Xaviera Hollander - The Happy Hooker - My Own Story

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.