The first time is always special, that’s why we asked our favourite touring trans fetish goddess
Sienna Carlisle to write something for those cis men hoping to explore an encounter with a trans
escort for the first time. As she explains, sex with a trans woman can be both enriching and
liberating, especially so when we place our faith in a (strikingly sexy) expert. This isn’t a list for the
seasoned aficionado, it’s for those taking first steps in exploring their attraction. Here’s to taking the
plunge—and realising you had gills all along.

1. Be brave
Let’s get this out of the way: there is sometimes stigma attached to sexual attraction to trans women, especially if you’re a guy who considers himself mostly straight. But this idea that straight men aren’t attracted to trans women is a massive misconception. It’s certainly not the gays that are sliding into my DMs. I can’t tell you how many men come to me thinking that they’re alone among the people they know in being trans-attracted. How can that be true when trans porn looms so large in search terms? The sheer volume of men looking to experiment online and offline is large enough that isolation seems impossible.
It takes bravery to face our desires and let go of the idea that what we do sexually has the power
to override our social identity. Then we can begin to let go of the fears we might harbour about trans
women and what it might mean to be with them romantically and sexually. Be honest, and be brave
—I promise it will be worth it.

2. Be bold
There are oh-so-many options when it comes to exploring sex with trans women. It’s not for nothing
that people sometimes describe it as ‘the best of both worlds’. A friend of mine says trans girls have
an erotic superpower. Something about our femininity smacks of liberation. You should feel
liberated too: be yourself and follow your desire.
When it comes to negotiating activities, try to be up front about what you want. When you ask for
what you want, ask for everything you want, even if it’s something you might like to experience
after a few meetings. Whether it’s hot and heavy, darkly perverted, or simple-seeming: go for it.
When I have a client who is able to express himself, it not only helps set expectations, but it helps
me to structure our time together.
You might be completely unsure of specifics but just have a feeling, or an image that pulls you.
That’s ok too. In fact, that’s more than ok—that’s exciting.

3. Pace yourself
Just like you shouldn’t rush through an exquisite meal, sexual experimentation with a beautiful trans
woman is something that you should try to be as present as you can for. It’s better to take it slowly,
savouring every moment. Once you’ve taken the time to choose a trans provider you like,
you should feel confident in that choice and let her guide you through entry-level activities before
moving onto more intense or intimate ones, especially if you’re interested in BDSM or power play.

It can be tempting to want to go straight into an extreme scene you’ve seen in porn without
recognising that you’re not physically or mentally prepared for it yet. When you experience too
much, too fast, things can go by in a blur, leaving you disoriented about what you did and didn’t do,
losing touch with your pleasure along the way. This goes for all kinds of sexual experimentation:
take your time.

4. Get informed
If you find yourself buckled with anxiety about actually doing the things you fantasise about with a
trans woman, why not do some research? I’m more than happy to answer any questions you might
have, but I’m sure you don’t want to waste our precious time together asking me to troubleshoot, for
example, the ins and outs of anal play, sexual safety, or what the letters in BDSM stand for.
In addition to trans issues, you can easily find information about douching, safer sex, kink and a range
of other topics online. You can also consult your GP, therapist, a book, Reddit or X for more
opinions or advice. (For the record, my big tips for the above are to douche and then fast for at least
an hour before the play, get tested regularly, and read a stack of filthy French novels…)
But if you’ve made it this far down my list you’re probably well on your way to being as informed
as you can be, and enjoying the freedom that comes with that.

5. Relax
I’m now going to say something that might sound counterintuitive, because I’ve just been talking
about differences. The fact is that being with a trans woman isn’t that different to being with a cis
woman.
Though there are specificities to trans sex, we’re not reinventing the
wheel. Just like sexual dynamics might differ between you and women of different sizes, races and
personalities, sex with a trans woman will probably feel, smell, taste and look very similar to sex
with a cis woman—with the addition of that ineffable X factor I mentioned in point two. While
being with a trans woman can definitely be an opportunity to explore your own queerness and
sexual horizons, we are, at the end of the day, women like any others.
So relax! You’ve chosen well, now all you have to do is let go and do what comes naturally. I wish
you all the best for your erotic explorations, the fulfilment of fantasies, and an all-consuming post-
play afterglow.

Sienna is currently touring London. Don’t miss her!