of my house drag me along toward acquiring the characteristics of a girl. In principle, this sounds like a solid plan, but in reality I'm not sure how it's supposed to be implemented. I can see that my only hope in figuring this out is by asking my mom and Terry for help. Each time I think of saying something to them about this I get cold feet. How does one tell one’s mom and sister that they want their help in learning how to be female?

The standoff ended on a day in which I returned home from school to see that my mom had taken out her wedding dress and was showing it to Terry and Clara. Unaware of me, the three women were admiring the dress and discussing how it had been sewn. I was on the outside looking into this female world and I desperately wanted to come inside and be a part of it. I wanted to join them. I wanted to do whatever it took so that Mom and Terry would consider me to be just like them. I wished that my mom would call out to me and say “Greg, come join us girls. I’m showing them my wedding dress.” But, of course, she didn’t say anything. She and the others didn’t notice me because they believed that I was a boy and that I wouldn’t be interested. I decided that no matter how scared I was of doing it, I was going to force myself to get advice from my mom and Terry on how I could become like them. First I’d ask Terry, and then my mom if I had to.

***

I caught up with Terry in her bedroom soon after the incident with the dress and asked her if we could have a chat about something.

“I’m all ears.”

“Lately I’ve been thinking that you and Mom and also sometimes Clara do girls’ things together and I feel like I’m left out.”

“But you’re a boy, Greg. We wouldn’t expect you to want to participate in the kinds of things that girls like to do together.”

“But that’s it, Terry. Am I really a boy anymore?”

“What?”

“I think I was a boy, but living with you and Mom has pretty much taken away whatever male qualities I had. My masculinity got crushed by the feminine power of you and Mom. I don’t think I know how to be a boy anymore.”

“Omigod, Greg. Have we done that to you?”

“I’m not complaining about it. I’m okay with that. That’s not my point. The thing is that now that I’m not really a boy anymore, I’m also not a girl. But I would like to be a part of the world that you and Mom inhabit. I want to feel close to you and Mom!”

“I never thought about what has happened to you in such stark terms, Greg. Of course I’ve noticed that you’re not especially masculine, but now I see how Mom and I had some influence on that. Girls are admittedly much superior to boys so it makes sense that you’re growing up in a feminine environment has drained masculinity out of you.”

“I agree with you. The fact that you and Mom are females gives you a natural advantage over me. But I hope that maybe by emulating you and Mom I might acquire some of the great things that girls have.”

Terry smiled and said, “It’s a testimony to how smart you are that you want to imitate Mom and me.”

“Thank you, Terry. I really do love being around girls. You’re all so stimulating and interesting. I like being in the female environment. I’m particularly jealous of the fact that you and Mom are so at ease with getting comfortable that you take off your underwear and other clothes whenever and wherever you feel like doing it. I must confess that when I see the bras that you and Mom have taken off, it makes me think about how I don’t have breasts like the two of you do. I think it’s clear that having breasts is one way in which girls are superior to boys. My lacking breasts means I don’t wear a bra and that really makes me inferior to girls. It’s pretty obvious to me that by wearing bras to hold their breasts, girls are much, much better than boys!”

“Exactly, Greg. I’m glad to see that you’re understanding so well why girls surpass boys in every way.”

“But it’s hard on me knowing that you, Clara, and Mom are so much better than me, including having breasts.”

“What can I do to help you feel better?”

“I was hoping that you might have some ideas. Is there anything I can do so I feel like I’m not so far beneath you and Mom?”

“If I was having your problem I would try to be more proactive. Instead of accepting that girls are better than you, try and close the gap between you and them. This house provides many forums for learning how to model yourself after girls. With some luck and effort you can probably pick up on a few of the great things about girls and internalize them.”

“So you think that’s something I ought to do?”

“Of course, Greg. You might not have been born a girl, but you can certainly improve yourself by emulating us. I suggest that you talk to Mom about this. She can probably help you formulate some specific actions you can take.”

***

A few days later I found myself alone with Mom and I asked her if we could chat.

“What’s on your mind, dear?”

“A few days ago I was talking to Terry about how I’m envious of the way that you and Terry are women and I feel left out.”

“I’m sorry to hear that. Is it because you’re a boy?”

“Probably. Yeah, it has to be because I’m a boy. Terry agrees with me that our house has a female vibe. I’m not saying that I don’t like the way the house is. I do like it. It’s just that living here has pretty much prevented me from developing any male instincts I might have had.”

“I’m so sorry, Greg.”

“No, Mom. It’s okay with me. It’s just that I think I’m at a place where I would like to get closer to you and Terry. I’ve come to realize that girls are superior to boys so I have so much to gain if I could acquire what girls have. To do that I probably have to figure out ways that I can emulate you and Terry. Terry agrees with me about this. So what I’m wondering is what things you think I could do in order to get closer?”

“It’s so nice that you feel comfortable enough with Terry and I that you can share such private feelings with us. I should also say that I wouldn’t be surprised if your acceptance of the fact that girls are better than boys has to do with your sweet nature. Ever since you were a baby you’ve had the gentle disposition that is often associated with girls. I agree with you that you’ll be happier the more you can acquire feminine traits and practices. I am so proud of you for being open to developing this way. ”

“What do you think I should start doing?”

“I think you should go with your impulses, Greg. When you feel a feminine impulse follow it and see where it leads. In other words, feel unconstrained. Do whatever it is you feel that you need to do.”

“Anything?”

“Yes. That’s important if you want to discover truths about yourself.”

“What if I do something weird?”

“I trust you Greg. You’ve got a good head on your shoulders. Whatever you do will not be weird. I guarantee you that!”

“Okay. This is good advice, Mom.”

“If you find that you need to talk to me again about this, please feel free!”

“Thank you, Mom.”

***

A few days later Mom, Terry, Clara, and I were watching a romantic movie in the family room. Terry and Clara were snuggled against each other and I was sitting between them and Mom. Out of the corner of my eye I was aware that Terry and Clara were kissing every so often. Then a bit further into the movie, I saw that Terry had taken off her bra and had put it on the coffee table in front of her. Then I glimpsed Clara putting her hand inside Terry’s blouse and I assumed she was touching her breasts. Minutes later, like clockwork, I noticed that Mom was reaching under her skirt to unhook her stockings and then a short while later she wriggled out of her girdle and put it on the sofa between us. We four sat watching the movie for some time. I kept thinking about what my mom had said about doing what I felt I wanted to and then I picked up Mom’s girdle and held it against my chest. I reached forward and took ahold of Terry’s bra and then held that also. So I was watching the movie holding the girdle against my chest with one hand and holding the bra with the other. I expected to hear a comment from my mom or Terry but none came. My mom had to know that I was holding her girdle and I assumed that didn’t bother her. I guess she saw that as me expressing my need to be more involved with feminine things. If someone had asked me why I was holding the bra and girdle, I’d have to say that it was because I wanted to prove to myself that I could actually take action – even if it was kind of silly – to bring myself closer toward becoming a girl.

When the movie was over I was still clutching the bra and girdle. My mom stood up and said, “You can have my girdle tonight, but I need it back in the morning. I’m wearing a dress tomorrow and need to wear it.”

“When you’re done with my bra, you can put it in the hamper,” Terry said.

“OK,” I said feeling embarrassed. This was the first time that I had ever done this and I could see it was going to take some getting used to.

When I went to sleep that night, I arranged the bra and girdle on the pillow next to me and breathed in the slight perfumy scents. This was nice, I decided. I felt a rising happiness in that my future would be filled with wonderful opportunities to hold and admire my mom’s and sister’s clothing. The fact that they did not mind and perhaps encouraged me was the best thing of all. To have my mom’s pretty girdle to touch and hold and love, to imagine how her body fit in it, and yet without guilt or feeling that I was doing something wrong was heaven on earth. In the same way I loved imagining how Terry’s breasts filled up her bra cups. The very cups that were just inches from my face.

***

The next day I was sitting in the family room when Clara entered. She was waiting for Terry who was on an errand. Clara sat down next to me. One thing I had noticed about Clara was that she always wore unusually feminine skirts and dresses, while Terry was more likely to be wearing jeans than skirts. Terry’s skirts were uniformly straight and in solid, dark colors, unlike Clara’s much prettier skirts. Clara’s skirts had a way of swishing around her and, particularly when she sat down, I could see that she often wore lacy crinolines or petticoats underneath them. How girls decided what they wanted to wear on any given day was a mystery to me.

I watched as Clara neatly arranged her skirt when she sat down. It popped into my mind that I thought that her skirt was pretty and I decided that this was another example where I should not hesitate to act on impulse. I said, “I think your skirt is pretty.”

“Thank you, Greg. It’s one of my favorites.”

“You’re always dressed very pretty.”

“That’s so cute of you to say. Terry likes me to be pretty for her and I enjoy doing that.”

“She does? I didn’t know that. She mostly wears jeans, so isn’t it kind of strange that she likes you to wear pretty clothes?”

Clara laughed. “When two girls are together, like Terry and me, oftentimes one of the girls will be the pretty one and the other will be, shall we say, a bit more dominant. Not exactly a male, but more on the male side of the female spectrum, if you know what I mean.”

“That’s very interesting. Can I ask you how you knew that you would be the pretty one?”

“I’ve always loved pretty clothes even when I was very young. I like dresses that swirl around me. Particularly dresses and skirts that require a crinoline underneath so they have some body to them. I’ve always adored pretty bras and panties. Lace is my thing. It’s nice that Terry appreciates that side of me. She really loves when I make myself pretty for her.”

Everything that Clara said was a revelation to me and my mind was reeling trying to take it all in.

“You look astonished,” Clara said. “Did I say something wrong?”

“No, not at all. It’s just that you’ve made me wonder for the first time about the feelings I have about girls’ clothing.”

Clara laughed again. “I saw how you held your mom’s girdle last night and Terry’s bra.”

“I was being impulsive. My mom suggested that I allow myself to be impulsive to help learn about my true feelings about being male or female.”

“Wanting to hold a girdle and bra says a lot to me about who you are.”

“What does it say?”

“It says that you want to be feminine. Not just be a girl, but be a feminine girl. More like me than Terry. I always feel excited when I see a new pretty girdle for sale in a store. Something in me wants to own it and hold it and wear it. The way you held your mom’s girdle last night made me think that you wished it was your girdle. You were impulsively advertising that you wanted to be a girl who wore girdles and bras. Am I right?”

“I haven’t thought about wearing girls’ clothes. Last night I slept with the girdle on the pillow next to me. I was very happy it was there. When I woke up in the morning and I opened my eyes and I saw the girdle and also Terry’s bra I felt a wave of contentment and happiness run through me. I never previously thought of wearing the girdle and bra but now that I’ve heard what you’ve been saying, I’m pretty sure that I would put the girdle and bra on. I’d probably sleep wearing them.”

“You know what I think?”

“What?”

“Actually there are two things. The first is that you need to come to grips with the kind of girl you would want to be if you do become a girl. Secondly, after you’ve figured out the first question you need to talk to your mom about buying you your own bras, girdles, and other clothing. My intuition tells me that the girl struggling inside you to come out is very feminine. Much like me. You need to question yourself and come to some firm conclusion as to whom you are. Then, visit your mother and see if she’ll help you make that a reality.”

“Thank you, Clara! You’ve been wonderfully helpful.”

***

I took the homework assignment that Clara had given me very seriously. I thought about what kind of bras and panties I most liked. What kind of look I’d like to have if I was going to enter the female world. While I was thinking about this, I came to the conclusion that I needed to wear some girls’ clothing to help give me a better perspective on what I was searching for. A few days later in the afternoon I saw a bra and panty on the coffee table and I took them to my room to try on. I undressed and then stepped into the panty. It was white and made of a satiny material. Then I figured out how to put the bra on. An excitement rose up through me as I put the clothing on that suggested to me that I was indeed on the right path. My transformation toward female sexuality was not superficial. Deep currents within my psyche seemed to be governing my desires as evidenced by my giddiness. With the bra and panty on, I felt like I had finally taken a concrete step toward my mom and Terry. This was exactly the kind of change I was hoping for. I stood in front of the bathroom mirror and admired myself. It was clear to me that I would certainly be more fulfilled if the panties and bra were prettier. Clara was exactly right about that. I was the kind of girl who enjoyed being pretty. I would love to be admired by other girls for my prettiness.

I put my shirt and jeans on over the girls’ underwear and spent the rest of the day like that. Every time I reminded myself about the bra across my chest or the panty over my hips I imagined that Mom and Terry were feeling the same sensations. At long last I was now sharing similar experiences with the women in my life. If I could keep up with transforming myself, in no time at all Mom and Terry would see me as being another girl in the house. I’d then get included in all the girl things that they did.

I especially enjoyed having dinner with Mom and Terry while secretly wearing the bra and panty. During the meal I was a bit giddy and they both looked at me like I was a crazy. I couldn't stop myself from feeling the joy I was feeling. I went to bed wearing just the bra and panty and had a wonderful sleep with dreams of me flitting about as a girl among other girls. I was awakened in the morning by my mom. She always got up a little ahead of me so she could go to work. “Good morning Greg.”

“Good morning,” I mumbled.

“Have you seen the bra I left on the coffee table?”

I nodded my head. “Good. I need to wear it to work today. Where is it?”

I pulled the cover off of me and sat up. My mom laughed, “Mystery solved!”

I took off the bra and handed it to her. “Thanks Greg. I can see that I’m going to have to take you shopping for your own bras and other clothing. While I don’t mind you wearing my bras and panties, your own lingerie will fit you better. Also, sharing panties is a bit unsanitary”

“I’m sorry, Mom,” I said. “It’s just that you said I should go with my impulses.”

“I’m not at all upset, Greg. I think you have a cute body and you look nice in the bra and panty. I’m actually happy that you’ve taken this step apropos of our previous talk. You seemed bottled up then and now I can see that you’re letting yourself experiment with your sexuality. Let that take you wherever it wants to go.”

“Thanks, Mom.”

“The only problem is that I don’t have time to do the kind of careful shopping with you to make you happy with what you buy. Maybe Terry could take you. I’ll give her a credit card and she can make sure you get some nice things to wear.”

“Thanks, Mom. I really appreciate it!”

***

The next evening I went to speak to Terry. Clara was there with her. I said, “Mom and I were wondering if you could take me shopping for my own girls’ clothes?”

“What’s that Greg?”

“Mom says it’s better if I have my own girls’ clothing than to wear hers or yours. The other night for the first time I wore Mom’s bra and panty and really liked it. That’s why Mom thinks I should get my own clothing. She’s busy right now and can’t take me.”

“I’d love to take you but I’m fighting a deadline with a project I’m involved with. In a few weeks I’ll have the time. Can you wait that long?”

“Oh, sure,” I said. I suppose my voice sounded a bit dejected.

“I have plenty of free time,” Clara said. “If Greg doesn’t mind shopping with me, I’d be happy to help him buy some girls’ clothes.”

“Wow! Would you? Terry, do you think Mom would let me shop with Clara?”

“I’m sure she would,” Terry said, “but go ask her to make sure.”

***

I found Mom and asked her if it was all right for Clara to take me shopping since Terry didn’t have the time. “It’s okay with me, Greg, but I hope you understand that Clara is a very feminine girl. I’d hate for her to steer you to clothing that isn’t what you prefer.”

“But Mom. I talked with Clara the other day and I’m pretty sure that she and I love the same kinds of clothes.”

Mom stared at me for a few seconds and said, “You know, Greg, I never thought about it too much but I can see it in you. The way you adored my girdle and Terry’s bra showed that you have quite a strong feminine bent to you. So okay. Go ahead and have a fun shopping date with Clara. I don’t doubt that you’ll return with a lot of pretty clothes to wear.”

I excitedly went to Clara to arrange our excursion. Mom gave her a credit card to use, with the caveats: “Don’t go crazy” but “Make sure that Greg is happy.”

***

I never had so much fun in my life as I did shopping with Clara. She and I saw eye-to-eye on virtually everything. We both made bee lines to the prettiest bras, the prettiest panties, the prettiest girdles, and other foundation garments. She loved lacy slips like I did. She introduced me to crinolines, petticoats, and pretty dresses that I could wear over them giving me the sweet look of a young party girl. We bought adorable shoes for me. We even decided on what size bosoms I should have. She said that Terry was a D cup, my mom was a DD and she herself was a C. “We’ll get you falsies or breast forms so that your bra is filled, no matter what size it is.”

We ruled out being as big as my mom since it wouldn’t be nice to get into competition with her. Clara said that Terry wasn’t competitive about bra size. She probably wishes she had smaller boobs! Clara and I couldn’t believe that anybody would want smaller boobs! “We’re two peas in a pod, Greg,” Clara said. So I chose to have D cup bras and we found some D cup falsies to fit them. Clara said I should send away for D cup breast forms that would add some natural weight to my breasts. They weren’t cheap and I’d have to see if my mom would pay for them.

After a flurry of buying we were sitting at a table in the food court having our lunch when a girl who was somewhere between Clara and me in age stopped by to say hello to Clara. She was strikingly pretty and was wearing hip-hugging black leather pants and a tight black leather jacket. “This is Diane,” Clara said, “and this is Greg. Greg is Terry’s younger brother.”

“Great to meet you,” Diane said. “I’ve heard a little about you over the years. It’s nice to put a face with a name.”

Clara invited Diane to sit with us and she said she would stay to have a coffee. While she went to the Starbucks, Clara said, “Diane is Julie’s younger sister.” Julie is a mutual friend of Clara and Terry’s who I had met a couple of times.

“I didn’t know that Julie had a sister. She’s very beautiful,” I said.

“Isn’t she, and very cool.”

“I could see that. Her leather outfit is fantastic, though not for me!”

“Right. I wouldn’t mind it at all if Terry wore something like that!”

Diane came back and joined us. She looked at some of the packages next to us and said, “Your dress shopping, Clara?”

Clara laughed, “Yes, but they’re for Greg!”

“Really now?”

“I’m sorry Greg. You’re not embarrassed are you?” Clara said. “It’s okay to tell Diane.”

I looked at Diane wondering if I should talk about myself. Diane said, “Tell me why you’re getting dresses. I’m actually bi, so I’m certainly sympathetic to people with different ideas about their sexuality.”

“It’s kind of complicated,” Greg said.

“Complicated?” Diane asked.

“Greg’s just sixteen,” Clara said, “and he’s just begun to discover himself. So this is all very new.”

“I see. I’m eighteen, Greg. It wasn’t until I was your age when I figured out that I also liked girls.”

I found myself strongly drawn toward Diane. There was an excitement about her, a charisma that made me want her to like me. “I’ll try and explain,” I said. “You see, growing up with my mom and Terry I’ve come to see that girls are at a higher level than boys.”

“You’re a smart one,” Diane laughed.

“Isn’t he!” Clara said.

“Right. I’ve felt that this distance between me and girls has made me feel kind of lonely. I should make clear that just living with Terry and my mom has drained away whatever boy characteristics I had. They are so forceful my maleness could not compete against them. My problem was that my boyhood was not replaced by anything else. I told Terry and my mom how I was feeling and one thing led to another and I decided that what I needed to do was emulate them. By learning how to be like a girl I would close the distance between me and them, besides making up for my lost maleness.”

“That’s quite an analysis! You’ve given this a great deal of thought,” Diane said.

“Yeah, thanks.”

“So there are many different kinds of girls. Which kind do you intend to be?”

I laughed. “That’s the easy part! Clara is my role model. I’ve always loved the way she dresses and today she helped me select pretty clothes just like she wears. I’m so happy!”

“Greg and I are two peas in a pod!” Clara said.

“I’m sure that Clara is the kind of girl I want to be,” I said.

“And that is …” Diane said.

“The pretty one in the couple!”

“I explained to Greg that when two girls are together, oftentimes one is the pretty one and the other is more in the dominant role.”

“True,” Diane said.

It was exactly at this moment that my eyes and Diane’s locked on each other’s. I could see plain as day that she was thinking that I would be the ‘pretty one’ in any future relationship between us. Besides being older than me by a couple of years, Diane would without a doubt be the dominant partner. Everything about her screamed that she would be in control. I found myself feeling faint with the intoxicating thought that maybe Diane was attracted to me and would want to get to know me. I wondered if she would want to ask me out on a date.

“I have to run along,” Diane said and got up. “It’s nice meeting you, Greg, you’re a very interesting boy.” I felt panic that Diane was just going to leave and I’d never see her again.

“Thank you, Diane, I really, um …” I said, not knowing how to signal that I liked her.

Diane handed me her cell phone and said, “Type in your number Greg. I’ll call you.”

I went from depression to bliss in one second as I entered my number. After Diane had left us Clara said, “I think she’s got you in her sights, Greg. Women like her have a weakness for pretty girls. The fact that she’s bi and you’re also a boy just makes it that much better.”

“I really like her. She makes me want to be as pretty as I can for her.”

“Now that you have these pretty clothes, I think you can be everything she’s hoping you’ll be!”

***

When we came back home after our shopping excursion, my mom asked me to give her and Terry a fashion show after dinner. Clara and I were very excited to oblige. Clara would act as an announcer to describe each of my outfits for the audience. I would strut around the living room as if on a runway at a fashion show. For my first effort, I wore just a bra, panty, and high heels. Clara announced, “First up is our sexy lingerie model, Greg. He’s wearing a beautiful matching pink bra and panty set by Prima Donna.” She went on to describe every detail of my outfit as I glided around the living room doing my best to imitate what I’d seen of models. Having falsies in my D cup bra sealed the deal insofar as making me feel like I was a girl. Mom and Terry laughed and applauded. Subsequently I modeled a few other bras, panties, and girdles with stockings. I modeled my garter belt and then when the lingerie section was done, I moved into showing off my skirts and dresses. In my prettiest dress I felt like a princess. Clara coached me to curtsey to Mom and Terry which I did successfully after daintily holding out my skirt and crinolines to each side. After an hour or more the show was over and Mom rushed up to me giving me a bone-crushing hug before I could take off my dress.

***

Every day after having met Diane I anxiously waited for her to call me. Four days came and went without her contacting me and I was settling in to accepting the fact that she would never call, when my phone rang from an unfamiliar number and I answered it, “Hello?”

“Hi Greg, this is Diane.”

“Oh hi!” I said and pumped my fist in the air.

“I enjoyed meeting you the other day.”

“I loved meeting you also.”

“I’d like to take you out for a coffee.”

“I’d love that.”

“How is Saturday at 2?”

“That would be great. There’s just one thing.”

“What’s that?”

“Are you expecting me to be wearing my pretty clothes?”

“No, Greg. You can dress any way you want.”

“It’s just that I want to eventually always be wearing my pretty clothes, but so far I haven’t worn them outside the house. I didn’t want to disappoint you.”

“That’s very sweet of you Greg. I’m happy just to be with you.”

“Thank you, Diane. I’m still learning about being a girl so I’d be a little nervous to be outside in a dress.”

Diane laughed. “I understand what you’re going through, Greg. I don’t mind seeing you dressed as a boy or a girl, though – when you’re ready for it – I’d love to see how pretty you are in one of the dresses you bought with Clara. I’ll bet they’re very pretty.”

“Yes, they are.”

“I’ll love seeing you in them.”

***

After I hung up the phone with Diane I went to my mom. “I’ve got a date to get coffee with Diane on Saturday afternoon. Is that okay?”

Mom smiled at me. “That’s lovely, Greg. Your first date. Tell me about Diane.”

I explained how I met her. “She’s eighteen. That’s not too old for me to date is it?”

“You’re only two years apart. I think it’s fine.”

“She’s going to pick me up in her car.”

“That’s convenient.”

“Thanks, Mom. You’re the best.”

***

Diane picked me up in her car and we went to a café to get coffee. She was wearing tight blue jeans and the same black leather jacket I had seen her in before. The spark that had been between me and Diane when we first met continued to grow during our date together. I learned that Diane was adventurous and had dated quite a bit before. Mostly guys until she realized that girls offered much that she couldn’t get from guys. Recently she had dated whomever she liked without concern for their sex. She said that I stuck out in her experience as someone who was singularly thoughtful, interesting and of a gentle, feminine nature that complimented her own more aggressive tendencies. “You’re an unusual boy, Greg. I’m intrigued by the way you’ve thought about how you fit within your family situation. That’s quite rare for anybody and especially for someone your age.”

“Thank you , Diane. I think you’re very exciting and know so much!”

Diane stared intently at Greg and said, “It’s so much to your credit that you’ve realized so clearly and definitively that girls are superior to boys. Most boys operate under the false idea that their muscles make them the superior sex. Let’s face it, as strong as any boy is, if he wants to wrestle with a great ape he’s going to lose. On the other hand, the wisdom held by girls exceeds that of both boys and every great ape out there.”

“That’s exactly why I want to do everything I can to make myself as close to being a girl as I can.”

“I imagine that you’ll be a very cute girl.”

“I hope you can get to see me wearing the pretty clothes that I bought with Clara. I’d love for you to visit me on movie night. I’m sure that my mom, Terry, and Clara would also love for you to be there. We watch movies together. Romantic movies. I hope you like those.”

"It sounds like a lot of fun and I would be happy to go. The kind of movie is not so important to me as is the chance to spend a nice evening with you. And specially to see how pretty you are in your favorite dress.”

The air around Diane and me was sizzling. I felt my heart beating rapidly. If she had leaned in and kissed me I would have been on seventh heaven. The moment passed and we got up so she could take me home. As we walked toward her car, she took my hand and held it. This was a first for me and in the magical touch of her hand I knew that she and I were destined for a loving future.

When she dropped me off we made plans for when she would come to movie night. “I’m so looking forward to you coming,” I said.

Diane smiled at me and gave me a brief kiss on the lips and I nearly cried for joy. I watched as she got back in the car and drove off.

***

With Diane due to show up for movie night in a couple of hours, Clara and I got together to get me fixed up. She fully appreciated what a big night this was to be for me. After I was all bathed Clara and I discussed which of my bras and panties I ought to wear. Then we had an important decision to make as to whether I should wear my prettiest girdle or my garter belt. In either case I’d wear my sexiest stockings which had a French heel and a black seam that went up the back of my legs. Clara thought that the stockings alone would slay Diane’s heart! We debated the pro and cons of girdle vs. garter belt and finally decided on the girdle. Wearing the girdle would encourage me to be a bit more chaste than I would be with a garter belt. My loins would be well protected by a girdle in case Diane and I got carried away. Clara thought that Diane and I needed to push off until a further date any serious petting, lest we get the wrong idea about each other. “Build slowly. Create some tension. It will do you a lot of good in the long run.”

I stepped into my girdle, attached the hook and eye closures, and then zipped it up. Clara had opened the package of new stockings and she helped me align the heels and then slide them up my legs so the seam was straight and over the center of my calves. I attached the stockings to the girdle. Next was my bra and falsies. Then I stepped into a luscious petticoat and finally my dress in all its feminine glory. Clara went around me plumping up my skirts. She helped me put on some basic make-up. I was still learning how to do that and didn’t want to risk messing up. My hair was now girl length and my mom and Terry had helped me style it so it framed my face. Clara brushed it a bit and then I put on heels that matched my dress. I looked in the mirror and tried to be objective as to the way I looked. Clara said that I was absolutely gorgeous and after studying myself for a minute I decided that she was right. I think I made a fairly pretty girl. I was ready for Diane.

Clara and I waited in my bedroom for Diane to arrive when I could make my grand entrance. I confided in Clara that I had never kissed a girl before and Clara gave me some dos and don’ts. Relax and enjoy it. Let Diane take the lead as she surely will. Accept her tongue in your mouth and gently suck on it. Don’t slobber or use your teeth. The main thing is to be responsive to what she does. She sees you as a warm inviting feminine flower that will envelop her in love. That’s what dominant girls want from their lovers. “I supply it to Terry every way I know how and she laps it up. It’s a thrill for her to take charge just like it’s a thrill for me to have her in control. I think you and Diane are going to be the same way.”

“I hope you’re right.”

“Look into her eyes when she first gazes upon you wearing this pretty dress. You’ll see hunger and you’ll know that everything I said is true.”

Just then I heard the downstairs doorbell ring and then heard my mom talking to Diane. Then I heard Terry join in the conversation. I think I heard Julie’s name being mentioned. “You’re very pretty, Greg,” Clara whispered to me. “You’re going to make a great impression on Diane. I guarantee it.”

“You really think so?”

“I do. You’re as pretty as they come. Your dress, sexy bust, and fancy stockings all come together perfectly.”

Mom called up to me that Diane was here and then I walked with Clara holding onto her bent arm to stabilize me in my heels as I walked downstairs. Mom and Terry came to the foot of the stairs and saw me at the same time. “You’re an absolute doll, Greg!” Mom said. “So pretty!”

“Thank you!”

“Just the prettiest piece of fluff!” Terry said and laughed.

I crossed the threshold to where Diane was waiting. I looked into her eyes and I could see immediately that she knew she was lucky to have a girlfriend as pretty as me. “Oh my God, Greg! You’re so gorgeous! Let me get a good look at you.” Diane circled around me taking in the whole picture. Terry, Clara, and Mom wandered off to get the snacks ready for our movie night.

“I’m so happy that you like how I look!” Diane was once again wearing her skintight black leather pants and jacket. “And I can once again see how exquisite you are in black leather. It’s so dreamy the way it accentuates your shape.”

With just the two of us standing there, Diane put her arms around my waist and drew me in to her. My heart was fluttering in anticipation that she was going to kiss me and sure enough, I nearly swooned as she brought her lips to mine and gave me a tender kiss. I knew now for sure that our movie night was going to be everything I dreamed that it would be.

Diane and I joined the others in the family room. I held out my skirts and primly sat down on a love seat that was just to the side of the sofa. Diane sat down next to me and slid over a couple of inches closer to me. My skirts and petticoat bunched up a little over her thigh. We looked at each other with a kind of delightful rapture. The future looked especially bright for our relationship. Mom, Terry, and Clara sat on the sofa. In front of us was some food and drinks. Mom started the movie. Diane and I watched the beginning. It was about a prince from an imaginary tiny European country who falls in love with an American girl – a commoner. The king and queen, the prince’s mom and dad are none too pleased, but there isn’t too much they can do about it.

We were not too far into the movie when Diane put her arm over my shoulder. I turned to look at her and she moved her lips towards mine and gave me a sweet and tender kiss. Then I felt her tense up and her arm pulled me in harder and then she planted a passionate kiss on my lips. It went on for a minute or two during which time I did everything I could to offer my compliant response to her. She was the key and I was the lock. She entered into me and opened me up second by second. Diane took a break from the kiss and watched the movie for a few minutes. I felt tingles shooting off in my body in anticipation of Diane’s next kiss. When it came with a slow rising fury my eyes shut and I felt my body floating on the end of Diane’s soft lips. And then I felt her tongue enter my mouth and I had to exert the greatest self-control not to emit a loud moan of pleasure that would surely have caused my mom to pause the movie. Luckily I caught the sound before it left my throat and I enveloped Diane’s sweet tongue with my own and with my mouth and I am sure I was happier than I had ever imagined a person could be.

The first tongue kiss was followed by endless more. At some point in the movie Diane had taken my hand and guided it up inside her leather jacket to rest on her breasts. Her hand then found my own and I applied the same pressure to her breasts that she did to mine. I was resolved to learn by example.

When the movie was over and the lights came on, I was leaning on Diane with my head on her shoulder as she held me. My Mom said, “Greg looks sleepy.”

“He’s had a big day,” Diane said.

I stirred and said, “I loved the movie, Mom.”

Everyone laughed at the joke. Diane helped me to my feet and I said good night to Mom, Terry, and Clara. I walked with Diane to my bedroom where I thanked her for a wonderful evening. She said that she was the one who needed to thank me. “You need to get to bed. Let me unzip you.”

I yawned and sleepily turned around as Diane pulled down the zipper on my dress. Then she gave me one last kiss and she left saying, “I’ll call you.”

I sat down on my bed, and slowly lifted my dress over my head. Then I hung it back up in my closet. I stepped out of my crinoline and hung that up also. Then I detached my stockings and carefully took them off, then slid out of the girdle. I washed off my makeup, brushed my teeth and went to bed wearing my bra and panties. All during the night Diane appeared in my dreams. Each time I thought of her I felt a moment of euphoria and surprise that I had been so lucky to have met her.

***

A few days later Diane took me ice skating with her. I wore a cute ice-skating outfit with a short skirt, white tights, and white ice skates. It was my first time outside the house wearing my girl clothes. Diane applauded my courage and told me not to worry. She would be there for me and I believed her. As we skated around the rink Diane held my hand. She didn’t let me fall and so we had much fun together. Afterwards we went for coffee.

As we sat in the café I thought about how much closer Diane and I were getting to each other. There would be a time where the fact that I had a penis might come up in some way or another. I wasn’t sure what the circumstance might be, but it seemed inevitable. Diane said to me, “I can see you’re thinking about something that’s worrying you. Tell me what it is.”

“Worrying me?”

“Don’t be coy, Greg. You can tell me anything.”

“I was just thinking that I like being a girl, and especially the kind of girl that you like. But you know that some aspects of me I can’t change.”

Diane looked at me for a minute and said, “Oh, I see. You’re referring to your penis?”

I blushed and she said, “I’m sorry for being so dense, Greg. The short answer is that as I already told you, I’ve liked both boys and girls in the past. The fact that you’re a combination of boy and girl is neat and hardly an issue for me.”

“It isn’t?”

“You could be a hundred percent girl, or hundred percent boy or the way you are and I can imagine myself dating you. Of course, I like you dressing pretty. That’s definitely a bonus for me!”

I wondered when and if there would come a time when Diane would want to experience my penis. And what of her body? I had to admit that I was curious to see it.

***

Now that Diane and I are dating regularly, it seems as if my life is divided into days when I’m seeing Diane and days when I’m dreaming about seeing her. One day, a couple of weeks after our movie night when I wouldn’t be seeing Diane for several days, I reprised my movie night outfit. When my mom saw me she said, “Aren’t you the pretty one again! This is so nice Greg. I’m thrilled that you’ve found a way to express the girl feelings that are within you. It’s also nice that you’re wanting to be my feminine daughter. As you know, Terry is a take charge girl with a strong will, so I haven’t had the luxury of having a delicate and feminine daughter. It’s so nice to finally have one.”

I wrapped my arms around my mom and gave her a hug. “I love you Mom.”

“You see, Greg. This is exactly the affection that feminine daughters give their moms. It’s so nice.”

“For the longest time I’ve wanted to feel close to you and Terry and now I do. I’m so happy about that.”

***

That evening I sat between my mom and Terry on the sofa as we watched a rerun of Gilmore Girls. When it was over Mom said, “Lorelai and Rory are such pretty names. You know, Greg, now that you’ve become my daughter, I think you ought to change your name.”

I felt a jolt of excitement from my mom’s suggestion. “Change it?”

“To a girls’ name.”

“I never really thought about it, Mom. It does sound like a good idea.”

“Let’s call you Rory,” Terry said.

“I like that too,” Mom said.

I thought about it for a minute and said, “Yes. I love the name Rory. I also love being named after Rory in Gilmore Girls. I think she’s pretty and I like a lot of her clothes.”

“Good. Then we’ll address you as Rory from now on,” Mom said.

“Aren’t there many other things that Rory could do to be a girl, besides dressing up as one,” Terry said.

“What does she mean, Mom?” I asked.

“It’s been in the back of my mind also. You see, Rory, there’s a whole science devoted to helping boys become girls.”

“There is?”

“Yes. There are number of things that could make you more like a girl. Some are easy to do, some are more difficult.”

“The most difficult is turning your penis into a vagina!” Terry said.

“What? That can be done?”

“Yes. But it’s something that you don’t go into casually.”

“There’s no reason to think about that now, Rory,” Mom said. “You should start out doing some of the simpler things.”

“Like what, Mom?”

“We could send you to get your facial hair permanently removed by a laser, for example. Also, you could start on hormones.”

“Hormones?”

“Doctors can give you a hormone that blocks your boy testosterone and then after a couple of months they can start giving you girl hormones. Estrogen and progesterone. Then your body fat will begin to rearrange itself making your hips wider and you’ll grow breasts.”

“Grow breasts? Holy cow, Mom. I would love to grow breasts!”

“They won’t be D cup, Rory. Perhaps a B cup will develop.”

“Rory could turn the B cup into D cup with some plastic surgery,” Terry said.

“Yes, of course. That’s definitely a good idea, Rory. No doubt you’re the kind of girl that would really like to have D cup breasts.”

It was true. Nothing would make me happier than to have large breasts. I supposed Diane would take advantage of them for her pleasure.

“Hormones will make your skin softer and silkier like a girls,” Mom said.

“Gosh, I’d love that.”

“There are also operations that could further femininize your face and raise the pitch of your vocal cords.”

“I think I’d love to definitely get the hormones. It would be great to have real breasts in my bras.”

“I’ll set up an appointment with your doctor. You have to get his approval and probably that of a psychiatrist.”

“I do?”

“I can’t imagine a boy who is more deserving of having estrogen than you Rory. I’m sure the doctors will agree with me once they meet you.”

“How fast do you think I’ll get breasts?”

Mom laughed. “Patience, Rory. Maybe six months from now you’ll have some A cup breasts. A year from now B cup. Then you can decide if you want surgery to get D cup.”

An image came into my head of Diane with her hands on my new breasts. She was touching them gently and looking upon them with love. How nice it will be if that future becomes reality?

“How about another episode of Gilmore Girls?” Mom asked.

Terry and I agreed. A few minutes into it I was aware of Mom taking off her bra and then a few minutes after that, Terry did the same. Then I reached inside my dress and unhooked my stockings and took them off. Then I reached in and found the zipper on my girdle, slid it down, unhooked two clips and then wriggled my girdle off from underneath my dress and petticoats. I put the girdle on the coffee table next to Mom’s and Terry’s bras. Without the girdle on I could breathe a bit easier and it was nice to take it off after wearing it so many hours. I’m a girl now, just like Mom and Terry, I thought. In every way I’m now a girl.

To be continued …