Anthony used the drive south to reflect on his life and good fortune. He had long known that he was different, but it never weighed him down. It wasn't in his nature, really. Nor had his lack of romantic partners for the entirety, so far, of his adult life.
Not that it been a complete desert, even if a bit deceitful. Every once in a while he brought some pretty girl home for supper with the folks. And every once in a while, one spent the night in his apartment. The sex was usually pretty good, but it wasn't what he was looking for.
He focused on work. His family connections, and college grades had ensured that he started at an accounting firm that had broad opportunities. His talent and work ethic ensured that the pay was better than just good.
Uncle Edwin had provided inspiration, and a great incentive, to finally get on with the business of living. Edwin was a life-long bachelor, but one with a veritable posse of charming and charismatic male friends, with whom he travelled the world on many adventures. Edwin, who had started out in law, made some real money on some real estate deals, and semi-retired young, had taken Anthony aside when he was just starting college.
"Don't get distracted chasing tail at school, Tony. Stay focused, and ten years from now you'll be able to chase all the tail you can handle. We Flynn men don't always have long time lines, but we're damn good at making other people money. Which makes us money"
Anthony took the advice. Five years later, Edwin had asked him how his fortunes were progressing. Anthony had given him the abbreviated version, and the numbers had pleased Edwin immensely.
"Four or five years from now, you'll be chasing tail in Key West, my young man. Good for you. When it's time for you to go down, there's a place I like to stay, and some friends you can look up. They'll introduce you to all the right people."
Edwin, ten years senior to Anthony's mother, only made it four more years. His canoe had overturned on a paddle trip in Vermont. The water he aspirated had led to a lung infection, and he was gone. But, he left Anthony $150,000 in his will. Enough to justify taking a three-month leave from the firm, and a Hartford winter.
He drove down, in his brand new 1969 Corvette, in the first week of January. He only had a vague idea of what was going to happen down there. His uncle had mentioned a classy hotel that catered to, as he had only once put it, "our crowd." He hoped that it meant what he thought it meant. After all, the Flynn's were rather decorous. Some things were only discussed in oblique terms. The way Anthony figured it, Uncle Edwin was quite aware of his nephew's sexual desires. Family, and societal, decorum meant it was discussed rarely, and very delicately. Anthony figured Edwin had handled it well, and steered him right. For that, he was thankful.
He only knew the hotel was on Trumbo Point. The highway almost led him straight to it. The hotel was a very well kept but old-fashioned building, looking to be from the 1920's. Walking in, the check-in was to the rear of the broad lobby. A dining room was on the right. A piano bar on the left. It was midday, and a Wednesday, so it didn't surprise him that both were near empty. The only people in each were men, so he assumed that he had caught Edwin's hints properly. Checking in was smooth. There were a number of rooms available. The clerk suggested a room overlooking the pool. Along with the room key, the clerk handed a business card.
"If there's anything I can assist you with, Mr. Flynn, I'm available at all hours."
There was a very subtle emphasis on "all." That made Anthony smile. The clerk was easy on the eyes, and close to his age. Probably no more than three or four years older.
The view of the pool was all he had hoped it would be. A dozen men lounging and swimming casually. A few had clearly been working on their tans. All were lean and various degrees of muscular. The view made a certain part of his body twitch.
Anthony spent the next two days just being the quiet and reserved guest. He didn't forsake the pool area, however, and enjoyed the conversation and attentions of his fellow guests. The attention was definitely sexual in nature. He knew he was very good looking and could probably have his pick of any of the men there, but he was looking for something, someone, special.
He found that man on Friday afternoon, sitting in the lounge, enjoying a drink by himself. Mike was forty-ish, with a little salt sprinkled in his dark hair. The tan looked semi-permanent. It was, it turned out, because Mike spent most of the year in Key West. There were occasional trips up to Baltimore to handle real estate matters that couldn't be dealt with over the phone. He had done well in that regard, before moving down to the Keys, he explained. A little application of talent had also allowed him to have some Florida income, too.
Anthony gave him the condensed version of how he came to be able to afford an extended stay at this rather expensive resort. This was followed up by the question of where Mike stayed. The hotel?
"No, I have my own place a few blocks away. I like to wander over here for a cocktail, and to meet people. I find that the eclectic clientele here can be very interesting company."
"Do you find me, interesting, Mike?"
"I do. You seem like a young man with a somewhat hidden purpose. May I ask what that might be?"
Anthony looked around, almost shyly. There were other men in the lounge, but none close. He leaned close. And whispered. "I'm looking for someone to teach me how to have sex with men. You seem to be that kind of man. Can you teach me?"
"You've never had sex?"
"Yes," he replied with a shy smile, "Just not with a man. But it's what I want."
Mike nodded thoughtfully. "How about we continue this discussion at my place? It's quite nice, and maybe a better place to lose your virginity than a hotel room, even one as nice as this."
They finished their drinks casually and congenially, then enjoyed the pleasant evening air for the ten minutes it took to walk to Mike's bungalow.
The house was a modest place, set back from the street. Anthony saw that it was immaculately trimmed, and the back yard featured a high fence and a pool. The house was also uniquely set back from the street, affording both the entryway and the back yard an extra level of privacy. He suspected this allowed for outdoor escapades during the warmer days of spring and summer. And maybe even winter.
The inside of the house was modernised from its WWII-era roots. Mike waved a hand expansively, and suggested Anthony make himself comfortable on the big sofa. He disappeared into the kitchen and returned with two glasses of wine. After setting down close, Mike kissed Anthony full on the mouth. The act surprised Anthony, but only for the briefest of moments. The feel of Mike's tongue in his mouth made him rock hard.
Half an hour later, Mike held out a hand and led Anthony to the bedroom. The room featured a massage table and a king-size bed. As Tony took it all in, Mike removed his shirt and stepped out of his pants. When Anthony saw him naked, his first thought was "He's beautiful." Then "His cock is even more beautiful."
It was the first he'd ever seen. Well, the first time he'd ever seen another man hard and openly proud. Ready for making love. Ready to fuck. He stepped close and reached out. When he touched the man's love flesh, an almost electric thrill passed through him.
"Teach me." He said, and they kissed again.
Mike undressed the younger man carefully, then instructed him to lie face down on the massage table. At that point, Anthony was trembling with nervous excitement. Enough so that he was a little concerned that his reliably virile shaft was not expressly as rigid as his new lover's.
Mike took no heed, and began to gently rub massage oil into Tony's back and shoulders. Eventually the massage moved to his buttocks. He was surprised at the eroticism of having his butt cheeks massaged. Then Mike's skilled hands moved down his legs. Thighs, calves, even his feet were knurled and rubbed.
The first truly sexual touch was a gentle rub of his scrotum and perineum. Anthony moaned and spread his legs a bit. Then a thumb gently circled his anus. That gentle touch became more firm and massaging. he gasped a bit when Mike slipped a finger partway into his opening. More massaging of back and thighs led back to that special place. A little more pressure to the massage, and then a deeper penetration with an oil slicked finger. It was an unexpectedly different sensation, but a good sensation. This was repeated several times until Anthony felt himself craving the moment of penetration.
He expected Mike to simply mount him and penetrate him, face down. Instead, Mike helped him up and guided him to the bed. Now Anthony was hard. Rock hard.
"You have a beautiful cock." Mike said. "I can't wait to watch you cum."
Tony went to his back on the nest of pillows. Mike knelt between his legs. More oil. More massaging. Chest, abdomen, thighs again. The occasional probe of what was soon to be Anthony's love opening. Mike oiled both their cocks, the sensation of another man's hand on his rigid tool almost sent Anthony over the edge, but Mike skilfully pinched his cock-flesh and stopped the rising explosion.
Finger explorations of his anus became a thumb, fully inserted.
"Do you like that?"
Anthony couldn't speak. All he could do was nod.
"Now, I'm going to slip into you. Slowly." His tone was gentle and loving. "You'll probably cum pretty quickly, but you'll probably have to pee right after. Don't be embarrassed. Just get up and go."
It was something that had never occurred to Anthony, but he wasn't stopping to think about it. There was an orgasm building up inside of him, and he wanted this one to happen with a man inside of him. He had known for too long that he wanted to fuck with men, and this beautiful man was about to shove his thick cock into his virgin hole and he couldn't stop to think about some of the hitherto unknown aspects of man-sex.
