X-Rayed Sex: “The Transgender Surprise”

By LeNair Xavier

A monthly column by Thotyssey’s favorite ex-pornstar and current sexpert.


I once saw someone at a bar, and couldn’t help but be interested. I concluded they were male, but their outfit left me wondering if they were masculine or effeminate. Whatever the case, I still found myself drawn to them.

This person dressed in a way that made them a perfect balance of male and female. Even down to their jeans with one leg looking like a cut off skirt, while the other leg was full-length with a rip in the knee. Since I’m all about originality and individuality, plus them being cute, I was no doubt drawn to them.

We kept exchanging glances at each other. However in that deep dark of the bar, I wasn’t sure if them looking at me was actual interest, or simply them catching me trying to be sly in checking them out. The latter would have meant that I was lacking in my skills that night.

For I’m good at checking out guys on the sneak. So well that they never have a clue until we actually hook-up, and I confess it to them later.

At one point, I slipped into the bathroom knowing some action was going on in there. So it was chance to do my usual observations of sexual behavior. This person though, came in after me. Being now in such close proximity, there was no denying what the glances we were exchanging meant.

One stare, and we passionately started kissing. They slammed me against the wall, and me being the erotic mirror that I can often be with a playmate, I grabbed them, and pulled them closer to me. Grabbing the ass of their jeans and giving it a hard massage because their pants were too tight around the waist for me to get my hands down there to feel inside.

He said, “Why don’t you get condom so you can fuck my pussy.”

I was a bit put off by this because of how I feel about guys calling their asshole a “pussy”. The originality of their look made me able to overlook that… this time. So because of the reputation of the bar I was in, I was already prepared with condoms and lube packets. So I replied, “Done.”

I put on the condom, put some lube on it, and before I could put some lube in their hole, they were guiding my cock into them. I fucked their hole, and there was no doubt I was loving it. However, when I top, I need extreme comfort, and there were others in the bathroom touching on us that interrupted my comfort. So my cock slowly softened to the point of slipping out of them. I went long enough for them to feel satisfaction, but what they said to display that satisfaction gave me the utmost shock.

They said, “You just made this tranny very happy.”

Yes, you read correct. They said, “tranny”. Their word, not mine.

I gave a shy smile over the compliment. Then we proceeded to a post-public sex makeout.

During all of those kisses, some questions I had during the sex finally got their answer because of their after-sex reveal of being transgender. Such as:

  • Why didn’t they bend their knees more? For I have topped guys their height from behind before, and they always have to bend their knees a noticeable bit for their asshole to meet my cock. And;
  • Why did I feel a small gap above and under my dick when entering them? A gap that felt very much like…
  • At that point, I realized both questions had the same answer. It’s because it was not an asshole that I was entering, then fucking. No, it was actually a vagina.

To be honest, I felt a bit tricked. Because a gay male discovering he was inside a vagina when he thought he was inside an asshole is a big deal. This would have been even more inciting of fear if the sex was without a condom. And not out of fear of an STI, but out of unwillingly becoming a father if the FTM transgender person wasn’t far enough into transitioning to have had their uterus and ovaries removed.

Maybe it’s partly because I’m bisexual, but it’s definitely because I’m more sexually open-minded that I didn’t throw a fit at them revealing they were transgender. But what if I wasn’t either of those things? Sex in public made the omission of them being transgender more safe. But what if we were alone? This might be how some transgender people end up enduring physical harm in their sexual encounters. And please note, that by no means is me blaming the transgender person for becoming a target of that harm. In fact, I totally blame the assailant.

For the assailant exemplifies the answer to the question all this leads to… Why are some transgender people not forthcoming with this information about themselves early on in the encounter?

The answer being:  It’s because the transgender community have come to realize what I have been exposing about the gay male community for years with racism, ageism, sexism, financial status, and even HIV status. That gay males talk a good game of being all-inclusive and accepting of one’s situation, but in the end, it’s just that, talk. Case in point is how some of you probably cringed when I mentioned realizing that I was in a vagina and not an asshole.

This means that we gay males as a whole need to do better. I’m not saying that you must have sex or get in a relationship with any and every good-looking transgender person you meet. I am saying we need to be more welcoming so that they feel comfortable revealing this truth about themselves early on in a sexual encounter, and even more so, in a romantic relationship.

I’m inspired to say all of this because I ran into that person again about a month later. Same bar, and same bathroom, but this time, guys desperate to touch and too socially inept to just play voyeur killed my hard-on even before I could get inside them. Also, I suspect this person was not my first transgender encounter.

A couple of years, I couldn’t tell if the good-looking person I was checking out was a male or a butch lesbian. Later, when they decided to go down on me in the backroom, I figured they were a male. I then suspected them of being a transgender male, because I was sitting down during the blowjob, while they were squatting. In that position, I often reach down to massage their crotch a little. When I tried to do that, they moved my hand.

One thing my late coming out (age 30) has made me try to inspire in others is being honest about your sexual selves to yourself and your partner early on, in a backroom tryst or long-term relationship. I feel the same rule applies to transgendered people.

For sex with a transgender person requires all parties to change to some extent from the usual sexual intercourse we have been taught as “the norm”. So that honesty from a transgender person is essential. But it can’t happen until we gay cis males as a whole show ourselves more welcoming to the idea.

So let’s get on bettering ourselves, shall we?


LeNair Xavier can be found frequently at the Cock, and at various other exhibitionist-friendly venues. He has a blog called L’s X-Ray Vision, and can be followed on Facebook, Tumblr, Twitter and Instagram. He guest blogs occasionally for Kiroo.com.

X-Rayed Sex Archives

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