The Next Adventure . . . Is Right Around the Corner

Do you ever get the feeling that you have seen it all, done it all and there is nothing new to experience?

A friend was feeling that recently. She says the feeling ‘sucks’!

We were sitting together, two old ‘queens’ at the end of a bar waiting for the early action to get started.

Sometimes I’m with her with that ‘done it all’ feeling. It does suck. That is why it is great to have new experiences and adventures to anticipate. Even at our advancing ages, she says, it is great to look forward to new experiences. “That’s why we have bucket lists,” she exclaimed as she prepared to tell me how she ‘broke her funk’. “People go on Caribbean cruises, Alaskan cruises, European river cruises or even Antarctic cruises seeking out new adventures to check off their bucket list. For others it’s Machu Pichu, Kilimanjaro, or Nepal.”

“I once heard of a guy telling his new trophy bride they were going to Nepal and she was all excited,” I interjected. “Then when the time for the trip came, she pouted, ‘Nepal! I thought you said we were going to the mall!”

“Yah, right,” my friend groaned. “Well, my funk-breaking trip was nothing like that or any of those adventures but my recent trans trip to Florida convinced me that perhaps I had not seen and done it all.”

I had the feeling I was going to hear all about it and so are you (if you read on).

“Tell me more. Tell me more,” I sang.

“My first stop was Lakeland, a good-sized city between Orlando and Tampa.”

“Home of the Detroit Tigers spring training,” I interjected again.

“Not only that but I learned it is home to Florida’s first and oldest gay bar,” added my friend. She continued, “you must have heard of the Pulse Nightclub.”

“Yes, of course,” I said as we were both referring to the horrific shooting at a once popular gay club in Orlando.

“Well Lakeland had the original Pulse but after the shooting and out of respect they changed the name of the Lakeland club to the Parrot, the Parrot on Main Street. That’s where I went,” she continued, “And let me tell you that in that part of town Main Street is anything but a main street. It is full of used car lots, small warehouses, churches and this one gay bar.”

ADVENTURE #1

“I assume the gay bar had a drag show or otherwise you would not be going there?” I asked.

“Yes, but to save the $5 cover I got there before nine and the show was not to start before midnight.”

“That’s a lot of shooters!” I exclaimed, referring to a pastime I knew she liked.

“True but I was driving and teetotaling that night. I did not need to be pulled over for a DUI in a strange city.”

“So how did you amuse yourself?” I felt there had to be a story somewhere.

“I positioned myself with my Coca-Cola at a high table and stool. Anyone coming to the bar would look over to me and see my gorgeous legs, crossed sexily and my face smiling over at them. It wasn’t long before I made eye contact with a nice-looking man. I smiled. He smiled. I gestured and he brought his drink over and ordered me another coke.”

“You ARE a fast worker,” I exclaimed.

“Not so fast,” she replied, “we talked for a while about where he was from, what he did for a living and why I was in Lakeland. He was easy to talk with. And did I mention he was not hard on the eyes?”

“No but I know you well enough to know what type of person you would make eye contact with,” I retorted. “How long was it before you got him into bed?”

“It didn’t happen. But what did happen knocked me over. It turns out the guy was a long-time crossdresser who was out that night in drab. And I mean a go-all-the-way CD, not one just slapping on a bit of lingerie. He showed me pictures on his phone and I think he looked much better as a woman than he did that night as a man.”

“Come on!” I exclaimed, “and you mean to say you didn’t hook up?”

“No, I don’t know if I said the wrong thing but as suddenly as he showed up he was gone. Said he had to be home.”

My friend and I both assumed there was a wife at home keeping him on a short leash.

“What happened next?” I asked, figuring it was probably only about 9:30 and there were 2 ½ hours to showtime.

“I was thinking of packing it in for the night but I was restless. I had also seen enough people come into the club to know that in my skirt, blouse and blazer I was a bit overdressed. So, what is a girl to do? I left the club, and headed to a Ross: Dress for Less store on the south side of town. There, I spent about an hour trying on a variety of dresses, skirts and blouses. I took in two loads of the 8-item maximum before I settled on buying an olive green dress, flowing loosely from the empire waist. It was so comfortable, accentuated my chest and would fit in better back at the club.”

“You went back to the Parrot?” I asked.

“Not before discreetly changing into the new dress while in the store parking lot.”

“That must have made for some interesting viewing on the security cameras?”

“I said I was discreet!” she retorted, “Well I think I got about the last parking spot at the Parrot. Things had obviously picked up as they got closer to showtime. Flashing my wrist band from earlier I gained entrance, picked up yet another coke and leaned against a wall. Then things got interesting for me. Two girls who had been playing pool invited me to join them. Turns out they are a lesbian couple, originally from different states in the Midwest but they hooked up in south Florida before settling in Lakeland. Now, lesbians are not noted as always being t-friendly but these girls were great. We shared stories, we laughed and I watched as they played pool. They also had this idea that as a first-timer at the Parrot I should take part in the drag show when they called up the first time visitors and I could get a free drink. I was game for that and one of the girls thought it a great idea that I would give her the drink.”

“How did that play out?” I asked.

“It fizzled out,” she lamented, “Midnight came and the show did not start. But not bad for ‘gay time’; it was only about 15 minutes late starting. The performers looked gorgeous but oh my God, the sound system was so bad it was tough to listen to the music. When the first girl circulated the room picking up her tips she wasn’t even trying to keep her lips in sync with the lyrics. But at least she had a fistful of dollars! I said goodbye to my friends and bailed out as the second performer was coming on stage. I called it a night.”

We took a little break before my friend was back to talking about her weekend in Florida. Then she was back at it.

ADVENTURE #2

“I had some clients to see in St. Petersburg. I also had plans to visit a MeetUp group I had read about. They were meeting the Saturday evening in Largo, one of a conglomerate of towns making up the St. Pete/Clearwater area. The group is known as the West Florida Transgender MeetUp. As late as the show at the Parrot got started the WFT group started early, 5 PM. Turns out they ended early, too.

“There were half a dozen t-gals there who knew each other well and me and one other. The regulars seemed like interesting people. There was champagne and nibblies for those who wanted some but at first; they were not a very inclusive group. There was no attempt to outreach and make us strangers feel welcome and no organized discussion, just the odd bits of banter. I think that came from them all being best pals with each other.

“I didn’t really get to know them until we all went to dinner at a new LGBT-oriented club/ restaurant. We got into an animated talk about all their plans to go to the Keystone Conference coming up in Harrisburg. I was amazed how central the Keystone is to their lives.”

“It has become a big deal, hasn’t it?” I interjected.

“Yes, but learning about how they were going to travel and who they were going to meet was not advancing my social life so I made excuses and headed to my next destination, the Quench Lounge.”

ADVENTURE #3

“I know the Quench Lounge,” I interjected, “I was there once when they had a karaoke night. Kind of a hard place to find, isn’t it?”

“My Garmin took me right there,” came the reply, “and besides it was only two blocks from my motel.”

“I settled onto a bar stool, positioned where I could watch everyone and everything happening in the club. Nothing happened for a while then just like in Lakeland a guy came over and started to talk with me. If anything, he was even cuter than the Lakeland guy. When I introduced myself, he replied that his name was Stephanie. I did not think I heard him correctly but yes, he called himself Stephanie.”

“Not so strange. I have done that,” I commented.

“True but followed that up by asking about my surgeries and when I said I’d had none he offered that he had had bottom surgery.”

“What?” I exclaimed.

“Yes, apparently there sat that gorgeous man dressed in a cardigan and slacks calling himself Stephanie, sitting there with no breasts and no penis.

“Talk about the worst of both worlds!” I muttered.

“Mind you he seemed to be a very nice person but no penis! That sort of lowered my interest. Then in walked Holly, the other ‘outsider’ from that Meet Up group. I’d like to say that we three had a great conversation but Holly and I sort of latched onto each other and left Stephanie a bit on the sideline.”

“I guess the prospects of giving oral sex to him were pretty dim?”

“Right about that,” replied my friend, “but Holly had some interesting stuff to say about living in the closet at home and going so over-the-top femme while on the road.”

It turns out that Holly was staying at a bed & breakfast run by a pair of TS ladies that I had known years earlier. B&B and certain favors on the side, if you know what I mean.

“Holly and I decided to leave at the same time. She went her way and I went mine. It wasn’t until I was back to my motel that I realized how tired I was. I only got as far as undressing to bra and panties before I fell asleep. Yet it wasn’t even 11 o’clock.”

“Well that wasn’t much of an adventure,” I commented, “that is unless you rolled over in your sleep and popped one of you boobs.”

“Yes, but it set up what turned out to be an incredible Super Bowl Sunday for me. I’ll tell you about it later,” she added as we smiled at two approaching gentlemen.

And I will tell you about the rest of her weekend in Florida next Sunday.

“I know we are not to believe most of what we hear and we are not supposed to take strangers into our care but this woman was in real distress?”

“How could you tell her story was real?” I asked, “She could have been a swindler or working with an accomplice.”

“Mascara,” was the reply, “fake tears do not leave blobs of mascara caked under the eyelids. It looked like someone had tapped out some Morse code under both eyes.”

“Ah, I get you,” I agreed.

Tags: crossdressing, featured

Category: crossdressing, Transgender Fun & Entertainment