The Suitcase - 3
By

Pamela

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Greg spent Sunday anxiously anticipating a call from Jill. He fought off his usual tendency to expect the worst. Jill had more than once affirmed her desire for him. Why couldn’t he accept that at face value? He would, except for the fact that he was accustomed to seeing himself as boring. He expected that Jill would come to that realization as well. But had he been boring? Not really. He had some dimension to himself. He had more interests than just Venetian blinds. He could hold a conversation with Jill. Moreover, hadn’t Jill emphasized that she liked him because he preferred to take on a passive role? She enjoyed having no competition for the leadership in their relationship. By preferring to take a back seat to Jill’s assertiveness, Greg became ever more attractive to her.

To his great relief Greg received a text from Jill at ten o’clock at night. It was a photograph of her wearing his suit. There was a hint of a smile on her lips. An accompanying message said, “I’m dressed for the cat funeral. A somber affair!”

Greg studied the picture rejoicing in the improbable fact that the gorgeous woman in the picture wanted to be his friend. He saw that she was wearing a tie. The lapels of the suit jacket sat out a bit odd until he realized that her breasts were pushing them out. The trousers were also slightly off, probably due to her having a woman’s butt. All in all though she was a striking figure. As much as he had been aroused by her feminine beauty when he had first seen her at the airport, he now felt a strong undercurrent of desire to be… what exactly? Her girlfriend? This was a new emotion and he had to stop and think what it was. It dawned on him that by wearing a suit, Jill was creating space for him to approach her from a feminine direction. That was exactly the emotion. He wanted to fulfil Jill’s desire for a female presence in her life that would complement her wearing a suit. His own desire to dress like a girl would not be done in isolation from Jill’s feelings. No. Jill and he had motivations both separate and together. Though he couldn’t see clearly into the future, he sensed that in this case the whole was going to be much bigger than the sum of the parts.

A minute later another text arrived, “I love wearing your suit, but you can see that it needs some alterations! Felix, (my poor brother), misses his departed cat. I’ll stay tonight and go directly to work tomorrow. Miss you!”

Greg wrote back, “I loved you in the suit. So handsome!!! I miss you too.”

She wrote back, “Meet me Wednesday afternoon at four to buy a suit?”

He replied, “Love to.” He’d have to get permission from the shop owner, but Wednesday was always a slow day in the Venetian blinds industry.

“Great! Where?”

“Ariston. The best shop by far!” Greg wrote.

“See you then. Good night.”

“Good night.”

It would be three whole days until Greg could see Jill again. It made him a little sad and frustrated. But he didn’t want to be a pain. Pouring his self-pity on Jill would be the fastest way of losing her. He’d have to follow her lead, regardless of what he wished for himself.

***

On Wednesday afternoon Greg arrived at Ariston a few minutes early and waited out in front. He was wearing jeans and a nice shirt. Every day now he wore a bra under his shirt – not only because it fulfilled his own desires, but because he knew how much it pleased Jill. Wearing a bra and panty each day was important to enable him to become fully acculturated to wearing the underwear that he would soon be wearing for the rest of his life.

Jill arrived full of energy a few minutes after Greg and embraced him giving him a quick kiss on the lips. “My Greg, you’re so punctual. I love that.” Jill was every bit as beautiful or ‘handsome’ as Greg remembered her being. She was wearing the outfit she wore as manager of the bowling alley. “This should be so much fun. I loved wearing your suit but it didn’t quite fit me.”

“I know. I could see your lapels popping out in the photo.”

Jill laughed. “My boobs wouldn’t cooperate! My derriere also had a bit of a time fitting in.”

“Still I loved seeing you in a suit. Who tied your tie?”

“My brother.”

“What did he think of you wearing a man’s suit?”

“He’s a dear. He thought it was cool. He believes in live and let live. Shall we go in?”

“Sure.”

They entered Ariston. The furnishings were plush with large sofas and a display of mannequins wearing expensive suits. An impeccably dressed salesman about Greg’s age approached them. “So what do we have here?”

He was looking at Greg and was surprised when Jill said, “I’m looking for a suit.”

“You’ve so made my day! Ohmygod! By all means have a seat. I’ll be back in a second with champagne and then I want to hear your story. By the way, I’m Roger, and you are?”

“I’m Jill and this is Greg!”

“Such a pleasure, Jill and Greg!”

Roger ran off and Jill said to Greg, “This place is incredible.”

“I know. I’ve bought shirts here, on sale. Their suits make men look fabulous. You’re going to look amazing in a Tiger suit.”

Roger came back with a bottle of champagne and two glasses. As he set them down in front of Greg and Jill and poured, he said, “Jill, let me guess what you’re looking for. Power? Am I right?”

“Yes, Roger. I want a power suit. Everyone should know that I’m in charge. Classy, sexy, manly. Capeesh?”

“I’ve prayed for a day like this! A customer like you! I want to dress you baby!” Roger said this with exaggerated excitement causing Jill and Greg to laugh.

“We’re on the same wavelength,” Jill said.

“Sip away Greg while I take Jill on an adventure!”

Roger led Jill to the collections of suits and circulated through them making comments as he went. He stopped in front of a rack and said, here is one of two possibilities that are perfect for your complexion, your height, your body, and your power-hungry needs! This slim twill suit in super 110 wool. The jacket has slim notch lapels, two-button closure, slanted jetted flap pockets, and side vents at the back. The low rise and slim leg trousers are made of premium Cerruti fabric.” Roger lifted a black suit up and handed it to Jill.

“Oh, my,” Jill said, “the fabric is sensual.”

“The alternative is this slim-fit suit in stretch wool.” Roger took a charcoal gray suit off of a nearby rack and held it up. “The lapels are wider, and it’s also two-button closure with side vents at the back. The trousers are made of premium fabric by Marlane. You can’t go wrong with either of these.”

Jill felt the fabric. “It’s luxurious.”

“These suits are speaking to you. Now you must try them on.” Roger measured Jill’s chest and waist and laughed quietly. “You’ll be a challenge for Salvatore! But he loves challenges!”

“Salvatore?”

“Our tailor. Your measurements are unusual. But no mind. We’ll start with a thirty-six regular and go from there. Salvatore is a genius. By the time he’s done altering, you’ll think that you were born in the suit!”

Roger took a light blue shirt from a display and handed it to Jill. “You’ll need a real shirt. The fitting room is there,” Roger pointed to a corner of the store. “Try the suit on and let me see.”

Jill returned to where Greg was sitting, took a sip of champagne and said, “Come with me Greg. Help me.”

“Sure,” Greg said jumping up. He had had a couple of glasses of champagne and was in good spirits. He followed her into the dressing room and closed the door behind them. “Shall I get the shirt ready for you? There’ll be a lot of pins.”

“Please.”

Greg opened up the shirt and carefully removed the pins and miscellaneous plastic tags on the buttons. While he did so, Jill lifted her shirt up over her head exposing her bra underneath. This was the first time Greg had so much as glanced at Jill’s chest and the sight of her full bosoms perfectly held within the fabric of the bra cups produced an electric pulse that ran from his heart down toward his groin. He recognized the bra as one of those he had seen in her suitcase.

“I wore a bra today,” Jill said, “though I debated a long time whether I should or shouldn’t. It didn’t seem to make sense to have my boobs bouncing around at the alley. I do intend to get into the practice of binding my breasts. I’ve started to search among the different possibilities. I’ll have to explain that to the tailor.”

“How do you do that? I mean breast binding?”

“It’s basically an elastic top that will flatten my breasts.”

A number of emotions ran through Greg. On the one hand he desired to gaze at Jill’s breasts and fondle them if she were to encourage him. On the other hand, the more that he and Jill were drawn toward each other, the more he felt it was his responsibility and privilege to be the one who brought the womanly breasts to their relationship. He was destined to be the pretty one. The one with the pretty dresses and sexy underwear. The one with the feminine hairstyle, make up and shoes. It was to be his turf and he was thankful that Jill was surrendering this part of their relationship to him. Of course, he himself had already forfeited to Jill whatever masculine territory he might have occupied. She had the commanding role and he had neither the desire nor the fortitude to contest that reality. Her wearing a breast binding was her way of doing the same for him.

“You won’t be upset by my appearing to have a man’s chest?” Jill asked Greg.

“Of course not,” Greg said. “I want to be supportive of whatever masculine impulses you have. I can’t wait to see you in the power suit.”

Jill put on the formal shirt and buttoned up the front. Her breasts were clearly not what the shirt was expecting. “Let me ask Roger if he’s got something you could bind them with for the fitting,” Greg said.

“Great idea!”

Greg sought out Roger. “Jill and I were wondering if you had something she could bind herself with for the fitting? You know, her breasts are a bit in the way.”

“Of course, of course, of course. I’m sure Salvatore can offer something.” Roger went through a door to the back of the shop. Greg overheard some discussion and Roger came back with a white elastic garment. “We’re in luck. This is a sleeveless chest vest that the ever-resourceful Salvatore keeps for just this occasion.”

“It looks perfect,” Greg said. “Thanks!”

Greg brought the vest to Jill. “This should work. It’s just what I had in mind!” Jill took off her shirt and handed it to Greg. Then she unhooked her bra and gave it to him to hold. Greg had his first ever look at Jill’s breasts and he was shaken to the core by their perfect shape and delightful feminine essence. Thoughts of burying his face in them, holding them, and admiring them took off like a rocket in his mind and he did everything he could to clamp down on his fantasies and not get carried away. If a time came when Jill would want him to fondle her breasts then it would come. If not, then it wouldn’t come. Get control of yourself he told himself! Jill put the vest on over her head, stretched it out a bit to fit past her shoulders and settled it over her breasts. They immediately flattened against her chest significantly lowering their outward projection. “So cool!” Jill said.

“How does it feel?” Greg asked.

“Not so bad. I think it’s sort of like a bra. It’s actually quite comfortable and it’s so nice to no longer have my big boobs out in front of me! I’ll have to buy a few of these.”

Jill put on the shirt again and buttoned it up. This time it fit dramatically better than it had. Jill smiled and admired her profile in the full-length mirror. “Woo woo, Greg. Look at that guy in the mirror!” Jill laughed gleefully.

Greg smiled. He felt glad and excited that he got to be a witness to Jill’s first steps into the kind of masculine persona she longed to have. Jill stepped into the pants and buttoned them up. She tucked the shirt in and then put on the jacket. She and Greg stepped out of the changing room.

“My oh my,” Roger said, coming over to look. He made some adjustments of the jacket. “Very flattering. Of course Salvatore will have a lot to say about where it should be altered. Walk around a bit. Look in the mirrors.”

Jill strolled around the shop and after a few minutes, Roger said, “Now let’s try on the charcoal gray suit.”

Jill returned to the dressing room and came out again in a few minutes wearing the second of the two suits. “Very lovely,” Roger said. “Walk around and absorb the suit’s essence!”

After a few minutes, Jill asked Greg, “So what do you think? Which do you like best?”

“You’re so handsome in both of them! Based on color I’d go with the gray suit. It’s a dark gray and so neither gray nor black.”

“My thoughts exactly,” Jill said. Greg was happy that they were on the same page. “What do you think Roger?”

“Like Greg said. You’re handsome either way you go. I’d say to buy both suits! Shall I get Salvatore?”

“By all means,” Jill said. “I’ll take this suit and who knows, maybe I’ll come back another day for the other one.”

Roger fetched Salvatore, who came bustling into the room. When he saw Jill he said, “My dear, that’s a beautiful color for you. I’ll have some work ahead of me to accommodate your unique shape, but it will end up beautiful, even striking.”

Salvatore had Jill stand on a small platform and he went to work with chalk and pins customizing the suit. He was a master of his craft. When he was done he said, “I’ll need a week and it’ll be ready to try on. Maybe a bit more work after that, we’ll see.”

***

After paying for the suit and shirt, and sampling a bit more of the champagne, Jill and Greg left the store. Greg was apprehensive that Jill would say goodbye, but to his relief she said, “We deserve a nice evening together. Let’s drive to my place and have a glass of wine. Then I’ll take you out to a wonderful Cuban restaurant. They have Camarones al Ajillo to die for. It’s shrimp sauteed in a garlic-infused wine sauce.”

“I’d like that very much,” Greg said.

They drove their separate cars and parked at Jill’s house. Jill changed her bowling shirt to one of Greg’s. “This is one of my favorites,” she said.

“And it was one of mine too. You look really nice in it.”

“Have a seat.” Jill poured them each a glass of Pinot Grigio.

They sat together on the sofa sipping wine. “How old is Felix?” Greg asked.

“He’s a year and a half younger than I am.”

“He likes cats?”

“It’s a long story. His last girlfriend left him her old cat. He had a love and hate relationship with the cat for the last year. But when it died, it turned out he discovered that he had become quite attached to it. Probably because it was his last connection to his ex.”

“It’s nice that he can rely on you to help him.”

“We’ve always been close. I told him that I had called off my marriage to Barry. That freaked him out.”

“You hadn’t told him?”

“No. I’ve been waiting to tell my family. I told my friends as soon as I got back from Toronto. My family is a different story. I’ll tell them when the time is right. I’ll have to make it clear to them that Barry isn’t right for me. My parents adore him. He’s very polite to them. He fits perfectly into the world that my parents expected me to inhabit. I was raised to be a pretty and sexy trophy bride. My mother taught me to take advantage of my innate sexuality to please men. She had me wear the sexiest lingerie, feminine dresses, jewelry, perfume. Everything to make it clear to any male that I was a girl through and through. From that she figured I’d meet the perfect husband. That turned out to be Barry in their minds. But inside I always had some doubts. I didn’t want to just be pretty or appreciated for my girlish charms. I felt encumbered by dresses and heels and having to apply makeup and keep my hair perfect. All the stuff that girls do. I allowed myself to believe that I really loved Barry because there was no alternative reality that I could contrast with the one I was raised in. That whole world exploded in Toronto when Barry showed me that our perfect love was a lie. That was the catalyst for my awakening to my true self. I thank my lucky stars that you and your suitcase were there to be the perfect life preservers!”

“And that worked out for both of us!” They sat silently thinking about how lucky they had been to meet each other when they did. “So tell me what your brother said when you told him?”

“He said he never liked Barry. Guy to guy he thought Barry was a womanizer. He figured that Barry wanted to marry me so he could check off ‘beautiful wife’ from his life’s accomplishments. Then he’d be able to check off ‘family’ when I gave him a couple of kids. At no point would he see me as the great love of his life that he would never want to hurt.”

“Felix never spoke up before?”

“I never asked him for his opinion. Unsolicited advice is dangerous in families.”

“When are you telling your parents?”

“Felix and I talked about that. We agree that it’s best to let them know when I no longer have one foot in the girls world and one in the boys world. That would give them an excuse to think that this is just a passing whim. No. When I tell them, they’ll have to deal one hundred percent with the new me.” Jill was stirred up and Greg was overcome with affection for her. Jill looked at him and said, “And I want you by my side when I tell them. I want them to see firsthand exactly the kind of man that’s right for me. A man who fully appreciates me for who I am and compliments my new-found persona.”

“I’ll be happy to be with you!”

“So now you can see the outlines of the next few weeks. I need to complete my wardrobe. As I fill it out I can give you whatever of my girl clothes that you want. Now that I know about binding I won’t need my bras and you can have them all. Also my slips, blouses, skirts, and dresses. I hope you don’t mind but I’ll just empty out my closet and donate it to you. I hope you’ll come with on shopping trips like we did today. Help guide me to the boy clothing I’m missing.”

“Of course. One thing you’ll need to buy are boy shoes. My foot size is different than yours so my shoes won’t fit you too well. You especially need to get dress shoes to go with your new suit. Also, you know that there are other underwear choices besides boxers. You could get jockey shorts, for example.”

“I’d love to get them. White underpants like my father and brother wear. I did the laundry a lot as a kid and I saw what they looked like. I remember being amazed at how much more secure the cotton fabric was compared to the materials in my panties. I loved the thick elastic band and the absence of little bows and fancy colors seemed exotic and cool to me. I love the pure functionality. The little doorway that underpants have so boys can pee was especially neat. I was even envious that boys got to wear them and I didn’t.”

“That’s so weird, since the few times I saw my mom’s or sister’s panties in the laundry I was fascinated by them. I would have loved to study them closely. Take a good look at the little bows on them and the lace. When I got older I was jealous of girls and wished that I could be wearing panties.”

“We’re like so made for each other!”

Greg shivered with excitement upon hearing that. After a moment Jill began laughing and Greg asked, “What’s so funny?”

“Would you mind terribly if I got myself a jock strap?”

“With a cup?”

“A cup?”

“To protect a man’s … you know what.”

“Really? They have hard cups?”

“Yeah. Some do. Some are just to make sure it doesn’t flop around, but others have the cup so it won’t get in an accident.”

“How marvelous. We’ve got to go shopping for a jock strap with a cup.”

“The cup can be taken out. You can wear it with or without a cup.”

“Fantastic! I guess women with sons know about these things. I seem to remember that Felix had jock straps for gym class though if he had a cup I never knew about it.”

“Barry didn’t wear them?”

“No, I never saw Barry in a jock strap.”

“Probably because bowling isn’t a contact sport.”

Jill laughed gaily. “This is so much fun. We have lots to buy for you too. Shoes, for sure. Lots of shoes. They have to match your outfits. You need heels of several different heights. Rome wasn’t built in a day so you and I will have to work on these things for quite some time.”

“I can’t wait to take Bonnie’s course!”

“After the course is over we’ll be able to finalize our appearances.”

“So I can then wear dresses in public?”

“Exactly. And I’ll show up at the alley with my man’s haircut and clothes. I’ll get a nice big man’s watch to wear. It’ll be neat.”

“Then we’ll visit your parents?”

“Yes, though I’d be lying if I didn’t admit it’ll be terrifying!”

They sat silently thinking about the meeting and how it would go. Then Jill said, “Here I am going on and on about my family. But what about yours? When will you show them the new you? When will you introduce them to me?”

“You mean you don’t mind if I introduce you to my parents as being my girlfriend!”

“I do mind!”

Greg stared at Jill with horror. He had assumed too much. Jill saw his face and said, “Silly Greg! I want you to introduce me to your parents as your boyfriend! After all, I’m going to introduce you to my family as my girlfriend.”

“Yes, I’m sorry! I guess it will take some time to internalize our new roles.”

“I’ll be proud to be your boyfriend!”

“Like you said, it terrifies me to imagine how my parents will react to seeing me in a dress. They’re very conservative and religious and will take it hard. It’s anybody’s guess just how outraged and crazy they‘ll be. They might refuse to see me again, I don’t know and I hope not.”

“You said you had a brother and sister.”

“Yeah. My older brother will make fun of me, I’m sure, but ultimately will accept me for who I am. My sister is younger than me and I have hope that she’ll welcome me as her sister. That might just be a fantasy of mine, but she has always been the one sibling who was most vocal about rejecting my parents religiosity. I rejected it too, but kept it more to myself. I always admired her courage in standing up to them.”

“Now she’ll see that you also have courage.”

“Yes, except that it comes from you being with me.”

***

Jill drove them the few blocks to the restaurant. They ordered the Camarones and enjoyed them immensely. During dinner they talked about the many consequences of their plans for the next few weeks. They had friends who would be forced to make some adjustments. For Greg, he had concerns that the owner of the Venetian Blinds shop, Mr. Lutz, might not welcome him wearing dresses. His politics was a bit conservative, though Greg had never heard him say a disparaging word about the many gay people who frequented the shop. The other employees would be surprised, but not judgmental. Greg knew some of the customers and he hoped that they wouldn’t react negatively to his new appearance.

When the bill for their meal came, Greg started to reach for it, but Jill said, “No Greg. I asked you out on the date and I’m paying.”

“I can help you pay for things.”

“I know you can and I like that you want to. But I imagine I earn much more than you and it gives me pleasure to think that I can take a girl out on a date. This is good practice for you and for me for that matter. In a few weeks I want you concentrating on being as pretty as you can be when we go out. I’ll handle everything else.”

Jills words were a powerful elixir. Greg felt ever more motivated to work towards being the prettiest girl he could become. “I was wondering, Jill, what my name should be. I’m not so sure that Greg will make sense once I wear dresses.”

“Good point. And I should no longer be Jill. That would be odd.”

“I would love it if you gave me a name. I would treasure it.” Greg laughed, “But not a weird name. I would want you to give me a pretty name.”

“I love the thought of naming you. How sweet that is!” Jill fell silent thinking of a name for Greg. “How about Lisa Hayley? I love those two names. There’s a famous bowler named Lisa.”

“Lisa Hayley is very pretty!” Greg said.

“After we take the plunge, I’m going to call you Lisa. Sometimes I might want to call you Lisa Hayley!”

“If I’ve been naughty?”

“Exactly,” Jill said laughing.

“What about your name?”

“Do you have any ideas?” Jill said.

“What do you think of Timothy or Terrence?”

“A bit too tame. I was thinking of something a bit tougher.”

“Wow. Okay. There’s Fess or Ryan.”

“Fess like in Davy Crockett?”

“What about Blake?”

“I like that. Yes. I could see me being a Blake.”

“Blake Ryan Cappels?”

“Blake Ryan Cappels. That has a nice ring to it.”

“Blake and Lisa. Lisa and Blake. That sounds like a nice couple,” Greg said.

It crossed Greg’s mind that one day – if Jill proposed to him as Blake – he would take her name and become Lisa Hayley Cappels. He prayed that more than anything else in life that would come to pass.

***

When they returned to Jill’s house, Jill said, “It’s not too late. Come in and relax a bit. We can watch a show.”

“I’d love to.”

Jill poured them each another glass of wine and they sat together on the sofa. Jill put her arm around Greg’s shoulders and brought him in close to her. She turned on the TV which came up on an old Edward G. Robinson gangster movie. Before Greg could settle in to understand what was going on in the film, Jill moved in and gave Greg a long passionate kiss. “I felt I owed you that since Felix interrupted our last kiss.”

“I think you over paid, but I’m glad that you did.”

“It’s nice to hear that. This is all new to me. I know how Barry behaved and the boyfriends I had before him. Quite frankly, they’re my role models for how guys express their desires with a girl. I hope to learn how to imitate them. I suppose that one of your goals will be learning the feminine response to male desires. I guess I could try and help you but that might be difficult while I’m gravitating away from my former female posture.”

Greg could see what Jill was driving at. He couldn’t respond to Jill’s overtures as if he were the guy he had always been. No. He was now going to have to ask his inner girl to guide him in curtailing and controlling Jill’s male aggression the way any woman does. It was new and exhilarating and he hoped that as time went on he would find a feminine way to seamlessly adapt to Jill’s new-found masculinity.

“I understand. I’ll let you know if you’re being too rapacious!”

Jill looked at Greg and smiled. She was thinking how she now understood how men can take advantage of girls who haven’t figured out how to fend off their advances. Greg was always going to have trouble countering her sexual demands on him. He was going to be the kind of girl who was in over her head with a man who had designs on her. Jill felt an impulse to want to protect Greg from her own desires. She would have to make sure that she never hurt him. He was a fragile teacup. That both attracted her and restrained her.

Jill resumed kissing Greg and after a while her hand went inside his shirt and discovered he was wearing a bra. She greeted the discovery with a burst of excitement and rising passion. It was a joy to hold this lovely feminine creature who had taken to wearing bras as a matter of course. Jill had to stop kissing Greg and de-escalate her advance on him. It would be wise to hold off conquering him until they had fully assumed their new identities. This was all about creating memories that she could cherish. Soon enough she’ll be Blake and he’ll be Lisa and they’ll have full license to explore the depths of intimacy that their names imply.

“Next week you start with Bonnie,” Jill said. “I’d like to wait until after you’ve completed her course before we date more seriously.”

“You mean after I’m Lisa?”

“Yes. Don’t you think that that’s for the best? It’ll allow us to get to know each other as we really are meant to be known.”

“Sure, Jill. We’ll still see each other?”

“Of course. I want you to join me for the fitting of my new suit. Also we should do some shopping excursions together to help each other out.”

“Okay. I’m sure that you’re right about this. I do want what’s best for us in the long term.”

“Good.”

***

Greg and Jill met up at Ariston midweek. Roger was excited to see them and fetched champagne. “You’re going to be thrilled. Salvatore showed me what he’s done. It’s so fine.” Roger fetched Salvatore who greeted them and gave Jill the suit to try on. When she came out of the dressing room Greg gasped with excitement. She looked like a million dollars. Salvatore checked his handiwork. “She could be Fortune 500 chief!” he said.

“Nothing screams power more than a well-tailored and well-made suit!” Roger said. “It’s like you stepped out of GQ.” Jill stared at herself in the mirror. Paroxysms of delight ran through her as she observed how the suit’s masculinity obliterated any sense of the woman underneath.

Greg was in awe. As intimidated as he had been by her beauty as a woman, he saw that as a male figure wearing the Tiger suit Jill was even more powerful. An increased sense of helplessness arose in Greg as he recognized how dominant a figure Jill had become. He would have to learn to use the full arsenal of female wiles to not be totally subsumed by her.

“I’m so in love with this suit,” Jill said. “I don’t see anything that needs further altering. What do you think?”

Salvatore said, “It’s perfect. I’ve out done myself!”

“It’s pure genius,” Roger said.

“There’s no describing how handsome you are,” Greg said.

Jill stared at herself in the mirror for a long time. Greg saw what an important moment this was in her life. She was beginning to see what she had been looking for. A baseline masculine image which would form the center of how she saw herself. Greg fervently hoped that within a week or two he too would acquire a self-image that depicted how he wished to see himself in the future. In his case, it would be of a somewhat delicate and pretty, feminine girl.

***

Greg had a tough time making room for the girl clothes he had taken from Jill. It was a tight squeeze to fit the many dresses, skirts, and blouses into his closet. Despite the tactical problems it created in his small apartment, he saw the wisdom of maintaining his own domicile for the time being. Rushing headlong into moving in with Jill could jeopardize all that they had achieved thus far. It was best to not force their relationship. Let it develop step-by-step on it’s own. Allow them as many bail out opportunities as they might need. If they did that, then by the time they were able and willing to commit to each other, they’d have a good chance it would be permanent.

In preparation for their new lives, Greg and Jill spent many hours shopping. They visited a dozen women’s shoe stores to find the shoes that Jill thought that Greg needed to own. Despite stares from other customers and smirks from the salesclerks Greg dutifully tried on the shoes and shared his excitement with Jill every time he found a pair that he liked.

Each new pair of pretty shoes raised the excitement with which Greg anticipated his upcoming transition. “Oh my God, I’ll be able to wear these shoes!” was the common thought that filled his mind. Along with the shoes, Jill’s dresses in his closet, and the dresser full of underwear joined to form an ever-deafening chorus of clothing beckoning Greg to try them on and to wear them around town. He had to remind himself daily that in due course, the opportunity will come. Be patient.

Among the most amusing shopping experiences was their visit to a sporting goods shop so Jill could purchase her first jock strap. Like in Ariston, Jill had to explain to the salesman, Tony – according to his name tag, that she was the customer, not Greg. “What size cup are you?” Tony asked.

“How do you measure cup size?” Jill asked.

“Measure cup size?” Tony looked uncomfortable. “It depends on how big … I mean, how much have you got there?”

“Right. The cup has to hold my junk,” Jill laughed gleefully. She turned to Greg and said, “I was thinking of buying something to go there.” Greg’s eyes widened and Jill said, “One that’s at rest! Not an excited one!”

“Then I guess you have to plan for that,” Greg said.

“Good point. What’s the biggest cup you’ve got?” Jill said.

Tony took a box off a shelf and handed it to Jill. “This is extra-large.”

“Cool!” Jill took the cup out of the box and looked it over. She moved it toward her crotch and asked Tony, “Can I?”

“Yeah, I guess so.”

Jill held the cup up to where her private parts were and asked Greg, “What do you think?”

“I guess you’d rather have it too big than too small? Is that right Tony?”

“Well, yeah, you don’t want the circulation cut off. But you also don’t want it swimming around in there. You can always buy one and if you don’t like it buy another one. They’re only $7.95 each. Unfortunately, all sales are final with athletic cups.”

“I hear you,” Jill said. “I’ll buy the extra-large and if I need a smaller size I’ll get it later. So what about the jock strap it goes in?”

“You’ve got two choices. Either classical jock straps with straps around your thighs or the more modern compression shorts. They both have a pouch to hold your cup.”

“That’s easy. I’ll get one of each.”

“The size is usually based on waist size. I’m guessing you’re a medium. Your waist is less than 32 inches isn’t it?”

“It’s twenty-eight inches. Will my hips be a problem?”

“Gosh, I don’t know. The jock straps are stretchy so it’s a question of how much stretch. You definitely don’t want a loose jock strap. It could fall down while you’re exercising.”

“Can I see a medium?” Jill said.

Tony found one and took it out of a box and handed it to her. She held it up looking at the pouch. “The cup slides into there?”

“Yes,” Tony said. He took the cup and slid it into the pouch.

Jill took the jock strap and held it up against her waist. “Very nice. I think this will fit me pretty well.” To Greg she said, “It’ll be really nice to have this between my legs.”

Greg noticed Tony looking up at the ceiling. Jill turned to him and said, “May I see the compression shorts.”

“Of course.”

Tony found a medium on a rack and handed it to Jill. She took the cup out of the jock strap and put it in the shorts. “It’s so neat the way it fits in there. Very clever.” She held the compression shorts up to her waist and looked in a nearby mirror. “Okay. I’ll buy the jock strap, shorts, and cup. This is so exciting.”

After they left the store Jill said, “Once again I hope that I’m not freaking you out.”

“I think it’s great if you want to wear a jock strap with a cup. That should definitely help you feel like a boy.”

“Thanks, Greg, but I was referring more to you being alarmed at me putting some sort of substitute organ there.”

“Like the way I wear silicone breasts in my bra?”

“Exactly. I’m sure I can find a rubber or perhaps, silicone, penis to put in my jock strap. I like the thought of having that there.”

“I’d give you mine if I could,” Greg said.

Jill laughed, “Such a sweet thought. And I’d give you my boobs if I could!”

Greg got choked up. He gathered his emotions and said, “I think it’s only right that you give your jock strap something to protect. While it’s hard to see the future now, I think that it could pay many benefits in the future – I mean in how we relate to each other as a couple.”

“You’re very smart, Greg. I like that about you!”

***

After Greg and Jill had assembled their complete wardrobes, Jill noted that in a few weeks they would be fully responsible for their own clothing needs. Greg would have to have the skill, knowledge, and taste of any woman in choosing new outfits or new lingerie to wear. He could no longer count on the help and advice of Jill. Similarly, Jill should ideally have acquired proficiency in buying men’s clothing that suited her taste, with the caveat that Greg would oversee her choices. Afterall, it is not uncommon for a man to require the guidance of women in making a fashion statement.

Being a woman came with stereotypical baggage that Greg would have to internalize. Society viewed women’s natural talents differently than men. Even if there were innumerable counter-examples – such as he and Jill! – their transitions still led them to shift into the customary roles reserved for the opposite sex. Bit-by-bit Greg was seeing that wearing girls’ clothing was far from the only requirement needed in his transition. His approach to sex and fashion would have to change also. Looking ahead he could see that his friendships, household chores, driving, feelings toward children, athletics, and a myriad of other aspects of his life would have to adapt, as well. Being a man in women’s clothing is a lot different than being a man who has subsumed the ways of women into the fabric of his being. It was only the latter that Jill would find desirable and acceptable.

End Part 3