I'm in love with women, but now have a recurring gay crossdressing fantasy... Help?

I'm in a pretty confusing place in terms of my sexual identity, so I thought I'd ask for some advice.

In everyday life I identify as heterosexual, and to pre-empt the confusing aspects of me, this isn't out of denial or fear of being gay or bisexual.

I literally fawn over women constantly, it's impossible for me to leave my flat without at least one woman catching my eye and me wanting to be with her.

Unfortunately I've never been the most social creature, so I never got into the dating game...

I have slept with four women, and loved the experience. They were escorts though, so in terms of self-confidence all I've got is one girl who made out with me in a club and an ex I never got very far with.

Anyway, despite this I've found myself spending a good deal of time whilst online looking into "feminisation" fantasies.

That is, being dressed like a woman, wig and all, either for purposes of being humiliated by women in a femdom style (although generally with everyday girls as opposed to actual dominatrix types) or to get with a guy, generally in the mindset of attractive women having talked me into doing it.

Now, I never find men attractive, speaking romantically and for the most part sexually too. Certain aspects of identifying with the female role and doing the things they do sexually (mostly oral) does turn me on, at least in terms of thinking about it.

Anyway, last night I tried it with an older guy who is associated with the sex industry (it was a mutual meet over the net though, not a paid meeting).

The actual sex aspects were enjoyable, but only due to the female role I took on...

I did try this sort of thing without any cross dressing a couple of times and found it boring and unpleasant, using female-centric pornography on a laptop to keep me going.

However, this time I did really enjoy myself, and it became a full blown one night stand with me sleeping in his bed dressed like a girl. I was convincing too, I think being mistaken for a girl a few times in the past in public has added to this, along with a general anxiety over not being masculine and assertive enough to seduce "real women".

Anyway, so now I'm not sure where I stand. I'd never date a guy because I've never met a guy I found attractive.

This guy was good, but as I say, only for this one specific fantasy.

He had a female flatmate who is also a sex worker apparently and the thought of that turned me on/intrigued me a lot, a sort of vague hoping she'd wander in, catch me dressed and decide to experiment with me too.

Thinking about it, being a "lipstick lesbian" appeals more than being a "sissy", by a great deal as far as this fantasy goes... But even then when I like girls generally, I never think about cross dressing or being feminine with them at all, I'm pretty heteronormative in my attitudes to them. One of the escorts (they were all independent and I researched to ensure they were doing it for the right reasons, btw, and it's legal in my country) even commented that I was quite dominant sexually.

So I guess I'm wondering if I accept this is just one sexual kink I have that is cool to explore safely when I'm young and it's discrete, or...

Well, I guess I feel kind of ashamed, like the heterosexual part of me is threatened by this one fantasy, as if if a girl I dated found out she'd lose interest and find me sexually unappealing as a man, or as if by having done this and being really femme during (looking in the mirror during dressing I'd probably be able to pass as a girl completely, definitely not a bearded builder in a wig) I've created a mindset where I'll be too effiminate in real life and the cute girls I ultimately really wish I was with, either for casual dating or something more serious, will just overlook me for the more manly guys in the bar.

I guess I'm also wondering if trying to become more masculine is the answer (working out, growing out my facial hair etc.) or if I can be slightly more androgynous and still successful with women. It worked for Bowie, i guess!

Any advice would be much appreciated.

 

Re: I'm in love with women, but now have a recurring gay crossdressing fantasy... He

Thanks for the welcome.

I guess the problem with pitching my story to people online for advice is by centering it on the feminisation stuff, I probably paint a picture quite different from my everyday life. Like, I don't dress feminine. I dress pretty standard male student, all male clothing and I LIKE the stuff. My issue isn't that I'm wandering around at work or with friends wishing I could be wearing some french panties or a skirt, because these urges don't really come to me in the slightest outside of a. surfing the net, b. the odd, very rare moments I'd try on my mothers panties and bra (I know, I know) when I was younger (and like, back then you've got to understand I might have that urge but then spend three months on standard teen porn, or webcam stuff with no feminisation at all etc.), and c. this one encounter that was like every feminisation fantasy I'd had handed to me on a plate, minus an actual female being involved.

So I definitely don't think I'm trans. I think part of it might be self-esteem, feeling the masculine ideal is what women want, and that I'm not that ideal so I end up seeking punishment perhaps by embracing humiliation through femdom, leading to this encounter? Don't get me wrong, I DID enjoy this encounter completely for what it was though. But everytime I FALL for someone, it's always female. I've been friends with guy who are clearly good looking to your average female, assertive and confident, the very image that is part of the feminisation fantasy as the male role, but never once thought about them sexually. I can't think of a single male I've met "in real life" (as in away from the sex offered to me through the net and porn) who I thought twice about outside of aspiring to be more like them. On the other hand, I actively crush on women constantly, and it's never looking at them wanting to be them, it's wanting to be with them. That's pretty much my norm. I always mention being mistaken for a girl in the past, but that's more like 5 or 6 incidents over more than a decade that just stand out in memory.

I do wonder if this has all come about in the last few months due to stress or depression. I just graduated and am now unemployed with no immediate options of employment, I'm still single at 22 with no female interest evident due to either me not appealing or me not trying to go out into the world and see if I do actually appeal to people, so my esteem isn't great. Now, i also have borderline, which can be marked by sexual recklessness and an addiction to novelity. I do think I'm very much into the novel and change... I mean, for masturbation alone, it used to be all about topless female models in newspapers for me, then nude European models, then normal porn, vanilla, then barely legal stuff (when I was roughly the same age!) then more hardcore stuff etc. Feminisation has only really been a factor in the last year or so, excluding the few times I experimented with wearing panties as a kid. I do wonder if this is all about just chasing the new until it gets old if that makes sense. Like I said, I tried normal gay encounters and don't really like them. Giving a guy oral does nothing for me. When dressed, it was more enjoyable but even then compared to being with a girl... I don't know.

But yeah, you're right. How common would you say forced feminisation fetishes are? I do know with the guys they're almost just a means to an end. With girls, I do geniunely want to take them out, to make out with them, to lie together in bed talking etc. As I say, put me on a crowded subway and I won't look at any given guy twice, but I'll probably steal glances at the cute girls and hope one will smile at me throughout. I saw a masculine guy in a club pulling a really sexy looking brunette last week and could have cared less about him (outside of him as a representation of domination, I guess, cos if I had dressed he'd have been fine even though I'm only thinking that now and not at the time) except for envy, and wishing a girl like that was into me the way she was with him.

I think I'm a 2 on the Kinsey scale? Based on actions and sex alone, that is. Romantically, at least so far and as far as I can foresee given how many cool guys I've known in life but never thought of remotely sexually, I'm definitely hetero though. with guys it seems to be either idolising them a bit as a mentor or great friend, not giving a damn, or in this case seeing as a sort of personification of domination acting
out the role some laughing gorgeous harlot in a video told me to go find.

Sorry to ramble on