The New Neighbor

By Pamela

([email protected])

“Have you seen our new neighbor?” Steve asked his wife Cecilia.

“I waved to her,” Cecilia said. “I saw how she was dressed. Very stylish and sophisticated. Not exactly what this neighborhood is known for. Don’t get any ideas!”

Steve laughed. “A single woman buying old man Grimps house. I never expected that.”

“What were you expecting?” Cecilia asked.

“I imagined a nice family with some kids. There’s a lot of room for a single person.”

“True. I hope she’s going to be a perfect neighbor. She waved back at me pleasantly. We should find out what she does for a living. Why she dresses so …”

“Sensually?” Steve hazarded.

“I was going to say feminine. Yes. That’s it. Her pretty dress with spiked heels and hose. I’m sure that dress is from Saks. It’s what a super model might wear. Her hair is in a beautiful sexy style. I wonder if she ever just wears jeans and a tee shirt.”

“She might. We’ve only seen her this once. Maybe she likes to dress up for moving day,” Steve laughed.

“I’m going to visit her with a plate of brownies. Welcome her to the neighborhood,” Cecilia said. “You should come with me.”

“I can’t. It’s bowling night.”

“Right, I forgot.”

“Take Tommy with you. You can explain that he cut the grass for Mr. Grimps. She might want to keep him on.”

“Good idea,” Cecilia said.

***

That evening Cecilia brought a plate of brownies over to the new woman accompanied by Tommy, her fifteen-almost-sixteen-year-old son.

“That’s so lovely of you to bring brownies!” the woman said. “I’m Juliana Weathercourt.” She was wearing the highly styled dress and stockings that they had seen her wearing earlier in the day. In place of heels she was in her stockinged feet.

“I’m Cecilia Morton and this is my son Tommy. Welcome to the neighborhood!”

“That’s so kind of you.”

“We knew Mr. Grimps quite well for many years, and it saddened us when he died. But now is an opportunity to make a new acquaintance.”

“I’m so glad you came over. The brownies look delicious. Tommy is in high school?”

“Yes, I’m a junior.”

“Marvelous,” Juliana said. “What are your interests?”

“I’m not totally sure. Maybe rocketry. I’m on the ping pong team.”

“He won a trophy,” Cecilia said.

“Third place in a minor tournament. I was just lucky in the final match.”

“I like a modest man,” Juliana said. “I’m sure you’re quite talented.”

Surrounding them were many cartons in various stages of being unpacked.

“If there’s any way we can help you now or in the future, please let us know,” Cecilia said. “My husband, Steve, is quite handy. He couldn’t come over tonight, but I’m sure he’ll introduce himself soon.”

“Thank you for your offer. I have to admit that I’m not a practical person. My work is in modelling – usually for corporations at trade shows.”

“How fascinating,” Cecilia said. “I was going to mention that Mr. Grimps had Tommy mowing the lawn and he’d be happy to continue for you if you’re interested.”

“I am, I am. That solves one of my problems. I was wondering how I’d get the lawn mowed.”

“I use my dad’s self-propelled mower. It’s easy,” Tommy said.

“Wonderful, I can use all the help I can get! Before you go, Tommy, could I impose on you to carry a few of these cartons upstairs. I daresay they’re too heavy for me and I forgot to get the movers to put them up there.”

“Sure, I’ll try,” Tommy said. Juliana pointed to the cartons and Tommy grabbed onto the first one and tried to lift it. “I’m sorry but it’s too heavy for me,” Tommy said.

“Oh, I’m sorry. I didn’t realize that.”

“Maybe the three of us can lift if upstairs,” Cecilia said.

“Good idea,” Juliana said.

The two women and Tommy each put their hands on the carton and lifted it up. They carefully walked it up the stairs with Cecilia taking the brunt of the weight. Juliana steered them into the master bedroom where they put the carton on the floor.

“I had the entire upstairs redone,” Juliana said. “I had some extra closet space added to the bedroom.”

“I see,” Cecilia said.

Cecilia was surprised by how feminine the room was. The walls were pink. The bedspread was pink with roses in it. The curtains were a light pink lace. The carpet was thick, light pink.

“The bathroom was redone also,” Juliana said.

“It’s a very pretty bedroom and I love the bathroom,” Cecilia said. It had pink tiles.

“I know I go overboard with the feminine. My job demands that I wear many pretty outfits – situations where a feminine presence adds to the ambience. I guess I’m like a decoration but it pays quite well and it’s given me a ton of clothes!”

“I see,” Cecilia said. She and Tommy peeked into one closet and it seemed to be filled with a hundred dresses hanging at two different levels. Beyond it was a room with more crinolines than one could count. It was a veritable rainbow of colors.

Juliana laughed. “I know. So many crinolines and dresses but they are so pretty and I do love wearing them. That closet over there is my lingerie closet. I sometimes do lingerie modeling and invariably I end up with more and more bras, garter belts, girdles, bustiers, bodysuits.”

Tommy walked over to it and looked inside. He was spell bound by what seemed like an infinite variety of women’s underwear.

Juliana and his mother watched him for a minute until Juliana said, “It’s quite a collection isn’t it?”

“Yeah,” Tommy said.

“I think he’s mesmerized by your underwear,” Cecilia said, laughing.

That snapped Tommy out of his reverie and he turned back to the women. “Shall we get another carton?” Cecilia said.

“I can’t thank the two of you enough. You’re lifesavers!”

They descended the stairs and hoisted two more cartons up to Juliana’s bedroom.

***

When Steve came home from bowling Cecilia and Tommy were watching television. “What did you learn about our neighbor?” Steve asked.

“She’s a model like you guessed,” Cecilia said. “The most amazing thing is she had the second floor redone creating a ton of extra closet space for the master bedroom.”

“That’s interesting.”

“The whole upstairs is super girly!” Tommy said.

“Feminine,” Cecilia said. “Juliana is one of those women that enjoys being pretty and dressing pretty.”

“And living pretty!” Tommy said. “She’s got pretty pink walls and carpet and everything!”

“Cool. What’s in her closets?” Steve asked.

“One room was totally full of these fancy little dress things in so many colors and lengths!” Tommy said.

“He means crinolines and petticoats,” Cecilia said. “Tommy is quite right. A whole room of them. I suppose she needs them. You saw the dress she was wearing today. The short, cute, skirt that flared outwards due to the crinoline she was wearing. It’s a very sexy and feminine look. Especially with her stockings and heels.”

“I hadn’t noticed,” Steve said and Cecilia elbowed him playfully.

“I’m going to have to chaperone you every time you go over there!” Cecilia said.

“Rats!” Steve said.

“She also has a lingerie closet,” Tommy said.

“Really now?” Steve said.

“Yeah. I couldn’t believe how many different kinds of things she has in there.”

Cecilia laughed. “Tommy found it so fascinating. But Tommy dear, they’re just bras, panties, girdles, slips, stockings. Like any woman has.”

Tommy for the first time realized that underneath his mom’s dresses and other clothes she’d be wearing women’s underwear. He’d never thought about it before. Would her underwear be like Juliana’s? Then he remembered that he’d seen his mom’s underwear many times when she was doing the laundry. From what he could remember his mom’s underwear was not as fancy as Juliana’s.

***

Over the next week each sighting of Juliana had her wearing a pretty, feminine dress, stockings, and heels. Some dresses were above the knee, some at the knee and some below her knee. In every case she must have been wearing a crinoline or two to achieve the poufy look that she seemed to prefer.

On a couple of occasions Steve had a chance to chat with Juliana and he and Cecilia compared notes as to what they thought about her.

“I think we lucked out in the neighbor department,” Steve said at dinner one night. “Juliana is always so pleasant.”

“True,” Cecilia said. “Her outfits are gorgeous. She’s one of those women that are at the far end of the femininity spectrum.”

“What does that mean?” Tommy asked.

“Girls can go from the ultra-feminine like Juliana all the way to girls that are hard to distinguish from men. They wear men’s clothing and act masculine.”

“What about boys?”

“Boys also! They can go from super masculine with big muscles and hairy chests all the way to delicate, effeminate boys. Boys who are as feminine as Juliana.”

“Do you know any men like that?” Tommy asked.

“Can’t say that I do,” Cecilia said.

“I knew a boy like that in high school,” Steve said. “I didn’t envy him – the other guys teased him because he was feminine.”

“What did the girls think about him?” Tommy asked.

“Good question,” Steve said. “Some girls had no problem with him. Others made fun of him.”

“Kids are prone to do dumb things,” Cecilia said, “because their brains are only half formed.”

“My brain is only half formed?” Tommy asked.

“I’m afraid so,” Steve said.

“Don’t listen to your father,” Cecilia said. “You should never tease anyone. You should be tolerant of whatever people do as long as they don’t purposefully hurt someone. If there’s no victim there’s no crime.”

“Your Mom is right,” Steve said. “Every person on the planet is unique – and has no more or less right to be themselves than anyone else. Bullies who tease kids are imposing their wishes on others.”

“Thanks Dad,” Tommy said, “I’ll keep that in mind.”

***

The next day Juliana called over to ask if Tommy would be interested in a daily job of taking care of the cat she had just bought. Tommy was thrilled to earn a little extra spending money and arranged to meet with her to find out what she had in mind.

“I’d like you to look in on the cat, her name is Trixie, every afternoon to make sure she has food and water and to clean her cat box,” Juliana said. “I’m training Trixie to never go upstairs, so if you don’t find the cat downstairs when you come in, please look for Trixie upstairs. You have my permission to scold her and take her downstairs.”

“Okay, I can do all that,” Tommy said.

“Great. I’ll give you a key and you can start tomorrow!”

“Thanks so much, Ms. Weathercourt,” Tommy said.

“You can call me Juliana.”

“Thanks, Juliana.”

“Let me introduce you to Trixie,” Juliana said.

“Hi Trixie,” Tommy said.

Juliana faked the cat’s voice saying, “Hiya Tommy!” and Tommy and Juliana laughed.

***

A few days later when Tommy went to check up on the cat he found that she wasn’t downstairs. After a search upstairs he found her in the lingerie closet. He picked her up and gazed with awe in every direction. Shelves and shelves of women’s underwear. He recognized the bras and panties. Other garments – some with dangling clips – he wasn’t familiar with. There were a number of built in racks holding a myriad of delicate negligees and other lacy clothes. One rack had hangers holding matching bras and panties. One whole corner of the room seemed to be devoted to stockings and pantyhose.

The range of colors impressed Tommy. Whites, beiges, black, pinks, red, blue. Many pastel shades of these colors. It was hard to comprehend how Juliana could ever figure out what she wanted to wear on any given day.

Tommy went downstairs with the cat and scolded Trixie for going upstairs. Trixie looked at him amused as if to say, “What are you planning to do about it?”

***

After dinner Tommy noticed that Juliana’s car was in her driveway and he told his mom, “I’m going next door to tell Juliana about her delinquent cat.”

“Okay!” she yelled from the kitchen.

Tommy rang Juliana’s doorbell and she ushered him in. “Can I make you a coffee?”

“Sure, that would be great,” Tommy said.

Juliana prepared one for Tommy and herself and joined him in the living room. “So what’s up Tommy?”

“Today I found Trixie upstairs,” Tommy said.

“You did? Oh darn. That darn cat!” Juliana said. “What room was she in?”

“I searched the bedroom and closets and found her in your room with all your … you know …?”

“My what?”

“You know … um.”

“My dresses?”

“No.”

“My crinolines?”

“No. The one next to that.”

“You mean my lingerie closet!”

“Yeah.”

“I must have left the door slightly ajar.”

“Yeah, I did see that it wasn’t closed.”

“Trixie took advantage of that. I guess she likes lingerie!” Juliana said and laughed. She saw that Tommy wasn’t laughing and said, “I’m sorry. It’s clear that my lingerie closet makes you uncomfortable. Is that true?”

“Yeah, I guess it does. Is that wrong?”

“Not necessarily. It depends on why you’re uncomfortable.”

“This is very embarrassing.”

“No need to feel that way. The best cure for things that make us uncomfortable is to confront them directly. Let’s go to my lingerie closet together and you can talk about what you’re feeling.”

Tommy looked nervously at Juliana. “Sure. Maybe I can figure out what I’m feeling.”

“Good.”

Tommy followed Juliana upstairs and through her bedroom to the lingerie closet. Tommy looked around nervously and Juliana asked him, “Tell me what's going through your mind.”

Tommy looked at the bras and panties and many other garments. “I feel … I feel … can I say anything?”

“Sure, Tommy. Just be honest. I’m not here to criticize you or judge you.”

“Well the truth is your underwear is very sexual. I get sexual feelings. I’m sorry …”

“Don’t be sorry. Lingerie is often designed to excite men.”

“Really?”

“Sure, because it’s feminine and is associated with the parts of a woman that men find sexual.”

“You mean like a bra …”

“Yes, Tommy. A bra is what women wear to hold up their breasts. Men tend to have a great desire for breasts so naturally the garment that holds them up will be part of their lust.”

“And panties?”

Juliana laughed. “A woman’s panties cover her vagina which is definitely of interest to men. So it’s normal for men to feel sexual among lingerie.”

“Yeah, I do feel sexual but it’s … it’s hard to describe. It’s like I look at one of your bras or panties and I feel like why shouldn’t they be for me? There’s this girl thing I feel inside. Like I want to be within a girl body that wears the bra and panty. I want to climb inside it, somehow. You’ve got this magic of being a woman. You’re on the inside. I’m outside looking in.” He paused a second and said, “I’m sorry, sorry, sorry for ranting like this. It’s crazy. Everything I feel is so mixed up!”

“All this is you saying you want to be a girl?”

“Yeah.”

“But you already are a girl. In your mind if not your body. Your turmoil comes from your mind not yet realizing that you are a girl. Only a girl would be so upset that she can’t wear lingerie.”

“But my body!”

“Yes, there’s your body and there’s also years of habits in acting like a boy because that’s been trained into you. But all that is superficial. You can change your body to some extent. You can unlearn the male habits and learn to express yourself as a female.”

“I never knew any of this … I’ve always been so afraid to be a girl.”

“Well today you’ve been wonderfully courageous. I applaud you for speaking the truth. It arouses in me a desire to see you be happy – to see you fulfill your longings.”

“My whole life I've had suspicions about myself but I've refused to act on them. I've been frozen. But your lingerie closet is like a bonfire to my soul. I can’t fight it, it’s overwhelming.” Tommy was choked up and fought off tears.

“You are a dear,” Juliana said and held Tommy tightly against her bosom. “I have such affection for you in such a short time. You’re an amazing boy.”

After a few minutes Tommy asked, “If I’m already a girl, then I want to be a girl who looks, acts, and feels feminine. How can I become that? What does being feminine feel like?”

“That’s like asking what masculine feels like. Feminine and masculine are words that describe stereotypes of women and men. We know what the stereotypes are so when I say I like to be feminine it means that I like to be like the stereotype. Do you understand what I’m saying?”

“Sort of.”

“For example, feminine is associated with lace, soft fabrics, perfume, dresses, skirts, stockings, high heels, jewelry, certain kinds of hair styles. Also feminine means being gentle, soft, smooth, curvy, delicate, demure. You get the idea?”

“Yeah.”

“When I feel feminine it means I closely identify with these things. I feel like that’s me.”

“A feminine boy will feel the same way?”

“I don’t see what the difference would be between a feminine girl and a feminine boy. Both see themselves as having the qualities I mentioned before. A feminine boy loves pretty lingerie and dresses. He likes perfume, he likes the things that are associated with feminine girls. He likes being gentle, soft, you know, all those things. Most important he sees himself as being feminine. While wearing girls clothes makes him feel feminine – it was feeling feminine that made him want to put on the clothes in the first place.

“I’m glad Trixie ran into your closet so we could have this discussion!” Tommy said.

Juliana laughed. “Part of growing up is figuring out yourself. What you desire. What you want to be. Why we want to be what we want to be is often a mystery. Sometimes people know why. Often they don’t.”

“If I’m a girl it means that …”

Juliana laughed. “It means that you want to dress pretty. You want to dress like a girl.”

“That’s true.”

“Can I be honest, Tommy?” Juliana said. “You’ve gone from zero to sixty in no seconds! Don’t you think you need to spend some time thinking about all that we’ve discussed? If your future happiness depends on dressing like a girl and feeling feminine, that’s great, but it’s not like you can do that without consequences. Not least of which is how your parents react to you.”

“You’re right, I’m being way too impulsive. Still …”

“Still what?”

“I’m not going to be able to stop thinking about wanting to be feminine. Besides that I don’t even know how to be feminine.”

“You do have a lot to learn, though I’m pretty confident that you’re not going to have to unlearn very many masculine traits in order to become more feminine.”

“What do you mean?”

“Just that as a boy you don’t come across as entirely masculine. You present to the world as a gentle boy – not exactly girlish but almost there. For example, you don’t have the muscles of typical boys. You couldn’t lift a carton that most boys would easily lift.”

“I’m sorry.”

“Why be sorry? I’m mentioning this because if you want to be feminine then you don’t have as far to go as you would if you had many deep masculine traits already cooked into your psyche.”

“Where does a boy go to learn how to be feminine?”

Juliana laughed. “I could teach you. The big problem though is that I don’t want to be seen as corrupting you. Your parents might get very angry if they found out that I was teaching you how to be feminine.”

“Do you think my parents would understand if I told them what I wanted to do?”

“I don’t know them very well, Tommy.”

“What about generally? Do parents ever understand that their son might want to be feminine?”

“My guess is that some do and some don’t.”

“Could you talk to them for me?” Tommy said.

Juliana laughed. “Me? Ask them if they mind if you want to dress like a girl?”

“I was thinking you could just say that I had said some things to you that made you think that I was interested in your lingerie. Feel them out.”

“Won’t they think I’m meddling in your family’s business?”

“You could tell them that I didn’t say you shouldn’t talk about it.”

“The next time I chat with your mom I’ll see if I can bring up the subject.”

“Thank you, Juliana,” Tommy said.

***

A few days later Cecilia happened to see Juliana sunning in the backyard and invited her over for tea. After chatting a while, Cecilia said that Tommy had become very fond of her. He loved looking after Trixie and talking to her. Juliana took that as a cue to say, “I’ve been meaning to tell you, Cecilia, that Tommy expressed some thoughts to me that suggest he’s working through some issues of his sexuality.”

“What sort of issues?”

“I’ve been going back and forth in my mind whether I should say something about this. I respect boundaries and don’t want to intrude. It’s just that you and Steve may want to keep your radar turned on to this part of Tommy’s teenage struggle.”

“Please feel free to talk to us. What specifically did he say?”

“As you and Steve know, I’m a feminine woman. That’s my thing. My clothes are feminine by choice besides the fact I need to wear these clothes for my job. Tommy was asking me about that part of me. How does one know if they want to be feminine or not? That kind of thing.”

“That’s interesting because Tommy asked Steve and I some questions about whether both boys and girls can be feminine. We didn’t think much of that at the time, but it could be related to what he said to you.”

“Yes, I’d guess they’re connected.”

“Steve and I will see if Tommy is willing to open up with us about his concerns. I won’t mention our conversation. I think it’s good that Tommy sees you as someone he can trust with his innermost thoughts. It reflects what a kind and sympathetic person you are.”

“You’re much too kind. I’m always available to help you and Steve with Tommy – if you need me to talk to him or listen to him.”

“Thanks. We’ll let you know.”

***

Later that day Juliana had a chance to see Tommy and she encouraged him to talk to his parents about his desire for femininity. “I spoke to your mom and she’s quite interested in finding out what kinds of issues you’re wrestling with as a teenager and especially your sexual identity.”

“She wasn’t freaked out?”

“Not at all. I don’t think your mom will freak out under any circumstances.”

“Well I guess I’ll try and talk to them. The truth is that every day I think about your bras and dresses and I know I want to wear them to help me feel feminine.”

“That’s okay, Tommy. It’s a good thing that you’re taking the time to allow yourself to get a clearer and clearer understanding of who you are and what you want.”

***

Cecilia briefed Steve on her conversation with Juliana and that night at dinnertime, Steve started a conversation with Tommy. “I remember that you were asking us about whether boys could be feminine.”

“Yeah, I remember.”

“I might as well be blunt and get right down to the nitty-gritty,” Steve said. “Are you a boy who wants to be feminine?”

Tommy began to weep.

“Dear, dear,” Cecilia said. “Your father isn’t scolding you!”

“I know, Mom,” Tommy said. “I’m just so afraid of disappointing you.”

“Disappointing us? How?”

“If I want to be feminine you’ll be disappointed in me!” Tommy resumed crying.

“Where did you ever get that idea?” Steve said.

“I just assumed that you wanted a normal boy.”

Steve laughed. “Tommy. This just means that you’re a normal boy who wants to be feminine. Nothing more nothing less.”

“It’s not just be feminine, it’s that I want to be a girl. I mean, I am a girl, I just want the chance to be a feminine girl.”

“Tommy,” Cecilia said. “Any boy who wants to be feminine probably sees himself as being a girl. Your father and I already understand that.”

“You do?”

“Yes, sweetheart. We love you and part of loving someone is that you accept them for who they are. It’s great that you’re struggling to figure out who you are. That’s a good thing because you’ve got a whole life ahead of you that you don’t want to live as someone you’re not. Your Dad and I certainly don’t want you to not spend all your days not being you!”

“You mean you don’t mind me dressing like a girl and being feminine?”

“No, we don’t mind, but before you go traipsing through the streets in girl’s clothes,” Cecilia said, “I should have a look at you – to make sure you’re as feminine as you can be.”

“Have you thought about how you’re going to become feminine?” Steve asked.

“I was going to ask Juliana to tell me what to do.”

“That’s a good idea,” Cecilia said, “since she’s the most feminine woman I know, but you’ll have to ask her if she’s willing.”

“Could you ask for me, Mom,” Tommy said. “I’m worried that she won’t believe that you’re allowing me to become feminine.”

“Sure, I’ll ask if she’s willing to teach you how to be feminine.”

***

The next day Cecilia rang Juliana’s bell and the two women sat down to chat. “We had a marvelous conversation with Tommy last night,” Cecilia said. “He confessed his desire to be feminine.”

“How brave of him! I must take off my hat to a young man with such courage!”

“Thank you.”

“It’s testimony to what fine parents you are that he was able to be open and honest with you.”

“Thank you, again. One thing Tommy asked me to do is ask if you’d be willing to teach him how to be feminine. Obviously, you’re a paragon to femininity!” Cecilia laughed.

“Yes, he does see me as a role model. I’m happy to show him how to be a girl, to be feminine. It’ll be a fun project for me.”

“It won’t take away from your work?”

“I’ll have to work it into my schedule.”

“Steve and I were thinking that in two months’ time he and I are planning on taking a two-week vacation to go scuba diving in the Maldives. Tommy hates that kind of physical sport so we were thinking that those two weeks he could work with you. When we come back Steve and I could see the result of your handiwork. Since it’s summertime Tommy won’t have anything else to do. What do you think?”

“That’s ideal, Cecilia! Two weeks should be enough time to get Tommy started on the path toward femininity. By waiting two months we can have him grow out his hair and nails so I’ll have a good basis to begin my work. It should be fun for Tommy and me.”

“Steve and I can’t thank you enough,” Cecilia said, “it solves such a big problem for us.”

“The pleasure is all mine,” Juliana said.

“You’re sure it’s not an inconvenience for you?”

“No, not at all.”

***

Later that day Cecilia and Steve sat down with Tommy and told him that Juliana had agreed to teach him how to be feminine.

“Oh, my God, Mom and Dad!” Tommy said. “I can get to be like Juliana. As feminine as her!”

Steve laughed. “That’s a very high bar, Tommy. My guess is that you can succeed in become feminine and even pass for a girl, but I’m sure it will take hard work.”

“I would never waste Juliana’s time so I’m sure I’m going to work very hard to follow everything she says.”

“That’s my boy! Err, I mean my girl? My whatever!” Steve said.

***

Tommy was excited to thank Juliana for her willingness to give him lessons on becoming feminine.

“I’m happy to help. I think it’ll be an interesting adventure that you and I can take together. At the end of it I hope you’ll be as much a girl as I am!”

“That’ll be impossible!” Tommy said. “You’re so beautiful and feminine!”

“We’re going to make you beautiful too!”

“Mom and Dad said we can begin in a couple of months. You’d like me to grow out my hair and fingernails?”

“Yes. Your hair is about three inches now. In two months it’ll be four to five inches – about long enough for a pixie cut and almost a bob cut. By the fall you’ll have a very sweet bob cut and by Christmas it’ll just be touching your shoulders. That’ll give you a chance to explore many different hairstyles. As far as your fingernails go, I’ll show you how to file them so that they are shapely. A month before we begin you’ll let them grow fully and maintain their shape. They’ll be a good length to get you used to having long fingernails. We’ll be able to hit the ground running when we begin our experiment!”

“I can hardly wait,” Tommy said.

***

Two months later Juliana joined Tommy in saying goodbye to Steve and Cecilia when an Uber came to take them to the airport. “He’s in good hands,” Juliana said.

“We’re sure of that,” Steve said, “and we can’t thank you enough!”

“I love you!” Tommy said. As his parents departed down the block it came to Tommy that they might never see him again as a boy. It was a sobering thought but was soon overwhelmed by the excitement he felt about Juliana teaching him how to be a girl.

“We should get to work,” Juliana said, “there’s so much to cover! I’d like you to stay with me during the two weeks so I can monitor your behavior at all times. The only way you’ll be successful is by systematically eliminating the slip-ups that you’re bound to have. We’ll make this like learning a new language by total immersion. That’s the fastest way to become fluent. We need to get you fluent in femininity in two weeks’ time!”

“Where do we start?”

“Let me look at your fingernails,” Juliana said.

She took Tommy’s hand and examined it. “Very nice length. I’m glad they’ve grown out. And your hair also. So first stop is my stylist who’ll get you a bob style. The nail technician will get you pretty nails. With those things accomplished we’ll be in a good position to begin talking about bras and panties.”

***

When Tommy sat down with the stylist, Bonnie, Juliana described what she was looking for.

“It’s doable,” Bonnie said. “Tommy’s hair is just long enough and it’ll be plenty long in a month or two.”

She set about styling and cutting his hair. “Juliana says you’re wanting to become a girl?” Bonnie said.

“Yeah. This week and next she’s going to teach me how to be a girl. Femininize me. I’m so excited. The beauty parlor is the very first step!”

“I’m honored to assist you! I think you’re going to make a very pretty girl.”

“Thank you,” Tommy said.

Bonnie laughed “Welcome to the sisterhood!”

“I’m so lucky that Juliana is willing to help me.”

“She’s a female’s female, that’s for sure. If anyone can feminize you it’s her. Have you always wanted to be a girl?”

“I think so, but I just didn’t know how to form it into a specific desire. Juliana was the catalyst. I realized that more than anything I want to be like her. Dress like her, act like her. She’s like a hero to me!”

“That’s so sweet, Tommy. I hope you succeed. I’ll be very excited to see you again in a few months when you’re ready for your next haircut!”

After Bonnie, Juliana took Tommy to a shop where he had his finger and toenails done. Tommy was overwhelmed by the number of color choices. Juliana steered Tommy to a basic pink color that would look good with whatever outfits he would end up wearing.

Before they exited the shop Juliana said, “Take a good long look at your hands.”

Tommy stared at them and admired the long pink nails.

“From now on you have girl hands. That’s very important to remember. Girls move their hands more gracefully than boys do. They hold things more delicately – certainly to help make sure they don’t break a nail. You have to now always be conscious of your girl hands and how you use them.”

“I’ll try really hard. Do you think that eventually my hands will automatically behave like girl hands?”

“Yes, Tommy. With everything I teach you, at some point you’ll sublimate it into your psyche and you’ll begin doing it instinctively. At least, that’s my hope. By the time your parents come home you should be well on your way toward behaving, moving, acting, thinking, and looking like a girl. With each passing week and month all these things will become further ingrained within you.”

“Wow!”

Juliana laughed. “It’s a daunting transformation you’re embarking on – but the happiness you’ll get being a girl will more than compensate for all your effort and frustration.”

***

When they returned to Juliana’s house, they sat down together and Juliana showed Tommy how she moved her hands. Each womanly gesture she made with her hands she had Tommy imitate. When he started getting familiar with hand motions she said, “Hand motions go with arm motions so it’s appropriate that these be learned together.”

It became plainly obvious to Tommy that he was going to need to relearn how to move his arms and hands if he was to be feminine. Juliana had him hold out his forearms and bend his hands to hang limply or to bend them up – either position creating a distinctive feminine gesture.

“You must remember to be feminine all the time. No falling back to your customary boy traits.”

“I’ll definitely try and do that!”

“If all goes well you’ll reach a point where you won’t know how to hold your hands like a boy even if you wanted to.”

“Wow, that’s neat. I can’t wait for that to happen.”

“Now I’ll show you how a girl grasps at and picks up things. She’s of course concerned about her nails, but her fingers automatically compensate for the presence of long fingernails. In other words, her long, polished nails are such an ingrained part of her that her hand motions have permanently adapted to them.”

“Cool.”

“Watch this and then you do it.” Juliana said. “I’ll pick up a vase and examine it.”

Beginning with her hands hanging limply down she reached out and gracefully cradled a small vase in her hand in such a way that her nails never touched the surface. She passed the vase from one hand to the other and put it back down.

“Now you do it.”

Tommy imitated Juliana as best he could. What she had suggested about his long nails was true. He had to purposefully avoid scratching the vase with his nails. It required moving his fingers and hand differently than he was used to.

“Good Tommy. You’ll need to practice this a thousand times until its second nature. Besides learning your girl motions, also think about avoiding your boy motions. Make an effort to tell yourself not to move like a boy does. It’ll then be like a push and pull toward femininity.”

“I understand.”

“You have to learn that the way that girls move their arms and hands is reflected in how they do all that they do. Especially getting dressed, which obviously involves holding clothing and manipulating it in such a way as to get it onto your body. You don’t want your fingernails getting caught in the delicate fabrics.”

“I had no idea,” Tommy said.

“A good starting point is to train you in how to put on your bra and panty. It’s what girls do every morning. It’s what you’re going to have to do every morning for the rest of your life.”

“How do I know which bra and panty I want to wear on a given day. I mean look at how many bras and panties you have!”

Juliana laughed. “You’re right, but I have so many because of my work. A typical woman will have a much smaller collection. She’ll have her everyday bras that she probably picks for comfort. Then she might have some special sexy bras – like most of mine – for times that she wants to be alluring. She might also have some specialty bras for strapless gowns. Also some sports bras. You’ll have to do some experimentation to see what kinds of bras you prefer.”

Yet another fun thing about being a girl Tommy thought. You get to create your own personalized collection of bras. How neat was that! “I’ll want my bras to be like yours.”

“That doesn’t surprise me. One thing you’re going to have to figure out is what size bra you should wear. That depends on your breast size.”

“I can have any size I want?”

“Yes. You might say that one advantage that you have compared to girls who are born as girls, is that your chest is a tabula rasa that can take any breast size you desire. Since for now you’ll be wearing my bras I suggest that you have breasts the same size as mine. What do you think?”

“That’s a great idea. How big are your breasts?”

“They’re DD cup which is quite a nice sized breast. Since you and I are roughly similar in body size that could be a good cup size for you too.”

“How do I get DD sized breasts?”

“I have some that I obtained previously in anticipation of this moment. I’ll attach them to you. First we both need to get naked!”

“Naked?”

“Yes. We’ll act out together what a girl goes through when she wakes up in the morning and puts on her bra and panties. You imitate everything that I do. Before that I need to affix your breasts to your chest and get you set up in a gaff.”

“A gaff?”

“That’ll be effective in hiding your penis. It provides a snug, secure compression so that no one will know that you have a penis. You’ll see. Trust me.”

Tommy stared at Juliana.

“Am I making you uncomfortable?” Juliana asked.

“No, it’s okay.”

“If you’re going to become a girl, you have to understand that there are many circumstances where girls can be naked with each other. Locker rooms, dressing rooms.”

“Sure, I see what you mean.”

“Good. So we’ll both take our clothes off.”

Juliana reached behind her back and undid the zipper on her dress. She stepped out of it and carefully hung it up. She had a slip on underneath and Tommy turned away from her to take off his pants and boxers and lift his shirt off over his head. When he turned back to look at Juliana he had to gulp in surprise. In full display were her remarkable breasts, perfect skin, narrow waist, beautifully curving rear end and an amazing hairless slit where her legs came together. Juliana saw the expression on his face and smiled.

“I take it you’ve never been in the presence of a naked woman before, have you?”

Tommy shook his head. The view of Juliana was shooting pleasure signals down to his penis and it began to rise up.

“This is what a woman looks like,” Juliana said laughing. “And I can see that your penis understands that.”

“I’m terribly sorry,” Tommy said.

“Nothing to be sorry about. You can want to be feminine and still see girls sexually. It’s just who you are and we’ll have to work around it. That’s one reason why the gaff is necessary.”

“I don’t want to be a problem for you.”

“You’re not a problem, and besides, we’re not going to give up so easily! So step into the gaff and we’ll pull it up your legs.” With Juliana’s help in organizing it, Tommy got the gaff up to his mid thighs. “Now let me get it on you correctly.”

Tommy thought he might explode as Juliana carefully and delicately reoriented Tommy’s penis to point backwards and fit into the gaff. It was a bit of a struggle and Juliana said, “After your little guy calms down, it’ll snap into place.”

“Okay,” Tommy said, doing his best not to allow the pleasurable feelings to escalate.

“Actually,” Juliana said, “if you masturbate you could probably have an easier time with the gaff. A much easier time. What do you want to do?”

Tommy was speechless. This was all going into territory that he had no understanding of. “Yeah, I guess I need to get rid of my boner.”

“Go in the bathroom and I’ll wait for you.”

Tommy did as she said. In exactly forty-five seconds his penis jerked out its effluent into the sink. He cleaned up and returned to Juliana.

“Wow, that was fast!” Juliana said.

“I know,” Tommy said. All he had to do was envision Juliana’s breasts in his mind’s eye and he exploded in orgasm.

“Your penis is now much more manageable,” Juliana said, as she tucked it carefully into his gaff. Very good Tommy. How does it feel?”

“Comfortable,” Tommy said, looking down at himself and then in the mirror. “It really hides my penis.”

“Anyone would think you have a vagina like I do,” Juliana said.

“Cool,” Tommy said. This was getting better and better with each passing moment.

“Okay, now before we do our panties and bras, I’ll attach your breasts.”

“How do you do that?”

“I’ll show you. I’ve bought silicone breast forms.” Juliana opened one of two boxes and showed Tommy the breast form within. She picked it up and expertly attached it to Tommy’s chest using glue that she had prepared ahead of time. Then she carefully attached the second breast. “I’ve matched your skin color very well. A little makeup on the edges and you look like you have real breasts. You can keep this on for some time until we have to reattach them. How does it feel to have breasts?”

Tommy stared at himself in the mirror with his jaw hanging down. Next to his image Juliana appeared. His breasts were almost identical to hers.. His nipples were a bit more erect than hers. The areolas were the same size and color. Looking down Tommy saw the swell of Juliana’s beautiful hips. His own weren’t as full as hers.

“I don’t know what to say, Juliana. You’re already a miracle worker!”

“You’ve got pretty, smooth skin Tommy. Nary a body hair. None on your chest or legs. You don’t even shave yet, do you?”

“I have pubic hair,” Tommy said.

Juliana laughed. “I know that, silly! You’re definitely on the girl side of the boy spectrum. The breast forms look so good on you because your chest – apart from not having breasts – is very much like a girl’s chest. And look at your thin arms. Can you do pull-ups?”

“One or two. Maybe. I can hang from the bar,” Tommy laughed.

“So I think we can say that you’re an especially fine candidate for femininization. I bet you’re on the low end of the testosterone spectrum.”

“Really?”

“That explains your soft skin and absence of body hair. And muscles!”

“This is so nice,” Tommy said. “You’re the kindest person ever …” Tommy got choked up and had to stop talking.

“Aww, Tommy. Look at us. We’re two lovely girls!” Juliana laughed.

“Still, you’re the truly beautiful one.”

“You probably don’t realize that there are many things that you can do when you’re an adult to push your transformation further along.”

“Like what?”

“You can get breasts inserted in your chest. You might also get your tush enhanced. It’s also in the realm of possibility when you’re older and self-assured that you might want to transform your penis into a vagina.”

“They can do that?”

“Yes. It’s non-trivial and there are risks that you have to understand. That’s all in the future. For right now, for our two weeks together you and I have very similar bodies that we can dress in the prettiest clothes. We can be two girls together. We can wear our pretty dresses together and otherwise express our femininity.”

“I know I’m going to love that!”

“Whenever you’re with girls you should try to imitate what they do. That way you’ll acquire many of the slight female nuances that you might otherwise not be aware of.”

“This is so exciting.”

“I’m glad you said that. I don’t want any doubts floating around in your mind about your transformation. You’re all in!”

“Yes, Juliana. There’s no doubt about that. I’m all in!”

“Good, so let’s get ourselves into our panties and bras. Imagine we’ve woken up. What’s the first thing a girl does when she wakes up in the morning?”

Tommy looked blankly at Juliana.

“She pees, silly!”

Tommy laughed.

“What’s more she pees sitting down. From now on you can only pee sitting down. Got it?”

“Yes Juliana.”

“And when a girl is done peeing she takes a couple of squares of toilet paper and she dabs it over her vagina.”

“Right!”

“If she’s having her period, she’s likely to change her tampon or pad right after she’s done peeing.”

“You have periods?”

Juliana laughed. “Of course I do!”

“Do you use pads or tampons?”

“Both. Usually tampons but every so often I put on a pad. Sometimes for overnight if I’m having a heavy flow. I might even have to change my pad in the middle of the night.”

“I didn’t know any of that. I’ve heard that periods can cause girls cramps that hurt.”

“Very true. It varies from period to period and girl to girl. It’s something that all girls know about and so you have to know about it too. In fact, you should have a pretend period every month. My period is coming next week. How about you wear a pad during the time that I’m having my period.”

“Sure that’s great. Maybe I’ll get some sympathy cramps,” Tommy said.

“How cute is that, Tommy. I’m glad that you want to feel everything that girls feel.”

“After we pee then what do we do?”

“You pick out the panty and bra you want to wear for the day. You’ll have to pick from among my bras and panties until we can get you your own collection. Your Mom will have to take you shopping for bras and panties and everything else you need to be a girl.”

“I thought that maybe you’d go with me.”

“Yes, we could have fun shopping together but it’s really a nice time for you and your mom to bond as mother and daughter. She’ll enjoy helping you select underwear and dresses. I wouldn’t want to take that pleasure away from her!”

“I see what you’re saying. Yes, I’ll ask my mom to go with me.”

“That’s the spirit. Your transformation has many different consequences. Your friends and family will have to react to your changes; besides the fact you’ll meet new people.”

“I think I’m falling in love with you Juliana!” Tommy said. “Is that bad?”

Juliana laughed. “Girls can love each other – I’m not talking sexually which is of course possible. – but rather as two gentle souls who want to support each other girl to girl.”

“So you might love me that way?”

“I already do, Tommy. I think we’re two girls,” Juliana laughed, “or a woman and a girl! – who love each other and will love each other more and more with each passing day.”

Tommy’s eyes filled with tears and Juliana hugged him. Their breasts pushed against each other’s.

“So let’s choose our bras and panties!” Juliana said and they entered her lingerie closet.

“I don’t know where to begin!” Tommy said as he composed himself.

“How about we narrow it down? First tell me what color you’d like?”

“Pink!”

“Then I’ll take blue!” Juliana said.

“I didn’t take your color, did I?”

Juliana laughed, “I can wear pink any day I want. Today I want to put you on center stage. I want to make you as pretty as I can and train you as best I can to be a girl. Pink certainly is the best color to start with!”

Tommy gazed at the pink bras and panties and picked a matched set. “I like these!”

“Very nice choice. That’s always been one of my favorite sets. The lace and sweet little roses combine for a super feminine look. I’ll wear this pretty blue set.” Juliana said. “Now we put on our panties. I’ll go first and then you imitate me.”

Tommy watched Juliana step into her panties and pull them up to her waist. Tommy then prepared to step into his pink panties.

Juliana halted him saying, “Tommy! Remember that the panty is delicate and must be held carefully. You’ve got to exorcize that male tendency to grab things in favor of the feminine approach I demonstrated. Let your fingers caress the soft fabric and lace. Women take pleasure in softness, so allow yourself to really feel the panty. Watch how I take the panty from you.” Juliana gracefully took the panty into her hand making clear how she respected the delicacy of the fabric.

“I see what you’re saying.”

“Good. Here’s the panty, Tommy.”

Juliana held the panty out for Tommy and he made a great effort to treat it as gently as he could.

“Very good. I like your limp wrist – the same as the way I was holding the panty. Girls don’t have their muscles all engaged and taut like boys do. Boys are put together like an erector set. Girls are fluid and graceful. We avoid harshness. As I said, we must compensate for our long fingernails.”

Tommy finished putting on the panties.

“That’s better. You’ll need some practice but I think that you do understand the concept of how girls hold things differently than boys. Also, as you step into the panty, remember to lift your knees forward as you get your feet into the leg holes. Women avoid keeping their legs apart. They don’t like exposing their vaginas to the world.”

“I should always think about protecting my vagina?” Tommy asked.

“Yes, that’s a good way to think about it.”

Tommy marveled at the panty he was wearing and said, “The panty feels very good on me.”

“It’s nice that you and I are the same size. This particular panty is what is called a brief. It has full coverage of our tushies.”

“Neat. There are other kinds of panties?”

“For sure. There are thongs, hipsters, bikinis, and boy shorts.”

“You have all these kinds here?”

“Yes. Panties are at the center of a girl’s body – and the first line of defense against anything going in or out of our vaginas. It’s a good idea to keep one’s vagina covered.”

“Like when a girl has her period?”

“Yes, for sure.”

Juliana had to admit to herself that Tommy looked cute in the panty.

“It’s time we got those big breasts of yours into a bra. I’ll put mine on and then you imitate what I do. Watch very carefully.”

Tommy fixed his gaze on Juliana’s bra and watched as she clipped it, swiveled it, and pulled it up to capture her breasts. Once her breasts were safely in her bra he noted with fascination how she made small tweaks to their position until she was satisfied that her bra was fitting comfortably.

“Now you try it!”

Tommy made a point of holding his bra with feminine gestures. He held the ends and looked down past his breasts to clip the ends taking care that his fingernails didn’t scratch the bra. Once he had it clipped he swiveled it around gently. With the cups just below his breasts he delicately lifted the bra and fitted his hands within the straps the same way he had seen Juliana do it. In the penultimate step he hiked up the bra so that his breasts nestled into the cups. Then he attempted to do the same smoothing gestures that he had seen Juliana do.

“Oh my God, Tommy,” Juliana said. “You’ve done a fabulous job of putting on your bra. You copied everything I did. Congratulations!”

“Thank you,” Tommy said, overcome with emotion from the realization that he was now wearing a bra and panty the way girls did. He looked into the mirror standing next to Juliana. This was the happiest day of his life. The only way he could be happier would be when Juliana had him fully dressed. The anticipation of seeing himself wearing one of her pretty dresses caused his heart to race.

“I think you’re really getting into a groove now Tommy. I didn’t have to remind you to have feminine gestures while putting on your bra. Keep practicing exactly this way and you’ll develop into a perfectly feminine boy or even girl if that’s what you want one day.”

“Thank you, Juliana. What do we put on next?”

“Next is our hose, our stockings or pantyhose. I’ll let you decide what we wear.”

“Between pantyhose or stockings?”

“Yes.”

“Don’t the stockings have to be held up?”

“Yes, I’m sorry, Tommy. When a girl wears stockings she often needs to wear either a garter belt or a girdle to hold them up. You look a little confused. Let me show you.” Juliana found a garter belt and held it up for Tommy to see. “This is a garter belt. It goes around your waist and the garters attach to your stockings to hold them up.”

“Do you like garter belts?”

“Yes, I do, but I also like girdles.”

“I think my mom wears girdles,” Tommy said.

“Does she?”

“I’ve seen her folding laundry and she had some girdles that had been washed. I’ve also seen them on the drying rack.”’

“They have attached garters?”

“I think so.”

“Girdles are either panty girdles such as this one,” Juliana said, holding up a white panty girdle, “or an open bottom girdle, like this one.” She held up a pink, open bottom girdle.

“Gosh, there are so many choices.”

“Four choices. Pantyhose, garter belt, panty girdle, or open bottom girdle. Which do you prefer?”

“Which one do you like?”

“Tommy. Remember. You’re a girl getting up in the morning and getting dressed for the day. You know you’ll be wearing hose so you have to make a choice.”

“I’ll wear the pink girdle,” Tommy said.

“Okay. I’ve got a blue open-bottom girdle that I’ll wear. I’ll slip it on and then you imitate me.”

Juliana put on the blue girdle and then Tommy put his girdle on. Once again Tommy was amazed. “I can’t believe how nice the girdle feels. Some compression in my tummy but I love the support it gives to my tushy and thighs.”

“It’s true that a well-fitting girdle makes a girl feel together – whole and ready for anything!”

“I’m beginning to feel that way, Juliana.”

“That’s grand! Now we put on our stockings.” Juliana showed Tommy how to carefully hold the stockings. “Note how I hold my fingers in such a way as to not touch the fabric. If your stockings get snagged on your nails you’ll have a run in your stocking and have to discard it. That can be ten dollars or more down the drain.”

“I promise to be doubly careful when I put on my stockings!” Tommy said.

“I know you will,” Juliana said.

She expertly put her stockings on and then attached them to the garters. She made it seem effortless, but when Tommy began to imitate her he ran into trouble at every turn.

“This is so hard!” Tommy said. “I’m trying to delicately roll my stocking up so I can put my toes in it but I feel like my nails are in the way!”

“This is one of those skills that separates women from men or girls from boys. You have to summon every fiber of your girlish self to master it!” Juliana laughed. “I’m teasing you Tommy. It’s sometimes hard for girls to get their stockings on without mishap. With some experience you’ll get better and better.”

“Yay, I got my foot in the stocking!” Tommy said. “Now I have to gently roll it up my leg.” He slowly brought the top of the stocking to his thigh. “Whew! Success!”

“Now attach your stocking to the two garters on the girdle. It’s important to align the garters correctly. That’s why it helps to attach them while standing up. Now go ahead and do it.”

Tommy fumbled with the front garter and got it ready. Then he maneuvered the top of the stocking and fastened the garter to it. By bending over he was able to fasten the second garter.

“Very good, Tommy!” Juliana said.

“So cool!” Tommy said. “I’ve got one of my stockings on!”

“You are adorable,” Juliana said. “Only a girl at heart would feel such a wonderful sense of accomplishment in putting on their stockings.”

Juliana’s words had the effect of allowing Tommy to see that there was a difference between wearing stockings because he liked pretending he was a girl and wearing stockings because he was a girl. It landed on him like a ton of bricks that he wanted to wear stockings because he was a girl – a feminine girl – who liked to wear stockings. Tommy as he had previously thought of himself was being exorcised from his body by leaps and bounds. Tommy the boy would soon be no more.

Tommy put on the other stocking thinking throughout that he was a girl getting ready for her day. When he was done, Juliana and he stared together into the mirror. Tommy was wearing a more or less pink version of the blue underwear that Juliana was wearing.

“I love how your transformation is going,” Juliana said. “Just a few hours and I’m already seeing the girl emerge in you and take a dominant position. She’s a very determined young lady!”

Tommy laughed. “I feel like Tommy won’t end up being my name.”

“That’s true. What would be a good girl’s name for you?”

“I wish I could also be Juliana.”

“That’s so sweet but you need to have your own identity.”

“I could let my mom and dad decide what girl’s name they want to give me.”

“That’s a great idea. In the meantime I think we can call you Tammy if we have to give you a girl’s name.”

“I like that. Tammy!”

“Now, Tammy, let’s get you into a dress!”

Juliana and Tommy entered the dress closet. Tommy was overwhelmed gazing at the many dresses. Everyone he looked at he wanted to wear.

“I know you want to wear a pink dress,” Juliana said, “so let’s concentrate on picking one of them for you to wear. Do you see one in particular that you’d like?”

“What about that one?” Tommy asked.

“You’ve got a good eye for the prettiest dresses! That one has a sweetheart see-through corset and a fluffy A-line skirt. It’s light and crisp and perfectly outlines the body. It’s worn with a short, pink crinoline. A great choice. Now I have to pick a blue dress. I’ll take one similar to yours. Both our dresses have sequins and some 3D flowers attached.” Juliana found the short blue dress she was looking for. She and Tommy held up their dresses side by side. “So perfect!” Juliana said.

Tommy followed Juliana to the adjoining closet filled with crinolines. She selected a short pink crinoline for Tommy and a short, pale blue one for herself.

Juliana put the dress on over her head and had Tommy help her zip it up. Then she stepped into the crinoline and moved it up to her hips underneath the dress.

“Now your turn,” Juliana said.

Tommy did a credible job of imitating Juliana. When she zipped him into the dress and he had put on his pink crinoline he excitedly rushed to the mirror to have a look at himself.

“You have to admit that you’re precious, Tommy,” Juliana said. “What a cute girl you are. You belong in that cute dress. It’s hard to believe that you ever thought you were a boy. I’m not even going to ever talk to you again as if you’re Tommy the neighbor boy who cuts the grass. No, absolutely not. You’re now Tammy, the sweet girl who lives next door and is every bit as pretty as I am!”

Tommy laughed uproariously. Everything Juliana said was true. Unless his mom wanted to call him something else, he’d be happy to be Tammy. When his parents came back from their trip they would only see pretty Tammy wearing her pretty dresses. Never again would Tammy be even remotely like the boy Tommy they once knew.

“The last two things are our heels and a bit of makeup. You’ll need to wear pink heels.” Juliana looked among her shoes and pulled out a pair of pink, patent, leather heels. “Try these on for size.”

Tommy gracefully sat down keeping his legs together the way Juliana had instructed him. He slipped one foot and then the other in the heels and stood up.

“How do they feel, Tommy?” Juliana asked.

“Good, I feel wobbly but they aren’t uncomfortable.”

“These are my sexiest pink heels so I’m glad you fit in them. I’ll pick some heels for myself.”

When they were fully dressed Juliana said, “Hold onto my arm and we’ll walk around a bit to help you get used to the heels. Tommy stood up and immediately was steadied by Juliana. She led him in small steps across the room.

“This is so much fun,” Tommy said.

“You’re legs are feminine and combined with the short, fluffy skirt, and large chest you are a seductress!”

After a few minutes Juliana let go of Tommy and he walked a bit unsteadily around the room.

“Pretend you’re a ballerina on stage,” Juliana said. “Stand erect and elegant. Now make each step as if you’re playing the part of a queen!”

Tommy took her advice to heart and his movements improved to the point that Juliana applauded his effort. “I’m sure that you were born with a talent for wearing high heels. Some women perpetually struggle to walk comfortably in them, but you truly have all the grace that a woman could hope for.”

“I do?”

“Indeed! Now let’s apply a wee bit of makeup – some rouge and lipstick – and then you’re complete! Well, almost. We need to get your ears pierced. Do you think that’ll be okay with your parents?”

“I don’t know, but I’d hate to miss out on that.”

“Let’s be bold and take a chance! Of course, if you don’t wear earrings the holes will close and you’ll be no worse for wear.”

“When should we go?”

“Maybe tomorrow.”

“Won’t I need more practice in the heels?”

“We can wait a couple days. In the interim you can practice being a perfect girl. Remember that the fastest way to learn anything is to dive in and figure it out. That’s why I think you’ll become a girl faster by going out into the world even before you think you’re ready. It’s the difference between rehearsals and actually giving a concert. In a couple of days I’ll take you to the mall and we’ll get your ears pierced. I’m also happy to buy you a couple of your own bras.”

“Really? Thank you so much!”

***

The morning of their trip to the mall Tommy vacillated between confidence that he behaved exactly like a girl to moments where he felt like he had so much more to learn. Juliana told him not to worry. It’s normal to feel nervous before such a major event.

“Keep it simple today for the mall. Pantyhose and I’ll help you select a skirt and blouse,” Juliana said.

Tommy went to the lingerie closet and selected a bra and panty to wear and took a pair of pantyhose. He put on the panties and bra and then visited Juliana as she was getting dressed to get pointers on how to put on the pantyhose, which he had not yet worn up to this point.

“Sure I’m happy to demonstrate how I put on my pantyhose,” Juliana said.

She sat on the edge of the bed wearing panties and a bra and showed Tommy how to line up the legs of the pantyhose, roll up one leg, put it over the toes and unroll it to her knee. Then roll up the other leg and put it on up to her knee. Then she stood and pulled the pantyhose up to her waist and finally did a little two step dance to get the pantyhose fully on.

Tommy did his best to imitate her. With his long nails it was no easy task to avoid scratching the delicate fabric. Eventually he got them on without mishap.

“Look at me! Look at me!” he said running to Juliana.

“My what a big girl you are now, Tommy! You can put on your own pantyhose.”

“And my bra and panties!”

“True!”

***

At the mall Juliana said, “Morrison’s Jewelry is the best place to get your ears pierced. The staff is well trained and they sterilize everything.”

Juliana selected gold studs for him to wear. A young salesgirl with Juliana’s guidance marked the locations on Tommy’s ear lobes where he’d be pierced. She held up a mirror to show Tommy and he nodded in agreement.

“She’s going to pierce you now and put the studs in,” Juliana said. “You can close your eyes if you’re squeamish. She’ll use a hollow-bore needle.”

Tommy closed his eyes and scrunched up his face. Within a couple of minutes the girl was done with the piercings and was applying alcohol to them.

“Remember to clean them with alcohol. Rotate them. In six to eight weeks you’ll be able to take out the studs and wear whatever earrings you’d like!”

“Thank you,” Tommy said.

The salesgirl held up the mirror and Tommy looked at the studs. It was one step further on his way to being a girl.

“Did you notice that the salesgirl saw you as a girl,” Juliana said as they left the shop.

“I thought that she was just being kind.”

“No. She had no clue you were a boy. I’ve been watching you since we left the house. You’re making a very convincing effort to be feminine.”

“I guess I’m extra self-conscious which continually reminds me to focus on my new mannerisms.”

“Well, whatever you’re doing, it’s quite effective. Imagine how feminine you’ll be by the time your parents return!”

“I hope I’m a real girl by then!”

“You are a real girl in my opinion. Just imagine. A girl like me was raised by my parents to be a girl. From the youngest age I was expected to be feminine and to act and move and think like a girl. You were raised to be masculine. To act and move and think like you are a boy. Despite all of that boy indoctrination – in which your true girl identity was buried – you still dug yourself out and have become a girl. Doesn’t that prove that deep down you are most definitely a girl.”

“When you put it like that …”

“That is how I put it! Our next stop is a cute lingerie shop at the end of the mall. Well, before that let’s get some lunch.”

As they walked through the crowded mall, Tommy’s eyes took in the women and girls that he passed. He was curious about the clothes they were wearing, about their footwear, jewelry, hairstyles, makeup. Where in the past he was jealous of them in a way – even if he never articulated it – now he saw that he was one of them and there was no cause for envy.

As Juliana and Tommy passed a group of boys outside Dave and Buster, Tommy noticed them checking him out as well as Juliana. If boys saw him as sexy enough to stare at then he must seem like a girl to them. Tommy now turned his attention to the boys they passed. Many of them snuck glances at him as he passed by them.

“I see boys glancing at me as we walk past them,” Tommy said.

“You’ll get used to that,” Juliana said. “Look carefully and see where their looking.”

A few minutes later Tommy said, “They look at my face but then their eyes fall down to my chest and stay there.”

Juliana laughed. “Bingo! Now you know that boys look at our boobs. They can’t not check out the size of our chests. When a girl gets to DD as you and I are we can expect quite a bit of attention. Men want to look at our breasts, hold our breasts, suck on them. It can be annoying but we can also become so accommodated to it – like I am - that we don’t give it a second thought.”

Tommy knew that he had a long way to go before he became oblivious to men staring at his chest. In fact, he took frequent looks at it himself – it was such a lovely new feeling to be wearing a bra holding up ones large breasts. He especially loved the way his breasts swayed within his bra as he walked.

“Do you have a boyfriend?” Tommy asked Juliana.

“Not a steady one. I date several men but I have yet to meet the man of my dreams.”

“What will he be like?”

“I’d like a man who appreciates my pretty clothes. A man who enjoys them as much as I do. A man who likes talking about my clothes. If I get a new bra and there’s something really interesting about it – say how the cups are sewn together, or a new fabric or lace – then I’d want my boyfriend to be as excited as I may be.”

“I’m pretty sure that I care as much as you do about bras – of course I don’t know very much yet about them but I want to know everything.”

“Yes exactly, Tommy. Meeting you and discovering your love of lingerie and pretty dresses has given me encouragement that I might really be able to find the kind of man I’m looking for.”

“It’s too bad I’m too young for you, Juliana!”

“I know!” Juliana said and laughed.

Tommy knew he loved her. He would do anything to be her boyfriend. They could have so much fun dressing up together.

They came up to a small restaurant and Juliana said, “This is my favorite place for lunch. Let’s eat here.”

Upon entering the luncheonette Juliana ran into her friend Ximena with her daughter Maria.

“Fancy meeting you here!” Ximena said.

“Small world! Ximena and Maria,” Juliana said, “this is my neighbor’s daughter Tammy.” She looked at Tommy and winked her eye.

“Nice to meet you,” Tommy said.

“Likewise,” Ximena said. “We’re bra shopping at the department store. Maria is moving beyond a C cup; can you believe it?”

“Mom!” Maria said. “You’re embarrassing me!”

Tommy laughed and said, “I’m sorry.”

“It’s all right. My mom is so proud of my bra size she has to tell everyone!”

“You know that you’ve been hoping for this day for a long time. Getting to D cup has been your obsession!”

“I think you need to announce it to everyone at the mall. We could have a party to celebrate my D cup breasts and my new D cup bras!” Maria said.

Tommy laughed again. Maria said, “What bra size do you wear?”

“I’m DD,” Tommy said.

“Cool. You’re lucky. I don’t think I’ll go beyond D,” Maria said.

“I’ve told you a thousand times, Maria, that you won’t be done growing your breasts until your eighteen. You’ve got plenty of time to get to DD. Of course if you ever have babies your D will swell to a DD for sure.”

“And it may never come down again,” Juliana said.

“Right,” Ximena said. “What are you and Tammy doing at the mall?”

“Tammy just got her ears pierced,” Juliana said. “We’re also going to look at bras. See what they have. But not at the department store. There’s a small boutique that I prefer.”

“Don’t they charge more?” Ximena asked.

“True, but their bras, really all their lingerie, are so much prettier than what you’ll find in the department store.”

“Oh my God, Mom.” Maria said. “Can I go with Juliana and Tammy to buy a bra!”

“The boutique is on the other end of the mall,” Ximena said.

“How about I take the two girls to the boutique and you can have a coffee at the Starbucks.”

“You don’t mind?”

“Not at all,” Juliana said. “I love bra shopping and I especially love to help girls pick out the bras of their dreams.”

“Okay. I’ll give Maria my credit card. Maria, don’t go crazy!”

“I won’t let her!”

“Just two bras, Maria. That’s all.”

“Thank you Mom,” Maria said.

“First we need to have lunch!” Juliana said.

“Let’s get a table.” Ximena said.

Tommy sat down next to Maria for lunch. “What kind of bras do you like?” Tommy asked Maria.

“My number one rule in bra shopping is that I always take the prettiest bra I can find,” Maria said. “If it doesn’t have lace then I won’t look at it. Most of my bras are pink but not every one. What about you?”

“I’m the same way,” Tommy said. “I love pink bras.”

“That’s so cool. I don’t meet very many girls who are excited about pink bras!”

“A lot of girls don’t have a passion to be feminine like we do,” Tommy said.

“That is so true. I’ve always loved girlie things,” Maria said. “My mom thinks I’m crazy but it’s just the way I am.”

“Juliana has the prettiest clothes possible,” Tommy said.

“I know,” Maria said. “So many times I’ve been jealous of the dresses she wears.”

“She loves being feminine. My mom doesn’t really care so Juliana is taking me to get pretty bras.”

“That’s so cute,” Maria said. “I could use help like that.”

“I’m sure Juliana will have good advice for both of us in the boutique.”

After a pause, Maria asked, “Do you have a boyfriend?”

“No, I don’t. Do you?”

“Yes. We’ve been going together for a few months. His name is Todd. He’s got a friend Dan who’s pretty nice. Kind of shy but handsome. He hasn’t dated much. I think he’d go for you. Both Todd and Dan like feminine girls.”

“I haven’t dated much.”

“Then you and Dan are a good fit! I know this is sudden but to be honest I don’t know any girls as feminine as we are. Todd’s been feeling bad about Dan not meeting any girls so I think its providential that I’ve met you. You should be exactly the kind of pretty girl that Dan would like. If he’s like Todd, then Dan loves girls wearing poufy dresses and fancy lingerie. I was thinking we could double date. Then it wouldn’t feel so stressful. Neither you or Dan would have to carry the conversation.”

“Okay, that sounds great. I’d love a boy who appreciates my pretty clothes. There’s just one thing I should say. I hope it isn’t too personal.”

“What’s that?”

“I’m a virgin and I know I’m not ready to … you know, to have sex.”

Maria laughed. “You’re so silly. I’m a virgin too and I’m definitely not going to let Todd have sex with me! I’m saving that for a very special boy. We do make out and I let him feel me up. I’m even willing to give him a hand job if he wants it. But I haven’t let him touch me down there.”

“It’s a relief to hear you talk like that,” Tommy said.

“I’ll set it up with Todd. He’s got his driver’s license so he can pick us all up.”

“Great,” Tommy said.

***

After lunch Tommy and Maria followed Juliana to the lingerie boutique.

“Oh my God,” Maria said. “I’ve never seen such pretty bras and panties and wow everything! This is so much nicer than the department store my mom takes me to.”

“I’ve gotten a lot of my underwear here,” Juliana said. “The store is devoted to that segment of women and girls who love to be feminine. The two of you should each pick out two bras. Now run along!”

Maria and Tommy ran off happily to look through the racks of bras, panties, garter belts, girdles, slips, bodysuits, and stockings. It didn’t take them long to settle in on one particular full cup bra adorned with a vibrant pink floral print on a white background with embroidery at the upper cups and center front. “This is it! This is it! I love this bra so much!” Maria said. She looked through the bras and took out a 34 D. “What’s your bandwidth, Tammy?”

“36.”

“Yay. Here’s a 36DD. Now we can both have the same bra!”

“Neato!”

“Now let’s each get another bra!” Maria said. “We’ll choose separately. That should be interesting.”

“Great idea,” Tommy said.

They split up. After looking through most of the shop Tommy saw a bra, panty, and garter belt set that he adored. He fetched Juliana to ask her about it. “I like the idea that my underwear matches.”

“I’m the same way. That’s an exquisite set! You haven’t yet worn a garter belt but we can make that our next lesson.”

“You’ll let me buy this set?” Tommy asked.

“We’ll charge it to your parents when they come back,” Juliana said laughing.

Maria came up to them holding two bras. “Look at these bras! They’re so much prettier than the ones my mom gets me!”

“They cost more too,” Juliana said. “The two of you should try the bras on now.”

Tommy and Maria went to the single dressing room. It was barely big enough for the two of them. Full length mirrors were on either side. As soon as they entered Maria lifted her top off over her head. Tommy unbuttoned his blouse. In the tight confines of the room, their bras practically touched. “Luckily our boobs aren’t any bigger or we wouldn’t fit in here!” Maria said laughing.

“That’s funny,” Tommy said.

“You’re bra is so pretty,” Maria said, “and your breasts are big!”

“You also have a pretty bra and your breasts are also big.”

“My bra is not as pretty as yours!”

“That’s your old bra! Let’s try on our new bras,” Tommy said.

He took off his bra and put on the pink one that Maria also had.

“Mine fits really well,” Tommy said.

“So does mine!” Maria said. “Let’s take a selfie.” She held up her phone and took a picture of the two of them in their identical bras.

“Send me a copy,” Tommy said. Maria gave him her phone so he could enter his phone number.

“It’s so nice to meet a girl who like pretty bras and clothing,” Maria said. “I sometimes feel like I’m the only girl who likes to know that she’s wearing pretty underwear underneath her dresses. In the locker room, the other girls mostly have ugly bralettes and sports bras. They’re a blah tan color with no lace. It looks like hospital bandages!” Maria laughed.

“I have Juliana to thank for helping me buy pretty clothes,” Tommy said.

“She’s so wonderful. I hope to have a wardrobe just like hers one day!”

“These bras fit,” Tommy said. “We should try on our other bras.”

They took off the pink bras and Tommy and Maria each put on the other bra they had selected.

“Mine’s comfortable,” Maria said.

“You look fabulous in it,” Tommy said.

“Right back at you,” Maria said.

***

They rejoined Juliana. “You girls have exquisite taste.”

“What did you find?” Tommy asked. He saw that Juliana was holding a garment.

“A beautiful girdle. I’m going to try it on now. The two of you can help me decide if I should get it.”

Juliana went to the dressing room and after a minute she opened the door and stepped out wearing a girdle and her bra. “It’s princess pink imported from Paris.” Juliana turned around showing her extraordinarily perfect rear end.

Tommy felt stirrings of love for Juliana. Everything about her belonged to a world of happiness and beauty that he craved to be a part of. “I love the way you look in the girdle,” Tommy said. “I don’t know what’s prettier: you or the girdle!”

Maria laughed. “I agree. I can see how nice it must be to wear stockings instead of pantyhose. You get to wear winsome girdles.”

“Garter belts, as well,” Juliana said.

***

A few days later Maria called to say that she’d arranged a double date between her and Todd and Tammy and Dan. “We’ll pick you up and go to the movies.”

“That’s great. I’m excited.”

“Dan is very excited. I showed him the picture we took of us!”

“Wearing our bras? You didn’t show him that!” Tommy exclaimed.

“I did! There’s nothing wrong with getting a boy excited before the date. That way it won’t be a dud!”

“If you say so! What should I wear?”

“One of your prettiest dresses. Let’s get Dan to the point where he can’t resist you!”

“You’re so cruel, Maria!” Tommy said and they both laughed.

***

Dan and Tommy sat in the back seat of the car as Todd drove them all to the movie theater.

“What film are we seeing?” Tommy asked.

Todd laughed. “I’m not sure we’ll be seeing a lot of the film.”

“You devil,” Maria said, though she didn’t contradict him.

Tommy wondered what Dan’s expectations were. Dan sat on the far side of the seat from Tommy. It was as if Dan had to make sure that he didn’t touch Tommy’s dress which fanned out over the seat in a wide arc. His crinoline was bunched up under the skirt. Was Dan too scared to approach him or maybe he wasn’t attracted to Tommy. Tommy was relieved that it was the boy on the date that had the responsibility for how it went. All Tommy had to do was to smile, be pleasant and accommodate Dan’s lust to the extent he wanted to. He was under no obligation to be physical with Dan, but he did think Dan was quite handsome. It would be a nice coup to have such a fine-looking boy find him to be so pretty and sexy that he wanted to have physical contact.

At the theatre Dan paid for Tommy’s ticket and bought him popcorn and a drink. The four of them sat together in one of the last rows of a relatively sparsely full theatre. Todd and Dan had purposefully chosen a movie that wasn’t popular.

A few minutes after the theatre darkened and the film began, Tommy was aware of Maria and Todd kissing. He had the sense that they had a lot of pent-up desire that they were releasing quickly as the film started. Tommy watched the film and saw that Dan was also watching it. He figured it would be a bit strange for Dan to immediately begin kissing him. Afterall they only met a short time ago. On the other hand, the implication that this was to be a make-out date was fairly clear from Maria’s description of it.

“Dan is super cool looking – but don’t expect him to say much," She had warned him. "He’ll probably be a bit shy but eventually he should come around and get the courage to kiss you.”

“What should I do,” Tommy had asked Maria.

“You can try flirting with him. I’m not sure he’s smart enough to figure out what you’re doing,” she had laughed. “Seriously, you could brush your hand against his leg. Something like that. It might prime the pump!”

A half-hour into the movie Dan hadn’t made his move. Meanwhile Tommy saw that Todd had his hand inside Maria’s blouse and was feeling her breasts. He decided that Dan needed some encouragement. He gently rested his hand on Dan’s knee for a minute and took it away. When he looked at Dan, Dan was looking at him. Tommy sat back in his seat and a few seconds later felt Dan put his arm across his shoulders. Finally, Tommy thought Dan was going to make his move.

With his heart beating furiously Tommy watched as Dan swung his body around and moved his mouth to Tommy’s. At first Dan brushed his lips gently against Tommy’s then he moved in and began kissing him in earnest. Tommy’s heart fluttered with the novelty of making out with a boy for the first time. He again rested one hand on Dan’s knee. The other encircled Dan’s back.

While Tommy was not an expert on kissing, he decided that Dan was pretty good. At least he found himself enjoying the kisses. Long relaxed joining of lips and tongues. It was pleasant. He thought that from time to time he heard a moan coming from Dan’s throat. It was hard to keep track of time but Tommy figured they had been kissing for fifteen minutes when he felt Dan’s free hand resting on his breast. The dress he was wearing wasn’t optimal for getting felt up in. But Dan’s hand figured out that the neckline was low cut enough for him to work his hand down onto Tommy’s breast outside his bra. This seemed to greatly accelerate Dan’s passion and he kissed Tommy ever harder as his fand worked itself around and eventually inside Tommy’s bra. If Dan knew that the breast inside the bra was smooth silicone and not human flesh he didn’t let on. He seemed to really like feeling the hard nipples.

Five minutes later Dan pulled back allowing them both a chance to rest. Tommy felt a great confusion in his gaff as his excited penis tried to figure out what it could and couldn’t do. He looked over and saw that Maria was stroking Todd’s penis while they kissed. That definitely seemed like something that he’d be able to do to Dan if that’s what Dan wanted him to do.

Tommy slid his hand toward Dan’s belt buckle and felt around until he found the top of the zipper on Dan’s jeans. After some frustrating effort Tommy got his fingers on the pull tab and slowly worked it down. It wasn’t easy to move but he persisted until he could insert his hand through the zipper opening to touch Dan’s boxers. He sensed Dan’s excitement. He could imagine that the slow pace of his effort could only drive Dan wilder and wilder with passion.

Now that Tommy had his hand on the boxers he let it rest for a minute before feeling around. Inching his hand downwards it encountered a bulge formed by Dan’s large, excited cock. Now his problem was figuring out how to get his hand inside the boxers to liberate Dan’s penis. He groped his fingers around to find the pee opening and eventually snaked his hand inside where it encountered the top of Dan’s dick. With a wing and a prayer, Tommy pulled gently on the stiff member trying to get its tip through the hole and out into the atmosphere. After repeated attempts that required bending Dan’s unbendable cock, Dan finally came to the rescue by gently removing Tommy’s hand and inserting his own. He pulled his boner out of his boxers and through the zipper hole of his jeans.

With his cock standing at attention Tommy gently encircled the shaft with his hand. It was hot to the touch, firm yet pliable. The end was wet. It was the first time he’d touched a boy’s penis. He used his fingers to massage underneath the top and he felt the penis rhythmically pulsing into stiffness. Tommy decided this was fun. He enjoyed giving Dan pleasure. It was nice to hold a cock like this. He turned his attention back to the movie while his hand played with Dan’d dick. He slid it up and back. He held onto the end. He massage different parts of it. It occurred to him to see what Dan’s balls felt like and he slid his hand down there and cupped them.

After another fifteen minutes or so, Tommy noticed that Maria was sliding her hand quickly along Todd’s penis. Moreover she had gotten out a tissue and held it in her other hand. He saw Todd arch his back and evidently climax while Maria expertly positioned the tissue to catch his sperm. Tommy was amazed how silently the two of them carried that out. The closest people to them were five rows ahead and they didn’t turn around.

Tommy turned to look at Dan and even in the gloom he could see that his face was distorted. Dan leaned closer to Tommy and whispered, “Please finish me off! I’m dying.”

“Oh, okay, sorry,” Tommy said.

Tommy wondered how he’d get Dan to cum. Stroking ever faster was probably the safest approach to take. He drenched his hand in spittle and resumed sliding it over Dan’s penis. He concentrated hard on rhythmically sliding his hand from the base to the top. After a dozen moves he increased the pace a bit. Dan’s cock had gotten harder than before. Another dozen strokes and he sped up even more. He felt Dan’s body quivering and then shaking. Finally Dan put his hands over his mouth as if to silence himself while cumming. Tommy realized that he had forgotten to get a tissue ready. He wasn’t so poorly brought up that he’d let Dan cum all over the seat in front of them and the floor. More than that, there was no way that Tommy was going to risk cum landing on the skirt of Juliana’s dress!

Tommy stopped what he was doing and reached in his purse and took out a hankie that he kept there. He whispered to Dan. “Sorry. I needed to get a hankie. Now I can finish you off!” Tommy wet his hand again and applied the saliva to Dan’s cock which was a bit less hard than it had been before. Tommy resumed his rhythmic stroking and Dan got closer and closer to cumming. Looking at the screen Tommy saw that the movie was ending. He accelerated his stroking but it was too late. The house lights went back on and Dan raced to get his cock back inside his pants.

Todd said, “Great movie!” and Maria laughed. He noticed Dan’s face and asked, “What about you Dan? Did you like the movie?”

“Yeah, oh yeah. It was great.”

They headed to the car and Todd and Maria suggested they stop at an ice cream parlor for sundaes before heading back home.

“Great idea,” Tommy said, but when he looked at Dan’s face he thought that maybe he had made a mistake. Dan looked more than a little miserable.

“Good!” Todd said.

Once Tommy and Dan settled into the backseat, Tommy whispered to Dan, “Are you okay?”

“I’m a little embarrassed.”

“Whatever for?” Tommy asked.

“Can I be honest?”

“Sure.”

“My balls ache. You know when a boy gets excited and doesn’t release …”

“Oh I’m so sorry!”

“It’s not your fault! The lights came on!”

“What can I do about it?”

“The drive to the ice cream parlor is ten minutes.”

“Okay sure, I’m happy to oblige,” Tommy said.

“Thanks. You’re an angel. Also …”

“What? Don’t be afraid to tell me.”

“Could you maybe use your mouth? It might be a lot faster.”

“My mouth? Oh, you mean I should suck on your penis. I guess I can do that. I’ve never done it before but it’s probably pretty straight forward.”

The engine started up and Dan wrestled his penis out of his pants again. Tommy slid down and leaned over him. He looked at Dan’s dick in the dark of the rear seat. It was sort of flopped over. He held it up with one hand and then gently brought it into his mouth. Almost immediately it stirred and began getting hard. Tommy swirled his tongue around the shaft and then put it further into his mouth. It was an interesting experience. Kind of pleasant and erotic. His own penis once again showed that it had a voice in the proceedings.

Tommy decided that a rhythmic pattern was called for if he was to get Dan to climax before they reached the ice cream parlor. He concentrated his effort in moving his head up and down so the penis slid back and forth in his mouth. He did all he could to emphasize contact on the sensitive part underneath the glans. Dan tightly held Tommy over himself. The tension in Dan’s thigh and arm muscles as the car bounced along the road gave Tommy an indication that he was making good progress in bringing Dan to a climax. Just when he thought that at any second Dan was about to give him a mouthful of cum, the car stopped and Todd called out, “Here we are folks!”

Tommy sat up and used his hankie to dry his mouth of saliva and Dan’s precum. He looked at Dan and saw the misery in his face. Dan reluctantly put his penis back in his jeans and exited the car. The four of them found a table in the ice cream shop.

“Dan my man,” Todd said. “Are you okay?”

“Yeah, fine,” Dan lied. He had to sit down slowly to avoid stressing his aching balls.

Tommy, Todd, and Maria had a lively conversation. Partly about the movie – at least those portions they had seen. Dan, who was never known as a great conversationalist, was mostly silent biding his time for the trip back when he hoped Tommy would finally be able to finish him off. He nixed the idea of jerking off in the rest room with memories of Tommy’s wonderful sucking on his cock fresh in his mind. It was worth a little extra pain to have Tommy resume his blow job.

When they returned to the car Tommy felt sorry for Dan. He threw himself over Dan and kissed him passionately. He whispered in his ear, “I’m so sorry poor Danny. I’ll finish you now!” Tommy liked the idea of smothering Dan with his femininity. He was happy that he was able to offer it to him.

Tommy dropped down to resume his ministrations on Dan’s cock which was already out of his pants. Tommy sensed that Dan’s cock was somewhat fatigued from all the stroking and sucking he had done. It was hard but could be harder. Getting him to orgasm was going to take a concentrated effort. He redoubled his sucking, taking long solid strokes with his head. He tried to engage his tongue usefully as well as his hands in massaging Dan’s balls. After one bump in the road caused Tommy’s teeth to nick Dan’s cock he apologized profusely though Tommy wasn’t sure that Dan could make out what he was saying with a dick in his mouth.

Finally Tommy sensed that he’d gotten Dan’s cock rigid. Dan’s thigh and leg muscles were flexing, his back was arching, orgasm was imminent. At that very moment, the car came to a halt in front of Tommy’s house. Dan put his hand on Tommy’s head to make sure he didn’t abandon his effort. That wasn’t necessary because come hell or high-water Tommy was determined to give Dan relief – even if Maria and Todd turned around to watch. With the car parked and Tommy moving his head up and down as fast as he could Dan’s closed eyes fluttered open and saw his friends watching him.

Maria couldn’t stop laughing at Dan’s desperation. Tommy heard the laughter and figured that Maria and Todd were watching him. He accelerated his head motions in one final effort to get Dan across the finish line and then was pleased to hear Dan vocalizing what sounded like a war whoop as a fountain of cum shot up into his mouth. He did everything he could to contain the cum so that it didn’t hit his dress or the seat of Todd’s car. His mouth quickly filled and he swallowed it to get room for the rest of Dan’s prodigious effluent. Finally, Dan’s cock stopped spasming, the flow of cum ended and Tommy took his last few swallows. He got out his hankie and wiped his lips.

“Bravo!” Maria said as she and Todd clapped their hands.

“A magnificent performance Tammy,” Todd said.

Dan had a tired and satisfied smile on his face. His ordeal finally ended with the best orgasm of his life. “God Tammy, you’re the greatest,” Dan said.

“I really enjoyed doing that,” Tommy said. “Maybe you’d …”

“Sure, Tammy,” Dan said. “I’d love to take you out again.”

Before Todd drove off Maria ran up to Tommy. “You really like Dan?”

“I do, though we didn’t really get to talk.”

“I’ll let you know what Dan thinks and give you a call!”

“Thanks, Maria.”

***

Juliana was waiting for Tommy when he entered the house. “Tell me all about your big date, Tommy!”

“It was nice. I didn’t get to see too much of the movie but Dan is a nice boy. He’s polite and gentlemanly. I think he really liked me. Well it was a make out date and we made out.”

“I remember having make out dates when I was your age,” Juliana said.

“Dan and I kissed a lot. I think he’s a good kisser, though I don’t have much experience. I also …”

“You also what?”

“To be honest I also gave him a hand job – but that got interrupted. Then I gave him a blow job and that got interrupted but then finally I resumed the blow job and got him a beautiful orgasm. He said it was the best he ever had.”

“Poor Dan and his blue balls.”

“I know they must have really hurt. He could barely sit down.” Tommy and Juliana laughed.

“Your mouth must hurt after such a long blow job,” Juliana said.

“Yeah my lips and jaw got tired but thank goodness he finally came. I really enjoyed his excitement and it felt good to give someone else so much pleasure.”

“What happened to his cum?”

“He ejaculated into my mouth. I was paranoid about getting any of it on your pretty dress or on the car seat.”

“How did that feel?”

“I think it’s really cool when the hot jets squirt up into your mouth. It’s got an odd taste but I could see getting to like it once I’m used to it.”

“I know what you mean. I’ve given a blow job from time to time. The men I did it to loved especially to see me in a subservient position. I’m not so sure that that’s an accurate description of our role. After all, as long as we control the sucking on their cocks it seems like we have all the power!”

Tommy laughed. “I did feel like I had the power. Dan was so desperate to cum that I had him at my mercy.”

“The bottom line is that it’s so much nicer being a girl than a boy! Isn’t that true, Tommy?”

“Yes indeed!”

Juliana and Tommy sat together for a while. Juliana put her arm around Tommy and held him as he leaned against her.

Tommy said, “I wonder if Dan knows I have a penis.”

“I tend to think he does. Maria probably told Todd who cleared that with Dan before setting up your double date.”

“Yeah, I didn’t think about that. What does it mean about Dan?”

“Some boys prefer boys that are girls. Dan might be like that. Or else Dan just doesn’t mind because he likes both girls and boys. He never tried to feel you up down there?”

“No, though he did seem to like feeling my breasts.”

“If you get to know him better, then the two of you ought to communicate your feelings. There’s no harm and plenty of benefit for getting on the same page with each other.”

“You’re so smart Juliana.”

She laughed. “Now that you’ve sucked a boy’s penis and made out with him, do you think that you prefer boys to girls? You said you were in love with me! What do you prefer?”

“Of course I would always want you! But I know I can’t have you!” After a minute Tommy continued, “I liked being with Dan because he made me feel like a real girl – deep down inside. When I was giving him a blow job I was sure that I was a girl and had always been a girl. On the other hand …”

“On the other hand?”

“I would like to meet a girl who is more on the boy spectrum than I ever was. She might like me being feminine and we could be in love. I could see that happening.”

“Luckily, you have many years to figure out what you desire. Your parents will be back in two days. Right now I’d say you’re 99 per cent a girl. You move and act like a girl. Talk like one. Emotionally you’re definitely a girl. You’re an expert in girl’s clothing. I’ve watched you put on your shear stockings and you’re as skilled as any girl who has been putting on her stockings for years.”

“What is my missing one percent?”

Juliana laughed. “Nothing in the world is ever 100 percent. That’s why I said 99.”

***

Two days later in the afternoon, Tommy greeted his parents as they returned from their trip. He begged Juliana to be with him for the occasion and she stood to the side to watch the proceedings. Tommy wore a white taffeta dress that showed off his chest and his stockinged legs.

“Oh my word!” Cecilia said. “Juliana has worked wonders on you. I wouldn’t even think you’re a boy. What a precious girl you’ve become. My daughter! Let me get a good look at you.”

“Gosh, Tommy,” Steve said. “You truly have become my daughter. Your mother and I want to hear every detail of your transformation.”

“I’d love to share that with you, Dad. Juliana is an incredible teacher!”

“Thank you Juliana!” Cecilia said.

“Tammy and I had so much fun together. I should explain the name. We thought that Tammy was a useful name to call Tommy until you and Steve decided what Tommy’s new name should be.”

“Right, that’s in interesting point. We’ll have to think about it,” Cecilia said. “If Tommy had been born a girl we were going to name her Tommy-belle. But Tammy might be better.”

Everyone laughed.

The End