Ups and Downs

Dinner and Dessert

With less than two weeks to go until our big trip to New York and Connecticut, Woody called Rafael and me into his office to begin making preparations. I took notes with my new Wacom note pad. Our itinerary would look something like this:

Wednesday morning: fly to New York City, check into the St. Regis Hotel (overlooking Central Park and just two blocks from the Museum of Modern Art)

Thursday: cocktail reception in Mr. Block’s suite, followed by dinner for 10 in the Presidential Suite

Friday afternoon: Mr. Block, Woody, and I take the train to Stamford, Connecticut, and then travel by rental car to Greenwich for the art show; Rafael remaining in New York (unsupervised)

Sunday afternoon: take the train back to New York City

Monday: Mr. Block and Woody attend an international conference on LGBT+ rights at the United Nations; Rafael and I free for the day

Tuesday: Mr. Block, Woody, and I fly back to San Diego; Rafael remains in NYC for another week before flying to Spain

“We don’t always stay at five-star hotels,” said Woody, “but Mr. Block chose the St. Regis for two reasons: one, he will be entertaining a very exclusive group of gentlemen, and two, he sees this as an opportunity for the two of you to learn what constitutes first-class service. So, while we are there, take pictures and take notes. Before we check out, you will meet with the hotel manager to ask him any questions you may have. This is an exceptional learning opportunity for both of you, so make the most of it.”

After going over the general outline, Woody dismissed Rafael but kept me behind to work out details. My assignment was to make all the reservations—flights, hotels, train, rental car, and dinners. At the art show, I would be expected to provide whatever services might be needed by Mr. Block, Woody, or the show organizers.

“You’re in charge,” Woody told me, “but don’t be afraid to ask for help. Rafael has been through all of this before, so he can answer almost any question you might have. And when you talk to the sales manager at the hotel about that dinner, pull Kim into the conversation to work out the menu and other arrangements. He’s a pro at that.”

As I got up to leave Woody’s office, he called me back and handed me two things: a box containing the latest iPhone and a credit card. “Use these to make the reservations,” he said. The credit card belonged to Mr. Block’s account, but it had my name on it.

For the next week and a half, I worked my tail off, not only making the reservations and other plans for our trip, but also assisting Rafael, Ron, and Kim in their duties, learning as much as I could so that I could fill in when they took days off.

Of course, I still managed to squeeze in sexual adventures two or three times a day. I had sex before work and after work and sometimes during my lunch break, but never during work hours. I never had to look far for available or willing sex partners. They were everywhere.

I remembered what Woody had said about having sex in the limo, the barn, and the boats, so I made sure to play out those fantasies as well as quite a few others.

On the day of our departure, Ron drove the four of us (Mr. Block, Woody, Rafael, and me) to the airport in the Navigator—plenty of room for the five of us plus our luggage. Sitting next to me in the rear seat, Woody handed me an envelope containing $500 in bills of various denominations. “Remember,” he said, “you’re in charge. This money is to cover tips and any other incidentals that you can’t charge to the card. Use it wisely, but don’t be chintzy with the tips. These guys work hard to make our lives easier. The least we can do is to show them our appreciation.”

On the plane, the four of us sat in first class. I had originally booked Rafael and me in coach, but Woody made me change it. “You must constantly be watching out for anything that Mr. Block or I might need,” he said, “and you can’t do that if you’re not with us.”

Mr. Block and Woody took the aisle seats, giving Rafael and me the window seats. Since he and I couldn’t exactly chat with our bosses sitting between us, we texted each other as soon as the overhead lights went off. We joked about the flight attendants—two females in first class and two guys in the back who didn’t exactly appeal to either of us. We lamented the fact that Freddie wasn’t working that flight.

We initially dismissed the idea of having sex in the lavatory since we had both already been inducted into the “mile-high club,” but then it dawned on us: yes, we had both had sex on a plane, but not with each other. When Rafael got up to go to the lavatory, I waited about a minute and then followed him. Walking away, I heard Woody remark to Mr. Block, “They’ll be a while,” which drew a snicker from Mr. Block.

Rafael and I laughed about the fact that the lavatory in first class was bigger than the one in coach, which made it easier for him to ride my dick at 35,000 feet. At one point, we hit a little bit of turbulence, but that only drove my cock deeper into Rafael’s ass. I thought he was going to give us away when he squealed with stunned delight.

When we arrived at the St. Regis in the limo they had sent for us, the desk clerk immediately called the hotel manager, who came out to welcome us. With two cute bellhops carrying our luggage, he escorted us to the Presidential Suite, which was huge—basically a 3000-square-foot luxury apartment. It not only had two bedrooms, one for Mr. Block and one for Woody, but also a living room, a private office, and even a dining room, where our dinner would be catered. The manager, Mr. Danvers, also introduced us to Conrad, the butler assigned to the Presidential Suite. I tipped each of the bellhops $20, but Woody pulled Conrad aside and told him that Rafael and I were there to learn about superior service and would he….

“Mr. Danvers has already explained the situation to me,” Conrad assured Woody. “It will be my pleasure to assist them as well as you and Mr. Block.” Woody thanked him and slipped him a $100 bill.

The two bellhops then led Rafael and me to our rooms down the hall. Though the rooms were not suites, they were more elegant than I could have ever imagined. We had connecting rooms, each with a king-size bed.

As we settled into our respective rooms, there came a knock on my door. It was Conrad. “Mr. Block would like to have dinner at 7:00. Would you like me to reserve a table in the restaurant or will you have dinner in the suite?”

“I’ll have to call Woody and ask him,” I said, but before I could move, Conrad informed me, “Mr. Woodward said that the decision is yours to make.” When Woody said I would be in charge, he wasn’t kidding.

“Hmm. What would you recommend, Conrad?”

“I am happy to make whatever arrangements you wish, but since you will be dining in the suite tomorrow evening, perhaps you would like to try our restaurant tonight. The menu is excellent, the ambiance is quite nice, and you might become acquainted with some of our other guests.”

Conrad was understating the case. The Court restaurant was gorgeous and filled with handsome, well-dressed, and obviously rich gentlemen—mostly older, but some younger than 30. The four of us were well dressed too, Rafael and I in our new Brooks Brothers suits.

When the maitre’d asked Mr. Block if we had reservations, he and Woody remained silent and just looked at me. “Uh, reservation for Mr. Block,” I bucked up.

“Nice save,” Woody whispered to me as we were led to our table. “You’re catching on.”

I felt a twinge of embarrassment at having initially missed the cue, but hearing Woody compliment me pumped up my chest like you wouldn’t believe.

Conrad was right about the menu too. The food was delicious.

“There’s nothing on our calendar tomorrow until the cocktail reception,” observed Woody, “so what do you plan to do with your day, Joe?” My instinct was to say that I would take the time to see some of the sights of New York, but the fact that Woody directed the question to me and not to Rafael and me both, tipped me off that this might be a test.

“I think I should get together with Conrad to make sure that everything is in place for the reception and the dinner.”

An ever-so-slight nod from Woody said to me, “Go on.”

“And I think I should reconfirm our train and hotel reservations for Greenwich.”

When Woody took a very faint breath and leaned back in his chair, I knew that I had scored, but I didn’t quit there.

“Is there anything else I can do for you tomorrow, Mr. Block? Lunch reservations perhaps?”

The faint smirk on Woody’s face said to me, “Now you’re just showing off.” And I ate it up.

“That won’t be necessary,” replied Mr. Block. “I think Woody and I can take care of ourselves for a few hours. Why don’t you and Rafael use the time to get acquainted with the Big Apple? It’s a fascinating city.”

I thanked him but reminded him that I was just a phone call away if he needed anything.

When dinner was concluded and I saw the waiter approaching our table with the bill, I signaled to him to bring the check to me, which he did. After looking it over and adding a generous tip, I signed the check to my room. I think even Rafael was impressed.

As we were leaving the restaurant, we passed a table with two very handsome gentlemen whose eyes followed us out. When we got to the elevator, I said, “You guys go on up. I want to check with the concierge about sightseeing tomorrow,” which was a lie, of course. I was headed back to the restaurant to get acquainted with the two hunks.

When I approached their table, they invited me to sit down while they finished their dinner. “They have sumptuous desserts here,” I commented.

“They certainly do,” gushed one of the men, “and they’re not all on the menu apparently.” I feigned embarrassment, which they thought was adorable.

They complimented me on my new suit, which was obviously a ploy since they were both impeccably dressed themselves, and one of them asked if he could feel the material. Of course, I said yes. I’m not stupid. As he stroked the lapel between his thumb and finger, he let his hand rub against my chest, especially my nipple, which started to rise to the occasion. “Oh, man, this feels really good,” he cooed. “I’ll bet,” said his friend, who had started a seduction of his own by rubbing his leg against mine under the table.

Taking the hints, I told them about our shopping trip to Brooks Brothers and also to The Body Shop in San Diego, which led them to ask what kind of underwear I had bought and what kind I was wearing that night. “I’ll bet you look fucking hot in them,” said one of the men. “And even better out of them,” the other one dared to say.

“And your friend who was with you at dinner. Did he buy new underwear too? I wonder what he’s wearing tonight.”

“I don’t know,” I confessed. “I didn’t check before we came down to dinner, but I’m sure he’s in his room now. Maybe we could all go ask him.”

Well, I didn’t exactly have to twist their arms. They quickly finished their dinners and followed me upstairs.

When I knocked on Rafael’s door, he must have been exercising some ESP because he came to the door in his sexy underwear, which drew oohs and aahs from our two new friends. Rafael didn’t even look surprised when I led them into his room. Maybe when I said I was going to talk to the concierge, he suspected where I was really going and anticipated what the outcome would be.

The outcome, of course, was the four of us ending up naked in Rafael’s king-size bed. They both claimed to be versatile, but when they saw our dicks, they insisted on having us fuck them, which Rafael and I were perfectly happy to oblige. Actually, we swapped back and forth, fucking our respective partners for a few minutes and then, with a tag team slap of the hands, trading partners. The businessmen loved it.

As we fucked them, they occasionally leaned over to kiss each other and sometimes pulled us into kisses. It was such a delight to watch two incredibly handsome men kissing each other and kissing us. It was such a turn on…as if we needed any extra stimulus. Rafael and I both shot our loads more quickly than either of had intended and somewhat to the disappointment of the guys under us, so we tried to make up for the abbreviated fuck by sucking on their cocks, which they also unloaded more quickly than anyone would have preferred.

With our mouths full of their man cream, they kissed us again, swapping their cum with us and with each other until we ended up in a four-way cumfest.

After they got dressed and left Rafael’s room, he and I showered, but before we could finish drying off, the phone in his room rang. It was the two guys inviting us to their room. “Our husbands are back from their evening out and would like to meet you.”

To be continued