Thursday, July 2, 2020

Chat Me Up Redux – Part 2

My recent Chat Me Up post received a bunch of Comments that you can read at the bottom of that post. It also generated a batch of emails. You can read the second batch of those emails following this period.

Hi Stana,

You asked about being "chatted-up"....

Here's my story - eons ago, I was femulating while staying at a hotel in Atlanta. I was in a room on one of the very top floors, so waiting for the elevator took a while. As I was waiting for the elevator at my floor, a middle aged, dapper (slightly greying hair) Southern gentleman on my floor came to the lobby area to wait. As soon as he saw me he gave me a charming smile and said "Howdy, good evening ma'am." I responded with a quite sweet, "I'm well thanks, how are you?"

It was clear that he was wanting to chat more, but I was really nervous and was really hoping to not have to chat more. Thankfully just at that moment he got a call and the elevator came. We both got on and I waited, hoping that the call would last the whole ride down.

Alas, that was not to be -- the ride was too long. He got off and quickly resumed chatting me up. We chatted about this and that (my voice is pretty passable). And, as he talked I was charmed and getting increasingly turned on by him. If he had kissed me there, I would have fallen into his arms. As he got off, he turned to me and said: "ma'am you look absolutely stunning  - hope you've got a great date for the night!" -- and at that point, I'm ashamed to say I just came in my pants. I was so embarrassed at that though - that I immediately went back to my hotel that night and didn't go out again for a while.

But, that was a long time ago, I'm far more confident (but far less attractive) in who I am now.


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Dear Stana,

I am responding to your post and question about being chatted up (hit on/propositioned/asked out) by men.  I spent time recently to write about an experience I had within the last few weeks to share with my daughter, so I have a lot more details and thoughts than would be suitable to post on your website.  It may be a bit more than you bargained for, however....

During the COVID-19 pandemic, I know I should limit my exposure to other people, but shopping is one of Lisa’s most enjoyable type of outings.  It lets her see, feel and (before COVID-19) try on new clothes and shoes.  Lately, I have been searching for a new purse and have been to Nordstrom Rack and TJ Maxx on my quest.  I have in mind exactly what I want: a black genuine leather crossbody bag with a gold chain strap that would work for almost any occasion – I just don’t want to pay $150 for it!  When I learned that Macy’s was open, I thought I would don my mask and stroll through their large selection (with a focus on the bags on sale).

I had no luck in the bag aisle although I did find some jewelry I liked, because Macy’s not so helpfully positions the jewelry very close to the purses.  I avoided the temptation to splurge on jewelry anyway, reminding myself why I was shopping in the first place.  After I exited the store, I removed my face mask.  I was in the open air and it was about 95 degrees and humid (not what is meant by an “N95” mask!), making my cloth mask particularly stifling outside.  As I got to my car, a man in his late 50’s/early 60’s driving alone in a black suburban called out insistently to me: “excuse me, lady, excuse me!” I thought he wanted my parking space, so I turned toward him with a smile to tell him he could have it.  What he said next really floored me.  “I just wanted to say that I think you are really pretty.  Do you think I could have your number?”  I did what many a self-respecting woman would do in this situation -- I acted a bit embarrassed, shook my head no, and turned around and got into my airconditioned car.  That was the second time I have been propositioned, not the first, so I probably should tell you the first before I talk about my feelings this time.

It was about 15 years ago, when I was younger (and prettier – sort of!), but also less experienced traveling the world as Lisa.  I was shopping at Walgreens in the makeup aisle when an older man (again, late fifties to mid-sixties in age) approached me and said something like “hi there.”  As I didn’t know him, and was feeling very self-conscious and a bit fearful, I didn’t turn around, although I had seen him out of the corner of my eye and knew he was speaking to me.  I pretended to be too engrossed in picking out the right lipstick to care.  He pressed on, saying “you look like you know how to work out.”  Again, I ignored the comment. Very obviously my biceps are large for a woman (although within the range of a woman who lifts and not obviously masculine, because I am a swimmer and my arm muscles tend to be elongated by the swimming).  So, I wasn’t offended by the comment in and of itself, and I didn’t think he was “outing” me as a male dressed as a woman.  But, I clearly offended him, because his final comment was something like, “you don’t have to ignore me, you know.”  At the time I was really struck by being hit on by a male.  I don’t dress provocatively, and I certainly don’t seek it.  Moreover, I don’t think that I am that attractive, either as a male or a female.  After mulling over the episode many times, I concluded at the time that there are a lot of lonely older males who think nothing of propositioning a woman who they see as “within their league”.

Which brings me back to the more recent event.  Truthfully, the incident created conflicting feelings for me.  In my heart, I am pretty sure that I pass about 85-90% of the time, because people aren’t looking that hard, I try to minimize the “tells” and I have become comfortable in Lisa’s skin (being out and about, in every type of location, 5-10 times per month).  This fellow clearly had time to assess me. Does that mean he knew?  He seemed authentically interested, so I didn’t think so at the time.  When I looked through the open window and into his truck after he called out to me, he seemed like a big dude.  Maybe he simply likes “larger” women (at 5’9” and 162 pounds, I am on the smaller end of the male spectrum, but I would qualify as a large female).  Another point is that at the time I thought I looked very presentable:  I was wearing a long, white flowy cotton skirt with eyelet detail, paired with a violet tiered sleeveless cotton top (both perfect for the weather).  My top revealed an appropriate amount of cleavage (enough to scream female, but not so much as to make me look like I was trying to attract the wrong kind of person).

So, if one’s standards were not particularly high (and a guy driving a truck trying to pick up a woman by calling to her can’t have very high standards), a man could judge me “acceptable.”  Of course, based on an inquiry to my wife and daughter, this sort of thing doesn’t happen that often to cisgender women who don’t go out at night or go to bars, and it has happened to me twice in broad daylight (albeit with a good fifteen years or so between the episodes).  That suggests to me that I cannot deny the possibility that these two men were attracted to transgender women.  Perhaps they think we are easy and are attracted enough by us --  they don’t want to indicate they know we are trans as it would break the “spell” that they are hitting on a woman, but they don’t respect us enough not to try to pick us up while they are out shopping.

Another observation is that it bothered me a lot less the second time, probably because I am so much more confident in my female presentation.  My attitude was simply to say to myself, “that was an inappropriate thing for that guy to do.”  We live in a misogynistic world, for sure, and this perhaps was just one further piece of evidence of that fact.  If so, it is as much a part of Lisa’s reality as it is for any other woman.

A further observation is that I am glad that both of these events occurred during the daytime and in public.  I know that many attacks against transgenders women come when a guy, or group of guys, get temporarily “fooled” and then somehow associate that with their internal homophobia, resulting in them taking out their anger on the trans person.  I had an encounter at twilight in a small town I was visiting last year, where I was forced to pass four drunk 20-something men on the sidewalk.  As a I walked past them, one of the guys spoke to me and said, "do you think you could handle all of us?"  It was a disgusting comment, and totally inappropriate, and it caused me to pause in my steps because I wanted to say something in response (something a mother would say, although I couldn’t come up with something quickly).  Thankfully, one of his companions quickly interjected, "leave her alone" -- and they did!  I also was stalked by a man late at night in a park 20 years ago and it was the single scariest thing that has ever happened to me (so much so that I made sure I talked to my daughter about it afterwards to make sure she had taken a personal defense course).  With these experiences in mind, I will continue to remind Lisa to be careful before, during and after every adventure en femme, because there is absolutely no way she is passing as cisgender 100% of the time.

Still, I am out so often in a very tourist-heavy city (at least it was pre-COVID-19) that I have encountered a large number of people as I have gone about my business.  One of the most common interactions is people stopping me (Lisa) to ask for directions.  That happens several times a year, and the people who stop me are young and old, male and female, alone and in groups, and of various nationalities, so I sincerely doubt any of them are doing it to check me out.  As it has never happened to me when I was alone and presenting as a male (and only a few times when I have been out with my wife as a couple), I have concluded that Lisa is a very non-threatening older female.  In fact, I strongly suspect that this occurs because I smile all the time when I am out as Lisa because I am happy and because I feel prettier when I do.  Mother Theresa said, “every time you smile at someone, it is an action of love, a gift to that person, a beautiful thing.”  I take that comment to heart.

One final point that may be meaningful as you compare my experiences to your own or others who leave comments on your blog – I never go to bars or clubs, whether as a male or as a female.  As Lisa, I do everything a regular person my age would do, including going to movies, concerts, salons, stores, museums, beaches, church services and parks.  Those things make me feel more “me.”  I have never attended a support group, never been out with a transgender friend and never sat by myself in a bar to have a drink.  I am sexually attracted only to women and I am in love with and faithful to my wife, so I feel no need to go to bars or clubs to meet others.  It is likely that those feelings, together with my common way of expressing myself, are the primary reasons my experiences (as related above) are so “pedestrian.”  I am simply a human being walking through life and enjoying myself as Lisa.


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As a heterosexual femulator (XY) that socializes almost exclusively en femme, I've been approached by men a handful of times.  It's simultaneously quite flattering and a bit unsettling, as it's not always clear just how well the person doing the "chatting up" understands the dynamic.
I can say that I've always very politely declined such advances, and I've been fortunate enough that none of them have pushed that boundary beyond where I was comfortable.  That doesn't necessarily mean I haven't have to repeat myself a couple of times though...

My interactions with women (XX) while out en femme have been almost exclusively positive, although they're not so much "chatting up" unless I'm in an appropriate venue for that.   I've gotten help with uncooperative hair, compliments on wardrobe (especially shoes), and just friendly interaction in general from women.

Jamie N.

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Source: Venus
Wearing Venus

Professional femulator, circa 1905
Professional femulator, circa 1905


  1. AnonymousJuly 02, 2020

    I've been out dressed 4 times I think (from my increasingly patchy memory) - always with a GG friend - never alone.

    If I was spoken to by a man while out dressed, I think my instinctive reaction would be to exit stage left asap. There's nothing a man has that would be of any interest to me.

    It would be a totally different reaction though if a woman were to try and start a dialogue with me. I think I'd welcome the opportunity to try and explain myself to her and to seek validation from her.

    I would see a man as a threat - something to be avoided at all costs - whereas I'd welcome the chance of female friendship if the opportunity were to arise.


  2. AnonymousJuly 04, 2020

    Hello Stana,
    I love your blog and post only once in a while. My comment is not
    fully on target, but it is related.

    Some years ago, I finally attended a meeting for CD's. When I got there
    I was a bit nervous, but then I got dressed and joined in with the conversation.
    One of the other "girls" was very attentive to me. While I was not angry, I felt
    the attention was a bit much. I did not follow up in any way, and I only went to
    one more meeting before finally moving. Best wishes to you and all your readers.