A Weekend in the Hamptons

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Before I tell you why I was fucking a very pregnant Sonja in the Hamptons on that cold gray day I should tell you how the summer ended and what happened next:

Shortly after starting school in September, Cindy had split up with me, ending our summer romance. I learned from her mother that Cindy was reunited with her husband. We coupled for the last time on her boat the weekend before school started and ended things without saying goodbye. A week later she broke up with me by text. Then her mother let me know that our affair would end as well. First I had to do something for her.

"What?" I said.

"One of my sisters wants a date with you. You will be paid."

"And if I say no you'll make my life hell?"

Sonja nodded. "It's good money. For you."

"I love you," I said. "I want to keep seeing you."

"Be at this address at two on Saturday," she said handing me a card.

I looked at it. Central Park West. Tenth floor. I think I gulped.

"Don't worry," Sonja said, "it's completely discreet. No one will bother you. Wear something nice. Give this card to the doorman. His tip is already arranged. Everything's set."

In the elevator, I saw immediately that tenth was the top floor. Penthouse territory. When I rang the bell at two, a tall tan woman answered. I recognized her immediately. It seemed ironic that I already knew what she looked like naked, having watched her swim and sunbathe nude on a Hamptons beach all summer, the last time just the week before. And she knew what I looked like in swim trunks on Derek's beach. I also knew some her story from Cindy. Thrice divorced, Aunt Tally (short for Talitha) worked in the fashion industry, but her fortune came from her first marriage. At forty-six, she was the oldest of the sisters, but slender and beautiful.

Once the door closed behind me, she smiled, introduced herself and offered me a drink. Her sumptuous garden penthouse overlooked the park. We chatted on the couch for a few minutes, then she took my drink, put it on the coffee table and moved in for a kiss. Satisfied, after a few minutes she got up and walked away.

"Follow me," she said.

I thought her bedroom surprisingly small until I realized it wasn't her bedroom, but a guest room. When she started to undress, I did as well.

"I'll do that," she said, moving in, sweeping off my suit jacket then undoing the knot of my tie. I ran hands over her back and shoulders and began undoing her buttons down the front, making lots of eye contact. I began kissing her as we undressed each other. She did not resist.

We did it on the bed, she on top for most of the hour except when we rested in between. Her fake boobs were much more realistic, having enhanced her to a C, unlike the ridiculous DD's Sonja had installed. When Tally tired of being on top, I did her from behind in a spoon, then doggy style, then face to face with her calves around my neck. She squealed in delight. I filled two condoms. I don't know why she turned me on so much until I realized she was a forty-something version of Cindy with breast implants. I also knew that she was the one who saw Cindy riding me that night in the pool house. Cindy told me. Aunt Tally had seen me naked, too... and in action.

Money was delivered by courier the next day. A thousand in cash. I hadn't expected that much. I hadn't expected anything, really, except to be finished with the Baldwins.

I was wrong.

Two days later I received a text from Sonja. I met her at a wine bar hoping she wanted to continue our affair, but discovered her other sister wanted a date. I went to her apartment at two the next day and we shagged for an hour. At forty, she was closest in age to Sonja and only a little taller, but had enhanced to a D cup, which was one size too big. On top only once, she preferred it from behind. The one time on her back with me between her legs, she liked to kiss extensively. Before I left, she claimed to be the one who saw Cindy and I in the pool house that night.

Again, the money arrived the next day. A thousand dollars. I wondered what Sonja's cut was, if any. Would she even deal with such small amounts of money? Then I remembered: this was about power, not money.

A day later Sonja messaged me again. Her third sister wanted a date that weekend. Still married, arrangements were made to meet at the Ritz. Forty-three, she looked the most like Sonja, but had only enhanced to a C cup, which looked good on her. Her thing was oral sex, giving and receiving, but liked to be shagged from behind, which we did several times. She also claimed to be the one who saw Cindy and I in the pool house.

Next day? Another thousand arrived by courier. In a week I had pocketed three grand. Sonja didn't return any of my calls or messages the following week. I decided it was finally over. I should have been relieved to be out of her clutches, but I missed her. Busy with classes and schoolwork, I had little time to think about it.

When does a man realize he's a gigolo? When he's set up with a complete stranger. Fine, the Baldwin sisters all wanted a crack at me. At least I knew them, sort of. But when Sonja called the following week for a date with someone I had never met I realized not only I was a prostitute, but that she was pimping me. It's funny, really, because I'm not a good-looking man. I've always considered myself average, nowhere near the male models and pretty boys who play gigolos in movies, TV and real life. I work out twice a week and run everyday, but am not a hunk. Or at least I never thought so. At six-four and two hundred, I am quite sturdy, but not heavily muscled. Both Cindy and her mother liked to say I had a swimmer's body. Come to think of it, Derek once said the same thing.

I don't know why I agreed. Some of it was fear of Sonja, some just plain curiosity. Truth was I had become sexually arrogant. Fucking Rosa, Cindy and Sonja all summer gave me a swagger that I was some kind of hot stud women desired. I wanted to do it. I wanted to fuck every woman Sonja pimped me to.

What I didn't realize at the time was that the Baldwin sisters had extensive social contacts in the city and had created a buzz about me. The only good thing? They were all stinking rich. Most were middle-aged ex-wives of wealthy, powerful men who had divorced them for younger women. Cast off starter wives. My legend grew by word of mouth. None were younger than thirty or older than fifty. Most, like the Baldwins, were in their mid-thirties to mid-forties. Truth is, I enjoyed fucking every one of them.

My first date was still married, the wife of a prominent surgeon. My second date was heiress to a manufacturing fortune. My third date was the ex of a Broadway producer. My fourth date was British and, of all things, a minor Royal. My tenth was the ex of a Hollywood actor. My twentieth was/is so famous I cannot say what she does or it'd give her away. During all this, each of the Baldwin sisters saw me multiple times again. As my client list grew, so did the money. Fifteen hundred, two thousand, even twenty-five hundred a pop came my way, plus tip. The more my price went up, the more in demand I became. Sonja worked around my school schedule. I kept accurate records: names, dates, times, places, phone calls, e-mails, text messages and dollar amounts, just in case I ever needed the leverage.

By Christmas I had slept with seventeen different women on almost fifty dates and had had six blood tests. All negative.

"Why do they want me?" I asked Sonja.

"You're tall, dark and handsome with rugged good looks. You're clean—most male escorts are addicts, you know—crazies. Unstable. You're polite, educated and hung. You're empathic. You listen. You make intelligent conversation. You get out the oil and massage us. And you're an excellent kisser. You're a lover."

"That's not why," I replied.

"Yes it is. And It's the buzz. You're the hot young tip all the ladies want. After they bang you they sit around in bistros comparing notes and whispering about doing you again. You have created your own mystique. Enjoy it while it lasts."

A couple days after Christmas, date number fifty—the famous one, banged me in a suite at a swish midtown hotel. Of all the ladies to that point, she was the most insecure and needed the most reassurance, but soon let go and became a wild, unfettered lover. I could not believe the way she moved on top of me, or how much she liked it when I rolled her around on the bed. Great kisser. One of the best. Yet terribly vulnerable and riddled with self doubt. It made me happy to make her so happy, even if for only a few fleeting hours on a cold, gray miserable day.

"Can I give your number to a friend?" she said after.

"Sure," I said, knowing Sonja wouldn't like me going off the reservation, but I didn't care. I had enough information to embarrass a whole bunch of people, Sonja included. The book deal alone would be worth a million and to hell with law school.

Next day, three thousand arrived by Sonja's courier. Another thousand arrived by separate courier, a tip from the famous woman. The day after that her friend called. A household name, she was so famous I almost said no. Her international beauty slid up and down on my rigid member for an hour at the same posh hotel, her famous tush slapping against me insatiably. When that wasn't long enough, I stayed a second hour free of charge, giggling and rolling around between her legs. She paid in full anyway, six thousand plus a five hundred tip. It seemed like a lot of money to me, but was chump change to her. When she wanted more, we agreed to travel separately to a five star resort on a Caribbean island which catered exclusively to the obscenely rich and famous. Through a third party she arranged for me to book a room there.

That was the first week in January. With time off between semesters, Sonja didn't mind me taking a vacation, not surprised that I used some of my new found wealth to fly someplace warm and sunny. Little did she know I was hard at work, earning 20K for the week. I had to be discreet, going back to my own room each morning, avoiding superfamous-household-name-international-beauty and her entourage during the day. I spent early mornings in the gym and running the beach, mid-mornings on a chaise by the pool getting a wicked good tan, early afternoons observing the siesta with a snooze then late afternoons sipping exotic cocktails in the shade of swaying palms on the beach.

One morning at the pool she sprawled on the chaise next to mine and started a conversation. I acted like a discreet fan, asking for her autograph and chatting in awe like I had just met her. She acted like she was comfortable enough with me to open bathrobe and sunbathe in her bikini. Hotel security gazed nervously at me, unaware that I had been between her legs all night the last three nights, my lips having tasted every inch of her heavenly body. When she got up to leave, I gave a small wave. Famous people, she had told me, like it when you treat them like regular people. I didn't say I already knew this wasn't really true. They want close family and friends to treat them like regular people. They want strangers to treat them with deference until their social status has been determined.

When I got home, Sonja ordered me to meet her out in the Hamptons the next day. We were all alone there, the houses empty for the winter, the heavy grey sky lowering at the approach of snow. No sooner had I removed my coat when she slammed a half dozen tabloids on the table in front of me, one after the other.

"Mystery man?!" she yelled. "Mystery man! What the hell do you think you're doing?!"

"Take it easy," I said, thinking of the baby in her swollen belly. My baby.

Blurry telephoto shots, they were obviously taken at great distance, showing superfamous-household-name-international-beauty sunning poolside on a chaise lounge. Next to her lounged a tall, dark-haired young man in swim trunks and a 24 hour shadow. Me. Headlines screamed Who Is This Mystery Man? Thankfully the resort refused to comment on guests. Pictures showed us talking, her signing an autograph and the two of us sunning side by side which looked suspicious since we were surrounded by empty chaises. Thank God I said no when she asked me to rub sunscreen on her back. Other photos were close ups of me sunning and running alone on the beach, my face hidden only by sunglasses. I scanned the articles, unable to remember anyone taking pictures of me.

"They don't know your name, Martin," Sonja said, reading my mind, "but it won't be long before they find out. One of the ladies will talk. Someone always does."

I quickly scanned pictures and copy again, understanding instantly why celebs follow tabloids so closely. It's an ego kick and I wanted to know everything they were saying about me. One rag read: Tall, dark stranger alone at this resort? We don't think so.

"How much did she pay you?" Sonja demanded.

"I don't know what you're talking about," I said.

She ripped the paper from my hands and got right in my face. "Don't you ever bullshit me, young man, or I will ruin you! Tell me!"

"No."

"What did you say?"

"I said no."

"Tell me!"

"It's not your business," I said.

"That is IT!" she said, pounding on my chest. "I made you! And I will destroy you!"

I don't know why she hit me. Were she the cool operator she pretended to be, she'd simply throw me out and make good her promise to ruin me. Instead I grabbed her arms, pulled them down and kissed her.

"No!" she said, struggling.

I pulled her into another kiss, holding her firmly from the side to avoid baby and a knee to the groin. Sonja struggled against me, then caved, kissing me passionately in return. Fifteen minutes later we were still kissing, only we were naked in her bed. Wind whistled in the eaves outside and it began to snow. Across from her bed a fire roared in the fireplace. Six months gone, Sonja was getting very big. We did it spooning. I felt the baby move as I caressed her mother's belly. We already knew from the sonogram.

"The amnio has come back normal for a healthy baby girl," Sonja said as I held her in my arms.

I've never particularly wanted to be a woman, but the moment I felt baby move under my hand I became intensely jealous that I would never have the experience of carrying a child.

"Marry me," I said, still spooning Sonja afterwards, still inside her.

"What?" she said.

"Marry me. Leave him and marry me. Does he even know it's not his child?"

"No. I had sex with him that week."

"So I might not be the father."

"Possible, not probable. His count is low. Always has been. We were lucky to have Cynthia and I've never had to use birth control. Not with him, anyway."

She never called her daughter Cynthia. Not to me, anyway. I thought about Cindy and how she would be affected by the news of her mother's affair with her ex-lover and having his baby. Conscience pinched hard. I wondered if Sonja would be a better mother to her new daughter than she was to Cindy. I wondered if I'd even be allowed in my daughter's life.

"This baby is yours," Sonja whispered, her hand over mine on her belly. "Feel here," she said moving my hand.

For a long time there was nothing, then came a little bump.

"Is that her shoulder?" I whispered.

"That was a kick," Sonja smiled. "They're head down, you know, with feet and bum up here. Sometimes she sticks her foot between my lowest ribs and tries to pry them apart."

"I didn't know babies moved so much at six months."

"Some do. Cynthia was a quiet baby. Hardly moved at all."

Feeling for the next kick, I thought about Cindy again and everything that had transpired since I went out on the boat with her that first night. I had made a mess of life getting involved with these people but there was no way back.

I decided it was all Cynthia's fault, my Cynthia. Had she not dumped me for a summer fling, I wouldn't be here. She called and texted several times when she returned from France at summer's end, but I never replied. As far as I know, she made no attempt to meet me in person. I guess that's how important our relationship had been to her.

Sonja squeezed me inside her. I squeezed back and we both giggled.

"It's your turn, stud," she sighed.

I took my turn, bouncing mom and baby with each thrust of my body.

"I can't marry you, Martin," Sonja said resting in my arms after. "I can't leave what he gives me."

"Wealth and power," I said.

"Status," she replied. "Lots of people have wealth and power but never use it to attain status."

I remembered words I had written months before: seeing the Baldwin sisters walk naked out of the ocean in full view of two young college boys next door I said they were sending a message about wealth, power and status. And the greatest of these is status.

"Do you have any feelings for me at all?" I asked.

"Yes, I love you, Martin, but I love many things."

Another question came to mind, but I decided to let it go.

"The ladies all want to see you again," Sonja said, as if it would brighten my demeanor.

"I don't want to be their gigolo anymore," I said. "I'm finished."

"I'll tell the ladies you're out of their class now," she said. "But don't let that stop you."

I stayed all night in her bed. In the morning she hugged me goodbye and I drove back to the city in the snow.

When I got home, I found an text from superfamous-household-name-international-beauty. It was on the computer, not my cell. A friend of hers wanted a date: Superfamous Two. A text from Sonja asked if she could see me again. It was a request. Not an imperative.

I grabbed my new class schedule, walked over to Fordham and bought textbooks for the upcoming semester, glad nobody recognized me. Yet.

The next morning my bank confirmed that 20K had been wired into my account. An hour later I took delivery from a courier. Three grand from Sonja. And a five hundred tip. It dawned on me at last. This was the status she sought: sharing the same male escort with Famous and Superfamous.

I got out my cell, dialed the number and got a personal assistant who put me right through. Superfamous Two said hello, asked if I could travel and gave me destination and dates for our rendezvous. Then I texted Sonja.

When and where?

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9 Comments
hudson2121hudson2121about 1 month ago

Loved it. Fitzgerald would be proud. And would be chuckling.

vrieseavrieseaover 1 year ago

Enjoyed it very much especially the interaction between Martin and Cinthia. Very descriptive writing and excellent story. Thanks for taking me there. - Vriesea

barcomberbarcomberover 3 years ago

Loved it. Didnt quite go along with screwing the maid while in love with Cindy, but still a five

AnonymousAnonymousalmost 4 years ago
SECOND THAT COMMENT

I was going to write a comment.

But my comment 2 1/2 years ago said it so well

that there's no use to try again.

Again awed at the writer's skill.

Unhesitatingly 🌟🌟🌟🌟🌟

Paul in Oklahoma

AnonymousAnonymousover 6 years ago
WELL BEYOND

I have no idea how realistic this story is since it goes well beyond anything I have ever remotely experienced or even could imagine. It doesn't matter because it was a spellbinding tale twisting through unexpected vistas coming up over the horizon or around the bend. And like majestic scenery, leaving you awestruck that someone could create it.

Paul in Oklahoma

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