Weekend Daughter

By

Pamela

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My mother, may she rest in peace, was a very beautiful woman. She had done some modeling and been in some theater productions and even a couple of movies, but then she decided she wanted a quieter life. She met and married my dad and had me, Greg, a son. Unfortunately, my dad was a philanderer and when I was about 5 he left to never be heard from again. Though, many years later, I did receive a small inheritance from him after he died. With the money was a brief letter he had written to me, apologizing for depriving me of a dad. Too little, too late was all I could think. To help my mom survive after dad left, my mom went to nursing school and became an RN, a career from which she earned a decent living. So, for most of my childhood, my mom and me were our entire family.

When I was nine, my mom had an itch to move to the outskirts of town and she bought an old farmhouse with ten acres around it. We were fairly isolated just the two of us in our farmhouse. My mom was an affectionate woman and I know that she loved me. Having said that, I also think that my mom may have had a slight preference for a daughter over a son, mainly because there are things that a mom and her daughter can naturally do together, that a mom and her son can’t. That slight itch of regret that she didn’t have an opportunity to share girl things with her daughter I think preyed upon her judgement and in time caused her to take some liberties with me that society may not approve of. Personally, I am eternally grateful that my mom was willing to bend society’s rules to create a life for me that has been so filled with happiness and love that it’s worth telling the world about. And that is what I intend to do here.

As I mentioned previously, my mom was very beautiful. She wasn’t like the moms of any of the other kids I knew and played with. She had a face that was warm and pretty and she had luxurious light brown hair that she kept long. Her figure was so extraordinary that even I could sense at my young age that being in her presence was a cause of a kind of pleasant arousal – even though I didn’t really understand or know anything about the anatomy of women. I seem to have had an almost animalistic response to the delightful large round shape of her breasts and the perfect oval of her rear end. Mom had a thing about wearing very tight tops that would effectively reveal her amazing figure. I was aware of the little bumps in the middle of her breasts that I would later learn were her nipples.

My mom saw me as her son, her cute little man, a boy with interests no different than those of any other boy my age. But inside my mind I sensed I was with an extraordinarily sensual woman, and even if I was years from puberty, I developed a kind of crush on my mom. Not a sexual crush involving a sex act, per se, but an emotional, loving crush that manifested itself by close human to human affection. I loved to spend time with her. Especially because we lived in our farmhouse, just the two of us, we were sort of like on a desert island together, particularly on the weekends.

Sometimes at night when I started to get sleepy, mom would encourage me to lie down with my head in her lap. I became especially intoxicated by the warm motherly presence that existed between her lap and her breasts. As was the style in that era, my mom liked to wear wide flowing skirts that would be puffed up and out by crinolines. Sometimes with my head in her soft lap she’d have to reach forward for her wine glass or the phone and then the back of my head would be surrounded by her skirt with the rustle of crinolines underneath my ears and my face would be trapped in her breasts. Her breasts would be pushing down hard on my face. You don’t know what happiness is until you’ve experienced this pleasure.

One time my mom had gotten some bad news about a friend’s divorce and she had stayed on the phone, leaning forward and concentrating on the conversation for a half hour while my head was being crushed by her breasts. By the end of the call, I was nearly weeping with happiness and when my mother realized that I was caught in her lap she laughed and said, “I hope I didn’t smother my little man!” If I had had to check out at that time, I could not have imagined a more perfect way to go.

In the summertime, if it wasn’t so hot at night that we needed to run the air conditioner, my mom would turn on a fan in the living room and she’d dress in one of her pretty nighties and I’d be wearing my short pajamas. The silkiness of my mom’s nighties would be electric on my skin, and even though I didn’t really appreciate what was going on, I seem to remember that her large breasts had a warmer, softer, more pliable feel to them in the summer compared to how they felt when she was fully dressed in the winter. Years later I realized it must have been because she didn’t wear a bra with her nightie. I distinctly remember the feeling of nuzzling her breasts with my cheek and feeling them push back against me.

Our routine most mornings was that we got dressed in our bedrooms and met together for breakfast. One day when I was ten I woke up remembering that I needed to ask mom a question about school and I accidentally walked into her bedroom while she was in the midst of dressing. My view of her lasted only a few seconds, but what I saw seemed to be my mom wearing pink underpants and a pink thing that she was just placing over her breasts. I had never seen a breast before, except when I was nursing as a baby, and the sight of them startled me. My mom reflexively chased me from the bedroom telling me to knock in the future. I felt terribly embarrassed by my invasion of her privacy.

That evening when I was sitting next to my mother on the sofa I said, “I’m sorry for barging in on you this morning.”

My mother laughed, and said, “I was a little embarrassed, you catching me in my underwear.”

I must have looked puzzled and she said, “I was embarrassed because this is one of those things that mom’s and daughters share but not mom’s and sons!”

“I don’t understand.”

“Moms and their daughters might see each other in their underwear, but moms and sons don’t. That’s all I’m saying.”

“Sons can see their dad’s underpants, but their daughters can’t?”

“Yes.”

“Why is that?”

“It has to do with reasons you’ll understand when you’re grown up.”

“What reason?”

“You know that girls and boys are different in some ways, don’t you?”

“Yes.”

“It’s because of those differences.”

“What other things do moms and their daughters do together that we cannot do?”

“You know, off the top of my head, share clothing, discuss the different dresses we wear, or our shoes. Go shopping together. Our hairstyles, makeup, fingernail polish. Girls also like to go to spas, and we can all be brides or flower girls or bridesmaids, while a son cannot. We also have biological things that we share, like that time of the month when we menstruate. Also, we fit into society differently than men and we can talk about it from the same perspective. There are lots of things.”

“I had never realized that!”

My mom’s face revealed that she understood that she had over done it and probably said things that would make me feel like she really regretted my not being a girl. “I’m sorry. Don’t ever think for a second that I’m not totally happy that I have you as my child!”

“If you had a daughter, would her underwear be like the pink underpants you were wearing and would she be wearing that pink thing on top?”

“You mean, like you saw mommy wearing this morning?”

“Yes.”

“First of all, girls underpants are called panties and what you called the thing on top is my bra. Girls wear panties and bras while boys wear underpants. My bra and panty today just happened to be pink. I have bras and panties in many other colors also.”

“Why do girls wear a bra?”

My mom blushed and pointing at her chest, said, “Girls have breasts.”

“Boys don’t have breasts?”

“Boys have breasts, but they don’t get big like for girls.”

“Why don’t they get big?”

“Girl’s breasts make milk that is fed to little babies. Boy’s breasts don’t make milk so they don’t have to be big.”

“But why do you need a bra?”

“It’s more comfortable for girls to wear a bra. Otherwise our breasts can move around.”

“That’s uncomfortable?”

“Yes, it can be.”

“If I was a girl, then if I had walked in on you in the morning and saw your panty and bra, it would be okay?”

“Yes, it would have been fine.”

“Do you wish that I was a girl so we could see each other’s underwear?”

“What a silly question. I love you exactly the way you are.”

“But, do you miss not being able to do all the things that mommies do with their daughters?”

“I suppose, a little, but that has nothing to do with you!”

“But it makes me sad that you don’t have a chance to share girl things with your daughter.”

“There’s no reason to be sad.”

Except that I perceived that there was a slight melancholy that my mom could never shake off because her lot in life was to have just a son and never have a daughter. Then it hit me like a ton of bricks: it was a two-way street. She might not be able to get the special feelings that come from having a daughter, but then I was missing all the special things I could get from my mom if I had been a girl. Both of us were being deprived of some really special things. I pondered what I could do about it.

***

The next time my mom was doing the laundry I joined her just as she finished folding up the clean clothes and had them arranged in piles on her bed. In front of me was a stack of my white underpants and I saw that there was a stack of her panties. I also saw that she had a few bras that she had folded up.

I said, “My underpants are all white and it looks like your panties are white and blue and beige and pink.”

“You’re so observant dear, but a mommies panties are usually not a subject of conversation for little boys.”

“I’m sorry mommy. I was just thinking about what you said the other day. If I was your daughter then it would be okay for me to talk about your panties?”

“Yes, I guess so. Look, I’m not saying that there is some kind of hard and fast rule that boys cannot talk about their mommy’s panties, while girls can. I’m just saying that it’s not usually what boys would talk about.”

“Do you wish that you had a daughter who you could talk to about panties?”

“Didn’t we discuss this the other day?”

“Sorry, mommy.”

My mother looked at me and came over and gave me a hug. “I think I’ve been making you feel guilty for being a boy, which is the last thing I would ever want to do.”

“But what if you allowed me to talk about panties? Then you’d be able to talk about panties like you could with a daughter, but I’d still be your son.”

“I guess that’s fine with me, but I’m not really getting why you want to talk about panties?”

“It’s just that I wish that I could experience some of the special things with you I’d get to know if I had been your daughter.”

My mother sort of made a gasping sound and put her fist to her mouth. “I hope I have never kept you away from me because you’re not my daughter?” Before I could say anything she added, “But it does make sense that you’d feel like we’re not as close as we could be if we were mother and daughter.”

I didn’t say anything as my mom was clearly thinking and then she said, “Okay. From now on if we want to talk about panties we’ll talk about panties. In fact, mommy promises that she’ll try and have with you all the same closeness that she would have with a daughter. How’s that?”

“I love you, mom,” I said.

“My little man! So why don’t you help mommy by putting my panties back in my dresser drawer? That’s exactly the kind of thing that I’d ask my daughter to do!”

I happily opened my mom’s dresser drawer and saw that there were a couple of piles of panties on the left and then some bras next to them and then on the right were some other folded up garments that I couldn’t identify.

“Where do the panties go?”

“Sorry. Put them underneath the panty pile on the left. Mommy likes to rotate through her panties one by one so they wear equally.”

“So if you’re wearing pink panties it’s just because they happen to be the panty on top of the pile?”

“Yes, you could say that, but sometimes mommy looks for a particular panty that she wants to wear.”

“Because you want to wear that color that day?”

“Sometimes that might be true. Some of mommy’s bras and panties form a set. So if I was wearing a bra that had a matching panty, I might want to make sure that I’m wearing the set.”

“So girls sometimes like that their bra and panty match?”

“Yes, you could say that.”

“Wow. I never knew that. Are there other reasons for wanting one panty over another?”

“If you looked at mommy’s panties you’d see that there are different types. Look, are you really interested in this?”

“Yes, mommy. I want to know everything you know about panties. If I was your daughter, wouldn’t you teach me this?”

“You’re right. My daughter would learn all about the different kinds of panties. Besides what I taught her, she would learn a lot by experience. When we went shopping for her panties, she would try different kinds and learn about them.”

“So mommies go panty shopping with their daughters?”

“Yes, of course.”

“Oh,” I said and looked at my mom.

After a few beats she said, “Don’t tell me you want to go panty shopping with me?”

“That’s what you would do with a daughter.”

My mom shook her head and laughed. “You’re right. You and I need to experience the fun of mommy daughter panty shopping! Actually, that’s one of those things that I had to just put out of my mind up until now. We’ll go this weekend!”

“Thank you, mommy.” I couldn’t remember being as excited as I felt that moment, since a whole adventure in shopping with my mom would be happening in a few days’ time.

“To finish our discussion, girls panties come in several different styles depending on how much of the tush they cover and where on the waist they sit. Bikini style are usually my favorites. They’re kind of small.” My mom fished one out of her panty drawer and showed me. “You can contrast this to one with more full coverage,” and she held up a panty that was more of a bloomer type. “Somedays mom needs to have the larger panty because she’s menstruating and needs to put a pad in her panty.” My mother looked at me and said, “I can see that you’re lost. Remember, you want me to be as forthcoming with you as I would be with a daughter and this is a perfect example of the kind of conversation that I would have with a daughter.”

“I’m very interested, it’s just I don’t know what menstruation is and why you need a pad in your panty. To take notes?”

My mother laughed uproariously. “Pad? Not a pad of paper. A menstrual pad. How can I explain? Look, if you were my daughter you would have a vagina.”

“A vagina?”

“Yes, girls have vaginas. I’m surprised you don’t know about that. Anyway, where you have a penis, girls have a vagina which is like a little tunnel. Babies come out of the vaginas of mommies. Let me just simplify this. Each month a mommy has the chance to make a baby. Part of this is that her body gets ready for the baby in case she’s going to have one. She saves up some blood that baby would need. If she doesn’t get a baby that month, then her body releases the unused blood out of her vagina. Menstrual pads absorb that blood and mommy likes to wear a larger panty when she uses a pad because it won’t fit very well in a small panty. Is that clear?”

“Yes, mommy, but I don’t understand what decides if mommy is going to have a baby or not each month.”

“That’s were the boys come in. Mommy and a daddy have to decide they want a baby, and if so, they then get it started that month in mommy and she doesn’t menstruate again until after the baby is born. It takes nine months for the baby to come out.”

I was having a hard time grasping what my mom was talking about. I couldn’t see what the boy would have to do to get mommy to have a baby. I decided that it was probably better not to ask since it sounded scary. “How much blood comes out of you, mommy?”

“It can take a few days for all the blood to leave me, so I guess it could be a lot. If you were my daughter, then I’d have to teach you about how to collect the blood. So I’d have to teach you how to put in a pad.”

“Can I see a pad?”

My mother laughed and said, “Sure.” She went to her bathroom and came out holding a large pad. “If I take off this paper, it’s sticky underneath and you put this side in your panty and it then stays there. If blood comes out of your vagina, it will land on the pad and get absorbed. All girls know about this. Now, as my pretend daughter, you know about it!”

“So moms and daughters can share pads?”

“Sure, and they also share all the knowledge and experience that goes with having to menstruate.”

“I can see that that is a special thing for moms and daughters. When I get panties, could I sometimes practice wearing a pad?”

“When mommy is having her period, I’ll give you a pad and you can have a pretend period at the same time that mommy is having a real one.”

“Thank you.” The only thing that had not yet been put away was my mom’s bras and I said, “Can I put your bras away?”

“Sure.”

I carefully picked them up and put them in the dresser drawer at the bottom of the pile of bras. “Why do you have less bras than panties?” I said.

“Women change their panties every day, but change their bras less often. I usually wear two bras a week.”

I spent some time gazing at the bras and thinking about how my mom wore these and that if I was her daughter, then I’d have to wear a bra also. The bras seemed to be as pretty as the panties were. If I were my mom’s daughter then I would know all about what panties I wanted to wear and what bras I wanted to put my breasts in. Having likes and dislikes about panties and bras would make me just the same as a real daughter

***

I accompanied my mom to the lingerie department of the local store and when we arrived she said, “This is kind of silly, but I have always had a little fantasy about taking my girl to shop for underwear. A very special kind of mother daughter occasion. So, it sort of feels like that today. What am I saying? I guess I’m saying thank you for wanting to experience these special times with your mom. Thank you for allowing yourself to play the role of my daughter!”

I gave my mom a hug and I had the feeling that she almost cried, she was so happy. We went through the panty section with my mom both allowing me to pick out panties as well as point me towards ones that she thought I ought to be interested in. When all was said and done we had selected nine panties that were of all kinds of colors including pale blue, pink, red, purple, orange and a light green. Some were cotton some were made of a silky material. Some of the panties had ribbons formed into little bows, some had lace and some had designs such as little red hearts.

When we were about to have the panties rung up for purchase, my mom turned to me and said, “I’d like to buy you some bras.”

It was kind of an odd moment, because it now seemed to me that my mom had seized control of this attempt we were making to fill in the void created by me not being her daughter. I may have started us on this path, but I could see that my mom was now saying that she wanted to take the lead. I don’t know if I had ever seriously envisioned anything more than getting underwear that was something other than white, but now I could see that I was going to have to accept all the consequences of the events I had put into motion. “Sure, mom,” I said. “I would like to wear a bra. Thank you.”

“What kind of bra do you want?”

That was a difficult question to answer since I knew very little about bras. “What do you mean, mommy?”

“Bras can be plain or pretty. They can be in all kinds of colors.”

“I think I’d like pretty bras.”

“They can even have some padding in them.”

“Padding?”

“Yes, to help girls pretend they have bigger breasts than they have.”

“I guess I should get padding, shouldn’t I?”

“Sure, so let’s look for pretty padded bras for you.”

We now went through the section devoted to training bras and A cup padded bras. The more we looked, the more I got into the search, until I was getting excited with each new bra that we came across. I began thinking about how nice it will be to wear a bra and hang out with my mom. My mom had many good suggestions as to which bras would be the best to buy and after some time we had selected five bras for me. When mom had paid for the panties and bras and we were walking to the car, she said, “The day a girl gets her first bra is often a very exciting day in her life. It shows how mature she’s become. It’s very exciting for a mother to be with her daughter at such an important moment. I must admit that bra shopping with you was as fulfilling for me as it ever could have been with a real daughter, and I’m truly thankful to you for being such a good sport about it.”

“I think I’m really going to enjoy wearing a bra, mommy. Together with panties I think I’ll sort of look like your little girl, your daughter and that makes me really happy.”

***

When we got home, I was anxious to try on a bra and panty for the first time. My mom said, “Before you put on a panty and bra, we have to have some rules.”

“Rules?”

“Yes. Rule number one is that you can only wear a bra and panty from after dinner on Friday, until Monday morning before you go to school. In other words, bras and panties and pretending we’re mom and daughter are only on the weekends!”

“So I wear my underpants during the week when I go to school?”

“Yes. The same as now.”

“What about if there is a holiday or during the summer?”

“I suppose you can pretend to be a girl on holidays and maybe the summer as well. We’ll probably have to revisit rule 1 in the future.”

“What is rule 2?”

“Rule number 2, is you only wear your bra and panty at home. When we go somewhere on the weekend, you have to dress as my son.”

“You don’t want anyone to know that I’m wearing a bra and panty?”

“Yes, of course. It will only require all kinds of explanations and blah, blah, blah that mommy doesn’t want to have to deal with. The main thing is that you and I know why we’re doing this. No one else has to know about it or give us their two cents. Got it?”

“Yes, mommy.”

“You agree to the rules?”

“Yes, mommy.”

“One other thing is that we should let your hair grow out longer, so we can fix it like a girl’s whenever we want to.”

“That would be nice.”

“Good. So what bra and panty do you want to wear for your first time?”

“Can I wear the pink bra and panty that we bought. The ones that are like yours.”

“Sure. Go ahead.”

One of my bras is a close approximation of the pink bra that my mom had been wearing the day I saw her in her bra. It was a similar shade of pink and had a bow and lace in the same places as my mom’s.

We were in my bedroom and I didn’t know if I was supposed to change by myself. “You can change in front of me,” my mom said. “On the weekend, you’re to be my daughter, and that means that we can get dressed together.”

I took off my boy clothes including my underwear. At first I didn’t know what to think of my mom seeing my little penis, but she didn’t say anything about it. I put on the pink panties that we had bought.

“So cute!” my mom said, almost giddy with laughter. “Now put on your pretty pink bra!”

I held the bra not knowing what to do with it. “Of course, I’ve got to teach my little girl how to put on her bra!” my mom said. “It’s her first time wearing a bra!”

My mom took the bra from me and then said, “I’ve got to film you putting on your first bra! It’s such a precious moment that I never want to forget!”

Mom set up her phone to record this special mommy daughter time that she wanted to preserve. While the camera rolled, mom helped me on with the bra, giving me careful instructions so that I’d be able to put on any of my bras from now on. When the bra was on me I preened in front of my mirror admiring myself in my bra and panty. The pink bra had some padding so I felt like I really was like a young girl who had some small breasts. It was interesting to feel like I was a girl for the first time. To think of myself as being my mom’s daughter gave me a good feeling, like I had done something really nice for my mom. She was beaming with happiness.

“My little girl’s first bra!” my mom said, teary eyed.

There was something magical about the experience. This birth of girlishness that so enchanted my mom, that so fed into a longing that she had had for so many years. But it was true that it also felt really cool to be wearing a bra and panty. It was particularly nice to be wearing pink underwear and not the boring old white underwear that I always had been wearing. It was nice to imagine that I was a girl and would have all the same experiences as my mom. We would no longer have the divide between us caused by me being a boy.

For the rest of that day, I wore a boy tee shirt over my bra and regular pants. I slept at night in my boy pajamas, though my mom said it was okay if I kept on my bra and panty if I wanted to. I did keep them on, partially with the thought that in the morning I’d sneak into my mom’s bedroom so that we could be together in our bras and panties. That was a moment that I had been hungering for since I believed it would be one that my mom would find wonderfully satisfying.

***

When I woke up the next morning I took off my pajamas and made a beeline for my mom’s bedroom. She was asleep, but I snuck under the covers and lay with my head leaning against her shoulder. She woke up and I said, “Good morning, mommy.”

“What are you … “ she started to say and then laughed. “I see. You’re being my little girl jumping into bed with her mommy.”

She sat up and held me. “And look who’s wearing her bra and panty,” she said. “I know what you want, you little rascal. You want to see mommy put on her bra and panty? Don’t you?”

It was true. I wanted to experience what a daughter might experience with her mother. “Okay, young lady.” My mom got up. She was wearing a nightie and she went into the bathroom to pee. “Come watch mommy, pee,” she said.

I went in the bathroom and she was sitting there. I could hear the sound of pee hitting the water in the bowl. “See how mommy sits down to pee? That’s what girls do. They never stand. Also, when we’re done peeing, we take some tissue paper and we clean ourselves up. If you’re going to be my little girl on the weekends, then this is the way you have to pee also.”

“Yes, mommy.”

“Good.” My mom got up and said, “Now I’m going to take a panty and bra from the drawer and put them on.”

I watched in fascination as she opened her dresser and fetched a white bra and panty. She took off her nightie so she was naked. I stared in wonder at the hairy triangle that formed at the top of her legs and at the large ponderous breasts that hung from her chest. My mom stepped into the panties and pulled them up to her waist and then she put on her bra. I was thrilled to watch as she captured each of her breasts into her bra, and then to realize how the cups were holding her breasts in place. “I wish I had breasts like you do, mommy.”

My mom looked at me and said, “You poor dear. I can imagine what you must be going through. Even some real girls are envious of girls that naturally have larger breasts, but it isn’t just breasts that defines a girl. There’s a lot of things about you that tell me that you truly are a girl and definitely my pretty daughter. For example, you have a cute, shapely body that is way more girl-like than boy-like. I guess I’m just trying to say to be happy with what you have and not be sad because of what you don’t have.”

“I’m sorry, mommy. I’m not sad. I’m very very happy that I can wear a bra, and that makes me feel close to you.” My mom gave me a big hug. Mommy and her daughter hugging each other wearing their bras and panties.

“Anyway, now you’ve seen how mommy puts on her bra and panty. She does it just like the way that you do. So now us girls should put on some tops and a skirt or pants and we should have our breakfast!”

I had never felt so close to my mom as I did watching her get dressed. It was everything I was hoping to feel. This intimate part of her life, that she could only share with a daughter, was now mine to be a part of, at least on the weekends.

***

On Monday morning I switched back to being my mom’s son. It wasn’t so hard to do, mainly because I knew that by the end of the week I could be her daughter again. I cherished the little space I created in my dresser for holding my panties and bras. Whenever I wanted help in remembering what it felt like to be my mom’s daughter, I opened the dresser and took out my panties and bras and admired them.

By Thursday my mom said to me, “Tomorrow after dinner you can be my daughter again if you want.”

“I do, mommy!”

“Good. Well, mommy was thinking that her daughter really needs to have some dresses. Putting on boys clothes on top of her panties and bra doesn’t make a lot of sense, unless you were a tomboy. Are you a tomboy?”

“What’s a tomboy?”

“A tomboy is a girl who is sort of tough and acts like a boy in some ways.”

“Oh, no, mom. I’m the opposite! I’m a boy who wants to act like your daughter!”

“Then you really need some dresses. I’ll be a little late coming home tonight because I’m going to stop off at a store and buy you some dresses to wear. That way, tomorrow after dinner you can put on your bra and panty and then a dress. Well, I guess I’ll also have to get you some shoes and socks. Maybe some tights, and a nightgown, as well.”

“Thank you so much, mommy. I can’t wait to see what you buy me!”

***

The dresses my mom brought home astonished me with their beauty. A glorious, frothy pink dress with a many layered built in crinoline and fancy bodice covered in lace and ribbons and short puffy sleeves. Also, blue and white dresses that also contained voluminous skirts. There were also a couple of skirts and blouses and mom had also found white shoes with a small heel and white tights. She also bought me a couple of filmy pink nighties with ribbons and bows on the shoulders and made of a very soft material. “You’re all set now, dear. Lots of options depending on your mood. I can’t tell you how much fun it was to pick out dresses for my little girl. I think every mother has fantasies of seeing her girl get dressed in pretty clothes and I’m so happy that you’re willing to play along with this fantasy of ours.”

I could hardly sleep waiting for Friday morning to come and then I was anxious all day long for dinner to come and be over. When it was, I washed up and put on a bra and panty again and then took the pink dress to my mom.

“You’re ready to put on your dress?”

“Yes, mommy.”

“I think I’m as excited to see you in the dress as you are! First put on your tights.” My mom showed me how to put on the tights and then she lowered the dress over my head and down to my shoulders and zipped it up the back.

“Oh, my lord,” she said. “I can’t believe how cute you are. So pretty, you’re a little angel!”

I ran to the mirror and looked at myself. It was true. I was enmeshed within the puffed-up skirts of the dress with the crinolines peeking out and the frou frou across my chest and the cute short sleeves. There was no way anyone would mistake me for a boy, except that my hair could use a few inches in length. “Yes, mommy, I feel through and through that I’m your daughter!”

“Come hug me!”

I ran into my mother’s arms and she gave me a long and passionate hug. “You are mommy’s little girl. Do you know that?”

“Yes, mommy.”

“Come sit down with me!”

I sat down with my mom, our skirts raised up over our crinolines. She put her arm across my back and held me. I said to her, “Mommy, tomorrow we should do a girl thing that you would have done with me if I had been your daughter.”

“What a nice idea! Let me think. One thing I’ve always wished I could have done with a daughter is make cookies.”

“Let’s make cookies, mom. Teach me!”

“Okay. That’s what we’ll do.”

When it was time for bed, my mom came into my bedroom with me and helped me take off my dress and tights. She fetched one of my pink nighties and she helped me on with it. I was still wearing my bra and panties and I felt wonderfully soft and a perfect daughter as my mom tucked me in, kissed me goodnight and turned off the light.

***

The next day started what would turn out to be a routine that my mom and me would reenact in numerous ways over the subsequent years. I’d dress as a girl, this day wearing a skirt and blouse, and then participate with my mom in something that mom’s and daughters do. This day we put on aprons and my mom showed me how to bake cookies. We had so much fun. I can’t remember being this happy. I loved having my mom’s full attention and getting to be close to her. I made a point of imitating her female movements, thoughts and emotions. Being dressed as her little girl and eventually getting long hair sealed the image in my own mind of a mom and her daughter. What we did together varied all the time. She taught me how to sew, how to knit. We even played some basketball, mom and daughter in cute little gym outfits she had bought for us. She gave me demonstrations of what nurses do and she discussed with me how I might want to become a doctor one day. She taught me all about make up. I even got to put polish on my finger and toenails on Friday afternoons and remove it on Monday mornings. When it was winter, and I’d always be wearing socks at school, mom let me keep the polish on my toenails all the time. For holidays and snow days and other occasions I could keep the fingernail polish on longer. My mom taught me about fashion and my wardrobe grew with time to encompass as many girl’s dresses and skirts and shoes as my mom had.

Now that I was my mom’s pretend daughter I got fully engaged in her wardrobe. She taught me everything I wanted to know about the clothes she wore. I learned that next to the bras in the dresser drawer were her girdles. I found them to be captivating and she allowed me to spend an afternoon engrossed in examining them while I lay on her bed. The intricate patterns of elastic and lace panels and garters and decorations were intriguing. I even asked my mom to put on one of the girdles so I could see what it looked like. She obliged and gave me a complete demonstration of how she stepped into it, pulled it up her legs to cover her rear end, clipped it and zipped it. Then she put on her stockings and attached them to the garters. It was a fascinating process and when she was done I asked her if I could wear one of her girdles and she said, “I have an all-in-one that is a trifle too small for me. Put that one on and see what you think.”

The all-in-one was white and I stepped into it and pulled it up to my hips and mom put the arm straps over my shoulders, and zipped up the side. It had bra cups big enough for my mom’s breasts so it was way too big for my small chest. Despite that, it wasn’t really too loose for me, though it wasn’t tight either. Wearing it made me feel very womanly, and I realized it made me feel like a smaller version of my mom. “I feel like a lady, wearing this!”

My mom laughed and said, “Now you’re my little lady. You’re so cute in that. I wish I had stockings in your size that you could wear. I’ll have to get some.”

I especially loved when my mom had her period. She would give me one of her large pads and I’d get to wear it in my panties for a few days. It made me feel close to her, like we were sharing a special girl thing together. I was very curious about her period and eventually I got my mom to talk to me about what she was experiencing. Girls get cramps and it can hurt. Sometimes girls have to rest at home because it makes them feel bad. I even got her to show me the pad in her panty with some blood on it, and then I put some ketchup on my pad. When my mom was doing the laundry she said, “I saw a bit of blood on your panties. How is that? Did you cut yourself?” When I confessed she both thought I was crazy and also endearing.

Initially my mom’s rules held fast and she applied them strictly. But after several months she had determined that once I was dressed up, I was indistinguishable from a real girl and so we would occasionally make an excursion together, but strictly to a larger town that was a distance away on the highway. At first we’d go see a movie together. Then we’d go out to dinner at a diner. A lot of fun was clothes shopping which we’d do at various distant malls. I especially liked the symbolism when my mom would take me into ladies restrooms and fitting rooms.

Once we ran into a nursing colleague of my mom’s and she introduced me as her daughter. “She’s so pretty,” my mom’s friend said causing me to blush. Later, my mom told me in the car that it was one of the happiest moments of her life to have a friend tell her she had a pretty daughter. All the pieces of her own fantasies of having a daughter had materialized one by one.

***

In the warm weather my mom and I often had picnics in the grass outside our house. We’d prepare an elaborate picnic basket and dress up in spring or summer dresses and walk out into the yard and spread a large blanket and then gracefully sit down in the sunshine. We were like two ladies in a French impressionist painting, elegantly dining with our pretty skirts arrayed around us. Yet again this was one of those occasions my mom had had little hope of ever experiencing, and now with her weekend daughter, she had the opportunity to live her dream. While we laid in the sun or in some shade on the hotter days, I’d get my mom to tell me about she and her friends growing up and what they did together. I had a voracious appetite for finding out about all the events and experiences that filled out my mom’s life as a young girl.

Because of all the land around our house, our neighbors were not right on top of us. Maddy Riggins, a widow about ten years older than my mom and her daughter Rosalee lived to one side of us. Maddy Riggins was a formidable, but kind woman. She reminded me of what pioneer women must have looked like. In her case, solid with an ample bust and fond of long skirts and long sleeve buttoned shirts. My mom and her were casual friends, occasionally having a cup of coffee with each other and talking about the neighborhood. Even though Rosalee was my age, I had not seen too much of her because she went to Catholic school and was not around very often to play. The few times Maddy and mom arranged for us to play were fun, but we had yet to discover a common interest that would draw us in to become close friends. On the other side of us were the Hogans who were an old farming couple with grown children. My mom and I knew them well enough to ask them for a favor, such as borrow some flour, or gladly do a favor for them, such as feed their chickens.

As it so happens, one Saturday afternoon that mom and I were picnicking and wearing our white dresses, Rosalee came by hoping to get an egg. The path from her house across the fields led to our backyard where she came upon mom and me.

Without missing a beat my mom said, “Hello, Rosalee. It’s so nice to see you. It’s been awhile.”

Rosalee stood next to the blanket looking at us. “Yes, I’m sorry that it has been.” Rosalee was staring at me and finally said, “Why are you wearing a pretty dress?”

“Because pretty dresses are nicer than ugly ones?”

Rosalee broke out into a gale of laughter, and said, “Why are you wearing a dress?”

I looked at my mom, not knowing what I should tell her, and my mom said, “Greg and I decided that it would be good for us if he were to pretend to be my daughter on the weekends.”

Rosalee made a puzzled face, and I added, “So we can experience all the special things of a mommy daughter relationship.”

“Oh, you mean as a boy you and your mom can’t experience what girls experience?”

“Exactly.”

“My uncle Pete wears dresses all the time, but they’re not as pretty as your dress.”

“How interesting. You’ll have to tell us about him. Would you like to join us for the picnic?” my mom said.

“Sure, I’d love to, but first, if it’s not inconvenient, my mom was hoping she could borrow an egg?”

“Sure. Greg, go inside and give Rosalee an egg. Come back and join our old-fashioned picnic where ladies dress up and lie on the lawn. Greg can loan you one of his dresses. Do you mind, Greg? I think the two of you are about the same size.”

“No, I don’t mind. That would be a lot of fun to have Rosalee join us!”

I fetched Rosalee an egg and she ran off home. Rosalee came back fifteen minutes later and I took her into my bedroom to show her my dresses.

“Here are my dresses,” I said, opening up my closet and pointing to them.

I was wearing my white dress and Rosalee held the pink dress up to herself and looked in the mirror. “Do you like being a girl?” Rosalee said.

“I do. It’s fun to be my mom’s daughter. We get to do so many nice things that moms and their daughters can do.”

Now Rosalee held up the blue dress and looked at herself in the mirror. “I think it’s sweet, Greg that you’re willing to do that. Which dress do you think looks better on me? The pink or the blue?”

“The pink dress is my favorite,” I said.

“Then I should wear the blue one.”

“No. It’s okay if you want to wear the pink one. I really don’t mind.”

“I prefer blue, actually, but I’d love to see you in the pink dress,” Rosalee said.

“I can put it on now,” I said, as I reached behind my back and unzipped my white dress and lifted it off over my head.

“What a pretty bra and panty you’re wearing,” Rosalee said.

“Thank you. I had so much fun with my mom when we went bra and panty shopping.”

“My mom took me to buy my first bra a couple of months ago,” Rosalee said. “I enjoyed it, but I think my mom enjoyed it even more than I did.”

“Does wearing a bra make you feel more grown up?” I said.

“Sure, but I also was feeling grown up because I began to notice a little growth in my breasts. Breast buds began to form and my mom noticed it one day and said it was time for me to get my first bra.”

Rosalee took off her top and shorts so she was wearing her panties and bra like I was. Her bra was white and pretty and revealed that she had some small breasts. Rosalee lifted up her bra showing me her breast buds. “See how my nipples are getting bigger and longer. I think that’s the very first thing that starts to change in a girl.” I looked at Rosalee’s naked breasts and admired how pretty they were, but also felt a bit envious of her.

“My mom and I decided that I should get padded bras, otherwise I wouldn’t be able to show anybody that I had breasts.”

“My Uncle Pete wears bras where he can put in a whole breast made out of silicone. They’re really neat because he ends up looking as big as my mom.”

“Really? I’ll have to talk to my mom about that.”

“They’re also neat because that way you can have any size breasts you want. I can only have the size that I eventually grow into. Probably like my mom, so I guess I’ll probably end up with a D cup bra. All the girls in my family usually have D cup breasts.”

“You know, as much as I’ve looked at my mom’s bras, I never looked to see what size they are.”

I put my pink dress on and Rosalee put the blue dress on. Rosalee was carrying a small purse and she took out some lipstick and said, “Let me put some lipstick on you!”

“I’ve never worn lipstick.”

“You’ll love it!”

“Sure, go ahead!”

Rosalee put bright red lipstick on my lips and then did the same to herself. We looked at each other and laughed. I went to look at myself in the mirror. Lipstick was definitely going to be something that I’d want to get to know better. “I love the lipstick. Now I’m a real lady!”

“It’s so much fun to play dressups,” Rosalee said. “I have a lot of flower girl dresses at home because we have a big family and I’ve been to a lot of weddings. I’m sure many of them would fit you. We could have a fancy tea party and play different ladies in different dresses.”

“That sounds like fun. Let’s show my mom how pretty we are!”

We went outside and joined my mom on the blanket. “What? Are you both wearing lipstick?” my mom said laughing. “And you’ve changed to your favorite pink dress! Come here, both of you,” my mom said. We sat next to her on either side. Our skirts and crinolines in pink and blue puffed up over her lap from either side and she hugged us both together. “Such pretty girls, my, my, my,” she said.

“Mom, I was wondering what size bra you wear?”

“I’m a 36D, why do you ask?”

“Rosalee said that her mom is a D cup also and she’s probably going to end up being a D cup too. Did you know that Rosalee got her first bra a couple of months ago?”

“I didn’t know that. Congratulations, Rosalee, you’re growing up!”

“Thank you. This picnic is so much fun!”

“Let’s have some of our delicacies,” my mom said, and she opened up the picnic basket we had packed earlier. In it was some hummus and pita bread, some tuna sandwiches, and various crudities and cheese. A pitcher of lemonade was on the blanket together with glasses.

The three “ladies” wiled away the hours chatting and otherwise enjoying each other’s company. At one point, I said, “This is so nice because we’re three girls. If I was a boy we couldn’t have had such a nice time together.”

“There is a degree of truth to that,” my mom said. “We spent so much time talking about girl’s things that a boy would probably find boring.”

Before it was time for Rosalee to go home, we made plans to see each other again. “You’re welcome here any time,” my mom said.

“And I want Greg to come visit me, too.

***

The next weekend my mom got a call from Maddy Riggins. “Rosalee has been going on and on about what a wonderful time she had at your house last weekend. She said you had a fancy picnic in the backyard?”

“Yes, we did have fun. It’s something that Greg and I love to do and we were thrilled that Rosalee could join us.”

“Rosalee said that she borrowed one of Greg’s dresses?”

“Yes. They seem to be the same size.”

“I think it’s so adorable that Greg is comfortable presenting as a girl and that you’ve helped him along.”

“Yes, Greg and I came to an understanding that only by being mother and daughter could we get as close emotionally as we wanted to. So, it’s been the most wonderful thing for me, to have the daughter that I’ve always wished I had had. And luckily, Greg seems to thrive being a girl.”

“The reason I’m calling is to see if both you and Greg would like to join Rosalee and myself tonight for a spaghetti and meatball dinner and a movie?”

“That would be wonderful!”

“And please have Greg wear any clothes he wants to. A dress is fine with us.”

***

My mom and I walked over to Rosalee’s house for dinner. Both my mom and I wore blouses and skirts. When we got there, Mrs. Riggins invited us to sit in the living room and have some hors d'oeuvres. “I see that Greg is wearing a very pretty skirt and blouse,” Maddy said.

“Thank you,” I said. “The skirt is one of my favorites.”

“Rosalee came home last week so excited about the lovely picnic you had. She especially loved that you all like to dress up for it and that she could wear one of Greg’s pretty dresses.”

“Having Rosalee around is a delight,” my mom said.

“Playing dressups has always been one of Rosalee’s favorite games, hasn’t it dear?” Mrs. Riggins said.

“Yes, mom. I was telling Greg last week that we could play with my flower girl dresses. Have a really nice tea party.”

“By all means. Greg is welcome anytime.”

“I was intrigued by your brother Pete? Rosalee mentioned that, like Greg, he wears dresses?” my mom said.

“Yes. My brother Pete wanted to wear dresses as long as I can remember. He’s a year and a half younger than me, and he used to help himself to my dresses starting when I was about fourteen and he was twelve. He loved make up and really everything feminine in our household, though he didn’t see himself as being a girl. He liked doing everything that girls do, but did not want to become one. He once told me that while it would be nice in some ways to magically become a girl, he preferred staying a boy, because it allowed him to enjoy pretending to be a girl. You see, if he was a girl, he’d be like all girls who don’t usually think about how wonderful it is to be a girl. His delight and appreciation of feminine things comes about because he’s a boy.”

“I can understand that,” my mom said.

“Initially, I was the only one who knew, but later when it came out in high school that he liked wearing dresses and pretending he was a girl, my parents were pretty upset and his older brothers were really mean to him. I defended him every way I could and so we grew to be very close. He was a doll when my husband, Rosalee’s dad, took sick and passed away a few years ago.”

“What does Uncle Pete do for a living?”

“He owns a bridal shop. It’s very funny because he gets to be surrounded by pretty dresses all day long and gets to help ladies pick out their dresses. He’s very successful because he has always had a good eye for fashion.”

“Can I ask a personal question? Is Uncle Pete married?”

“No, he never settled down with anyone. The problem he faced was that he always had to be a boy when he met girls, but then he’d have to admit his desire to dress like them. The few women he got that far with, weren’t very accommodating.”

“That’s too bad.”

“Nonetheless, Uncle Pete is one of the happiest people I know. Next time he comes by we’ll all get together.”

“We’ll look forward to that.”

I had listened to Mrs. Riggins description of Uncle Pete and it made me wonder if I would ever find happiness with a woman. Of course, unlike Uncle Pete, I already had Rosalee as a friend who loved the fact that I liked to be a girl.

“Greg has been my daughter on the weekends. During the week he’s been living his normal life as my son.”

“Is it hard to be both a girl and a boy?” Mrs. Riggins asked Greg.

“A little bit. I love being a girl so much that being a boy feels a little funny, mainly because I sometimes forget that I’m supposed to be a boy. Sitting in class I occasionally feel like I’m wearing a bra, but then I realize that I’m not. Also, when I look at the girls in my class, I wish I could be friends with them and play with them instead of the boys. I also like to look at what dresses and skirts their wearing and what shoes and I also like to observe how they fix their hair.”

My mom said, “I had no idea that it was so difficult for you, Greg.”

“It’s okay, mom. As long as I know that Friday is coming, I feel fine.”

“Would you like to wear dresses all the time, like Rosalee’s Uncle Pete?” my mom said.

“I’d like to be your daughter all the time, so I guess, so yeah, it would be nice if I could wear a dress every day. That’s what I’d want.”

I went off to play with Rosalee in her room while my mom helped Mrs. Riggins get the dinner ready. When we were alone together, Rosalee said, “I hope you get to meet Uncle Pete. He’s where my mom gets me my flower girl dresses and also her bridesmaid dresses. He could probably help you get some really pretty dresses, too. While I love all my dresses, it’s funny how every time I get a new dress I feel so excited.”

“I’m the same way,” I said. “I even get excited when I get a new bra or panty.”

“Me too. I guess some girls are just like that!”

“After hearing about your Uncle Pete, I was thinking how nice it is that you don’t mind if I wear dresses.”

Rosalee came over and put her arm across my back and held me. “I’ve never really felt comfortable playing with boys until the picnic last week. Having you wear a dress and pretend to be a girl is exactly what I need in a boy. You’re even more fun than playing with other girls, because you’re so excited about getting to be a girl. It’s contagious and makes me feel really feminine in a way that I enjoy.”

“I think playing with you is the most fun I’ve ever had,” Greg said.

“Let’s surprise our mom’s by dressing up fancy for dinner tonight,” Rosalee said. She opened up her closet to reveal her collection of flower girl dresses. “See my dresses, Greg. Which one do you want to wear?”

“Ohmygosh,” I said. “How can one even choose. They’re all so pretty!”

Rosalee took down one of the dresses. “I’m going to wear this one tonight.” It was blushing pink in color, floor-length, sleeveless with a scoop neck, tulle with cascading ruffles and lace.

“Wow, that’s so elegant,” I said.

“You should wear this one,” Rosalee said and handed me a pearl pink gown with a long A-line skirt with a translucent tulle overlay gathered at the waist and adorned with beadings and sequins.

“Yes, that one is very pretty!” I said.

We took off our clothes and put on our dresses. Then Rosalee helped me with some makeup including lipstick and a couple of drops of perfume. It was fun to sit at the vanity and have Rosalee apply makeup to my face. While my mom had showed me how to do it, I did not feel confident in applying it. I certainly had not yet acquired Rosalee’s ability. When she was done with my face, I watched as she did her face.

When Maddy called out that dinner was ready, we came waltzing into the dining room as two femme fatales, to peals of laughter from our moms. “Such pretty ladies!” Maddy said.

“Gorgeous, and who applied your makeup so professionally?” my mom asked.

“It was Rosalee. She’s very skillful with the makeup.”

“The dresses look so perfect on the two of you,” my mom said.

“And here are some aprons,” Maddy said. “You girls cannot eat spaghetti and meatballs without wearing aprons. Those dresses are too pretty to get sprinkled with tomato sauce.”

Maddy handed me a pretty pink apron edged with lace and a similar one to Rosalee and we put them on. We sat at the table and Maddy brought out a large platter of meatballs and spaghetti. I could tell that my mom and Maddy were really enjoying being together and I felt happy that Rosalee and I had played a part in making that happen.

When dinner was over we all helped clean up the dishes and kitchen. In the darkened living room we gathered together facing the television to watch a movie. My mom and Maddy sat side by side on one end of the long sofa and Rosalee and I sat on the other end. Somewhere in the middle of the movie I noticed that my mom and Maddy were holding hands. I took Rosalee’s hand and held it and she snuggled a bit closer to me. Later in the movie I noticed that my mom’s head was leaning on Maddy’s shoulder and that both of her hands were holding Maddy’s hand.

When my mom and I were walking home that night, I asked her if she liked Maddy. “Yes, she’s a very sweet and kind woman.”

“That’s why you held hands with her?”

My mom turned around to look at me and said, “I think Maddy and I are discovering that we have a growing affection for each other. Girls can feel that with other girls, just the same way boys and girls can feel that together. After all, you and Rosalee seem like you’re two girls who are developing a real fondness for each other.”

“I think it’s very nice for you and Mrs. Riggins to be close friends.”

“That’s sweet of you to say. I’m hopeful that Maddy and I will become very close friends. She’s an amazing woman.”

***

Rosalee and I grew to be best friends. We loved playing together on long afternoons, both indoors and outdoors. We hiked together and played with dolls together. We talked endlessly. We read the same novels, usually about girls who had done something heroic or had worked hard and become successful. Oftentimes the girls in our novels had had to overcome the annoying prejudices of entrenched male-dominated institutions. Often I was dressed in a play outfit when Rosalee came over consisting of a jumper or a skirt and pullover top. Sometimes Rosalee and I were in the mood to pretend that we were princesses or noble ladies and then we’d each put on one of my fancy dresses, or, if we were at her house we’d put on her flower girl dresses. Once we were in our dresses and had on our fancy shoes, we’d make up a fantasy. In one of our favorite fantasies, we would pretend to be attending a grand ball in a castle in which Rosalee was a beautiful princess and I was a handsome prince who liked to wear lady's dresses. Our play acting also included scenarios in which Rosalee would be pretending to have a baby and I’d be the nurse helping her to deliver it. We grew quite close to each other, and even began to have occasional sleepovers. We’d sleep in the same bed as two girls. I’d be pretending to be a girl with Rosalee enjoying the fact that I was a boy pretending to be a girl. Neither Maddy nor my mom objected to the arrangement, which was testimony to how convincing a girl I had become.

At Rosalee’s house our favorite game was Catholic school class. She’d allow me to dress up in her school uniform and Rosalee would take the role of a nun and give me “lessons” on all kinds of subjects. She made me sit up straight, keep myself neat and not talk out of turn. In our game, I would do something “bad” and she would discipline me. Send me to the corner, make me write on the blackboard phrases like “I will never again be a bad girl!” or even pretend to hit my bottom with a ping pong paddle. This always led to screams of laughter.

Another favorite game was putting makeup on each other and doing our nails. More often, I’d put polish on Rosalee’s finger and toenails, pretending I was giving her a maxi-pedi. Our dolls had many tea parties in which Rosalee and I joined the dolls and we’d pretend to bake crumpets in a toy oven. Rosalee owned a couple of tutus and we used them to play a ballerina game in which we danced to Swan Lake playing on her stereo. We’d flutter about up on the balls of our feet and flap our arms as if they were wings. It was nice to feel that extra degree of femininity that came from being surrounded by the pretty skirts of a tutu.

Rosalee had a collection of miniature glass animals that I adored looking at. Little elephants, lions and many other creatures. Each one created out of colored glass. She had a charm bracelet and after telling my mom how much I loved it, my mom bought me one of my own and I always kept it on my wrist. Among the charms was a miniature iron, a comb and a ladle.

In parallel with my growing love for Rosalee, my mom and Maddy became lovers. I know this because on our movie nights now, it wouldn’t be long into the movie when I could see my mom rest her head on Maddy’s shoulder and then Maddy would put her arm across the back of my mom and then kiss her. The two of them could kiss for long periods. Sometimes I’d see Maddy put her hand in my mom’s blouse and feel her breasts. My mom would be doing the same to Maddy and though I couldn’t quite see it, I had the feeling that they each slipped their hands inside the waists of their pants or skirt where their private parts were. A lot of what they might have been doing I never really saw because I did care about the movies I was watching and I’d end up paying more attention to the film than what my mom was up to.

A nice development from my mom and Maddy falling in love, was that when Rosalee and I were going to have a sleep over, then the two of them would also sleep over. So all four of us girls would be together and it made for a fun and cozy night for all of us. Sometimes in the morning, when Rosalee and I had awakened early, we’d sneak into my mom’s or Maddy’s bedroom and then climb into bed with them. Rosalee and I loved being sandwiched between the two women and my mom and Maddy would press inwards squeezing us until we were crying with laughter.

***

When Rosalee and I were twelve, the effects of puberty were beginning to show. Rosalee now had breasts that had surpassed an A cup bra and were well on their way to B cup. One time when I was changing into a dress at Rosalee’s house she noticed the pad in my panties. “You’re having a period?” she asked me.

“Yes. I have a pretend period when my mom has her period. That way we both have our periods at the same time.”

“That’s so sweet, Greg. I’m having my period now also, and so is my mom. I did hear that girls that see a lot of each other tend to get periods at the same time.”

“That could explain why we all have our periods now. I looked at Rosalee’s panties and said, “How come you don’t use a pad during your period?”

“I’m using a tampon.”

“A tampon? What is that? My mom never mentioned tampons to me.”

“It’s just a little cottony cylinder that girls put in their vaginas to catch the blood.”

“Wow, that sound’s cool. I wonder why my mom hasn’t mentioned it to me.”

“Some girls don’t like them, or your mom maybe uses both them and pads. I have to change my tampon so I can show you what that’s all about, if you want. There’ll be some blood.”

“I don’t mind. I think it’s pretty neat. My mom showed me the blood in her pad. So I put some ketchup in my pad so I could pretend that I was bleeding. My mom thought I was crazy.”

Rosalee laughed and said, “She’s right! Having a period is not one of a girl’s most favorite things!”

Greg followed Rosalee into the bathroom and watched as she lowered her panties. “See this little string coming out of my vagina. If I pull on it, the tampon will come out.”

Rosalee pulled on it and the tampon came out dangling by the string. It was red from her blood and Greg said, “My dear Rosalee’s blood!”

Rosalee laughed and wrapped the tampon in a tissue and put it in the trash. Then she got a new one and showed Greg how she put it in by inserting the tube and then pushing it down into herself and taking out the tube.

“You’re such an expert,” Greg said.

“I’ve had a few months of practice already!”

When we left the bathroom Rosalee said, “I’m curious how you can fit a big pad in your panties.”

“What do you mean?”

“Don’t you have a penis in there?”

I laughed, and said, “Of course, I do.”

“It doesn’t get in the way of the pad?”

“I haven’t thought about that. Do you want to take a look?” I wasn’t totally sure that Rosalee had ever seen my penis. We had changed in front of each other, but if she had glanced at my penis I wasn’t aware of that. Of course, I had glanced at her vagina from time to time so if I was honest with myself I’d have to guess that Rosalee had also checked out my penis. But now, over the last month or two, I was beginning to feel sensation in my penis and I noticed that I was getting the beginnings of boners and pubic hair.

“Yes. I’d like to see it. I’m curious how you can fit a pad together with your penis,” Rosalee said. She seemed to be blushing a bit.

“Okay, I’ll show you,” I said. I lifted up my skirt with one hand and lowered my panties with the other revealing the large pad and my penis.

Rosalee regarded the view with interest. “I think your penis has gotten bigger than I remember it.”

“I guess it is sort of growing now.”

“You’ve got some pubic hair, just like you saw that I do.”

I pulled my panties back up and could feel that my penis did seem to be a bit crowded by the pad. Rosalee and I looked at each other in a way which seemed to be new. Like we were both beginning to realize that there was another element of connection that was creeping into our friendship that had to do with our reaching puberty.

***

As Rosalee had predicted, by the time she was thirteen, she grew to be a 36D cup, and along the way my mom agreed to buy me D cup bras and find me some nice breast forms to fill them. So Rosalee and I became two princesses with D cup breasts by the time we were 13. Along with Rosalee’s full flowering of her womanly maturity, her feelings for me burst forth between us one day so as to precipitate a permanent change in our relationship. We were playing one of our dressup games in which Rosalee was a princess and I was a dress-wearing prince. We were doing a pretend waltz when Rosalee impulsively kissed me on the lips. And then we clutched each other and lay down on the bed, entwined with our skirts puffed up against each other. We kissed and kissed. It was a release from our pent-up emotions that had been wanting to be liberated for some time now. The simple fact was that while we had been in love with each other for many months, our love had now developed a sexual component borne out of our puberty. Now I loved Rosalee as my girlfriend and Rosalee loved me as her boyfriend, albeit a boyfriend who preferred to dress and comport himself as if he were a girl.

Rosalee and I loved kissing each other and we added a kissing component to many of our games. For example, our tea party might include kisses when the hostess, either Rosalee or me, entered with a new pot of tea. We also invented new games in which we could kiss. A favorite was a girl wrestling match, where we would strip down to our bras and panties and pretend we were lady wrestlers. We grabbed each other doing made up wrestling moves with neither of us stronger than the other. Sometimes Rosalee had me pinned down and sometimes I pinned her down. The fun was in holding each other tight and kissing.

Thirteen-year old’s feelings of love and grown-up’s feelings of love are not exactly the same. One difference is that Rosalee and I were incapable of thinking about the future. All we knew was that we loved dressing up in our prettiest clothes and then kissing and hugging each other. As our physical affection for each other grew, our curiosity about each other’s bodies grew with it, until one day, Rosalee said to me, “I want you to play with my breasts. I want you to caress them and suck on them. How about we play a game in which you’re my baby girl and I feed you?”

“That definitely sounds like a fun game,” I said, and with Rosalee sitting on the couch, I lay down with my head in her lap. This was the same position I had countless times been with my mom and, in fact, still did occasionally with her when it was late and I was very sleepy. Of course, at thirteen I was more than aware of the significance of my mom’s large breasts hovering above my face and I had a whole new appreciation for when she leaned over and I felt them on my cheek. Since I was invariably wearing a dress or a nightie and had on my own D cup bras when I was in this position, I think this distracted my mom somewhat from the realization that I was ultimately a pubescent boy whose body was a coursing superhighway of hormones. I, for my part, took my pleasure discreetly, so as not to spook my mom. But now, Rosalee offered me the same joy but with someone with whom I didn’t have to be inhibited. In fact, it was her suggestion that I be more than passive. Rather, I should develop an interest in playing withher breasts, an activity that I can admit was no inconvenience to me at all.

With my head in Rosalee’s lap, she pretended that she was my mom and it was time to feed her baby. She reached behind her back and unzipped the top of her dress and then pulled it forward off of her arms to reveal her bra underneath. She lifted up her bra freeing her now D cup perfectly formed breasts and said, “You’ve been such a patient baby. Now mommy has some milk for you.”

She leaned forward guiding one of her nipples into my mouth which I began to suck gently while she said, “What a good baby. Such a hungry baby!” While I sucked she cradled my face in her arms and gave me a kiss on the forehead and gently ran her fingers through my hair. Having boners was new to me, so I didn’t quite understand the riot of feelings that seemed to be going on in and around my penis. I laid one of my hands over the top of my dress and felt that indeed my penis seemed to have swelled and was poking up in my panties. It was a little scary that maybe something was happening with my body that I didn’t know how to control or understand. But the feelings were pleasurable for the most part and I felt some pressure to just let everything develop whatever way it wanted to.

I must have sucked on Rosalee’s breasts for an hour, with her switching my lips from one nipple to the other about every ten minutes. While I sucked on her breast, she picked up one of the books that we had wanted to read and read it to me out loud. It was a story about a princess looking for the perfect dress and not being able to find it until she happened to meet a poor seamstress who sewed her a lovely gown. Ocassionally Rosalee stopped reading and said, “Such a wonderful baby,” and then gently removed my head from one of her breasts and moved it to her other breast. When the story was over, Rosalee inserted her finger over my lips, withdrew her nipple and said, “I’m sure the baby is full. Do you need to be burped?” I laughed and Rosalee moved her bra back down to contain her breasts again. Then she put her arms back in the top of her dress and reached behind herself to zip it back up. “That was so dreamy,” Rosalee said, with a calm and restful voice. “Would you like mommy to feed you again sometime, pretty baby?”

I smiled and nodded my head. Would I ever!

***

A week later we had another opportunity to play our mommy baby game. I had settled into sucking on one of Rosalee’s breasts when I felt her hand on my lap. Rosalee said, “I wonder what’s going on in the baby’s panties? She’s not wet is she?” Using her hand Rosalee pulled up the skirt of my dress until her hand was resting on my thigh. Then she slid it up my leg until she encountered the elastic leg band of my panty. One or two fingers felt inside my panty and she said, “I can’t tell if my baby is wet.” She removed her fingers and moved them up to the elastic waist band and I felt her entire hand slip down into my panty arriving at the top side of my penis. I felt a slight pain as my penis stiffened. It was all so new to me and my penis that we didn’t know what exactly was happening. Then Rosalee’s fingers slipped around the hardening shaft to the soft, hot skin near the tip and I felt an extreme jolt of pleasure. “What’s this in the baby’s diaper?” Rosalee said, laughing. I was well beyond the point of making coherent sounds and my mind was riveted on every nuance of what Rosalee’s fingers were doing. Every tiny motion was arriving in my mind as extraordinary pleasure. I passionately sucked on Rosalee’s breast and then she changed the breast and I resumed sucking on the new one. Rosalee once again began moving her hand on my penis and she said, “I love you, Greg. I’m sure that I’ll always love you. I’ll always love my baby girl.” With those words my penis convulsed in its very first orgasm. Rosalee laughed uproariously feeling my effluent come out in a few pulses onto her hand. “Now the baby does have a wet diaper!”

“I love you, Rosalee,” I said. She leaned in and smothered me with her chest the same way my mom had done when she leaned over.

I sat up and we looked in each other’s eyes. We didn’t have to say it in words because we both now understood how our relationship was going to be. We would be exploring each other’s bodies, we would be learning to do whatever we could to give pleasure to each other. It didn’t matter that my voice was going to change, that I’d start to have to shave, that I’d develop a man’s penis and boners that were adult sized. I’d still be wearing panties and a bra, I’d still find the prettiest dresses I could wear. I’d still keep my hair long and secretly paint my toenails during the winter months. Rosalee would continue to prefer me like this. She even told me that if I ever decided to not wear dresses anymore she’d have to break up with me. I promised her that I would never want to give up being the girl she wanted me to be.

***

As I entered puberty, I became less and less the cute little feminine boy that my mom and I could easily pass off as her daughter. Now I was becoming more and more clearly an adolescent teenage boy who dressed like a girl. My mom became worried that I’d be upset about the changes that were happening, but I told her not to worry. “As long as you continue to see me as being you daughter, then I’ll be happy. Rosalee has already said that she’s perfectly content with the changes to my body. Though she insists that I had better continue to wear dresses.”

***

From this point forward, I lived a double life. At home with my mom on the weekends, or later in the present day with my wife Rosalee, I continue to wear pretty dresses and bask in my feminine persona. During the week I lead a life in the working world as a man. My mom and I never tired of enjoying the special bond that is shared by moms and their daughters. Even down to her last days at the end of her long life, I cared for her the way daughters do. In fact, the last thing we ever did together was watch the video of me putting on my first bra so many years earlier. It was among the happiest things that had ever happened to both my mom and me.

The End