Leah Does Chicago

My friend Leah and I hadn’t seen each other in some time. I was very anxious to learn about her latest adventure so I thought I’d be early getting to the hotel bar where we had arranged to meet.

However, Leah beat me there and was already well in to her first cocktail and nicely chatting up the bartender by the time I slipped in.

“Hey girl,” she called across the room sounding as if it was her fourth cocktail, not her first, “this is Pierre. He makes the best Manhattans in town.” I love Leah. She has a natural effervescence that many of us need a bit of alcohol to achieve.

“Hi, Pierre,” I answered trying to get my voice in to a comfortable feminine pitch.

Leah

I settled in beside Leah. Pierre slipped a pre-ordered Manhattan in front of me. So much for my resolve to have a ginger ale only evening.

“So girl,” I demanded, “the last time we were together you were telling me that you were going to the Be All Week in Chicago. Tell me all about it.”

I had an ulterior motive in wanting to talk with Leah about the ‘Be All’. The Be All Conference, now in its 30^th year, is probably the premier transgender event each spring in North America. Five days full of seminars, vendors, social activities at the hotel and off-site are enough to leave even the most active girl exhausted but wanting more. I wanted to write an article about what the ‘average crossdresser’ could gain from attending such a conference. For sure there was the great amount of time one could spend in one’s femme identity and there was the chance to gain knowledge by attending seminars and seeing the products on sale up close rather than just over the Internet but perhaps Leah could provide me with the one ‘can’t say no reason’ to attend a large transgender conference.

“Oh it was so great,” said Leah, “you can’t imagine the fun I had.”

“I hear you flew en femme?”

“From the time I left home to the time I got back it was 100% Leah 100% of the time.”

“Awesome. I flew as Linda once but that was years ago before the days of heightened security. How did you pull it off? Were you nervous going through security?” I asked.

“I was not nervous, because in my mind I had rehearsed many possible scenarios, where everything had gone wrong and what I was going to do about it.

“What could be more intimidating for a crossdresser, than flying as a woman with your regular male ID’s. Last year I kept triggering the alarm because I forgot to remove my long bobbie pins that hold my wig in place, as a consequence I had to go through a pat down.

“This year, because of the “underwear bomber” scare, I figured that I should not wear my silicone breast pads, and I was proven correct.

“But how do they know that ID is yours when you are wearing a wig and makeup?”

“I spoke with a young female TSA employee, who proceeded to tell me that they check for eyebrow shape, eye color and nose and mouth shape. So no color contacts lenses please.”

“Seriously?”

Leah continued, “The interesting thing was that I had to go through the airport scanner. I was held until a female employee came and patted down my wig. I had some bobby pins holding my male ponytail and that was enough for them to require the need to check me out. So if you feel brave enough and want to try it; don’t wear any corsets, just put them in your carry on, and don’t wear falsies, just wear a padded bra.”

“No breast forms? No cleavage? I think I’d rather walk to Chicago.”

“This girl told me that they have “many of us” going in and out of airports, so they have gone through the drill and know how to deal with us appropriately.”

“So did you meet anyone interesting on the plane?”

“It was pretty quiet but things picked up once I got to Chicago.”

“How so?”

“My arrival was funny. My girlfriend called me from Chicago while I was waiting to get boarded, telling me about this great limousine service that she had taken very inexpensive. So while I was at Orlando Airport I called them to make my reservation, they ask for my credit card number that is under my male name, so when I arrived at O’Hare Airport the driver was looking for a guy. So with all the crap that I had with me I had to ask every driver if they were waiting for me.”

“ I can just see it,” I interjected, “you must have looked like a scene out of a Better Midler movie, wearing a tight skirt, in high heels dragging about seven pieces of luggage.”

Leah smiled. “When I got the right person he open his eyes and couldn’t believe it, besides he was also Spanish and knew very well about my name, being male. But he was very nice, he put all my suitcases in the truck and drove me to the hotel, I had a pleasant conversation with him on my way to the hotel and he actually gave his business card and offered to show me the town.”

“Which way did he mean that?” I asked but again Leah just smiled and winked.

She continued, “Checking into the hotel was a breeze. I have a “rat pack” of girlfriends that we meet once or twice a year at these events, we go out to eat, tease each other to death, and we have a great time. So after a quick freshen up I was off to meet up with them. The week was a whirl from then on.

“It’s funny but even though we exchange e-mails almost every day we still had a lot to talk about.”

“Lies about how good each of you looked?” I chided.

“Not lies,” she winked back.

“No, I’ve seen the photos. You girls are hot! I also looked at the Be All program. What a busy week! What were your highlights of the event?”

“My highlights? I had a photo shoot for the first time in my life in lingerie. That was an experience! I had been sort prudish with my female sexuality, and now that I have embraced it I find myself in a place that have never been before, sensual and full of life.

I got to dress well, to a point that one of my girlfriends told me: ‘you look so good that if I didn’t know you I would ask you if you want to get in bed with me.’ I took it as compliment, perhaps now when I am a dressed, my sensuality comes through and I look more desirable.”

“Maybe she didn’t know you as well as she thought,” I smiled.

“We went to avfew restaurants, among them a steak house, since I am tall and flamboyant a bunch of guys were looking at us, but I didn’t make eye contact with them. They were not going to come over our table since we were four of us. The funny thing was that when we got up to leave I walked by a group of women that were sitting nearby. They exclaimed in unison: ‘Oh My God!’ when they saw me. I laughed my heart out, them seeing a crossdresser in high heels and looking the part.”

I laughed with Leah but I changed the subject. “What about the seminars and vendors?” I continued, “Be All is loaded with interesting topics. When I looked at the program I thought it would take me three weeks rather than three days to attend all the seminars and talk to all the sellers that interested me.”

“I think they do that to keep people coming back. It’s like the Disney World of transgender conferences. You can’t see it all in one visit. I went to a few of the seminars, one’s I hadn’t seen before but the girls and I were really more interested in getting out and about in Chicago.”

“I know what you mean,” I said as I nodded to Pierre to bring our next round.

As the drinks were coming Leah added a bit of detail, “I have gone to several vocal voice feminization seminars, but I never practice and it takes time, some girls say at least six to eight months. One thing that I learned: I haven’t pay attention to how important is to have a feminine voice. Now I know it and I am working hard at it, not everything is good looks, the voice is so important to be accepted as girl in more ways than one.”

“Too right,” I purred softly, “now that you mention it you are sounding pretty sexy today. A lot of our sexiness comes from how we use our mouth.” I winked at Leah but the double entendre seemed lost on her.

She went right on, “I attended an interesting seminar about the “Attachment Psychological Theory of Transgenderism” and one by my friend Monica Prata about how to put together outfits, I was late. As I walk in she announced to everybody in the room ‘Hi Leah, you look great’ so everybody knew my name instantaneously and of course she called me to the front to explain my outfit! She is also a great makeup artist, I had my make-up done by her for the closing ceremony. It was worth it because I learned few tricks.”

“I know. I saw the photos from that Saturday night ball.”

As Pierre set the Manhattans in front of us I leaned to Leah and said, “Tell me about your ‘rat pack.’ How did you all get together?”

“Their names are Gina, Pee Dee and Rachel, I meet them at my first Southern Comfort Conference and we have been girlfriends since. We share common interests, we like to go out for dinners and look like ladies. We have never had a problem with the check; there is usually more money on the table that is needed to pay the bill. They are from LA, New York and New Jersey. What a combination!

“Gina actually introduced me to the other two girls; I met Gina on a bus ride in Atlanta. We started chatting, for some reason we liked each other right off the bat. From there it was like: same time same place next year! Only now we move it around a bit.

“We have only been at SCC and Be ALL but next year it will be Las Vegas! And of course we’ll all be at Southern Comfort in September.” Through the rest of our chat Leah would freely tell me stories about what her ‘girlfriends had said or done. To me it sounded a lot like my wife telling me about her sister’s new love life or her best friend’s new status as a grandmother.

I could feel the effect of the Manhattans. I was starting to get reflective. “You know when we accept out transgender nature and start to come out of the closet a lot of things change for us. On the negative side we often can’t share this life with our partner, family and friends of a lifetime. However, through local support groups and distant conferences we are able to build new relationships so important to the human psyche.”

“That’s right,” agreed Leah, “sometimes in our local group the girls are just changing their small closet for a slightly larger one. With friends I’ve met at Southern Comfort and Be All I’m truly able to be Leah, totally and fully Leah.”

I looked at my watch. It was coming near the time for our friends to arrive to go with us to dinner but I had one more question for Leah, “I hear it can be pretty tough saying good bye at these conferences?”

Leah laughed and nodded at the same time. I knew she had a funny story for me, “Gina did the nice thing of waking me up on Sunday morning. She had an early flight, very early. She wanted me to come downstairs and have breakfast with her and Pee Dee. I walked into the restaurant in my pajamas, half sleep, and rubbing my face, nice picture with toe and finger nails painted, no wig, just my long male hair. You can just imagine! I still can’t figure out how the waiter was able to keep a straight face seeing me looking like that.

“I guess when you feel comfortable with your friends you can wake them up that early. She will pay for that one.”

We laughed and sadly that is all I learned. Leah was nodding toward the lounge entrance and there stood our two friends.

Leah and I didn’t talk further about Be All but I have a feeling I’ll be trying to join them in Las Vegas next May.

As we rose to join our friends it occurred to me that Leah had given me the third and greatest reason for many to attend a transgender conference – the friends one meets can become your femme identity’s best friends that she was never able to find in high school or back home.

Tags: conference, featured

Category: Transgender Fun & Entertainment