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Williamsburg at the Right Time (Part 1 of 2)

  • Kendra Chelsea
  • Oct 4, 2016
  • 4 min read

One car, two cars…That was the biggest dilemma we had going into our little mini-four-day vacation; well in the beginning anyway. The thing was that after reaching out to our mayor, telling him that I wanted to return something to our community, especially after all the kindness that I had received after coming out, they graciously appointed me to the Education Advisory Council. I did not remember my first meeting was to be held two days into our trip.

“I am going to have to take my car; I have to drive back on Tuesday for the meeting.” I mentioned to Kimberly as I noticed she was packing.

“Just tell them you had this vacation planned, I think it is kind of silly to drive 3 hours for the meeting, and then what drive 3 hours back. That is really going to ruin your vacation.”

I shrugged her off; she should have known that, that’s not me. In twenty years I had not been late for work, rarely use sick leave, even worked through my heart attack. “Doesn’t matter, I said I was going, I am going.”

Me being the on-going third wheel might have had something to do with it also. Tony had just came back into the picture and I was beginning to think of this trip as some sort of lover’s getaway. The only thing I really had going for me is a message I got from a Facebook friend, “Hey, you are in my area, maybe I can spend an evening with you all.”

Susan, I saw her before at Freddie’s but really only briefly and for some reason I had not seen too many of her posts but I was definitely interested in someone, anyone, that might take the attention of me, being alone.

Midway through our 3 hour drive to Williamsburg I get a text message from her. “Hey what time are you getting there? Where should I meet you?”

I was actually kind of surprised at the text, honestly I thought that her offer to meet up with us was just a polite thing said in passing. “Well it looks like Susan is joining us today.” I mentioned to Jamie immediately after I got her message.

“Susan, Susan from Freddie’s?” Jamie asked while she tried to keep her eyes on the road. “Oh, are you sure you know what you are getting into?”

“Wait, what, you two? Um…” I replied and looked over for Marcie’s reaction. “You dated?”

“No, well, there was this one time. No, it is okay but, it will be interesting.” She responded.

It felt as though there was some inside information going on that only I wasn’t aware of so I had to dive a little further into Jamie’s personal life. “What do you mean interesting? And…Susan is meeting all of us, not just me, I don’t think…”

“Well she is exactly what you are looking for; you know Susan is a crossdresser, not transgender. Plus she is strictly a top.”

I have to admit, my curiosity got the best of me and I had to get more information but at the same time I wanted to be sensitive of the fact that the love of Jamie’s life was sitting right next to her. “Hmm, okay, I have to say the top thing, sounds interesting, but...”

“Let’s just say she needs a lot of attention.” Jamie chuckled and then fiddled with the radio; I assumed that she wasn’t comfortable with the conversation so, I let it go.

So we arrived; well we stopped and got more wine and more groceries and then we arrived. And Jamie started cooking as soon as we put the food away. “Oh lord, if she cooks like this every day my diet is shot.” I said to myself as I hooked up my Amazon Echo. “Alexis, play Madonna.” (So what, sometimes I am a transgender stereotype, what of it)

And I had one glass (or five) of sangria and waited patiently for Jamie’s awesome cooking to be done. Of course there was a lot of solo dancing, by me. Overall, it was a great night with great.

And then one by one, people began calling it a night. “I think I am going to take a shower and go to sleep.” Marcie said as she stood from the couch.

“I’ll be right in after I put away the leftovers.” Jamie responded. “Where is Kimberly?”

“She went to bed an hour ago.” Tony answered, “Which reminds me, it’s time for me to go too, got a good woman waiting for me.” He continued making a special effort at a dig at me.

I smiled up at him; that has been our thing since we were teens. Each trying to outdo the other when it comes to insults and jabs. I could tell that even though I changed my gender and name, we were still the same friends that we always were.

And just like that, everyone was gone except for me…and Susan.

“What do you think?” She said as soon noticed everyone had left the room except for us. She held out her arms showing off her nightgown.

“Cute…” I responded.

“How about this?” She said making a slight motion toward her “package.”

“Been here, done that and not sure I can go back.” I thought to myself. “Susan…” I began and then paused to get my thoughts straight. “I am straight, I like me, beyond that it gets a little complicated.” I groaned attempting to resist my SPSP condition.

“Well, it’s a good thing that I am not a girl then huh?” She responded.

Hey, a girl can only resist her sickness for so long right? I immediately thought that since Kimberly had Tony and Jamie had Marcie, I might as well couple up even if it were only for one night.

“So…” Susan reiterated, “What do you think now?”

I pushed her nightgown aside and moved in closer. “I think it is going to be an interesting night.” I said as I moved in for the kill.

Virginia Beach

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