Not the Vacation She Had Expected

What is her social life going to be like without the Craig’s List Personals to help set the course to new relations, Linda wondered. Then a chance meeting with a ‘fellow traveler’ opened her eyes to new possibilities.

Not too long ago news came out that the online classified ad company known as Craig’s List had dropped their popular Personals section of the ads.

They said it was because the U.S. Congress had passed a regulation making firms like theirs responsible and liable should a third party use an ad placed with their service to lure someone into sex slavery or some other trouble. I cannot see a regulation such as that standing up to a court challenge but I guess Craig’s List decided it was not their hill to die on. All of a sudden and without prior notice they abandoned their personal ads.

Just like the traditional newspaper personal ads the Craig’s List personals allowed people of like interest to get together for relationships lasting a lifetime or perhaps as short as a few minutes.

Over the years as the service became more popular I had watched Craig’s List expand and refine how individuals could self-identify and also search for others.

The search could be classified as Casual Encounter, usually the most popular, but also Miscellaneous Romance, Strictly Platonic and Missed Connections. Searchers could identify themselves as M, F or T as well as various combinations of couples such as MM, MW, WW. So for instance if one was a man looking for a transgender person to play with he’d put his ad in the Casual Encounter section as M4T. In his ad he might further refine information about the age, body type, and whether she had breast implants, a penis or both.

When I travelled I used Craig’s List a lot to find companionship in the town I was visiting. It filled a gap as in many places the ‘trannie bars’ and the admirers who frequented them were disappearing from the streets. Or perhaps it was the growth of Craig’s List that was causing the demise of those pick up bars.

I’m still not sure how it will affect me but for a t-gal named Jessica it has had an immediate and unexpected consequence. Let me tell you her story as close as I can remember she told me.

I met Jessica in, of all places, a casino in New York State, not far from Syracuse. I was in the area to play some golf by day and play at the casino as Linda at night. However that Sunday afternoon was rainy and cold. I decided one more afternoon as Linda would not hurt. I was playing and winning at Blackjack when I noticed Jessica walk by. She seemed passable to everyone around me but my ‘gaydar’ spotted something, I don’t know what.

I saw Jessica make her way to a bar and seem to settle in to watch a hockey game on one of the many televisions. There were empty seats around her. I decided nothing ventured; nothing gained. I hated to leave as I was up close to $100 but that was probably the right time to leave. I picked up my chips and moved to sit beside Jessica.

“May I sit here?” was all I needed to say for Jessica to read me.

“Be my guest,” was all she needed to reply for my suspicions to be confirmed. Not that our voices were husky-bad, it was just that neither of us could reach the feminine pitch.

After introductions I asked “What brings you here?’

“I’m on my way home from a holiday in the Berkshires,” she replied.

I knew the Berkshires as a sort of mountain area in western Massachusetts with lots of small resorts and some big ones. I also knew from my experience that the Berkshires will never be voted one of the top 50 nightlife destinations in America, probably not the top 100. People go there for the rustic beauty of the area or perhaps to hear the Boston Pops orchestra in their summer home. For Jessica and me it was not yet summer.

“So what took you there at this time of year?” I asked.

“Just to get away and be myself,” she said as she gestured with her hands pointing first down and then up her body.

I got it. “You look lovely,” I responded in a tone that might be construed as flirting. “How did it go, if I may ask?”

“Unusual, to say the least,” she replied. “My plans got thrown a curve but it all worked out really well and I learned some important lessons about myself.”

“Do tell,” I said, “but may I buy you a drink?”

“Thank you but just a coke,” she replied, “I have about a three hour drive ahead of me.”

Jessica continued, “As you can guess I am transgendered. I’m not sure whether to call myself pre-OP, non-Op or simply a crossdresser. But I live and work as a male. No one in my area, no one in my family knows about Jessica.”

“Not even your wife?” I asked while thinking that her situation was somewhat similar to mine?

“Sadly I lost her four years ago. She passed away but yes she did know and she understood my urges. She had allowed me to be me.”

“I’m sorry to hear of your loss. Was it sudden?” I hated myself for asking as it seemed like prying and dredging up old hurts.

“She had an aggressive form of cancer. She knew she was going and she encouraged me to let Jessica flourish. I think she knew I’d kept a lot under wraps out of respect for her. It was her that suggested that I let Jessica use our time share weeks.

“So that is what I’ve been doing, booking week long holidays at various resorts, mostly doing sports and touring by day and playing as Jessica by night. That is I was until this year.”

“Why? What happened?’

“Do you know of an online dating service called Craig’s List,” she asked.

“Of course, I use it all the time. At least I did until they closed it down.”

“Exactly! I had booked my week and paid the fee months ago and I was just about to place my ad on Craig’s List when BOOM! There it was — gone! Now how do you find play partners in a no-nightlife area like the Berkshires?”

“Well you are not that far from Albany or Springfield,” I offered.

“I did get to Albany one night but I wasn’t going to do that every night. No I resigned myself to probably being involuntarily celibate for the week.”

“Did you consider cancelling your week?” I asked. “It seems a long way to go and a lot of time to spend to do nothing.”

“Yes, I considered it but I decided to try something else. I would be Jessica -– really Jessica -– in every situation but sleeping. Normally I had reserved my Jessica activities for evenings, special afternoons and opportunities to go try on dresses. I hadn’t been dressing to play golf or go biking. If I needed to make a quick trip to the grocery store I wouldn’t bother to put on makeup.”

“Yes, what woman bothers to do that?” I offered.

“Right, but this time I was all Jessica; all the time. I had planned to bike and golf and hike and try to find a tennis partner, even go swimming and playing as Jessica at night and that is how it worked out. Once I was checked in until now I have never been in any other role than Jessica. I didn’t bother to wait for the coast to be clear to walk out of my villa. If I encountered someone, I encountered someone and we said ‘hi’.”

“Really? Wow!” I offered. That was not such a new experience for me but it seemed to have made quite an impression on Jessica.

“And you know what: it’s a good life. I thought I’d get at least a few strange and perhaps disapproving looks but no, all was good, very good.”

“Did you have to make any big adjustments?” I asked, thinking about toilet issues, etc.

“Well there was one. I’m a pretty good swimmer and love putting in long hard workouts. Happily I had bought a one-piece swimsuit that contained and concealed my breast forms but I wasn’t sure what would happen to my hair, my wig, if it got submerged. I guessed the wig webbing would be exposed and who know what effect the chlorine would have had on the coloring. So I just would swim a few lengths of backstroke, keeping my head above water. Then I spent a lot of time in the hot tub with the water jets pushing up my ‘you-know-where’. Other than that everything was good.

“At the grocery store a clerk helped me fill out the application for a loyalty card. Jessica Martin is now a registered customer at the ‘Big Y’. That saved me about $50 in groceries and gas over the week.”

“Nice!”

“It was all nice. I played a round of golf at a local 9-hole course. I went hiking in the woods and met lots of people who were all friendly. I spent a couple of evenings at the resort bar and met some nice people, engaged in some girl talk with the gals, got hot looking at one of the husbands, you know all the regular stuff women do. And of course I visited the outlet mall and got to try on a number of dresses and other outfits but did not find anything more to cram in to my suitcases.”

“But may I ask, did you not find it lonely doing all this by yourself?”

“A bit. I did try to make some contacts. I’m a member of URNotAlone and I had a couple of email addresses from a previous visit in the area but nothing came of those. Then I joined FetLife but same sort of all talk-no action sort of thing. I’m afraid there may never be another thing quite like Craig’s List.”

“I think of online dating like fishing,” I threw in, “you are not going to catch something every time you put your line in the water but for sure if you don’t cast the line there will never be any catches.”

“That’s so true. That is unless you happen to go in to a casino and a delicious catch sits down right beside you,” she smiled.

I laughed and smiled. It was a come on line, for sure, but, sadly, she had a three hour drive ahead of her and I had two, and not in the same direction. “So what did you learn about yourself during the week?” I asked.

“I’m not sure where I will go with this,” Jessica replied, “I have never really thought about the possibility of living full time as a woman. I have wanted to and sometimes I’ve considered that I should have been born a woman but I’ve always put wife, family, friends and job ahead of my own identity feelings. Now, after this week I know I could do it. I could live as a woman full time and I do not think my doing so would be offensive to anyone I loved and if it was offensive that would be their problem, not mine.

“Now I have to visit a restroom and then hit the road. It’s been very nice chatting with you.” Jessica said as she got up from her stool. “You know it was not the vacation I expected but it turned out probably to be more important for me. I learned that I don’t need a man’s sexual attention to feel my feminine identity.”

“I’ll come with you to the restroom,” I announced, “because that is what we ladies do.”

On the drive home I thought to myself that a 100% Linda/100% celibate holiday may be just what I need.

Nah!

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Tags: crossdressing, featured, opinion, Transgender

Category: Transgender Body & Soul