So I had sex with a transwoman…

A little mood music by Shibayan, full lyrics and credits at

It was an interesting experience.  A little background on my sexuality: I’m basically straight, but back when I was young (like early puberty) I had a serious, very sexual crush on one of my friends.  I tried to have sex with him and it did not go well, to say the least.

Bear in mind this was a bit before gay marriage was becoming more accepted.  So homosexuality was an issue, and people were still ignorant and thus shitty about it, as ignorant people tend to be.  Breathing the air of the time and being young, I was extremely hard on myself.  It was actually pretty traumatic.  It probably would have been better back in the 70’s or 80’s.  Then I would’ve just been going through a phase, or experimenting, or whatever.  Instead, the horrible existential question Am I gay? loomed so huge over what should have been a much more innocent experience.

Since then I have found a man attractive every now and then, usually a feminine “twink” type, but haven’t done anything about it.  In contrast, I find many, many women attractive, so I identify as essentially straight, or “heteroflexible,” to use a word that has gone a little out of fashion.  But I sometimes wonder whether I’m just suppressing my bisexuality.  Having sex with a transwoman was thus an interesting compromise between not triggering too many bad memories while still exploring that side of myself.

Plus the concept itself is hot.  In a sense, a transwoman is a woman with a non-disfiguring birth defect which forces her to have anal sex.  And grow facial hair, but that’s not as hot for me.

To protect identities I’m not going to discuss how I met this lady, but we got along well and came together pretty quick.  And the usual disclaimer with these sorts of things: n=1.  This is a one-person sample, there is no way to tell what is unique to her and what is more general to transwomen.

And sorry for the PC talk.  In the past I’ve called them “trannies,” but this is apparently a no-no, and I want to be nice even though the pre-PC word is easier, cuter and less of a pain in the ass, as usual.  I don’t know, maybe being PC is a sick joke, what with me going anthropologist on the poor girl.  Well, she knows she’s going through something unusual, too.  And hopefully it’s clear why I’m looking at this the way I am. Hopefully it doesn’t seem too shitty to blog about it.

The reality of experiences (here we go) are always less meaningful than we think they’ll be.  Maybe it’s just me, but I’m always surprised by how full life is in itself, how it crowds out the symbolism and structure we’d like to assign or find in it.  When I had sex with the transwoman, it was just that.  Real, every touch and second of the experience composed of sensory data.  The interpretations came straight.  All cigars were just cigars, to be a little oblique.

First, there was stubble.  Her mouth tasted neutral, which I appreciated, but kissing didn’t really give me sparks.  And to be fair, there are women with whom kissing also doesn’t give me sparks.  Then she showered, and we moved quickly into sex.  She was so sensitive.  Pinching her nipples made her shiver and moan.  And she knew what she was doing with her ass.  Apparently she’d gone through a period of heavy drinking and compulsive sex, so after putting the condom on with her mouth (!) she lubed herself up and we moved through positions, going progressively deeper until I was on top of her, all the way in, and really pounding away.  I wish I’d held back a bit, but her ass was so tight and really, who wants a lover who’s too worried about being unselfish?

By the way, she was attractive and skinny.  She’d had top surgery and was almost certainly on hormones.  And she was as smooth as you can get with a razor.  I honestly don’t know how she got her ass that hairless, but it was much appreciated.  And I had read online that transwomen don’t usually like to have anything done with their cocks.  They’d rather act like they don’t exist.  They want it gone.  Gone.  G O N E gone.  This proved totally accurate, and I was A-OK with this arrangement, although some curiosity lingers.

She was in some pain at not being a “real” woman.  She loved the manly parts of me; she loved to watch herself getting fucked in the mirror, her hair a mess, a big man on top.  Possibly unique to her, she loved getting fucked in the ass.  Not that I’m so experienced, but she was one of my most responsive partners, my most responsive for non-kinky sex.  I wish I’d held out longer.

After blowing my load with the force of 10000 suns, as they say on the internet, we lay there and had some pillow talk.  Not that I’m running around having a lot of sex, but this seems like normal behavior to me, but apparently the old saying that men come and go (i.e. orgasm and leave) is true when they’re fucking traswomen too.  So sticking around to chat apparently earned me a gold star.

Then I left.  We both knew it was a quick thing, but it’s kind of sad.  Getting more into circumstances again threatens our anonymity, but this is the way it is.

So.  Now that the porn is over, what’s the after-action report?

Gentials aside, the transwoman I was with is something in between a woman and a man.  The need to become a woman is mixed with some vague maleness.  Maybe everyone is like this, not really conforming to the pure gender stereotype, but it feels like something deeper, either biological or an early training.  I felt like she had a masculine aggressiveness, a masculine idea of how to be, lingering in the back of her mind, influencing her reactions.

This is the big question to me.  Does the transition ever end?  Are transsexuals stuck in perpetual gender limbo, or is there a point where the changes are complete, and all that’s left are the memories of a difficult period?

As for me, I feel pretty not-gay, remarkably so considering.  Like anyone cares about this petty bullshit, but I have to include it for the sake of completing the narrative.  For whatever reason, at the end of the experience I almost felt like I hadn’t had sex, instead it felt like I’d had a really, really, really great masturbation session. But that buzz from being close to someone just didn’t happen.

Was it my unconscious repressing my responses?  Did I just not find my partner attractive enough?  Maybe, but I think I understand what it means to be heterosexual, now.


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