The Suitcase

By

Pamela

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While Greg was waiting in line to check in to his flight to Toronto he noticed an extraordinarily beautiful woman checking into the first-class passenger counter to his right. Wouldn’t it be nice to be in first class. He wouldn’t have to be waiting in this line and perhaps he’d end up sitting next to that woman. Not that he would ever talk to her, but perhaps she would talk to him. Initiate a conversation. He watched her as she walked away heading to the security check. Who was ever upstairs in heaven had outdone themselves in creating such a gorgeous, shapely body. Congratulations. Wow.

***

The two-hour flight was uneventful. Waiting to collect his suitcase at the carousel Greg noticed that the woman he had seen checking in was adjacent to where the bags came out. There were a half-dozen people between himself and her. After a light began to flash and a loud buzzer sounded the carousel came to life and the bags started coming up a ramp and then sliding down to where they could be picked up. A few minutes later he saw his suitcase appear. It was a distinctive tan color of an uncommon brand. As a precaution he had put a piece of white tape at an angle near a corner of the suitcase. He spotted the tape.

The next instant he saw what appeared to be the identical suitcase show up on the carousel. The two suitcases landed next to and partially on top of each other. To his surprise, Greg saw the mystery woman check the tag of one of the tan suitcases, and then check the second one. Imagine that. He and the woman had exactly the same suitcase! He saw her yank the second of the two tan suitcases off the belt and work her way out toward the terminal exit. Greg slowly moved through the crowd of people and took the remaining tan suitcase that was his.

Greg walked out of the terminal and found a cab that took him to his hotel. He would be in Toronto for a week-long convention of the Venetian blinds industry. Not exactly a glamorous group, but a lot of nice people that Greg enjoyed meeting and greeting every couple of years. When Greg entered his hotel room he moved to put his suitcase up on the suitcase rack when he noticed that the tape was missing. Damn, he thought. It fell off every so often. He’d have to get better tape next time.

Dinner was in a couple of hours. He would be meeting up with his friend Randy for dinner. That’s what they usually did when they got to a meeting. First order of business was to take a shower and refresh himself after the airplane flight. He went into the bathroom, turned on the shower and cleaned himself up. After drying himself off he went to the suitcase to get clean clothes. He opened it up expecting to take out underwear when he recoiled in surprise. “Jesus Christ,” he exclaimed, “this isn’t my suitcase!” In fact, it was filled with women’s clothing. Whoever had packed the suitcase was a perfectionist. It was extraordinarily neat. Everything in it was folded perfectly.

Greg wondered how he could have possibly taken the wrong bag at the airport? First of all, he had seen his suitcase with the very distinctive tape marking arrive on the carousel. He had seen the woman check one tag and then the other of the two identical suitcases. She had to have purposefully taken the wrong bag unless she was a complete moron. Greg looked at the tag attached to the handle of the suitcase and saw that it read “Jill Cappels, 2134 Lapaloopa Lane, Chicago, Illinois.”

How ridiculous. He went online and found a phone number for Jill Cappels in Chicago. No one answered and a recorded message said that Jill was on travel. Call back in a week.

Holy moly macaroni, Greg thought. She’s got his suitcase. Hopefully, she won’t go through his things. Luckily, his clothes were clean, so that wouldn’t be an embarrassment. Of course, if he didn’t like the idea of her going through his clothes, then he shouldn’t go through hers.

Yet, it was more complicated than that. His conservative parents raised him in a conservative town. Boys were boys and girls were girls. There was a great chasm between them. A boy could no more be a girl than fly around the room. A major part of what made girls ‘girls’ was their clothing. Sure there was biology, but that was mostly hidden. Yes, they have curves that boys don’t have and they often have long hair and girl faces and voices. But, at the end of the day, it was the clothing. Clothing that was nothing like that of boys. Dresses and skirts, and all the unbelievably fascinating clothes that girls wear underneath them. All these clothes being purposefully and specially created solely for the female bodies they rode upon. Girldom could not be separated from the clothes girls wore.

Greg felt apathy towards the boy world that he had grown up in. Perhaps if he had a girlfriend he might be a bit more inclined to caring about being a boy. But Greg grew up being unlucky in love. The attraction that some girls and women had toward him inevitably washed away the more they saw him, until he became invisible to them. It had to be because they found him dull. Boring! After all, in recent years when he told women that he worked in a Venetian blinds shop, they inevitably winced and screwed up their faces as if they had eaten a slice of lemon. No other careers caught his fancy. He loved his job. He found the work to be quite interesting. Venetian blinds controlled light and dark. That was ripe with poetical meaning and he never got tired of thinking about that.

The absence of a girlfriend or prospect of getting one, had the effect of elevating his desire for girls to the point where everything about them was supercharged. Since they were inseparable from their clothing, women and girls’ clothing captivated him like nothing else on the planet.

Yet, Greg had not acted on his desires. The problem was crossing the chasm. The world of girls was walled off from that of boys. He could peek in and know that’s where he wanted to be, but how to get there? He lacked the imagination or the courage or both and so he had drifted along knowing where he wanted to be and not knowing how to get there. Until Jill’s suitcase washed up on his shore.

Greg contemplated the open suitcase. He felt as attracted and excited by the clothing as any king or pirate felt looking at a treasure chest filled with gold and jewels. Best of all, where women would not date him or want him to hold them, the women’s clothing in front of him was his for the taking. The clothing would not protest. He could wear this clothing and for the first time in his life cross the crevice separating boys and girls. Yet, beautiful Jill deserved her privacy. It was simply wrong to touch her clothing! Greg closed the suitcase.

Thank goodness, he thought. He had successfully fended off his desire for her clothing. He was proud of himself. That put him in a good mood. Then he realized that the only clothes he had to wear were those he wore on the flight. Having showered, he would not want to put on his sweaty underclothing. Yuck. He needed clean underwear. He sat at the top of his bed and pondered how he could get some clean clothes.

Of course, the answer to his dilemma was staring him in the face. He knew it, but he didn’t want to know it. The mystery woman had a pile of clean panties sitting right there in the suitcase. He could borrow one of them, couldn’t he? After all, she was the one who foolishly and mistakenly took his suitcase! Of course, he could wear his pants without underwear, but that seemed like an unnecessary punishment on himself. What to do, what to do? Greg wondered.

He opened up the suitcase again. He should at least look at her panties. Maybe there’s one that is sort of bisexual. Greg carefully lifted up a neat pile of folded panties and took them out. He went through them one by one. His heart pounded in his chest. His mind filled with excitement as he touched and held each panty. Each one of the panties was prettier than the last one. All pinks and whites. Lace and cute bows and printed flowers. Each one was utterly feminine. Jill was a woman who loved girlie panties that was for sure. These were powerful, sacred vestments. They brought him to the doorstep of the world of girls. All he had to do was put one on and then he’d be sharing this experience with Jill. He would have worn her panty. The very same panty that she wore. He imagined her bush against the panty and then his own. Here was the very first opportunity in his life to feel the way girls feel. He’d know what it felt like to be wearing the prettiest possible panties.

He held up a particular panty to put on. He’ll now put one foot in it and then the other and he’ll pull it up to his waist. As his mind wavered back and forth not knowing if he actually would do it, he imagined his dad watching his struggle. He’d be saying to him, “That panty is for girls only, my son. Don’t go there it is a dangerous place for you. One step into that world and you’ll only fall further and further in. Only girls should go there. I beg you, Greg, don’t.”

Then he saw his mom. How many times had he wondered about her world? What was she wearing underneath her dresses and skirts? When he had been a baby had he actually gotten to suck on her tits? If he only could remember what that felt like. That was intimacy. But if he had once known his mom that way, wasn’t that admitting that he was once in her world? If he had been in her world wasn’t he entitled to wear a panty like she did?

It became clear to Greg as he teetered on the edge of wearing the panty that the fact that he was teetering meant that he wanted to wear it. Eventually he would end up doing so, so why go through hours of fighting against the inevitable? Once he put on the panty he’d be free of the inner turmoil. In the same way that someone must dive into ice-cold water by not stopping to think about it, he now had to put on the panty. Don’t think! Just do it. Greg shut off his mind and put one foot and then the other in the panty and pulled it up to his waist. Looking at the pretty fabric against the skin of his thighs Greg gasped with excitement. It was better than he had ever imagined. “Oh my God!” he exclaimed aloud. “I’ve so wanted this moment. It’s so right! It’s so feminine. It’s what Jill must feel when she sees herself wearing this panty!”

Greg thought about putting the remaining panties back into the suitcase and then decided that he ought to take a look at everything that Jill had packed. Maybe there would be a clue as to where she was staying in Toronto? Yeah right, he told himself. No. If he was honest with himself then he knew that he wanted to see what’s in her suitcase because he wanted to know what Jill wears. He wanted to get close to her. What better way to know a woman than to be intimately involved with her clothing? Already he was falling into Jill’s world. His dad had been right. His mom was beckoning him. There was no going back.

Folded neatly next to where the panties had been were Jill’s bras. Greg’s eyes lovingly stared at them. As much as he had fallen in love with her panties, her bras seemed otherworldly. Unlike panties, they had no parallel in a man’s world. A bra and everything about them was only the realm of women. No man should ever have business with them. Yet here he was. Bras that were every bit as pretty as the panties were within his grasp. Sitting primly in the suitcase the bras had no ability to stop him from looking at them. They couldn’t prevent him from wearing one! Greg felt faint. If he wore a bra then there would be nothing to prevent him from doing everything that women did. He would want to imitate everything about them. He would be fully on the other side. His dad would have lost a son and even if his mom welcomed him into the world of women, she would still feel guilty for having not stopped him from coming there.

Greg looked at his watch. He had a couple of hours before he had to meet Randy. He put the pile of panties on a corner of the bed and then sat down next to the suitcase and took out each bra one at a time. Many of them matched the panties. They were as feminine as bras could be. Once again he could not decide which one was the prettiest. Each one attracted him. He read the size and saw that the bras were 36D. Jill would have rather prominent breasts. He remembered the curves he had seen at the airport that morning. Yes, indeed, he could imagine that she had D cup breasts.

After arranging the bras next to the panties, Greg explored the rest of the suitcase. He found several packages of brand-new pantyhose and stockings. They appeared to be expensive. He found a sexy, pink, lace trimmed garter belt. Yes indeed Jill enjoyed her feminine side. He found a half-slip and a full slip. Then found several skirts that he hung up in the closet. There was no going back, he reasoned. Jill would one day find out that he went through her suitcase so he might as well just empty it out and take good care of the clothes. Jill had a couple of pretty blouses that he hung up and then three dresses. She had several pairs of heels. Two very cute and sexy nighties were neatly placed in the bottom of the suitcase. He found a small, empty, black purse and a cloth bag filled with makeup items. Lipstick, rouge, and many things he couldn’t identify. There was a package of tampons and one of large pads for nighttime.

Greg noticed that the bras and panties had a feminine scent. Was it perfume or from a sachet? There was a fainter odor on the blouses. How delightful it must be to wear perfume. There wasn’t much left in the suitcase when Greg saw an envelope addressed to Jill at her home. There was no return address. He opened it up and saw that it was a birthday card sent to Jill from someone named Barry Alper. Besides the printed greeting Barry had written:

Dear Jill:

Missing you terribly. Toronto is fun. Work is a drag but making progress. Just another couple of months and I’ll be back! You know how much I love you, my sweet. I hope you have the greatest birthday ever. I’m going to have a surprise for you when I get home!

Love and kisses, Barry.

It figures, Greg thought. A pretty woman like that would definitely have a boyfriend. She’s come to Toronto to visit him while he’s on a work assignment here. How cute is that. What will Barry make of his ditzy girlfriend showing up with a man’s luggage?

Greg saw that it was time to meet up with Randy. He put on the jeans and shirt he had worn on the airplane and headed out of the hotel. He hoped that Randy wouldn’t be too upset that he wasn’t well dressed. If there was one truth about his peers at the convention it was that they were sharp dressers. He knew that Randy would be wearing a nice suit, but he had no choice. Even worse would be the next day at the conference when he’d be poorly dressed compared to the crowd of well-dressed guys. Unfortunately, there was nothing he could do about it.

***

When Greg met up with Randy he apologized for how he was dressed. He had debated whether or not to tell Randy that his suitcase had been switched with a woman’s. It would be a delicious tale to tell, but since he was wearing Jill’s panties he might end up trapping himself into admitting that to Randy. Instead he told him that he was waiting for the airline to forward his lost suitcase. Being a good friend, Randy commiserated with Greg about how he’d feel out of place at the meeting. “Hopefully, you’ll get your clothes tonight,” Randy said.

“I sure hope so!”

After a pleasant meal together, they decided to go to a bar and have a nightcap. They sat down and ordered drinks. Greg happened to be sitting facing toward a window that overlooked the street. He was listening to Randy when he saw Jill outside the window of the bar looking in. He waited for Randy to finish his thought and said, “One second, I saw someone!” He ran outside and Jill had vanished. She wasn’t anywhere to be found. He rejoined Randy. “I’m sorry, I thought I recognized a woman that I know from back home. She’s actually very beautiful and I thought, what a great excuse to talk to her.”

“I was meaning to ask you if there’s anyone serious in your life,” Randy said.

“I’m afraid not. What about you?”

“I keep meeting women but they’re not thrilled with my career choice.”

“Don’t you know it. We’re just the …”

“Blind leading the blinds,” Randy filled in the punchline and the two men laughed. It was the kind of humor that would fill the week at the convention.

***

As Greg headed back to his hotel, he scanned the streets looking for Jill. She was obviously staying in this neighborhood. He would have thought that she was with Barry. Why be alone? Perhaps Barry had to work late. He wondered why she looked into the bar. Was she looking for Barry or a place to get a drink? It was all mysterious.

Back in his room, Greg put Jill’s clothing into the dresser drawers and the empty suitcase into the closet. He took off his suit and climbed into bed wearing just the panties. He figured he should take them off but decided it was too nice wearing them. He ought to enjoy them a bit. He flipped through the TV stations and his mind thought of the bras sitting in the drawer near him. Maybe the time had come where he ought to wear one. He had the panty on, he knew which one of the bras matched the panty. He ought to at least take the bra out of the drawer. He decided that he’d just take it out, but definitely not wear it. He found the bra and got back into bed holding it in his hands. He thought of Jill wearing the bra. Imagine her breasts lying in the cups. The strap holding her back. Imagine if he could get to see that! Zowee!

Greg noticed that the station he was watching had five well-dressed women sitting around a table discussing a book about the modern woman. A couple of them were wearing white blouses and jackets that were open enough to see how prominent their breasts were. The other women were wearing dresses. Their hairdos were perfect as was their makeup. He watched their hand gestures as they talked and became fixated on their lipstick. If he put on the bra he’d be joining these women. He was already partway there with his panty. They no doubt were wearing panties and bras. So now he’d have a bra and panty like they did. His mind made some feeble attempts at saying no to himself as he put the bra on. He was amazed that it fit him. “I’ve got a thirty-six bandwidth just like Jill. Who knew!” He ran to the bathroom mirror to admire himself. Even though the D cup was empty Greg was excited in a way he had never been excited before. He stuffed two panties into each of his bra cups and went back to the mirror. The image of himself in the bra and panty, the feeling they had on his skin, and the acknowledgement that he had left his boy self behind to now share something exclusively with women catapulted him to a feeling of ecstasy. There was no going back! He wished he had someone with whom he could celebrate. Someone to appreciate his liberation from being male. He wished that would be Randy, but it definitely couldn’t be.

Greg decided to sleep in the bra and panty. Then he remembered the pretty nighties and he took out one of them and put it on. Oh my goodness, he thought. How unfair it was that he couldn’t have this pleasure of feeling pretty, of feeling soft and feminine, of feeling shapely all the time.

He lay in the bed and turned out the lights. It was only ten thirty and he realized that it was too early for him to fall asleep. He turned the light back on, took off the nightie and put on the garter belt. He took stockings out of their package and put them on. “I’m going to go to hell for doing this,” he said to himself. “Just wait until Jill finds out I put on her brand-new stockings and wore her underwear. He chose one of the dresses. It was a greenish-blue sheath dress, and put it on and zipped up the back. It came down to his knees and looking in the mirror he was convinced that it fit him well. It had to be the small amount of elastic in the fabric that allowed the dress to conform well to his body. He was especially captivated by the appearance of his having breasts. That he was wearing women’s underwear inside the dress gave him a strong sense of being a girl himself. His delight was compounded by imagining he had real breasts in his bra and a real vagina in his panties.

Greg’s hair was long and he did his best to give it a feminine styling. The last thing for now was the heels. He tried on a pair of black heels. They were open toe and accommodated his feet, even though they were a bit small. He fastened them and got up and paced around the room. He was bursting with excitement and felt femininity pouring out of each pore of his body. It was just after eleven at night and the hotel was quiet. Greg took the room key and stepped out into the hallway in his dress and heels. He quietly closed the door behind himself and minced down the hallway the way he imagined women walk. He held his hands the way a woman would. The danger of what he was doing seemed to magnify his excitement tenfold. It was as if he was declaring himself to be a woman in front of the world. He walked to the end of the hallway and turned around and walked back. He got the idea of walking past the elevator bank where at any second someone might appear. All the while he had never felt so overcome with happiness and excitement. He felt more alive than he remembered ever being. After another few minutes he walked back to his room and entered. His heart was beating a mile a minute as he sat on the bed and caught his breath. This was beyond exhilarating.

Greg took off the heels and lay on the bed. He turned out the lights. He felt for sure that he was now ready to fall asleep. In short order he was sleeping in the dress and underwear. In the middle of the night he awoke to pee and when he remembered how he was dressed he cried with happiness. In the dark he found the bathroom and lifted up his dress and peed like a girl. It was all too good to be true. On his way back to bed he thought that Jill would not be too happy about him sleeping in her dress.

***

The next morning Greg was reluctant to take off Jill’s clothing, but he had to get to the conference and register. The rest of his gang of friends would be there and he had to say “hey” to them. He, Randy, and a few others would go to lunch and catch up with each other. Apart from that were various sessions discussing the latest advances in blinds technology. Manufactures had exhibits that he wanted to see, as well.

Greg stripped down to the panties and put on his pants and shirt again. Just like he predicted, when he showed up at the convention he stood out wearing his wrinkled shirt and jeans. He spent the day telling everyone about his missing suitcase. Luckily, his friends were sympathetic and had their own stories to tell of lost luggage. Regardless, he’d have to buy a new suit as soon as possible. Another day or two in the same shirt would be horrific.

Throughout the day, Greg’s thoughts kept returning to Jill’s clothes. How much fun it was going to be that night after dinner when he finally could get dressed up again like he had been the night before. During lectures on Venetian blinds, Greg closed his eyes and relived his stroll down the hallway of the hotel. Tonight he’d do that again. Then, in a flash it occurred to him that he should put on some make-up and go down to the hotel bar and order a drink. Just the thought of doing that made him nearly swoon with excitement. There was a corner of the bar that wasn’t well lit. He could slide into a seat there and in the semi-shadows live out a fantasy of being a woman having a drink in a bar. My God that would be wonderful!

When the conference activities ended for the day, Greg walked back to his hotel to rest awhile before going back out to meet Randy and the others for dinner. When he was a few blocks from the hotel, in the distance he saw a woman stepping into a cab. He was sure that it was Jill. She was wearing black jeans and a blue-checkered shirt – exactly clothes he had packed in his suitcase. Could she be wearing his boxers? How strange that would be! Greg ran down the block yelling for Jill but it was too late. The cab sped off in a direction away from him. This was so bizarre. Was Jill staying in a nearby hotel? He assumed that she was off to see Barry. “So close yet so far.”

***

By ten o’clock Greg had returned to his room after dinner with his friends and was ready to get dressed again in Jill’s clothes. He washed up, shaved his face, and put on a different panty and bra set. Then he put on the garter belt and a new pair of gray stockings. They seemed to be quite exotic covered with small black dots and a seam up the back. Jill’s gray dress was probably the one that was to be worn with the stockings. He decided it would be fun to wear the full slip and he put it on. He stopped to admire himself in the mirror. He remembered seeing his mother in a slip every so often when he was growing up. Before putting on the dress he opened Jill’s make-up bag and applied rouge, mascara and whatever else he could find. He had no idea what he was doing but it was tremendous fun. When he had applied enough makeup to cover any trace of his male skin he stopped and then put on lipstick. That was even more fun than the makeup. He looked in the mirror and decided that he looked sort of like a girl. It would have to do.

Greg put on the same heels he had worn before. He put his wallet and key in Jill’s small purse and left his room. As previously, his excitement was nearly overwhelming. Oh, to be a woman, he thought. To walk through the world dressed like this and being a woman. This is who he was more than anything else he had ever been or thought of himself as being. Greg walked primly to the elevator and pressed the button. The world be damned he thought. He was only living once and this was an essential part of his one life. The elevator was unoccupied when it arrived. He rode it directly to the ground floor without stopping. Before the doors opened Greg fortified himself for any encounters he might have with people in the lobby. He stepped out of the elevator and saw that the lobby was deserted. He walked as gracefully as he could to the bar and was relieved to see that there was an empty seat in the dark corner. He sat down on a stool and waited for the bartender.

A minute later a young guy came up to Greg and said, “What’ll you have ma’am?”

Greg said, “Gin and tonic,” in a breathless voice that included a cough. He had aimed for a higher register than his normal voice and it seemed to have worked. The bartender gave no overt sign of finding Greg to be odd. A short while later he served the drink and Greg relaxed into the moment. Here he was wearing a pretty dress, stockings, and heels in a hotel bar. Legs crossed and inwardly feeling every nuance of his bra, panties, garter belt and stockings inside his dress and slip. Cascades of femininity rolled out of him, wave after wave. He wondered how he could ever go back to his former life. He was meant for this. He had been born on the wrong side of the chasm. Finally, God had sent him the suitcase in order to correct a great wrong!

***

An hour later, Greg settled with the bartender and got up to return to his room. While he was at the bar a couple of men had noticed him, but they hadn’t gone over to flirt. Greg was thankful for that. He had no idea how he would have dealt with a man who wanted to pick him up. Greg walked to the elevator, pushed the button, waited a minute until the elevator doors opened and he got in. He pushed the button for his floor and just when the doors were about to close, Jill ran into the elevator and stood next to him. She was definitely wearing his pants and shirt and seemed somewhat distraught. Her eyes seemed bloodshot as if she’d been crying. He turned slightly toward her and asked her what floor.

“Eight,” she said. “Thank you.”

Greg was on seven. In the tight confines of the elevator Greg was sure his game would be up – she would see that he was a man. As the elevator began to move the woman said, “It’s amazing but I had exactly the same dress as you.”

“Really?” Greg said in his ersatz feminine voice.

“Yeah. It was a favorite of mine. Dumb me, but I accidentally took the wrong suitcase at the airport yesterday and lost my dress and all my other clothes. I don’t know what came over me but I was ditzy!”

“Too bad,” Greg said. So it was an accident after all. “That would upset anyone.”

Greg could tell from his peripheral vision that the woman was looking at the dress. Then she said, “It’s crazy but you’re also wearing my favorite stockings. Weird, but I also own those heels! And the purse!”

“What a coincidence!” Greg said.

The woman stared at Greg. He could see that she definitely had been crying. “Did you just fly to Toronto yesterday?” she said.

Greg nodded.

“What city did you fly from?”

“Chicago!”

Greg watched her mind trying to come to grips with what was going on here. He couldn’t stand it any longer and said, “I’m sorry, I’m sorry, I’m sorry!” His voice was pleading and miserable.

Jill looked puzzled. “Sorry? Wait, is this my dress? My stockings and shoes?”

Greg nodded his head.

“You have my suitcase?”

Greg nodded his head again. “I’m sorry. You took mine at the airport.”

Jill looked at him confused. “I don’t understand. The suitcase I have is filled with boys clothes.”

The elevator arrived at Greg’s floor. “I’ll give you back your clothes,” Greg said. “They’re just down the hall here in my room.” Jill got off the elevator with him and followed him to his room.

“Wait!” Jill said after they entered. “You’re not a girl are you? That must explain it. You’re a guy and you got my suitcase full of girls’ clothes and are wearing them!”

“I’m really sorry, Jill.”

“How do you know my name?”

“The name tag?”

“Right. So why are you wearing my clothes?”

“You took my suitcase and I …,” Greg said.

“Yes, but is that a reason to wear my clothes?”

“But aren’t you wearing my clothes! I recognize my jeans and shirt.”

“True, but girls wear pants and shirts the same as boys. You’re wearing a dress, stockings, and heels. From the look of it, it seems that you’ve also got breasts of some sort. What have you got on under my dress?”

“Look, Jill, …” Greg started to say.

“Please take it off. I’d like to see.”

Jill unzipped the back of Greg’s dress and he pulled it up over his head.

“Oh my goodness. You’re wearing my slip! What’s on under that?”

Greg lifted the slip up over his head and off and Jill said, “Wow! My bra, panties, garter belt and stockings. I can understand the panties, at least in principle. I don’t see why you’re wearing a bra, stockings, garter belt, slip and dress. Are they helping you pretend to be a girl!”

“What can I say?” Greg said.

“The truth, maybe?”

“Okay. I saw you take one of the two identical suitcases and figured that the one that you left behind had to be mine. Only when I got to my room, taken a shower, and was looking for clean underwear, did I discover that the suitcase contained girls’ clothes. I must say that I’ve never seen such a neatly packed suitcase.”

“That doesn’t explain why you’re wearing my clothes.”

“Sorry. I needed fresh underwear so I borrowed one of your panties. Look, I feel terrible for this. I could see you were upset even sad when you entered the elevator and I don’t want to burden you with my strange behavior.”

“I am upset, for other reasons. But I want to understand this. I can see why you wore my panty, but what about the rest of it?”

“The thing is I find every one of your panties to be feminine and pretty. Just looking at them I sort of feel in love with them. So I picked one and put it on. Then later that night after I met my friend for dinner I was alone again and I was drawn to take a look at the rest of your clothes. Your bras were every bit as pretty as your panties. Well I realized that you have matching sets. I found the bra that goes with the panty I was wearing and I couldn’t stop myself from putting it on. It made me terribly happy. So happy, in fact, that I had no resistance to getting fully dressed in your clothes. Wearing your dress with the stockings, garter belt and underclothing made me happier than I can ever remember being. I guess I’m just a very, very sick person. These desires just boiled out of me!”

“Really? You haven’t had them before?”

“You’re right, I have. I’ve often thought about wearing women’s clothes but never did anything about it before your suitcase came.”

“This is a bit crazy to me. The fact that you love my clothes yet you’re a boy. Well, I guess I should say that you’re sort of like a girl as far as your personality is concerned. I mean it’s hard to say that you’re a boy considering how you feel. The way you looked in my dress was very much as if you were a girl. When I entered the elevator I was thinking that I’m with this nice woman who actually probably could use some advice about her makeup. I had only glanced at it, but I could see it was kind of funky.”

“I had no idea what I was doing.”

“It shows.”

“At least I haven’t worn most of your clothes.”

Jill seemed distant for a minute and then she said, “I was just thinking about how you get so much pleasure from these pretty clothes. I felt the same way when I bought them. I thought they were so perfect for me. I especially liked the idea that by wearing them I was making my boyfriend love me more and more. Boy did that turn out to be a dumb idea. I just seem to be making dumb decision after dumb decision. Taking your suitcase. Coming to Toronto! This trip has been so horrid!”

Jill was close to tearing up. Greg was relieved that she didn’t seem to be especially angry about him wearing her clothes. “I’m really sorry, Jill, but I read the nice letter from Barry. I was trying to figure out where you were staying in Toronto so I could give you back your suitcase.”

“Some nice letter!”

“I don’t understand.”

“I came here to surprise Barry. He’s my fiancé. I thought he would be in seventh heaven to have me with him. Instead, when I knocked on his door and he opened it, there was a girl in a negligee sipping wine and watching TV. There was no doubt that they were being intimate with each other. He had a boner in his boxers! Imagine that. Answering the doorbell with a boner in your boxers!”

“That’s terrible! So what happened?”

“I was so shocked that I ran away and then all I could think about was getting a drink. Getting a few drinks. What a colossal fool I am.” Jill began crying softly.

Greg wondered what he should say or do. “Last night I was at a bar a few blocks from the hotel with a friend and I saw you look in the window. I ran out to find you but you had gone.”

“I decided to drink at the hotel. I was a bit hungover this morning.”

Greg sat down on the bed next to Jill, still wearing her underclothes. She was sobbing and looked so miserable. He put his arm around her and she lay her head on his shoulder and wept. This beautiful woman seeking some human comfort that he was able to supply. He watched as her chest heaved up and down in his shirt. After a few minutes she held him a bit more tightly and then let go. “You’re very sweet for caring. You’re Greg, aren’t you?”

“Yes. It shouldn’t be a crime to be in love with someone. To write such a love letter and it be phony is terribly manipulative and unkind.”

“I’m glad to hear you say that.” Greg reached over to the side table and took a handful of tissues and handed them to Jill.

“Thank you.”

“At dinner time today I saw you get into a taxi.”

“Barry called me this morning and begged me to come to his place tonight. He claimed that the girl who was there with him doesn’t mean anything to him. She was just there for sex. He wanted to explain himself. So I went to his place by taxi. He cooked me a nice dinner. We sat. We talked.”

Greg still had his arm around Jill’s back. She was by far the most beautiful woman he had ever touched or been close to. To his great surprise it seemed natural. He fit in as Jill’s girlfriend dressed in her lingerie providing a sympathetic ear to Jill’s story of man trouble. “So now all is fixed up?”

Jill turned and looked Greg in the eye. “What do you mean? I told Barry he could eff himself and I never want to see him again!”

“He really did have it coming!” Greg felt strangely relieved that Jill was free of Barry. He knew himself well enough to know that he’d soon be wondering if she’d ever consider him to be her boyfriend. Then he laughed inwardly at the realization he was wearing a bra and her other clothing. A slight problem!

Jill continued looking at Greg. “I never met a guy who likes to dress like a girl. You’re the first one, Greg. The thing is that you’re a very sweet guy. There’s something about you that makes me feel relaxed. I can trust you. I’m sure of that. You’re honest and you don’t play games.”

“That so very kind of you,” Greg said. Her words had the effect of making him suddenly care what she thought about him. Would she want to get to know him? He had been worrying about having to return her clothes to her. That was bad enough, but now he was concerned that she meant more to him than just being the random stranger with whom he had exchanged luggage.

“You live in Chicago?” Jill asked.

“Yeah.” They compared where they lived and discovered it was only about a mile away from each other.

Jill stood up and said, “Can I use your bathroom?”

“Sure.”

As she walked to it, Greg asked, “Should I get your clothes?”

“One second,” Jill said, and entered the bathroom closing the door behind her.

Greg waited wondering what it meant that she didn’t just tell him to get her suitcase together.

He heard a flush and the sink ran and then she came back into the room. She was smiling. “Look Greg. The fact is that you love my pretty clothes. I can imagine that it would be hard for you to give them up and switch back to your boy clothes. Am I right?”

“Yeah, I’m afraid so. But I have no right to …”

“Let me finish. Tonight when I was with Barry and wearing your jeans and shirt I felt more empowered to seek what’s best for me than I ever felt before all dolled up in my pretty dresses. It was kind of a liberating experience for me. I felt so in control. I felt like I was finally going to get this right for me. I knew that I could never trust Barry again and I just couldn’t see having a relationship with someone I don’t trust. So what is it I’m saying?”

Greg felt some tears forming in his eyes. He wondered where it was coming from. All he could figure was that it had to do with the direction Jill’s train of thought was going.

Jill thought for a minute and said, “What I’m saying is that there will be no more men like Barry for me. I’m done with guys who see themselves as studs – as God’s gift to women. You’ve given me more emotional support than a thousand guys like Barry could ever have given me. That’s important. That’s real. That’s the stuff out of which happiness is made.” Jill looked closely at Greg’s face and said, “Are you crying?”

“It’s just … it’s just that you’re saying things that … that make me care about you. I want very badly for you to be happy.” He paused a second to regain his composure. “To be honest, I’m feeling terribly vulnerable. It’s not just about you knowing about my wanting to dress like a girl. It’s also about whether or not we could ever become friends.”

Jill but her arms around Greg and held him tightly. “You don’t have to feel vulnerable. I like the fact that you love my clothes. I’m also terribly flattered that you want to be my friend. In fact, I want to be your friend too. A friend of exactly who you are now. Well, I do want you to learn about make up!”

Greg laughed and wiped away his tears. “I guess we’ve both had a good cry.”

“Here I was thinking that this trip would cement my everlasting love for Barry and instead it opened up a whole new world for me. I like being self-confident and taking charge of my happiness. Being Barry’s pretty and sexy girl was not really me.”

Greg didn’t know what to say. If he had learned anything on this trip it was that the key to his happiness lay in pretending he was a pretty girl wearing sexy lingerie and dresses.

Jill laughed and continued, “My guess is that this trip has sort of had an opposite epiphany for you. Am I right? You’ve gotten to see firsthand how much you love dressing like a girl – well, pretending you’re a girl. Am I right?”

Greg nodded his head.

“You’re also thinking that that disqualifies you from becoming my boyfriend.”

Greg nodded his head. His tears were falling one by one down his cheeks. He took a tissue and dabbed at his eyes.

“I can’t say right now whether or not you’ll be my boyfriend, but I will say that I’m happy that we switched suitcases. I love wearing your clothes and you love wearing mine. Meeting you has opened up a world of happiness to me that I never saw coming. I want to see you back in Chicago and we’ll take our time and find out what this is. How’s that?”

A new volley of tears came from Greg’s eyes and he smiled. Jill leaned in and gave Greg the softest of kisses on his lips and pulled back. Greg looked deeply into her eyes and saw how kind they were.

Embracing each other, they sat on the bed deep in their thoughts until Jill said, “What do you have in your bra?”

“I put two of your panties in each cup.”

Jill laughed. “Not enough for D cups. We’ll have to get you some nice silicone breast forms.”

A few tears started down Greg’s cheeks. Jill used her fingers to wipe them away. “You’re precious, Greg.” She put a finger in her mouth and said, “Salty. Just like I thought.”

The End (Part One)