The Happy Hooker: My Own Story

by Xaviera Hollander

  They both look like they can hardly cross a road in a high wind, and here they were dashing down a beach in the blazing sun. I started to follow, but then I said, To hell with it; he’s staying at the Americana, so he has to come back this way if he doesn’t drop dead in the meantime.

  Now, there is one thing I would rather not do, and that is to embarrass a man in front of his wife. I would never be indiscreet. But if someone deliberately cheats me, then I have no scruples. So I just stood there biding my time, and eventually Mr. Schwartz returned, flushed and puffing, and he looked like a toad.

  “Mr. Toad, uh, Mr. Schwartz?” I said, and stepped casually in front of him. He couldn’t find his voice and wished he were invisible.

  “Aren’t you Mr. Schwartz?”

  He nodded his head as if to say “Yeah” and got rid of Mrs. Schwartz with the same whispering expertise he used to make her jog down the beach. She was obviously curious, but I’m sure she didn’t suspect I was a hooker, because I don’t look like one at all.

  “Mr. Schwartz,” I said, “I would appreciate it if you would give me cash money within the next fifteen minutes, because your check bounced on me.

  “If not, it will be the easiest thing in the world to check your room number and tell your wife who I am and what you have done with me.

  “Plus, I suggest you should not give phony checks or telephone numbers to girls anymore.”

  He hurried away and came right back with my $150, and I feel sure it will be a long time before he visits a brothel without something more than his cock in his hand.

  So, you see, sometimes a man is forced to be honest by accident; otherwise they would fool you out of a lot of your money. I have been cheated out of so much money it’s unbelievable, but that is another story in another chapter.

  The next night I made my first professional appearance in the casino to scoop up some of that big bread, but first there were a few things I had to learn about hustling in a place like that.

  The first rule to observe is never be too obvious in what you’re doing. With big money like that at stake, the house doesn’t want some little hustler taking away a high roller who is on either a winning or a losing streak.

  If he’s winning big, the house will object because they want the chance to win some back.

  If he’s losing and you say to him, “Why continue to lose money on the table, come with me and have some fun,” they also react, because you’re taking away potential revenue. So either way you have to be cool.

  The second rule is don’t interrupt a man when he is on his roll. He is likely to be brusque and ask you to go away. Gamblers are known to be very superstitious.

  Wait until he is definitely through, and then go in.

  I made some mistakes, understandably, on the first night, but after that I quickly learned how to operate. To begin with, I walked in wearing one of those see-through dresses, very transparent, very sexy and revealing, and the whole room noticed me and went grrrrowl.

  The women, most of all, said, “Look at that, wow, she has nothing underneath, not even underpants!”

  Next thing I knew I was taken out like a little pussycat: “Lady, would you please remove yourself from the premises,” Carlos, the pit boss, said.

  I didn’t know they were so strict in their rules of dress. Catholic squares! So I made it with Carlos, and that saved my head, but he warned me: “Xaviera, please try not to be so conspicuous in the future.”

  I came back again fully dressed, wearing no makeup, just a little eye shadow and lip gloss, and making, I believed, a clean, fresh impression. I also behaved conservatively, but by now the men were watching me like wolves.

  I picked out a man who was playing with $100 and $50 chips who had no woman beside him, and he was my target. I stood back, caught his eye, and gave him a suggestive smile and a sexy look, and he noticed me.

  Then I worked my way in beside him, and at the first opportunity, asked him to teach me a few gambling rules.

  “Wait just a while,” he said, “and we’ll go have a drink at the bar, and I’ll explain them to you.”

  When he was through we went to the bar, chatted awhile, and I said, “I guess you’re here with your wife?”

  “No, I’m here alone,” he said, “so why don’t we go up to my room and discuss the rules of gambling?”

  In the first week or two I took my prospects to the bar, gave them a little sales talk, changing it each day to add something nice and personal about each man. I also usually gave them the story that I was a secretary from the United Nations in Puerto Rico on vacation and trying to earn just $50 to pay for my hotel room. Telling a man that kind of story makes him feel he is not a john.

  However, if the man asked me to stay over in his room for the night, I said, “I would love to, but you will definitely have to raise the fee to $100.”

  But I never asked for cash “up front,” because that strikes me as too whorish.

  As my action accelerated, I dropped the bar and the corny story about the rules of gambling or being a secretary on vacation, because it was all too time-consuming. Instead I developed a smooth, nonchalant way of shopping the men with an arrogant look and a subtle shake of the head – left to right, yes or no – and we got straight on to business. Most men are happy to do that and get back to the tables, and pretty soon I was well established, making $200 a day, plus I had tons of time left to relax on the beach and do my own private thing.

  My daily routine usually was as follows: In the morning I went to the beach, found a canvas chair, sunbathed, swam, and fooled around with some young kid.

  That’s one of my hang-ups. I love to seduce young boys around seventeen, or nineteen at the most. Most Jewish boys are in Puerto Rico with their parents, so I have to come on like a big-sister type so as not to arouse their suspicions. I take them into the water or for a beach walk, then drag them back to my room like a lioness stalking her prey.

  Being naturally always horny, I usually give them a free blow-job straight away; then I screw their pants off.

  While I was living with my fiancé, I got so used to sex at least once a day that even though it is now my profession, I still enjoy straight fucking as long as the people are nice.

  Usually these young boys climax one-two-three, so I take my time on the second time around to teach them how to control themselves, how to please a woman, the different variations, how to caress her, kiss her, suck her, and not to be too rough, but nice and gentle.

  So in the early afternoon I would usually give away all my freebies to the young kids, then send them back to their families.

  If I may be immodest for a minute, I will estimate that 25 percent of all Jewish youths who vacationed in Puerto Rico between February and April, 1970, were taught the art of love by me. A few fathers, customers who thought I was just a horny college girl paying her way with favors, even chipped in and paid me to educate their sons.

  Around four P.M., when the sun was no longer strong and the bars were closing for siesta, I would set out to turn two tricks. My daytime working area was around the lobby of the Americana or the El San Juan Hotel, where I would stand outside the bar or the drugstore and approach a likely-looking customer on the spot.

  If the man’s wife was out shopping or getting her hair done, we would go up to his room, and I would blow him, fuck him, boom, boom, fifteen minutes, $50, and out.

  If their wives were around, they would usually give me their card and say: “I can’t do anything here, but call me in New York.”

  Occasionally I would hand them my card, but as a rule that is a dangerous practice, because their wives could discover it in their pockets. In New York, card-passing is acceptable because prostitutes disguise their professions by printing on them activities like objets d’art, management consultants, or, in my case, interior designer. However, others are more obvious, and if a sharp wife finds a card in her husband’s pocket with one of the following occupations – headmistress, erection and demolition expert,
public relations, or even manual laborer – she can usually assume the only thing getting made is himself.

  After two customers, I would go back to the guest house, take a siesta until around ten P.M., bathe, dress, and have a bite to eat at the Lemon Tree in the El San Juan before setting out for my night’s work. My target was four customers a day – two in the afternoon and two at night – because I wanted some time to myself, and frankly, could not easily handle any more on my own.

  However, I was obliged to make an exception in certain cases. There was the time the group of eight New Jersey Italians vacationed in San Juan for a week, and all kept wanting to get laid at once.

  They would send their wives out shopping around ten in the morning and take me to their cabana at the Americana and screw me one by one while somebody watched the door to make sure the women did not return and catch them.

  They would be laughing and joking and turning on to the outrageousness of the scene as much as to getting laid.

  Once this same horny group arranged to meet me on the beach at midnight while their wives were all occupied at the tables playing roulette or blackjack.

  It was a beautiful, idyllic setting under the stars with a warm breeze blowing and the waves gently crashing in the background, but the lovemaking was far from romantic.

  As they stood in line laughing and unzipping their pants, I gave them each a blow-job on the sand. I was blowing and spitting and blowing again and wishing I had my bottle of Scope with me, or at least a water fountain to rinse my mouth out, because the taste of sperm really turns me off, and that night it almost made me vomit.

  I am used to a more sophisticated way of operating, but these guys didn’t care about white sheets, only about getting their rocks off before their wives discovered they were missing.

  I had my panties off while I was kneeling down on the beach blowing them, and the mosquitoes started biting my bare bottom. Then the guard dog from the hotel came barking around, followed by the night watchman, who threw a flashlight beam on us and ran away, shocked.

  Altogether, it was a complicated and uncomfortable way of conducting business on both sides, so I settled for a ten-dollar reduction per man on a package deal for the group of eight.

  Business was booming, and I was making a fortune, but Carmen’s Guest House was becoming an inconvenient place to stay. Apart from the fact that it was too far removed from the action, I suspected they were starting to figure out just what my activity was, and in a little place like that, word soon gets around. So I started thinking about moving out of there.

  A few days later I met a young man on the beach named David, who was around twenty-eight, much older than my usual freebie. He approached me, for a change, and asked me would I like to go for a row on his little rubber raft.

  The funny thing was that on that day I had an invitation to go sailing on a huge luxury yacht, but David’s suggestion, appealed to me more.

  We paddled a long way out to sea, talking and laughing and falling into the water and scrambling back on board, and as I hung on to his strong sunburned shoulders, I started to get really turned on.

  He wasn’t good-looking, but he had a sexy Jean-Paul Belmondo kind of face, arid he also had a big Jewish nose. There’s a saying in German – “An dem Nasen eines Mannes erkennt man sein Johannes” – which means you can guess the size of a man’s penis by the size of his nose.

  I also believe you can tell from his hands. If he has long, slim fingers, he usually has a long, slim cock. If he has short, thick fingers, he usually has a short, thick cock, and if he has meaty, fleshy hands like a butcher, he usually has a flabby, fleshy cock.

  I take the liberty of making these generalizations because I have seen enough cocks in my time to consider myself an expert on the subject.

  After paddling around for a while, David and I came back ashore, left the raft in the shade to dry out, and went to the hotel’s outdoor bar for a piña colada and a fruit punch, my favorite drink. There we met his roommates, Ricky, Hood, and Brian, and together we spent the rest of the afternoon running around the beach, talking, and, of course, getting around to the topic of sex.

  The boys, aged between twenty-eight and thirty-two, complained how square the vacationing New York girls were and how innocent and stupid. “What we need for us is a woman like you,” David said, to which the others all agreed. When one of them suggested I move into their guest house, I jumped at the idea.

  Why not? Their place was close by the beach and the action, and what more could I want than four strong, horny young men to play with in my free time?

  We all walked over to the little white two-story clapboard house, where we found the landlady, a dear old German grandmother type, in the garden watering her plants.

  I approached her in German requesting a room, and she was so charmed and flattered that she said I could have the best room, on the boys’ floor, with airconditioning and a bathroom all to myself. The guest house was modest, but clean and unbelievably cheap for Puerto Rico, only $10 a day.

  “Okay, I’ll move in,” I told the boys. “So let’s go over to Carmen’s and get my belongings.”

  When the boys brought me back with my luggage, which had increased since I arrived in Puerto Rico, they went to their own room to freshen and relax, and I went to mine down the hall to unpack.

  Half an hour later I went to their room, which was very big and had several single beds in it, and I found them all fresh out of the shower with towels around them, all except David, who was walking around naked, proving my theory about big noses.

  There was the smell of grass in the room, and they were lazily smoking, and the sound of rock music was roaring in the background, and soon somebody suggested we have an orgy to celebrate my arrival.

  Nobody needed much persuasion, and pretty soon we were all stripped naked, tangled on the floor between the beds sucking, fucking, blowing, laughing, and climaxing. It was an unbelievably beautiful scene. Our bodies were hot and perspiring because there was no air-conditioning in their room, so we showered and did it all again.

  Caught up in the abandon of the whole scene, I forgot my resolution never to allow compromising photos to be taken of me.

  We took out the Polaroid camera to make some pictures, one of which was an absolute masterpiece. The Tourist Bureau should have used it on a scene card. It was a picture of me wearing David’s Spanish matador hat, sitting on his cock on the floor while Ricky was standing on my right getting a blow-job and, Brian to my left getting a hand-job.

  Hood, the one who took the pictures, had never been in a group scene before, and he was so bashful he could not get it up, so I had to fuck him privately in my room later on.

  As we jumped around and carried on, I started to get a sneaking feeling that somehow we were being watched. Nobody else seemed to notice, but they were so whacked out of their heads on grass that they couldn’t care less if we were on Candid Camera.

  But I couldn’t shake the feeling there was someone observing our scene, and as I looked toward the window that led onto the veranda, I saw the venetian-blind slats almost imperceptibly move.

  Without being obvious and not saying a word, I casually climbed off David’s cock and walked to the bureau under the window, pretending to get something in a drawer.

  When my hand was out of eye range, I took hold of the blind cord and yanked it open, and there, staring me in the face, were the startled eyes of the landlady’s forty-five-year-old spinster daughter. Her peroxide-blond hair was all matted in the perspiration on her forehead and she was blushing and flushing and was very embarrassed indeed.

  “Madam,” I said to her, “would you please keep your nose out of private parties unless you are invited? Furthermore, I would be grateful if you do not shock the sweet old landlady by telling her what you have seen.”

  Without saying a word, she hurried away along the veranda, and we all cracked up laughing. And that, more or less, was the reckless tone of my next few weeks with the band of va
gabonds.

  The boys were on “extended” vacation in Puerto Rico, living the best way they could, which was not always something their parents would approve of if they knew. They were all law-school graduates, except David, the dropout, who was a larcenist by nature and the biggest, horniest fuck of all.

  But Hood was the one I liked the best emotionally. He was sensitive, intelligent, and from an aristocratic New Jersey family. Together we all lived like beach bums, wildly and sometimes childishly, but it was a good balance for the work I was doing twice daily.

  In the mornings we would all go to the beach, pinch some chairs, fool around, then around four P.M. I would leave for my afternoon’s business and join the boys back at the house later for a relaxing orgy and a siesta.

  If the landlady’s nosy daughter was still interested in our activities, she no longer showed it, and always made a point of darting out of sight whenever my band of “freak hippies” walked by.

  However, one morning when I broke our regular routine of being absent from the house all day and ducked back to pick up my suntan lotion, I discovered that I was wrong.

  As I climbed the wooden stairs, I could see the sandaled feet of the spinster daughter standing motionless beside my bed. “Oh, my God,” I thought, “the busybody old snoop has found our orgy pictures.” Then I remembered she had seen the live performance, so what the hell, let her have her kicks as long as the dear old landlady was not exposed to it.

  But as I tiptoed barefoot into the room, I saw none other than the old lady herself holding our pictures up to the light and discussing our various positions as though she and her daughter were Masters and Johnson!

  They were both so absorbed in the pornography that they didn’t hear me enter at first.

  “Good morning, ladies,” I said., “Are you enjoying our happy snaps?”

  They wheeled around, mouths open, dropped the pictures like hot coals into the open drawer, and slammed it shut.

  “Madam,” I addressed myself to the daughter, “it is not enough that you snoop around things that don’t concern you, but you have to get an innocent old lady involved, too. You should be ashamed of yourself, you really should.”