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Driving up to my boss's house 15 minutes late, I was beside myself. There'd been an accident on the freeway and then I had to follow a slow-moving delivery truck up the hill to Philip's house.
I had texted him to let him know I was delayed, and he replied with his usual "No prob". But I pride myself on always being on time, if not early. So I was mentally kicking myself for not having left my apartment even earlier than I did today.
Philip Caine, my boss, lived in the Hollywood Hills up one of those narrow winding roads that was essentially a one-way street. If someone was coming down the hill while I was going up, I had to pull off into someone's driveway to let them by.
As a top-level executive at the studio, he could have afforded a much bigger house in a much more exclusive neighborhood. I'd accompanied Philip to enough meetings at his colleagues' homes in Brentwood and Bel-Air that were four or five times the size with sizeable full-time staff. But despite his wealth and his huge personality, Philip and his wife Daisy were surprisingly down to earth.
Don't get me wrong, their house was amazing -- a spacious 3-bedroom main house, a pool and guest house/cabana in the back yard, with a panoramic view that stretched from downtown to the ocean (on clear days). But they had no full-time staff -- just a housekeeper, gardener and pool guy who came once a week. Daisy did all her own shopping and cooking, and employed a personal chef only occasionally when they'd host a big party and she didn't want to be stuck in the kitchen.
If they'd had a family, I'm sure they'd have a larger home. But, as it was, they had no kids or close extended family. Instead, they showered their affection on each other, their 2 rescue dogs, and their menagerie of friends.
Although I was Philip's employee, I considered myself part of that menagerie. Daisy treated me more like a favored nephew than her husband's assistant. And I ate it up, since I'd left my family and friends back in eastern Canada when I moved out to LA a few years ago to go to art school. I was a regular guest at their house for dinner and they'd been devoted supporters of my budding side gig as a painter, attending nearly every gallery show I managed to land no matter how big or small, and buying a handful of my watercolors.
I was going to be driving Philip to the airport for his flight to Paris. He and Daisy would be celebrating their 25th anniversary by spending a few days in Paris followed by 4 weeks at a chateau they'd rented -- or rather, Daisy had rented -- in the Loire Valley. Daisy had departed a few days earlier to spend some time with friends in NYC. And then she and Philip would be meeting up in Paris.
This trip was a big deal for both of them. Philip hardly ever took 4 days in a row off, let alone 4 weeks. And Daisy hadn't ever entrusted the house or the dogs with anyone for more than a week or so. I'd earned my stripes as a house sitter for them when they'd gone skiing, to Napa and to Palm Springs for long weekends over the last year or so. I think they appreciated that the dogs were happy and well cared for, and that the house was usually cleaner and more organized than when they'd left. I'd also successfully dealt with replacing their hot water heater when it suddenly decided to empty it's contents into their garage as they were leaving for one of their trips.
I would be house and dog sitting for them for nearly 5 weeks. It was almost like a free vacation for me, since I'd be spending that time in a much nicer place than the 2-bedroom apartment in Hollywood that I shared with a friend from college. And because Philip would be out of the office, he told me I could pretty much work from home -- his home -- and only had to drive in to the studio to pick up his mail and any packages a couple times each week.
It wouldn't all be R&R for me, as I still had to monitor his email and voicemail -- dismissing the fluff and delegating the rest to his staff. And Philip had also left me with his credit card and a punch list of items to take care of around the house.
Philip had gained implicit trust in me in the short year and a half I'd worked for him. Unlike some of my predecessors, I wasn't trying to use the job with him as a stepping stone to a career in the industry. And unlike a couple of them, I wasn't trying to get into his pants as a way to advance my career.
I started off in his office as a temp, filling in for his assistant out for a few months on maternity leave. When she decided not to return, he offered me the job full time. He said he appreciated my honesty when I told him that this was a job to me, not a career. I needed something to pay off my student loans, since "watercolor portraitist" wasn't currently a super lucrative endeavor.
I pulled my old Honda to the side of the driveway, leaving plenty of room to back Philip's BMW SUV out of the garage, and walked up to ring the doorbell. I had a key, but I didn't feel comfortable just waltzing into someone's house unless they'd explicitly told me to do so.
Philip answered the door, cradling his iPhone to his ear, and motioned me in. He was shirtless, clad only in his navy swim suit that I'd seen him wear a dozen times before -- non-assuming trunks that probably cost more than the suit I'd worn on my first day as a temp in his office. ("Lose the suit, Zoolander," Philip had teased me. "Suits are for weddings and funerals.")
The volley short trunks showed off Philip's tanned, hairy legs. He played tennis and swam regularly, so he was in pretty good shape for a guy in his late 50. He had a fairly trim stomach, with just the slightest hint of a belly. That and his firm chest were both dusted with dark hair with a few tufts of gray here and there. He had broad shoulders, a swarthy complexion, and thick salt-and-pepper hair. He reminded me of an Italian version of my high-school track coach.
His hair still wet from the pool, Philip was chatting with Daisy and absentmindedly rubbing the hair on his stomach with his free hand. "It didn't get cancelled, baby, it's just delayed for a couple hours. I'll be there in time for lunch tomorrow, I promise. Yes, Tyler's here now. He's gonna help me get everything packed up. Now I need to go. Love you, Kitten. Bye bye."
As he ended the call, Philip turned to me and explained, "The airline concierge called me about an hour ago to let me know the flight was delayed. I didn't tell Daisy it was a mechanical delay or she'd have freaked out."
"Good call," I said.
"They said it was a minor thing. But you know how she gets," he added. "Since I had more time, I went for a swim."
I pulled up the airline app on my phone to check his flight status. "It's delayed 2 hours, but we're going to hit traffic at this time of day," I said. "So we should probably leave in about 90 minutes."
"Right," he agreed. "I'm just going to finish up a couple emails. I've got most of my stuff laid out on the bed. Can you pack it up for me."
"Sure," I replied as we headed down the hall. Philip took a right into the den and plopped down at his desk by the French doors open to the pool. I headed straight back to the master bedroom to pack his suitcase.
I folded his clothes and arranged them methodically into his suitcase. Missing from his clothes was a swim suit, and I knew from the website that Daisy had shown me that the chateau had a huge pool set out near the vineyards. I strolled into the den, as Philip tapped away on his keyboard with a pair of readers perched on his nose.
"Did by any chance buy another bathing suit?" I asked.
"No," he replied and then added, "Why?"
"If you're planning to swim at the house in France, you're gonna need one."
"Crap," he said. "I laid them out on the bed this morning to pack and then just grabbed them out of habit when I headed out to the pool for a swim. I should've just swam in the buff."
"There's still time for me to throw them in the dryer," I said.
"Great," Philip said standing up from his computer and shoving his chair back slightly. He proceeded to untie the drawstring at his waist, slipped his thumbs in the waistband, slid his bathing suit down over his hips and legs, and stepped out of them. He leaned down and grabbed the trunks off the floor and handed them to me.
"Do you want a towel or something?" I asked, trying not to stare too much at his naked body as he sat back down in the chair and mindlessly adjusted his penis with one hand.
"Nah. I'm gonna hop in the shower soon," he replied. And with a sly smile he added, "Besides, it's not like you haven't seen the goods before."
It was true. I had seen "the goods" before. A few times, in fact.
My fledgling art career was centered on watercolor portraits. I did the Etsy route for awhile. Send me a photo and $150, and I'd paint a 10 x 10 inch portrait -- of you, your spouse, your child, your pet, etc. I'd also paint larger scale watercolors of friends and acquaintances, with the occasional commission here and there. But my passion was nude portraits -- primarily of men.
I relied on male friends to model for me, or sometimes I'd work from photographs. Once I started making regular money in my day job, I'd occasionally hire a model for a particular composition I had in mind. It was these nude portraits that gained me some attention and minor notoriety at the gallery shows in West Hollywood, Venice, Downtown and Beverly Hills.
At the first show they attended, Philip and Daisy bought two of my pieces -- both of my friend Scott. One was him from behind posing on the beach, his tan skin contrasting against the light blue sky and deep blue of the water. The other was him perched on a boulder in Joshua Tree. It was full frontal, but a tasteful, fairly classic nude. Daisy gave them pride of place in the open living area of the guest house, that they used as a pool house for parties.
After attending another gallery show a few months later, Philip approached me at work with a proposition. "Daisy's birthday is coming up in a few weeks," he said, whispering as if anyone could hear us in the confines of his spacious office at the studio. "She loves your work -- we both do. I'd like to commission you to do a painting of me for her birthday."
"Wow, I'd be honored," I replied honestly. "What kind of portrait did you have in mind?" I was expecting him to reply that he wanted me to paint him sitting at his desk in one of his ubiquitous linen shirts. Or maybe by the fireplace with one or two of the dogs surrounding him.
"I wanna give her a nude. Maybe out by the pool. She'll eat it up," he said with a grin.
"Oh...okay. Sure," I stuttered.
"Can you handle a straight guy, Tyler?" he said with a wink.
"Of course. Absolutely."
We agreed on a price -- a very generous price -- and arranged a date on an upcoming Saturday when Daisy was out of town. I told him I usually take photos first to assess the composition and work on the painting with the live model for a couple hours, and then finish up the piece later using the photos as references for the finer details. Philip didn't bat an eye when I explained the procedure to him.
I showed up at his house at around 10:00 that morning, armed with my easel, brushes, paints, pre-stretched paper and other supplies -- and my camera. It wasn't my first time at his house, so he told me to head to the back yard to get set up while he finished a couple emails.
As I set up my easel and assessed the best angles and lighting, he strolled back to meet me. He'd doffed the polo shirt he'd been wearing and was now clad in just a pair of tennis shorts -- the bright white fabric setting off his tan skin.
"Are you ready for me, sport?" Philip asked. When I nodded, he added, "Where do you want me."
At the shallow end of the pool was a set of wide steps into the water. "I was thinking you could stand here on the first or second step," I explained. "We'll have the water in the foreground with the canyon and city behind you."
"Sounds great. You're the expert, Tyler," he smiled. And then he reached down and unbuttoned and unzipped his shorts, slid them off and tossed them onto a chair. He stepped into the pool and then turned to face me. "This good?"
"Yes, that looks great," I replied, my mouth feeling suddenly dry. The composition did look great, and so did he. His tan, hairy chest and legs contrasted with the lighter skin of his ass and pelvis. I knew he played tennis a lot, and it was apparent that he probably did a lot of it shirtless. His butt wasn't nearly as hairy as his legs, but I could see some fuzz catching the sunlight. The front was another story: he had an abundant bush of dark pubic hair that set off the light skin of his floppy penis and balls. His circumcised cock wasn't huge, but at about 6" flaccid and relatively thick, it probably put some of his tennis buddies to shame in the showers. His balls were a bit larger than average, too. In their present state, they were fairly tight to his body and lifted his penis up a bit. I couldn't help but wonder what it looked like when he was aroused.
Snapping myself back to reality, I proceeded to take several photos of Philip assuming a variety of poses. As I flipped through the shots on the screen of my camera, I settled on a pose that I thought truly captured his personality. He was standing with his legs spread about shoulder length apart, with one hand on his hip, his fingertips just touching the top edge of the inverted triangle of his pubic hair, and the other holding a Bloody Mary at his side. I stepped into the calf-high water and showed him the shot.
"I LOVE it!" he roared. "Daisy's gonna love it. And I'm guaranteed to get laid that night!"
He said it as if it was a rare occurrence. But I'd been around him and Daisy enough to know that they had a very active and abundant sex life. They were clearly crazy about each other, and couldn't keep their hands off each other even after more than two decades of marriage. Philip had confessed to me that he'd had plenty of opportunities at work and while traveling to mess around with other women, but that he couldn't do it -- save for the occasional hand job after a massage. "Daisy doesn't mind that," he said. "She even got me a happy ending massage once for my birthday." Daisy also apparently didn't mind that Philip consumed a fair amount of porn. He didn't bother trying to hide his laptop or iPhone screen around me, so I'd seen many still shots and videos of large-breasted beauties in various states of undress, alone and with one or more partners. His taste seemed to lean toward women who looked like Daisy, which was kind of sweet.
Philip held his pose in the pool for about 45 minutes before requesting a break. He offered me a drink and headed into the house, still fully nude, to get me an iced tea.
I thanked him as he handed it to me, and he asked, "Will it screw up anything if I go for a dip before we get started again? It's getting warm out here."
"Yeah, it is," I replied. "That's fine. It won't matter if you're wet."
"You're welcome to join me, Tyler," Philip said as he eased himself down into the water. "It feels great."
"Oh, that's okay," I stammered. Truth be told, the water did look enticing. My gray t-shirt was wet at the pits, and I could feel the beads of sweat running down the middle of my back.
"Strip down and come on in," he urged. "It's just us here."
"Okay, maybe just for a little bit." I pulled off the wide straw hat I'd worn to shade my face and pulled my t-shirt off over my head. I unfastened my beat-up cargo shorts and slid them down, and then, looking around one last time to ensure no one else was in the yard, I slipped my blue briefs off. The light breeze on my sweaty bare skin did feel great after standing out in the sun.
"Wow, you ARE white!" Philip laughed as I eased into the water.
"Scottish skin doesn't tan well," I smiled. It was true, I was very fair skinned with light reddish-brown hair, fine wisps of the same color in my armpits and groin, and only a fine fuzz of even lighter hair on my legs and arms. At 5'6" and a slim 140 lbs, I was frequently deemed a "twink" by my friends. Slightly disproportionate to my size, my penis was a "shower". It was nearly 7" flaccid and gained only a little length when erect. My balls hung low in their sack to my mid-thigh.
After swimming around for a few minutes, we got out of the pool and sat on the ends of adjacent chaise lounges while sipping our drinks. The sun quickly dried us off and made towels unnecessary.
It was a little surreal to be having a naked chat with my boss, but there was no sexual tension. Philip was clearly comfortable with his own sexuality and with his body, and didn't seem at all bothered having a nude conversation with a gay guy a couple feet away from him.
"We should probably get back to the painting before the light changes too much," I said rising from the chair and reaching towards my clothes.
"You don't need to get dressed," Philip said casually. "We'll probably end up getting back in the pool again."
"Uh, okay," I said. "I should probably put some more sunscreen on." I reached into my art bag and pulled out a can of aerosol sunscreen. I stepped away from the pool and sprayed down my chest, stomach, arms shoulders and legs. "Can you spray my back?"
"Sure," Philip said grabbing the can and methodically spraying my shoulders, back, butt and the backs of my legs. Finishing up, he said, "Do you mind if I use a little on my white meat?"
"Go for it," I said. He sprayed the light skin of his crotch and hips, and then handed me back the can and said, "Can you get my ass? My Sicilian skin doesn't burn, but I must have a Scottish butt!"
After making sure his butt cheeks were sufficiently protected. I put my hat back on, he resumed his pose, and we continued with the painting for another couple hours, taking periodic swim breaks.
"I think this is good for today," I said assessing the painting. I turned the board around to show him my progress.
"Looks great," Philip said. "I can't wait to see the finished product."
"I'll use the photos to do all the detail work at home. I'll make sure to delete them all when I'm done," I added.
"No worries," he replied. "You're welcome to keep them if you want to use them for another painting."
"Thanks," I said, surprised. "Aren't you concerned about other people having nude photos of you?"
"Nah. If anything ever got out, I don't have any close family left to embarrass. And, if they did, you'd be very quickly out of a very good job," he added with a wink. "I actually have some other old photos I can give you if you ever want to use them for your art. I'll dig 'em up and let you look through them sometime."
"Nude photos?" I asked.
"Yup. Old stuff from beach vacations. And some Daisy took for private fun over the years," he said smiling. "I saw some of your more erotic stuff at that last show."
"That'd be great. Thanks Philip," I said, still surprised by his offer.
"Now I'm starving. Let's have some lunch," Philip said changing the subject. As I packed up my art supplies. He headed inside and emerged a few minutes later with a tray with two plates. "I hope you like chicken salad, 'cause Daisy's is amazing." He sat down at the shaded patio table and motioned me over. I'd been about to get dressed, but seeing that he was still completely naked, I set my clothes back down on the chair and walked over to the table, still nude myself.
We had another nice chat over lunch. He regaled me with stories of how he and Daisy met and their travels over the years. After lunch, we swam for another 45 minutes or so, and then I got dressed and headed back out to my car. Philip never put his clothes back on and walked me out to the front door still naked as a jaybird.
Over the next couple weeks, I finished all the detail work on the painting. Though there'd been no sexual tension during the day we'd spent naked together, I have to admit I'd pulled up the photos of Philip on my computer monitor a few times and used them for masturbatory inspiration. In the privacy of my bedroom, I could zoom in and see every high-resolution detail of his chest and cock. Part of me wondered if Philip knew this might happen -- and actually took a little secret pleasure in it.
Satisfied with the finished painting, I took it to a nearby framing store and had it set in a thick matte and simple ash frame. Wrapped in brown paper, I hauled the large painting it into the office and presented it to Philip. He was thrilled and so was Daisy when she received it a week later on her birthday. She called me at the office to thank me. "I just love being able to see my silver fox anytime I want!" she gushed.
And now, that painting hung on the wall of the bedroom -- on Daisy's side, of course -- where I was busy packing up Philip's clothes.
I headed back down the hallway toward the laundry room to get Philip's swim trunks out of the dryer. As I passed his office, I could see that he had a porn video up on his screen and was slowly pumping his now erect cock. Besides our painting day by the pool, I'd seen him naked or nearly naked several times -- in his studio office helping him don a suit or tux for a work event or in the locker room at the studio gym. But this was the first time I'd seen his erection, let alone see him jerking it.
I tried not to stare as I passed his office. From the distance of the laundry room I gave him warning. "You should probably take a shower and get dressed soon. We're about 30 minutes out from departure."
"I'm almost done here," he said, his voice shaking slightly from his physical exertion. As I walked back down the hall, he looked up and caught my eye. "Sorry. I decided it would be better to take care of this now than be stuck with blue balls for a 10-hour flight. The mile-high club is no fun solo."
"No problem," I replied grinning at his honesty. "I've seen a few guys jerk off in brief period as an adult."
"Hah! Wow, now you're making me feel like an old pervert," he laughed.
"Believe me, I don't mind," I said honestly watching him as he stroked his cock slowly. "Now I should finish getting your stuff packed up."
"Hey Tyler," Philip said as I was about to leave him.
"Yes."
"I don't mind if you want to watch me," he said quietly.
"Really?" I asked him.
"Nah," he said. "I kinda like being watched. But I don't want it to be weird for you." I just smiled and gave him a nod as I leaned against the door frame and settled in for the show. "I'm pretty close."
I could tell he was. Beads of sweat had formed on his forehead and across his chest. His legs were spread and I could tell he was clenching his ass cheeks, which raised his cock up into the air. He spit into his right hand and lubed up his cock with his rapid strokes. He pushed his left thumb against the spot where the base of his cock met his pubic hair. It had the effect of a cock ring and made his dick swell even more. With the fingers of his left hand, he teased at his ball sack.
Philip was staring intently at the screen where some big-boobed porn star being eaten out by a man dressed as a UPS driver. "Oh yeah," he moaned. Raising his butt a bit more off the chair, I could see the muscles in his naked body tense up as semen began to shoot from the head of his cock into his pubic hair and onto his stomach. Slumping back into the chair, he quit out of the browser window, silencing the busty blond onscreen. He looked down at the white mess on his stomach and hand and smiled. "Damn, that felt good. I can't wait to see Daisy," he said smiling.
I turned toward the guest bathroom across the hall and grabbed a washcloth from the cabinet. "Here you go," I said handing it to him.
"Thanks, buddy," he said with a wink. "By the way, I pulled out those photos I told you about a few months back. There here in the drawer if you get inspired to do any more painting while you're here."
"Thanks," I said, and with a wink I added,"And thanks for the show. Now you better get in the shower."
"Yes, sir," he said dabbing at the cum with the washcloth. He set it down on the desk, stood up from the chair and headed down the hall to the master bedroom, his still firm and glistening erection bobbing along the way.
I shut down his computer and tucked it into his computer bag. I picked up the washcloth and brought it to my face, inhaling the aroma of Philip's cum. Without thinking, I stuck my tongue out and licked at one of the globs of white fluid. I set the washcloth back on the desk, hoping it might still be pungent when I returned from the airport, and hauled the computer bag into the bedroom and set it next to his suitcase.
Philip was standing at the sink shaving, still naked and still glistening in the afterglow of his jerk-off session. When he was finished, he stepped into their large sky-lit shower and turned the water on. As he lathered up his hair and scrubbed the cum off his belly in the shower, I stepped into the bathroom and organized his last few toiletry items into his dop kit.
"Can you throw this in there, too," he said, tossing me a plastic bottle of shampoo.
"Sure," I replied and made room for it in the dop kit.
"The internet guy comes on Thursday," he said over the sound of the water. "And Jerry will be here tomorrow."
"Right," I said. Jerry was a dear friend of Daisy's, a massage therapist with a flamboyant personality. He drove out almost every Tuesday from Palm Springs and serviced a few LA clients from the cabana house by the pool, and often stayed over night there before heading back to the desert the next day.
"We told him to give you a massage anytime you want, since we won't be here," Philip said shutting off the water and grabbing for a towel.
"Okay, thanks," I said.
"He can be a little 'handsy' with the guys," Philip said smiling. "Just tell him to back off if you're not up for a happy ending."
"He gives you a happy ending?" I said surprised.
"Not every time. But, you know, things happen down there when you're getting a massage," Philip said as he toweled himself off. "A hand's a hand. And he does have pretty good hands."
"Thanks for the warn... heads up," I corrected myself.
Philip finished drying himself off and hung the towel back on the hook by the shower. He applied deodorant and rubbed some gel into his hair, and then proceeded to pull on the boxer briefs, jeans, polo shirt, ankle socks and tennis shoes I'd laid out for him.
I zipped up his suitcase and rolled it out to the garage and placed it in the back of the SUV. Philip headed outside to the pool and gave the dogs each a belly rub and a final treat, and then came back into the office, locking the French door behind him. I grabbed his computer bag and his cardigan off the bed and asked, "Anything else you need?"
"Nope," he said, "Let's roll." And with that, I armed the security alarm and we headed into the garage as the door began to raise. I settled into the driver's seat, adjusting it as Philip climbed in the passenger seat next to me.
The drive to the airport was congested, but uneventful. Although Daisy had already run through all the to-dos, appointments and inventory of all the meals she'd made and frozen for me, Philip did his due diligence by repeating most of them. "You should stay in our room," he said. "The dogs sleep in bed with us and they'll be more comfortable if you're in there."
"No problem," I said.
"You're welcome to have a few friends over," Philip said. "Jerry won't care if you skinny dip. Neither will the gardener for that matter. He's seen it all by now. But make sure you're fully clothed when Lucia comes. She might turn to stone if she sees another naked man."
"I'll keep that in mind," I laughed. "Penis okay for Jerry and Ernesto. No penis for Lucia."
We pulled up to the international terminal at LAX, I put the hazards on and stepped out of the car to grab Philip's suitcase as he reached in the back seat for his computer bag and sweater. "Call or text me if you have any problems. Thank you so much for watching the pups and the house. And enjoy your little staycation at Casa Caine," he said patting me on the shoulder.
"Thanks, Philip. I hope you guys have an amazing time in France. Don't worry about anything here." With that, Philip wheeled his suitcase into the terminal and I hopped back into the SUV for the slow journey back in traffic to the house.