A Male Escort Answers 21 Questions About Getting Paid to Sleep with Successful Women

"I had plenty of orgies when I was younger so it’s nothing I haven’t done before."

Madison James works as an escort in London and also runs his own mortgage brokerage company. He also blogs about his experiences.

I get asked this question quite a lot. I enjoyed pleasing women, so I decided to put 100% into it. When the women you’re dating start thanking you after sex because of how you make them feel, you tend to notice that you're kind of an anomaly. What better way to spend quality time with amazing women from all walks of life than in a job like this? I’m a firm believer in doing what you enjoy and figuring out a way to earn a living from it. This was coupled with the fact that I believe we all have the right to do whatever the f*ck we want in life so long as we’re not hurting anybody.

Everyday? No way, definitely not. The kind of woman I attract requires me to research and plan our encounter from start to finish with room for the unexpected. I try to limit my bookings to one per week due to the commitments I have because of my main business. I’m also a single parent of a 17-year-old daughter so I like being around for her, too.

Yes, she was one of the first people I told. She had no idea what it was but she soon cottoned on after I explained, and having lived with me for the last 12 years she wasn’t particularly surprised. She actually thinks it’s pretty cool but I spare her the details.

My bookings tend to be between 4 to 6 hours. Occasionally they're 24 hours, which is my preference because I get the opportunity to create a real fantasy for her. Money isn’t an issue for this type of woman, and she usually wants to escape some sort of high-powered stressful job for an evening or a night. When she comes to me, she’ll often express how she wants to feel but will leave the intricate details to me, which is such a turn-on.

It can vary so much but there’s a lot of hotels, nice bars, restaurants, long drives in the countryside, shopping trips to Selfridges (especially the Tom Ford fragrance counter), weekends away, quiet evenings around the fireplace with a bottle of gin, massages, BDSM sessions...

Last week, after an intense session with a client, we ordered room service and then decided to go for a late night drive through central London. It was completely unplanned but she loved it despite being half scared to death as we raced down Park Lane. Then when we got back she got into bed, I lay between her legs on my side, my arm around her waist and slowly licked her clit until she was close to orgasm. Then she pulled me inside her. After that I massaged her and we fell asleep.

I'll give an example: a client who I’m meeting this weekend. She’s a successful businesswomen who lives and works abroad. She’ll be in town for a week and has booked me for 20 hours from Saturday through to Sunday afternoon. She simply said she wants to escape and not worry about anything whilst she’s with me. She has an interest in BDSM but wants to be wined and dined in a luxury hotel with all the trimmings—she’s very classy.

We started with a very honest and open conversation on the phone discussing why she contacted me and what she hoped to gain from our time together. We've often exchanged messages since then. After speaking with her, I put together an email detailing the logistics of our evening together in terms of the hotel to book, the type of room, our dress code, dinner reservations and other important details that I won’t discuss.

I then started working on a script for our evening of carnal pleasures (this is the bit that she doesn’t see as I want it to be a surprise). As this was our first time meeting, I didn’t want to create a full BDSM play session for her because it requires a lot of trust. The script I created is tailored specifically to her taste. There’s a strong element of BDSM in there but it’s mainly about sensuality.

If I don’t feel I’m suitable for the client, I’ll let her know in the most polite way possible. There’ll be a million tale-tale signs but it all boils down to your gut instinct. The way they communicate with you, the questions they ask, trying to haggle about the rates and prove how big my d*ck is, which is a clear indicator that they’re not the type of client I’m looking for. Imagine calling up a female escort and asking her off the bat how tight her vagina is.

wine glasses, cheers,

(Image credit: Getty)

I don’t do submission, water sports, humiliation (giving or receiving) or anything too dark. Kissing is definitely allowed if we have agreed to spend time together.

I read the situation. Often the woman will instigate if you create the right atmosphere. They’ll get really turned on and suggest that we skip dinner and head back to their hotel room. Maybe me stroking her neck whilst discussing how she likes to orgasm around the dinner table might have something to do with it...

Many of my clients are married and they intend to stay that way, so a nice hotel is usually the location of choice. Although sometimes they’ll request that I visit them in their home if they’re single or the husband is away on business.

My hourly rate is listed on my site at £350, but I tend not to take hourly bookings as I don’t get that much pleasure from a quick random ‘shag'. My average booking is about £1,000 for 4 hours, plus travel expenses. I charge up to £2,500 for a 24 hour booking. Most female clients tend to be very different from guys when hiring escorts. Many female escorts I know can literally turn up, act like a porn star for an hour, and once the guy cums, he’s content. My clients require a lot more time and attention. Sex is mental after all.

I’d say intelligent, professional, wealthy and interested in exploring their sexuality. Just think Clare Underwood from House of Cards (what a f*cking killer wardrobe). The average age is between 38 to 50 but it does vary.

Not really, I tend to be quite in tune with my surroundings and if something feels off, I excuse myself.

Yes, occasionally a client has too much to drink, especially if I’m meeting a couple and they get carried away. I’m pretty laid back but I know what does and doesn’t work for me. My peace of mind doesn’t have a price tag so if the vibe is off, I’ll let them know. On the whole, the women I meet are all very nice.

Not very often but there’s a lot of demand for it. I’m happy to see couples but my preference is one-on-one with a woman. Couples usually ask for me to f*ck the woman while the guys watches and jerks off, which is a strange experience when it first happens but pretty standard in this line of work. I’m straight so I don’t do anything with guys, but sometimes the woman wants us both to f*ck her at the same time. If the chemistry is good it can be a lot of fun. I had plenty of orgies when I was younger so it’s nothing I haven’t done before.

Ok, so lets call spade a spade: escorting is prostitution and with that comes certain preconceived ideas, like having to sleep with absolutely everyone who calls you up. Maybe some operate this way but that doesn’t work for me.

Hotel room door

(Image credit: Archives)

One of my most enjoyable experiences was not too long ago on the 25th floor of Marco Pierre White's roof garden where a client/friend of mine had a full on orgasm sitting on my lap as I subtly caressed her body. There was more to it than that of course, we had a very strong connection and had spent a lot of time exploring our sexuality together. I was left feeling somewhat in awe of her ability to not give a f*ck who was watching (yes, there were spectators pretending not to notice) the not-so-subtle orgasm taking place right in front of them. It was so awesome I blogged about it (you can read Madison's blog here.)

I enjoy many things from the wining and dining, to meeting new people from all walks of life, to watching women orgasm uncontrollably as they curse me in foreign languages. It’s the way they lose control when they cum that really turns me on.

Not often, but occasionally it can happen. It’s not particularly hard for me to keep my emotions ‘at bay’ as such because I don’t feel the need to. I can have an intense connection with a woman and still have her remain a client if she’s able to do the same.

I’m affectionate, and genuine friendships can develop. Emotions sometimes blur the lines and make things difficult.

I was seeing someone recently who I was really fond of but she found it difficult to handle my line of work. The closer we got, the harder it became for her, which I can fully accept. Eventually I had to let her go, it wasn’t easy but that’s the way it is. Despite what some people think, I don’t always get to have my cake and eat it.

Paisley Gilmour

Paisley is sex & relationships editor at Cosmopolitan UK, and covers everything from sex toys, how to masturbate and sex positions, to all things LGBTQ. She definitely reveals too much about her personal life on the Internet.