Hi, it’s Jack. The escort in London, UK.

(He asked for my name, sent a photo and asked for a photo back. We talked about why I’m doing his project, why I advertised on the UK Craigslist, etc. I condensed some of the questions I asked and comments I made, such as “I agree” because who cares; this is about him, not me.)

Why did you become an escort? You cater to both genders?

I’m straight. And I’m happy to do dinner dates with guys. And I have male voyeur clients who pay me to do live sex shows with female escorts too.

What inspired you to become an escort?

I enjoy good restaurants and sex… So I thought why not get paid for it?

But how did you figure out women would pay for your company? Do you have a steady clientele?

Yes… A few regulars. Through my first online advert.

What do women want? What kind of women do you sleep with/ date?

It varies. Most are married. Not all. Not always sex. Sometimes just companionship. Massages, dinner dates, drinks. Wedding plus-ones.

Are they attractive? Do you date outside of your work?

Usually very attractive. [They’re] often in London on business from overseas. Yes, I date casually too. I’m currently single, but my last long-term girlfriend was fully supportive of me escorting.

How many women have you slept with?

I’m guessing between 500-700.

How do you pick up regular non-paid dates?

I’m just a charming, well-dressed, polite Englishman.

So women approach you?

I’m quite chivalrous. Of course.

Do you ever approach?

Rarely. London is a very progressive and liberal city.

What’s the biggest mistake women make when dating?

Many women plan their “future” too soon, with men.

How soon is too soon?

It’s not measurable by time. It’s measurable by understanding someone.

And what about the male mind?

There’s no one version of a mind… Male or female! The biggest mistake people make is pandering to the gender stereotypes. When they should highlight the similarities not the differences. I’m successful because I understand people — not “men” or “women.” I just happen to be straight so I end up in bed with women.

What if a very plain (by your standards) woman came on to you, not to hire you… How would you treat that situation?

I’d politely say I was flattered but not looking.

Never “pity sex?”


What if she paid?

The legal status of escorting in the UK is complex. I can legally only charge for my time and companionship. Whatever then happens during that time is the choice of consenting adults. Dinner and drinks yes. If we had a spark and an attraction, we could have sex too.

What do women like in bed?

Again, it varies.

No, I know that. Let’s approach differently. Would you be up for anything? And I do wonder if there’s an increase in S&M type of stuff after 50Shades?

I’ll show you the advert I use with my female colleagues…

Hello respectful gentlemen and voyeurs of London. We are Kelly and Jack, an established, friendly, confident and open couple based on ____. If you would like to join us for various levels of involvement, please let us know…

250 to watch

300 to watch and touch

500 to join in (safe only)

Prices are per hour, but we are not “clock watchers” so you might easily get two hours for the same price.

Kelly is a hot, tall bi blonde, 22-year-old model (think of Lara Stone and you’re on the right lines!). She’s quite submissive, and happy to dress to please for your viewing pleasure. If you are feeling particularly generous, we are happy to include an extra hot girlfriend if you’d like to watch a live threesome. Ask us for prices, if that’s your thing.

Jack is a 40-year-old charming yet dominant Englishman. He will seduce Kelly and bring her to multiple climax before your eyes.

Please note, we only either host at our apartment in ____ or travel to your pre-booked hotel. We will also attend swingers’ clubs with you for the same rates. We don’t attend private residences.

We are happy to voice verify or cam to prove we are genuine. We will also send you a couple of pics.

Our age difference makes us ideal for student/ teacher or even daddy/ daughter roleplay shows. We are clean, polite, educated and respectful. You’ll be in our home and we expect manners and non-pushiness. That said, we will have a wonderful time. Cash only for first 2/3 meets. Thereafter we are happy to set up a standing order if you’d like regular monthly shows.

But you go separate ways too?

Yes… It’s an act. We role-play a polyamorous foursome sometimes for clients. And yes, there’s a definite 50Shades effect.

Are you in love?

Not currently in love. Been single since January.

I mean with Kelly?

Ha ha ha, she’s gay! Just a friend/ escort.

But she sleeps with you for the performances?


What kind of woman are you into in your private life?

I only date bi girls as a general rule. They help me select the girls I work with. And we all continue partying after the client has left. The sexual intensity of being passionately kissed whilst getting a blow job is mindblowing.

So they [the real girlfriends] are a bit like scouts?

Ha ha ha a bit.

But these pick-ups are just for fun?

Threesomes are mildly addictive… I couldn’t live without them now. (I’m a freelance ____ too. The escorting is just a fun sideline for extra cash.)

Have you ever turn down a paying request and why?

Yes. Poo/ pain/ blood, etc.

[I thanked him, he told me to look him up in the UK, we wrapped it up with emojis.]