Ups and Downs

Bedtime Fantasy

Among Rafael, Ron, Kim, and me, we were able to rustle up enough clothes to dress up Davey and Zac pretty well. In fact, Zac looked better than any of us. He wasn’t just good looking, he was devastatingly handsome.

If Davey and Zac were thrilled to be invited to have dinner with us, they were deliriously happy to sit on each side of Mr. Block with Woody and me sitting across from them. They were good conversationalists too.

We learned that Davey was just beginning his sophomore year at San Diego Mesa Community College, where he was majoring in political science with the goal of getting his B.A. from the University of California at San Diego (UCSD) and then a law degree. “I want to use my degree to fight for the civil rights of gays and others who are too often discriminated against,” he said. “But I’m having trouble keeping my grades up,” he confessed, “because I am having to work two jobs to pay my tuition, and that really cuts into my study time.”

Zac had graduated with a degree in music from UCSD, and after dinner, he entertained us on the grand piano in the ballroom with selections ranging from Rachmaninov to Jelly Roll Morton and from Cole Porter to Elton John, all of which he played from memory. Mr. Block was so impressed that he hired Zac on the spot to perform at some events he had coming up.

The highlight of the evening for me, though, was watching Davey and Zac get dressed and undressed. If I hadn’t had to be up early in the morning, I would have been all over them.

Before adjourning for the evening, Mr. Block thanked Davey and Zac and invited them to join us again for dinner sometime. The guys must have floated on clouds all the way home.

Before going to bed, I decided to take a stroll around the pool to clear my head. The eye-candy was, as always, delectable, but my thoughts were fixated on only one person: Tyler, the hunky blond-haired, blue-eyed swimmer who had cuddled with me as I slept the night before. I just couldn’t get him out of my mind.

As I lay naked on my bed, I fantasized about Tyler appearing out of nowhere, dressed in jeans and a T-shirt. Approaching the bed, he whispered that one word that had debilitated me before, “Hi.” That’s all. But it sounded so incredibly sexy and seductive coming from his captivating lips. “I see you’ve been expecting me,” he said, inspecting my nude body from head to toe, but lingering on my ultra-stiff penis.

“Down, boy,” he said, pressing his firm, manly hand against my chest as I tried to rise up to greet him. Hell, I didn’t want to greet him; I wanted to devour him. “Don’t rush it. We’ve got all night.” All night? Thank you, God.

Stepping back from the bed, he slowly removed his T-shirt—his broad shoulders and chest and his narrow waist radiating light and heat in the shadows of my darkened room. He removed his belt excruciatingly slowly, as if to torture me with anticipation. Before removing his jeans, he spread his stance and slowly rubbed the bulge between his legs—and what a beautiful bulge it was.

He unzipped his jeans in what seemed like one tooth intersection at a time and let them flow to the floor like sap oozing from a maple tree. Stepping out of them, he reminded me of a show horse at dressage, so powerful, yet graceful. The bulge in his Trophy Boy underwear appeared massive even without an erection, which was yet to materialize.

Removing his briefs was a complete act in itself, a seductive strip tease. He pulled at the waist band with his thumbs, looked down at the contents, licked his lips, and then closed up. He turned to display his beautiful butt to me and slowly pulled down the briefs to expose only about half of his crack. Turning around again, he teased me further by pulling down one side of his briefs to expose his pubic hairs, but no farther. Then he pulled the strap back up and repeated the tease with the other side of the briefs. He turned again and bent over to flash his butt at me as he had before, but this time he lowered his briefs farther, exposing most of his bubble butt like a classic Rodin sculpture.

Facing me again, he cupped his balls over his briefs and moaned softly as he massaged them, which incited the erection I had been salivating for. Between his thumb and index finger, he massaged his manhood though the cloth as if to prove to me how long and thick it really was. Of course, I needed no proof because I had seen and experienced it the night before during my initiation. Yes, it was big. Not huge, but more than big enough to do the job, which he knew how to do very, very well.

Sliding his hand inside his briefs, he continued to stroke his penis until I was sure it would break through the cloth. Without removing his underwear, he inched toward me, climbed up on the bed, straddled my chest, and rubbed his basket in my face. I licked the enticement until it was soaked with my saliva, giving me a semi-transparent peek at the meat sizzling inside.

He pulled the strap forward and pressed it between my teeth, coaxing me to remove his briefs with my mouth only, which I was more than happy to do. Just to make sure I didn’t cheat, he held my hands over my head, trapping me with his powerful grip.

Once I had completely removed his underwear with my teeth, he slid his dick into my mouth and pumped like he was waltzing his way to the promised land. When I sensed his magic elixir bubbling up from his balls, he pulled out, and without saying a word sank his tongue where his dick had been, kissing me passionately, commandingly, as if to make sure that I did not resist, which, of course, I would never have done even if I weren’t so totally overcome.

He kissed and licked his way down my chin, neck, and torso until he reached my dick, which had been aching for attention, but instead of taking it into his mouth, he licked it several times and moved on to my glory hole, which he tongue-fucked until it was drenched in his saliva and my anal juices.

When he slid his rock-hard penis into my hole, it hurt like hell, but I relished the pain. “More. More. Give me more. I want all of you.” And that’s exactly what he gave me. Despite the length of his pole, I still felt his balls slapping against my butt cheeks as he thrust harder and deeper. At that moment, the only thing I wanted deep inside of me more than his man tool was his man seed.

When he exploded, he grunted and moaned, the heavenly music of ecstasy in the ultimate union of two men in love. At the same time, my own dick blasted what seemed like gallons of my own love juices.

Much to my delight, he never pulled out. In my fantasy, he fell asleep on top of me, where he remained all night, my cum acting like Gorilla Glue binding us for all eternity.

Of course, it was all a fantasy. It was not a dream because I had not yet fallen asleep, but when I opened my eyes, I found my face and body covered in my own spooge. I had achieved an orgasm without even touching my private parts. Rather than get up and wash it off, I decided to leave it, falling asleep with the fantasy that my cream was his body cuddling, protecting me all night.

The next morning, after showering and washing the dried cum off of my body, I threw on some clothes and ran downstairs to grab a hearty breakfast before my meeting with Woody. In a way, I was glad I had spooged the night before; maybe that would keep me from getting an erection while sitting so close to Woody.

“Uh, dude. What the fuck are you doing?” Raphael ask as I sat down at the breakfast table.

“What?” I asked.

“You can’t go into your meeting dressed like that. No go back upstairs and put on something business casual, maybe what Zac was wearing last night.”

I didn’t see anything wrong with what I was wearing, but I did as Rafael instructed and still got back in time to scarf down the eggs, sausage, hash browns, and blueberry pancakes that Kim had served up.

In our meeting, Woody gave me the dates for our trip to the East Coast, which included a couple of days in New York City before our train ride up to Greenwich and a couple of days afterwards. “Mr. Block and I have other business to take care of,” he commented, “and while you’re doing that, you and Rafael can make fools of yourselves in the Big Apple.”

“Thanks,” I grinned, anticipating what we might do during our free time.

“You will make all of the reservations,” Woody directed. “Flights, hotels in both New York and Greenwich, train tickets, and whatever else we might need.” And with that, he handed me one of his credit cards. “Let me know if you have any questions as you proceed.”

I assured him that I would as I pulled out my sketch pad to take notes.

“You don’t have an electronic tablet?” he asked. When I assured him that I did not, he turned to the credenza behind his desk, opened a cabinet, pulled out several devices, and handed me a Wacom Cintiq. “Here,” he said. “This one works well for notetaking, but it’s also the best tablet on the market for sketching. If you have any questions, ask Ron. He’s familiar with this one.” Wow, you thought about my interests as well as your own needs. That’s comforting.

“Now go make sure that Rafael has gotten the Navigator ready. I’ll meet you out front. And bring the tablet with you. You might need it.”

“I’m going with you?” I inquired.

“You’re the reason we’re going out,” he said, throwing me for a loop. When I stared at him with question marks all over my face, he replied. “You’ll see. Now go.”

I found Rafael out front with the Navigator all set to go. “Where are we going?” I implored.

“Woody hasn’t said yet,” Rafael shrugged. “The fact that he asked for the Navigator rather than one of the other vehicles gives me a pretty good idea, but—”

“In the second row with me,” Woody snapped before Rafael could finish his comment. He just winked at me, slapped me on the butt, and said, “All aboard.”

As it turned out, we spent the whole day shopping, which is one reason Woody wanted the large SUV—plenty of room for packages. The Lincoln also had more leg room than some of the other vehicles, and Woody was about 6’4”, give or take an inch.

During the ride to our destination, Woody asked, “So, Joe, what do you think of our automobile fleet?”

“It’s very impressive,” I acknowledged, “but I’m wondering when I’m going to get my own car back.”

“How old is that car, Joe”

"It’s about 12 years old, but I’ve only had it for a couple of years. It still runs good, though.”

“Yeah, but you don’t really need your own car here, do you? I mean, you can take one of our cars any time you want, so why not sell your old car and save the money for your retirement?” he joked.

“I suppose I could,” I replied, “but who would want to buy it?”

“If you’d like, I can arrange that for you.”

It all seemed a bit strange, and Woody was definitely strange…but in a very good way, so I decided to trust him and agree to the sale.

Twenty minutes later, we arrived at a very large mall and went into a Brooks Brothers store. “Mr. Woodward," perked up the manager as we entered the store. “So nice to see you again,” he gushed in his mellifluous French accent. “You need another suit today?”

“Two of them,” replied Woody. “One for each of these dashing young eligible bachelors.”

Rafael and I glanced at each other in amazement. “You’ll need one for the trip,” explained Woody, “and you,” he pointed to Rafael, “will need one for your new job.”

“But I already have—”

“I know,” interrupted Woody, “but you will need another one. The one you have is good for business, but you also need one for more formal occasions. After all, you are a management trainee, and you will be a full-fledged manager in no time.” Rafael beamed at the vote of confidence.

François, the store manager was a handsome man, only slightly older than Woody I guessed, and nattily dressed, of course. He had to be dressed impeccably in order to make the proper impression on the customers.

He led us to a section of the store that featured men’s business suits. I spotted the price tags on some of the suits and drifted toward the less expensive ones, which were still many times more than I could ever have imagined spending for a suit. Every time I would pull a suit off the racks, though, Woody would grab it and put it back. After the third try, Woody turned to the good-looking manager and said, “François, would you please help this country bumpkin. He’s going to be a real asset to us when he has learned the ropes, but he has no fashion sense whatsoever.” Was that a back-handed compliment? Rafael laughed like crazy. “You’re not much better,” Woody scolded Rafael. We all knew that was not true, but I think Woody was just trying to make me feel like I wasn’t quite so bad after all.

“Now that’s what I’m talkin’ about,” exclaimed Woody when he saw me in the $1400 three-piece suit that François had picked out for me. And while Woody went to check up on how Rafael was doing, François took my measurements. Actually, he took more than my measurements. As he measured my chest, he rubbed my pecs a bit longer than I thought was required, and when he measured my inseam, he lingered around my crotch.

“How does that feel?” he asked, and I was sure he wasn’t talking about the fit of the pants.

Under other circumstances, I might have been outraged, but since he was undeniably cute, I simply said, “That feels just fine. You’re very good at this”—meaning the job of course.

Staring at my crotch when I removed the pants, the French tailor stated, “We close at 9:00. When you come back to pick up your new suit in three days, perhaps you would like to come by just before closing time.”

“I’ll see what I can do,” I replied as I cupped my balls and adjusted my junk to tease him.

To be continued..