illest wrote: 8 months ago
I'm at the stage I'm not so sure if this is just a bondage thing for me or a whole other repressed side of me. I look forward not only to dressing up, but just how girly I can look when I do. It's like a challenge almost.
I feel like I'm in this weird spot that I can't explain. I don't want to change gender; I actually really like being a guy.
...
Years ago during my experimenting phase I could wear a dress without doing much else and get my kicks. In my current phase, regular me and dressed me are almost two entirely separate people, almost to where I wonder if I have a split personality. Like now whenever I dress up, I need the full experience. Shaved face, concealer, eyes done(eyeliner, eyeshadow, or if I'm lazy simply fake lashes), lipstick, lipliner, blush, wig, panties, dress/skirt/onesie, knee socks or stockings. I've also recently gotten into taking pictures and video of myself.
I think it's a wonderful thing that you have decided to explore (and share!) this part of yourself - too many people go through their lives never fully expressing themselves because they feel ashamed at their secret thoughts. Personally I have found that the more one does so, the better one feels in the end - of course self-actualization is often a long and complex journey, and I would not claim I have reached the end of that particular road myself.
And I doubt it is a split personality thing - just another facet of yourself that has been neglected for a while.
illest wrote: 8 months agoI really don't like the idea of doing virtually anything with a guy; however doing acts that a girl would generally do to a guy except with another girl has hard crept into my brain recently. I guess trying certain gags dressed up(and having my wife put a certain gag in my mouth while not dressed up once) kinda does that to me.
I think I can make a good guess at the type of gag you are talking about
illest wrote: 8 months ago
I'm pretty sure I'm at a point that either I'm going to tell my wife soon or she'll find out soon enough. I messed around and left a maid bracelet in my dirty clothes that she teased me about and every so often I bring up being open to "role reversal" so I think she's at least somewhat connected the dots.
Indeed, I suspect she knows more then she is letting on

Although as mentioned by
@tiedinbluetights , things like this require care. It can be easy to create problems where there did not need to be any if being overly eager or pushy about things.
illest wrote: 8 months ago
I started getting envious; I mean if
I was a girl with a bomb figure I'd be dressing up all day in all kinds of cute stuff!
This actually made me think of something else, and preemptive apologies because I am not trying to assign motives specifically to you (those are for you to discover), but:
I suspect some of the desire to cross-dress for men is actually borne of a sort of subconscious jealousy (this is too harsh a word for what I mean, but I cannot think of a better fitting English word right now). Namely the fact that for straight men, women are the 'center of attention'. Society places a strong emphasis on female beauty, and we are constantly told that this is important, special, desired ect. And if you are man, you obviously cannot even participate in that - which can lead to feeling overlooked. As in 'you can *never* be this thing that society covets because of how you were born'.
Therefore, I would posit that cross-dressing can let one experiment with that feeling of being the center of attention, even if it is usually only your own attention, as paradoxical as it might seem. And this can be a great, even empowering feeling, so it is unsurprising someone would want to explore it!
Just a thought, one I will admit is probably not quite fully formed/polished, but hopefully it makes sense to someone
tiedinbluetights wrote: 8 months ago
It was definitely not my intent to kink-shame those who are into humiliation play. I myself am into pain-play as a masochist and as pointed-out, that is not a very easy kink to explain to those not into it, so I sort of get why some would like humiliation play.
...
I would certainly not want to come across as disrespectful to, or otherwise offend, an entire group that positively identifies with femininity, by suggesting that femininity or traditionally feminine behaviours in a man ought to be humiliating.
I did not think you were trying to do anything of the sort, but as it often goes, reading things can trigger related thoughts. And I certainly had no intention of trying to 'change your mind' in regards to liking anything like this - that is... not how these sorts of things work
At the end of the day all psychological play is a matter of perception. An easy example is how some people like to be called certain offensive or demeaning names during play - and others would balk at the same. But that is why communication between partners is so vital. One person's 'hot' is anothers trigger after all. And I fully respect being uncomfortable with playing into bothersome societal stereotypes.
My intent with my ramblings was to explore the subject from another angle and show how a male submissive wanting to be humiliated via feminization did not have to stem from looking down on women.
To put it another way: I have occasionally seen the sentiment expressed in various places that straight submissive men who are into the humiliation aspects of 'feminization' are acting out some kind of repressed hatred of women via kink. While I will not claim to know everyone's mind, I really do not think this is true for the vast majority, and in fact I think it is the opposite* - that it comes from wanting to *overcome* or reject such societal norms (either those expected of men or women) by proxy. Society, peer pressure, culture, whatever you want to call it, we all spend our lives being bent and molded by external forces. And being forced to assume a shape one was never meant to... well this can leave psychological scars. Surviving humiliation, much like surviving pain can be a deeply cathartic and sometimes even healing - I would argue it can be a way to iron out those leftover kinks (hah) from the crucible of ones youth.
*Being totally honest, I am not sure we can assign solid motivations to anything like this, and I suspect for many it is just a fun thing without much deeper meaning, but you know...
A corollary to the previous: I will admit it is pet peeve of mine when I see people imply or even outright say that any sort of humiliation or pain play in a D/s relationship is just 'ritualized abuse' when there are drastic differences between the two things and the only way anyone could think they are the same is by completely ignoring all context. Even more frustrating when this is said by otherwise kinky people, who should ostensibly understand the concept of being into things that do not really make much sense on the surface and the stigma that often comes with that.
But I think it is time for me to get off my soapbox.