Xaviera Hollander - The Happy Hooker - My Own Story

Still I had a lot of fun meeting people, swimming, sunbathing,. and joining the crowd in the afternoons at Fiddler’s Green bar for piñas coladas , gossip, and dinner arrangements.

For the entire three days the pattern was pleasant, but so far I had not met anyone who turned me on, and the hot sun was making me hornier than usual. I realized we were near the Virgin Islands, but this celibacy was ridiculous.

On the last afternoon I met a man named Henry Carter, a nice blond Christian gent from New Hampshire, who had just gotten off the plane and planned to spend a whole week in Puerto Rico. Being half-Jewish myself, I usually prefer Jewish men as straights, but with so many of them around, Henry made a nice change.

He was tall, attractive, intelligent, sensitive, and charming; and after we talked and walked for a while, he invited me to have dinner with him.

That night he took me to romantic Old San Juan, where we ate a delicious Spanish meal, walked through the narrow cobblestoned streets, and stopped in a quaint little bar to listen to flamenco guitar music. Then Henry took me home to his room in Carmen’s guest house, and we made marvelous love, after which he suggested I move into his room and spend the next week with him.

That night I brought my things from the Racquet Club to Carmen’s cozy guest house and fell madly in love with Henry, forgetting all about returning.to New York.

The next week was beautiful. We rented a little Volkswagen and drove all over the island together. We made love whenever and wherever we could. On isolated beaches, in the woods, under trees, everywhere.

Henry’s cock was tremendous and constantly pulsing with desire. We would make love three and four times in a row, and I would want to do for him things I won’t do for every man. I would eat him and swallow his sperm all the way, and I even wanted to have him Greek style, except he was simply too large for that.

After lovemaking we would always talk and laugh and really feel we were in love. It’s the most beautiful thing there is, and it’s a pity it never lasts forever. When you’re fantastically happy, time passes too quickly. Suddenly it was Monday again, and Henry had to leave.

It was time for me to go back also, because it had now been ten days since I impulsively set out for a long weekend, but I wasn’t ready to leave. I liked it in San Juan, I felt good, and I looked good. I was as brown as a little walnut, my hair was streaked gold from the sun, and I was enjoying my life for the first time in months.

Why should I exchange the sea and the sun in San Juan for the cold and the hassle of New York? I could work just as easily here. I was lucky that I was in a profession which allows me employment no matter where I am.

Although I had been straight since I’d been in Puerto Rico, I had noticed all the potential business hanging around the casinos, the beaches, and the bars.

There was only one obstacle. I had never approached a man on my own before, having always worked through a madam, but I figured there couldn’t be anything too difficult about putting together a good sales pitch.

That’s one thing I can do well, actually. No matter what business I’ve been in when I was straight, I’ve always been a good saleswoman, and actress.

So I sadly said good-bye to Henry, and before he went he paid another week’s rent for me at the guest house. We made plans to meet again in New York. He called me twice but somehow we never did get together.

That morning I got into my bikini and went over to the beach in front of the Americana Hotel to relax and think about my plans. I would have liked to leave a respectable amount of time between farewelling my lover and getting down to business, but I had to be practical because I was down to my last few dollars.

I was tossing up whether I should try to make some money that night when luck came my way out of the clear blue sky.

It was Mr. Schwartz, sitting not twenty yards away from me, sunning himself with Mrs. Schwartz. I could tell it was Mrs. Schwartz because they looked identical, the way two people do when they have lived together one hundred years.

I recognized him immediately, much to his distress, and when he saw me striding toward him he turned purple. Three weeks before, in New York, Mr. Schwartz had stiffed me for $150 with a bouncing check, and when I tried to call him up, the telephone number was a phony. It was divine justice that I ran into him now. But as I approached the couple, the craziest thing happened.

Mr. Schwartz, who was about five years younger than God, whispered something hurriedly to Mrs. Schwartz, who is his approximate contemporary, and they both got up and started to jog!

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!”