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Your Top 5 Questions When Booking A Trans Escort

The Author, Sweet Amy Maxine, will be answering your curious questions when it comes to booking a trans escort, from the perspective of a trans female.

What is the correct terminology to use? Is it rude to use terms such as shemale, ladyboy and tranny? What’s the difference between Transgender and Transsexual?

I’ll start with the last question. Transsexual is somebody medically transitioning from male to female (or vice versa). Transgender is an umbrella term that includes transsexuals, non-binary, gender non conforming, cross-dressers and drag queens.

The golden rule is simple. If you’re contacting a trans woman, use female pronouns as you would talking to any woman. If contacting a trans man use male pronouns that you would use to talk to any male. Generally speaking, it is considered very rude to refer to a trans woman as a shemale, ladyboy, or tranny. Just don’t, if you want that booking. Some trans don’t mind those terms so much, and even describe themselves as such in their profiles. Still play it safe, what someone calls themselves is not always what they’ll accept being called by a stranger. Ask her before calling her any of those terms, or referring to any other trans person by those terms.


It’s my first time with a trans woman, and I’m nervous. What can I expect?

In terms of what services she offers, first fully read her profile. If that doesn’t provide answers then contact her via her preferred contact method (text, email, call etc) and ask. Say hello, and get to the point without being lewd or crude. Good manners get answers and bookings!

Outside of the service details, what else can you expect? This part is no different from meeting any other escort. A friendly welcome, an expectation of cash up front, of the full fee, for the time you have booked her for, and then perhaps a bit of playful chitchat about what you’d like to do as you both undress? There’s no itinerary at that point! Rest assured that while we most likely don’t show it, we’re nervous too! Women are often a little self-conscious, yes even sex workers, and trans women are no different in that regard. As the provider though we’re familiar with those first-time jitters, we’ve all had our first time at some point, and in any case, it’s our first time with you!! Communicating is important so your escort can empathise and work with you to calm those nerves and fully enjoy what’s on offer.

She will expect you to stay within the stated boundaries and not overstep them or even ask to overstep them; that’s the fastest way to turn a girl off! And no means no. If she’s redirecting you or giving you instruction (here do this instead, go slower, wait, condom first, stop, don’t use your teeth, OMG fuck me hard etc) then do that without fuss. Again, simple respect, no different than with any lady, trans or not.

You are expected to leave on time without delay. She doesn’t owe you anything past what you’ve paid for. You might feel like you have a special connection with her, that’s great! Re-book her asap. Despite how good a time you had, don’t overstay your welcome or she might charge you for the overtime or refuse to re-book with you. If you’re needing a shower/clean-up after sex, do that before the time ends, or do that at home. She might even join you in the shower if you ask nicely. But that’s all on paid time, not after. Respect her time and she’ll make the most of it.

Some escorts offer one orgasm only, and then the client has been awkwardly expected to leave immediately well before the time is over. Some offer multi-shot (cum more than once) and enjoy spending the whole time you booked for with you. Ask about this when booking so you get the service level you desire.

Expect the booking to end immediately and be told to leave if you cross boundaries. Don’t expect any refund, she booked out that time for you. You do not buy consent when you pay an escort. You buy their time with you.

The services she offers are implied only and are subject to your behaviour towards her. Consent can be revoked at any time, even during sex. We like our clients to have a good time and re-book etc, we also don’t expect to be abused in any way during your time with us. As in with any other business, behaving badly has consequences and in the least, you’ll be told to leave immediately.


Do I have to perform anal or take it?

Consent is always at the forefront of any sexual encounter! You don’t have to take part in any sex act that you don’t want to do. Same applies for the escort!

Communicate your wishes with your escort! Not all trans escorts offer giving anal but most will willingly accept it. Some don’t offer anal at all. Refusal to perform anal (or any sex act) is the right of either party, for any reason. Whether it be nerves, refusing to wear a condom, size of the penis, presence of STI, or just not feeling the moment.  You buy her time, not the sex. Enjoy your time with her in other ways that are mutually enjoyable. Communication is everything!

Many of my clients, especially first-timers, are nervous and are unsure about everything but are open to trying out something like anal, give or receive. Your escort will gently guide you in a way that is comfortable for both you and herself. Listen carefully, and speak up as well.

Anal can be a very enjoyable experience, or a painful horrible one, for either person. If you don’t like it, it’s okay to stop! Sex isn’t just penetrating a hole with a penis! It’s about showing care for each other and enjoying the moment. You’ve paid for a good time, and that is only possible when you are both communicating and you’re not expecting too much of yourself or her. If she is willing to try something out with you then go slow and enjoy. If it doesn’t work, your escort will guide you towards something else. Don’t let it bruise your ego.



How can I ask about her equipment without sounding rude? How do I know if their penis is still functional?

Personally, I prefer the sentence  “I don’t want to seem rude in asking, may I ask you about your penis and whether it’s still functional?”

Often I’m rudely asked if I can cum for them. Pressure much? Vagina owners don’t like being pressured to cum and neither do we, pretty much guarantees we won’t! Simply ask if she is capable of getting/maintaining an erection if that is important to you. Some trans women prefer to use a strap on to perform giving anal either because of a personal choice or erectile dysfunction issues. Personally, I use Viagra. If you are curious about whether she can cum, ask, but don’t let that be the defining feature of whether or not you’ll book. That’s really shitty, and you’re missing out on a great booking.

“How big are you” is another cringe-inducing question. Bring a measuring tape if you’re that curious, don’t harass us with size questions. Sometimes that is already answered in the profile or you can see in a picture on the profile. Don’t reduce us to a penis though. Icky. Not a good start, if you make it past that to a booking. We’re women, have some class when asking questions, please!

I often have clients ask for cum in mouth, i.e. they want me to cum in their mouth. Besides being unsafe, it is also illegal. It is also illegal to offer it. Don’t ask, even if you don’t worry about your health, we care about ours.

Here’s a quick note on orgasms, especially in regard to trans women who have a penis:

Orgasms are not just physically produced, mental and emotional stimulation is vitally important as well! You’re horny when you contact us, and when you arrive. I get that. I bank on that and pay rent with it. But until you arrive, we know almost nothing about you including what you look like. There are some mental gymnastics going on that gets us past greeting and into the service. Getting to the point of orgasm for a trans woman escort is a bonus which is often the result of treating her like a goddess and being mindful of what she needs. It should not be expected! It’s a girl penis and a girl brain under the influence of some pretty serious hormones that change the way a penis works and responds.


Am I able to perform oral sex on them, as this is a huge part of my fantasy

If it isn’t already stated in the profile/advert ask her! Most trans escorts I know are happy to give and receive oral sex. If in doubt, ask! Some offer a quick blowjob service, and in most cases, this does not cover any mutual touching or oral. It’s a one-way service with you receiving only. Again, if it isn’t mentioned in the advert and it means a lot to you, ask!

Mutual oral features in almost all of my bookings and surprisingly many of the best givers are first timers! It’s a special thing being a part of something that is a client’s first time experiencing.

Again, when booking or during your booking don’t ever ask for natural services. And begging is gross. That includes oral. Don’t ask, assume everything is with a condom on. If you don’t like condoms, try Tinder or Grinder instead, a sex worker/escort is not for you. I don’t look down on anybody (including other sex workers) who do perform BBBJ (bareback blowjob), everybody is in charge of their own bodies and risk management. I cannot condone it and if asked I always refuse on the basis of my health comes first, then the New Zealand law which will prosecute me and yourself and charge us $2000 each. Really bad luck if someone got an STI and a fine as well! Not for me thanks!

Summary: Every woman is different. As is every sex worker. Some have a penis and testicles. Some have just a penis. Some have a designer vagina that is indistinguishable from any other natural grown one. Some offer full service, and the definition of that changes person to person. It may or may not include kissing, anal give, anal receive, oral, and any other service the escort chooses to provide or exclude. Read the profile carefully before asking questions! It is very frustrating fielding questions already answered in our carefully prepared adverts. If in doubt, respectfully ask!

There’s no shame in being attracted to a trans woman! In a world where we face so many challenges just because of who we are, we welcome it! Many clients have told me that they wonder if they’re bi or turning gay by being attracted to me or enjoying what I have. I tell them not to worry about labeling themselves. If they’re straight, they’re still straight. If they’re bi, they’re still bi. If they’re gay, I call bullshit or they’d have booked a male escort! A booking with me is not by any means a lesson in Trans 101, that’ll kill the mood haha! It’s a lesson in me instead. A very exciting lesson!

If you’ve read this far though, you are awesome and I can’t wait to book with you! Sex is a messy incoherent adventure, and everybody involved is a student regardless of their experience level.

Book your trans woman escort and enjoy a whole new world of sexual exploration and satisfaction with your trans etiquette knowledge!


The Author: Sweet Amy, trans woman private escort.

Hi I’m Amy, also known as Sweet Amy and Sweet Amy Maxine. I started escorting in February 2018 with no prior experience or knowledge of the industry. My first client was my first time with a man, my second client took my anal virginity. Hey, shush, I was curious lol! I also wanted strong boundaries and no messy relationship stuff. I genuinely care about people, and I didn’t want the messy situations that can happen if you fool around with friends. I have 2 dogs, 3 cats and a normal “civvy” job. I’m also a hairdresser, though I do not work in that job anymore. I have however given a client a haircut after his main booking, he paid me what I normally charge for a haircut. I’m truly a medley of sweetness LOL! I have been medically transitioning since mid-2015 and yes I am wanting the full surgery. How can I be an escort when it relies on men wanting me for the body part I hate the most? It owes me back pay for the years of awkwardness it has caused me. The least it can do is pay for its own removal and pay for things that help me feel pretty! The people I’ve met along the way, other escorts, client’s, NZPC workers, have all enriched my life beyond what money could ever pay for.

Sweetest regards, Amy Maxine.
Twitter: @SweetAmyMaxine
Instagram: @Sweet_Amy_is_here
Profile: NZ Pleasures Amy Maxine

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