The Suitcase - 2

By

Pamela

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“My flight back home is tomorrow,” Jill said. “I was going to spend a week with Barry but decided to go home early after what happened. How long will you be here?”

“I’m here for a conference until Friday.”

“What’s the conference about?”

Greg braced himself for Jill’s reaction. “The conference is the biannual meeting of the Venetian blinds industry.”

Jill smiled, “You’re a blind guy?”

Greg laughed, “How did you know that joke?”

“My grandpa had a Venetian blinds shop in Chicago.”

“You’re kidding.”

“No. Grandma used to take me over there when she was babysitting me. I was young and didn’t really understand what was going on.”

“Can I ask what you do?”

“I manage a bowling alley.”

“Wow, a manager!”

“It’s a people job which I like. Employees and customers. I try to create a fun environment for everyone.”

“Do you bowl?”

“Yes. I’m pretty good. Do you?”

“Not very well, I’m afraid. But I wish I were better.”

“I’d be happy to teach you,” Jill said. “That would be fun.”

“I’d love that. If you need blinds …”

Jill laughed. “As a matter of fact you should come to my house and take a look at my blinds.”

Greg smiled at Jill. “For sure.” He relished everything about the future in front of him.

“It’s getting late and we ought to decide about our clothing. I’ve been wearing the same bra since I arrived in Toronto, so I’d like to have a couple of my bras back.”

“You mean I can keep some of your bras?”

“Yes, Greg. You love them so much and I have more at home.”

“I can’t thank you enough!”

“You can keep all of my panties. I’ve been wearing your boxers and I really like them. I don’t think that I have a need to feel the feminine feelings I’ve gotten from my panties. Since you really do love those feelings I think it’s right that you get a chance to express them. Your boxers give me a solid masculine feeling that I’m thrilled with. It’s new for me, like I said, but it does seem remarkably natural.”

“I can’t argue with anything you said. I really love wearing your panties and I love the feeling they give me.”

“Good. So we’ve taken care of our panties, boxers, and bras. As for the rest of my girl clothes, I won’t be needing my slips. I’ll leave you one of my dresses and one blouse and skirt. There are occasions where I need to wear a dress or skirt, though I hope to wear jeans as much as possible.”

“You can have as many of my jeans and shirts as you want. However, I do need my suits for the conference.”

“I’ll leave you my garter belt and stockings. There’s also my pantyhose that you might like to wear. I should take my makeup! You’re dangerous with it right now. I have a friend, Bonnie, who teaches a short course on makeup in Chicago and I’m going to enroll you. It’s five one-hour lessons in her beauty shop. Would you like that?”

“Sure. That sounds great!”

“She’ll teach you how to femininize your face. That kind of thing. She can also help you work on your hairstyle. Her salon also does great work with finger and toenails. You have pretty hands. I’ll bet you’d like to wear nail polish.”

“You really do know me.”

“As a girl I know what it feels like to want to be pretty. So it’s easy to project those feelings on you. From everything you’ve said so far, I think it’s a safe bet that I’m right about your instincts.”

Greg came to the inescapable conclusion that Jill was seriously staking out a future between them. She wasn’t just hot air. It was real. This caused a new surge of emotions to sweep through him and he fought off tears.

Jill smiled at Greg again. “You have a sweet sensitivity, Greg. You respond naturally and honestly without a filter. I love that about you. It’s refreshing to finally meet a man like that. You’re happy that I’m actually serious about our seeing each other again, aren’t you?”

Greg nodded his head.

“Well, I am.” Jill took her suitcase and filled it with the clothes that she needed. “Come with me to my room and you can take back your suitcase.”

“Okay. Should I put on pants and a shirt?”

“You might as well put the dress back on. I’ll zip you up.” Greg slipped the dress over his head and Jill helped him with the zipper. They went to her room where Jill went through Greg’s clothes keeping what she wanted. What was left over, Greg took in his suitcase.

They exchanged phone numbers and Jill said, “My flights early. We should say goodbye.”

“Of course,” Greg said

They looked at each other. Jill’s beauty was intimidating and Greg held back from embracing her. “Let’s take selfies,” Jill said.

“Really?” Greg said.

“Yes, I would like that.”

They took a few shots using their phones and then they embraced. Jill kissed Greg on the lips again. This time she lingered a bit and then broke it off. “I’ll call you Friday after you’re back in Chicago.”

As Greg headed back to his room his mind swam with excitement for the future. He took out his phone and admired the pictures of the two of them smiling. In one of them he saw Jill sneaking a peek at him. The warmth and affection he had previously seen in her eyes was captured perfectly by the photograph. Even though Jill had said he shouldn’t feel vulnerable, he did.

***

The next day at the conference, Randy said, “You got your suitcase?”

“Yes. Last night. Finally I can wear my suits.” While Greg enjoyed Randy’s company as well as that of the other guys, he would now have to restlessly wait several days until he could return home and hopefully see Jill again. Would she actually phone him like she said she would? It had always fallen on him in the past to call girls up to ask them out. Now he would be waiting besides the phone when he got back for her to call.

Greg didn’t know much about Jill but from what he did know he saw that she was much bolder than he was. He could never manage a bowling alley. It would require people skills and fearlessness that he didn’t possess. Jill had to have the self-confidence to make decisions affecting many people’s lives. That would be impossible for him. Thus, not only was Jill more beautiful than his previous girlfriends, but she also cast a large shadow over his meek and retiring personality. Why should she even like him?

The more Greg thought about Jill, the more convinced he was that he’d never hear from her again. She’d realize that he wasn’t as handsome as Barry – of course he’d never seen what Barry looked like – and she’d want a man with at least some decisiveness in him. Jill might like him as a friend, but only as a friend she could confide in like he was a girlfriend to her. Since she probably had many girlfriends already in Chicago, he couldn’t see why she needed yet another one – and especially one who is not even a girl!

Still, he wasn’t being entirely fair to Jill. Taken at face value, what she had said was that she liked him wearing her clothes and she liked his sensitivity. Perhaps even more telling was her admitting that she liked wearing boy clothes because of the masculinity that went with them. Just from the fact that Jill loved wearing boxers more than panties meant that she would run aground of normal guys who wouldn’t find that attractive. She’d have to seek out guys like himself who preferred panties. Hadn’t she said as much already?

It was tiresome to worry about what would be happening with Jill back home. As he often did, he’d expect the worse and if it turned out better than that, then he’d be happy.

***

When Greg’s flight arrived safe and sound in Chicago and he returned to his apartment he had all but abandoned hope that Jill would call him. Had he even met a girl named Jill in Toronto? It seemed like a fabulous dream. Except for the fact that half his suitcase was filled with her clothes. He was like the prince in Cinderella. The day after the ball he had a glass slipper to prove that his memories of Cinderella were real. Except that now Greg felt like Cinderella herself, hoping and waiting for the prince to show up.

Greg made room in his dresser and closet for Jill’s clothes. He had been afraid to fly home wearing a bra since he had once read of a woman whose underwire bra set off the metal detector. Imagine if he was patted down by a man who determined that he was wearing a bra! He now put a bra on, and then one of the nighties. He would find something to eat in his kitchen and spend the evening chilling out and hoping against hope that Jill would call him.

By eleven o’clock Jill hadn’t called and Greg got into bed and turned out the light. He fought off tears telling himself that even without Jill he had a lot to be thankful for. It was never a realistic fantasy to imagine that she would want to be his friend. He dozed off when he was awakened by the phone ringing. He answered, “Hello?”

“What are you wearing?”

“Wearing?” It was Jill’s voice.

“Tell me everything you’re wearing.”

“I’m wearing your panties and bra.”

“Mine? Aren’t they yours? Why would you wear someone else’s bra and panties?”

“Right. I’m wearing my bra and panties.”

“Is that all?”

“I’m also wearing my nightie.”

“You must look very cute.”

Greg laughed. “You’ll have to come see for yourself!”

“I intend to.”

“It’s so great to hear your voice!”

“I was going to say the same thing. Sorry for calling so late. Things got a little hectic down at the bowling alley tonight. One of my assistant managers had a family emergency. Just a typical day at the alley. If it isn’t one thing then it’s another.”

“I just love the thought of you running everything down there. You’re amazing.”

Jill laughed. “I love the thought of how cute you must be in your nightie. Pretty sexy I’ll bet!”

Greg laughed. “I do love being sexy. I’m so happy I have these sexy clothes to wear.”

“How was the rest of your conference?”

“To be honest, I had some trouble concentrating on Venetian blinds.”

“Why was that?”

Greg laughed. “You’re teasing me. I thought of you and how much I was hoping you’d call me when I got back home. And now you have!”

“What are you doing tomorrow?”

“I have to buy some food, but other than that I’m free.”

“I have to spend a couple of hours at the alley. How about you shop in the morning, and I’ll come pick you up at noon. We’ll have lunch and we’ll visit the alley for a couple of hours. How does that sound?”

“Like a lot of fun. I can hardly wait to see you again!”

After they said good night and hung up, Greg lay in bed smiling as wave after wave of euphoria ran through him. His life was never going to be the same again.

***

The next day at slightly past noon, Jill knocked on the door of Greg’s apartment. He lived in a converted attic in a modest brick home. Below him were two other apartments and his had a separate entrance up a back set of steps.

“How cute this place is,” Jill said, as she entered, “and how cute is the occupant!” Jill smiled at Greg and looked around at the furnishings. Greg looked upon Jill as if she were a mirage in the desert.

Jill came up to Greg and embraced him. “So nice to see you again!”

Greg held her and rejoiced that his worrying about her feelings toward him had been for naught. “You’re so beautiful, Jill!” She was wearing pants and a shirt. He noticed some embroidery on her shirt over her left breast and read, “Westside Alleys.” Next to the words was a picture of bowling pins flying in different directions.

“This is my uniform!” Jill said. “Isn’t it spiffy? Before my trip to Toronto I was wearing skirts with my blouse. When I got back I decided that I’d had enough of that. I bought these nice slacks. This is the new me. I can’t thank you enough for your contribution!”

“What did I do?”

Jill laughed. “Besides lending me your clothes – which was exactly what I needed in my confrontation with Barry – you showed me that there are men with real feelings, sensitivity, and true appreciation for girls. The thought that there are men who are the antithesis of Barry and that I could fall in love with one of them, has made me so much happier than I ever was with Barry.”

Greg wondered if Jill meant that she could see herself falling in love with him or maybe she just meant someone like him. “I guess this is a mutual admiration society,” Greg said, “because it was your suitcase that allowed me to finally get to express feelings that I’ve had for so many years. Even more than that, it’s your acceptance of me for who I am which has turned my life upside down. It allows me to see a future where I get to be myself and be as happy as anyone can be!”

“Nothing makes me happier than knowing I’ve had some role in making you feel happy!”

The embrace ended and Jill said, “This is the first I’ve seen you in pants.”

“Right, I guessed that I should dress like a boy today.”

“I understand. You do have some work ahead of you before you could present nicely as a girl. I’m pretty certain that you can one day achieve a feminine look that would only rarely raise suspicion.”

“You mean my makeup?”

“Sure. Makeup, hairstyle. Even some basic choices in clothing. I hope you’ll let me work with you on it. I’ll find it a lot of fun to make it our project. What do you think?”

“You’re so very kind.”

“Good. Are you wearing a bra and panties now?”

“Just panties. I haven’t put on a bra.”

“You should if you want to. No one will see it through that loose-fitting shirt you’re wearing.”

“It never occurred to me that I could do that. But sure, I would like to wear a bra if you don’t mind.”

“I don’t. I think it’s nice that you want to wear one. It reassures me that you’re the same Greg I met in Toronto.”

Greg laughed, “I’m still that guy!”

Greg fetched a bra from his bedroom and took off his shirt. He put on the bra with Jill watching and then put his shirt back on. “It’s a nice little secret we have,” Jill said. “Now I’m going to take you to a cute little lunch place I know of.”

***

Greg had been apprehensive about dining with Jill. They’d have to make conversation for an hour or more and that might reveal to her how boring he was. As soon as they sat down and ordered – they both were having quiche Lorraine – Jill asked Greg to talk about himself.

“Besides Venetian blinds?”

“Yes. What are your other passions?” Jill laughed, “Besides being pretty!”

“I have interest in history. Some weekends I’m a volunteer docent at the Chicago History Museum.”

“That’s interesting. Tell me about it.”

“There’s a lot there about the history of the clothing industry in Chicago. Dressmakers, milliners, retail stores and manufacturers. That’s been my area mostly.”

“What drew you to that?”

Greg blushed, “I hope you don’t think I have a one-track mind but they have dresses worn by first ladies, actresses and everyday people. I love to look at them and talk about them.”

Jill laughed, “And you’ve wanted to wear them?”

“Can you forgive me? Some of them are so pretty. They’re from different eras. I loved when ladies had all those petticoats on underneath.”

“And bustles?”

“Oh sure. And corsets! I’d love to show you the collection!”

“That would be so much fun.”

“There are also men wearing suits, if that’s what you prefer looking at!”

Jill laughed. “How did you know? I think I would like to buy myself a man’s suit. That would be cool.”

It was obvious to Greg that Jill and he were going in opposite directions as far as finding their preferential clothing.

“I think you’d be very handsome in a suit.” Greg said.

He thought he was being jocular but Jill said, “That’s nice to hear, Greg. I’ve been a bit worried that you might not like me dressing in a more masculine style.”

“Who am I to talk?”

“True.”

“The truth is you could dress anyway you want and I’ll still find you beautiful. There’s no reason for you to feel inhibited from being yourself. You taught me that.”

It turned out to Greg’s relief that the conversation flowed along between Jill and himself. They were curious people and while they had much to say, they were averse to being pedantic. The hour flew by, the quiche was exceptional and they topped it off with cappuccinos.

“Now I’ll show you my bowling alley. I’ll have a little business to take care of while I’m there. While I’m involved with that, I’ll get you set up in a lane where you can practice bowling. When I get a chance I’ll come over and help you. I should be done with my work in a couple of hours and then I’ll show you my place. Actually, I have a little present I bought for you waiting there. How does that sound?”

“Perfect. But you shouldn’t have gotten me a present!”

“I wanted to. I think you’ll be pleased.”

***

Greg had driven past the bowling center where Jill worked many times without really noticing it. It advertised thirty-six lanes and was one of the larger alleys in the region. Jill had a parking spot with her name on it. “This is incredible, Jill. You run this huge place!”

“It’s a nice place to work. Good people,” Jill said and Greg followed her into the building. They were greeted by the sound of bowling pins flying, bowling balls hitting the lanes, and a loud murmur of voices. Rock and roll came from speakers in the ceiling. Jill introduced Greg to a couple of women working behind a food counter, a man and woman bartender, and several other employees. Quite a few patrons greeted Jill with fist bumps when they walked past them. “Let’s get you some shoes.” They went to the main desk and a middle-aged man behind the counter said, “Hey boss.”

“Hey Jesse. This is my friend Greg.”

“Yo Greg,” Jesse said.

“Nice to meet you,” Greg said.

“Would you fix Greg up at lane thirty-six on the end? Thanks.” To Greg she said, “I’ll catch up with you in a little while and see what I can do to help your game. Bowl as much as you want. It’s on the house.”

“Thanks.” Jill left him with Jesse who got him shoes. Greg said, “I heard that Jill is a good bowler.”

“You’re telling me. She’s fantastic. Personally, I think she should turn pro. She’s that good.”

“I had no idea.”

“I haven’t seen you here before. How do you know Jill?”

“I’m a new friend of hers. I met her in Toronto.”

“Right. She told us about breaking up with Barry. The staff had been invited to their wedding. Too bad. They looked like the perfect couple. You never know about these things. It would have been a damn good party though.”

“You know Barry?

“We all know him. He’s a great bowler too. He dabbled in pro bowling, but was never quite good enough to make a living from it.”

“He bowls here?”

“Yeah. The Thursday night league.”

A group of kids came to the counter and Jesse said, “thirty-six is turned on. Have fun.”

“Thanks.”

Greg went to his lane and searched for a comfortable ball. Most of them were too heavy and he finally settled on a relatively light, green, and gold sparkly ball with finger holes that fit his hand. He confronted the lane in front of him and bowled his first ball. It went right into the gutter. He glanced around to see if anyone had noticed. Fortunately, everyone near him was preoccupied with their own bowling.

He bowled again and managed to knock down one pin. It was a start. He kept at it and by the time he was at the fifth frame he had accumulated twenty-five points. He was waiting for his ball when Jill showed up.

“How are you doing? What’s your score?”

“You don’t want to know. It’s embarrassing.”

The ball appeared and Jill said, “It’s darling that you chose a girl’s ball.”

“I did?”

“That’s ten pounds. I use a fourteen-pound ball. Most men use sixteen pounds.”

“I tried the others and they were too heavy for me.”

“That’s okay. Its best to use a ball you’re comfortable with.”

“I’m not embarrassing you?”

Jill laughed. “Hardly.” She looked at Greg’s score. “Twenty-five after 5 frames. At least you’ve got a lot of room for improvement!”

“I’m sure you’re right.”

“Let me see you bowl.”

Greg took the ball, held it up, and looked down the lane. He concentrated on doing the best he could do. He ran forward, swung his arm back and then forward and released the ball. It barely avoided the gutter and took down three pins.

“Oh God, Jill. I’m pathetic.”

“Stop that Greg! Like anything else, bowling requires practice and training which most people haven’t had. Anyone can throw a ball down the lane, but that doesn’t mean they know how to bowl. One thing I notice about you is that your body and movements are more closely associated with women than men. Your arms are feminine which explains your need for a light ball. Moreover, you don’t maneuver the bowling ball the way that men with arm muscles are able to. You can, however, adopt some techniques that I show girl bowlers that well compensate for the absence of large muscles.”

“I’d like to learn them to improve my game. I hope I’m not disappointing you.”

“How would you be disappointing me?”

“By not bowling enough like a man.”

Jill laughed. “I can see that you instinctively believe that any masculine traits you have should be attractive to me. You can let go of that idea. Trust me. Barry exuded masculinity from every pore of his body and I ultimately was very unhappy with him. We spoke of this in Toronto, but I’ll repeat myself. I find your feminine traits, such as your insecurity, to be quite endearing. More than anything else I want you to be yourself and to love yourself. I love that you have nothing in common with Barry. He’s ridiculously self-confident, even domineering, and I want nothing to do with that anymore. I’m captivated by the idea that I can use my strength to protect you. The greater the contrast between us, the more I feel a passion toward you.”

“I do think that you’re powerful! It’s even kind of overwhelming.”

“Your innocence around a bowling ball is adorable. I enjoy knowing that I can help improve your game. I love a challenge like that. When I start a new bowling class of young girls, I look them over one-by-one to identify the ones that will offer me the greatest challenge. Often they’re the most feminine girls. I can’t deny that you have a lot in common with them. I find that similarity to be alluring.”

“Okay. You’re right. It’s time I accept myself and accept your feelings about myself.”

“I’m glad you feel that way. Trust. It’s all about trust, Greg.”

“Right.” Greg wanted to tell Jill that a large part of his problem was how beautiful and sexy she was. It made him feel that he was unworthy of her. He hoped in time that those feelings would go away. Certainly, he’d have to rein in his insecurity so it didn’t become tiresome for Jill.

“Now I’m going to teach you how to bowl.” She had Greg stand at the top of the lane. She gently moved his arms and shoulders, and guided his posture until she had him standing erect and in a proper stance to begin bowling. She showed him how to take four steps, swing his arm and release the ball. He imitated her movements. Then she discussed where to aim for and other basic considerations. “Now, I’ll sit down and watch you bowl!”

“Okay. I’m psyched!” he said. He set himself up the way she had showed him and bowled. Halfway down the lane the ball went into the gutter.

Jill laughed and explained to him what she saw he had done to cause the gutter ball. “Try again.”

This time the ball went straight down the center of the lane and gave him a 7-10 split. “Holy cow. Eight! I bowled an eight!”

“You’re so cute, Greg. Practice what I taught you and I’ll be back in a little while.”

Greg watched Jill head off toward her office at the far end of the bowling alley. Along the way she stopped to chat with customers and employees. He saw a group of guys sitting together drinking beer and she fist bumped them all. She seemed to know them well. Just before she got to the office Greg saw a handsome guy come up to her and she stopped to face him. Their conversation was animated and then they went into the office and the door closed. He wondered what that was about.

Greg returned to bowling. Every so often he looked to see if the guy had left Jill’s office. He finished out the game he had started and managed to get a seventy-two. He began a second game. He was almost done with it when the guy who had been talking to Jill joined up with a few guys at a lane in the middle of the bowling alley. The guy was tall and had a nice physique that fit in with the group of young men with whom he was bowling.

“How are we doing Greg?” he heard Jill ask him.

“Hi. Yeah, better, definitely better. I’ve got eighty-two with one more frame.”

“That’s great.” It was obvious that something had happened to change Jill’s mood. She looked unhappy like she had been in Toronto when she joined Greg in the elevator. “Finish up and we should go.”

“Of course.”

Jill seemed distracted. She didn’t comment as Greg bowled two more balls giving him eighty-nine.

He returned his shoes and Jesse said goodbye to the two of them and they went out to Jill’s car. Jill unlocked it and they got in. She sat behind the wheel staring straight ahead.

Greg said. “Is there anything I can do for you? Do you need to be alone? I can Uber home.”

“No, Greg. I want you to stay with me. Let’s go back to my place like we planned.”

“Sure, Jill.”

She started up the car and drove a few miles into a neighborhood of relatively small houses with spacious lawns on tree-lined streets. “What a beautiful neighborhood,” Greg said.

They turned up a number of small streets until Jill pulled the car into a driveway. Her house was charming with Victorian elements to the design. With the engine off Jill sat in the car and Greg waited. She said, “Barry came by.”

So the guy she was with was Barry. His first impulse was to worry that she’s decided to go back to him. “I thought he was in Toronto?”

“He flew back this morning to convince me to go ahead with our marriage. He’s going back tomorrow.”

Greg braced himself for Jill telling him that she had decided to forgive Barry. “He begged me. He says he made one little mistake and I should give him a second chance. I said that a man who had true feelings for me would never have wanted to cheat on me in the first place. He’d be heartsick at the thought of hurting me because he cared about me so much. If you loved your dog, would you ever hurt it and then ask for a second chance to prove that you won’t hurt it again?”

Greg wanted to say that he would never do anything to ever hurt Jill. Not in a million years. From what she said he still wasn’t sure what she wanted to do.

Jill opened the car door and got out. Greg followed her into the house. It was nicely furnished and comfortable. “What a lovely place,” Greg said.

“Thank you. Have a seat.” Jill sat on a sofa and Greg sat next to her. “I’m sorry that you have to be here during this nonsense.”

“I don’t think it’s nonsense. You were engaged after all. I’m not surprised that it’s finally sunk into Barry’s mind the enormity of what he’s lost. You are …” Greg stopped out of fear of saying something that would complicate their relationship.

“I’m what Greg? Tell me.”

“I was going to say some flattering things here. Then I thought it’s not the time or place for that.”

Jill smiled at Greg. “You are unfailingly considerate. I was looking forward to spending a marvelous day with you and Barry found a way to inject himself into our time together.”

“I hope we’ll have many marvelous days together.”

“You’re right. I told Barry that my mind was made up. In fact, I told him that I’ve thought deep and hard as to what kind of man I might want to marry one day and it’s not someone like him.”

“What did he do?”

“He understood me to mean that I didn’t want a man who cheats on me. But I meant more than that. I was obviously thinking of a man like you. You understand that don’t you? We’ve talked about it more than once.”

“Yes. And you know that I want to be that man.”

“Anyway I tried to be very clear to Barry that my reasons for not marrying him were due to some important growth on my part. I’ve gotten to know myself a lot better. So in the long run he and I would never have been happy. Our marriage would have eventually gone off the rails because we wouldn’t be the people we thought we were.”

“How did he respond?”

“He doesn’t seem capable of hearing what I’m saying. That’s a trait that I can no longer countenance in a mate. I tried to tell him that, but he couldn’t understand me. He’s always been kind of dense but this time he was unusually dense.”

Greg always hung on every word that Jill said, so it was hard for him to see how Barry was unable to focus on what she was saying. “What do you think is going to happen now?”

“I wouldn’t be surprised if he contacts me again, particularly because he sees himself being a great romantic for having impulsively traveled back to Chicago. It’s funny because I saw myself as the great romantic by surprising him in Toronto. Anyway none of this matters. I’m not going back again!”

Greg felt relieved. He hadn’t anticipated Barry being a factor anymore and he was glad that Jill had not wavered in the slightest.

“So Greg. I have a little present I want to give you!” Jill got up and went to another room and came back holding a gift-wrapped box. The paper was pink with flowers on it, and there was pink ribbon tied over it.

“What a pretty package!” Greg said.

“I knew you would like that. So open it!” Jill was excited.

Greg carefully slid off the ribbon and then undid the paper. Inside was a fancy box with a lid that he opened up to reveal two perfect looking silicone breasts with nipples. “Oh my God, Jill,” Greg stammered. She had said that he should get them, but that she made it a reality was mind blowing. “I love these so much! They’re so beautiful! I can wear these in my bra? Can I wear them now?”

Jill giggled with delight. “Yes. By all means. They’re D cup so they should fit! Take off your shirt. We’ll find you a blouse to wear.”

Greg stripped to the bra he was wearing and took each breast one-by-one and inserted them into the bra cups. They fit as well as any real D cup breast would have fit. A geyser of joy sprung up in Greg’s heart and mind. “Oh, my dear Jill. What can I say?” He stared down at his beautiful womanly chest. “It’s so perfectly feminine. It’s so much what I’ve longed for.” Greg became choked up and Jill put her arm around him.

“How did I ever get to be so lucky to meet a guy like you?” Jill was giddy with happiness.

“I’m the lucky one,” Greg said. A couple of stray tears rolled down his cheeks that he brushed aside.

“Come with me. I’ll find you a blouse and skirt to wear.”

Greg followed Jill to her upstairs bedroom. She opened up her closet where Greg could see many skirts and blouses hanging. “This is a pretty white blouse,” Jill said, and took it out of the closet. Then she went through the skirts and said, “and this is the perfect skirt.” It was light blue with pleats. Greg took off his pants and socks and put on the blouse and buttoned up the front. An intense feeling of contentment came over him as he secured the buttons over his large chest. He then stepped into the skirt, hooked the clasp, and zipped it up to his waist.

“You’re captivating!”

“Am I truly?”

“Your body has a natural inclination towards girls’ clothing. The skirt and blouse appear as feminine on you as they would on any girl. “

“I don’t know what to say. Well just that I’m really glad that you appreciate the way I look, because it makes me incredibly happy.”

“We have so much to look forward to, Greg. There are so many ways we can build on this foundation. In two weeks Bonnie’s makeup class is beginning a new session. I’ve already enrolled you in it.”

“Thank you. I can’t wait to start that. I had so much fun playing with your makeup but it will sure be great to actually know what I’m doing.”

“And you’ll end up being very pretty, I’m sure.”

Greg looked at Jill and his heart fluttered. Each minute this was getting better and better.

“I have a lovely garden in the back where we can sit and have some coffee. I make great lattes. Would that be too much caffeine for you?”

Greg laughed. “Not at all. It sounds great.”

Jill made the coffees and they sat facing each other in two chaise lounges. ‘This is nice,” Jill said. “I have a bird’s eye view of how cute you look in the skirt and blouse.”

“I don’t know if I’m pretty or not, but when you say these things it makes me feel pretty. That’s such a good feeling.”

Jill laughed. “There’s a lot of girl in you Greg. You respond to many things the way girls do.”

“You’re making me blush. But I can say the same kind of things about you. You have an ability to take charge of things and make decisions in a masculine way. I know I’ve never been like that. It’s really nice to be with someone who is.”

They sipped their lattes and enjoyed a quiet moment thinking about how nice it was that they were both content with each other. After a while Jill said, “As you saw I have many blouses, skirts, and dresses. Many more than I’ll ever want to wear again. Same thing with my underclothing. At the same time I wonder about your clothes. I wonder if we should think of swapping at least some significant part of our wardrobe. We can also buy new clothing, but it would be a shame to have so much nice clothing sitting in our closets and not getting used.”

“Doesn’t your suggestion mean that I should commit to living my life, or at least a big part of my life, wearing girls’ clothes?”

“I suppose it does. You’re right. That’s the eight-hundred-pound gorilla in the room.”

“I would love to do that not just for myself, but as a tangible expression of my fondness for you – assuming that’s the way you prefer me to be dressed.”

“Once again you take sweetness to a whole new level. As long as this is something you would like to do, then I do hope that you’ll be able to make this transition in your appearance.”

“Then it’s all agreed. After I finish my makeup classes, then I hope that I’ll be ready to give up wearing my boy clothes. I guess I’ll take the plunge!” It occurred to Greg that he’d be seen by people who didn’t know him and those that did. The latter could cause some complications. Number one on the list were his parents. There was also his brother and sister. It would also not be an exaggeration to say that his guy friends and the people at the Venetian blinds shop will freak out. All these people would probably have quite a major reaction to seeing him wearing a dress.

While Greg was reflecting on what he might say to his parents, suddenly Barry appeared in the backyard. “What are you doing here?” Jill exclaimed angrily.

“No one answered the doorbell and I knew you were home. Your car is parked out front.”

Barry noticed Greg. “Who’s this … what in the world? Who’s he? Why is he wearing a skirt? That’s one of your favorite skirts. And he has tits. What the fuck? Have you gone crazy Jill?”

“You don’t listen very well, Barry. I told you we’re done. Nothing you do or say will ever change my mind. As for your questions which you have no right to ask, it’s none of your business who I have visiting me.”

“But Jilly. You and I have sat back here a million times! I proposed to you back here. You said you loved me back here. Doesn’t that mean anything to you?”

“The only reason you’re here is because you see me as a trophy wife. Pretty, sexy, shapely, and smart. You’re not here because I fulfill an emotional need for you or because you understand me, or because our personalities are tuned to each other. You made that abundantly clear in Toronto. As I said earlier, I’ve changed. I’ve grown up so that I see that our marriage would never have worked out, even if it started well.”

“You don’t understand. My mom and dad are so pissed at me. They want to kill me. They said I shouldn’t take no for an answer.”

“Barry. Your mom and dad view us as if we’re in a movie. Fifty years ago women might have been flattered by men who wouldn’t take no for an answer, but today that thinking is sexist. If you think our relationship is like a Hallmark movie where the couple always get into a fight with twenty minutes left in the movie, and resolve the issue with two minutes left, you’re wrong again.”

Barry sat down on a nearby chair and put his head in his hands. He made sounds as if he were crying. “So this is the end of the line?”

“I’m afraid so,” Jill said gently.

“You haven’t told me who this guy is.” Barry said, looking up at me. Jill didn’t answer and he said, “I saw you helping him bowl.”

“What’s your name?” Barry said to me.

Jill cut in, “Enough, Barry. Time to leave.”

“What’s your name?” Barry said ignoring Jill.

“Greg,” Greg said.

“What’s with the costume?” Barry said. He got up and towered over Greg. He was clearly much stronger and was powerfully built. “Answer me you little twerp.”

“Okay, Barry. Get out of my yard,” Jill said.

Barry lunged toward the front of Greg’s blouse as if to grab it. “What’s in there, pervert?”

Jill jumped up and forced herself between Barry and Greg. “Leave him alone!”

“Is this your lover now? A guy in a skirt?”

“Get lost!”

“He needs a girl to defend himself!”

“I’m going to call the police,” Jill said.

Barry laughed. “Yeah, right.”

“You’ve just displayed all the reasons why I would never marry you. It’s consistent with an engaged man having random sex before his wedding.”

Barry looked like he was debating whether to push Jill aside and go after Greg. Then he stepped away. “This isn’t over yet. There’s no way you’re dumping me for this creep.”

“It seems like you’ve forgotten that you’re the one who caused all of this. I rushed to Toronto because I loved you and see how I was rewarded? Anyway, you did me a big favor by revealing your true self to me. If you persist in meddling in my life with Greg then I’m going to ban you from the bowling alley.”

“You can’t do that.”

“Just try me. If you threaten Greg in any way then I’ll do it. I suggest that you apply your charm to wooing some other woman. You and I are over.”

Barry scowled at Jill and then turned away and left the way he had come. “Come here, Greg,” Jill said as she sat down again on her chaise lounge. Greg lay down on his side next to her and rested his head on her bosom. Jill put her arm over his shoulders and squeezed him. He felt his own breasts pushing into her side. “My poor Greg,” Jill said. “I feel terrible that you had to experience that. I’m so lucky that I discovered what a jerk Barry is before I married him! The big question is why I was so blind to his atrocious behavior.”

“I love how you defended me.”

Jill laughed. “I really enjoyed protecting you from Barry. I don’t know if I should admit it or not, but I even felt a little jolt of sexual pleasure during the encounter.”

“For Barry?” Greg said, worried.

“No, not at all. It came from taking on a masculine role.”

Greg squeezed Jill. He had never said it to her, but he definitely derived deep sexual contentment and pleasure from acting the part of a girl in Jill’s life. It had to be a big part of the reason why he was driven toward it.

“You’re the yin to my yang,” Jill said. What greater bond between two people could there be than the one that she and Greg had stumbled into.

Greg smiled. He so wanted to be the receptive half to Jill’s active half, and now she had confirmed aloud what he had wished would be true. “I love being your yin.”

Jill laughed, “I know you do.”

They lay like that awhile and Greg felt Jill running her fingers through his hair. “It’s nice that your hair is long,” Jill said. “I think a wavy cut with curtain bangs would be pretty, or perhaps a long brunette shag with subtle highlights.”

“I don’t know what those are, but they sound wonderful.”

“By the time you’re done with Bonnie’s course you’ll know the basics of hairstyling. She’ll work with you to figure out the most flattering feminine style that will fit your face and head.”

“And what about you?” Greg asked

“An inciteful question. What kind of hair do I want? I know I’d like it shorter, that’s for sure, but not very short. I don’t want hair that I have to brush every night like I do now. Kind of a mannish cut would most fit my desires. What do you think. If I had a boy’s haircut would you freak out?”

“Of course I wouldn’t,” Greg said and laughed. “I’d have to stop calling you beautiful and instead call you handsome!”

Jill laughed. “That gives me one of those little sexual jolts. I like the thought of being handsome!”

“You’re going to be my Gentleman Jack, or should I say Gentleman Jill!”

“And you’re my Anne Walker!”

Greg reveled in the thought of himself as Anne Walker. She was so pretty and he had been intensely jealous of the dresses she had worn on the show. As if reading Greg’s mind, Jill said, “I’m going to buy you one of her dresses one day.”

Greg’s heart skipped a beat thinking of what a glorious day that would be.

“By then you will have gotten a gorgeous suit to wear,” Greg said. “A Tiger of Sweden! Oh my goodness how sharp you’ll be! Can you take me to a cotillion?”

“Of course, I will. How could I hide such a gorgeous girl from the world? I’ll want everyone to see how pretty you are!”

They both laughed at the silly fantasy that they had made together. Still, Greg hoped it would one day happen. It would be a miracle but why not? Jill thought of what she would look like in a well-tailored man’s suit. She imagined the luxurious fabric, the styling. She would have to find a men’s shop. Greg could go with her and help her. It would be such a fun day.

“Greg?”

“Yes, Jill?”

“I want to go to a men’s shop and buy a Tiger suit. Would you come with me?”

“Of course! Wow. That would be so cool. They’re expensive.”

“I think it will be worth it. So let’s go soon.”

After a minute Greg said, “I didn’t know that the skirt I’m wearing is one of your favorites. That’s what Barry said.”

“It is. I’ve always liked wearing that skirt.”

“And now I get to wear it. That’s so kind of you.”

“I thought you’d be pretty in the skirt and I was right.”

***

The skies darkened and a thunderstorm came rolling by. Greg and Jill went inside and sat on the sofa. Jill put her arm across Greg’s back and said, “I was thinking about the little kiss goodbye we had in Toronto. Do you remember it?”

“Remember it?” Greg exclaimed. “Boy do I ever. It thrilled me!”

“I liked it also,” Jill said and laughed. “In fact, I was thinking that it might be fun to kiss again. What do you think?”

“Oh, Jill!” Greg said. Her words were stirring him up to a frenzy.

Jill tenderly moved her mouth in over his until their lips met. She applied just enough pressure so Greg would feel her kiss. Then Greg sensed Jill shifting her position angling more towards him. Her hand came up slowly to lay on this cheek and she turned his mouth to fit against hers and she pulled him in tightly and gave him a powerful kiss. Greg’s eyes closed and his head reeled with the excitement and pleasure of being so intimate with Jill. He felt his heart burning now with what had to be love for her. There was no other way to describe the sensation. After a minute or two Jill broke off the kiss and rested her cheek next to Greg’s. “That was nice,” Jill whispered in Greg’s ear. Before he could answer, she was kissing him again. This time he felt her tongue push gently into his mouth and his own tongue greeted hers. The tongue kissing dialed up their passion and Greg lost all track of time and even forgot where he was.

After a half-hour of kissing and just when Greg was wondering if Jill would mind him exploring other parts of her body, the phone rang. Jill stopped the kiss and listened as a message was being left. It was her brother. His twenty-year old cat had died and he wondered if she could come by and be with him. Jill picked up the receiver and spoke to him directly. After a short conversation she hung up. “I’ve had such a marvelous time with you, but I have to go to my brother. It isn’t just any cat. It’s a long story, but he’s very attached to it. He needs a shoulder to cry on.”

“I understand.”

“It’s a two-hour drive and I’ll probably spend the night. You’re disappointed, aren’t you.”

“Of course I am, but I also want you to do the right thing.”

“You’re a good person, Greg. I’m so happy that we’ve met. Depending on when I get back tomorrow I’ll call you.”

They got ready for Jill to drive Greg home when she said, “I almost forgot. Come with me!” Greg followed her to her bedroom where she opened her closet door. “I’ll pick out some dresses and other clothing for you to wear.” She went through the clothing taking out a few dresses, some skirts, and tops. Then she went into her dresser and took out many panties, slips, garter belts, and stockings. “I do have a couple of panty girdles and open bottom girdles that I’ll bet you’ll really like.” She fetched them and then put the whole collection of clothing into a large plastic bag.

“I’ll give you some of my clothes when we get to my place,” Greg said.

“Thanks!”

When they got to Greg’s apartment, Greg said, “What would you like? Certainly, my underwear.”

“Yes, I could use some more boxers.”

“You can have all of my boxers. I only wear panties now. Well maybe I should keep one pair in case I need it.”

Jill emptied out the bag of her clothes onto Greg’s bed and then put his boxers into the empty bag. Greg went to a closet, selected a suit, and took it out to show Jill. “Would you like a suit? At least until you can get your own, you might like wearing it. Also some nice shirts, undershirts, socks, and ties?”

“Wonderful,” Jill said. “It’ll be fun to wear your suit.” She laughed and added, “I don’t even know how to tie a tie!”

Greg walked Jill back to her car and they kissed goodbye. He watched as she drove off.

***

The magic of his time with Jill lingered in Greg for the rest of the afternoon and into the night. He reverentially hung up her dresses, skirts, and blouses in his closet. Her underclothes got his attention one-by-one. He admired each panty she had given him as well as the girdles and slips. Each article of Jill’s clothing held a bit of her essence which made them sacred to him. He kept on the blouse and skirt that he had been wearing until it was time for bed.

He put on his nightie over his bra and panty. Now, for the first time he was wearing the sexy baby doll with the D cup breasts in his bra. His image in the mirror was impossibly sexy. He felt he had the body of a girl. He got into bed and under the covers. He thought about how much he was falling in love with Jill. He felt as fragile as a glass sculpture of a ballet dancer he had once seen. The figure had the thinnest and most graceful arms and legs and looked as if the slightest movement would cause it to break. Greg knew that he had passed the point of no return in his feelings for Jill. If she were to dump him now, or perhaps, announce that she had a new boyfriend, he would suffer intolerable emotional pain. He shivered in fear at the thought. But he couldn’t air his insecurity to Jill because he knew that she would tell him not to worry. But still, until such time as they made a commitment to each other, he could not sleep entirely free of worries.

End of Part 2