Ten male prostitutes give you tips on…
How to Make Love to A Woman (Like a Gigolo)
During law school, I used to play tennis twice a week with a friend named Roger from Columbus, Ohio. The one thing that always surprised me about him — aside from his great backhand — was how much money he seemed to have. While I was usually strapped for cash, he couldn’t seem to spend it fast enough. All I could do was make tuition payments. Roger, one the other hand, dressed well, drove a Porsche, and always had a beautiful woman on his arm.
I had no reason to assume he was privately wealthy, and as far as I knew, he didn’t have a part-time job. The great mystery of those days was: where did Roger’s money come from? One night, in the middle of second-year exams, I found out.
It was about two in the morning and we’d been going over cases since the previous morning. When we finally called it quits, we adjourned to a local bar. Maybe the exam pressure was getting to him. Maybe he wanted to titillate or impress me. Maybe he just needed to get it off his chest.
Whatever the reason, Roger announced over scotch on the rocks that he did have a part-time job. He was paying his way through law school by selling himself. Roger was a gigolo.
I’d never thought much about gigolos before. I guess I’d assumed they drove Corvettes, wore gold chains and silk shirts, slicked their hair, and reeked of cheap cologne. I didn’t picture them going to law school, or playing tennis — or coming from Columbus, Ohio.
“I never thought gigolos were for real,” I said. “You see streetwalkers any day of the week, but gigolos aren’t visible. At least, you don’t know they’re gigolos.”
“Gigolos aren’t really the same as female prostitutes,” said Roger. “Women are looking for different things from sex than men are. A man will go out and buy sex for a night. A woman would rather ‘keep’ a man. She might start paying his bills, taking care of him — he’ll start paying her back with sex. Of course, there are gigolos who serve women on a one-time basis, but most of them are really just kept men.”
When I finally recovered from his announcement, I was consumed with curiosity. How long? How often? How much? But most of all, why?
“I got into the ‘profession’ sort of by chance,” Roger told me. “It started with one of the women partners at the law firm where I worked as a law clerk last summer. About forty-five, honey-colored hair. You know, sexy. I’ve always had a thing for older women.
“We worked late one night and she invited me to dinner. We drank two bottles of wine, she invited me back to her apartment, one thing led to another, and we ended up breaking the basic rule of good office politics. When I got home the next morning, I found three hundred-dollar bills in my pants pocket. Before too long she introduced me to a few of her friends. I had a fancier client list than the firm.”
Why?
“Obviously, the money’s terrific. I mean, even lawyers don’t make that much. But the money wouldn’t be enough if it didn’t make me feel so good. That’s right, it makes me feel good.”
“Most of these women are really unhappy. They’re married to stiffs. They’re never really satisfied — sexually, I mean. They come to me for that satisfaction: the attention, the affection, you know, all that stuff that they can’t find anywhere else. I get off on that.”
Roger is still a friend. But his profession has changed. He’s now practicing law in Chicago. Last time I talked to him he said, “We just had our third child.” Roger’s been happily married to the same woman for six years.
Roger’s story led me to other men who make their living in the same line of work. What was it like to give women pleasure as a profession? I wanted to know. Was there anything to learn from gigolos about making love?
“A woman may have the exact same fantasy every night for ten years and still be ashamed to say something to her husband about it. That’s when they call my agency.”
A very successful twenty-five-year-old “callboy” in Chicago told me, “The real trick is to make a woman feel good about herself. When a woman comes to me, I try to make her feel like the most beautiful, the sexiest woman in the world. Some of my clients are getting on in years-twenty, thirty, even forty years older than me. That can be pretty awkward, especially in bed. But after a few minutes, I get them relaxed, feeling special. That’s the way they want to feel. And the less attractive they are, the more they want to feel that way.
“I start out with something nice and simple, something like ‘You smell terrific,’ or ‘Your nipples are really beautiful.’ Pretty soon I can get into something a little heavier. I tell her, ‘This really turns me on.’ ‘You’re lovely.’ ‘I don’t want this to stop.’ That sort of stuff. It puts her at ease, makes her relax. It can be a long night if she stays uptight.
“At first she probably doesn’t really believe me. She’s saying to herself, ‘Oh, it’s just for the money.’ You can see that on her face. But after a while I can usually get her to enjoy herself. Sooner or later, these women let themselves believe me because they really want to believe me.
“Sometimes, even I believe me. In fact, most of the time, I can really get into it. You know, it’s not just an act anymore. Suddenly I do think she’s beautiful. I really like being with women. I enjoy their company. I like just talking, spending time with them. I bet that’s one reason women find me sexy — because I’m really into them, in a lot of ways.
Sean, one of New York City’s most sought-after and well-paid professionals, works for an agency and specializes in fulfilling women’s fantasies.
“You wouldn’t believe what some women think about when they’re having sex,” Sean told me. “The person who’s down there [pointing between his legs) is almost never the person who’s up here [pointing to his head]. A husband or lover is down there, but up here is some college professor she had, some soap-opera hero, a famous jock. It’s usually the same fantasy over and over, with maybe one or two little things different; it becomes a habit. And she has to think about it to get an orgasm.”
I asked him for some examples.
“Domination fantasies are big. You know, some guy she saw on the street or the tube that day shows up in her bedroom late at night when she’s alone. He rips her clothes off, maybe ties her to the bed, forces her to give him a blowjob and call him ‘sir,’ makes her beg for more. That’s pretty standard.”
“A woman may have the exact same fantasy every night for ten years and still be ashamed to say something to her husband about it. She’s afraid he wouldn’t approve. I don’t know, maybe they’re right. But if I were them, I’d go ahead and tell him, then ask him to join in the fun. If he’s not willing, if he really doesn’t approve — well, that’s a different problem.”
“That’s when they call my agency. The agency gets the whole story, details and all, and passes it on to me so I know what to do, what part I’m supposed to play. One of the advantages of working for an agency is that a client isn’t afraid of me. She knows I’m not some sort of weirdo. She also knows I won’t think she’s some kind of weirdo, I won’t laugh at the wrong time. After all, I do this for a living. She figures I must have seen weirder things in my work — and I usually have.”
“I don’t think most people really understand what it means to someone to finally live out a fantasy like that, one that’s been bugging them every night for thirty years. It’s a real kick for me just seeing the pleasure it gives them. Sometimes it’s a once-in-a-lifetime thing.”
I asked Sean if any fantasy was particularly memorable.
He hesitated. “There was this lady who had this fantasy about being a college cheerleader. In her fantasy, she waits around after a game for two or three of the players. They come out and surprise her in some dark corner near the field. They haven’t showered and they’re still wearing their grimy, sweaty uniforms.”
“She really had the details down. She must have gone over it a thousand times in her head. She isn’t wearing panties. She lifts her skirt, and one by one they go down on her while she’s standing there. Then — she’s still got her cheerleader’s outfit on, and they’re still in their uniforms — she has sex with them, one right after the other. And while she’s having intercourse with one of them, she’s giving one a blowjob and the other a handjob. It was quite a scene.”
“The agency really handled that one. They told three of us not to shower during the day, they got us these old football uniforms, and that night in her hotel, we went through the whole fantasy, step by step. It was a blast.”
“I’m sure that night cost her a bundle. She was probably a little embarrassed at first. And we got stares walking though the lobby in football uniforms. But what the hell. That was probably the best night of that woman’s life. It was a kick being part of it.”
“When people figure out that I’m a kept man, they just assume I’m really hung,” said Larry, who lives in a luxurious hotel suite in Atlanta, which is provided by an aging widow of considerable wealth. “Sex is my stock in trade, right? I’ll let you in on a secret: I’m not. I’m a little under five inches, erect, which means I’m a little under average.”
“But a lot of men who are well-endowed are lousy lovers. They don’t take their time. Talk about slam-bam. They take it for granted the woman will find everything they do terrific. They don’t know a large penis can hurt a woman sometimes, especially if she isn’t ready for it.”
“Sure, some women like men with big dicks. But I think that’s an exception, not a rule. But I know for sure, I mean from my own experience, that a small penis can turn a woman on just as much as a big one, if you know how to use it. A man who’s small has to make up for it with a lot of foreplay — use your hands, your tongue. A lot of women don’t come during intercourse anyway.”
“I won’t say it’s an advantage. When women see me for the first time without my clothes, they’re a little disappointed. But not for long.”
A beefy, blond, and tanned Los Angeles gigolo who occasionally walks around in the background of shows like Love Boat and Dukes of Hazzard told me that his current lady, a film star of the forties, doesn’t really want to have sex very often. “Sex puts her off sometimes,” he said. “Most of the time, she wants to put her head on my shoulder. She wants me to hold her. She knows the sex is there if she wants it. I do whatever she wants. That’s been clear from the start. But that seems to be enough — just having me there. I’ve spent the whole night just holding her. That’s not bad. It can make sex better when you finally have it.”
I asked a thirty-two-year-old gigolo in New York named Jim if there was anything unusual that his lady friends particularly enjoyed — any “trade secrets.”
He thought for a while, then said, “A lot of women like it when I ease my finger up their asses just before they come. It makes them go wild!”
Did his clients ever request anal intercourse?
“Yeah, some. About one out of four, maybe.”
How did he know when they wanted it?
“It’s usually pretty easy. They lift their hips off the bed.”
Aren’t they afraid it will hurt?
“Yeah, if they’ve never done it before. But if you do it real gentle, it shouldn’t hurt too much, especially if you’re relaxed. You have to be relaxed. That means you don’t do it right away; you can only do it after you’ve been making love for a while and you both feel real comfortable. Besides, most women don’t mind a little pain, as long as there isn’t too much.”
If a woman wants to have anal sex, Jim begins by lubricating the area with saliva. A shower beforehand, he said, can take care of any “aesthetic” problems. Then he lubricates the area thoroughly with Vaseline, which is hard to clean off but preferable to water-soluble lubricants, such as K-Y jelly, because they tend to dry out too quickly.
When the area is well lubricated, Jim suggests massaging it with one finger, slowly inserting it in the anus. At first the sphincter muscle will tighten involuntarily. You should stop penetrating any further, he says, until the sphincter has adjusted to your finger. Once the finger has reached the rectum the resistance will lessen dramatically.
Then, to widen the opening gradually, Jim inserts a second finger. Only when the woman’s completely relaxed does he lubricate his erect penis with still more Vaseline and insert it — slowly and carefully at first, ready to withdraw it if the pain becomes too intense for her. When he’s completely inside, he pauses a moment so she can get adjusted. Then he begins thrusting — slowly at first, picking up speed when he’s certain she’s completely comfortable.
Jim said it’s possible to perform anal intercourse in several positions. “The nicest is when she’s lying on her back with her legs over your shoulders. That way you can kiss. But if it’s her first time, and she’s afraid you may hurt her, you can try lying on your back and have her sit on top of you, guiding your penis in herself. In fact, if it’s her first time, the easiest position is probably side to side — you know, like two spoons. That seems to cause the least pain.”
Jim didn’t add — but I will — that you should always wash up before reinserting either your finger or your penis in either her vagina or her mouth. Otherwise serious medical problems can result.
Rick is an in-demand New York gigolo who spent two years as a shortstop on a major-league baseball team and still has the manner and physique of a professional athlete. Unlike his colleague Sean, when Rick is sure a woman wants it, he tries to leave the directions up to her. “I just tell her that I’m at her disposal,” he says. “What makes me happy is anything that makes her happy.”
“At first, some women don’t want to give orders. But after a while they get used to it. If they didn’t have some desire to control things, they wouldn’t be paying for it in the first place. The power is a real turn-on for most of them — something they haven’t gotten very often in sex. The idea of having me there, ready to do anything they want, or anything to me — they really get off on that. If they want it, I even play the slave role.”
What kinds of things do the women ask him to do?
“Just about every woman wants cunnilingus. From what I can tell, there aren’t very many men out there who are into oral sex. Women love it, but they don’t seem to get it much. I think that’s what most women come to me for.”
Probably the least expected advice came from a man in Palm Beach who has the accent and looks of the Latino stars of the fifties. “You must know when to let her take over,” he told me. “A lot of people think I am a big success because I let her lie back and I do everything. It isn’t that way at all. It’s just the opposite for me. I’m a big success as a male prostitute because I let her do it to me. They like that much better. You have to pick that up quickly, be on your toes. If you push when she wants to push, you have a very unhappy lover.”
“Of course, you have to be ready if she wants you to take over. If I think she wants it, I always ask her to let me give the orders. I tell her to use her mouth, or to do this or that with her tongue, things like that. Believe me, I let her know how much pleasure she gives me. I tell her many times how good she is to me.”
A paid lover in Chicago told me about his specialty: “Massage. That’s what I do best. And that’s what my clients always ask for. I don’t mean regular massage — the kind of thing they can get at some beauty place. I mean a sexual massage.”
I asked him what the difference was.
“A sexual massage is a massage that leads to the erogenous zones but stops short of sex.”
Intrigued, I asked for a description.
“Well, I usually use some oil. I like vegetable oil better than baby oil; it isn’t absorbed in the skin so quickly. My favorites are almond oil, avocado oil, or olive oil. You make them smell better if you add some drops of scent. I use a little of my cologne, so the oil smells like me. Women are big on smells. That way she’ll remember me and what I did for her.”
“Sometimes, I heat the oil a little. But you’ve got to be real careful not to heat it too much — you can burn yourself. I always test it by putting a few drops on my wrist before spreading any on her body.”
“When you start massaging, don’t stop. Even for a minute. If you want to put some more oil on your hands, stay there, lying next to her. Put your leg on hers, or something. Anything so the contact isn’t interrupted. Once you’ve taken your hands off, the spell is broken.”
“I work in three stages. The first stage is the non-erogenous zones. You know, the back of the neck, the calves, the small of the back. I work them real well.”
“Then I turn to the places that aren’t really erogenous, but they’re pretty close. Like the stomach, the buttocks, the inner thighs, the ears, the insides of the elbows, the insides of the knees.”
“Finally I turn to the erogenous zones, especially the breasts, the nipples, the vagina. I still think of it as a massage. That’s important, because that way she can get aroused without getting too aroused — at least, not yet anyway.”
I asked about some techniques.
“For the nipples, you should put your two thumbs together in a line, with one nipple in between. Then push the thumbs in opposite directions. Keep on doing that in different positions, around and around the nipple. Believe me, she’ll like it.”
“With the vagina, I also do something special. If her vagina isn’t naturally lubricated, you begin by lubricating your hands. The first thing I do is press the tips of my thumbs against that spot between the vagina and the anus. That, by itself, feels really good.”
“Then I push my thumbs in a straight line right up to the inner lips. Then I separate the thumbs, brushing them outward across the outer lips. I bring them back to the inner lips, then back to the spot below the vagina. I repeat that until she’s so turned on she can’t take it anymore. That’s when the massage ends and the main act begins.”
“If there’s anything a woman likes,” said a thirty-five-year-old man in Los Angeles who has been kept by a series of women since he was eighteen, “it’s staying power. Especially if she can have multiple orgasms, she can only have them if you can keep erect long enough to give them to her, and sometimes that means twenty, thirty minutes or more. Now, it’s difficult to stay hard that long without coming. But I’ve learned how to do it.”
“The way you do it is you have some multiple orgasms of your own. Most men don’t realize coming isn’t the same thing as orgasm. Orgasm is that throbbing feeling you get when you come — when you ejaculate — but you don’t have to come to have that throbbing feeling. You can get it three, four, five, or even more times before you come. In fact, you can probably get it even more than that, but after three or four I don’t think you get the same pleasure from the orgasm when you finally do come.”
“So it’s great for her, because I can keep it up longer, a lot longer. And it’s great for me, because I get a lot more pleasure of my own out of it.”
How does a man achieve these multiple orgasms?
“I do it two ways. One is by thinking about something else, something that isn’t sexy, just when I feel I’m about to come. Thinking about the World Series always works for me. Sometimes I do it by letting go of the pressure on my bladder. It’s like when you need to take a whiz, you can put some pressure on your bladder to hold it in. Well, if you let up on that pressure when you’re about to come, you won’t come. It sounds harder than it is. It’s a cinch with a little practice.”
My friend Roger has the final word of advice: “Everything I did was geared toward making a woman feel appreciated — that I’d make love to her with or without pay. Women used to offer me a tip at the end of the evening, and I always refused. I’d say something like, ‘No, it was my pleasure.’”
“I wanted her to think that there wasn’t anyone I would have preferred to spend the night with. After I left, I wanted her to remember it as a real exchange of affection, not just a financial transaction.”
The advice from all these American gigolos can be summed up in a single phrase: to satisfy a woman, you’ve got to make her feel loved — even if she’s not.
If they can do it for hire, it should be easy for love.
It could have something to do with your age, but more than one of us found ourselves humming “Just a Gigolo” by David Lee Roth while perusing this article. (Apparently he started painting when we were not paying attention.) While that may not speak particularly well of our more erudite qualifications for the vaunted position at Penthouse we hold, it does show how much pop culture can invade your brain even much later in life. You young people out there take heed. Some day you will find yourself trying to explain WAP to your grandchildren. Won’t THAT be fun? … You might think about the 2019 Tips if you need to distract yourself now.
