Love Fest

By

Pamela

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Author’s note: This story is based on the unproven hypothesis that a desire for cross-dressing may originate in a young boy’s subconscious longing to be emotionally close to his mother. He dresses like a girl so – in his own mind – he can establish a common bond with his mother. A female-to-female intimacy that distinguishes this relationship from that of his mom and dad. I have no idea if this “theory” of cross-dressing is hogwash or not, though I do think it’s somewhat relevant to my own life. My dad and older brother were handsome alpha males while I was clearly a beta who was close to his mom. At thirteen I realized that cross dressing – starting out in her clothes – was the greatest thing since sliced bread. Was the origin of that impulse tied to a desire to be closer to my mother?

The following story – which is entirely fictional – includes incest between a mother and her twelve-year-old son in order to amplify the psychological theory proposed above. Can a boy develop a desire to cross-dress as he unconsciously seeks ways of being emotionally closer to his mom? The crackling emotional power contained in the idea of physical relations with one’s mother is meant to inject energy into the story. I leave it to the reader as to whether this mechanism is effective or not. Everyone is different.

To those of you who have no stomach for a fantasy about incest please don’t read this story. Alternatively, the words ‘mom’ and ‘mother’ and ‘wife’ can be edited in such a way as to remove the obvious references to incest. This will not change the impropriety of an older woman having sexual concourse with a minor. The events depicted in this story never happened in the real world. My mother never had knowledge of my cross-dressing and we never had a conversation involving sex or women’s clothing. It certainly would have been pretty interesting if we had ever done so.

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“What’s the matter with Pete?” Mr. Bill Marchand said to his wife Helen. Pete is their youngest son, now twelve. Chuck is his fourteen-year-old brother.

“What do you mean?” Helen said.

“You know. I’ve pointed it out many times in the past. Pete can’t dribble a basketball without looking at it. His baseball skills are pathetic. He can’t throw a football worth shit. He hates camping.” Bill laughed. “He struggles with ten-pound barbells. Can barely get them over his head. His skinny arms flail around. I don’t think he even has a bicep.”

“That’s not a kind way to view your son.”

“I know, I know, but I’m worried about his future. He has to learn to assert himself physically. Be a presence instead of an almost invisible afterthought among a group of guys.”

“Some boys aren’t talented athletes.”

“There’s ‘not talented’ and then there’s ‘pathetic.’ I’m afraid that Pete is pathetic.”

“His body is obviously not designed for sports. His bones, his frame. Everything about him is softer, gentler …”

“Nonsense. He has functioning boy equipment. He has testosterone. If he exercised rigorously muscles would pop up on him overnight. There’s no limit to how strong he could become if he just applied himself.”

“But he doesn’t want to, does he? He likes himself the way he is.”

“It’s true he doesn’t complain about not being selected to play sports.”

“You’re the one who complains. You forced him onto a little league team. What a disaster! They put him in the outfield, he missed a fly ball, and he began to cry. The coach had to yank him from the game.”

“That was embarrassing,” Bill said.

“For you perhaps, but much worse for poor Pete.”

“So this leads me back to my question. What’s the matter with Pete?”

“What’s the matter is your trying to fit a square peg in a round hole.”

“Putting a boy into a boy hole should not be hard. I’m dreading the camping trip with him and Chuck. Pete is useless. His backpack can hold practically nothing. He can’t erect a tent. I don’t think he can hike a mile. Campfire stories scare him.”

“Look Bill. Let me handle it. Don’t force him to go camping. I’ll work with Pete and try to learn how he sees the world around him and his future. Okay? That relieves you of the burden of apologizing for your perception of him as a failure.”

“Okay. I think that’s a good idea Helen. I’ll focus on Chuck; you focus on Pete. Chuck and I will have a fantastic time camping together. You can spend a week bonding with Pete and figuring out what makes him tick. When I get back we can see where to go from there.”

***

As relatively young mothers go, Helen was a kind and warm spirit. She had loved nurturing her two sons from infancy until they had begun the natural process of finding their independence. She had liked being a mother but also liked the job that she had acquired once the boys were in full-time school. She was the co-owner of a dress shop that catered to classic feminine styles. For years she had been a customer preferring the pretty dresses they sold over jeans and more fashionable dresses. When she was looking for work, the owner invited her to buy in and she and Bill made the investment.

The dress shop provided Helen with the opportunity to acquire the kinds of feminine dresses she preferred. It had been her idea to add sections for lingerie and shoes so that it could be a one-stop shop for women and girls looking to buy an entire outfit.

Despite his disdain for athletics, Pete was for the most part a reasonably well-adjusted kid. At least that’s the perception of his parents. Apart from athletics he did well in school and had always had at least one best buddy to hang out with. The other kids toned down their mockery of his miserable sports IQ in deference to Chuck. Chuck’s renown as one of the really neat cool kids enabled his younger brother to get a pass.

Pete watched as his mom and dad kissed each other goodbye on the front steps while Chuck finished loading up the car. His parents whispered ‘I love you’ to each other and then Pete’s dad gave him a hug goodbye and went to the car. Helen and Pete waved goodbye to Bill and Chuck from the front steps of the house as father and son set off on their camping adventure.

Helen and Pete went back inside and sat at the kitchen table. Helen poured herself a cup of coffee and made a hot chocolate for Pete.

“Why did dad decide that I didn’t have to go? He’s been telling me that I had to shape up and learn to camp for months now.”

“Your father and I had a little talk in which we realized that his insistence that you learn how to camp is a fool’s errand – at least for now. He’ll want to revisit that in the future.”

“Fool’s errand?”

“That means that it can’t be done, so it’s pointless to devote one’s time to making it happen.”

“Dad’s upset with me,” Pete said with a worried frown.

Helen was not good at lying. “Upset is too strong a word. Your dad has strong ideas about boys and how they’re supposed to be. He wants and expects you to make an effort to be that kind of boy. Since you haven’t made that effort he’s disappointed.”

Pete fought off tears. “I don’t know how to be the kind of boy he wants me to be! I try to catch a baseball but I just can’t. I try to throw one and he makes a face. He told me he knows girls who can throw it further than me.”

Tears came down Pete’s cheek, and his mother held him close to her. “My poor dear. Men can be harsh and mean sometimes.”

When he could speak again Pete said, “Sometimes when dad is mean to me he tells me not to tell you.”

Helen’s face filled with worry. “What has he done?”

“He’ll kill me if I tell you.”

“No he won’t. I won’t let him. Tell me.”

“A couple of weeks ago he told me to lift the ten-pound barbells. One in each hand. I got them up to my side but as hard as I tried I couldn’t get them over my head. He yelled at me and called me a ‘Pussy’ and a ‘Sissy.’ I was crying and he didn’t care. He told me to put the weights down and not tell you what he called me.”

“’Pussy’ and ‘Sissy’? I’m glad you told me. Your father is going to hear from me!”

“Won’t he be mad at me for tattling?”

“Telling you not to tell me was wrong. Your father fancies himself a real man because he can throw a ball. Apparently real men are afraid of being caught at bullying because they know it’s wrong.”

“What does dad mean that I’m a ‘Pussy’ and a ‘Sissy’?”

“Dad’s saying that you’re a boy who acts like a girl. Unfortunately, your dad reverts to sexism when he’s not thinking.”

“It’s terrible what he says about me, right?”

“It’s terrible that he says that. It’s not terrible that you act like a girl if that’s the way you want to be.”

“Then why does Dad think it’s bad?”

“Because for him everyone born with a penis is supposed to be like him. He preaches to everyone how he believes in freedom – but he only means freedom to be like him. His son is not free to be different from him!”

“I don’t like sports but even if I did I don’t think I would be good at it. I don’t think dad understands that!”

“It’s easy to see how silly your dad’s beliefs are. By his reasoning, if you were my daughter then I should make you like what I like. Since I like wearing feminine clothes like pretty dresses and high heels, I’d have to force you to like them! I’d have to call you ‘Butch’, ‘Dyke,’ and ‘Tomboy’ if you didn’t like pretty clothes.” But if I called my daughter those names your father would be angry with me!”

“I see what you’re saying mom,” Pete said. “Dad would be a hypocrite.”

“Exactly!”

Helen fumed at the thought that Bill had been blessed to receive two lovely sons yet he wasn’t grateful for who Pete was. She herself was happy to take Pete any way that he was. Every person on the planet had a right to be themselves. Donating DNA to create a person doesn’t give you veto power over who they become.

“I’m so happy to be able to spend a week with you,” Pete said.

“I’m glad you feel that way. We can use this week to get to know each other better.”

“I like that.”

“A nice way to get to know each other is to ask each other questions,” Helen said.

“That’s a great idea.”

“You ask me a question and then I’ll ask you a question. We can go back and forth.”

“Let me think. Okay. Do you wish that you had a daughter?”

“You’re asking that because of what I said before?”

“Yeah, I guess so. It’s like Dad got Chuck and me and you never got a daughter.”

“When your dad and I decided to have kids we had been thinking about having a boy and a girl. So naturally after Chuck was born we thought it would be nice if the next child was a girl. But then you came along and I’m totally thrilled and happy that you’re you!”

“But …”

“But what?”

“But Dad isn’t happy I’m me.”

“He’s happy you’re you. He can be disappointed because you’re not an athlete and still be happy that you’re you.”

“It’s so weird because you said he wanted a daughter. If I were his daughter then I probably couldn’t lift ten pounds with each of my arms – at least without a lot of practice.”

“You’re right Pete. Your father doesn’t make sense.”

Helen and Pete laughed.

“Could you and Dad have a third child maybe to get a daughter?”

“That did occur to us but your father made some good arguments that we couldn’t afford a third child.” Helen laughed. “The third child could have been a boy also!”

“Right. I didn’t think of that.”

“Anyway, Pete, we have a very nice family of four and I’m quite pleased with it! I just want everyone to be themselves. That’s a formula for happiness.”

Despite his mom’s upbeat thoughts about their family, Pete couldn’t fully dispel the idea that his mom was wistful about not having a daughter. It made sense. Maybe he wasn’t the booby prize but he still was a boy and his mom had had to learn to accept him as such.

“Can I ask you another question?” Pete said.

“Sure go ahead.”

“What’s your favorite color?” Pete asked.

“That’s easy. Pink.” Helen said.

“Now it’s your turn to ask a question.”

“What’s your favorite color?”

“I knew you were going to ask that!” Pete thought for a bit and said, “Pink is also my favorite color.”

“Why is it?”

Pete wasn’t expecting his mom to ask him why. He thought for a second and said, “At school I’ve seen girls wear pink dresses and tops. I like looking at them so I think that pink must be my favorite color. Why is it your favorite color?”

Helen laughed. “I’m a girl. Pink is often a color that girls love. Blue is supposed to be the color for boys.”

“I like blue, but pink is my favorite. Is that okay?”

“Sure. Some girls prefer blue to pink. Some boys prefer pink to blue. It’s not a question of one is right and the other is wrong.”

“This is so much fun Mom!” Pete said. “I’m really enjoying this!”

“So am I. There’s so much that we can learn about each other by asking questions.”

“Ask me another question Mom,” Pete said.

“Let me think. Is there a particular girl in school that you like?”

“Penny! She’s so pretty! She often wears pink dresses.”

“Are you going to ask her out?”

“Me? Oh no. I’m way too scared.”

“If all the boys are too scared to ask her out, then no one will!”

“It would be so much easier if she asked me out!”

“That might happen. Times are changing!” Helen said.

“I hope so.”

“Ask me a question,” Helen said.

“How come even though pink is your favorite color, you don’t usually wear pink clothes.”

“That’s a good question. Grown women wear pink less than young girls do. I do have some pink dresses and skirts but you’re right that I don’t wear them often. However, I often wear pink underwear. Even right now my underwear is pink.”

“Your underwear?”

“Does that embarrass you? To talk about ladies underwear?”

“I … never … thought …” Pete realized that his mother thought he might be embarrassed only because he was a boy. That wasn’t right and it showed that his mom didn’t ever get the chance to just be fully herself with her kids. She probably would like to talk freely about her underwear with a daughter. He decided to try and help her out. “No Mom. I’m not embarrassed. I’m really curious about your underwear.”

“You know I wear a bra and panties.”

“Underneath your dress?”

“Yes. You know what panties and bras are?”

“Panties are girl’s underpants. Girls wear bras because … my health ed teacher Mr. Ames said girls grow breasts. Girls wear a bra to carry them.”

“So you know about bras.”

“I saw Penny’s bra one day. I was behind her in the stairwell and looked up and I could see inside the sleeve of her shirt and I saw her bra. It was white. I think it was all lacy.”

Helen smiled. How typical. A simple thing like a peek at a girl’s bra and Pete can’t forget it. “It’s funny how you have an eye for detail!”

“I liked looking at her bra. Girls must really like wearing bras. Is that true?”

“Why do you say that?”

“Because they get to show everyone that they’re girls.”

“So wearing a bra makes a girl proud to be a girl? That’s an interesting idea.”

“That’s not true?”

“Not that I know of.”

“I guess I don’t know much about bras.”

“If you’re sure you don’t mind learning about bras and panties then I’ll be happy to teach you about them.” Helen realized that this is the kind of conversation she would have loved to have had with a daughter. She laughed to herself thinking that it’s the female equivalent of Bill telling Chuck how to shave or wear a jock strap.

“It’s interesting. I’d really like to see your underwear Mom. Is that okay?”

Helen laughed. “When I woke up today I wouldn’t have imagined being asked that question by my son. But it makes complete sense. So sure, you might as well familiarize yourself with my underwear – as long as you’re interested.”

“Thanks Mom,” Pete said. He gazed with anticipation at his mom’s dress wondering what he’d see when she took it off.

Helen stood up. “Let’s start with my panties. I’ll hike up the skirt of my dress to my waist.”

Helen lifted up her skirt exposing the top of her pantyhose with her pink panties inside.

“That’s your panty inside the stockings?”

“Not stockings, pantyhose. You see pantyhose is stockings with a built-in panty. I wear my pink panties underneath my pantyhose.” Helen pulled down the top of her pantyhose exposing her panties and sat down.

“I had wondered about what pantyhose were.”

“Stockings only go up to my thighs. To keep stockings up I need something to hold them. Later we can look through my girdles and garter belts to see how stockings get held up.”

“I didn’t know that” Pete said. “Do women like wearing pantyhose?”

“Some do, but not all women.”

“Why not?”

“Some women prefer the freedom of not having stockings on their legs. It’s a personal choice. I like the feel of stockings and the way they make my legs look.”

Pete stared at his mom’s panties. “Your panties are like my underpants except they’re much prettier.”

“True. Also panties are made from more delicate fabrics than boy’s underwear.”

“That’s because girls like that?”

“Yes, I suppose. Soft fabrics feel nice against the skin. Another reason is probably that panties don’t have to give support like boys underwear does.”

“Support?”

Helen laughed. “You know.”

“Know what, Mom?”

“What do boys have that girls don’t have?”

Pete laughed. “Duh! Boys have a penis!”

“Your underwear has to hold it.”

“Right. So a girl’s panty doesn’t have anything to hold?”

“Do you see anything?” Helen asked.

“No Mom. What’s neat is that your panty fits perfectly flat between your legs. That’s not at all like with my underpants. Should I show you?”

Helen laughed. She’d seen Bill in his underpants every morning and night for years and was well aware of the bulge in front. Obviously, Pete wanted to share intimacy with her. “Yes. Let me see.”

“Okay Mom.”

Pete pulled down his pants and took them off. “See how my underpants fit. There’s a little bulge in the front. Not smooth like your panties.”

Helen laughed. The scene was cute in a perverse way. “You can pull your penis back between your legs and flatten your underpants.”

“I can?”

“Try it.”

Pete reached inside his underpants and arranged his penis. When he was done the front of his underpants was flat. “Look Mom. Just like your panties!”

“I see.”

“That’s so neat Mom. It means I can be like you.”

“Yes you can.”

“Can I feel how soft your panty is?”

“How about I take them off. Then you can get a better look at them.”

“Thanks Mom.”

Helen pulled her pantyhose down to her knees and then carefully pulled them off her feet one leg at a time. Pete stared intently watching the process. “Pantyhose are delicate,” Helen said. “I have to be careful that I don’t cause a run in them.”

“I remember one time we were going to a restaurant and you got upset because you had a run. You wanted Dad to drive back to the house so you could change your stockings!”

“Good memory! There’s nothing worse than getting a run in a new pair of pantyhose. Ugh!”

Helen took off her panties and handed them to Pete. She was a little nervous exposing her bush in front of Pete but in an odd sort of way she had the feeling she was talking to a daughter and not a son. Pete had some definite female instincts or at least he was very good at mimicking girls.

Pete brought the panties up to his face to get a better look. “I love the shade of pink. The lace is so pretty Mom. It looks like flowers! I like the pretty bow on the front.”

“Often girls’ panties have a little bow on the front.”

“Why is that?”

“Many girls think the bows are pretty just like you do. It’s nice having pretty panties.”

Helen looked at the intent expression on Pete’s face. He was enthralled. His interest in her panties was genuine. Not licentious.

“There’s a cotton part in the middle,” Pete said.

“Yes. My vagina rests up against that part of the panty. Sometimes women leak a little fluid and the cotton absorbs it.”

Pete turned to look at his mom’s naked lower body. “That’s your vagina?” Pete asked indicating his mom’s bush.

The quick inclusion of her vagina into the conversation caught Helen off guard. She wondered if this was dangerous territory. Fortunately, Pete’s interest seemed educational and she saw no reason to reverse course. Being open and accommodating to Pete’s curiosity was likely the best way to steer the interaction away from lewdness. As long as she didn’t act like something was untoward then Pete wouldn’t see this intimacy as anything other than a mom and her son or more likely, daughter, getting to know each other better.

“Yes, well you’re actually seeing the pubic hair that grows outside my vagina. In the middle of the hair there’s a hole. Out of that hole comes fluids that the cotton panel on my panty is able to absorb.”

“Wow. What kind of fluids?”

“Pee pee is one of them. Sometimes when women laugh, particularly as they get older, a bit of pee might come out.”

Pete laughed. “That’s so funny!”

“It is funny but not so funny if you’re a woman and you end up feeling wetness in your panties because someone told you a joke!”

“I’m sorry Mom. What other fluid might come out?”

“There’s blood from the menstrual cycle.”

“I learned about that in health ed.”

“Good. There are also natural liquids in the vagina that might leak out a bit. Particularly when a woman gets aroused.”

“Aroused?”

“Sexually excited.”

“Oh wow. I don’t know much about that.”

“It’s okay. You’re still young.”

“With your hair surrounding the hole how do you know what your vagina looks like?”

“Good question. When I was your age and didn’t have pubic hair I could see my vagina. It’s been a long time since those days. Some women shave off their pubic hair so their vaginas are exposed.”

“Why would they do that?”

“Different reasons. Some bathing suits make it hard to hide the pubic hair. Especially if a woman has a big bush. Also a hairless vagina is quite sexy to boys.”

“Boys like to see a vagina without hair?”

“Some boys do. I’m actually curious to see what my vagina looks like. It won’t take long to shave it. I’ll just go shave it in the bathroom.”

“Can I watch?” Pete asked.

“Sure, why not.” Helen laughed inwardly thinking how much this was a mother/daughter experience.

Pete followed his mother to the bathroom sink. She turned on the hot water and wet her pubic hair. She put on shaving cream and began shaving herself with a safety razor. Pete watched every move.

While Helen worked she asked, “Do you have pubic hair? I haven’t seen your penis since it was a tiny thing.”

“I have been getting pubic hair. Mr. Ames says it’s normal at my age.”

“There are many similarities between vaginas and penises. It’s not obvious looking at them but biologists can point out parts which are the same thing but in a different form in the male and the female.”

“Wow. What parts?”

“The male glans and the female clitoris have the same underlying blood vessels and nerves. They differ in shape because of a hormone that only males have that causes the formation of the tubular penis.”

“What is the glans and clitoris?”

“The glans is the top part of your penis. The clitoris is the sensitive part of my vagina.”

“Sensitive?”

“Let me finish shaving and then I can show you what I mean. It’s too bad they don’t teach this in health ed.”

“Mr. Ames showed us a picture of the boys sexual parts and the girls but it was hard to follow what he was talking about.”

Helen finished shaving and washed off the shaving cream. Pete stared at the shaven vagina noting the slit and the puffed-up contour as if it were a little dinner roll. “Your vagina is fascinating Mom. I don’t know why but I find it so … pretty. I feel like it’s very special.”

“It is very special! You traveled out of it twelve years ago.”

Pete laughed. “I was a lot smaller!”

“I’ll say.” Helen got a mirror and used it to look at her vagina. “So that’s what it looks like.”

“That’s so funny Mom. You didn’t even know what your own vagina looks like.”

“There never was a need. I rather like it.”

“I do too.”

Helen spread the sides of her vagina apart. “I don’t suppose you can see inside very well but trust me when I say that my clitoris is right about here.” She had her finger pointing to a spot.

Pete looked closely. “It’s hard to see.”

“It’s easier to feel the clitoris, especially when it gets aroused. Because it gets hard and elongates. It’s then that it’s sort of like a penis.”

“Hunh?”

“You look confused. Give me your finger and keep your hand loose.” Helen guided her son’s finger to touch her clitoris. Pete liked the way it felt. Helen was sure she’d be going straight to hell for letting Pete touch her clitoris. But it seemed like an important point had to be made. She kept Pete’s finger pressed onto herself and then moved it slightly up and down. It felt intensely pleasurable.

“It’s suddenly moist and you’re right it’s become hard!”

Helen removed Pete’s finger. “I’m glad you got to feel a woman’s clitoris. In the future, you might meet girls that want you to touch it. Now you know where it is.”

“Thanks Mom. I don’t know if I’ll ever have a girlfriend but if I do I’ll try and remember where her clitoris is if she wants me to touch it.”

Helen laughed. “That’s such a sweet sentiment Pete. But I’m sure that you’ll one day have a girlfriend!” She wondered if Pete would ever tell his future girlfriend how he learned about the clitoris.

“Can you show me where my glans is?”

“You’ll have to take off your underpants.”

“It doesn’t bother you to see my penis?”

“I saw it years ago when it was tiny. I’m quite familiar with your dad’s penis.”

“Okay.”

Pete lowered his underpants and stepped out of them. Helen noted that Pete’s penis had developed quite a bit past his prepuberty form. He had a goodly amount of pubic hair. While it had been partially erect when Pete had first exposed it, his penis had grown a bit and was now standing up.

Helen held Pete’s penis with one hand and used the pointer finger of her other hand to touch a spot on the underneath part of the tip. “What does it feel like when I touch this spot?”

“It feels really good. It’s funny but it makes my penis jump a bit.”

“I’m touching your glans. I jumped when you touched my clitoris. That’s all been designed by nature to make boys and girls want to seek each other out.”

“You mean for sex?”

“Yes sex.”

Pete only knew about sex from Chuck’s descriptions of making out and feeling up his girlfriends. He liked that his older brother confided in him, though he also felt jealous. Having a girl as a friend must be the ultimate in happiness.

“I think you should also shave off my pubic hair,” Pete said.

“Really? Why?”

“That way I can be more like you.”

“That’s so sweet.” So this is what Bill had been enjoying from Chuck all these years. A son who loved being like him. What a great feeling it must be for Bill. Of course he never shared the happiness he felt with her. Now Pete is giving me my first taste of the kind of parental hero worship that has always been in the background of Bill and Chuck. “I’m happy to shave you.”

Helen put some hot water on Pete’s pubic hair. She applied shaving cream and began shaving him. She used one hand to position his penis away from where she was shaving. When she was done she washed off the shaving cream. “There you go. Your penis and balls are revealed in all their glory!” Helen and Pete laughed.

“That’s so silly Mom.”

“I know. I think everything you and I are doing is pretty silly. Luckily, Dad isn’t here. I’m sure he wouldn’t approve.”

“Because boys aren’t supposed to know about ladies underwear and their vaginas?”

“More or less, and especially their mom’s.”

Pete and Helen sat silently for a minute. “People have desires and feelings that just are part of themselves,” Helen said. “For example, I like being feminine. Those kinds of feelings bubble up within me so that pretty underwear, and pantyhose or stockings just feels right for me. Other women aren’t that way at all. But that’s okay too.”

“What does it mean if I have the same impulse as you Mom?”

“It just means that that’s you. You’re natural impulse is to be my daughter. That’s so dear. I love it.”

“So there’s nothing wrong for a boy to have the same feelings that girls do?”

“Yes. That’s what I’ve been telling you. There are many boys that feel like they’re girls and girls that feel like they’re boys.”

“It’s not just me?”

“Hardly. I’ve known a few women who see themselves as men. You’re the first boy I’ve met who feels like a girl. It’s things like this that make the world a much more interesting place than if everyone were the same!”

Pete wondered if he was certain that he was a boy who felt like he was a girl. It was hard to decide. What he did know was that he loved the idea of giving his mom the daughter that she had been denied. It wasn’t fair that she couldn’t have the closeness with a daughter the way his dad had with his son Chuck. The more Pete thought about it the more he realized that it made sense to think of himself as his mom’s daughter. It seemed to fit him better than thinking he was his mom’s son. He certainly was not his dad’s son!

“More than anything Mom I want you to be happy,” Pete said.

Helen almost shed a tear she was so moved. “How blessed I am to have a child who feels that way! You know of course that your happiness is most important to me also.”

“Yes, Mom.”

“Good. So tell me, where are we in our discussion?”

“You were going to show me your bra. You said it’s pink.”

“It is and it forms a set with my panty. Let me lower the top part of my dress so you can see my bra. Help me by pulling down the back zipper.”

“Sure, Mom.”

Helen turned her back to Pete and he pulled down the zipper to a point just above his mom’s waist.

“I see a strap across your back,” Pete said.

“That’s my bra strap.” Helen faced Pete again and pulled the top of the dress forward and pulled her arms out. “Voila! You can see my bra!”

“It’s pink just like you said. And it’s pretty. Lace and a little bow.” Pete stared at his mom’s bra in wonder.

“There are three bows!”

“You’re right Mom. I didn’t see the two at the beginning of the shoulder straps.”

“You see why I love this bra so much.”

“I do. It’s so neat that your breasts are inside the cups of the bra.”

Helen encircled her bra cups with her hands and gently lifted them up. “Yes indeed. These are D cup breasts. They’re fairly large.”

Pete stared at his mom’s bra. There was no doubt that this was the most beautiful sight he had ever seen in his life. The twin, rounded, prominent pink lacy cups of the bra were thrilling to behold.

“Oh my gosh Mom. I love looking at your bra!”

“Thank you.”

“I can’t get over the fact that the bra holds your breasts.”

Helen laughed. “The bra is designed to hold my breasts.”

“How do you do it?”

“How do I do what?”

“Get your breasts into the bra?”

“You mean how do I put on my bra? When you’re a girl you learn how to do it when you begin wearing them. Either your mom shows you how, or you watch other girls in the locker room or else you figure it out yourself.”

“How did you learn, Mom?”

“I don’t remember. It was a long time ago. I’ll take off my bra so I can show you how I put it back on. How I get my breasts into the cups.”

“That would be great Mom. It’s really interesting.” Pete couldn’t believe how delightful it was to look upon the bra on his mom’s chest. Bras and breasts were delicious. That much was certain.

“My bra is held on by the clips in the back.” Helen reached behind her back and undid the clips. She gently peeled the bra off of her breasts. “Here, take a good look at it.” Helen handed her bra to Pete.

Between the bra in his hands and his moms breasts on full display in front of him he had a surfeit of riches to look upon. He forced himself to concentrate on his mom’s bra. “It’s the same shade of pink as your panty! And it has the same kind of lace! Your bra is fascinating.” Pete ran his hands over the cups. “This is my favorite shade of pink. What is this hard thing beneath the cups?”

“That’s called underwire. Many bras use underwire to help with their job of holding up the breasts for hours and hours.”

“It’s not easy to hold up breasts?”

“Breasts of my size are a few pounds each. Imagine spending the whole day carrying two two-pound weights.”

“I see what you’re saying!”

Helen laughed. “Your enthusiasm is contagious.”

“I’m so glad you’re teaching me about bras. It must be nice knowing that you can wear something so pretty whenever you want to.”

Helen laughed. “Most girls would find that statement funny.”

“Why? They’re so pretty.”

“Yes, many girls like their bras because they’re pretty, and it’s true that many bras are comfortable to wear. However bras can feel confining and after wearing one for many hours they can even hurt a bit. The shoulders, or perhaps the underwire digs in.”

“Has your bra been hurting you today?” Pete asked.

“No, but it’s early in the day. If I put on my bra at seven in the morning by the time it gets to midnight, I’ll be quite happy to take it off!”

“You wear a bra for seventeen hours!”

“Some days. Of course, with large breasts like mine, a bra is more likely to be uncomfortable than a bra worn by a woman with small breasts.”

“Why’s that?”

“Small breasts put less weight in the bra. There’s less force on the woman’s body.” Helen laughed. “Imagine if you were wearing a bra Pete. The bra wouldn’t have any breasts to lift and it would probably feel quite comfortable no matter how long you wore it.”

“That’s neat Mom.” Pete’s imagination took off with a mental image of himself wearing his mom’s pink bra. With that fantasy came the self-realization that he wished it would come true. He would love to wear her bra.

“Pete?” his mom asked him.

Pete snapped out of his reverie. “I’m sorry.”

“Were you daydreaming?”

“When you said that I would probably find bras comfortable to wear it caused me to imagine myself wearing a bra.”

“I’m sorry. I got a bit carried away with the notion that I’m talking to my imaginary daughter.”

“I don’t mind. I’m really enjoying the discussion.”

“You have many qualities that I’d love to have in a daughter.”

“Thank you Mom,” Pete said and came over and hugged her.

Helen blushed a little as she felt her breasts pushing up against her son and felt his penis brush up against her thigh. She wondered if he was oblivious of their naked contact.

“This is what they call a love fest,” Helen said laughing. “When two people love each other so much!”

They stood facing each other and Helen saw Pete glancing at her breasts. “I completely forgot that you haven’t yet had a chance to get to know my breasts. You’ve never seen a breast before, have you?”

“No Mom. I really do want to get to look at your breasts. They’re so amazing!”

Helen laughed. “But you have seen breasts before! In fact, you’ve seen these very breasts. For a year and a half I breast fed you as a baby. You loved to suck on my nipples and get a delicious drink of mom’s milk.”

“I don’t remember!”

“Of course you don’t! None of us remember what happened when we were babies. But now you have an opportunity to refamiliarize yourself with my breasts.”

Pete found his mom’s breasts to be beautiful. His attraction to them was powerful and filled his heart with joy. He couldn’t think of anything else in life that was as thrilling and filled with happiness as the two breasts in front of him.

“As I said these are D cup breasts. I’ve been blessed with fairly large nipples. The puffy kind that looks like the nipples on a baby bottle.”

“Can I …?”

“Go ahead and touch my breasts if you’d like. Feel how heavy they are and how smooth the skin is.”

Pete gingerly reached out his hand and felt his mom’s breasts. He gently cupped one in his hand and lifted it slightly and moved it side to side.
“Unbelievable!”

Helen laughed. If Pete were her daughter then they’d both be waiting excitedly to see what came of Pete’s breast buds in the next year or two. Would Pete grow breasts as big as hers? She remembered her own development years ago. Her mother was just a C cup but both grandmothers were D cups and she ended up inheriting their breast size. When Helen passed her mother in cup size – she was fifteen when that happened – her mother congratulated her. That was silly since she had nothing to do with it!

“What age did you start wearing a bra Mom?”

“I was thirteen and I really needed one.”

“What do you mean?”

“Often girls start wearing bras because other girls are wearing them. They might not have enough breast to really need a bra but they don’t want to feel left behind. My mom, your grandma, wouldn’t let me wear a bra until I had breasts that were big enough to make it necessary. I was a full cup size when I first wore a bra.”

“I like hearing your stories Mom.”

“It’s so nice to have you listen to them!”

“I especially like stories about what it’s like being a girl. How you decided what style dresses you liked. What kind of purse do you use? Your first period. Your first boyfriend. The first time you kissed a boy. I think there are many ways that you developed as a girl that I’d love to hear about.”

“I’ll love to tell you those things.” Helen felt a little choked up. This was what she had always wanted. A daughter with whom she could share her own girlhood with. Instead she had been dealt two boys and up until this day, she hadn’t had an outlet for talking about her experiences of being a girl.

Helen looked at her watch and said, “It’s lunchtime. Time for lunch!”

She realized she and Pete couldn’t have lunch while naked. They would have to cover up their private parts again.

“We don’t want to eat lunch naked!” Helen laughed. “That would be just a bit weird. I’ll put my panties and bra back on. You should watch how I put on my bra.”

Helen took her dress off over her head. She stepped into her panties and pulled them up to her waist. Then she arranged the bra around her midsection, clipped the ends, swiveled it around. “Now’s the fun part!”

Pete laughed “You mean you have to capture your breasts into the cups?”

“Precisely. Watch me do it.”

Helen expertly put her arms through the straps of her bra and pulled it up using her free hand to assist in bringing each of her breasts into the bra cups. Then she adjusted her breasts within the bra. “Now my breasts are back to where they belong!”

“That’s so nice Mom,” Pete said. He hesitated putting on his underpants. It seemed like putting them on would put a close to the special intimate time he was having with his mom.

“You’re so affectionate Pete. It makes me sad to think that this wonderful part of you has been invisible all these years as your dad scolded you for having a gentle nature.”

Hearing his mom confirm his own conclusions about himself pleased Pete to no end. “This has been such a happy day for me!”

“Alas, you oughtn’t be naked for lunch!”

“I should put my underpants back on?” Pete’s voice was flat and unenthusiastic.

Helen picked up on his tone and said, “What’s the matter honey?”

“I just … I just …”

“What dear? You sound so sad! We’ve been having such a nice time.”

“I don’t want our nice time to end.”

“Why is it going to end?”

“If I put my underpants back on …”

Helen scrunched up her face wondering what Pete was implying. “You don’t want to wear your underpants? But you shouldn’t sit at the table naked!”

“I don’t want to be naked.”

Helen shook her head. “How else …” Suddenly it came to her. “You want to wear panties?”

“Is that bad of me? It’s just that you’re wearing panties. If I wore panties then I’d be like …”

“A girl?” Helen laughed.

“Or your daughter?”

“You want to pretend to be my daughter? Is that what this is all about?”

“Yes Mom. Is it okay?”

“You’re sure it will make you happy?”

“Yes Mom.”

Helen didn’t know what to think. Having a daughter of whatever sort Pete could manage to be was a gift from heaven. Especially now after twelve years of not having one. At the same time was she indulging herself at the expense of Pete’s future happiness? Judging by how happy Pete seemed it was difficult to disabuse Pete of his desires.

“Well then I’ll be quite pleased to have you as my daughter Pete! And my daughter certainly has to wear panties! I’ll find you a pretty pair of panties for you to wear. Give me a second!”

Helen went to her bedroom and came back a short while later carrying a white bra with a white panty. “I found an old bra and panty set of mine. I figured if you’re going to wear the panty you’ll want to wear the matching bra also. Am I right?”

“Oh my God Mom. Thank you!”

“Is white okay?”

“White is perfect!” Pete held the bra and panty as if they were sacred relics. He put the panty on and nearly swooned with happiness.

“I should help you with the bra.”

Following the same steps she had taken in putting on her own bra Helen helped Pete put on the white bra. Once it was on Pete stood motionless basking in the existential pleasure of knowing that he was actually wearing a bra and panty. Next to him his mother was also wearing a bra and panty. He felt a newfound closeness to her. This was a moment that could never be undone. It had happened. He wondered where this would lead.

“This is the most wonderful day of my life Mom! It’s so great to be wearing a bra and panty just like you do. I want to do everything that you do and I want to be just like you.”

“For this week we are free to be ourselves. No inhibitions! I’m perfectly happy to have you imitate me as much as you would like.” Helen was bothered by the empty cups of Pete’s bra. It didn’t look right on his chest. “Pete, remember the wooden chest in the attic where we keep old clothes and costumes? There’s a pair of foam falsies in there. Could you run up there and fetch them. You can wear them in your bra so that you have a girl’s chest like mine. I bet you’re going to love that.”

“Sure Mom.”

A few minutes later Pete returned wearing the white panty and the white bra with noticeable breasts. As excited and gratified as he had been to wear the bra, wearing the bra with breasts stirred his passion even more.

“How’s that Pete? You look like quite a sweet young teenage girl!”

Pete laughed. “Thank you! I feel like one I guess. I’m so thrilled that we’re dressed alike!”

“Let me find you something to wear for the rest of the day. You shouldn’t lounge about in underwear all day.”

Helen left and came back with a dress. “This is a wraparound dress. It can fit many sizes.” She put it on him and tied the sash. “See it fits you well enough. Tomorrow we’ll go to the shop and see about getting you some clothes that you’re comfortable with.”

“Thank you Mom,” Pete said. The dress his mom had gotten for him was blue and plain. It had a pocket on one side.

Helen put on her own dress and made their sandwiches and they ate at the table.

After lunch, the phone rang and Pete answered it. “Hi Dad.”

“Hi Pete. Chuck and I arrived at the park. Now we have to hike a couple of miles to our campsite.”

“Wow Dad that’s challenging.”

“Someday we’ll bulk you up enough to be able to do this hike also.”

“I don’t know Dad.”

“What are you and your mom up to?”

“We’ve been getting to know each other better. It’s a lot of fun being with Mom. We have a lot in common.”

“Good to know. Can you put her on?”

Pete fetched his mom. “Hi Bill! You made it safely?”

“Still have to hike to the campsite. I’m glad that you and Pete are doing well together.”

“We are. He and I are having a lot of fun together.”

“Just like me and Chuck!”

“True.”

“When I get back I should spend more time with Pete so he and I can get to know each other better too.”

“Good idea!”

After she had hung up, Helen said, “You know when your father gets back we can’t do this craziness?”

“I understand. I’m just glad for this chance to be close to you even if it’s just for a week.”

“I hope we will always be close Pete!”

“I’ll try to be. I assume that Dad will interfere with me being close to you.”

“How?”

“He won’t let me wear a panty and bra, will he?”

Helen laughed. “No you’ve got that right. I don’t know what to tell you about the future.” She debated telling Pete that he could wear ladies underwear under his clothes and put on a dress when dad and Chuck were out. She’d have to work that out later.

“It’s okay Mom. This is going to be the happiest week of my life. I’m going to try and enjoy it as much as possible!”

“That’s the spirit! For the first time since I’ve had kids I feel like I have an audience for the kinds of things that mean a lot to me as a woman.”

“What kind of things Mom?”

“We’ve been able to talk about our feelings for example. I’m not sure your dad and Chuck are capable of figuring out how they’re feeling let alone talk about them.”

Pete laughed. It was so nice to hear that he had qualities that his mom appreciated that his dad and Chuck lacked.

“You love Dad?”

“Of course. It’s hard to describe to someone your age, but there are many ways of loving in this world. A woman can love a man because of his manliness. In other words, the fact that he doesn’t have female qualities helps to make him attractive. At the same time, a woman can love a woman because she does have female qualities. Two different kinds of love and sometimes the same person can enjoy both!”

As Pete listened intently to his mom he doubted that he’d ever be able to love a woman the way a man does. It wasn’t in him to be like his dad or Chuck. Wasn’t going to happen. That left only one possibility. He’d love women in the way women do. Or? Would it be possible for him to love men the way women do? If he had love to give would he want to give it to a woman or a man?

“Could you love a woman?” Pete asked his mom.

Helen laughed to herself thinking how her thoughts had led to Pete’s question. “To be truthful I think that loving a woman offers things that I couldn’t get from a man. In that sense I can see myself loving another woman.”

“Things that Dad can’t give to you?”

“Yes. Men love women the way men do. That’s different than how women love women so it’s not like your dad isn’t loving me the right way. He is. But the special things a woman supplies in a loving relationship are things that I can imagine I would like.”

Pete wondered if he’d be able to supply a woman’s love to his mom. Lost in his thoughts he heard his mom say, “I’ve got some office work to take care of for the shop. How about we meet in a couple of hours during my coffee break. In the meantime you can wear the dress and otherwise enjoy yourself!”

“Thanks Mom.”

“One thing you might want to do is learn about makeup. It’s pretty fundamental to being a girl.”

“Sure Mom. How do I do that?”

“You can find many videos on YouTube that’ll teach you about makeup. I’ve seen a number of them myself by various girls and women.”

“Thanks Mom. I’ll look at them.”

“I’m curious to see what kind of makeup would look good on you. We can experiment tomorrow.”

“Thanks Mom.”

Before he did anything else Pete spent a half hour in the bathroom looking at himself in the mirror. He studied how he looked in the dress. Peeling back the dress at different spots gave him a view of the bra and panties underneath. It was all fascinating.

For the next hour Pete practiced his flute. Playing Bach and Couperin. Following that he watch videos about makeup. He loved the energy and enthusiasm of the girls who were not much older than himself. There was so much information, so many products, so many insightful tips that at first Pete was overwhelmed. By the time he got to the fifth video it started to make more sense. Then he rewatched some of the ones he had seen and it began to click for him.

Midafternoon Helen paused for a coffee break and invited Pete to join her in her bedroom.

“I was going to show you how girdles and garter belts hold up stockings. This is as good a time as any to let you immerse yourself in this aspect of ladies underwear. You can also familiarize yourself with my bras and panties.”

“That’s so nice of you Mom! I’d love to see all your underwear.”

“This drawer is bras and panties,” Helen said opening it up. You’re welcome to amuse yourself by looking through them. Please put them back as neat as you find them. I like my bras and panties to be neatly arranged in the drawer. There’s quite a variety if you have any questions feel free to ask. This next drawer contains my foundation garments.”

“Foundation?” Pete asked.

“Foundation garments assist women in obtaining the shape they desire. A nice, rounded tush, smooth hips, narrow waist. There’s a number of different ways to do it.” Helen opened the drawer.

“Oh my God Mom. These are so neat. What’s that?” Pete pointed to a folded pink garment.

“That’s a girdle. Girdles are on this side of the drawer. In the middle are garter belts and on the right side are slips. I keep my stockings and pantyhose in the lower drawer.”

Helen took out the girdle and held it up for Pete to see. He was beside himself with fascination. “It has garters to hold my stockings. This is called a panty girdle. This one here,” Helen said taking another girdle out of the drawer, “is an open bottom girdle.”

“It’s got garters too.”

“Most of the girdles have garters. If I wear stockings I attach them to the garters. Let me demonstrate.”

Helen lifted up her skirt, stepped into the open bottom girdle and pulled it up to her waist. She took stockings out of the lower drawer, sat down, put them on her legs and secured them to the garters. Rising to her feet she ran her hands around her hips. “See how wonderfully smooth my hips are. That’s what a girdle can do for a girl. At the same time it holds up my stockings so my legs are sexy.”

“Mom!” Pete said. “Many times you’re wearing a dress, you might be wearing a girdle and I wouldn’t even know it!”

“True. Just like you couldn’t tell I was wearing a pink bra and panty you can’t tell I’m wearing a girdle or a garter belt.”

“I’ve sometimes been inches away from your girdles and I had no idea you were wearing one.”

Helen laughed. “Sometimes you’re strange Pete. Of course no one can see another person’s underclothes. Could I see what underpants you were wearing this morning? Of course not!”

“Yeah but you’re wearing really pretty underwear. Not just underwear. And it’s a secret only you know!”

“Maybe you’re hitting onto a truth about women. There are times where a woman just wants to feel pretty. She’s not looking for other people to tell her she’s pretty. Do you see what I’m saying?”

“I’ve been feeling pretty wearing the bra and panty you gave me. That must be the same thing.”

“True. So you share many feelings with girls.”

Helen went back to work and until dinner was ready Pete went systematically and carefully through his mom’s clothing. When he came to the slips he asked his mom about them and she let him wear one of her half-slips.

***

For the evening Helen had found an old comfy nightgown for Pete to wear. The satisfaction Pete received from knowing that he was wearing a bra made him reluctant to take it off. He thought he’d go to sleep wearing it. No doubt his dreams would be improved.

For the hour before Pete’s bedtime, he and Helen watched the television together. Sitting side by side on the sofa Pete rested against his mother. She held him securely with her arm across his shoulders. Helen had never felt as emotionally close to Pete as she did now. For his part Pete was in a state of unbounded love for his mother. If Helen didn’t know better she would have thought the warm slender body in the pretty nightie was truly her daughter.

***

The next day Pete went to the shop with his mom. “This gives you an opportunity to look through the dresses and see if there are any that you like.”

“That’ll be fun.”

Underneath his pants and shirt Pete wore the bra and panty. “You should also look through the lingerie and shoes. Decide what you like. Of course you need to focus on women’s lingerie. We don’t have a great selection of D cup size in the teen bras.”

“Okay Mom. Thanks.”

At the dress shop a few customers were browsing through the merchandise. Pete had been to the shop a few times in the past. Sometimes Chuck would be with him. Typically the boys would sit in the back office and do homework while Mom worked out front.

“There’s also clothes in the backroom. When I get free I’ll check up on you.”

Pete slowly sauntered through the shop examining the dresses. In the back of his mind was the comfort of knowing that his mom encouraged him to find a dress that he would like to wear.

Among the dresses for women he saw numerous designs with flowers. Some with small flowers some with splotches of large flowers. He had fun imagining what they looked like on his mom. How would her breasts be accommodated? He was infatuated with the various bodice styles. Some had extra room for breasts built into them. Some were made of stretchy material that could expand to fit a range of breast sizes. He especially loved the lace decorations and bows that proliferated in some styles. He felt each dress to compare the soft fabrics.

He found prom dresses for sale in the section for teen girls. Colorful sun dresses proliferated. He didn’t have to look far to find pink dresses. There were a variety of those scattered around. His mom’s store was a little piece of heaven.

In the middle of a rack he saw the perfect dress. Pink, knee length, fit and flare style made of a filmy fabric. A crinoline was sewn into the skirt. Oh my God he thought. This is the most perfect dress! There were various sizes. His mom would know which one fit him best but it seemed that he was a size ten. He took one off the rack and held it up in front of himself. There’s no way he would be able to live without this dress!

He was lost in a reverie of how he might look in the dress, until he heard a familiar voice say, “Pete?”

Pete turned and saw that it was Penny and a woman who he assumed was her mom. “Hi Penny,” Pete said in a voice that sounded like a croak.

“I know Pete from school,” Penny said to her mom. “He’s one of the smart boys.”

“It’s a pleasure to meet you.”

“Thank you,” Pete said, nervously. He tried to process Penny’s comment that he was smart.

“That’s such a pretty dress!” Penny said.

“Thanks,” Pete said realizing that was a dumb thing to say. He blushed and said, “I mean, yes it is isn’t it?”

Penny turned to her mom, “This is what I was looking for. I love the pretty crinoline. Can I try it on?”

“Sure honey.” Penny’s mom looked through the dresses. “None of these are size ten. I’m sorry.”

“Darn, it’s so perfect!” Penny said.

Pete didn’t know what he should do. It felt wrong to hide from Penny that he was holding a size ten – unless he was planning on keeping it. But how could he admit to Penny that he wanted the dress for himself? There was also the problem of explaining why he was holding the dress in the first place.

“This one is a size ten,” Pete said handing it to Penny.

“Oh my God, it is! Thank you, Pete!” Penny smiled at him.

“You don’t want it?” Penny’s mother asked him.

“No,” he lied. “I was just helping my mom.”

“Your mom?”

Helen came over at that moment. “This is my mom. This is her shop!”

“Oh!” Penny’s mother said. “Penny and I love this place!”

While Helen and Penny’s mom engaged in a conversation about the store, Penny held up the dress to herself. “God I love this dress. When I saw you with the dress I was thinking that you loved this dress too. You gave it up for me! That’s so sweet!”

“I was helping my mom.”

“If you say so, but I saw you holding the dress up to yourself the way girls do when they want to imagine how they look in it.”

“Okay I won’t lie. That was what I was doing.” Pete scrunched his face up as if he were about to be hit.

Penny laughed. “I’m not going to make fun of you Pete. You look like you’re about to be slapped!”

“I guess it’s because my dad has made fun of me for not being like other boys.”

“Your own dad? That’s got to be hard!”

“Except that my mom is the exact opposite. She supports whatever I want to wear including girls clothes.”

“I guess I’m like your mother. If you like dresses you should wear dresses. I certainly love dresses!”

“That’s really nice to hear Penny.”

“What about this dress Pete? Is it your favorite?”

“Well yeah. I saw it and immediately thought it would be my favorite.”

“Then it’s not right of me to take it from you!”

“No Penny. I want you to have it. I’m sure you’ll be super pretty in it.”

“You too!”

Pete laughed. “I could never be as pretty as you Penny. You’re the prettiest girl in the class!”

“You’re too kind! If you’re sure about me having it, I should try it on.”

“Please do!”

Penny went to the fitting room. Pete’s thoughts alternated between happiness that he was Penny’s hero to being glum for not having the dress. After a few minutes Penny came out of the dressing room and Pete’s heart melted. She was so astonishingly pretty that he was sure he was now in love with her. The fitted torso hugged Penny’s modest chest. Pete wondered if she was wearing the same bra that he had once seen her wearing.

“What do you think?” Penny asked.

“You’re so beyond pretty. Wow Penny. I can’t believe how perfect the dress is for you.”

“Thank you Pete.”

Penny walked over to the two moms. Pete was jealous of the happy and carefree way she walked with the dress. She was so clearly in love with it. If he got to wear a pretty dress he’d do his best to walk the same way that Penny did.

Penny’s mom and Helen oohed and aahed about the dress. “It was made for you,” Helen said.

“What great luck,” Penny’s mom said. “It’s never easy to find the perfect pretty dress for Penny, and here we found it right off the bat. Thank goodness.”

Penny went back to the dressing room. When she emerged she gave the dress to her mom who went to pay for it.

Pete stood awkwardly waiting for Penny and her mom to leave before going back to his search of the dresses. Penny went up to him and said, “You’re not embarrassed about wanting to wear a dress? I want to make sure.”

“No, not after you said that you think it’s okay.”

Penny laughed. “You’re right to be afraid of the other kids in our class but with me it’s not an issue. I’ve always loved dressing in the prettiest clothing I can get. It’s hard to find another girl in class who feels the same way. The other girls see me as being a bit childish and I can’t argue with them. Even my mom thinks I’m ridiculous. But I just love being feminine.”

“It boils up from within you!” Pete said.

“That’s true!”

“That happens to me and I’m not even a girl. I still feel like I want to be feminine. My mom has been helping me learn how to be myself.”

“You’re lucky! Many parents would be alarmed!”

“I know. My dad won’t be happy if he finds out. He’s away for a week with my brother.”

“Chuck?”

“Yeah Chuck.”

“Everyone knows Chuck. He’s so cool.”

“I live in his shadow, but I don’t mind. He’s him and I’m me.”

“That’s a good attitude.”

They were silent for a minute. Then Pete and Penny began talking at the same moment. Penny said, “You go first!”

“I need to confess something!”

“What? It better be good!”

“I’m wearing my mom’s bra and panty underneath my clothes!”

Penny laughed. “So cool! Let me see!”

Pete opened a couple of buttons on his shirt so Penny could sneak a view of his bra.

“It’s white and very pretty, Pete. You’re mom has good taste in bras.”

“The panty matches my bra!”

“That’s nice. My mom’s bras and panties are kind of blah. But she indulges me by buying me only the bras that I decide are pretty enough.”

“I have one other confession,” Pete said.

“Tell me! This is fun. I like a boy who can’t hold any secrets!”

“In the stairwell one day at school I looked up and saw your bra. It was through your sleeve. I’ve never been able to get that pretty image out of my mind, not that I wanted to!”

“Come with me!” Penny said.

Pete followed her to a place just out of sight of their moms. Penny lifted up her blouse exposing her bra. “Here’s another look at my bra Pete!”

“It’s so pretty! This one is blue!”

“I have bras of many different colors.”

“Cool. So what were you going to tell me?” Pete said.

“What I was going to say was that we should get together and play dress ups! It’s my favorite game.”

“Dress ups?”

“We try on different outfits. I have lots of dresses and my mom also has some old bridesmaid and wedding dresses. It’s a lot of fun to put them on and pretend that we’re at different occasions.”

“That does sound like fun.” Pete rejoiced at his good luck of running into Penny like this. She actually invited him to her house!

“Good. We’ll arrange an afternoon. Maybe tomorrow will be good,” Penny said.

“Okay,” Pete said. “You know Penny for the longest time I wanted to ask you out – but I was scared to talk to you.”

“You should have, but I understand that you’re shy. That’s okay.”

“The thing is I would like to go out with you!”

“Oh, you mean like a boyfriend?” Penny’s expression turned serious. “I’m sorry Pete. I’d like to play with you but as my girlfriend. My other girlfriends are not into being feminine as much as I am. I love that you want to be feminine because that’s what I want to be. But if I’m dating I want to date boys. I mean boys who act like boys. Do you see what I’m saying?”

“Yeah, you’re right. It makes sense.”

“I hope I haven’t hurt your feelings!”

“No Penny. I’d love to play dress ups with you.”

“Fabulous!” A few seconds later Penny added, “I hope you won’t mind if occasionally I talk about boys I’m dating. I tend to want input from girlfriends.”

“Sure Penny. I’ll be happy to listen. Do you have a boyfriend now?”

“Not a steady boyfriend but I do go out on some dates. There’s one boy I sort of have a crush on but he’s a year older and probably sees me as being too young.”

“I’ll look forward to playing with you.”

“I can’t wait,” Penny said.

Pete and Penny returned to their moms. “Ready to go Penny?” Her mom asked.

“Yes. Can we invite Pete to visit tomorrow afternoon?”

“Sure,” Penny’s mom said. “If that’s okay with Helen.”

“That will be lovely.”

***

“Weren’t you lucky that Penny came in the shop!” Helen said after Penny and her mom had left. “Now you’ve got a date with her!”

“As a girlfriend,” Pete said.

“What do you mean?”

“Penny wants me to be her girlfriend and play dress ups with her. She only dates guys who act like boys.”

“I’m sorry Pete. Are your feelings hurt?”

“Maybe a little but I think I understand. It’s like you said before. Girls can love boys or girls or even both. Penny loves boys.”

“I’m sure you’ll one day find a girl who prefers boys like you.” Or, it occurred to Helen, Pete might fall in love with a boy who prefers that his girlfriend be a boy.

Despite his best effort Pete began to cry softly and Helen held him. It was his first rejection by a girl – though not at all a classic rejection. “I think you need to focus on Penny as a cup half full and not half empty. She really wants to play with you. Spend time with you. In time you’ll get to know each other better.”

“You’re right Mom,” Pete said. But he knew that deep inside he had a lot of love to give and he wouldn’t be able to give it to Penny.

After Pete got his emotions under control he said, “I really liked the dress that Penny bought. I was going to ask you if I could have that for my dress but it turned out there was only one size ten so I gave it to Penny.”

Helen laughed. “I have at least two or more size ten dresses in the back room. I don’t put all the dresses out at once. I’ll get you one. You can try it on in the dressing room to make sure it fits.”

Helen returned shortly with the dress. She looked around the shop. “We’ll close soon. No customers are here. Put on the dress and let me see what it looks like.”

In the dressing room Pete took off his shirt and pants and put the dress on over his head and his arms in the sleeves. He had no idea how to zip up the dress and as he left the dressing room to find his mother he called out, “I don’t know how to zip the dress up Mom.” It was then he noticed that his mom was talking to Ms. Kenyon a neighbor who lived up the street from them.

“Pete in a dress?” She asked my mom.

“It’s a new dress. Sometimes Pete helps me out by modeling the stock so I get a sense of how to display it.”

“That’s so generous of him,” Ms. Kenyon said. “I can zip him up for you.” Ms. Kenyon had me turn around and she zipped the back zipper. “A bra?”

“The dresses don’t fit right without a bra,” Helen said.

Ms. Kenyon smiled. “Does Chuck ever help with the dresses?”

Helen laughed loudly. “Can you imagine trying to get Chuck into a dress!’

Ms. Kenyon joined in laughing with Helen.

Pete noticed that Ms. Kenyon hadn’t thought it preposterous for him to wear a dress.

“Thanks for the exchange Helen. It’s so nice to see a young man being helpful to his mom,” Ms. Kenyon said to Pete.

“Goodbye Ms. Kenyon,” Pete said.

When she had gone, Helen put out the ‘closed’ sign. “Let me get a good look at you.”

Pete stepped away from his mom and stood in front of a mirror. He slowly turned around watching himself. While he was right about Penny being much prettier in the dress than he was, he still felt that he was sort of pretty. If his hair grew out he would look even more like a cute and coquettish young lady.

“I must say Pete that you’re stunning in that dress. You look like my little girl. My daughter.” Helen surprised herself by choking up a bit. She was amazed by how deeply happy it made her feel to know that Pete wanted to be feminine. It truly was as if he was the incarnation of the daughter that she had hoped to have.

After Pete changed back into his pants and shirt she escorted him to the lingerie and shoe sections. With her help they picked out a bra, panty, and pantyhose to wear with his dress. They had luck in finding him a pair of heels that matched the dress. “You’re all set Pete. Ah, except we’ll get you a soft nightie of your own!” They picked out a pink nightie for Pete and headed for pizza.

***

At home, Helen helped Pete put on his complete outfit. The new underwear, the pantyhose, the dress, the heels. All decked out for the first time Pete clung to his mom and sobbed with happiness. It was too much joy for one small boy to absorb.

“Am I like your daughter now?” Pete asked.

“Yes. There’s no doubt in my mind that you’re my daughter. You’ve made me very happy! I guess you’ll be my secret daughter from now on. When your dad gets back we’ll have to put this all away.”

“I know mom.”

***

Helen confirmed with Penny’s mom that Pete could visit Penny the following afternoon. The thought of spending so much time with Penny gave Pete chills of delight. At the same time, Penny’s rejection of him as her boyfriend stung deeply. He felt helpless. It was one thing to not be able to be a boy for his dad, it was worse that he couldn’t be enough of a boy for Penny to see him as a boyfriend.

The one truth of the last couple of days was his realization of how much Pete loved his mom. It was she that made this new life possible. Her tolerance, her encouragement, her honesty. The best part was that she loved him for whom he was. He didn’t have to be a boy for her. He could be a pretend daughter. Really he was just a girl whom she loved and he loved her in return.

***

Late that night Pete woke up with a start in the dark room. He’d been vividly dreaming of Penny. He was her girlfriend and was complaining to her that it wasn’t fair that he couldn’t be her boyfriend. “I can love you like a girl. My mom said I can. Why isn’t that good enough for you?”

“A girl loving a girl?” Penny said. “I don’t think so. I need a boy to love me.”

Fully awake now Pete couldn’t shake off his gloom. He imagined a day when he and Penny were dressed up in fancy dresses and one of her boyfriends showed up at her door. He’d have to watch Penny and the guy hold hands or kiss or something terrible. The guy would look at Pete and laugh.

The only person in the world who would allow him to love her as a girl was his mom. If he wanted to express the love that boiled up within him it would have to be to his mom.

Pete walked quietly down the hall to look inside his mom’s bedroom. In the dim light he saw her sleeping on one side of the bed. He tiptoed in and snuck into the bed next to her. He felt her warmth and listened to her slow sweet breathing. Here he was. A girl filled with all the love his mom could ever want!

A great desire to touch his mom swept through Pete’s body. Inch by inch he slowly moved toward her. His heart beat frantically. Helen’s back was facing him and he settled his chest up against it. His silky soft negligee brushed up against her negligee. He had kept his bra and breasts on with his panties.

After many minutes, his mom stirred a bit and shifted her body onto her back. Pete rested his head on her shoulder so his lips were touching her cheek. He slid his hand up inside her short nightie and rested it on her breast. His mind was outside his body looking in with awe and amazement at his courage. He felt like he might faint from happiness.

Helen woke up to a nice feeling coming from her breast. The last bit of a remarkably sexy dream eased itself from her mind and she identified the sensation on her breast as coming from a hand. “Pete?” she whispered.

Pete withdrew his hand. “I’m sorry Mom. I needed some love. I want to show my love for you. I love you.”

Helen wondered how she should deal with this. On one level it was wrong of her son to feel her up in her sleep. On another it was truly magical that her son loved her this much. She said, “You can continue playing with my nipple if that pleases you.”

“Thanks Mom,” Pete said. His hand gently resumed its grasping and smoothing of his mom’s nipple.

To her amazement Helen felt a slight wetness developing in her vagina. A late-night seduction by Pete was being appreciated by her subconscious mind. She turned to her side until she was facing Pete. She put her free arm across his back and forced him in tight against her. She felt his bra strap within his nightie.

“Your sleeping in your bra?” Helen whispered quietly.

“Yes Mom.”

Helen chuckled to herself. “You’re a pretty girl Pete,” Helen said softly.

Pete’s hand cupped his mom’s breast and then slowly slid along the side of her torso down to her hips. Helen felt electrical impulses shooting up and down her spine. Pete must be a natural born lover. The gentle and caring way he touched her caused a gush of wetness in her vagina. She wondered where this was going.

“I love you Mom,” Pete said as his hand reached his mom’s thigh. It was then that Helen figured out his destination. Her breathing increased in depth and she felt her heart beating faster and harder. Her mind began protesting. She mustn’t let this escalate. It was wrong. But was it? No it had to be. She was frozen and unable to push Pete away. She was now almost desperately waiting for his finger to arrive.

“I love you Pete,” Helen said now. She knew she couldn’t pull away. She had to find out what Pete was going to do.

His hand now gently crossed her thighs and as she anticipated she felt his fingers assembling over her shaved vagina. Not once had Bill ever gotten her this aroused in all the many times they made love. Bill seemed to think that his contribution of an erection was all that was required of him. With that established he’d do his thing. Use her vagina to wash away the surfeit of hormones in his blood stream responsible for his horniness.

It was those times that Helen thought of what making love to a woman would be like. The special ease, grace, concern of a woman would no doubt lead to a sexual experience that was built on her own orgasm. Night and day different than love making with Bill. And now the anticipation of what Pete was about to do was causing small mini orgasms to erupt in her vagina.

Helen tensed up as she felt one of Pete’s fingers pushing now to enter into her vagina. Then he found her clitoris and she nearly swooned with pleasure. He slowly rubbed his finger up and down the hard swell of her clitoris. She was wet and lubricated and the little finger had no trouble slipping along down and up.

Then she nearly leapt out of skin with an orgasm. Almost immediately she could sense herself building toward a second one. She threw all caution to the wind and moved her lips until they met Pete’s and she began kissing him. She pushed her mouth forcefully against his and slipped her tongue into Pete’s mouth. All the time the vast pleasure emanating from her vagina kept up at a steady pace.

A second orgasm even more powerful than the first came and went and still Pete’s finger kept her vagina enslaved to the pleasure that only he knew how to coax out of her. Finally she pulled Pete’s panty down his legs and off. She turned Pete onto his back and took off her own panties. She lay down on top of Pete with her breasts pushing into him.

“Oh Mom I love you!” Pete said again.

Helen’s hand found Pete’s erect penis and held onto it. He yelped in pleasure as she guided it to the opening of her vagina. Then frantically and savagely swallowed up his penis into her. She pulled her hips back and then shoved them back again taking in his penis. Pete wailed and moaned. The pleasure Helen took from this violation of her son soared up to a level she had never imagined existed. She pounded away on her son until his screaming climax spurred her onto an orgasm unlike any she had ever had before.

After a minute in the dark room she rolled off of Pete and lay on her back. Pete faced her on the side and gently kissed her shoulder. “I love you Mom.”

“I love you too my darling.” A few minutes later Helen said, “You should get back to bed.”

“Yes Mom.”

Helen heard Pete’s bare feet as he walked back to his room. There was only one way to view what had just happened. It was a dream. She dreamt it. Pete never came into her bedroom. It never happened. She wondered if in the morning Pete would also see their love making as a dream.

Once Pete was back in his own bed he began to cry. These were tears of joy and relief. His mom had allowed him to express his deepest love for her. She had accepted his love and returned to him all the love of her being. He had been an instrument of her pleasure. The memory of his mom powerfully putting him on his back and using his body as she saw fit was magical. As tired as his penis was from its recent climax, it swelled up again and twitched. When his tears stopped he smiled into the dark. No matter what happened in the future, he knew that his mom accepted him for who he was.

***

At breakfast the next morning Helen said, “I had the strangest dream last night.”

“So did I!” Pete said.

They smiled at each other. What had transpired between them would forever be a figment of the imagination. A wild late night dream sequence. Never to be revealed to anyone.

“Am I like a girl to you?” Pete asked Helen.

“Yes, you are. After our time together I have to say that you are a girl, my daughter.”

“Do you love me more because I’m a girl? I mean you loved me as a boy but now that I realize that I’m a girl does that make you love me more?”

“I don’t love you more because you now see yourself as a girl. The reason why is that even when you were a boy you were really a girl who just happened to think they were a boy. I couldn’t very well verbalize what I was seeing but now our time together has shown me this fundamental truth.”

“Yesterday you said that girls can love each other.”

“That’s true.”

“That’s our love then.”

“There might be an element of that, but I have to say that I mostly love you as a parent loves their child.”

“Is your parental love for me as a boy or a girl?”

“I love you for being you. If you feel that you’re a boy I love you as a boy. If you feel that you’re a girl I love you as a girl. That’s what I’m getting at.”

“But you prefer me being a girl?”

“Yes, but only because I think you see yourself as a girl. You don’t like being a boy and never have liked it.”

“I see what you’re saying.”

***

Pete walked to Penny’s house carrying the few items that she had told him to bring. His favorite dress, some underwear, and his high heels. When he arrived Penny’s mom answered the doorbell and she smiled broadly at him. “So nice to see you again Pete,” she said. “You’ve brought some clothes for the dress ups?”

“Yes. Penny asked me to.”

“May I take a look?”

“Sure.”

Penny’s mom looked in the bag. “You’ve got the same dress as Penny.”

“My mom found another size ten in the back.”

“Penny will be so pleased to hear that. She was distressed that she’d taken your favorite dress. She knows how important a favorite dress can be to a girl!”

“Yeah I was very happy to find I could get this dress.”

“I love your heels. You’ve also got some pretty underwear. I guess you’re all set! Penny’s room is at the top of the stairs to the right. You can’t miss it.”

“Thank you,” Pete said.

He ascended the stairs and stuck his head in Penny’s room. “Hi Penny.”

“Hi Pete,” Penny said. She closed the door. “I’ve got a perfect dress up for us to play today. We’ll be a famous singing act: The Starlight Sisters. We can give a concert, be interviewed by a radio station, appear on the red carpet at the Grammys, and whatever else comes to mind! What do you think?”

“I love it. What do we wear?”

“You brought your favorite dress?”

Pete laughed when he took his dress out of the bag. “My mom found another size ten!”

“Hooray, hooray. I’m so glad you got the dress. I was feeling bad about it.”

“Your mom said that. You shouldn’t have felt guilty. You’re so much prettier in the dress than me.”

“That’s debatable! Having the same dress is perfect for today. The Starlight Sisters wear the same dress as part of their act!”

“How do we play dress ups?”

“Right. We start right now. Pete and Penny are the two Starlight Sisters getting ready for a show. First thing is we must put on our makeup. Come with me!”

Pete followed Penny to a desk with mirrors and various makeup bottles, tubes, compacts, brushes, and combs. “Our makeup girl is out today. We’ll have to do our makeup ourselves.”

“I’ve watched many videos but I haven’t actually done it.”

“I sympathize sister dear. It’s not easy. I’ll help you.” Penny examined Pete’s face for a bit. “I’ll do some basic makeup and we’ll see how that goes.” Penny talked her way through each of the different steps. “First some primer ,.. next is the foundation … now your eyebrows get some attention … I’m applying eye shadow now … some eye liner … mascara … and on to rouge and last but not least some lipstick.” When she was done Penny stepped back to look at Pete. “You look so lovely. A beautiful Starlight Sister! What do you think?”

Pete looked at his face. “It’s unbelievable. You’ve done just as good a job as our makeup girl!”

“You have a natural prettiness. I’ve just heightened it.”

“Thank you Sister!”

Penny did her own makeup. When she was done she said, “What bra are you wearing for the concert?”

“One of my new bras,” Pete said taking his top off. “I thought my fans would appreciate a little bust enhancement so I’m wearing my falsies today.”

“Aren’t you clever.” Penny took off her blouse and Pete was captivated by her lime-green bra. It was a pretty sight.

“I’m wearing my matching panties!” Pete said and he pulled down his pants. He surprised himself a bit by how prominent his penis had become.

Penny saw it and laughed. She took off her shorts and Pete saw that her panties matched her bra.

“Now our stockings sister!” Penny said.

“I’m wearing pantyhose,” Pete said.

“I prefer stockings,” Penny said. She put on a garter belt and sat down and put her stockings on and attached them to the garters. While she did this Pete put on his pantyhose following the technique his mom had shown him.

When they were done Penny said, “Our dresses!”

Pete and Penny slipped their identical dresses over their heads. They took turns zipping them up the back. “Aren’t we pretty!” Pete said looking in the mirror. He was enamored of the outfit and especially smitten by the makeup that Penny had put on him. The lipstick was a special delight.

“The Starlight Sisters!” Penny exclaimed.

They put their heels on and stood side by side holding each other and looking in the mirror. They looked like a real singing group Pete thought. His hair needed to grow out but apart from that they shared similar traits. Their height, weight, bone structure were similar.

Penny took Pete’s hand and said, “My mom is interviewing the Starlight Sisters. Then we give a concert. Come with me!”

They went downstairs where Penny’s mom greeted them. “I’ve got to take pictures for the fan magazine!” Pete and Penny posed for photographs. Penny took Pete to a piano where she had him sit next to her. She had sheet music for a number of songs and she played and sang with Pete joining her. Penny’s imagination propelled them throughout the afternoon.

Penny invited Pete to stay for dinner and Helen gave her permission. The evening ended with Pete and Penny sitting side by side on a loveseat in the screened-in porch wearing their identical dresses. “The famous Starlight Sisters!” Penny said. She held Pete’s hand. “This has been the funnest day Pete. None of my other girlfriends have ever slipped so easily into dress ups as you!”

“I can’t remember ever enjoying myself this much,” Pete said. “I love playing with you. You’re so smart and inventive. It’s hard to keep up but I love it!”

Helen’s car pulled up in front of the house. She rang the bell and became engaged in chit chat with Penny’s mom. Pete and Penny lingered on the porch together. Feeling the warmth of Penny’s hand Pete felt a great desire to kiss Penny. How he would love to be her boyfriend. It didn’t make any sense why Penny could spend the day with him having such fun but not allow him to be her boyfriend. It was painful to contemplate that their wonderful relationship would never get more serious than it is now.

A short while later Helen fetched Pete from the porch. He thanked Penny and her mom profusely for the great time. Helen said she hoped that Penny would come by for a visit also. Penny and Pete agree that they’ll play dress ups again in the near future.

***

Ten o’clock that night Penny called up Pete. She was in a state of agitation. “Sorry to disturb you so late!”

“No problem Penny! What’s the matter?”

“You remember I said you couldn’t be my boyfriend because you don’t act like a boy?”

“Yes,” Pete said. He wondered why Penny would bring that up again.

“The thing is, after today, I got to thinking … I’d rather us be two girls together than be with a boy. What I mean is that I hope you’re still willing to be my boyfriend even if you don’t act like a boy.”

“Oh my God, Penny! Yes of course. I’d love to be your boyfriend and yet be a girl when I’m with you.”

“Thank goodness! I’m really sorry I hurt your feelings. After the time we spent today I realized that every time I’d be on a date with a real boy, I’d be wishing he’d play dress ups with me.”

“That’s funny! You know I was worried about meeting your boyfriends. I was going to be so jealous.”

“Let’s put that all behind us. We should play dress ups again soon. And also we can go on a date!”

“That’s perfect!”

After he hung up Pete went to his mom. “That was Penny on the phone. She changed her mind and wants me to be her boyfriend!”

“I’m so happy for you!” Helen said.

“Yeah. She realized that if she were on a date with a boy she’d be wanting him to be playing dress ups with her.”

“Good. I’m glad that’s all settled.”

“The thing is Mom …”

“What dear?”

“I’m worried that you’ll think I’m rejecting you. Last night I truly did love you as a girl and as your daughter. But now I think it’s best if I just love you as your daughter.”

Helen had to use every bit of self-control not to bust a gut laughing. “I understand Pete. It’s best this way. I do love your father and it would definitely be complicated to also receive the love of a girl like you at the same time.”

“Thanks for being so understanding Mom. Our love was brief but very pleasurable.”

“I will treasure the memory but keep it forever in a lockbox in my mind.”

“Same with me Mom!”

“Just think that your dad will be so impressed that you’ve got a girlfriend now. And Chuck will be jealous! Penny is so pretty!”

“I know Mom. I was thinking the same thing.”

Pete hugged his mom good night. Helen held her son tightly. Somehow she would find a way to protect him from the world, from his father, from everyone who wouldn’t let him be himself.

The End