Jeremy is a former escort, starting in the business at the age of 19 and working for 10 years. He was kind enough to take the time to answer some reader questions and some of mine. I hope you find it informative.

What exactly did escorts do to get/keep an erection before Viagra?
You have to be someone who can *find* the horny in a situation.  90% of my appointments always started with a massage (I am qualified) – there is a sensuality to a massage if done properly, regardless of the person you are massaging.  That is an excellent way to get the erection started – maintaining it just takes a little of self motivation along the way

Have you ever formed an ongoing (non sexual) friendship with a client? .
No.  The vast majority of clients are “professional” clients.  They know what they can expect and more importantly, what is expected of you.  I only ever had one client who wanted “more” – that required a conversation that was very delicate in nature and you just have to remember that the client is a person who may not necessarily understand the nature of the business.  Once the ground rules were explained further, he was fine.  Actually, he turned out to be a great client.  I only ever saw him once maybe every three months, but he was always a pleasure.

What got him into the business? Surely he didn’t just answer an advertisement.
LOL – no I did not.  I got into the business one night at a night club.  I had a man make a pass at me – a very good one actually – but I wasn’t interested.  He wasn’t my type but he seemed like a really nice guy.  I tactfully said no but was happy to chat with him.  After an hour he just turned to me and said “There is a lane down the street.  I really want to blow you – and Ill give you a hundred bucks”.  i was a very broke student at the time so I said yes – which surprised me more than him – and the rest was history.

How did you get comfortable with the idea of having sex with those physically unnattractive to him? (Overweight, underweight, older, etc.)
Here is the secret – EVERYONE has SOMETHING that is attractive about them – it is LITERALLY whether we wish to see it or not.  For some it can be the eyes – others the smile – for some it is their cock.  I had one client who had a birth defect that left him with a crooked spine and one leg shorter than the other.  He had endured a lot of operations and had a great many scars, BUT he had a gorgeous cock.  I mean, one of those that just LOOKED good.  I called it the Goldilocks cock.  Not too big.  Not too thick.  Just right and visually perfect.  Now – for the first few appointments I focussed on the cock because it was a HOT dick.  That is how I formed the connection with him.

Professional sex workers are always able to find SOMETHING about someone that is attractive – in many cases these are actually great people who are our clients – and we can be attracted to the personality. If you are relaxed with someone, the rest is easy.

The most unattractive client I ever had was a hot, professional guy in his late 20’s who had the model perfect body, amazing looks, HUGE cock – but was so fussy and so rude I couldn’t get hard.  I ended up politely handing ALL his money back and getting dressed and leaving.  He was GORGEOUS – but the most UNATTRACTIVE PERSON who had ever booked me.

Was it ever really inconvenient to respond to a call?
So many times it wasn’t funny.  There was ALWAYS the 3am phone call – but that is just about timing.  Let’s talk on the toilet – ill with the flu – out to dinner with friends – in the middle of a family dinner – just leaving the dentist – for these times I was always “fully booked but happy to reschedule for another time” – 90% of the time it was fine.

How often do they come across a client who has a visible STI? eg a herpes lesion, and how do they react in such situations
You always react CALMLY.  Part of being a sex worker is the ability to communicate well and connect with someone.  I always made it MY choice to undress a client.  Mainly because it got the sex part of the booking off to a good start for them – but it also gave me the chance to check them over.

When I did find something, I would always make sure I had one hand ON the client – shoulder, arm, hand etc – forming the connection……. I would politely point out what I thought the problem was – hand back ALL the money – and let them know that I would be VERY happy to see them again when they had been checked out and taken care of.  And let me tell you, not ONE person was ever offended.  They were all very grateful for both the respect and concern I showed them.  And they all came back and many became repeat customers BECAUSE I showed them respect and concern.

How do you get past the fact that you may just have zero attraction to a client?
Like I said – Unless you are a moronic bastard, you can find SOMETHING attractive in someone.  You find that thing and use that to make the connection with the client.  I had one client sadly who was that person people liked to joke about the guy falling out of the ugly tree – he was also incredibly awkward – that was very hard.  The only thing I could do was grit my teeth and do my best.  It was one of the few times I put the ever present porn video / dvd that I carried in my bag on so *I* would have something to focus on.  But that is the worst thing that can happen.  And that is why you carry some porn.  It is often a ‘horny’ thing for them and an emergency life ring for the worker.

What is the kinkiest thing a client has ever asked for and did you do it?
The kinkiest thing a client asked me to do was to piss on him whilst riding him like a horse, i.e. He was on all fours neighing like a horse, me on his back in the ‘saddle’ so to speak holding onto REAL reins in one hand, and a bottle of water in the other, whilst letting the golden stream go all over him.  And he LOVED it.

The thing I was asked for but refused was a client who wanted me to crap on him.  He offered me 5 thousand dollars to do it.  But I wouldn’t.  I thought to myself if I do this, then that’s it.  I would not be able to respect myself.  So I said no.

Fulfilling a clients request to humiliate them was one thing, to do something that intentionally humiliated myself… that is another.

How do you set your boundaries of what you are prepared to do? Is it a personal comfort level or dictated somewhat by an agency?
In an agency setting, you lay out what you will and won’t do in the interview.  Then they sell you on what you will do, and protect you from the things you won’t.

As a private operator I set my own boundaries, but I let mine be somewhat more flexible.  But they paid for it.  The more out of my comfort zone, the higher the price.  Like when I blew the judge under his robes IN his court chambers.  That one didn’t come cheap.  In fact, it paid my rent and bills for a month.

When you have a high profile closeted client, as I know you have had, is there a discussion about confidentiality, is it assumed or is there a contractual clause with the agency you worked with?
All of the high profile clients usually avoid agencies, because of the prickly issue of third party verbal agreements.  With a private operator, you are entering into a verbal contract between two adults conducting a business transaction on a handshake – and that is a legally valid contract.  It usually meant that the phone call was VERY long because they would tell you they were high profile but not who they were.  When they got to a point in the conversation where they were prepared to make the booking, you would usually get an address but no name.  Now, these were usually five star hotels or houses in VERY nice suburbs, so you knew that there was a measure of truth to it.  It wasn’t until they opened the door that you ever knew exactly who it was.

I have had several high profile sportsmen, a couple of television celebs, and several social identities.  None of them had an initial phone call under an hour.  But they made up for it in the fee.  Those people knew how to tip, and they rarely booked for anything less than an entire evening.

Starting at 19, do you have any regrets now that you are several years outside the industry?
The only regret I have is that I wasn’t better with my money.  I should have bought a house or put some of it in investments.  But I did help my friends and my mother out.  But I wished I had been less of a party animal and more of a property animal.
Ah well… it was a fun life when I did it.  The lesson has to be that if you are a worker – SAVE – the money will NOT last forever.

Did you have any clients offering more money for unsafe sex?
I had clients offer obscene amounts of money for unsafe sex.  I absolutely refused for the simple reason that – not only am I pro safe sex – I was not about to ruin the product “my body” just to make some extra cash.  HIV is forever.  But there was always the next client. So… no was no.

Would it be safe to assume your family doesn’t know about your past as an escort? If they did, how do you think they’d react?
No they did not know – but I have a mother who once cut the hair of trannies in Sydney so I genuinely am not sure.

NB: There is no suggestion that any of the men in the photos above are escorts. They are merely used as a pretty add on.