The Dress-Up Game – Moms Edition

By

Pamela

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Greg’s mom, Gail, met up with Jill’s mom, Judy, at a Starbuck’s a couple of months after they had been brought together by their children’s hijinks: the so-call Dress-Up game. Ever since then they had become good friends. “Those kids of ours are something else!” Judy said.

“You can say that again,” Gail said.

“They’re just thirteen and they’re dealing with their own sexuality as if they were adults. Go figure.”

“I know. It’s uncanny how the two of them zeroed in on how their individual desires fit together hand and glove.”

“I feel like I owe you an apology,” Judy said. “Afterall, if I hadn’t sent Jill to get a new bra, then Greg wouldn’t have gone to my friend’s lingerie shop. The two of them would never have discovered their dress-up game.”

“True, except that I think that for quite some time Greg has had a desire to wear girl’s clothes.”

“How do you know that?” Judy asked.

“Bit by bit he and I have talked about his love of the dress-up game. He shared with me the fact that about a year ago he realized that he’s jealous of girls because they get to be girls. He got a bit weepy and even said that I’m sitting next to him having a woman’s body parts and he so much wishes that he had them.”

“Wow, that’s pretty strong stuff.”

“You’re telling me. I hate to see his frustration,” Gail said. “I’m sitting here with my breasts, my fairly large breasts, wearing my bra and I don’t regard them differently than my foot or arm. I’d have to not have boobs to want boobs. This drives Greg to distraction. He wonders how girls don’t see having boobs as magical.”

“The grass is always greener …” Judy said.

“Exactly. I told him that the moment he had boobs, he’d think differently about them. Initially I suppose they would be pretty exciting to have, but over time he’d get used to them like the way women do and then they might not seem so magical anymore.”

“Like listening to the same song over and over. It can lose its excitement.”

“But as long as he doesn’t have them, they’ll always be tremendously exciting. I’ll bet he takes his penis for granted. There are some girls who envy boys for having a penis. Once they get one, however, they might take it for granted. I hope Greg understands this now. At any rate, he’s so lucky to have met a girl like Jill who actually prefers boys like him.”

“Yeah, I can imagine that men that cross dress might have a hard time meeting women who are enthusiastic about it. Probably some do tolerate it. But how many, like Jill, really encourage it?”

“You know, Judy, I think you’re on to something here. I love men and their penises. But at my age it’s been really hard to meet nice men.”

“I have the same experience. I see where you’re going.”

“Yes. If we look for cross dressing men and let them know that we rather like them dressing up, then we might get ourselves some really nice guys. Guys who are considerate, appreciative and have really nice functional penises to give us great sex.”

“Oh my God, Judy, we’re so brilliant!”

“We just need to imitate Jill!”

“But where will we find cross dressing guys?” Gail said.

“We could go on dating websites saying we’re looking for cross dressers.”

“I’m not so comfortable with that. I’ve been on dating websites and not been thrilled with the outcomes. I’d like to see the guys before they know that we’re looking at them. That way we could have more control.”

“That seems smart. We could lurk at places where guys are buying women’s clothing,” Judy said.

“Bingo. That could be fun. What stores?”

“We can go to Macy’s and hang out at the dresses or possibly lingerie. When we see a guy buying something, we go to the same item and say, “Isn’t that a pretty dress. Do they have size ten? That might draw the guy into a conversation.”

“You think so?” Gail said.

“Well we could say something like, ‘I’d love it if my husband bought that for me.’ The guy might then reveal that the dress is for himself.”

“Then we could offer to help him get the right size!”

“That might work,” Judy said.

“Here’s an idea. I think we should aim to play the same game as Greg and Jill are playing. If the man buys a dress, and he’s agreeable to becoming our friend, then you and I could get the same dress as him. We could also all get the same bra and panties and pantyhose and shoes. Just like the kids!”

“That’s a brilliant idea. When we get all three of us together dressed the same, then you and I can share him.”

“For sure. He’ll no doubt have a great boner and besides that, we could put his mouth to good use at the same time!”

“Are you getting wet thinking about that?”

“I sure as hell am!!”

“Let’s go right now. I’ve got the day off.”

“Me too!”

***

The ladies drove to a nearby Macy’s and went to the floor where dresses were sold. They wandered through it looking for a single man. After a half hour without finding one, Gail said, “One of us should go to lingerie. If one of us sees a man, we can call the other and they can come.”

“Great idea. I’ll head on over to lingerie,” Jill said.

Fifteen minutes later Gail saw a man walking slowly through the dress section furtively sneaking glances at the racks of dresses. It was obvious he was trying to see as much as he could. She saw him stop at a section devoted to sundresses. He looked to be in his mid-twenties. A little young for Jill and her, but he was cute enough. He was in front of a display of pink and light green dresses with a floral motif. He seemed hesitant and almost like he was about to run away. Gail felt some excitement mounting in her chest and she slowly moved in.

***

Carl perused the latest Macy’s catalog. His two favorite sections were dresses and lingerie. A pretty sundress in bright warm pink and light green colors caught his eye. God was it sexy, he thought. He imagined himself wearing the dress. It would also be wonderful to buy a bra and panty to wear under the dress. It was a nice daydream. Unfortunately, if he wanted to get the sundress he’d have to find the courage to go to Macy’s and buy it. Yeah right! How many times in the past had he psyched himself to buy a dress or a bra or a panty and chickened out?

He would like to order the dress online, but as long as his girlfriend, Kelly, came by his apartment every few days, it was out of the question. If the package came on a day that she was there, he’d be exposed for what he was: A girl wannabe. He had dropped a few hints over the past year that he had no qualms about reversing roles in their relationship, but Kelly either didn’t pick up on the hints or didn’t want to encourage that kind of fantasy. If anything, he had the impression that she wished that he were more fit and more assertive than he was. She suggested that he join a gym and work out. If he could bulk up with some real muscles she might get more turned on by him. Carl said he’d look into it, but he had no intention of acquiring a more masculine physique than he already had. If anything, he liked the fact that his arms were thin and feminine. Having a bicep that popped up when he flexed would be depressing. In an odd way, however, he liked Kelly because she had such strong views about how he was supposed to be – even if he didn’t obey her wishes. Anyway, he had the feeling that Kelly would dump him as soon as a better prospect came along. He could not imagine ending things himself, even if it might free him up to finally order some girls’ clothing online.

When Carl finished looking at the catalog he decided that he’d do what he often did. He’d drive to Macy’s which was just a few minutes from his apartment. He’d walk through the dress section as if he were headed somewhere in the store and then maybe he’d see the sundress. Then, perhaps a flash of courage would come over him and he’d pick out a size fourteen and go to the cashier, take out some cash and buy it. If he chickened out, he chickened out. No harm, no foul, except that he’d be no further along in appeasing his desire to dress up like a girl.

***

Gail watched the man who had stopped at the sundresses. She could see him glance around in all directions. There was no one near him. He became preoccupied looking at the tags on the dresses as if searching for a particular size. Like a lion in pursuit of a wildebeest Gail approached the man from a direction where he wasn’t looking. She got almost on top of him before he sensed her presence. Up close she saw that he was shaking with nervousness. He was frozen in place with a look on his face suggesting that he might suddenly run for dear life.

Before he could run, Gail said, “You’ve got a good eye for a pretty sundress. I’m looking for a size ten.” Her talking to him had the same effect as landing a harpoon in a whale. He might swim around trying to get away, but he wasn’t going to break free.

The man said woodenly, “I saw a ten.”

Gail searched through the dresses and said, “I found one!” She took it off the rack and held it up. “Don’t you think it’s pretty? Well, obviously you do since you’re looking at it.”

The man was avoiding her eyes but finally made a grunting sound and Gail said, “What size are you looking for?”

He looked at her fearfully and Gail felt sorry for him. “Fourteen?” the man said in the form of a question causing Gail to laugh slightly. There was no doubt that the guy wanted the dress for himself.

“Fourteen. Let’s look.” Gail went through the dresses and said, “Here’s one!” She took it off the rack and held it up for the guy to see. “Does this look like the right size for …?”

The man averted his eyes, and speaking to the ground said, “my wife.”

There was no wedding band on the man’s hands. He slowly looked up at Gail and then turned away when their eyes met. “Can I ask you a personal question?” Gail said. She found it strangely enjoyable to see how nervous she made the man. She had a power over him that she had never had before with her ex-husband or other men she had dated. She and Judy had struck gold.

“Personal question?”

“It’s none of my business, but you’re not really buying the dress for your wife are you? You’re not even married.”

The man looked down at the ground and said, “I’m sorry. I should go now.”

“Why? You want to buy the sundress, don’t you? It’s a very pretty one.” Gail stepped back and judged Carl’s body. “Yes, I can see that you most likely wear size fourteen.”

“Me?” The man sounded alarmed and though he was squirming as if he had to run to freedom or to a men’s room, Gail could see that he’d never leave until she released him.

Gail said, “What’s your name?”

“Carl.”

“Nice to meet you Carl, I’m Gail.”

“Hello. Can I go?”

“Am I making you nervous?” Carl nodded his head. Her power over him was fascinating. Here was a man who could not disobey a woman. Carl looked to be in his mid-twenties and was cute, even handsome. Gail laughed to herself. She was a schoolteacher and Carl was a naughty pupil. She could prolong this encounter for as long as she wanted. A delightful turn of events from her past relationships with men. Usually they ignored what she said and certainly did whatever they wanted without consulting her. This guy was a different animal entirely.

“Your nervous because the dress is for you, isn’t it?”

The man looked at Gail. “Yeah.”

“You want to wear the sundress?”

“Yeah. Are you going to tell somebody?” His voice was pleading and his eyes were close to tears.

“Please, Carl. I think you’d be quite attractive wearing the sundress. You have the right shape.”

“You’re not making fun of me?”

“Please, Carl. Now you’re hurting my feelings.”

“I’m sorry!” Carl said. He was clearly horrified to think that he had done that. “It’s just that I never thought a woman would ever approve of me wearing a dress.”

“I don’t know where you got that impression of women, Carl, but I know of many women that wouldn’t object to you wearing pretty dresses.”

The beginnings of a smile formed on Carl’s face. “I don’t know what to say, Gail is it? I just assumed women wouldn’t want me to wear dresses.”

“Perhaps some women, but certainly not all. Regardless of how women might judge you, the reality is that you’re on the girl-side of the boy spectrum. Like girls, you have pretty, thin arms and a girlish shape. Your upper chest is not manly and your waist is a bit thin. You’ll be quite cute wearing the sundress.”

“I can’t believe I’m saying this, but I might just buy the sundress! You’ve given me the courage! I can’t thank you enough.”

“Please, Carl. It’s the least I can do for a very nice man. Of course I assume you’ve got a bra and panties to wear with the dress.”

“A bra and panty? I need to wear a bra and panty with it?”

“How were you expecting the sundress to look right on you without proper underwear?”

“I don’t know. I didn’t realize that.”

“You poor dear. This is something that girls would know about. You can benefit from some coaching.”

“Coaching?”

“You need to spend some time imitating girls if you’re going to wear their clothes. The way girls behave and act is intimately related to the clothes they wear. That’s probably why you want to wear the sundress in the first place.”

“I don’t follow.”

“Because you know in your bones that wearing the sundress will bring with it all the girlish things that go with wearing a sundress. Like, for example, having to wear a bra and panty. It’s all interconnected. What’s that famous expression, ‘Clothes Make the Man’?”

“How am I ever going to learn all that?”

“I could help you.”

“You could?”

“At the minimum I could help you buy a proper bra and panty so that you can at least feel pretty wearing the sundress the way the designer intended. We could go to the lingerie department and shop together.”

“You would do that for me? A complete stranger?”

“You’re not a complete stranger! We know our names and the fact that we both like the same pretty sundress.”

Carl laughed. “I’ve never met a woman like you before. My girlfriend, Kelly, would never permit me to wear girls’ clothes.”

“Permit you?”

“She wouldn’t allow me to wear girls’ clothes if I asked her. She’d get mad at me for asking. She might even hit me or something. She can get physical if I stress her. Particularly if she’s having a bad day.”

“So she’s abusive?”

“She says that it’s her way of trying to teach me to act manly. If I was sufficiently manly, then she could never get away with her dominance. She’s always suggesting I work out at a gym and get some muscles. If I had muscles, then she says she wouldn’t have to act as if she was the man in our relationship. If I’d just start acting like a man, then she could go back to being the woman she knows she is and would rather be.”

“She has a very narrow view of men. A man with muscles can be sexy, I won’t deny it. But a man who enjoys being pretty and loves the same clothes that I do, can be an even bigger turn on.”

“Really?”

“Yes. They have a sensuality that women adore. Their skin is electrified with their sexuality. To the extent they love feminine fabrics against their skin and having a womanly shape they exude an essence that speaks directly to my womanly private part. It gets juicy, as the boys say.” Gail laughed.

“I’m kind of overwhelmed by you. I never knew that women like you existed.”

“That’s kind of you to say. So, would you like my help in buying lingerie?”

“Would you? That is so kind of you. I’ve been so afraid for so long to buy myself a bra, yet I’ve hungered for one ever since I was like thirteen.”

“How old are you now?”

“I’m twenty-five.”

“Wow. Twelve years of longing. I’m quite happy to help you buy your first bra and panty. Boys like you have every right to express themselves and particularly for an audience of women like me that can appreciate how very special you are.”

“I’m having to fight back tears,” Carl said.

Gail laughed and said, “Come here, Carl. Allow me to hold you until the moment has passed.”

Gail enveloped Carl in her arms while his breast heaved a few times with emotion. It was clear to her that Carl had a lot of bottled-up feelings that he was finally getting a chance to release. It was nice to make another person happy. Of course in this case she hoped that she and Judy would get to enjoy the pleasures that came with such a young handsome man.

When Carl was calm again, Gail said, “So let’s buy our sundresses and then go downstairs to the lingerie section.”

Carl paid for his size fourteen dress in cash and Gail bought two identical size ten dresses. “I have a friend, Judy, who will also adore this dress. We’re both size ten.”

“I thought ladies don’t like to be seen wearing the same dress.”

“That’s true. You’re very astute. Under normal circumstances we wouldn’t be caught dead wearing the same sundress at the same time. However, Judy and I have been wanting to play a dress-up game where we dress identically – even down to the same underwear, shoes, everything.”

“I never heard about a game like that.”

“Actually our kids invented the game and Judy and I adore watching them play it. It’s made us think that we ought to play it too.”

“That’s interesting.”

“In fact, I left Judy shopping in the lingerie department. I’ll introduce you to her.”

As soon as Gail said these words she could see a wave of panic run through Carl’s face. She hastened to say, “Please, please don’t worry about Judy. She and I are two peas in a pod. She appreciates men that want to explore their feminine side the same way that I do. Trust me.”

“Okay. I do trust you.”

“Good. Judy can help us pick out a nice bra and panty for you.” Gail was sure that Judy was going to flip out when she brought Carl to meet her in the lingerie department.

***

Judy took up a vantage point near the pantyhose display that gave her a panoramic view of the bras and panties. When she had first arrived she saw a man checking out foundation garments. After wandering close to him she decided that he wasn’t the kind of guy that Gail and she were looking for. He was probably a good ten years older than each of them and somewhat grizzled. They needed a guy who was young but not too young. Someone who could be their playmate. They’d play the dress-up game with him and then who knows? If they did it right they might get some nice sex with him. Take advantage of the equipment that he supplied to the threesome.

Another single guy entered the lingerie section and Judy snapped to attention to see if he would be a good candidate. The more she studied the man the more she got the impression that he was much younger than she and Gail. The guy was maybe seventeen. He stopped in front of a display of bras and was looking through them, when a young girl showed up and joined him. It was clear they knew each other. The guy said something and they laughed. Perhaps he had suggested a bra for her that she thought was funny. Judy thought how nice it would be to have a boyfriend with whom one could shop for lingerie.

Judy was thinking that maybe her experiment with Gail was less likely to succeed than she thought, when she saw Gail approaching her accompanied by a handsome guy. He looked to be twenty something. They entered the bra and panty display area and Judy walked toward them. When she came up to them Gail said to the man, “This is my friend Judy. Judy this is Carl. ”

Carl gave Judy a wan smile. As much as he trusted Gail, he was still all nerves at the prospect of meeting another woman. “Hello, Carl,” Judy said trying to make eye contact.

“Carl is a bit shy,” Gail laughed. “I met him by accident buying a sundress. I told Carl that you and I could help him buy a panty and bra to wear with his sundress.”

Judy said. “It’ll be fun to buy bras and panties together.”

Carl looked up at Judy. “Really, you don’t mind?”

Judy laughed. “Yes, really. Show me your sundress.”

After hesitating and looking at Gail who smiled at him, he took his sundress out of the bag and handed it to Judy. “Oh, my goodness, Carl! What a very special and pretty sundress.”

“Thank you,” Carl said.

“Carl doesn’t have any bras or panties,” Gail said.

“So of course he’s got to get a nice bra and panty if the sundress is going to look right on him.”

“Exactly. That’s what I told him.”

“Getting one’s first bra is quite an exciting time,” Judy said. “I was very excited when I got my first bra so I can imagine how you’re feeling, Carl.”

“Me too. I felt so grown up with my first bra,” Gail said. “The first time I wore it to school I remember glancing down at my chest as I was walking down the corridor. I could see how it held out my developing breasts, for everyone to see and I felt so adult. It’s a great feeling Carl. You’ll love the magic of your first bra. We should help you get one that you fall instantly in love with.”

“I can fall in love with a bra?”

“We’ll see. I think each bra you look at will affect you differently. And when you see the right one, you’ll know that it’s the one you really want to wear. That’s how girls are, Carl, and I’m going to guess that you’ll react to bras the same way that girls do.”

“Why do you think that?”

“Carl. You reacted to the sundress the way any girl would. That shows that you’re the kind of guy who might fall in love with a bra. Other, perhaps more typical guys don’t tend to react to dresses or bras with instant love.”

“Right.”

Judy helped Carl put his sundress back into its bag. She asked Gail what was in her bag. “I bought two size ten sundresses – the same one that Carl bought.”

“Oh my God, Gail, you want us to play the dress-up game with Carl. What a brilliant idea! Do you know what I’m saying Carl?”

“Gail did mention the dress-up game, though I thought that just you and her would play the game.”

“There’s no reason three can’t play. We should all play it! We all have the same sundress. Now we need to get the same panties, bra and whatever else we need.”

“Pantyhose and shoes,” Gail said.

“Right.”

“What do you say Carl? Do you want to play the dress-up game with us?”

“I think I would like to but … as I mentioned to Gail I have a girlfriend, Kelly, who would never let me play the dress-up game. She would never let me wear a dress. To be honest, our relationship is not that good and for a long time I’ve wanted to break up with her but I haven’t been able to tell her.”

“Why not?”

“She’s scary. I’m afraid to get her angry. She’s very forceful and you don’t know what she’s like when she’s upset with me. She can easily get angry if I do something wrong. I hate to think of how mad she’ll be if I told her I wanted to break up with her.”

“She’s abusive, in other words.”

“She’s only hit me a few times in the beginning. Then I learned to never do anything to give her cause to hit me.”

“Whether she hits you or yells at you. It’s all abuse. You need to get out of the relationship.”

“I know. Sometimes I think that she’s going to dump me because I’m not man enough to turn her on. So I think that might happen one day. I dream about that day coming. By getting the sundress outfit, I’ll at least be able to dress up and be happy on the days when Kelly doesn’t come by my apartment.”

“How sad, Carl,” Gail said, “to think of you living in fear with Kelly and then hoping to find some happiness by putting on girl clothes.”

“What if Kelly discovers your sundress?” Judy asked.

“I hate to think about that. She’d hit me for sure. She’d make fun of me. But her answer to it will be to carry through on her threats to make me into a real man. She’ll enroll me in a gym or something like that.”

“But she wouldn’t dump you?”

“No, I don’t think so. It’s crazy isn’t it?”

“Tell you what, Carl. Judy and I will help you get a complete outfit today. We’ll also buy the same bra, panty, pantyhose, and shoes as you do so we’ll be ready to play the dress-up game if you end up breaking it off with Kelly. After all, we already have the sundresses. Who knows, this might give you the incentive to find a way of standing up to Kelly. How does this sound?”

“If I may interject,” Judy said, “keep in mind that one of the nicest things about the game is that it’s an effective way for you to learn about being a woman in just a short time. Imitation is a powerful learning tool.”

“You ladies are way too kind to me. I think this is a great idea if it’s no trouble for you. I think you’re right that the thought that I could be playing the dress-up game if only I had courage to break up with Kelly, might one day give me that courage. I’ll have to see.”

The women could see from the fear in Carl’s eyes that his bravado would probably be short lived. Carl was clearly no match for Kelly. They would have to check up on him from time to time to make sure that he was okay. “We’ll be rooting for you Carl,” Judy said. “Let’s go bra shopping, shall we?”

“Yes!” Carl said. “I can’t believe I’m going to get to pick out a bra to wear. I hope it’s one that you also fall in love with!”

Gail and Judy laughed and Judy said, “Not every bra a girl wears is her number one favorite. She might have several different favorite bras. We want you to choose a bra that you fall in love with. Gail and I will surely love it also, even if we might think of a different one of our bras being the one we love the most.”

“Okay, but what size bra should I get?” Carl asked.

“Judy and I wear 36DD bras. Your bandwidth looks to be thirty-eight. You could get either a 38D or 38DD.”

Carl look stupefied. “I’m sorry but I don’t think I can fill a D or DD cup bra, can I? Shouldn’t I get an A cup or an AA cup?”

Gail and Judy laughed. “You could get an A cup, but a larger cup size – one that is close to our size – will allow you to look more like us.”

“But if I buy a bra with a large cup, how will I fill it out?”

“We’ll take you to a shop where we can buy breast forms.”

“Breast forms?”

“Silicone breasts. They come in many sizes, weights, and firmness. We’ll help you buy the most life-like breast forms we can find.”

“I just put them in my bra?”

“Yes, exactly. Your breasts will jiggle and bounce the same way they do for women.”

“I’m overwhelmed.”

“Good. So we’re looking for a 38D or DD bra. What bra style would you like?”

“I’m not so sure what choices I have.”

“Do you want a lacy bra?”

“Oh, yes. Certainly.”

“What color?”

“I don’t know. Any feminine color.”

‘Yes. That sounds good.”

“Underwire?”

“Yeah. Definitely.”

“Full coverage?”

“As against partial coverage? I’m not so sure about that.”

“He’ll want full coverage,” Judy said.

“You’re right.”

They sauntered through the bra section. Gail and Judy to either side of Carl pointed out different bras and commented on them. The women were tactile – touching the bras with their fingers. “Girls love sensual fabrics, Carl. We delight in the feeling of soft, silky panties and bras. Many blouses and dresses are fun to touch. Our clothing is lighter and more delicate than boy clothing.. Feel free to touch the bras and panties also. If you’re shopping for a bra, you’re allowed to shop the way girls shop.”

“I appreciate it,” Carl said.

“Come check out this bra!” Judy exclaimed. Carl and Gail joined her and Carl exclaimed, “Yes. This is it. This is definitely the bra I want! I’m in love with it!”

Judy took one off the rack and handed it to Carl. He examined the tag and said, “The color is pink diamond.”

“This is a wonderful choice for your first bra, Carl. It has such a pretty floral pattern forming the lower half of the cups and luxurious stretch Leavers lace on the top of the cups. The lace allows for the bra to provide a custom fit.”

Gail added, “It’s also supportive and has full coverage.”

Carl stared at the bra for a long moment and said. “It’s so pretty. I didn’t know that bras could be so pretty.”

“I agree with you, Carl,” Gail said. “This very well might end up being my number one favorite bra.”

“Here are the matching panties,” Judy said and handed them to Carl.

“These are so beautiful also. I can’t believe that this is happening. My first bra and panty and they’re so perfect.” Carl became choked up and a few tears went down his cheeks.

Gail took out a tissue from her purse and dabbed at Carl’s eyes. “You have the emotional instincts of a schoolgirl,” Gail said. “It’s so endearing.”

“Let’s pay for our bras and panties. Gail and I get 36DD bras and you get a 38DD bra.”

“Size 6 matching panties should fit all three of us.”

“We must get pantyhose to wear with the dress,” Gail said.

“For sure,” Judy said. “Then we’ll head to the shoe department and get some heels to go with the dress.”

“Pantyhose and heels?” Carl said.

“Pantyhose and heels make a girl feel on top of the world. You’ll love the feeling.”

Judy took Carl’s hand and led him to the pantyhose display. She and Gail picked out three pairs of identical pantyhose. After they had paid, Carl congratulated himself for finding the courage to make the purchase.

***

In the shoe department, Carl watched as Gail and Judy expertly perused the selection of heels in various displays. After a discussion they decided to go with a white sandal with a high heel. “This will look really good with our dresses,” Gail said.

“The heels seem kind of high. Do you think I’ll be able to walk in them?” Carl said.

“Perhaps they’re a bit high, but you’ll find them to be comfortable once you get used to them. Getting accustomed to walking in heels is a rite of passage for girls. Just like getting used to wearing a bra. Just remember that Judy and I will be with you every step of the way to help you be a girl.”

“It’s so overwhelming for me. I hope I don’t disappoint you.”

“Just let yourself go. Allow yourself to become who you truly are. Judy and I will always accept you for who you are.”

“You’re the two kindest women I’ve ever met.”

A salesperson joined them. He was no more than twenty-one years old. Gail explained that each of them wanted the same pair of white heels. Carl was certain the man made a face when he saw him, but he measured his feet without comment and went to the back to fetch the shoes.

“Let’s hope they have our sizes, else we’ll have to try a different shoe.”

“Dressing exactly the same is important for the game?” Carl asked.

“Yes,” Gail said. “That’s what makes the game so much fun. With every detail the same we become one person. Looking at each other we see ourselves. You’ll discover a world of intimacy and closeness between us that you never imagined existed. The female perspective on life that Judy and I have will enter the recesses of your mind and provide you all the benefits that femininity can give you.”

Carl reflected on what Gail had said. He would be entering the world he had wanted to be a part of for a dozen years. It was both frightening, mysterious, and irresistible to him. There was no going back now.

As luck would have it, the salesman returned with three shoeboxes. He gave them each a pair of footsies and Judy explained to Carl that he was to wear them when trying on the shoes. Carl summoned up his courage, took off his shoes and socks and put the footsies on and then the white heels. Judy stood up next to him and said, “Come now. Get up and walk around. No one is looking at you.”

Carl glanced around. There were some people nearby and he hesitated. Judy took his hand and said, “We’ll walk together. Use me to steady yourself.”

Carl stood up holding onto Judy who helped to steady him. Judy whispered to him, “This is another milestone for girls. Her first steps in high heels. It’s exciting. Enjoy the moment. Take some steps to that mirror over there so you can see how pretty you look in heels.”

Gail got up and she and Judy accompanied Carl as he walked to the mirror. He stared at the reflection of his feet in the sexy white heels. This was the first time he had worn women’s clothing of any kind and he was overcome with emotion. It was daring and provocative and exhilarating. Deep down in his heart he knew this was right. The outlines of his future happiness was just beginning to come into view. If only he could get past Kelly, he would have a lifetime ahead of himself to explore every aspect of his desire to be female. He owed Gail and Judy more than they ever would suspect.

“You’ve got the sexiest feet in those shoes, Carl,” Gail said. “What a pretty look for your legs. Imagine how darling you’ll be with your pantyhose and the sundress!”

“That’s so kind of you to say that,” Carl said, admiring his feet. He stepped away from the mirror and walked around the shoe department until he suddenly remembered that he was a man wearing heels. He hurried back to his seat and looked around to see if anyone had noticed him. While he took off the shoes, Judy and Gail tried on theirs. Carl watched them walking about in the heels. He loved their grace and their easy confidence. He would have to learn to emulate them.

Judy and Gail were happy with their shoes and they decided that this would be the official shoe of their dress-up game, when and if they played it. “Last on the list is to get you some boobs. Judy and I don’t need to buy them,” Gail said, causing Carl to laugh.

“I hope it will further incentivize you to know that the dress-up game always begins with the players being naked.”

“Really. Wow. I swear I’m going to try and see if I can convince Kelly to break up with me.”

“We’re rooting for you, Carl. Gail and I would love nothing more than to play the dress-up game with you!”

They bought the shoes and then rendezvoused at a medical supply shop where Carl – with the help of the ladies – bought DD breast forms.

Carl and the two women had an emotional good-bye before the three of them separated.

“Give us your phone number,” Gail said. “I’ll give you mine. We should keep in touch.”

They exchanged numbers and Carl said, “I’ll definitely call you if I’m available to play the dress-up game. I have some real work ahead of me to sort out my relationship with Kelly. In the meantime, I cannot thank you enough for helping me buy this pretty outfit. I never would have been able to do it without you. Now I have to hurry home to hide it before Kelly comes. If I’m lucky I’ll get to try it on soon. I can’t wait!”

As Carl walked away Gail said, “Call us if you need moral support or any other help. Seriously. That Kelly of yours makes me a bit nervous.”

“Thanks, I will.”

Judy and Gail watched Carl walk away. “I don’t know about him,” Gail said.

“He’s a teacup,” Judy said. “Just the kind of guy we were hoping to find. I’m also worried about him.”

“Unfortunately, there’s nothing we can do until he’s figured out how to get out from under Kelly.”

***

When Carl entered his apartment building and got his mail, there would be about an hour before he could expect Kelly to show up. He took the elevator up to his floor and without thinking headed to his apartment not noticing that Kelly was waiting for him. When he finally noticed her he jumped in surprise and then attempted to partially hide his shopping bag behind himself.

“Here you are, Carl. I’ve been waiting for half an hour. Where were you? You’re always home this time.”

“Nowhere, I just did an errand.”

“What’s in your shopping bag?”

“Oh, nothing.” Carl opened the door and walked in and searched for a place he could inconspicuously place the package.

“Don’t tell me nothing. You went shopping. What did you buy?”

“I can’t show it to you now.”

“Why’s that?”

“It’s a present for you.”

“For what occasion?”

It was far from Christmas, Kelly’s birthday, and the anniversary of the day they met.

“Christmas. The price was good so I decided to get it now.”

“And hold it for eight months? That’s ridiculous, Carl. You might as well give it to me now.”

“I can’t.”

“What do you mean, you can’t?” Kelly’s face rapidly changed toward irritation and anger.

“It’ll spoil the surprise.”

“Carl. You’re lying. I know you well enough to know that you’d never buy a Christmas present early. Hand over the package and let me see what this gift of yours is.”

Carl hesitated and Kelly took the package out of his hand. She reached in and pulled out the sundress. “You bought me a sundress? You’re crazy. I would never wear a girlie dress like this.” She checked the size and said, “Fourteen? I’m a twelve, not that you would know that.” She reached in and took out the bra. “A fucking bra, Carl? You bought me a bra? I would never be caught dead in a fancy bra like this. And it’s a 38DD. Are you nuts? How could you think I was a thirty-eight and a DD? Really. Do I look like a DD?”

Carl had turned white with fear as Kelly now reached in the bag and took out the breast forms. “Tits? Artificial tits?” She stared at him and then said, “Oh my God. This is for yourself! You are about a fourteen and a 38 band width.” She next pulled out the panty, the pantyhose, and the shoes. “A whole fucking outfit. You bought yourself a girl’s outfit!!” She shouted the last part and Carl trembled wondering what Kelly was going to do. He would have run away if he thought he could get away from her.

“I’m sorry, Kelly,” Carl said, and began crying. He watched in horror as Kelly walked over to him and then before he could even raise his arms to protect himself punched him in the face. He fell to the ground holding his face in his hands and crying loudly.

“Now I hope you understand what I think about you lying to me and about you daring to wear girls’ clothing. If there ever is a next time like this, I won’t stop hitting you until I have to call an ambulance. Do you understand, Carl?”

“Yes! Kelly!” Carl called out from the ground.

“It might be hard for you to believe it, but I don’t enjoy hitting you. I wish more than anything else that you were strong enough and manly enough to stop me from hitting you. Indeed, if I had to protect myself from you I’d be overjoyed. I’m filling a vacuum that you’ve created, Carl, and I don’t like it one bit. I’ve been extraordinarily patient with you waiting for you to begin building up your muscles so you have the strength of a man. Now I see that I have to take control of the process. I’m going to turn you into a man if it's the last thing I do. Got it?”

“Yes, Kelly.”

“Good, Carl. Are you ever going to so much as even think of wearing women’s clothing again?”

“No, Kelly. I never, ever, will. I’m sorry. I don’t know what got over me.”

“I’m going to trust you, Carl. Now, get up. We’ll begin your strengthening program right now. Tomorrow I’ll bring some equipment to help that along.”

Carl watched in horror as Kelly gathered up his outfit, put it back in the bag and then dumped the bag into the kitchen trash bin. “I’ll put this down the chute before we go to bed.”

Kelly settled into a chair and said, “Strip down to your boxers.”

Carl took off his clothes and lay them on a chair. “I’ve got too much invested in you Carl. I was mistaken in believing that since you have a dick, you must ultimately be a man. Now I’ll train you into becoming a man. A couple of hours every night. Once your biceps begin to develop you’ll realize how wise I am and how much you’ve benefited and then you’ll be inspired to work even harder. Building muscle is very much self-reinforcing.”

“Thank you, Kelly,” Carl said. He prayed that Kelly would forget about his clothes and not throw the bag down the chute. He was desperate to put on the bra. If he could just get the bra on he’d be so happy.

Kelly barked at Carl, “Get down in a plank.”

Carl lowered himself into plank position. “Hold it, I’ll time you.”

Carl struggled holding the position and then put his knees on the ground. “Twenty seconds, Carl,” Kelly said, shaking her head. “Now do a push up.”

“A push up? Can I do it from my knees?”

“You mean a girls’ push up? Do whatever you can do.”

With his knees on the ground Carl lowered himself until his chin and chest touched the floor. He struggled to push himself back up. With his arms wobbling and sounds of straining Carl managed to get back up.

“Another! Keep going but my God the one you did was pathetic.”

Carl lowered himself down and this time he couldn’t get up. “I can’t get up, Kelly.” Carl felt tears coming on again. All he wanted was to be pretty, to wear the incredible outfit that the kind ladies had helped him buy.

“More tears, Carl? Really? Have you no self-respect? We’re going to have to eradicate all these girl emotions that seem to be warping your mind.”

“Yes Kelly.”

After an hour in which Kelly made Carl do any number of exercises such as jumping jacks, burpees, dead bug she told him to take a shower. “Meanwhile, I’ll dump the trash.”

***

In the morning Kelly announced that she was horny and demanded that Carl make love to her as if he were a real man. “This will be good practice for the day when you actually become a man.”

Kelly made him be on top and to act like he was stronger than her. He did the best he could and Kelly went along with it. His erection was feeble. Just enough to get the job done. He was amazed he had any erection at all since Kelly whispered into his ear the entire time that she was proud of her “he-man.” The image of himself as a he-man turned off his sexual lust. After he finished, he lay in bed as Kelly got up and told him that this evening would begin a regimen of muscle building that would transform him into a desirable hunk.

Carl thanked her at the same time he was thinking, “Gee, thanks a lot.”

“By the way, give me a spare key,” Kelly said. “I don’t want to have to wait outside anymore.”

Carl gave her a key. It was the last thing that he wanted to do, but what choice did he have? She’d get angry and accuse him of not trusting her.

After Kelly left, Carl saw in the bathroom mirror that he had a black eye. There was no way he could hide it from anybody. He’d have to go to work looking like this and everyone would ask him what happened. He’d say it was an accident but no one would believe him. He would have liked Kelly to help him hide it with some makeup but she obviously didn’t care. In fact, she was probably proud of her handiwork and happy that everyone could see how she ruled over him.

Carl got dressed and rushed down to the basement to find the building superintendent. He tipped him to open up the trash room so he could retrieve the garbage that Kelly had thrown down the chute. Luckily, after searching through two dozen bags of garbage he found his clothing. He took the bag back to his apartment and hid it underneath the old, rarely worn clothing in the bottom drawer of his dresser. It was the best hiding place he could think of. He would not be free of worry that Kelly might find his clothes, but he had to take the chance.

***

During the next two weeks Carl descended into a hell of exercise. The day after his blackeye, a group of guys showed up at his door delivering a floor to ceiling “Power Rack.” It was Kelly’s inspiration to enable her to foist as many different exercises on Carl as she could dream up. Carl was sure that the Power Rack was a holdover from the Spanish Inquisition meant solely for torture. For hours Kelly lay on the sofa eating potato chips, drinking beer, and barking orders for Carl to do one exercise or another. If he stopped in between the hourly five-minute rest periods she allotted him, she’d threaten him with a leather riding crop. Another horror of hers was her insistence that he wear a Speedo during his exercises. She had given it to him as a present with a card that said, “To my dear Carl. This is to remind you that you have a penis. Love, Kelly.”

Within a few days Carl could see the handwriting on the wall. Kelly will drive him crazy long before he developed the muscles that she wanted him to have. His fear of her was so complete that despite the pain in his aching muscles, his fatigue, and the now constant desire to wear his sundress and lingerie, he did everything she told him to do. If this life continued he knew inside that he would crack up. A point would be reached that he’d rather have her beat him up than continue with the exercises.

At the beginning of the third week, Kelly made Carl flex his arm muscles. She felt them and said, “God, Carl. I can barely detect a change. Clearly a few hours every night is not enough. I can get permission to go to work late and we’ll add in a couple of hours every morning. That should speed things up.”

“Please, no, Kelly,” Carl said expecting to get hit.

“No?” Kelly laughed. “Carl, you need a reminder. After you get muscles and have the physique of a man then, and only then, will you have earned the right to tell me what to do or to tell me what you want to do. That should be quite an incentive for you to get busy and workout.”

Carl started to cry and Kelly said, “Cry all you want Carl, it has no effect on me.” She ordered him to do some bicep curls and he started it and then stopped and fell to the ground into a fetal position.

“I’ve got to get to work, Carl, so I’ll have to deal with this later. Just be forewarned that the blackeye I gave you two weeks ago is no longer visible. I swear, however, that when I come back tonight, if you don’t resume exercising according to my commands, I’ll give you two blackeyes. How does that sound?”

Carl continued to cry without saying anything. “I’ll take that as an ‘I understand, Kelly’.”

Kelly left and Carl lay for some time on the ground contemplating what he should do. Something had to be done. He had to stand up to Kelly, but she was going to beat him up if he did. Would she hurt him and then leave? Or would she keep coming back and forcing her will on him? He couldn’t keep on exercising and he was terrified of her punching him. He was defenseless. She could easily pull his hands away from his face and give him the blackeyes she had promised him. Carl felt sick with worry. Out of the blue he remembered that he had a piece of paper with Gail’s phone number on it. She had told him to call her if he needed help. Maybe she could help him. He was at the end of the line.

“Carl? What a wonderful surprise. Judy and I have been thinking of you a lot. That fun day of shopping for our sundresses. How are you?”

“Oh, yeah, actually, not so good.” Carl related to Gail how Kelly had found his clothes, punched him, and had forced him to work out every day. In the midst of his story he broke down. Gail was horrified.

“All this time you’ve been going through hell? My dear, dear, Carl. Why didn’t you call sooner? Judy and I are going to intervene. Don’t you worry any more. She and I will take over with Kelly. We’ll take care of you and heal you. Please trust yourself to two women who will provide you with the love and respect you deserve.”

The more Gail talked the more Carl wept. She was saying everything he had so longed to hear. Finally, after Gail listened patiently to him gulping in air as he cried, he finally calmed down and regained his composure. “You and Judy are the most wonderful women.”

“And you are a wonderful boy. Don’t ever forget that. Tonight, when Kelly returns begin your exercise routine as normal. Then at about eight o’clock Judy and I will show up and deal with her.”

“She might try and hurt you two.”

“I’m sure we’re more than capable of keeping Kelly under control.”

“God, I hope so. She’s so mean and scary. I’ve just been so afraid to cross her.”

“Do you need me to come now and comfort you?”

“I’m sorry. I’ll be okay, but please come tonight. I have to start my exercise right after dinner.”

“Don’t worry. Judy and I will come and sort this out once and for all.”

***

That night when Kelly returned she said, “I’m glad to see that you’ve decided to work on your exercises. I was not looking forward to giving you blackeyes.” Kelly laughed.

“Yes, Kelly. I’m going to try my best now.”

“Good. I’m going to make a man of you yet!”

After dinner, Carl began his workout. He was struggling with an exercise when the front door buzzer went off. Kelly said, “keep on working, I’ll answer it.” She got up and went to the door and opened it.

“Hi, you must be Kelly,” Gail said.

Kelly looked at her suspiciously and asked, “How do you know me?”

“I’m Gail and this is Judy. We’re friends of Carl.”

“He never mentioned you.”

“We’re new friends. We helped him buy his pretty sundress and bra and the rest of his outfit.”

“That I threw away? What the fuck? Jesus Christ you’ve got some nerve coming around here!”

“Wait a minute. This is Carl’s apartment, isn’t it. Can we see Carl?”

“He’s busy right now.”

Carl called out from the living room, “Who is it Kelly?”

“Don’t you mind. Keep working out.”

Judy moved to walk around Kelly who lunged at her freeing up Gail to enter into the apartment to where she found Carl wearing only a Speedo and pulling on a wire attached to two small weights. Kelly and Judy joined her. “Don’t just stand there Carl. Lift the weights,” Kelly ordered him.

Carl resumed lifting the weights.

Gail said, “What are you doing Kelly? Where do you get off telling him what to do?”

Kelly laughed. “Where the fuck do you get off coming in here and asking me questions? I’m warning you to not get me riled up. You don’t want to be on the receiving end of my fist.”

“Screw you, Kelly. You’re not talking to Carl now. Just try and take a swing at me. You might look tough picking on a gentle boy like Carl, but that doesn’t work with a real woman.”

“Carl doesn’t need friends like you that dress him up like a girl. That is so perverse.”

“If you weren’t so filled up with yourself you would have noticed Carl’s feminine side.”

“Give me a break. Carl shouldn’t even have a feminine side. He’s a guy in case you haven’t noticed.”

“Like I was saying. You are so blinded by your closed mind you can’t even see the obvious. He’s not your boyfriend, he’s your prisoner. He’s so scared of you that he obeys you so as not to have to face your anger.”

“Carl needs guidance on how to become a man. He grew up mostly without a father and never had to confront the fact that he needs muscles to go along with his penis. I’m doing him a wonderful service that he’ll spend the rest of his life thanking me for.”

“That’s you and your prejudices. It has nothing at all to do with the real Carl.”

“He can’t even look you in the eye. He’s trembling. He’s afraid you’re going to yell at him causing him to cry.”

“So what? Some men need the discipline that a smart woman can provide them. Carl is my project. By the time I’m done with him, he’ll have a beautiful manly physique. It’s what he should have had years ago.”

“This is where you’re looney tunes,” Judy said. “Carl is practically a girl both emotionally and physically and you want to make him masculine? What a joke!”

“Come back in six months,” Kelly said. “He’ll have biceps that’ll give you an orgasm.”

Gail and Judy laughed. “What are you smoking Kelly? Look at Carl’s arms. The three of us have stronger arms than Carl. He has girl arms. Obviously, he was born with a low testosterone level so it’s really hard for him to develop muscles.”

“He’s as feminine a guy as you can find,” Judy said. “I guarantee you he’s mortified to be wearing a Speedo. How did you ever force him into one of those. I’m quite sure he’s wishing he were wearing panties.”

“He has a penis! He’s a man. It’s that simple!” Kelly said.

“Bullshit,” Gail said. “A penis doesn’t make a man. Carl has wanted to wear a bra since he was at least thirteen years old. It’s who he is. His penis doesn’t define how he sees himself. Your beliefs are archaic. If you had any understanding of modern science you’d accept the fact that you’re never going to turn Carl into a man. In the process of trying to do so, you’re destroying him. If you only knew how unhappy you’ve made him.”

“How can you not like being a man?” Kelly said to Carl.

Carl began to cry and collapsed to his knees in front of Kelly and grabbed onto her legs.. “I’m so sorry Kelly, but I want to wear my panties and a bra. I want my pantyhose and breasts. I want my sundress. I want to look like a girl.” He sobbed as he clung to her.

“Judy and I found him at Macy’s desperately wanting to buy a sundress and we thought we would do a good deed and help him look like the girl he wants to be. Talk about a fish taking to water. If you could see how happy Carl was buying his underwear and dress you’d never try to do what you’re trying to do.”

Kelly said, “As I said, I threw out his dress, underwear, breasts and shoes.”

“Carl so loved that outfit,” Gail said.

Carl blew his nose and regained his composure. “I’m sorry Kelly.”

Kelly shook her head and said, “I don’t see any way forward. I truly don’t like hitting Carl. I thought by doing so it would help him. I’m still not sure that I believe the two of you, but I also no longer believe that I can make him a man.” She sat down and held her head in her hands.

“I’m really, really sorry, Kelly. I just can’t be the man you want and need. If anything I’d like to be like you.”

“Enough, Carl. I don’t want to hear about how you wish you could wear my bra and panties. No, no, no. You guys win. I’m out of here.” Kelly got up.

“I’d still like to be your friend,” Carl said.

Kelly laughed. “We’ll see. I know that I’m not going to want to see you dressed as a girl. It’s probably best if we don’t plan to see each other again. If it turns out otherwise, then so be it. We’ll deal with it then.”

Once Kelly left the apartment, Carl broke down in utter mental and physical exhaustion. “You’ve saved my life!”

“You poor dear. Women like Kelly can be pretty scary. Happily, you’ll be safe with Judy and me. You did the right thing by asking us to come rescue you. You’re ill equipped to stand up to women. There’s no shame in not being able to. No doubt it’s self-preservation that has taught you to be deferential to women and especially to not tempt fate by resisting them.”

“Thank you so much.”

“Judy and I hope that you’re still interested in playing the dress-up game.”

“More than ever!”

“But Kelly threw away your outfit.”

“She did, but I was able to retrieve it from the garbage room downstairs. I wrapped it up tightly and put a lot of tape over it and put it in the bottom of my lowest dresser drawer.”

“How clever of you! Then we’ll play it this weekend.”

“Would the two of you stay with me a little longer. I’m a little scared that Kelly might come back.”

“Sure. We can stay awhile. Kelly left her key on the table so I’m pretty sure that she really doesn’t intend on coming back here.”

“Oh, that’s good to hear.”

***

Saturday morning Carl arrived at Gail’s apartment carrying his sundress and other clothing. The ladies ushered him into Judy’s bedroom where they sat on the bed. “Let’s get started,” Judy said. “Remember, Carl. The dress-up game is fun only. Fun and craziness!”

“We do everything together is the only rule,” Gail said. “We take off our clothes together, then we each put on our panties, then our bras until we’re fully dressed again. After that we style our hair, put on makeup and nail polish. Always the same for each of us.”

Gail unzipped the back of her sheath dress and lifted it up and over her head. Underneath she was wearing a white bra and panty. Carl began unbuttoning his shirt and taking it off. Judy pulled her top off over her head revealing that she was wearing a wine-colored bra. She began undoing the button and zipper of her skirt. She stepped out of it revealing panties that matched her bra. Carl gawked at the two women wearing just bras and panties.

“I think Carl’s eyeballs are going to pop out of his head,” Judy said.

Turning red Carl said, “I’m so sorry. You two are so beautiful in your underwear. I’m just dying here – the sight is so amazing!”

“You’ve seen Kelly and other girlfriends in their underwear, haven’t you?”

“I know, but they were always kind of circumspect about undressing in front of me.”

“Let’s see you in your underwear.”

“Right, I’m sorry. I got a bit carried away.” Carl unbuckled his belt buckle and unzipped his fly and his jeans fell to his ankles. He was wearing blue boxers. “I’m so sorry about the tent. I knew it was there but I was hoping that it wouldn’t be this noticeable.”

“Don’t give it a second thought,” Judy said. “It’s nice to know that you’re enjoying yourself. We certainly are.”

“Now we’ll step out of our underwear,” Gail said.

Carl watched in awe as Gail and Judy lowered their panties to their ankles and then reached behind their backs and unhooked their bras. The sight of their bushes and full breasts gave him an insane desire for the women. He wished he could sink on his knees and gently rest his face against their pubic hair and feel it tickle his nose. There’d be a delectable womanly scent that would intoxicate him. He was knocked out of his reverie by Gail telling him to lower his boxers.

He pulled them down releasing his very unladylike boner for Gail and Judy to inspect. “My goodness, Carl,” Gail said.

“Oh, Gail, I’ve died and gone to heaven!” Judy said.

“You’re sure this doesn’t ruin the dress-up game?”

The women laughed. “It’s a nice addition to the game,” Gail said. “Isn’t it, Judy?”

“I’ll say. I’m quite pleased with what I’m seeing. In the length and thickness department you get high grades.”

“Besides that, you’ve got an attractive one. The shape is harmonious. The balls are well proportioned and symmetrical. All in all you should be proud of your equipment.”

“Gosh. No girlfriend of mine ever said that before.”

“Perhaps they were worried about giving you a swelled head,” Judy laughed.

“What I’m seeing here should have been enough for Kelly without wanting you to have muscles,” Gail said. “I think that the quality of your appurtenance more than compensates for you having a girlish physique.”

“You’re making me feel so desirable!” Carl said.

“You’ve got that right! Don’t blame us if the end of the dress-up game involves a bit of nookie!”

“Really?” Carl said. He just then saw what was a part of the dress-up game that he hadn’t thought about.

“When people who like each other are affectionate, sparks may fly and one thing leads to another. Is that a problem for you?”

Gail and Judy listened intensely for Carl’s answer. The whole rationale for playing the game hinged on his interest in nookie. “Hardly,” Carl said. “I want to do whatever you ladies would like me to do. I’m yours if you’ll have me!”

“We will have you. You’re adorable, Carl,” Gail said. “Judy and I treat our property with the best of care. You’re in very good hands.”

“So let’s begin the dress-up game! Panties on!” Judy said.

Gail and Judy stepped into their cute panties causing Carl to lose focus once again.

“Come on, Carl. It’s panty time,” Gail said.

“Sorry.” Carl put his feet in the panties and as he pulled them up he wondered what he should do with his boner.

He tried tucking it into the delicate panty until Judy said, “Just leave it pointing up.”

“Yeah, but that exposes the sensitive side.”

“Is there a problem with that?”

“No, I guess not.”

“Our pantyhose is control top so it can force your boner down if you want to do that.”

“Great. That might do the trick.”

Carl pulled up his panties with his member pointing toward his belly button. A charge of sexual feeling swept through him.

“Turn around so we can see your cute butt in the panties,” Gail said.

“Oh God, it’s so pretty!”

“Your butt has a marvelous shape. It’s quite girl-like even if a tad small.”

“Thank you,” Carl said. This was thrilling news.

“Now our bras!” Judy announced. “Carl will at long last get to wear his very first bra.”

“A milestone in any girl’s life!”

“I’ve wanted this day to happen for so long.”

“I went through the same feelings when I was eleven and twelve,” Judy said. “Praying and praying that God would give me boobs so my mom would let me wear a bra.”

“And then Bada Bing, you’re a DD cup!” Gail said laughing. “I went through that also.”

“Luckily, Carl doesn’t have to slog through A, B, C, and D. He can start at DD!”

“Let’s put on our new bras together,” Judy said. To Carl she said, “Imitate each of the steps that Gail and I do and you’ll end up with your bra on correctly.”

Judy and Gail divided their bra dressing into a few small steps that Carl was able to follow and before he knew it he was dressed in a bra and panty.

“Can I insert my breasts?” Carl asked.

“Of course!”

Carl fetched them and placed one life-like breast in each of his bra cups. “Oh my goodness. I now know what a girl feels like wearing her first bra. It’s like my girlhood has been switched on. My pretty chest is emitting femininity in every direction like a lighthouse.”

“You are if nothing else, poetic,” Gail said. She and Judy came to either side of him and put their arms across his back. Carl compared his chest in the pretty bra with those of Judy and Gail to his sides. For all intents and purposes they looked the same.

“I’m speechless,” Carl said. “My chest looks just like yours.”

“Isn’t that wonderful!” Judy exclaimed. “It’s what happens in the dress-up game. We dress the same, we look the same, we feel more and more the same.”

“Panties. Bras. Now our pantyhose!” Gail said

“I’m going to need a lot of help,” Carl said.

“We’ll lead you through it slowly and carefully,” Gail said. “Relax and take a deep breath. One false move and you might get a run in your stocking.”

“Oh my God!”

“Gail is teasing you Carl. We do have to be careful not to cause a run, but runs are not as difficult to avoid as Gail is pretending.”

Gail showed Carl how to roll up one of the legs so that it could be slipped over his toes and pulled up carefully to his knee. Then he rolled up the other leg and put it on his other foot. “Make sure you don’t lose the alignment or else your pantyhose will twist going up your leg and feel uncomfortable.”

Carl got his pantyhose up to his knees and the ladies guided him to stand up and gently roll the pantyhose up to his crotch and then carefully over his buttocks and finally to his waist. He reached inside the pantyhose and rearranged his penis to point down making a smaller bulge. “You can even do a little dance pulling on the waist and lifting your legs to get them fully on.”

Carl imitated Gail and Judy until the three of them had their control top pantyhose on. “The pantyhose really helps keep my boner out of view!” Carl exclaimed.

“It acts similarly to a girdle. My son figured that out.”

“Your son?”

“Yes, my son, Greg, and Judy’s daughter, Jill, play the dress-up game with each other.”

“Oh. These are your kids that you mentioned to me before?”

“Yes,” Gail said.

“So one of them is your son Greg. He dresses like a girl?”

“Yes, indeed. He’s actually quite pretty. He and Jill are absolutely darling together. They have accumulated quite a few matching dresses, besides many identical sets of bras, panties, and the prettiest panty girdles.”

“Your son has boners that he hides inside his girdles?”

“Yes. It was quite clever of Jill and him to figure that out.”

“Carl should meet them one day,” Judy said. “Even though Greg is just thirteen, the two of you have a lot in common. You could give each other moral support as you explore your feminine sides.”

“Definitely,” Carl said. “Greg seems like a very special boy. It would be fun to talk to him about playing the dress-up game.”

“Good! Now I believe we’re ready for our sundresses.”

“First let’s look in the mirror. Three ladies dressed in identical panties, bras, and pantyhose.” They stood in front of a full-length mirror with Carl in the middle. “Turn!” Gail said, and they rotated around and looked over their shoulder at their three tushes in the pantyhose and the bra strap running across the middle of their backs. Carl’s pantyhose covered tush was not as full and womanly as those of Gail and Judy, but it could be taken to be the rear end of a slender girl.

“Let’s put on our sundresses and heels!”

Carl put the sundress on over his head and Gail zipped him up. Then he helped zip up Gail and Judy. They each put on their heels and assembled again in front of the mirror. Carl was floored by how sexy they looked. Their large breasts seductively pushed out the front of their dresses while the three pairs of shapely legs in pantyhose and stylish white heels formed a beautiful mosaic of femininity.

“My God, I’ve become a woman like you two.” Carl’s voice became husky as if he were fighting the impulse to cry.

“Get your crying done, Carl, because it’s time for our makeup and we’d hate for your tears to cause your mascara to run,” Judy laughed.

“I’m sorry. I’m a mess right now. I’ve wanted this for forever and now you kind ladies have helped me to make it a reality. I don’t know how I can ever repay you.”

Judy and Gail gave each other a knowing look. They had no trouble imagining ways that Carl could repay them. In fact, before this day was over they were pretty sure that he’d be making a down payment on his debt.

“Now, the next thing we need to do is work on the same makeup, the same hair style, and the same nail polish color. When we’re done we’ll be three identical girls!”

“And we can bask in our beauty!”

After much discussion Gail and Judy came up with a makeup scheme that showed off everyone’s feminine features including Carl’s. His long straight hair was readily styled to match the way the women groomed their own hair. The ladies applied nail polish to Carl’s fingers and toes and then the same shade to themselves. With the transformation now complete Carl exulted in the endless delights of the dress-up game. He sat with Gail and Judy on a sofa and posed for photos in which they all took the same positions. Legs crossed showing their pantyhose and heels, knees together and legs at an angle. The more they carried on in their dress-up game, the more interchangeable Carl felt with Gail and Judy. By looking like each other, they truly became each other. A closeness formed between them that increased hour by hour until Carl was no longer sure that he was a man. His need to imitate the movements, voice and personalities of Gail and Judy overwhelmed him and brought him to a feverish pitch of happiness and contentment. He was giddy with being a girl and couldn’t contain his joy. “I’m Carla, I’m Carla,” he cried out and Gail and Judy hugged him.

As Gail had predicted, the dress-up game at its apex unleashed primal desires in the three of them that led inevitably to first stripping away their sundresses, pantyhose, and heels and then, secondly to fulfillment of their carnal passions. For Carl, the two lovely and amply filled bras of Gail and Judy were manna from heaven that he feasted upon. The ladies for their part indulged themselves in the perfectly formed erect symbol of Carl’s state of mind. In short order the soggy end of the festivities was reached leading to smiles all around.

Carl being Carl, it didn’t take long for him to realize how vulnerable he now was. He needed the dress-up game to be a part of his life. How could he ever go back to his life before the dress-up game? “Gail and Judy?” Carl said timidly after they had rested for some time.

“What dear?” Gail said.

“Do you think there are any other boys like me?”

“Of course there are. Remember my son, Greg? Why do you ask?”

“I was thinking that you might decide that I’m a freak of nature and not want to play the dress-up game again with me.”

“Carl, you have way too active an imagination. I think your time with Kelly has made you feel insecure and vulnerable. You have to learn to accept yourself for who you are and most importantly to respect your own uniqueness.”

“So we will play the dress-up game again?”

“Yes, of course we will,” Gail said.

“It can be played more than once?”

“There’s no limit on how many times.”

“We should introduce Carl to Jill and Greg,” Judy said.

“That’s a great idea. If you met our kids who have been playing the dress-up game for a couple of months already, you’ll realize that it never gets old and that you’re definitely not the only boy who enjoys playing it.”

“I would love that very much.” Carl gave them both a hug. They could hear a faint sniffle as if he had been crying. Gail and Judy smiled to themselves. How lucky they were to have found this dear boy. He needed them and they reaped many delightful feelings from his delicious body.

“What dress will we wear for the next time we play?”

“I was thinking we should wear little black dresses. You know, cute little dresses that women wear to cocktail parties. The dresses will be tight and show off our curves. We’ll get new bras and panties and pantyhose. We’ll need some gold bracelets on our wrists, and earrings. We’ll have to get your ears pierced. Our shoes will be very high, black, patent leather with spike heels.”

“And a cute handbag on a gold chain.”

“Exactly. What do you think, Carl?”

“Sure. Wow. That sounds really exciting. I never thought about dressing like that.”

“Then it’s settled. One evening this week we’ll do our shopping and get you pierced. Then we’ll meet next week at Gail’s apartment. You should spend the night with us.”

“The night?”

“Yes. Greg and Jill sometimes play the dress-up game over night. They have the cutest pink pajamas with red hearts all over them. While they’re sleeping in their bedroom, we can have our own sleep-over in my bedroom. We’ll buy three cute baby dolls that we can sleep in. It’s still the dress-up game, and a perfect end to the day.”

***

A week later Carl came to Gail’s apartment to both meet Jill and Greg as well as to play the dress-up game again. When he arrived in the afternoon Gail said, “I’m so glad you’re here. The kids are playing the dress-up game themselves. They bought some new dresses and underthings during the week and they’re just now getting dressed in Greg’s bedroom. I thought that we should retire to my bedroom and change into our dresses. By the time we’re dressed so will the kids and we can introduce you.”

Carl and Judy followed Gail to her bedroom. He liked the tradition of starting out naked and getting dressed together in unison. They had bought black bras and panties, ultra-sheer pantyhose in a shade with a hint of black, and black patent leather stiletto heels. After they undressed, they put on their panties, then their bras, then their pantyhose and finally their dresses. Each step of the way Carl felt the excitement growing. When they had on their identical little black dresses Carl was overcome admiring the medley of pretty curves formed by their boobs, rounded and smoothly protruding rear ends, and graceful stockinged legs. Carl sat down with Gail and Judy while they did their makeup, put on their jewelry and heels.

The spike heels fascinated Carl and he was smitten with the feminine look they gave to his legs. Walking in them was a bit of a challenge but the sight of his stockinged legs sitting in the elegant heels helped him feel like he was one with women everywhere. Gail, Judy, and Carl took selfies and admired themselves in the mirror. “You’ve made me so happy,” Carl said.

“You’re a honey, Carl. You deserve all the happiness you can get. What’s more, your happiness is our happiness. You’re without a doubt the loveliest playmate that Judy and I could hope to find. Isn’t he, Judy?”

“So true. In every way, Carl, you’re a delight. You bring out our instincts to nurture and protect you. Your feminine nature is so heartwarming, yet as we’ve seen you’re a perfect companion in bed with us. Gail and I have the best of both worlds with you.”

“I’m overcome,” Carl said, and the three of them hugged.

“I think I hear Greg and Jill out and about, so let’s join them.”

Carl nervously followed behind Gail and Judy as they walked to the living room. He did his best to sway his hips and act as womanly as Gail and Judy. Imitating them, was after all a goal of the dress-up game.

Carl did a doubletake when what appeared to be two young girls in identical party dresses entered the room. “This is my daughter Jill and her boyfriend Greg, Gail’s son,” Judy said, “and this is Carl. Gail and mine new friend.’”

“Nice to meet you,” Carl said.

“We’re so very pleased to meet you,” Jill said.

“Very much so,” Greg said.

Jill and Greg sat down on the sofa side by side and Jill put her arm across Greg’s back. Carl sat in a chair across from them. Gail and Judy had coached him on the proper way for a lady to sit in a tight dress. He enjoyed having an opportunity to show his skill as he gracefully sat, sticking out his tush behind him and keeping his legs together. “This is a great opportunity for the three of you to get acquainted while Judy and I prepare dinner.”

When Gail and Judy left, Carl said, “I can’t get over how pretty the two of you are.”

“I agree with you that Greg is so very pretty,” Jill said, laughing. She leaned in and gave him a kiss on the cheek.

“You’re making me blush,” Greg said.

“He’s so pretty,” Carl said, “I was sure he was a girl when I entered the room.”

“I wouldn’t look like a girl if it wasn’t for Jill,” Greg said. “She’s so smart in knowing what adds to my femininity.”

“Your mothers are doing the same for me. I’m amazed at how well they can bring out my girl side.”

“You look very sophisticated and pretty in the little black dress. It’s so nice that you like the dress-up game,” Jill said.

“Thanks,” Carl said. “It was clever of you two to invent it.”

“Just like there’s a girl inside Greg’s body, my mom thinks that there’s a girl inside you,” Jill said. She gave Greg another kiss on the cheek.

“See how Jill gives me little random kisses on my cheek. She’s making sure that I feel loved and appreciated for dressing the same as her.”

“It’s an important part of the dress-up game to make the boy feel confident being a girl,” Jill said.

“Your moms are doing the same for me. They often remind me that I look pretty and that I’m behaving like a girl.”

“They’ll start giving you little kisses to remind you of their affection for your dressing like a girl.”

Carl laughed, “I hope so. That will be nice.”

The conversation paused for a minute until Carl said, “Gail and Judy thought that it would be good for me to meet Greg. I didn’t know that there were other boys who wanted girls to see them as being feminine.”

“That’s a nice way of describing Greg,” Jill said. “He really appreciates the fact that I see him as being my girlfriend or little sister. He needs me to guide his female impulses which I am more than happy to do.”

“You see how amazing Jill is?” Greg said. “Without her I was really confused and mixed-up as to what I am. I felt desires to be a girl and dress like a girl, but it wasn’t until Jill took control of my feminine needs and desires that I began to understand myself, especially what my role should be.”

Jill laughed and said, “Greg’s role is as my pet.”

Greg laughed, “I think she’s right about that.”

“You two are amazing,” Carl said. “I think Gail, Judy and I will have a similar relationship as you two have. The dress-up game is teaching me how to be more like them every time we play. I hope that means that in time I’ll be a very polished and proper young lady companion to Gail and Judy. I love how they’re providing a nurturing home to my feminine side.”

“I’m glad that Carl and I get to share these feelings with each other,” Greg said. “I think it’s neat that we both feel the same way. We can give each other moral support!”

“Exactly!”

They chatted for a while and Carl said, “Gail and Judy said that the two of you like wearing girdles. Is that true?”

“Yes, we do.”

“I haven’t yet worn a girdle. I’m curious about them.”

“Would you like to see our girdles?” Jill asked.

“Sure, if you don’t mind.”

First Jill and then Greg lifted up their skirts to reveal the girdles they were wearing.

“Wow, those are very pretty girdles. I didn’t know girdles came in such pretty designs and colors.”

“I know,” Greg said. “When I first saw a girdle across the room in Ms. Rutherford’s shop I immediately fell in love with it. Jill loved it also. Since then Ms. Rutherford has introduced us to many other pretty girdles. You and our moms ought to wear a girdle. Besides being pretty, they provide a very comfortable but snug fit. I really like them. With the girdle, Jill and I get to wear some really nice designer stockings.”

“I noticed that your stockings are amazing.”

“Yeah. They’re fully fashioned French heel. There are lots of nice styles we can get. Our moms order them for us from Secrets in Lace.”

“I’m wearing ultra-sheer control top pantyhose with my dress,” Carl said. “They’re nice. They feel great on my legs. The control panty is a bit like a girdle according to your mom and Judy.”

Greg turned to Jill and said, “Maybe we ought to wear pantyhose, it sounds like it could be fun.”

“Sure, Greg,” Jill said. “We’ve been so focused on our girdles and garter belts that we haven’t thought of wearing pantyhose. I’ve worn it myself just a few times. For special occasions. The next time we play the dress-up game we’ll wear pantyhose.”

“Great, Jill,” Greg said.

“If we get control top, that can control your you know what,” Jill said.

“That’s exactly why Gail, Judy, and I chose control top!” Carl said.

“Yeah, these awful bulges that we get have to be stifled. The girdle really works well,” Greg said. “I suppose that control top pantyhose does the same thing?”

“It can. The control top really helps reduce my bulge.”

“Girls are lucky they don’t have to deal with them,” Greg said turning to Jill.

Jill hugged Greg and gave him another kiss on the cheek. “You’re a pretty girl in every other way.”

“Thank you. What dresses are you going to choose for the next time you play the dress-up game?” Greg asked Carl.

“I’m not sure. I love watching Gail and Judy figure that out. I’m open to anything. I love wearing dresses. I don’t care if I never wear pants again.”

“I feel the same way,” Greg said. “Dresses are so much nicer. First of all they can be pretty.”

“That’s so true,” Carl said.

“They also give Greg an opportunity to wear his favorite crinolines and have a full skirt,” Jill said. “He looks so cute like that. He’s really a darling.” Jill gave him another kiss on the cheek.

“Jill loves crinolines also,” Greg said.

“I do. They allow a girl to be totally a girl.” Greg and Jill laughed at what must have been an inside joke.

“I saw the crinoline sewn into your dresses when you showed me your girdles.”

“Right. That’s one reason we love this dress. It’s got built in poof.” Greg lifted up his skirt again showing off the crinoline.

“My mom showed me the pretty bra and panty set that you wear with your sundress,” Jill said.

“Yeah. That was my very first bra. I’m still pretty excited about wearing bras, but that first time I put on a bra was a very special moment for me.”

“First bras are also a big deal for girls,” Jill said. She laughed and said, “Greg’s first bra was his mom’s.”

“Yeah, I snuck one of my mom’s bras to wear. I’ve confessed my crime to my mom and she’s forgiven me though she does understand why I wanted to wear it.”

“What was the first bra you wore that was yours?” Carl asked.

“It’s my bra that’s identical to the one that Jill bought for her cousin’s wedding. That started the whole dress-up game. I still love wearing that bra. It’s very special to me.”

“What size bra do you wear?” Jill asked Carl.

“I’m a 38DD,” Carl said. “Both your mom’s wear 36DD. They thought it important that I be pretty close to them in size.”

“I’m just a 36D myself,” Greg said.

“You boys are so funny. What do you mean, by ‘just a 36D?’ I’m only a 34B!”

“Yes, but that’s just for right now,” Greg said. “By the time you’re done developing I’ll be lucky to be as big as you.”

“I was just teasing you boys. It’ll be great if I become a D or DD since then Greg and I will be closer together and we’ll look that much more identical when we play the dress-up game!”

“The bottom line is that it must be really nice to have breasts so that you have to wear a bra. For me and Greg too, it’s nice that we get to pick our cup size so that we can fill our bras and feel like we have very much lady-like chests.”

“I agree with Carl,” Greg said.

“And I’m so happy that you guys like having nice breasts and wearing bras!” Jill said.

“I was wondering if you could show me your dress collection,” Carl said. “Your moms said that you’ve been playing the dress-up game for a couple of months and have accumulated a number of pretty dresses.”

“Yes, we have quite a few nice dresses. Jill and I love nothing better than to go shopping for new underwear, dresses, shoes, and accessories.”

“I can imagine how much fun that must be. I met Gail and Judy at Macy’s and we shopped together. It was like a dream come true for me.”

We’ll be happy to show you the outfits that Jill and I wear,” Greg said.

“Great. I’d love to see them.”

Carl and Jill followed Greg to his bedroom. Entering the room, Carl exclaimed, “Wow. I love how you’ve furnished it. It looks like a teenage girl’s bedroom.” On the wall was a framed picture of Van Diesel. Heart shaped cushions were on the bed with embroidered phrases like “Cutie Pie.” Pink and white colors dominated the walls, carpeting, and other furnishings. Carl noticed a complete set of Little Women and Anne of Green Gables in a bookcase.

Jill laughed. “Greg modeled it on my bedroom. I’ve been helping Greg to transform his bedroom into one that a girl would have. I use my own as a template.”

“Yeah, but I really want my bedroom to be identical to Jill’s. Down to the smallest detail.”

“You’re so sweet, Greg,” Jill said and gave him another kiss.

“So you two dress alike and have the same girl’s bedroom,” Carl said. “I can’t think of anything more perfect.”

“I know,” Greg said. “I feel so lucky that Jill encourages me to dress like her and live like her. I’ve been trying to learn how to walk like her and even talk like her.”

“I hope that one-day Greg will even think like me. Think the same thoughts at the same time. It would be so cute.”

“That’s so cool. There are lots of things about your moms that I’d like to emulate. I hope as time goes on I can learn to be more like them. They have a strength that I wish that I had. Anyway, you were going to show me some of your outfits.”

“You can see from the dress that Greg and I are wearing now, that we’re on the same page as far as pretty dresses are concerned.”

“You both like pink. I like pink also. It’s always been my favorite color.”

Jill smiled and laughed slightly. “It’s such a nice shade of pink. We love these little ribbons and lace touches.” She gently ran her fingers over them on Greg’s dress. “Of course as you saw when we lifted our skirts, the dress has a little stiff crinoline sewn in underneath that helps puff it out a little.”

“I really like that feature. I hope that Gail and Judy will want us to wear a dress like that.”

“That’s the fun of the dress-up game. You can change the look every time you play. Sometimes Greg chooses our dress and sometimes I do. This is one that he really liked. Of course, I happen to like it also. But a couple of times one of us picked a dress that was not a favorite of the other. The game was still fun anyway!”

“Here are all of my dresses,” Greg said. He opened up the sliding doors of a long closet exposing a rack with a dozen or more dresses.

“Wow,” Carl exclaimed. “What a collection of pretty dresses. I’m jealous of you already!”

Greg took a dress off the rack and held it up for Carl. “This is the dress that Jill and I wore when we invented the dress-up game.”

“For your cousin’s wedding.”

“I realized that Greg loved the dress and pretty underwear. At the same time I realized that I really wanted to see Greg wearing pretty underwear and the dress. So it all fell into place, didn’t it, Greg?”

“Yeah. Jill prefers boys who enjoy being pretty. I really like being the kind of boy that makes Jill happy. I want to have all the feminine traits that she wants me to have.”

Greg put the dress back and took out a pleated tartan skirt accompanied by a white oxford blouse. “This is my Catholic school girl uniform,” Greg said. “We got saddle shoes and socks and white panties and we both dressed up as if we were going to parochial school.”

“We had a blast,” Jill said. “We even had identical necklaces with a gold cross that hung just above our bras.”

While Carl looked through the dresses, Greg said, “There’s a couple of shifts and A-line dresses.”

Carl pointed to a dress and asked, “What’s that one?”

“It’s my Rockabilly dress. We wear that with a large poufy crinoline.” Greg pointed to the crinoline on a hangar. “This is such a dynamite outfit. We wore it sitting side by side on the sofa. Our tulle was flying around everywhere and we had such a challenging time holding down our skirts. It was hysterical.”

“Then we got up and danced to some records. What a great time we had!”

“That’s so cool. There are so many nice dresses here,” Carl said. “Many great ideas that I need to pass by Gail and Judy.”

“Take a look at Greg’s underwear drawer,” Jill said.

“Yeah,” Greg said and he opened the top drawer of his dresser. “See how many bras and panties I’ve gotten. There’s also a few garter belts and girdles. Also stockings.”

“Show Carl our bodysuit,” Jill said.

“Yeah,” Greg said, and he took it out of the drawer and handed it to Carl. “Ms. Rutherford and Jill thought I would look really cute in this new bodysuit made by one of her favorite companies.”

“As you can see it’s so ultra-feminine that it’s perfect for Greg,” Jill said. “The fabric is opaque with swaths of geometric lace at the cups, legs, and back. The straps are made from lace, and see the lovely rose gold jewel at the front. Ms. Rutherford said we can wear it as a seductive top underneath a trendy blazer! As soon as we get our blazers we’ll play the dress-up game with the bodysuit.”

“I’m jealous,” Carl laughed. His imagination was running away with him. In time he, Gail and Judy will have to try all these wonderful directions in the dress-up game.

***

Gail announced that dinner was ready and they gathered together in the dining room. Judy, Gail and Carl in their sexy little black dresses and Greg and Jill in their pink, poufed, party dresses. It was a table of females to any casual observer. Somewhat odd because of the identical dresses but otherwise a table of women and girls sharing a meal together. Carl surveyed the table and felt overjoyed to be part of this. To belong to this group of wonderful people. He laughed to himself thinking that they looked like a full house in a poker game. Three black cards and two pink.

When dinner was over and before Gail brought out dessert, she said, “It’s so nice that Carl and Greg are together so that us ladies can express our appreciation to them. Two boys that embrace their feminine personas and bask in the approval of females. They pursue femininity through their clothing, their actions, thoughts, and emotions and thrive in the care of strong women who appreciate their vulnerabilities. The dress-up game, so well created by Jill and Greg, provides a framework within which Greg and Carl can mimic us and by doing so become as girl-like as they can be.”

“Hear, hear!” Judy said.

“Yay, Greg!” Jill said.

“Yay, mom, Jill, and Judy!” Greg said. “When Jill first told me that she’d like me to wear a bra, panties, and pretty dresses, I saw that she was allowing me into her girls’ world. Each week she’s brought me deeper into this feminine place helping me to become more confident of my own femininity. I’ve become Jill’s protégé and will always look up to her and emulate her.”

Jill put her arms around Greg and hugged him. It was beyond cute to see the two young teenagers dressed in identical party dresses holding each other so delicately. Greg had blossomed into a replica of Jill. Of that there was no doubt.

Carl looked at Greg and said, “I’m following along in Greg’s footsteps. I know what he means about entering a woman’s world. Gail and Judy have let me in to a place that I’ve wanted to be for so long now. I hope we’ll get to play the dress-up game many, many times so I can keep on learning how to be a woman just like they are. I hope I never disappoint them by not acting as feminine as they want me to act.”

“That’s so sweet, Carl,” Judy said. “You haven’t disappointed us and I’m certain you never will. Your transformation into a lovely girl grows more complete with each passing day.”

***

Carl helped Gail and Judy clean up after supper. When they were done they joined up with Greg and Jill in the living room where they played games together. When it got late, Jill and Greg retired to their room. A short time later they came out in the most darling identical pajamas and gave everyone kisses goodnight. Carl was choked up with how affectionate the two kids were. When the kids left, Gail said that it would be a good time for the three of them to retire to her bedroom.

Carl, Gail, and Judy slipped out of their heels, their little black dresses, took off their black bras, pantyhose and panties and stepped into the shower together. Gail and Judy took the opportunity to reacquaint themselves with every part of Carl’s anatomy while he struggled to maintain some self-control. Despite the ladies insistence that he soap up their breasts and pubic areas, he somehow made it out of the shower keeping his boner intact.

After Gail dried him off with a large, soft, pink towel, she handed him a pink bra to wear and a pink filmy negligee with matching panty. He eagerly dressed and admired the fact that his bra was visible through the delicate fabric. When the three of them were dressed, Gail went to the kitchen to get some treats while Carl and Judy found a movie to watch. The three of them cuddled up in the bed with Carl in the middle.

As they watched a movie, Gail and Judy took turns holding Carl, kissing him, and otherwise fondling whatever parts of him they desired. Carl basked in the intense physical pleasure while his hands roamed the bodies of the women. Much of the time he was distracted by the beautiful imagery of Gail and Judy in the baby doll.

When at long last Carl lay quietly with sleep overtaking him, Gail, and Judy to either side of him whispered to each other in the dark. “What a lovely boy we found.”

“I’ll say. We really lucked out.”

“He’s a darling. So appreciative of his pretty clothes.”

“So hungry for the love of strong women.”

“Women that see the girl that he is.”

“True that.”

“What should we do for our next dress-up game?”

“You know Jill and Greg are thinking about wedding gowns.”

“Really? Then we should do bridesmaid dresses.”

“I have a feeling that Carl is really going to love that.”

The End