Was that guy hitting on me? Can't be

I've been traveling for the last few days and I was able to stop by one of my local favorites, the Vintage Wine Bar on Santana Row in San Jose. I wore a tribal pattern black/white skirt, black top and a long white sweater. My avatar to the left. I was debating between a red (my profile picture) or white sweater and I am always amazed at how one change makes the outfit totally different. I love color pops but I went with white last night.

OK, so I enter the bar and the staff remembered me and welcomed me in but the outside area was packed solid. No seats, so I sat inside happy to do some people watching. A few minutes after I sat down, a group of 5 late twenty-somethings came in and made themselves at home a few seats down from me. Moments later, one guy walks over to me and says hello. I say hello back. I did have my back to him so it s reasonable to think I was a woman of unknown age. Now, if he was confused before, he is not now. I am clearly twice his age and not a woman. He looks me in the eye, gently and briefly rubs my upper arm and walks off. I'm thinking, "That's weird. Would he do that to a woman?" Was he thinking, "WTF, how do I get away from this?"

No worries, he's with his friends now and we're done. Not. For the next hour, he'd come over to me and chat about something. Topics ranged from Pokemon Go to a loud girl in the bar, to not understanding women. Now, he's talking me like a guy, "I'll never understand women," was one of his revisit comments. I'm talking to him like a guy. Maybe I was his first cross dresser and he couldn't let the opportunity go, who knows.

It was by no means a "bad" experience, just on the odd side as I couldn't figure out why he kept coming back to me. It's always interesting going out and always fun interacting with the normals.

Get out there if you want.

After feeling those guns of yours I'm surprised he came back. Maybe he's into CDers and you do look good en-femme.

LOL Allisa!

Jennifer, yeah I think he liked you. But was trying to figure you out. you never know, he may have wanted you. That why he dist the girls and wanted to hear what you said.

Any chance he was a sister? I know in my early years, ok decades ago, I would have wanted to share but couldn't say, I am in the closet and wish I could be like you-open and lovely.

A lot of rejection, and not much love can make a guy try different things.

He might have been thinking a lot of things about you. Curious, feeling a want to be near a pretty girl, a CD himself, or just wanting a friend to talk to. He could have been hitting on you also as you are a very good looking lady. From the conversation though that you described he could have just been very open to the CD lifestyle and trying to show his support. Who knows...

Jenn,

That's a pretty crowded area, so who knows who'll show up!

Anyway, yeah he was definitely hitting on you. I've had that happen a couple of times, but at a gay bar, so... But in that area? Wonder why. I bet he really was into you. I mean if it were a joke or dare, he might come back twice, but that's it. On the other hand his friends could see him.

One nasty thought is he may have been fishing for a fight. I've seen this behavior before, guy peels of from the group, causes a confrontation or singles someone out, then the group converges, and it gets really ugly. I know your can probably hold your own, but it becomes very dangerous when you are out numbered. Keep an eye open there.

And to touch your arm? Brrrrr, that's awfully bold. Bet he wouldn't if he was alone.

Maybe he just enjoyed talking with you, and was enjoying the experience of talking without fear of rejection. Sounds like you got to do a bit of people talking as well as people watching! Win win!

In earlier discussions with my 26-year old daughter, the Millennials or in this case Gen Z are extremely comfortable with those who are gender-fluid. She's told me she knows about a dozen guys who wear skirts to dresses or lipstick and eye-liner to those fully crossdress. It's clearly not a big deal to this generation.
Perhaps the reason he touched your "guns" was to see if they were firm or soft. So who left the restaurant first? and how did you say good-bye and what was the reaction from the rest of the group?
Thanks for sharing your story...

Oh and Jen, Welcome to cougarhood!

Jenn,
I'm not sure what to make of the guy, brushing your arm may have been a little too much ?

One question were the other guys aware of what he was doing ? Were they egging him on and watching your reaction or totally unaware of what he was doing ?

I know you've been out there so many times and may have understood it but I'm not sure I can say I would be comfortable with the situation.

Jennifer, it seems to me that at first he was going to hit on you!! Then he seems to not know how to react to you!! May be his first encounter with a crossdresser!!! Any way I am glad to see it did not go bad (sour) or hostile or violent!! Best wishes for your safety as you are an inspiration to me!! Hugs and love Lana Mae

I had to laugh at this part- "fun interacting with the normals." hehe

For some unknown reason I've found that some guys get especially talkative when I'm sitting at the bar en femme. One of life's imponderables I guess. :)

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Originally Posted by tifftg

Any chance he was a sister? ...

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I hadn't thought of this a the time but if I had to bet, I think this might be it.

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Originally Posted by Meghan4now

...One nasty thought is he may have been fishing for a fight. ...

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No not a chance. He and the atmosphere was quite friendly. It was a WINE bar after all. No beer or hard liquor available.

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Originally Posted by Tina81

In earlier discussions with my 26-year old daughter, the Millennials or in this case Gen Z are extremely comfortable with those who are gender-fluid....

So who left the restaurant first? and how did you say good-bye and what was the reaction from the rest of the group?y...

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Tina, I think you re right about the younger generation. We're not as weird to them. I left first and said good buy the the staff as well as his group. Everyone smiled and said good-bye

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Originally Posted by Teresa

...I'm not sure what to make of the guy, brushing your arm may have been a little too much ?

One question were the other guys aware of what he was doing ? Were they egging him on and watching your reaction or totally unaware of what he was doing ...

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Teresa, it was weird to be touched. I would never do that to a stranger but maybe he was just a little too buzzed. As for his friends, yes, they all knew he was chatting with me as we were only about 3 feet away and I could hear their conversation quite clearly, They were just hanging out. Either he was a fellow cross dresser or he was just curious about the cross dresser in the room.

Jennifer, It doesn’t surprise me, you really do look very attractive when crossdressing, couple that with your self-assured nature and body language. You put more effort into how you look and the clothes you wear than most GGs that I know. I have heard of the term “Gynemimetophilia” that may apply to your new friend. But actually rubbing your upper arm, WOW! There are some epic comments here Allisa’s about your “guns” almost made me LOL; and Meghan’s “welcome to cougerhood”, these precious moments are why I love coming here. It’s a wonderful life to be you, thanks for sharing this amazing experience. Brenda

Jennifer,

The touching was worrisome. Many people don't seem to understand that a touch is a massive intrusion into your personal space.

I do wonder as you have intimated, that this was perhaps more about him than about you.

Finally , congratulations on handling the situation so well.

Consuelo

Jenn, You have a natural look, and have GG confidence, and it is surprising you have not been approached more often.

Maybe he was hitting on you. Some guys are really into trans and cross dressers.

Did you like the idea that maybe he was?

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Originally Posted by Jenniferathome

Teresa, it was weird to be touched. I would never do that to a stranger but maybe he was just a little too buzzed. As for his friends, yes, they all knew he was chatting with me as we were only about 3 feet away and I could hear their conversation quite clearly, They were just hanging out. Either he was a fellow cross dresser or he was just curious about the cross dresser in the room.

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I get the shoulder touch all the time. As long as it stays on the arm I'm fine. Guys who seem to want more usually touch my back between my shoulders.

It didn't feel like he was a tranny-chaser as opposed to curious. And no, getting hit on is the one component of cross dressing that makes me uncomfortable. It has only happened twice, but I have no desire to attract a guy and yet, I want to look my best and so the confusion for some guys is remotely possible. I have no problem saying, "No thanks, I'm married," but I'd rather not even have that kind of attention.

Its strange. Most straight guys wont get to close to a cross dresser or ts (once they realize she is TS). It is like guy repellent.
They have a lot of fear about how that reflects on them. Another crossdresser, or Maybe they were FTM? or just someone outside the norm.

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Originally Posted by arbon

It is like guy repellent.

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We are after all contagious (or recruiting for the agenda. I only need one more to level up)

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Originally Posted by arbon

Its strange. Most straight guys wont get to close to a cross dresser or ts (once they realize she is TS). It is like guy repellent.
...

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I agree which is why I now think he might have been a cross dresser himself (he was a dude for certain) but simple curiosity still has a ring of truth.