An escort’s guide to older men

If you are a 22 year old escort, just about all the men you meet are older. Actually, old enough to be your father, if not your grandfather. There is a wonderful saying that “money is the tribute age pays to beauty” and that is precisely what an older man will do for an escort, courtesan or mistress.

by Hannah Jay

For the moment I will divide older men into two groups: 50 and over and the rest. Another day we’ll discuss the young marrieds who need a bit of respite from Saturday night sex and trying not to wake the children. Right now 50+ is the focus.

The great advantage of escort dates with older men is that, for the most part, older men know what they are looking for and what they want when they find her. They are mature, if not wise, and a good deal of the angst which may attend an escort date with a younger man is absent from encounters with men over 50.

At the same time, older men are not likely to see an escort as simply a “service provider” or “sex worker”. They grew up in a world where “hooking-up” was rare and sexual activity, or even the promise of sexual activity, was wrapped up in a lot of moral complications. And the older they are the more likely they are to have complex issues surrounding the very idea of escorts. Not necessarily negative issues; rather a tendency to take the entire transaction as being more transgressive than younger men are likely to see it.

From the escort’s perspective, an older man may be preferable simply because he does see the escort arrangement as more than a little naughty. Coming to a date with this attitude means that it is easier for the escort to exercise the degree of control required for a pleasurable, safe encounter.

For escorts older men are a terrific opportunity to create a stable, generous, clientele. One thing about older men is that they have had longer to make money and, if their children are grown, they have less demands on their wallets than their younger counterparts. For many older men the process of finding, meeting and spending time with an escort is somewhat stressful and for that reason, once they have found a girl they like, they are likely to become a regular simply to avoid the stress of the search.

Some escorts actually specialize in older men indicating in their advertising and on their websites that they “prefer” gentlemen 55+ or that they are only accepting appointments from 50+ clients. I was lucky enough to chat with one a few days ago.

“When I turned thirty I had been escorting for three years and I wanted a change.” Rachel M. explained, “I thought maybe I would start doing therapeutic massage and see a few of my regulars. But I had this wonderful client who was in his early seventies. We’d often go for coffee and then back to my apartment. I told him what I was thinking of and he suggested that I just shift my business to older gentlemen. I did and I have never looked back.”

Rachel is a 34 year old escort working in a mid-western city. She got in touch with me via my website and we’ve been chatting. It goes without saying that Rachel is not her real name. Rachel has a degree in History and has an online business selling vintage clothes and housewares. She’s not married and is very coy about whether she is seeing anyone.

“Three great things about escorting for older men: first, they don’t have anything to prove. They are not going to want to hop into bed at the start of a date and stay there for two hours. Second, they are mainly polite and almost always very generous. My income is nearly double what I was making when I saw younger clients. But the biggest thing is that they are rather sweet and often very grateful.”

Rachel now sees exclusively men over 50 and actually prefers men in their 60’s and 70’s. “I made a few changes in my advertising and on my website. Most importantly, I set my minimum encounter time to an hour and a half and I charged a fair bit more. As my lovely older client told me, men who are retired or semi retired have more time and more money.” said Rachel.

“I also changed the nature of my encounters. I spend more time talking and I like to have them relax in a deep tub. A lot of my clients are quite shy and I find the sort of “spa” experience makes them more comfortable.”

“There is no question about it, older men just love lingerie. When I was doing general escorting I could count on a nice push-up bra to do the trick; but with my older clients stockings, a pretty garter belt, a slip all add to the magic. And they just love to be teased.”

Most of Rachel’s encounter do end up in her bedroom. “I have to say that Vigra and similar drugs makes it all go very smoothly. But I don’t give my clients anything – they need to see their doctor. Once in a while there will be a little performance issue but usually a few naughty words in the right place and we can get the job done.”

“My older clientele really enjoy the fact I work hard to make them feel comfortable and safe. When I was doing regular escorting I didn’t pay much attention to where I was working. With my older clientele I have moved to a nicer apartment – paid for by a lovely man who happens to own the building – and I pay a lot of attention to the little things: the fresh clean towels, the new bar of soap, having some delicious, easy snacks. My clients want to feel pampered and, in return, they pamper me.”

“Remember I mentioned that my older escort clientele love lingerie. Well I have a standing date with a gentleman who completely enjoys taking me to the vintage stores and buying me pretty much anything I like and which fits. I make sure he gets an eyeful when I am trying things on. Another client likes to know I am taking care of myself and he always tips me cash and a day at the spa. I have to tell him which day I am going because he wants his next appointment the day after when I am all buffed and smooth.”

There are a few downsides of course. “The biggest problem is that we are of totally different generations. Which means we don’t have that much in common. At least pop-culture wise. But I’m lucky because most of my clients are well educated and usually successful. We might not be able to talk about the music I like, but we can talk about what is going on in the world or books that they like and think I might like. It works out and I find I am learning a lot.”

The upsides can be huge. “I had one sweet man who was not at all well. Nothing life threatening but he had to spend a couple of weeks in the hospital. I asked if I could visit him – I didn’t want to intrude on his family – and he said he would love a visit. I dressed up and went. He had a private room and, well, I went back twice more during his stay. He got better and came to see me a week later telling me he had something for me. And he did: he arranged the transfer of all his frequent flyer points. “My doctors said I shouldn’t fly.” He had enough that I could go to Italy that summer and Maui in the winter.”

I asked Rachel if she had any advice for an escort who wanted to target the over 50 market. “First off, be a lady. I know it sounds a bit cliché but older men like it when the escort they are hiring does not present as an escort. I actually have one client who wants me to, when he is in the bath, tart myself up so he comes out to find a very sluttish girl waiting for him. It’s a sort of role play thing. But most of my clients like a girl who is fresh, feminine and just a little shy.”

“Second, charge more than the going rate. Way more. Think at least twice as much. Older men have learned that you get what you pay for. If you charge a premium rate they will be pretty sure that you are worth it.”

“The great thing is that if you charge a premium rate you can really spend the time your client wants. When I did regular escorting, on a busy day, I had to keep my eye on the clock. Now I try to book no more than three dates a day and I really prefer two. But my income has gone up.”

“Third thing, and this is important: you have to be sparkling clean, groomed, buffed. So does your apartment. Younger men really want to get down to the action, older men take the time to notice these sorts of things. Their surroundings matter.”

“Final point, be prepared to hear a lot of advice – and I mean a lot. Most of my older escort clients have been very successful businessmen, lawyers, entrepreneurs and they have a lot to say. Most of the advice is pretty solid. Sometimes, though, they sort of switch over to “fatherly” and start digging in on how the escort lifestyle is unhealthy or dangerous or, and this amazes me, immoral. I pay a lot of attention to the business advice, for the fatherly advice I usually thank them but, once in a while, I’ll play the naughty little girl and suggest that Daddy give me a good spanking. Great fun and only one of them has actually spanked me hard enough so it hurt.”

I asked Rachel about how she marketed herself to this older escort client demographic. “Advertising is a great first step. I have a couple of simple ads basically saying “pretty young woman offers companionship to gentlemen 55+”. Nothing more complicated than that. I have two or three pictures – fully clothed – which I use for my ads. The most erotic image in the bunch is a shot of my adjusting a garter tab. But it is gorgeous. On all my ads I have a link to my website.”

“The website is equally simple: a few pictures which I update every couple of months, a description of my services – and a very discreet description it is. My rates and some contact information. Gentlemen of this age like to use the phone rather than email or text which is fine by me. I am a bit strict on the contact information. I don’t take calls from blocked numbers – no escort does – and I am only available on the phone from 10-12 noon and again from 3-4; otherwise email has to do.”

“My escort website does not get all that much traffic (I compare it to my vintage site which gets 100 times more.) but 90% of my clients have got my number there. Other than some very pretty business cards, Rachel M. Online Personal Assistant, that is pretty much all the marketing I do. I stay away from review sites because my ideal client is not a hobbyist.”

“However, truth to tell, I only run my ad a week a month. 80% of my business and 90% of my revenue comes from my regulars. My real marketing is to make sure that they have a wonderful, rewarding, relaxing time when they come to visit me. I encourage them to send me emails or texts when they feel like it and it is discreet and safe for them to do so. I have one lovely man who sends a thank you note on engraved personal stationary every time we meet. Usually enclosing a crisp couple of hundred dollar bills.”

“I also get more than my fair share of referrals. Sadly, a lot of new widowers or gentlemen whose wives have to go into care. There is a little network of my regulars who will slip my card to a friend. And they will tell me they have. I think they are rather proud of the fact they have found me.”

“The one other thing about focusing exclusively on older men is that my own career can go on for years. I’m 34 and by the standards in the escorting business a bit old compared to the 20 year olds coming up; but to a man in his seventies I am practically a school girl, or at least what these gentlemen refer to as a coed. If I stay in shape I can, and probably will, keep escorting until I’m in my late 40’s.”

Rachel makes an excellent point about escorting for the over 50 market – while the competition is intense for regular escorts where youth and beauty are at a premium – building an escort business focused on older men can make it a business which lasts.

“I’ve spent a lot of time thinking about my escort business.” said Rachel. “While I have many regulars, I also had to have the random walk-ins. No matter how carefully you screen, every random was a risk for an escort. Now my business is actually about trust. My older gentlemen are regulars because they trust me. And I trust them. There are no games – well, a few but they are lots of fun.”

“It’s funny, I have gone from being an escort to being something of a friend with benefits to a wonderful group of older men. If I didn’t think it would be awkward I’d have a great Christmas Party for my clients every year.”