Ups and Downs

Mile High

Our non-stop Delta flight from Atlanta to San Diego was not scheduled to depart until 11:00 a.m.—plenty of time for a quickie, I thought, but when Woody pressed me to get a move on, I recalibrated: OK, maybe in the Mercedes? That would be cool, especially with the driver peeking in on us through the rear-view mirror. Another unfulfilled fantasy.

Considering the expensive car rental and the premier hotel accommodations, I was not surprised when Woody produced two first-class tickets at the Delta check-in counter. We each checked one suitcase and kept a carry-on to the plane.

I had taken Woody’s advice and worn comfortable clothes, a tank top and a pair of grey cut-off gym shorts that really made my bulge pop with the designer briefs I was wearing underneath. I actually felt self-conscious with people—men and women—staring at my crotch as we walked to the security checkpoint, so I held my carry-on bag in front of me—until we got to security, that is.

Woody walked through the metal detector ahead of me and retrieved both of our bags. When I reached for mine, he refused to deliver it. “Head high, mister. Flaunt it. You deserve the attention.” I felt embarrassed but at the same time very flattered, especially considering the source of the compliment.

I started to relax when I noticed that practically everyone who gaped at my crotch also smiled at me. So, I smiled back, and that boosted my confidence. I believe it boosted my bulge a bit too, but that just made me smile even more.

When we boarded the plane, the flight attendant who greeted us swiped my butt. At first I felt a bit violated, but he was awfully cute, so I just smiled and winked at him, and he pretended to swoon, which gave us both a big laugh.

Knowing that I had not actually flown much—and certainly not across the country—Woody took the aisle seat and gave me the window seat so I could look out at the passing scenery far below. Once the plane had ascended and leveled off and the fasten seat belt sign had gone out, I got up to go to the restroom, but as I was crossing past Woody, we hit a slight bit of turbulence, which threw off my balance and almost landed me in Woody’s lap, which I wouldn’t have minded at all, but I wasn’t sure how he would have felt about that.

Not being accustomed to airplane lavatories, I fumbled with the door handle at first, but the cute flight attendant, who suddenly appeared out of nowhere, reached around me and opened the door. I turned to thank him, but he unexpectedly pushed me into the compact water closet, followed behind me, and locked the door.

Without saying a word, he threw himself at me, sinking his tongue deep into my mouth and rubbing my crotch feverishly. Of course, I grew hard in an instant. Like I said, he was awfully cute. And unrelenting. Before I knew what was happening, he yanked down my shorts and briefs, pausing just long enough to gasp at the sight of my package, shoved me down onto the toilet seat, pulled down his own pants, and plopped down on my stiffie. Let’s just say he knew his way around a cockpit.

He did all the work, popping up and down on my dick like a supercharged electric pump, the very definition of a power bottom. It was the shortest quickie I had ever experienced. I shot my wad in no time, primed no doubt by my unfulfilled morning fantasies of fucking Woody in the Mercedes, and when I came, the cutie got up, swerved around, and stuck his own hard tool into my mouth, spewing a torrent of jizz down my throat. When he finished unloading, he pulled up his pants, kissed me on my cum-soaked lips, and slipped quietly out of the stall. Fortunately, I still had enough presence of mind to lock the door behind him.

I peed, which was why I went to the toilet in the first place, and when I went to wash my hands, I noticed that a small spot of cum had dribbled onto my shirt. I tried to clean it up, but I only spread it more. When I returned to my seat, Woody pretended not to notice the stain, but his devilish grin assured me that he had seen it, and he knew where it had come from. (Or should I say, “…where it had cum from”?) Once I sat down and re-fastened my seat belt, he leaned over and whispered, “Welcome to the club, stud.”

I felt so embarrassed that I just wanted to open the window and jump out of the plane, but that embarrassment soon gave way to a feeling of pride and accomplishment. Woody and I enjoyed the rest of the flight to San Diego in silence but with impish grins on our faces.

When we disembarked from the plane, my cute flight attendant again slapped me on the butt and handed me a card, which I promptly stuck into one of my pockets. Later, when I had a chance to get a good look at the card, I found his name and phone number on one side (it was a San Diego area code) and these words printed on the flip side, “Welcome to the Mile High Club.”

At baggage claim we were met by another handsome young man who turned out to be Rafael, the assistant I would be replacing if Mr. Block decided to hire me. “Mr. Block sent me to pick you up,” he said. “He had to run up to L.A. on business but will be back later this afternoon.”

“You hungry?” Woody asked us both.

“You know me, Woody,” replied Rafael. “I’m always hungry.”

And I guess you could say that I had worked up an appetite on the plane, so, “Yeah, I’m famished,” I concurred.

“Mo’s?” asked Rafael.

“Good choice,” answered Woody.

Since the car was parked in the nearby garage, we walked over, loaded our luggage, and made ourselves comfortable in the white Porsche Panamera. Woody ushered me into the front passenger seat next to Rafael and positioned himself in the back.

“Mo’s Urban Grill is a bit of a rainbow landmark in San Diego,” explained Rafael. “It’s a gay Mecca, but lots of straights go there too. It’s in a convenient location in Hillcrest, San Diego’s  gayborhood, just a few minutes’ drive from the airport, and the food and service are first rate. And so are the waiters,” he whispered to me with a wink, as if he were sharing some dirty little secret.

On the short drive to the restaurant (and later to the house), Rafael did all the talking, pointing out landmarks and other places of interest. At first, I thought it was strange that Woody remained as quiet as a church mouse, but later I concluded that this was all part of their plan, and it was working. As we sat at a table at Mo’s, a nearly unending parade of friendly guys stopped by to say hello to Rafael, and he very enthusiastically introduced me to each of them. They all shook my hand, and a few even gave me a hug or a little kiss. And every one of them took a glance at my bulging crotch. If this was the welcoming committee, they were certainly doing their jobs.

“Everything here is good,” Rafael assured me as he scanned the menu, and then he mentioned three or four of his favorite dishes. “But don’t eat too much,” he cautioned. “Kim is preparing a feast for dinner tonight.”

After lunch we drove about 20 minutes north to Rancho Santa Fe, a beautiful little city of expensive homes, sophisticated horse ranches, and elegant estates. I fully expected to find a mansion when we got to our final destination, but the property was far beyond anything I could have imagined.

The long, wide tree-lined private road beyond the imposing wrought-iron entry gate took us to a circular driveway that curved under a wide port cochere flanked by flowing Roman fountains. The Santa Barbara-style home seemed to stretch forever, but the appearance proved to be somewhat deceiving because a long expanse of it consisted of an eight-car garage. Still, there was much more of the house that wrapped around the sides, imperceptible from the front.

As Rafael went to park the Porsche in the garage, another handsome young man wearing nothing but a red jock strap met Woody and me at the front door. “Joe,” said Woody. “This is Ron. He will show you to your room, and Rafael will bring your bags. Once you’re settled in, they will show you around and introduce you to the others.” Others? How many other guys are there here? Is this a house or a hotel?                    

The marble-floored grand foyer led to a huge area that I can only describe as a ballroom. It was a rotunda with 20-foot walls reaching up to a domed stained-glass ceiling. A grand piano sat right in the middle of the floor, surrounded by wood-paneled walls behind curved sofas and swivel chairs that formed conversation pits, each one the size of an average living room. The space appeared to be designed so that large groups of people could sit and enjoy a piano concert, get up and dance, or just socialize in small groups. The wall directly across from the front door we had just come through was made of glass, providing a spectacular view of the pool, spa, and expansive patio in the back yard.

“Our bedrooms are upstairs,” said Ron. “We’ll give you the grand tour after we get you settled in.”

From the top of the stairs, we walked down a long corridor with walls adorned with erotic paintings. Some of them were very explicit; no doubt, some people would describe them as pornographic, but all were masterfully done. These were not cheap reprints. These were original paintings signed by the artists, a few of whom I recognized: Michael Breyette, Michael Kirwan, and Javier Trelis Sempere, among others.

Walking down the hallway, we passed at least half a dozen bedrooms before we reached the end of the corridor. “This is your room,” said Ron. “It was Rafael’s, but since he’s leaving soon, Mr. Block put him in the guest suite temporarily.”

The room was bigger than three rooms in my house back in Columbus. In addition to the queen-size bed and matching furniture, a computer desk sat in one corner, and in another sat a large sofa facing a large-screen TV on the opposite wall. More erotic art graced other walls. A private bath and a large walk-in closet flanked the room to one side, and on the other side, glass doors led to a balcony overlooking the Olympic-size pool, spa, and gardens.

“How big is this property?” I asked Ron.

Standing behind me and resting his bare arm on my shoulder as if he were steadying a rifle, Ron pointed to a large pond beyond the palm trees that graced the pool area and provided privacy from prying neighbors (although no other houses could be seen anywhere around). “See that fence beyond the pond?” Ron asked, “That’s the property line. The land that you saw along the drive as you approached the house, that’s all part of the estate. Altogether, I think it's about 18 acres.”

“Wow! That’s a lot to take care of,” I gasped.

“That’s why Mr. Block has so many assistants,” he nodded.

From that lofty perch, I also saw several young men in the yard. Some wore skimpy swimsuits, some, like me, wore shorts and tank tops or T-shirts, and a couple of guys lounged around the pool stark naked.

Seeing the puzzlement on my face, Ron explained, “Mr. Block insists that his staff be comfortable. As long as there is no one here but us, we’re free to dress however we like.” As if to emphasize the point, Ron turned around, flashed his bare butt at me, and snapped the straps on the back of his provocative jock strap. It seemed like an open invitation, and I was admittedly tempted, but then Ron turned the conversation back to my orientation.

“The comfort rule applies to your room as well,” he said. “So, if you don’t like the furniture, or the mattress is too hard or too soft, or you want walls and bedding of a different color, just say so, and we’ll change it. And Mr. Block has lots of great artwork, not only what’s in the house, but lots more in storage, so if the ones in here don’t appeal to you, you can replace them with others from his collection, or you can put up your own. Maybe you’d prefer a poster of Chris Evans as Captain America or Chris Hemsworth as Thor,” he snickered.

“That’s great to know, but it’s hardly necessary,” I responded. “I’m only going to be here for a few days. I haven’t met or even talked to the mysterious Mr. Block yet. He may not offer me the job.”

At that, Ron just laughed. Placing one hand on my shoulder as if to emphasize the veracity of his statement, he said, “Trust me, buddy. If you’re here, you’re in. The boss wouldn’t have brought you here if he hadn’t already decided to hire you. Believe me, he has done his research on you, as he did with all of us, and he trusts Woody’s judgement completely. If Woody thinks you belong here, Mr. Block will take his word for it.

“Of course,” he continued, “you may decide that you don’t want to work here, but if you do, you’re fuckin’ crazy.”

“Who’s fucking crazy?” came the voice from the doorway.  It was Rafael bringing my luggage from the car. In the interim, he had changed into gym shorts like mine—no shirt—and when he walked, it was obvious he was going commando.

“You’re crazy,” sniped Ron as he grabbed a pillow from the bed and threw it at Rafael, who charged at his attacker and flattened him on the large bed. The two of them scuffled playfully for a minute or so before they turned and bombarded me with pillows. Naturally, I fought back and ended up with the two of them all tangled up on the bed. One thing led to another, and soon Rafael was rubbing Ron’s bare ass and encouraging me to rub the other butt cheek, and Ron was sticking his hand up the leg of Rafael’s shorts. Both men looked to me for a signal as to whether to go further or not.

To be continued..