An Unconventional Convention

An Unconventional Convention

A chance encounter for a crossdresser changes everything.

The airliner's wheels hadn't been on the runway for more than ten seconds when a hundred cell phones were out and airplane mode was switched off. When the plane finally came to a stop at the gate and the little bell went off, dozens of seatbelt buckles were flicked open and passengers stood up in the aisle to retrieve their bags from the overhead compartments... so they could wait for another ten minutes while the people ahead of them moved slowly off the aircraft.

Two men, who had sat across the aisle from one another but who had not spoken during the two-hour flight, struck up a conversation.

"So, what brings you to Springfield?" one asked the other. "This home for you or are you here on business?"

"Business," the man replied. "I'm here for a convention of graphic artists. I'm speaking to a group of advertisers tomorrow."

"Really?" The first man said. "I'm going to be at that lecture! What's your name? Mine's Casey, by the way."

"Rich," he replied and extended his hand. "I hope I don't put you to sleep."

"I'll have black coffee with breakfast," Casey joked. "Where are you staying? The Mayberry, where the convention is, I assume? Maybe we can split a cab?"

"Yes, but I'm not going right to the hotel," Rich answered. "Plus, I have a checked bag I need to get."

The two chatted on their way along the concourse, and then split up heading for baggage-claim and transportation, respectively. "Okay, well, maybe I'll see you in the hotel lounge, or something," Casey said as they parted.

After Rich pulled his suit-bag and a medium-size roller bag off the carousel, he headed for the rental car terminal. He stopped for some fast food after leaving the airport, and after checking in at a little after 7:00 in the evening, he went up to his room.

He unfolded and hung up his suit-bag, then took out the conservative grey suit and the white and blue shirts that went with it. Next he removed a black, above-the-knee-length skirt, and a white, slightly-transparent, button-front blouse. He looked them over for wrinkles--the skirt always traveled well, and there were none to speak of--but the blouse could use a pressing. That was not unusual, and he had called ahead to make sure there was an iron in the room.

He took off his clothes and he went into the bathroom to shower, which included shaving his legs. After he dried off, he gave his face a careful, close shave with a new razor, and then used the razor to remove what little hair was on his chest.

Out in the room, he paired his phone to a blue-tooth speaker he had brought, and started the playlist that he had named "smooth jazz." It contained a few dozen classics like As Time Goes By, The Nearness of You, Satin Doll, and They Can't Take That Away From Me, by artists like, Stacy Kent, Barry Manilow, Julie London, and Rod Stewart.

Naked, he took out the ironing board and iron and gave the blouse--which he had hung on its hanger on the back of the bathroom door to steam it--a quick once-over.

He then opened his wheeled bag and removed a pair of khaki pants and a couple of polo shirts from the top. Next, he took out a pair of red women's panties, trimmed with lace. He stepped into them, pulled them up, and tucked his penis and testicles in between his legs. There was a bit of padding in the crotch to conceal that tuck, and it was even sewn so that it produced a slight camel-toe in the front. He looked at himself in the full-length mirror, and turned around.

The thin silky fabric of the panties hugged his rounded ass--a biological gift from his mother--nicely. He slid his hand over his ass and let out a contented little hum. It felt good to be morphing again--as he called it. It had been a long time since he'd been able to take his crossdressing as far as he would this weekend, out of town and alone.

He went back to the bag and lifted out a box almost a foot square and six inches deep. He lifted the lid and looking up at him was a pair of very realistic-looking C-cup breasts, complete with half-dollar-size nipples with stiff little nubs.

Purchased from a theatrical supply company over the Internet, they were expensive as hell--nearly six-hundred dollars--but the way they made him feel when he wore them--and this would be only the third time--was worth every penny.

One at a time, he took them out and brushed a layer of spirit gum around the edges before positioning them onto his hairless chest. The silicone that they were made of tapered so thin at the edges that it was translucent and the color matched his own so well that once he added a little makeup they blended in so well that anything short of a long, direct stare would miss the fact that they were prosthetics.

Once the adhesive had set, he twisted back and forth to get his boobs to jiggle a bit. He loved the feeling of their realistic weight pulling on his chest. It also tested that they were well-attached.

Looking at how realistic his breasts looked and moved in the mirror, he cupped them, hefting their weight, and giving them a squeeze. He slid his fingers over the nipples and wondered if he should go braless tonight under the diaphanous blouse. As exciting as that thought was he decided against it. He had a brand new lace-trimmed shelf bra, so with eighty-percent of his breasts still uncovered he could enjoy the exposure and the sexy feel of the bra at the same time. Win, win!

He put on the bra and as he got it adjusted and comfortable he thought about how his wife complained about having to wear one. He was thrilled when he got to wear one; it made him feel sexy as hell!

After another admiring turn in the mirror, he took his makeup kit out of his bag and sat down with it at the desk. Using the magnifying mirror in the lid of the kit, it took him nearly a half an hour to get the foundation and rouge on, do his eyebrows, his eyes and lashes, and his lips.

Next, he brushed back his brown hair--with ever-increasing shoots of grey--and then pulled on a short-styled, highlighted, honey-colored wig. It was the second most expensive and newest item in his ensemble, and this was the first time he would be wearing it with full makeup and the breasts.

The transformation took a long time but it was astonishing. She now looked at least ten years younger, and could probably walk through a room full of friends without being recognized.

He went to the tall mirror and did another inspection turn. He would like to have taken some selfies, but what the hell would he do with them? He sure couldn't leave them on his phone to be accidentally discovered by his wife. They had a pretty good marriage by all conventional standards, but there was no way she would understand this.

He took a black garter belt--matching the bra--from his bag and put it on, getting it to sit low on his hips. Next, he rolled on a pair of tan stockings and clipped then into the straps. He loved the feel of new nylons against his freshly shaven legs.

He put the blouse on next, and standing in front of the mirror, he experimented with how many of the top buttons to leave undone. Four was probably a bit too exposed as the last one fastened was right at nipple level. Three allowed for a little cleavage exposure if he turned correctly. Two was conservative, but that made for an interesting disparity considering the blouse was slightly see-through and his mostly-naked breasts would be semi-visible. With only one button undone, his pearl necklace would be hidden, and buttoned all the way to the neck--with his evident tits and the black bra--it made him look like a slut-secretary in a porn movie... which was not an altogether bad look, just not what he was going for tonight. He decided on two, and put on the necklace.

Next, he stepped into his skirt, carefully tucked in the blouse, and zipped it up the back. He slipped on his two-inch-heel black pumps, stood up, and walked around a bit to get his feet settled in. He would have preferred to be wearing his four-inch stilettos, but those were just for around the house. He could walk well enough in them, just not for a long time.

His shoes were probably the most incongruous part of the whole outfit. They were huge compared to most women's shoes. On the other hand, he had bought them in the woman's department of the shoe store, so obviously, there were some women out there with feet his size.

He clipped on a pair of pearl earrings that matched the necklace, and then put on a pair of black-rimmed "secretary" glasses with plain, clear lenses.

Standing in front of the mirror, once again, he did a slow turn, checking out the finished transformation from all sides. He was pleased with the look, except for his hips; they were a little too straight. A pair of stick-on "hip enhancer" pads was going to be his next big-ticket purchase.

When he transferred some cash, a credit card, and his license to a small clutch purse, he stopped and looked at the photo on the license. He sure hoped to hell that he wouldn't need it to identify himself, tonight!

One last look in the mirror before he left the room caught something he had forgotten. He slipped off his men's wedding ring and put it into a pocket of his shaving kit.

Two young men--probably in their late-twenties--stood in the elevator when he got on. He smiled at them and they smiled back, then he turned and faced the door. Even if it had not been for the polished, mirror-like walls, Rich would have felt them checking him out. Pretending to look at the numbers above the doors, he could easily see in his peripheral vision that they were elbowing each other while staring at the reflection in the door of his black shelf-bra and the c-cup breasts it supported. The bright halogen overhead lights made the blouse almost transparent.

Damn, he felt sexy!

He drove a few miles to a shopping mall that he had passed on his way to the hotel. He was excited to walk around in public, catching people's glances at him and even feeling their fleeting stares. He didn't want to go to a bar or something where close scrutiny might reveal his secret. And he certainly wasn't looking to be picked up. Having sex was not what this was all about; it was about looking and feeling sexy.

He looked in the window of Victoria's Secret, but didn't go inside. The likelihood of fooling the salesgirls in there was pretty slim.

After about a half-hour of walking around and collecting mostly-admiring glances with a few disparaging looks from other women, he went to the food court, got himself an Orange Julius, and sat down at one of the hard-chair tables to give his feet a rest.

From the very edge of his vision he noticed a man at another table staring at him. He decided to get up, and give the guy a better look and a grin before leaving. Standing, he straightened his blouse, making sure that the stiff nipples of his supported breasts tented the light fabric. First he stood in profile to the man, and then turned to face him and give him a sexy smile. But the smile had barely parted his lips before it evaporated. He was looking directly into the eyes of the guy he had met on the plane!

He quickly broke eye contact, turned away, and started to walk off. But even as he turned, he saw the guy get up and start toward him. Shit!

"Hey, wait up!" the man--whose name he didn't remember--called out. "You forgot your purse."

Well, fuck! Now, he had to go back. But maybe the guy hadn't recognized him. It would certainly be a compliment to his transformation if he hadn't.

He turned back just as the man picked up the purse to hand it to him. "Oh, thank you!" he said in a damned good impersonation of a woman's voice while trying to avoid renewed eye contact.

"Hi, Rich," the man said as he extended the purse. "I'm Casey. We met on the plane."

Rich let out a resigned sigh, and in his own voice said simply, "Surprise."

"Very nicely done!" Casey said. "If the wig had been covering your ears, I'm not sure I'd have recognized you."

Rich blinked in surprise, first that the guy was not being confrontational and had not made some disparaging or snide comment, and then at what he had said. "My ears?" Rich repeated.

"I've been an artist since I was a kid," Casey explained. "In high school and college I used to work at the local mall doing caricatures, so I had to pick up on people's features pretty quickly. One time I read that ears were like fingerprints; no two people's were exactly alike. So, I started looking more closely at ears to see if it was true. It's become a habit with me now. And it is true, by the way."

"So, um, if I buy you dinner can I buy your silence?" Rich asked as he unconsciously touched his ear. "I'd rather not be outed back at the hotel. Some people might not take my talk quite so seriously, you know?"

Casey smirked, and replied, "Oh, I can be bought, but I just ate, and I think my silence is worth a lot more than just dinner." He overtly looked down at Rich's chest, and added, "Maybe we could make a trade."

Rich swallowed hard, not liking the direction this was taking.

But then Casey let him of the hook. "Let's go to the pub down at the end of the mall, you can buy me a drink, and tell me your story. When we leave my lips are sealed."

"My story?" Rich repeated.

Gesturing up and down Rich's body, Casey replied, "Oh, there has to be a story here! You took some time--and spent some money--to do this, and you did it well! Transsexual, transvestite, bi, cosplay, winning a bet, witness protection. Inquiring minds want to know."

Again, Rich just blinked, not sure quite how to respond.

Casey went on, "Along with being a graphic artist and a student of the human form, I'm an author and a student of human nature. Most of my stuff is murder mysteries, but I'm always looking to find unique characters to roll into my stories." He smiled, gestured toward Rich's barely-hidden fake boobs, and added, "This is about as unique as I've stumbled upon."

"You think I'd make a good murder victim, huh?"

"Oh, not the victim!" Casey replied. "What leapt to mind is a serial killer who doesn't give a damn about eye witnesses because the person witnesses see doesn't really exist. Maybe his kid sister was raped, so now he goes out in drag, and any guy who hits on him, he sticks an ice pick in his ear."

Rich blinked once more, and said, "Looking at me for a minute and a half made you think of that?"

Casey laughed, and answered, "Yeah, sorry. That's just the way my mind works. Always looking for the next plot." He then added, "So, what do you say, good-lookin'; buy a sailor a drink?"

Rich smiled, and said, "Sure. But I guarantee my real-life story won't be as interesting as anything you could make up." As they turned to leave the food court, Rich said, "I'm a crossdresser, by the way. I like the look and especially the feel of women's clothes."

"Rats," Casey said jokingly. "I was really hoping for the witness protection thing." As they walked, Casey asked, "So, does your wife know about your hobby?"

"How do you know I'm married?"

"I saw the ring on your finger on the airplane and noticed it's missing now."

"Hmm. Ears and rings. Is there anything else you observe on strangers?"

"Asses," Casey answered. "I was watching yours when you were ordering your Julius. Very nice. Is it real?"

Rich laughed, and said, "Yeah, that's all mine. And thank you, by the way. In answer to your question, no, my wife doesn't know I'm crossdresser."

He went on, "Our marriage is good. We have very few arguments and we have pretty regular sex. Gail can be sexually open at times, but not inventive. If we try anything new it's because I come up with it.

"We have anal sex--with a condom--on occasions like our anniversary or my birthday. On her birthday, though, her special treat is to have me rub her feet and then hold them tightly around my dick while I fucked them and blow my load all over and between her toes." He shrugged, and added, "I never got the fascination, but who the hell am I to judge, right? Hell, I'm happy to indulge her in any perverse thing she wants and only wish there were more."

Almost as if talking to a therapist, and in a reminiscing frame of mind, Rich went on as they walked, "I talked her into pegging me with one of her dildos, once, but she found it disgusting, and even threw the vibrator away, afterward."

"Were you crossdressing before you got married?" Casey asked.

"Yeah. Since my teens, actually," he replied. "One of the chores that my sister and I had to do was folding the laundry. I used to love the soft, smooth feel of her panties as I folded them--especially the ones with a little lace! Then, one day I was home alone and decided to try them on. It's hard to explain, but that delicate, silky feel of the nylon, or rayon, or whatever they were made of felt incredible against my skin--so much different than my cotton tighty-whities. It was kind of like a drug. Suddenly, all of my male hang-ups--being competitive; trying to be macho; wondering if I was ever going to get laid--disappeared and I just felt pretty and completely carefree. I think it's how I imagined girls must feel all the time. The other way it was like a drug is that from that moment on I was hooked."

"Did she ever discover you using her panties?" Casey asked.

"No, thank God!" he answered. "She's not exactly open-minded. She'd have told our folks and I probably would have been committed to some home for the perverted and weird. No, I started buying my own--which fit better, anyway. I also bought myself a bra; I couldn't get my sister's to fit at all."

"When I moved out and got my own place, I would wear my women's underwear around the apartment quite frequently. Then, I began going out in public with the lingerie under my men's clothes. Eventually, I bought a dress at a thrift store and wore that around the apartment over the panties and bra. When I finally bought a wig and some makeup I began going out in public, although not where anyone would know me. God, that made me feel good! So free and alive!"

"So, apparently, your sister's panties were just a gateway drug to the hard stuff," Casey commented.

Rich laughed and said, "Apparently so. I hadn't thought of it like that." He glanced at Casey for a moment, surprised--and appreciative--of how easy it was to talk to him about all this. He'd never had a conversation like this with anyone. It was very cathartic.

"So, fast-forward to your marriage," Casey said. "Have you ever tried on your wife's under-things?"

"Once. On our honeymoon in the Bahamas," he replied. "I decided to test the waters of her kinkiness, and I wedged myself into her panties and bra after we'd just had an energetic romp in the king-size bed. Stepping out of the bathroom, I struck a pose, and asked in a joking tone, 'So, what do you think of the new me?' "

He went on, "The jackpot would have been that she would be aroused--the sight maybe fanning a repressed ember of bisexual curiosity, perhaps. But I hoped that she would at least be tolerantly amused and willing to talk about and indulge my little fantasy. I couldn't have been more wrong. 'Well, that's fucking sick!' she snapped at me. 'Take my underwear off before you ruin them!'

"And so, my fetish remained locked in the closet, only coming out when I was home alone for some extended period, or when I traveled alone on business, like this weekend."

"You must have a pretty secure closet to keep all that hidden away," Casey said gesturing up and down Rich's body with the wig, prosthetic breasts, shelf-bra, blouse, skirt, nylons, and shoes. He was guessing that there was probably a garter under the skirt, too.