Gerald and Joan

By Pamela

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Another dinner party to go to Gerald thought. At the Webster's house with the Mason's and maybe one or two more couples there as well. Joan had just finished taking her shower and now they would be getting dressed to go. Gerald wanted to put on his blue suit for the occasion but he had his doubts that Joan was going to let him. No, she had other ideas as to what he should wear so there was no point in dressing until she told him what that was. Joan stepped into the bedroom with her hair drying in a towel and said, "You're waiting to see what to wear? Good. So I thought tonight you'll wear the pretty embroidered white dress I bought for you." She opened the dresser drawer and said, "here are white panties and a bra for you to wear and some nice pantyhose."

"Do I have to Joan? Why can't I wear my blue suit and be like the other men?"

"No, I like you being pretty when we go out with friends."

"I know, but the Websters and Masons have never seen me wearing a dress before and there will be other men there that I’ve never met. I know they'll make fun of me behind my back."

"No one there will be so bigoted as to make fun of a man wearing a dress. Just ignore them and smile, Gerald. You can always just tell them that I made you wear the dress."

"It's not just any man wearing a dress, it's me. Someone they know. That's why they'll make fun of me because they know me."

"Sounds like you have a real problem, Gerald. Oh, and I forgot to mention that you need to wear the new white slip I bought you. We don't want the men taking peeks through the embroidery of your dress to see your bra." Joan laughed a little. "When you're done dressing, I'll check your nails and your makeup. Wear the white pumps and I have a little flowery corsage that you need to put in your hair."

Gerald put on the panties and bra and then the breast forms Joan had bought for him. Then his pantyhose and then his slip. He then sat down on the bed waiting for Joan to get dressed, after which she would check his fingernail polish, his hair, and apply his makeup. Joan fetched a blue pantsuit out of her closet and put it on and then came over to Gerald to fix him up. When she was done she handed him his white dress and held it up for him to put on over his head. Joan then zipped him up. "You look pretty, Gerald. I'm pleased.”

“Why is it I have to wear the dress and you wear pants? That doesn’t seem fair to me.”

“Select a necklace or pendant and put that on," Joan said, ignoring his question. Gerald looked through the collection of necklaces and other pendants and selected a gold chain with a gold cross dangling from it. Gerald put on the white pumps and waited until Joan was ready.

Joan escorted him out to their car and opened the passenger side door for him. After he carefully sat down so as not to unnecessarily crease his skirt, she closed the door and got in on the driver’s side. She drove them the few miles to the Websters house. After she parked she went around to the passenger side, opened the door and helped Gerald out. They had been through this procedure a few times now, so that Gerald didn't give it a second thought. When she had him dressed up as a woman, Joan insisted on treating him like a woman and he had to just accept that fact.

When they were walking up to the front door, Gerald said, "Should I stay with the men or the women tonight?"

"Either one is okay. You're welcome to congregate with the ladies, or if you prefer you can try and hang with the men." As usual Joan made it difficult for Gerald. He was sure that whichever choice he made he'd end up making the wrong one. He braced himself for the inevitable surprise when the Websters and Masons saw him wearing a dress. This was a scene he had undergone a few other times already with other friends of theirs. It was three months earlier that Joan had first announced that she had bought a dress for him to wear for an upcoming visit to their friends Ted and Lisa. At that occasion it was just the four of them and Gerald had felt embarrassed and humiliated the entire evening as he tried to socialize wearing a dress. The four of them sitting at the dining room table. Three of them wearing dresses and made up as ladies and Ted the only clear male. When Ted opened the door when they had first arrived at the house, Ted laughed out loud upon seeing Gerald, but later apologized. When he was alone with Ted, Gerald hastened to say that Joan made him wear the dress. It wasn't his idea. Ted had looked at him puzzled wondering if he needed to say out loud the obvious - why did you do what Joan told you to do? Reading his mind, Gerald said, "Joan told me I have to wear this dress. She didn't ask me if I wanted to or not. She just told me I had to. So to not wear a dress I'd have to tell her that I'm not going to wear one, and I think she'd not be happy with me. She might even get mad at me." Ted shook his head and all he could say was "Whatever."

At this night's dinner party since there was to be five couples, if Gerald went with the men, there would be four of them and there was a good chance they would tease him in some way. On the other hand trying to keep up with the conversation of five women would not be easy and he didn’t know if they would resent him for being with them. He didn't know what to do. Joan rang the bell and Bruce Webster opened the door. He recoiled in surprise noticing Gerald. "Gerald? Wearing a dress and makeup? Holy cow!" He called into the house for Debbie, his wife, to come and she came quickly saying, "What is all the commotion? Oh, my goodness. Gerald is so pretty tonight. Look at the pretty dress he's wearing? What is going on Gerald?"

"Tell us," Bruce said.

"It's just that Joan told me I had to wear this dress tonight."

"She did, did she?" Bruce said,

"Yes," Joan said laughing. "Lately I've decided that Gerald should go out and about in pretty dresses. So, how nice of you two to throw a dinner party!"

Gerald followed Joan into the house and into the living room where the other guests were waiting. Glen and Pamela Mason, Mel and Carrie Ott, Mickey and Janet Mantle. "Holy smokes," Glen said upon seeing Gerald. "What is this? A dress? And all made up like one of the ladies?"

"It was Joan's idea," Bruce said. "Everybody, this is Joan and her husband Gerald. You are still her husband?"

There was silence as everyone waited for Gerald to say something. "Yes, of course, I'm Joan's husband. Like Bruce said, I'm wearing a dress because Joan told me to."

"Of course," Pamela said. "It's nice to see you both again."

Joan and Pamela exchanged air kisses and Pamela came up to Gerald and said, "I'm admiring your outfit."

"Joan picked it out."

"Pantyhose, pumps, a pretty dress. Can I be so bold as to ask what else Joan has been buying for you?"

"Yes, Joan bought me bras, panties, breast forms, a slip, a girdle and stockings."

"A girdle?"

"Yes, but tonight I'm wearing pantyhose. I think she wants me to wear the girdle on those days when she wants me to have a little curvier figure. I guess you'll have to ask her why. I don't really know. She doesn't explain herself very well."

"She doesn't?"

"No. Like tonight she told me to wear this dress and she handed me a bra, panties and pantyhose and told me to get dressed."

Pamela looked at Gerald trying to comprehend what he was saying. It was a bit bizarre to say the least. Finally, she turned and went to join the group of ladies that had formed in the kitchen. Gerald looked around and saw that the men had settled outside around a table. They were drinking cocktails. Since Pamela had walked away from him Gerald felt it would be awkward to follow her to the ladies. On the other hand the men looked formidable. Staying by himself would raise more notice of himself than anything, so he decided he had better meet with the men. Gerald walked over to their outdoors table and sat at an empty seat. Wearing high-heels, pantyhose and the dress contrasted so strongly with the casual shirts and slacks of the men that he felt as if he had neon flashing lights attracting attention to himself. If that wasn't bad enough he had lipstick and eye makeup and some blush on himself and his hair was styled long and over his ears like it is for women.

The men fell silent when Gerald joined them until Bruce said, "I was just telling Mickey and Mel that your outfit is new. Last time I saw you, you were dressed like any of us. What happened?"

"I told you, Joan just told me that I had to wear this dress.”

“So you do everything Joan tells you to do?”

“I don’t know. It’s just that she was very clear about it. She just said, ‘Here is the dress I want you to wear it tonight.’”

“What if she told you to jump off of a cliff? Would you do it?”

“She would never ask me to do that!”

“How do you know that? Isn’t telling you to wear a dress the same thing?”

Gerald found himself fighting back tears and Mickey said, “You’re being kind of hard on Gerald. You’re about to make him cry.”

“Sorry, Gerald,” Bruce said.

“How about we try and organize a foursome for next week?” Mel said, changing the subject.

Gerald was glad for the change of topic but then realized that the discussion of who could play did not seem to include him. He wanted to tell them that he’s available to play golf also, and he still dresses like a man for most everything except these few occasions when Joan tells him to wear a dress. But there was no easy way to communicate any of that.

After a while Gerald felt that the men were ignoring him and he got up and decided that he ought to try and see how he fit in with the ladies. They were still chatting in the kitchen and Gerald sauntered in trying to be inconspicuous. When Janet saw him she said, “You look good in that dress Gerald. Joan was telling us that when she saw it for sale she immediately knew it would be perfect for you.”

“Yeah, I guess Joan has a good eye for fashion.”

Pamela said to Joan, “Gerald was telling me before that besides pantyhose you sometimes dress him in a girdle and stockings?”

“True. Some of the dresses I’ve bought for him look a bit better when his waist is slimmer. So I bought a really pretty girdle for him and I’m now thinking of getting him a corset also. Slimming his waist is a pet project of mine. I want to see how much of a curvy figure I can coax out of him. If I’m lucky I’ll be able to try some other dress styles on him. I saw a darling swing dress with a fairly narrow waist, Gerald will look adorable in it.”

“I’m really curious as to what Gerald’s got going on underneath his dress,” Carrie said. “I assume he’s wearing a bra?”

“Sure, we’d be happy to show you.” Joan unzipped the back of Gerald’s dress and said, “I’m going to lift this up over your head, dear.”

“Right here?” Gerald said, but Joan persisted and took his dress off of him. Just when it was off and he was standing in the bright lights of the kitchen in his slip, Glen walked in to get a refill of his drink.

Gerald averted his eyes and stared at the ground as Joan pulled the top of his slip to the side so the ladies could see his bra. “I bought him a 38D Glamorise bra. This one is white, but I’ve also got him it in pink, beige and a taupe.”

“I like Glamorise bras, they’re comfortable,” Debbie said.

“Are they?” Glen said, laughing.

“Go on, Glen, this is ladies talk here. Scat,” Pamela said. Glen went back to the men, where Gerald could distinctly here him reporting to the others about the ladies inspecting Gerald’s bra.

“I got them for Gerald since besides being comfortable, I’ve always liked the lace on them,” Joan said.

“And he’s got breast forms in the cups?” Pamela said.

“Yes. I thought D cup is about right for Gerald.”

Joan lifted up Gerald’s slip to reveal his panties underneath his pantyhose. “See how I picked out some lacy panties that match Gerald’s bra. So far I’ve limited his panties to full coverage, but I am toying with getting him bikini style panties.”

“It looks like his legs have been shaved.”

“Yes, when I first decided to have him wear a dress, I realized that he had to do something about his leg hair. So he shaved it, and how often do you have to keep shaving it Gerald?”

“About once a month.”

“Yes, Gerald’s leg hair is pretty slow growing. Once a month he shaves his legs. I’ve sent him to the beauty parlor a couple of times now. You can see that his hair has grown out nicely.”

“I love Gerald’s pumps,” Janet said.

“Aren’t they cute?” Joan said. “I’ve always liked the fact that Gerald’s feet are fairly small, so it turned out to be easy to fit him for pumps.”

“He seems to have no trouble walking in them too,” Debbie said.

“Yes, we practiced our walking in heels quite a bit, didn’t we Gerald?”

“Yes, Joan.”

“Up and back in our living room, then up and down stairs. Then we took a walk through the neighborhood. Eventually Gerald got the hang of it.”

Gerald remembered that day well. It was a few days before their first dinner with Ted and Lisa. On a Saturday afternoon when it seemed like every neighbor in their subdivision was out mowing their lawn, or walking their dog, Joan took him out to practice his walking in heels. There had been a lot of staring at him all the while Joan was encouraging him to take nice smooth steps in his heels. “Be graceful,” she must have said fifty times. Ever since that Saturday Gerald has had the feeling that the neighbors see him differently. The women look at him with curiosity while the men smile.

Bruce had come over to get another drink for himself and he said to Debbie, “The guys are setting up a foursome for next Saturday. We have me, Glen and Mickey and we need one more.”

“I can play,” Gerald said, surprised that Bruce hadn’t directed the question to him.

“No,” Joan said. “I’m a better choice, don’t you think?”

Bruce looked between Gerald in his white dress and Joan in her pantsuit and said, “Yeah, Joan that would be great. You can join us.”

“Gerald, I’m sure the four spouses could include you in a ladies’ foursome,” Joan said.

Debbie said. “A great idea, Joan. Me, Pamela, Janet and Gerald. Men’s and ladies’ foursomes playing back to back.”

“Great, I’ll tell the guys,” Bruce said and left.

Gerald stared after him in a state of disbelief. How could he invite Joan to join the men in a foursome instead of him? Just because he was wearing a dress and Joan had on slacks? They had played many times in the past. “I can’t believe that you’re in the men’s foursome and I’m in the girl’s foursome,” Gerald said to Joan.

“It’s no problem, Gerald. I’ll get you a cute ladies golfing outfit for next weekend and you’ll fit in easily as the fourth girl.”

Gerald could see that the ladies were staring at him with looks that varied between sympathy and amusement. He knew that there was no arguing with Joan.

When they were sitting down to the dining room table, Gerald saw that Debbie had put place cards. Joan was sitting between Bruce and Glen and he was sitting between Debbie and Pamela near the opposite end of the table.

During the dinner Gerald glanced over at Joan and saw that she seemed to be having an uproarious time with Bruce and Glen. She was laughing gaily and seemed to enjoy the attention from the men on either side of her. If he didn’t know better, then he would think that she was flirting with them. Meanwhile, Debbie and Pamela engaged Gerald in a conversation about his hair, his makeup and his clothes. Debbie at one point said, “I like your hairstyle.”

“Thank you. It’s all Joan’s doing. She told the hairdresser what she was looking for and the woman did it.”

“Well it came out very nicely,” Pamela said. “Joan was telling us that she’s planning on getting your ears pierced. She’s already picked out some nice earrings for you.”

“She hasn’t mentioned that to me.” Gerald looked down the table at Joan who happened to be laughing so hard she had rested her hand on Bruce’s shoulder. He would have to ask Joan about that on the way home.

After dinner everyone got up to retire to the living room. Joan said in a voice that Gerald was sure everyone could hear, “Come with me to the bathroom, I’ll fix you up.”

“Fix me up?” Gerald said under his breath.

“You know, your makeup. I’ll help you freshen your face. Come with me.”

Gerald followed Joan to the bathroom where she took makeup out of her purse. “Someday you’ll learn how to do this yourself.”

“I don’t see why you have to mention this in front of everyone. Tell me to join you in the bathroom to fix my make up?”

“Purse your lips and I’ll start with the lipstick.”

“Did you hear what I was saying?”

“Now a little powder and then touch up your eyes. Yes, Gerald, I’ve heard you. It’s definitely true that earrings are the one thing that’s missing.”

“I have to pee,” Gerald said.

“Go ahead, but be careful with your pantyhose.”

“OK, sure.”

Gerald was about to sit when Joan said, “Remember to keep your legs together, especially your knees when you’re sitting and when you’re seated.

“I’ve been careful all night, I’m pretty sure I have.” This was something that Joan had stressed over and over again the first time she had him put on a dress. “Keep your legs together when you sit, Gerald. You don’t want to give a free display to the nearby men. Their eyes are always looking for an opportunity to see our panties.” He had wanted to remind her that he was not actually a woman, so her use of the expression “our panties” was just plain wrong. But it was too complicated to explain to her and he had let it slide. What was he going to do? Get Joan annoyed?

When Joan and Gerald left the bathroom, they passed Carrie going to it and she said to Gerald, “All freshened up, are you? You look good.”

“Thank you Carrie,” Gerald said.

Gerald and Joan sat together on the sofa in the living room. On the other side of Joan from Gerald, Bruce sat down and next to him was Debbie. Gerald had the distinct impression that Bruce was sitting a tad too close to Joan. This was something else he’d have to bring up with Joan on the way home. Debbie and Bruce organized some games that pitted couples against couples. They had served a digestif so the couples were well mellowed. Joan put her arm across the back of Gerald and held him affectionately, which had the effect of making him doubt that she was actually flirting with the other men. It was a nice gesture on her part, but he could also see that for the other couples, Mickey had his arm on Janet’s back and the same for Glen and Pamela. Once again, Joan had managed to place him in the woman’s role. He could also see that unlike the other men in the room, he had to sit with his legs together in his pantyhose. It would be a major breach of etiquette if he sat like a man and he’d immediately get scolded by Joan.

As they drove home that night, Gerald said, “When were you going to tell me that I have to get my ears pierced?”

“I’m so sorry. I forgot to tell you. Tomorrow I’m taking you to the mall and we’ll get it done. Initially you’ll be wearing gold studs and then we can dress you in lots of pretty earrings.”

“I’ll have to show up at work with gold studs in my ears.”

“Lots of men have pierced ears nowadays.”

“Yeah, not men who wear a blue business suit to work at a desk!”

“No one will notice, or care if you do. They’ll just think that you’re a lot more interesting man than they ever pegged you as being.”

When Gerald and Joan arrived home, Joan grabbed Gerald and gave him a deep tongue kiss. Then she started taking his dress off of him over his head. When it was off she pushed him onto the bed and she took off her slacks, her blouse and then her bra and panties so she was naked. She got on top of Gerald, pulled down his pantyhose and grabbed his penis taking it out of his panties and she rubbed it until it was hard, which did not take much effort, and then she impaled herself on his shaft and vigorously pumped her hips up and down and felt up Gerald’s breasts through his bra. In a matter of minutes, before Gerald had gotten close to orgasming, Joan let out a wail of pleasure, said “Oh God, Oh God, Oh God,” her body shook and she came. She extracted herself from Gerald’s still raging boner, and said, “That was great my love,” and a minute later was sound asleep.

“Just great,” Gerald said to himself. Joan’s become so selfish. He went into the bathroom and gave himself the orgasm that Joan should have given him and then got undressed and went to bed.

***

The next Saturday Gerald accompanied Joan to the golf course. She had bought him a short pink skirt and a pink top and pink golf shoes and socks. Also, she had taken him to the mall the day after the dinner party in order to get his ears pierced so now he was wearing gold studs in his ear lobes. “Aren’t you cute,” Debbie greeted him when Gerald joined the rest of his foursome. “I love the cute outfit Joan found for you. A little skirt and pink shoes.”

Joan’s foursome joined them and Gerald was pretty sure they exchanged some jokes among themselves concerning how pink Gerald was. With the girls teeing off ahead of the men, Gerald and the women assembled in the tee ground a dozen yards ahead of the men. One by one they teed off. Janet hit a great shot which Gerald knew immediately that he’d have a hard time beating. Both Pamela and Debbie hit respectable shots. Now it was his turn. Of course he had never played golf wearing a skirt before and with his large D cup breast forms in his bra. Holding his driver he faced his ball. He realized that he could feel his breasts touching the inside upper parts of his arms. He took a practice swing and he became aware of how his breasts bumped against his arms. He should have watched the women tee off because he would have seen how they cope with the presence of breasts. Obviously, it didn’t bother them, so maybe he was doing something wrong. Was he supposed to find a position where his breasts did not touch his arms? Self-conscious because the men and ladies were all looking at him, he swung at the ball and just managed to knock it one foot off the tee. He put it back up on the tee and this time hit the ball so that it bounded along the ground out onto the fairway well behind the other women.

When Gerald finally got the ball to the green he three-putted and had an eight for the hole, while Pamela and Debbie had sixes and Janet had a five. While they were walking to the next hole, Gerald said to the ladies, “Is there a trick in swinging the club having breasts?”

The three women laughed and Debbie said, “Welcome to the club, Gerald. All women with large breasts have to learn how to deal with their breasts getting in the way of their swing.”

“What’s the trick?”

“Basically, avoid crushing your left breast with your left arm, but do get your right arm to swing forcefully against, over or past your right breast.”

“Thank you, I’ll try and do that.”

Debbie’s advice helped to some extent, but by the end of the eighteen holes, Gerald’s score was much higher than that of the three ladies. Each of the men and Joan had done better than Gerald’s foursome so he was in last place all by himself.

“What happened to you Gerald? The ladies beat you handily,” Glen said.

Gerald made a face and Joan said, “You see Gerald. That’s why I was invited to play in the men’s foursome.”

“My breasts interfered with my swing,” Gerald said, causing everyone to laugh.

“Maybe you should adjust your boob size for golf days,” Bruce said to Gerald, sounding as if he was sincerely being helpful.

“You’ll have to ask Joan about that. She’s the one who decides on my boob size.”

“There are lots of big busted women golfers including myself and the other ladies here,” Joan said. “We figured it out and eventually Gerald will. I’ve got videos he can watch.”

The four couples stayed to have a beer at the club house. While they were sitting there, the female golf pro, Ellen, not even thirty years old and very beautiful walked past and Joan, who had taken lessons with her a year earlier, said hello to her. Ellen stopped to chat and Debbie said, “Perhaps Ellen could help Gerald with his problem.”

Ellen noticed Gerald and said with a surprised tone, “You’re dressed like a woman. Playing golf like you’re one of the ladies?”

“It’s Joan’s idea.”

“Joan?”

“Yes, I like Gerald in pretty clothes and I thought it would be nice to have him playing golf in a cute pink skirt and top.”

Ellen laughed and said, “Okay, Joan.” To Gerald she said, “So what problem are you having?”

All eyes were on Gerald. He glanced at the men and then at the ladies. “Shouldn’t I get help from Jimmy?” Jimmy was the male pro.

“What problem are you having?”

“When I swing my club my breasts are getting in the way.”

Ellen laughed. “I guarantee you that Jimmy couldn’t help you with that. But I suppose I can.” Ellen stuck out her formidable chest that was every bit as big as Gerald’s. “You shouldn’t feel bad because this is a common problem with large chested women. I can give you a lesson on how to get around that. I’m sure it will really help your game.”

“Joan says she has a video that could help me.”

“There’s nothing as good as a personal lesson, Gerald. Let Ellen show you what you need to do,” Joan said.

“Fine,” Gerald said.

“Meet me in the pro-shop in half an hour. Is that good for you?”

Gerald looked at Joan and he said, “You’ll wait for me?”

“No need. There’s room for Joan in our car. We’ll take her home,” Bruce said.

***

Gerald met up with Ellen and she took him into her office and closed the door. Being alone in a room with this young very attractive woman made Gerald nervous. “As you’ve seen, I’m like you Gerald, I’ve got a large chest.” Gerald had been marveling at the way that her tight white golf shirt revealed her significant bosom. “But my breasts do not affect my ability to hit a golf ball.”

“I didn’t even know I had a problem until the first tee when I flubbed my shot.”

“Before I discuss what to do, I want to make sure that this is what you want. Forgive me for sounding like a social worker, but I’m curious to find out if you actually like dressing like a woman and having large breasts? You’re not being coerced by Joan, are you?”

“It’s sort of a coercion, I guess. I mean she tells me to wear a skirt, so I have to wear a skirt.”

“Why don’t you tell Joan that you’re not going to wear a skirt?”

“Everybody seems to say that to me. But Joan doesn’t say, please wear a skirt, or I would like you to wear a skirt. She just says, you will wear this skirt. I want you to be pretty when we go out. She doesn’t leave me any choice.”

Ellen stared at Gerald trying to see the logic of what he was saying. Then she said, “You could still refuse, couldn’t you?”

“I think it would make Joan very mad at me.”

“Perhaps.”

“I don’t feel right making her angry. In fact I hate to think about that.”

Ellen was having a hard time understanding Gerald. Perhaps when Joan got mad she threatened Gerald with a revolver, but she didn’t think that Joan was capable of that, or that she would even get mad. Ultimately every married couple has to figure out marriage for themselves. Who was she to say anything? She’d been married and divorced already and she was not even thirty years old. “Yes, you’re probably smart not to get Joan angry. She’s quite an amazing woman.”

“Yes, and she seems to always know what she wants.”

“Anyway, getting down to business, so you’re wearing a bra underneath your top?”

“Yes.”

“Let me take a look. I want to see what kind of boobs you have. Raise your blouse up.”

Gerald lifted up his blouse over his bra.

“That’s a pretty bra and I see that you have what, D cup breasts?”

“Yes, they’re D cup. Joan bought me the bra. She likes me to wear fancy bras and she decided that I should be D cup.”

“That’s okay, Gerald. You can pull your top down now. So there’s no reason why you can’t learn to swing a club the way busty women do. I’ll show you.”

Ellen took Gerald outside to a practice area and explained to him how he was to swing the club despite having boobs. She must have demonstrated the proper technique twenty times and each time Gerald was mesmerized watching her arms swing past her chest. When it was his turn to swing the club, he saw that four men from a foursome had gathered to watch the lesson. He felt self-conscious enough wearing the pink skirt and top without also having men watch his golf swing. The end result was that he was so nervous that Ellen had to physically take his arms from behind him and guide them along. Having this very attractive women clutching him tightly made it even more difficult for him to concentrate. Even with this help Gerald was klutzy and kept having his arms bang into his breasts disturbing his swing. When the men finally moved away chuckling among themselves, Gerald was at long last able to concentrate well enough to make some improvement in his swing. “I think we made some progress, Gerald,” Ellen said, grasping at any tiny positive outcome.

When Gerald got home he told Joan that the lesson had helped him a little with his swing. “It’s not easy being a man dressed like a girl at the golf course. Everyone is looking at me. I feel so vulnerable.”

“I hope you play better next time. I’ll bet it’s not much fun for the girls to play with someone who isn’t at their level.”

“Sorry, Joan. I’m working on it. Having breasts is making me have to completely revise my golf swing. That’s not easy.”

***

Gerald's parents’ anniversary was coming up soon and by tradition he, Joan and his parents would go to a fancy restaurant for dinner. While Gerald had made peace with Joan’s insistence that he wear a dress to dinner parties with their friends, he was becoming increasingly worried about what she would do for his parent's anniversary dinner. Would she let him wear his blue suit or was she going to put him in a dress to meet his mom and dad? The thought of them seeing him all decked out as a woman was utterly and totally frightening and he prayed that Joan would never force such a thing on him.

Each week closer to the anniversary Gerald got more nervous that Joan would suddenly announce that she had bought a dress for him for the occasion. It was going to be at a fancy restaurant and Gerald knew that the dresses she had gotten for him thus far would not be appropriate. With just one week to go, Gerald was starting to think that Joan would not be getting him a new dress, when he saw that Joan had come back from work holding a garment bag. He braced himself for her typical announcement, “I’ve bought a pretty dress for you to wear to …” but instead she said, “I’ve gotten myself a new suit for the dinner. Your mother will especially love it.” She proceeded to take it out of the bag. It had dark blue slacks and an elegant jacket with lapels that were styled like a man’s sports coat. Absolutely giddy with happiness that he obviously wasn’t going to have to wear a dress, Gerald said, “I’m glad I’ll be able to wear my blue suit to the dinner.”

“Oh, no, Gerald,” Joan said. “Your dress will be ready for me to pick up tomorrow.”

“Really, Joan? My mom and dad seeing me in a dress? Do you have any idea how embarrassing that will be? And it will hurt my parents to see their son in a dress in public like that!”

“Are you done?” Joan asked. Gerald nodded his head and she continued, “Of course you’ll need some new heels and a matching bag which I’ll also have to buy. You’ll also need something to take an inch or two off of your waist so as to get a nice line in the dress. I’ve got a pretty good idea which shaper to get you.”

***

The next day Gerald dreaded seeing what ridiculous outfit Joan had gotten for him and his worst fears were realized. She had bought him a sophisticated, pink, feminine evening dress with a puffed-out skirt reaching to just above his knees. He could see that there were several layers of tulle petticoat sewn into the pleated skirt that kept it full. The bodice was form fitting and would make his boobs look immense. Around the sweetheart neckline was a touch of lace details. She had also gotten matching pink pumps, a small pink evening bag, and a shaper that Gerald couldn’t identify.

“How will I ever be able to face my parents dressed in this?”

This wasn’t a question that Joan cared to answer. “I’m really looking forward to the dinner. I enjoy your parents. They're fun people.”

***

The evening of the dinner, after Gerald was all cleaned up, Joan handed him white lacy panties and a white bra to wear and the new shaper which she said was a white demi-corset. “Put on your bra and panty and then I’ll help you with the corset.”

Once Gerald had the bra and panty on, and his breast forms inserted, Joan had him step into the demi-corset and pull it up over his hips. Three garters on each side dangled down toward his thighs. “Now clip the fasteners,” she said, and he proceeded to one by one pull the open ends of the demi-corset together and attach the hook and eyes. The further up his waist he went the harder it became and he felt his midsection being condensed and reshaped by the demi-corset. The top of the demi-corset was a few inches below the bottom of his bra. “How is it, Gerald? Comfortable?”

In a weird way it wasn’t a hardship to wear the demi-corset. It was firm and assertive, but his body seemed amenable to assuming the shape it wanted. It even felt a bit pleasurable in an odd way, like he was now straightened out or put together in some better way. “Yeah, I guess it’s comfortable. It sort of gives me a comfortable feeling.”

“Well I am so pleased. The demi-corset is exactly what we need to get you a girl’s waist. See how your hips are now wider than your waist? You’ve been rearranged to have a girl’s profile which is really essential for looking good in the pretty dress I got you. Of course, I don’t recommend you eat a big dinner. Corsets and full stomachs are sort of a contradiction. You’ll have to eat like a bird and drink in moderation.”

Drinking in moderation was the last thing Gerald was intending to do. Thinking about drinks it occurred to Gerald to ask, “How do I pee if I have to?”

“The easy thing is you pull aside your panties when you sit on the toilet. No need to take off the demi-corset. Of course, you must use the ladies room. The men would be alarmed by ladies entering their bathroom. Now, you need to put on your stockings.”

Joan handed Gerald a package of brand-new stockings. He had already enough practice with pantyhose that he understood how to put them on. He also figured out how to attach them to the garters dangling from the demi-corset. When he was done with this phase of dressing, Joan put make up on him since she didn’t yet trust him with that, and made sure his hair was groomed. She had him take out the gold studs from his earlobes and gave him some delicate dangly earrings with a little pink jewel in them to put on. The final step was to lower his dress over his head and zip up the back and then step into his pumps. Joan led him to the mirror and said, “I love how pretty you are, Gerald. Doesn’t it feel good to be such a pretty woman?”

“Joan, you know I should be wearing my suit to dinner. I mean it doesn’t matter if I look pretty or not. I’m wearing a dress and I should be wearing my suit. My parents are going to be really freaked to see me like this.”

“When a woman has her favorite underwear on and nice new hose, a pretty dress, and her nails and face all made up perfectly, it’s such a nice feeling. This is going to be such a fun occasion for the two of us!”

Gerald wanted to tell Joan that the key word was “woman” but since he wasn’t a woman, why should he feel so great having on a great bra and corset and stockings and a dress? Why should he? Except there was a little bit of truth to what Joan was saying. He did feel that being dressed so nicely gave him some sort of special power that would get him through the evening.

When Joan was dressed too and they were walking to the car, Gerald couldn’t help but wonder why he had to be the one all puffed up in the pretty pink dress, while Joan was wearing her dark blue pant suit. “You know, Joan, you’re always telling me that you like me to be pretty, so you have me wear a dress. Okay. But why do I have to have to be dressed prettier than you? Why do I have the dress and you don’t? That doesn’t seem right does it?”

In typical fashion, Joan ignored his remark and opened the passenger door for him. He sat down and she closed it and she got around to the driver’s seat and started up the car. Gerald looked at Joan while she was concentrating on backing down the driveway. He couldn't remember ever feeling as helpless as he did at that moment. Dressed in every detail as a woman and being driven to see his parents. He was utterly trapped. He imagined that if he tried to run from the restaurant in his heels, not that he ever would have the courage to do such a thing, Joan would easily overtake him and lead him back to the restaurant.

Every mile closer to the restaurant, Gerald felt more upset. It was like he was marching to the edge of a cliff where he’d fall into the void. When Joan pulled the car up to the restaurant and parked, they walked to the entrance and entered. Across the room they could see Gerald’s parents sitting at a table. “Good, they’re here,” Joan said pleasantly and waved at them. Gerald was overcome with panic and would have bolted except Joan firmly grasped his hand and led him to the table.

Gerald watched in fear as the faces on his parents went from smiles to questioning to abject horror. He didn’t know which of their faces he should look at, they seemed equally frightening to him. Before they could say anything, Joan said, “We’re so happy to be here for your anniversary! We love celebrating it with you.” She held out the chair for Gerald and he sat down next to his mother and across from his father. Then Joan took the last seat.

Gerald said, “Hi mom and dad.”

“What’s going on here?” Gerald’s dad said to Gerald in an excited voice. “You’ve become a transvestite and you’re acting like the woman?”

“Oh, my God, Gerald. How long have you been cross dressing?” his mom said. “Poor Joan.”

“And you’re making Joan go out with you in public like this?” his dad said

“I’m not a transvestite, mom and dad. I don’t want to be dressed like a woman. It’s all Joan’s idea. Not mine!”

“What in the world Gerald? How could it be Joan’s idea?”

“Just ask her!”

“What’s he talking about?”

“I decided that I like Gerald to wear pretty dresses when I go out with him. Having him dressed like a woman and with a woman’s grooming and accessories is nice. I’m especially happy with the way I’ve been able to give him some nice curves so his dresses look even better. That took a bit of experimentation with shapers but I think I’ve succeeded.”

“How could you let Joan do this to you? I’m aghast,” Gerald’s father said.

“I don’t know what I can do, dad. Joan told me I have to wear a dress. She didn’t say maybe and she’s not willing to even talk about it.”

“Can’t you just refuse? Am I missing something here? You can just say no, can’t you?”

“I don’t want to think about what would happen if I said no. It’s a lot easier to wear pretty dresses and be pretty than to have Joan be cross with me. I’m not saying it’s easy to wear dresses with my friends and now with my family, just that it’s easier than the alternative.”

“Jesus Christ, son, grow some testicles! Unless Joan is going to shoot you, why in the world would you be afraid to just say no?”

Gerald closed his eyes and felt himself getting choked up like he might cry. He wished his dad could see why he could not refuse when Joan told him to wear a dress. Gerald snuck a peak at Joan to see if maybe she would bail him out in some way. Is there something that she could say to his dad?

“I think I’m in the mood for salmon tonight,” Joan said pleasantly. “I look forward to this meal every year. You are my favorite in-laws,” and she laughed.

While Gerald’s dad sat in his seat as if he had been frozen into a block of ice, Gerald’s mom said to Gerald, “You know Gerald, I’ve been wearing dresses my whole life and tonight you’re wearing a dress. You’re also wearing makeup and lipstick like I do, and we both have girls hairdos. I see your wearing earrings like I do. Your heels are like mine also. And tell me what you have got on underneath that dress?”

“Mom?” Gerald said.

“Tell me, Gerald. Are you wearing a bra like I do?”

“Yes, mom.”

“And panties like I wear?”

“Yes, mom.”

“I think you’re also wearing a girdle like I do. Am I right?”

“No, it’s a demi-corset that Joan bought me.”

“I’ve got one of those too, Gerald. I use it to narrow my waist a little.”

“That’s why Gerald is wearing his,” Joan said. “The dress he’s wearing looks so much better if he has a narrow waist. I’m very happy that I could find a shaper that accomplishes that.”

Gerald’s mom continued talking to Gerald, “Your demi-corset has garters that hold up your stockings?”

“Yes, mom.”

“When I wear a girdle or a corset or a garter belt I have garters that hold up my stockings.”

“Yes, mom.”

“Look at me, Gerald,” his mom said.

Gerald forced himself to look into his mother’s eyes. She said, “I wear bras, panties, demi-corsets, stockings, dresses, high heels, makeup and earrings because I’m a woman, Gerald. Your mom is a woman.”

“Yes, mom, I know that.”

“You’re a man, Gerald, unlike your mom who’s a woman, yet you’re also wearing a bra, panty, demi-corset, stockings, a dress, high heels, makeup and earrings just like women like your mom wear. Why?”

“Because Joan says I have to.”

“Are you a woman?”

“No, mom.”

“Do you have breasts and a vagina like your mom does because she’s a woman?”

Gerald began crying and could not answer his mom’s question. A waiter came over and said, “Shall I come back later?”

Joan said brightly, “Yes, I think we need more time. But we could order some drinks now. I’ll have a dry martini and Gerald here will have a daiquiri.”

The waiter queried Gerald’s parents for drinks and his father wanted a double Scotch straight up and his mother wanted a martini.

The only sound at the table was Gerald sniffling. “Gerald, I’m going to have to take you to the ladies room and fix you up,” Joan said.

“Sorry, Joan,” Gerald said.

Joan got up and so did Gerald. Gerald’s mom said she was going also and the three of them went to the ladies restroom.

Inside the restroom, Gerald’s mom said to Gerald, “Your breasts are as large as mine. What size bra are you wearing?”

“D cup, mom. Joan bought me D cup bras and breast forms.”

“She did, did she?”

“Yes, mom.”

“When he’s all dressed up and pretty,” Joan said, “Gerald behaves like a lady. He knows how to pee like a lady. You’ve already seen that he walks in heels like a lady and sits like a lady. He’s very careful to keep his legs closed.”

Joan took a stall and indicated for Gerald to take one and so did Gerald’s mom. Gerald could hear the rustle of Joan’s pants and his mom’s skirt being raised and his mom’s girdle and panties and Joan’s panties being pulled down and he did the same for himself. Then he could hear Joan peeing and then his mom and then finally himself. As he sat there he once again felt trapped and helpless. He and his mom were peeing in a ladies restroom together as if he were her daughter and not her son. She had made it abundantly clear to him that he was now no different than his mother. He was a girl as far as she was concerned. He heard the tissue paper rolls move to either side of him and then he used a couple of squares to dab at his own pee hole. Then Joan flushed and his mom flushed and then he flushed. Joan opened her stall, then his mom did and then he did. They each walked to a sink and washed their hands. After they dried them, Joan touched up her own make up and then did Gerald’s, while his mom worked on herself. The three of them then exited together and joined up with Gerald’s dad. He had downed his Scotch and ordered another. Evidently, he had found a way to deal with his ball-less son.

For the rest of the meal Gerald’s dad tuned out everyone and concentrated on the steak he had ordered. Gerald ordered salmon also, after first making sure that Joan approved. Gerald’s mother was eating a crab cake. “You’ve got Gerald on a very short leash,” Gerald’s mom said to Joan.

“I do enjoy Gerald being pretty, as I’ve said. He struggles with some aspects of his grooming, for instance, he hasn’t gotten a good understanding of makeup just yet, though we’re working on it. But you should see him put on his pantyhose, just like you or me. It’s quite endearing to watch. His legs are shaved and very cute.”

“OK, Joan,” Gerald’s mom said, “could you tell me what the long term is going to look like here?”

“To tell you the truth, I’ve enjoyed Gerald being pretty so much, that I have been thinking that he should wear a dress every day. Why just when we go out? I’d enjoy seeing him around the house being pretty.”

“But you wouldn’t stop me from wearing my suit to work, would you?” Gerald said.

“I don’t see you at work, Gerald, so it’s irrelevant how you dress there as far as I’m concerned. However, you might find it easier in the long run to dress like a woman all the time. That will allow you to put your full attention to developing the habits and instincts of a pretty woman.”

“I never thought of Gerald as anything other than a man,” Gerald’s mom said, “but now I have to wonder if that’s true. Just in the course of this dinner I’ve seen Gerald behave like he’s a woman, the kind of woman who can’t help but take a feminine role. He fills out that dress so nicely that I can imagine that he’s got a girl’s body with a vagina and breasts.”

“But mom!” Gerald said.

“Don’t ’but mom me.’ If you were a man you’d stand up to Joan instead of cowering. As far as I’m concerned you’re not a man, Gerald. Instead, you’re a caricature of a woman.”

With that, Joan said, “My dinner was delicious and I hope we repeat this next year. It’s been so much fun.” Joan picked up the tab and the dinner was over.

***

A few days after the dinner with his parents, Joan said, “From now on, I want you to dress pretty all the time you’re with me. When I’m not around, you can dress any way you want, though if you want men’s clothing you’ll have to get that yourself. I will only be buying you woman’s outfits from now on.” True to her word, Gerald now had to dress as a woman whenever he was with Joan. It meant that at night he had to wear a nightie. All weekend long he had to dress in various skirts and dresses that she arranged for him. As time went on he became adept at choosing his own outfits and in grooming and accessorizing himself. Gerald still managed to go to work as a man though he felt this was getting harder and harder to do. For example, as soon as he came home from work on a Friday, Joan made him apply fingernail polish that he’d have to take off on Monday mornings. It wasn’t easy to get every trace of polish off. Sometimes he’d be pulling into his parking space at work realizing that he was still wearing his earrings. One day he knew that someone would see his pierced ears and say something.

Gerald’s parents and friends were largely reconciled to the new Gerald. His parents could not condone it but they could see that Joan had much more sway over their son than they did and it was pointless to make a continuous stink about what she had done to him. From Gerald’s point of view he was feeling lonely because he knew that he didn’t fit in well with the men in their social circle anymore, and yet he also found it hard to make connections with the women. He felt the women treated him like he was the result of Joan’s experiment in husband domination, not an actual woman like one of them. It was particularly frustrating because he was dressed as nicely as they were.

Usually Joan ignored Gerald’s complaints but for some reason, his admitting that he was lonely struck a chord with her. She agreed that it was a legitimate observation. “The problem is clearly that you’re not being enough of a girl, Gerald. Women can see that you’ve made a great attempt to emulate women, but they’re not sensing that you feel and behave like a girl. Until you do, you’re going to be betwixt and between.”

“What can I do?”

“Behave like a girl and the girls will accept you as one of their own.”

“I don’t know how to behave like a girl.”

“I think you do, but you just need more practice at perfecting it. For example, one thing you could do is take an interest in the kinds of things that girls take an interest in.”

“Like?”

“Well, you could start with your clothes. Go shopping. Buy yourself a bra that you find is pretty, or a panty or a dress. Immerse yourself in stores that sell women’s clothing. The same with jewelry. Shop for earrings that you like. Women love shoes so shop for some heels that you find attractive. Schedule your own visits to the beauty parlor and get your nails done. Go to a spa and take care of your body. Women are usually pretty good with cooking, baking and sewing. They often have an interest in gardening and flowers. Like what I like. I’m a woman. Like what Debbie and Pamela like, they’re women.”

Gerald thought about what Joan had said. He was only lonely because he dressed like a woman and he dressed like a woman because Joan told him to, and Joan told him to because he was unable to say no to her. To not be lonely, he either had to say no to her, which was impossible, or he would have to learn how to exactly imitate the behavior of women. “Okay, Joan. I’m going to try that. I’m going to see if I can be enough of a woman so that our lady friends accept me as one of their own. Is that okay?”

“Yes, Gerald.”

“Then I’m going to go bra shopping by myself. You bought me all my bras so now I need to see if I can find a bra that I can call my own. That way I’ll have something I can share with the women.”

The next Saturday morning Gerald put on a skirt and blouse and decided that he’d go shopping for bras as if he was a woman. He’d try to be a woman with the women he met and even with the men, if he met any. It was a tall order, but he had to see if he could ever begin to feel like he was a real woman.

Buying a bra at the lingerie department of a local department store would be a big step, but he would do everything he could to succeed. Driving to the mall he thought about the Glamorise bras that he had been wearing thus far. Did he like them or did he not? Did he have any feelings about them? They were the only bras that he had yet worn, but they were bras that Joan liked. So that’s exactly what Joan was talking about. Since she was a woman, she knew which bras she wanted Gerald to wear. She had a definite opinion. This was key for him. He would have to get a desire for a particular style bra that he could tell the other ladies, “I prefer so and so bra because … it’s pretty? It’s comfortable? It’s made nicely? I look good in it?” Yes, he would have to have a reason why he liked the bra. Hopefully, when he was examining the bras, he would see a bra that would become his favorite for some reason or other.

When he got to the department store, it was Gerald’s first time out and about wearing a skirt without Joan accompanying him. He was so practiced walking in heels and used to wearing a skirt or dress and, in this case, pantyhose that he did not pay much attention to what other people might think seeing him. With his hair and makeup and shapely figure, he imagined that he might be thought of as being a woman or else, with some people, he might be thought of as being both a man and a woman. Gerald approached the lingerie section of the store and decided that he was as much a woman as any of the others looking through the panties and bras and he walked over to the bra section and began concentrating on the bras in front of him. It was amazing how many different kind of bras there were. So many styles and colors, but he was going to focus on identifying a bra that he could honestly tell himself that he liked.

He began systematically staring at bras, taking them one by one off of the racks, holding them up and looking at them carefully. Did the bra speak to him, he wondered? What was he feeling looking at the bra? He must have gone through a dozen bras this way, thinking that he could rank them from 1 to 12 as far as being his favorite. The ranking seemed to be based on how sexy he thought the bra was. Sexy seemed to mean to him that it had a kind of delicate structure and rounded cups that were almost begging for breasts to slip into them. Yes, that was it, bra cups that were inviting. That were sending out a message to Gerald, “We want to hold your breasts.” And then his response, “Yes I want you to be holding my breasts.”

It was an interesting experience. As he branched out to more and more bras he felt he was getting better and better at seeing clearly if the bra spoke to him this way or not. While he was so absorbed, a middle-aged saleslady came over to him and said, “Can I help you with anything?”

Her question broke Gerald’s concentration and he looked at her name tag and saw that it said, “Linda.” “Well maybe. I’m trying to decide which bra is my favorite. So far, I think I can sort of see which bras I like as against the ones I’m not too crazy about, but I’m worried that maybe I ought to take into account more than just what the bra looks like.”

“Well, sure, I suppose.”

“I mean that up to now my wife has bought my bras for me. But now I want to buy them myself, but I want to think about buying my bras the same way a woman does.”

The saleswoman looked at Gerald like men with a straight jacket would soon be coming by to grab him. Finally she said, “You’re serious?”

“I’m sorry, but it’s a long story why I’m dressed like a woman. Let’s just say that my wife likes me to be pretty. She prefers me this way.”

“Okay, okay. I don’t mean to make you defensive. Women buy bras thinking of many things besides whether or not they like the way the bra looks. Women also want their bras to be appropriate for their body because that can mean a lot as far as comfort goes.”

“I see,” Gerald said.

“May I ask what bra brand you’re wearing now?”

“It’s a Glamorise 38D.”

“An interesting choice. Well I should say that as far as myself, I pick my bras as a result of some experimentation I did when I first started wearing bras. At that time I found out that the bras from certain brands just tended to fit me better than those of other brands. So then I stuck to those brands. Of course, every so often I see a bra that is so pretty that I can’t resist buying it. Often these are the kind of bras that girls let their boyfriends see.

“So I need to try some different brands?”

“Yes. Find some bras you find that are pretty and then go in the fitting room and see which ones actually fit you best. One important issue, besides the size of your breasts, is their spacing. You’d be amazed at the variation in the distance between the breasts of women. For some women, their breasts practically touch, while for others there is a wide gap. Also some breasts tend to project straight forward while others project outwards at an angle. There are bras that are more or less appropriate for each of these kinds of breasts. In your case can I assume that you’re wearing breast forms?”

“Yes.”

“So for you, your breast forms will go wherever the bra tells them to go. You can have breasts closer together or further apart so that‘s something to consider. You can have them project high or low, as well. What kind of look do you want to have? Right now, your Glamorise bra is giving a fairly normal projection of your breasts, but other bras might change this. You could get a bra that moves your breasts up slightly that would enhance how busty you look in a tight blouse. Or you could have your breasts sag more than they do now. Find some bras you like, take them to the fitting room and put them on and then go from there. You can try five at a time.”

“Thank you, I’ll do that.”

“Would you like my help in the dressing room? I could help you with deciding if the fit is correct for you.”

“That would be great.”

“Go find some bras you like because they’re pretty and then I’ll join you in the fitting room.”

Gerald continued his search through the bras. He was starting to see which bras he immediately liked and then among those, he sensed that for some of them he had a desire to see how he looked in them. In truth it was even more than that. It was a desire to use the bra as a way of showing the world that he was pretty. The bra would be an extension of himself that underlined his own beauty. Having a nice curvy figure and wearing bras of pretty colors and lace would allow him to fulfill some inner need to be sexy and pretty. Now that his purpose was getting clearer, Gerald decided on five particular bras that he found intriguing, and wondered how he might look in them. He walked to the fitting room and the saleslady accompanied him.

“What a pretty selection of bras, you found,” Linda said. “I can already see something of what your taste is and what sort of bras you think you’re going to be comfortable with.”

Gerald went into a cubicle and Linda joined him. Gerald began unbuttoning his blouse and when it opened up enough for Linda to see his bra she said, “So your wife picked out the Elegance Lacy Underwire bra for you. A nice, pretty bra. Are you happy with it?”

“Yes, I guess so.”

“I can see that the bras you selected today are sleeker and more delicate, though pretty in the same way. You’ve definitely got the same impulse toward bras that I’ve seen in many of my women customers. You’re in good company as far as that goes.”

“Well I sort of had a feeling that my body wanted to be wearing these bras. Does that seem normal to you?”

“Why of course it does. A girl might look at a particular bra and just be really curious as to how she would look in it. If she likes what she sees and it’s comfortable then it becomes part of her bra collection.”

For the first time since he had set out on this bra buying excursion Gerald felt that it might actually be successful. He would zero in on a bra that he really did like, that made him feel good wearing it and then he’d have something he could share with the other ladies. He imagined himself in the kitchen with the other women and he’d say “I bought myself a new bra” and one of the other ladies, maybe Debbie would say, “What bra did you buy?” and then he’d tell her and then he’d talk about why he liked the bra. Then maybe one of the women would talk about a bra she had bought, or perhaps some shoes or a dress and he’d be part of the discussion. For the very first time he’d begin to feel like one of the girls, and then finally he would no longer feel so lonely all the time. Gerald stirred out of his fantasy and said, “I think these five bras are my favorites.”

“So take off your blouse and your bra and try them on.”

Gerald took off his blouse and then took his breast forms out of his bra and put them on the bench. Then he undid his Glamorise bra and put on the first of the bras he had found, a Wacoal Embrace Lace bra. All five bras were 38D. The first was the most expensive and a beautiful ivory color with rich lace details on it. He put it on and asked, “I should put my boobs back in?”

“Yes, otherwise you won’t know how you look, will you?”

“Right.” So Gerald put his breast forms in the bra and looked at himself in the full-length mirror. This bra seemed to keep his breasts higher than the Glamorise bra.

“Oh, I really like that,” Linda said. “See how it gives you such a nice rounded look. Definitely you’ve got a good eye for what fits you.”

Gerald felt ecstatic. It was true. He liked the way he looked in the bra. He liked the way the bra made him feel. Really sexy but also elegant. A refined, sexy elegance that would make him definitely proud to know that he was wearing this under a blouse or dress. Plus the bra fit really nicely. “I love this bra, Linda.”

“Good. Now try on the others.”

Gerald took off the ivory colored bra and put on a beige bra. “This is also very nice, but I think I like the first one more.”

He continued trying on the remaining bras. One of the other bras got him as excited as the ivory bra. It was of a flowery fabric with a range of different shades of pink. “I love this one as much as the ivory bra,” Gerald said.

“If I were you I’d buy both of them. Then you don’t have to choose between them.”

“You’re right,” Gerald said. “I’ll get them both. Then I’ll just have to decide which of the two I wear when I’m in the mood to wear a different bra than my Glamorise bras.” He now conjured up a vivid encounter with the women. “Tonight I’m wearing my new bra,” Gerald would begin the conversation. “What did you get?” “An ivory colored Wacoal Embrace Lace bra.” “Joan didn’t get it for you?” “No. I’m buying my own bras now.” “Good for you, Gerald.” “I also bought a pretty pink bra with flowers on it. I like that one just as much as my new ivory bra.” This was going to be so good. The women would rally around him making him feel like he was truly one of them. Then, with this success he’d be motivated to go out of his way to learn other things that women like to talk about with each other.

***

A couple of weeks later was a dinner party at Glen and Pamela’s house with several other couples including Debbie and Bruce. While a roast was cooking in the oven the men congregated in the den and the ladies sat in the living room. This time Gerald made no effort to be with the men. Joan had directed him to wear a light blue dress that she had picked out for him though she had left his underwear up to himself. Now he triumphantly had decided to wear his new ivory colored bra and he couldn’t wait for an opportunity to tell the ladies about his new bra.

Gerald sat on the sofa between Debbie and Janet. He had been very careful to sit down smoothing the skirt of his dress underneath him while keeping his knees together. He was confident that he had managed that maneuver as well as any of the other women. Now Debbie, he and Janet sat in a row with their stockinged legs and heels all at the same slight angle. After some various conversations Debbie turned to Gerald and said, “So what’s new with you Gerald?”

With glee, Gerald said, “I bought myself a new bra.”

Debbie looked a bit puzzled and Gerald added, “Joan bought my other bras. This is the first time that I bought a bra by myself.”

“That’s very nice, Gerald,” Debbie said.

Gerald waited for the women to ask him about his new bra but since no one said anything he said, “I bought two bras that I really like.” Gerald could see that Debbie was smiling.

“What did you like about them?” Debbie asked.

“Well, first I found some bras that I thought were pretty. Then I tried them on and found that two of them were right for my body.”

“What do you mean by right for your body?” Debbie said.

“You know, for my body. They’re bras that fit me really well and achieve the look I’m hoping for.”

“What look is that?”

“I guess I’m going for a sexy yet elegant look?” His reasons for liking the bras he had bought had seemed so clear to him at the department store. Now he felt that the ladies didn’t understand what he was talking about. He looked at Joan to see if she would help him. What was going wrong he wondered? Wasn’t this a girl’s conversation?

There was silence and then Gerald felt himself getting dejected. He had had such high hopes that this could be an ice breaker and that the women would embrace him as one of their own. He looked up to see Glen walk through the living room to the kitchen, and then he heard Joan say, “Are you wearing one of your new bras now?”

“Yes,” Gerald said. He saw Glen shake his head. For sure he now had something to report to the other men.

“What one is it?”

“It’s an ivory colored Wacoal Embrace Lace bra.”

“I have one of those. It’s a very pretty bra,” Janet said. “I only wear it on special occasions. It’s not one of my everyday bras.”

Gerald couldn’t believe his ears. He and Janet actually wore the same bra. “But what is your everyday bra?” Gerald said.

“I’ve been wearing Flower Bali bras since I first began wearing bras,” Janet said. “I’m wearing one now. I like the look it gives me.” She sat up straight and indicated her bust with the sweep of her hands.

“Yes, you can’t deny Flower Bali’s are really comfortable and have a pretty design,” Debbie said. “I have a couple of those.”

“Gerald, your everyday bras are Glamorise, aren’t they?” Pamela said.

“Yes, Joan picked them out for me. I do really like them, but she encouraged me to explore bras on my own, which I did with the help of a very nice lady at the lingerie department. She helped me see that bras need to be more than pretty. They also should be comfortable and even more importantly help a girl achieve the look that she’s aiming for. My new bras I think give me a little bit sexier look, which I find that I really like.”

“The bra you’re wearing now definitely lifts your chest up a bit so that your boobs project more and no doubt will get you more man attention,” Debbie said, and the women laughed.

Gerald stole a glance at Joan wondering if she would be upset that her friends would suggest that he would be attractive to men. But she seemed to be unperturbed.

“You’ve made Gerald so pretty, Joan, that you better hope that some guy doesn’t come along who sweeps him off of his feet,” Debbie said.

“Lord help Gerald if I ever catch him with a man!” Joan said. The women laughed, but Gerald could see that she was serious. She obviously was being possessive of him in a way that he had never seen before.

“Getting back to bras, Joan,” Janet said, “are you a Glamorise girl also?”

“No, I wear mainly La Perla. My first impulse was that Gerald is a Glamorise girl. They have this really girly pink color that I thought makes a really nice statement about Gerald. Now that he’s done his own bra shopping, it confirms what I thought. He bought two pretty bras that are just as effective as the Glamorise bras in showing that he has an attractive set of round boobs. As you already noticed, with a nice tight blouse or dress, Gerald makes quite a sexy statement that men will appreciate.”

It was now close to dinner and the ladies got up. Pamela and Debbie came up to Gerald and Debbie said, “Pamela and I are going dress shopping next week. Would you like to join us?”

“Join you?” Gerald said, and then added, “What about Joan?”

“Do you need her permission?”

“No, I don’t think so. I’d love to go dress shopping with you two but wouldn’t you rather go with Joan?”

“No. We love Joan, but she’s a more in and out type shopper, like the way many men shop. Pamela and I like to linger and try on lots of dresses. Make a day of it and have some fun. We think you might be that kind of girl too, particularly after listening to your description of buying bras. We think it’ll be fun for us girls to shop together.”

“Then I’m in,” Gerald said. “I can’t thank you enough!”

All the way home in the car Gerald could not stop talking about how nice it was that he finally seemed to have made some friends. “You are so smart Joan,” Gerald said. “ You knew what it would take for the girls to see me as one of their own!”

“Debbie and Pamela are great shoppers. I’m sure you’ll enjoy your afternoon with them!”

“So I might buy myself a new dress. Is that okay?”

“Of course, Gerald. I’ve bought you a few pretty dresses, but it’s about time that you got to express yourself. Ask your inner girl which dresses make you feel pretty and get them.”

When they got home, Joan was unbelievably horny again and could barely wait for Gerald to take off his dress before she threw him down on the bed and made love to him. As she pumped away on his erect penis she said, “The whole evening I’m looking at this pretty girl thinking that she’s going to be mine tonight. Mine to ravish!” Joan was out of control excited on top of Gerald and as he tried to concentrate on his own climaxing suddenly Joan began screaming and cumming on her own. As she pulled off of him leaving his boner to himself, Gerald said, “But what about me, Joan? You’re frustrating me!”

“Goodnight, Gerald,” Joan said and faced away from him and crashed into sleep. Once again Gerald was left with having to go to the bathroom and finish what had been started. He wondered what would have happened if he had climaxed first. Would Joan have accepted it if he just rolled over and went to sleep? He doubted that.

***

Gerald had a hard time deciding what outfit he should wear to go shopping with Debbie and Pamela. He decided that a skirt and blouse offered him more flexibility in changing into outfits so he elected to go with that. Wearing pantyhose also made sense and with Joan’s help he did his makeup and hair. “I’m so nervous,” he confided in Joan.

“Debbie and Pamela are very easy going. Don’t over think it. Just allow yourself to be one of the girls and you’ll do fine.”

Debbie came by in her car and picked up Gerald who sat in the backseat while Pamela was in the front passenger seat. The two women were in a good mood that helped ease Gerald’s nerves. “You look very pretty today, Gerald,” Pamela said.

“Thank you. Joan helped me to get ready. I’m so excited.” Gerald had a purse with his wallet, lipstick, compact, hairbrush and a few other things in it, that he clutched tightly. The previous times he had used a purse was at the dinner with his parents and when he went bra shopping. He felt very grownup and sophisticated having a purse and shopping with the ladies.

They arrived at a large upscale department store and Gerald entered into it with Debbie and Pamela. In front of them were the perfume counters and Pamela said, “Let’s explore.”

Following the lead of Debbie and Pamela, Gerald joined in with them as they discussed various scents with the saleswomen and allowed them to spritz their wrists with perfume. “What is your favorite scent, Gerald?” Debbie asked him.

“Favorite scent? I don’t know,” Gerald said.

“The we must find you one,” Debbie said. “Every girl has a favorite scent. Even if you don’t wear it every day, you can put some on your lingerie or especially on your nighties and it will show Joan what kind of girl you are.”

They went through a dozen scents until Debbie and Pamela decided on a fragrance for Gerald and he agreed that it would be perfect for him. He bought a small vial of it and the ladies made their way to dresses on the second floor. While they were walking there, Pamela said to Gerald, “I can’t help but admire how nicely you walk in heels. One would think that you’d been doing it your whole life.”

“It’s Joan. She made me practice it over and over until I was good at it. Now it seems second nature to me. She always has me wearing heels. Never flats, except at night she bought me fluffy pink slippers to wear.”

“Your mannerisms have gotten to be those of a girl, I think,” Debbie said.

“I agree,” Pamela said. “Besides your walking, your arm motions are more like those of a girl than a boy. Is it a problem for you at work?”

“I’ve been overcompensating at work, but now I’m giving serious consideration to just coming out as a girl at work. It’s getting to be too hard to pretend I’m a man when I spend most of my life being the girl Joan wants me to be.”

“That’s a big step.”

“Yeah, but to tell you the truth, I feel like I’m making some good friends among the girls, like the two of you, so I might as well just go all the way to being a girl. It will be a relief to no longer think that I have to be a man and do men things.”

“Well, if it’s any consolation to you Gerald, you seem to me to be as much a woman as any of the wives in our group.”

“I’ll second that,” Pamela said.

It was clear that the handwriting was on the wall. Gerald had passed a tipping point where the people who had previously known him as a man, now thought of him as being a woman. Perhaps this was Joan’s intent all along. She wanted him to become a woman and she found a way to make that happen without struggle or fight. Gerald realized that maybe the answer to why he never said no to Joan was because she was making him do what he subconsciously wanted to do. But how could she know more about his own mind than he did? No, it had to be more complicated than that.

Gerald and the ladies arrived in a group of sections containing dresses from different manufacturers. Gerald followed Debbie and Pamela as they walked through the racks of dresses and skirts looking for items that caught their eye. “See any dresses or skirts that you like, Gerald?” Debbie said.

After a few minutes of looking, Gerald said, “This one seems pretty.” He took a size 14 off the rack and held it up to look at. It was sleeveless, blush colored, fit-&-flare with an illusion round neckline and floral lace detailing throughout.

Debbie and Pamela came over and examined the dress. “It’s a very pretty shade for you. Let’s see, back zip closure, fitted waist, and a lined full skirt,” Debbie said.

“You’ll definitely have to try it on Gerald, but first give us a second to find some dresses also.”

“Oh, sure,” Gerald said. This was turning out to be as much fun as he had hoped it would be. Joan was right about how easy-going Debbie and Pamela were.

Debbie and Pamela found dresses they wanted to try on and the three of them headed to the fitting room. They crowded into one midsize changing room with a large mirror on the wall. Gerald found himself to be especially excited that they would all be changing into dresses together. It seemed like exactly the kind of special girl thing that he was hoping to be a part of. Debbie and Pamela were both wearing dresses and they reached behind their backs and unzipped themselves and then pulled their dresses over their heads. Gerald unbuttoned his blouse, unhooked his skirt and took it off. The three of them were all wearing bras and pantyhose over their panties. Gerald had decided to wear the bright pink Glamorise bra and Pamela said, “That’s the ultimate in feminine bras, Gerald. Joan has such a good eye for what looks good on you.”

Gerald focused on the bras of the two other women. He could see how their breasts rested within the cups and were supported by them. The close proximity between the three of them in the small space meant that it was almost impossible for them not to touch each other. Gerald’s arm and chest bumped against the breasts of the women in their bras and Gerald felt a stirring in his penis. Oh no, he thought. This wasn’t supposed to happen. He’s a woman now. What would Bruce and Glen do if they knew that he was getting aroused with their wives. They’d kill him.

“Maybe this is a bit too crowded for the three of us,” Gerald said.

“Crowded?” Debbie said. “No, I don’t think so. Do you think so Pamela?”

“No, not at all. Why do you think it’s crowded Gerald?”

“We’re sort of touching each other a little, aren’t we?”

“But we’re all girls, Gerald. Girls often are affectionate with each other. It’s just the way we are. We’re not like men who often don’t like to touch each other. Since you’re a girl now, Gerald, you’re free to relax and let yourself be one of us. Be affectionate with us. Girls love to hug each other. It’s what we do and it’s what you are welcome to do.”

“Yes. Let’s have a little group hug and then we can try on our dresses,” Debbie said.

Debbie and Pamela each put an arm around Gerald and then their other arms around each other so the three of them were facing in towards each other. Their three bras holding their breasts pushed up against each other. “That’s more like it, Gerald,” Pamela said.

“Isn’t this nice?” Debbie said.

“Yes,” Gerald said, though he found himself getting excited to be so intimately touching the women. The view looking down on their bras and seeing how his breasts touched theirs was captivating. He felt a couple of pulses in his penis that suggested that it was going to form a boner and he forced himself to think of what Bruce and Glen would do if they found him getting turned on by their wives.

The hug broke off and the three of them sat down on the bench, with Gerald in the middle. To his relief, he felt the sexual tension in his penis subside. “Can I ask you two a question about relationships? About Joan and me?”

“Sure, Gerald, what is it?”

“The thing is, I’m okay with me being a woman now, but part of that is that Joan’s taken on the role of husband in our marriage and I’m clearly the wife now. I’m now exclusively doing the cooking, food shopping, most of the cleaning, all the laundry. That seems kind of chauvinistic on her part, but even worse is that now she’s treating me more like a sexual object than a thinking person. She makes love to me whenever she wants to and the moment she climaxes she ignores me and my needs. Isn’t this wrong? Shouldn’t she know better than to treat me like that?”

Debbie and Pamela looked at each other and laughed. Debbie said, “We’re afraid to tell you, ‘welcome to the club.’ This is what most women have to go through. While I love Bruce and he is a good friend and companion, he also sees me as being a nice receptacle for his sperm, a wonderful warm sexy body that he gets off touching and looking at. He loves my femininity in that sexual way. For his part, he thinks that the most important thing he can do for me is supply boners. Don’t get me wrong, I do love his boners, but there are many things missing from our relationship that I would love to have from him, but instead I get them from my girlfriends. That’s the intimacy that Pamela and I talked about, and for example, the three of us share by going shopping together.”

“I feel the same way about Glen,” Pamela said. “He has an amazing cock and he’s very skilled at using it and he’s taught me a lot about how to pleasure him. But Glen is no woman. He doesn’t get the things that we get. He mainly sees me as providing a female body with all its wondrous curves and beauty that he can use for his entertainment.”

“So you think that Joan just uses me for my body?”

“You said as much yourself. When she’s horny she seeks you out for her entertainment. Otherwise she uses you to cook and clean for her. Welcome to the world of women, Gerald.”

“But what can I do about it?”

Debbie and Pamela laughed and Debbie said, “Gerald, really? That horse left the barn months ago when Joan started dressing you up in pretty dresses. Why did that happen? It’s safe to say that you either wanted to relinquish your manhood or you weren’t strong enough to stop Joan from taking it from you. Subsequently, you found yourself filling the role of being Joan’s obedient wife. You should know better than anyone how this happened to you.”

Gerald thought about what Debbie said. “I wish I knew what the answer was. Maybe I’ve always wanted to be a woman, but it took Joan to make it happen. Or maybe I don’t want to do anything that gives her a reason to leave me. Or maybe I’m doing it because I love to see her get what she wants. Regardless, it is a bit of a shock to fully realize that my male life as I knew it is over. I’ve become a woman now and ahead of me for the rest of my life is a woman’s role in my marriage and with my parents and my friends.”

Debbie and Pamela spontaneously put their arms around Gerald and hugged him. Since they were still just wearing bras, he felt the heat of their naked arms against his flesh and he sensed a pulse again in his panties.

“Thank you, Debbie and Pamela. The thought that I’ll have the two of you as my women friends gives me hope for the future.” Gerald suddenly was overcome with emotion.

“Perhaps we should try on our dresses now,” Debbie said getting up.

“Good idea,” Pamela said.

They each slipped into the dresses they had found and stood in front of the mirror. Gerald instantly fell in love with the dress he was wearing. “Oh my, I’m just crazy about this dress! Do I look as good as I think I do?”

“Even better,” Debbie said. “It shows off your figure perfectly.”

“I think it’s made for you, Gerald,” Pamela said. “Joan is going to love you in it. She’s going to think that you’re very pretty.”

Suddenly, looking in the mirror, Gerald saw everything clearly. He had agreed to wear the pretty dresses Joan had wanted him to wear because he loved the fact that his beauty would make her happy. And now that he had become a woman, he understood the joy a woman can feel in being pretty and have her husband desire her. He exulted in the fact that he was now Joan’s wife and he felt joy and excitement in the fact that he could devote the rest of his life to being the sexy woman that Joan desired.

The End