Interacting with older men

[ellbee]

OMG, I just ran into an older gentleman neighbor in our building's front lobby. Eek!


Nah, he's so freakin' sweet. I love older guys. How can you not?


He was kinda taken aback tonight... Getting all flustered because I'm totally workin' it, baby!

I think he really liked the skirt, one of my shortest. My legs are wrapped in a heather brown pair of tights. One of my tightest, femmiest winter coats, too. No wig or make-up, but a hat & hood. I look pretty cute & legit.

I was in front of him, so I had to do double door-duty. Made him do most of the work, though I don't think he minded too much.


I felt so vulnerable. Kinda sexy, too, LOL... Just him behind me, the two of us together, getting kinda late. Well, now that the first time is done with, next time I think we'll both be a bit more relaxed. Oohh, this could be fun with him!


Seriously, whoa. That was awesome. First time I actually interacted with him in a skirt. I don't think he knew how to react to my shapely gams, ha! But he did seem to err like treating me more like a GG than a guy, given the circumstances.

Guys like him are cool, yo. I think it's just a matter of meeting the right ones. If he was a little younger & a little taller? Hmmm...



And if you are an "older man," yourself? Well, you guys are the best! Gotta love their lifetime of experience in treating women the right way.

[Julia1984]

Ellbee, I'm 56, so I don't know if that counts as " older" in your book. I guess it depends on your own position. That said, I feel about 25 inside, I don't think that ever goes away, even if bits of the body want to disagree.

[Krisi]

Does this "older man" know you as a guy? Did he know it was you dressed as a woman?

And are you gay?

[alwayshave]

Ellbee, I have never directly interacted with an older man outside a LGBTQ bar. However, in a "straight" bar at a hotel, the negative staring from older men was not comfortable.

[Jessica Secret]

That's great Ellbee!! Thinking about attention from a guy right around when I turned 20 is probably why I had such a strong desire for a boyfriend, which I achieved the goal of and I'm still with him to this day.

[Natalie5004]

I have a hard time imagining what it would be like to have a boyfriend. I bet I would be a lousy girlfriend.

[docrobbysherry]

Have fun with him, Elbee!

I've had old "Admirers" flirt with me. But, the only men that have really come on to me have been about 1/2 my age!

I have had a few older trans proposition me, tho. How do they count?

[April Rose]

ellbee, as an older person who is essentially 18 for the 4th time, i'm betting he's thinking "gee, I wish I could pull off that look....."

Go ahead and have fun with him. He's probably enjoying it just as much as you are.

[RoxieGrl]

Yeah, I KNOW that I would be a lousy girlfriend to a guy. I really don't care for guys (my personal preference). One of the reasons I dress is because I like women, and many of the things that make them women. For starters, the great diversity of clothing. The colors, and patterns are simply nothing compared to what is acceptable for a man. Come to think of it, I need to get a haircut. My hair is about shoulder length, and after looking at all of the men's hair styles, I cannot say that there is one that I like. They are all so boring. On the other hand, there are many women's hairstyles that are very interesting, and I wouldn't mind wearing them.

[ellbee]

What is an "older man," anyway, right?

Welp, if there's some dude in your general physical vicinity -- and you're younger than him?


On the flip side, I'm sure there are some young whipper-snappers who think *I'm* an older man!


Krisi, I wasn't en femme. But all I had to do was throw on a little padding, some make-up & a wig, and I would have been smoking hot. Put it that way. That's how I was presenting. I can look in my full-length mirror, from various angles, make my head "disappear"? Yeah, hard to deny that it looks way more like a GG than a guy, from the neck down.

Winter hat, hood. Clean-shaven baby-face. All a girl really needs!


Anyway, my older-gentleman neighbor & I have seen each other around before. Me while in various "modes," heh. But not usually many opportunities to chat & interact. Don't really know him that well. So, naturally a bit cautious. Guys & this stuff? They can be a bit of a wildcard, in my experience. So, I tend to play it safe, and slowly feel it out.

Still early, but I have a good feeling about him.


Am I gay? No. But the more my femme side takes over, bisexual thingies tend to arise. I used to sleep with a guy before, years ago. Would I do it again? Won't rule it out, in my case. But as with my first & only, it would have to be with the right guy at the right time in my life.

But that's not what this is about. Instead, I enjoy stepping into a societal role that's more often typically reserved for GG's. Nothing wrong with chatting with the guy -- but more like a GG would. If that includes a little flirting, so be it. Maybe just a personal preference, but I always feel better with guys older than me, in this arena.

And yeah, the "eye-candy" thing is definitely a factor, too. He probably wasn't expecting to see a natal male in a femmy women's outfit that makes him look way more like a "real girl." Some guys kinda dig that, in my observations & experiences. These guys may look, which is cool... But a lot of them won't touch. All good here.

Some of these guys may "play along." They'll be their usual guy-self, but they'll view & treat you more like a GG, if it's just the two of you around. Not 100%, obviously. But you'd be surprised. My neighbor-bestie & I have talked about this... She's fully aware that some guys are just like that. Doesn't mean they're gonna end up in bed with you or anything, but some will be more comfortable, more intrigued, make more of an effort, maybe be extra nice to you, while interacting -- compared to other guys who might try to avoid you at all costs!


My GG-neighbors have all been awesome. It's the male-neighbors/visitors that I'm more "worried" about. For example, someone mentioned some older men who obviously disapprove. Yes, they exist. One in my building. I just keep my distance, even though it pains me a bit. Eh, whatever. That's life.

Just try to focus more on the positive people, instead.

[MonicaPVD]

I find myself around older men all the time, mostly because I tend to frequent the kinds of places where they congregate. What I have found is that there are generally two types. First, the old school moralist who looks at me like one might gawk at Madonna riding horseback on Pope Francis. Second, the intrigued guy who hasn't been intimate in years with his wife of four decades. He will often approach, converse, flirt, and then retreat, satisfied, and head home to safety. There's a smaller minority of chasers, but I will spare you the details.

[Helen_Highwater]

Ellbee,

You reminded me of a time only a few years ago where I was at a railway station having just parked up. I'd usually take the stairs up over the footbridge to get to my platform but as I got to the lift an elderly gentleman had already called the lift and the doors opened just as I passed. Seemed daft not to take advantage on a free ride up so I opted for the lift.

The elderly gentleman proved to be just that and did the gentlemanly thing and said, "After you" and gestured for me to enter the lift first. I thanked him and I must say he seemed totally unfazed by my presence.

[ellbee]

Yeah, I suppose it's just sort of ingrained in some men... And apparently some of that transfers over from interacting with GG's, to, well, people like us!


Honestly, I ain't gonna turn it down, ha! At times it might catch me off guard, maybe even becoming a bit surreal. But I gladly step into that role once quickly realizing what's going on. It's a space you really don't get to experience, as a guy. You recognize what it is, but it's now directed at *you*! You're on what you usually know as the receiving end, for a change. The script has flipped. You're now seeing "how the other half lives."

I've been dong this off & on for a long time now. The places & faces may change, but it never gets old to me!



I also want to mention that homosexuality & bisexuality, as well as crossdressing, existed before we were even born. These days, people (particularly younger generations) can be fairly open about it. However, some of these older guys today? Well, maybe for whatever reason(s), they're a bit more private/discreet/hush-hush on the down-low about it... Heck, maybe they're even still internally wrestling with it, having headed down a more traditional/conservative path in life that wasn't best-suited for them. But, that what guys like him did back in the day, so...


And here they are today, with you, sharing a moment in life together. And given your outward presentation, one of you is obviously way more open about it than the other, LOL. Not saying that every guy who interacts with you is gay/bi, or has some sort of curiosity/attraction to gender-bending. *However*, perhaps something to keep in the back of your mind as you're in his company, as a possibility. And even if he were, he may still hold back, perhaps wanting to be with you but instead chickening-out or something, simply as a product of his times, or inexperience, or whatever. So, you two never hook up. Eh, for the best, then?


And that's perfectly fine, if you think about it. The important part, IMO, is that you're both experiencing a positive and, how I view it, a wholesome time with another, in your own roles in your own ways. I suppose one could argue that there's a rough template or set of guidelines, that you can refer to, that's more or less universally-accepted, at least in your part of the world. The guy plays the masculine role, you play the feminine role. Both on the same page. It works, as long as you remember to "stay in character" -- which can be easier said than done. Time & practice is all one needs to get the ball rolling.

Bottom line? You get to make a bit of a connection with another human... In this case, an older gentleman who kinda-sorta views & treats you as he would a female. Depending on how well you play your parts, as well as your willingness & ability? You two could potentially turn this into something pretty cool, no doubt!

[Rikidee]

Ellbee, I just live this thread, how you present, and how you describe the interaction. I also love the same kinds of interactions. Your description makes me feel a little special! Thanks Riki

[BrendaPDX]

Hi Ellbee, A very interesting thread. I have only had a very few interactions with "older men" and they have been brief but pleasant. If I hadn't been wearing so much makeup a blush may have been notices once or twice. Fb is similar, when I asked why me, the general answer is "I appreciate any pretty women", when I remind then that I am a cross dresser they don't seem to care. I am going to keep an eye on this thread. Brenda

[docrobbysherry]

Here's a wake up call for u all. When u actually become an old man like me? Young women open doors for u!

Today, a young women opened a front door and held it open for me. When I gestured and said, "No, u go first". She insisted I go in first!

I can't say I liked that, but it is what it is!

[ellbee]

Sooo... A thing kinda happened earlier tonight?


Have a few days off from work, so said screw it & got all dolled-up!

Well, as much as I do the en-femme thing, anyway. Went heavy on the brows, eye-liner & lips... All ya need, really.


Wig, of course... With a cute winter hat.


Look a similar level to my avatar, to give you an idea? But a more casual, outdoor winter version. Looking kinda legit, but I need to get my eyes tested, too, so...



Anyway, out in my car, as usual. See/hear older gentleman neighbor pull up in his car... YES!!


Oh, I could not pass up this opportunity, baby! I don't get dolled-up very often, and I had to strike while the iron was hot. Stopped what I was doing halfway through, quickly packed up my purse & out the car I went. Didn't catch up to him until the front lobby, where he was getting his mail.

Ummmm... Can I say something?

Still kinda processing what happened, and will have to sleep on it, but...


I believe there's a really strong likelihood that not only did he not recognize me -- but he didn't even know I'm a *guy*!!


I softened my guy-voice when we were speaking. But I also have some *4*-o'clock shadow happening, due to the spontaneity of girling it out tonight. Who knows, maybe I'm being overly harsh on myself, and maybe the type of lighting in the lobby & hallway didn't really pick it up.


So, like... WOW! Even though I'm wearing a short flared dress with tights under my long winter coat, he could not stop staring at my face. Took me a moment to figure out why... Cuz when done right, make-up can make you look kinda hawt! Plus the wig/hat combo provided for some realistic volume & styling, really framing & softening up my face.

My expert beauty team ( ) definitely pulled its weight tonight. The way he was looking at me, for as long as he did? Okay, that was a pretty big compliment. Men don't look at other men like that -- men look at *pretty women* like that!


Hmmm... This was strange. Surreal.

But totally worth it!


Certainly been a while. Like I said, I need a day or two on this...

[Krisi]

Let me just remind you that many men get very upset when they find that someone they have been flirting with, dancing with or sharing drinks with is a man and not the woman they though it was. Sometimes this leads to violence.

Be very careful.

[CrossKimmy]

That feminine urge I think is the phrase