The New Guy In Town

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.

He raised his ass and felt Mike's rod at his opening. The first moment of penetration brought a twinge of pain, but also a feeling of completeness. There was an underlying pleasure that came with that pain. Then he was being filled. It felt like Mike's cock was a foot long as it entered him. There was still pain, but the pleasure was incredible.

His eyes locked on Mike's. "Oh my god, you're fucking me! I'm being fucked! Your cock is in my ass! Oh my god!

"Is it good?"

He nodded, barely able to speak. "It's incredible!"

Mike wrapped an oil-slicked fist around Anthony's thick love root, and began to jack him off in rhythm with his gentle thrusts. He smiled when he felt the younger man's sphincter begin to pulsate around his shaft. The eruption of cum that followed was glorious. When he was done cumming, Anthony's belly was covered in gorgeous jizz.

Anthony's look of ecstasy was suddenly replaced with an expression of alarm. Mike slid his cock free and laughed. "In there." he pointed with his chin to the bathroom.

When he was done sending a modest stream of urine into the toilet, he turned to go back to the bedroom. The back of the bathroom door had a full length mirror, and he saw himself. It made him pause. Did he look different, now? Other than the fact that his chest and belly were covered with several strings of silver cum, he didn't seem any different. His butt-hole did, but not in a bad way. It just had a slightly uncomfortable numbness. If the price of an absolutely mind-blowing orgasm was a slightly uncomfortable asshole...no, fuckhole, well, the choice was pretty easy.

Mike was laying on his side, propped up on an elbow. His manhood was still magnificently stiff.

"You didn't cum." A statement, not a question, as the older man slid across the bed towards him.

"No, but that's okay." Mike replied, reaching a hand around behind Anthony as he stood beside the bed.

"But I want you to cum in me. I need that, so I can really feel that I've been fucked by a man."

Mike ran his tongue languidly up one of the strings of man-cream on Anthony's belly, then looked up at him dreamily. "I'll make you good and hard. And I'll cum inside you just like you want. And I'll make you cum again." Another lick, this time lapping up the little puddle that had formed in Anthony's navel. "You get on top and straddle me. Then you can control how we fuck."

Anthony did as he was told, after Mike poured a big dollop of lube into his hand so that the younger man could slick up his mentor's shaft.

Anthony guided the cock between his cheeks and settled some weight on it, enjoying the slight pressure at his entrance. Slowly, gently, he lowered himself, letting his lover's sceptre pry open his muscle. He gasped when the full cock-head slipped in. The slight pain was leavened by the intense pleasure that the pressure created. Now he needed to feel it deeper. Then deeper again. Before pressing his lover in full depth, he bent down and kissed him. The taste of his own jizz in the man's mouth spurred him to take Mike balls deep.

He adjusted his position until he could move his hips up and down on the man's shaft. Rose until it felt like the cock was about to slip out, then slid his sheath back down the length. The feeling of being filled, and the attendant pressure, then the easing of the pressure as he moved upwards was fantastic.

Mike helped to guide him up and down, finding a rhythm. Anthony watched with rapt fascination as Mike's expressions moved from that of attentive lover to that of a man focused on the climax rising in his manhood. Anthony grabbed his own stiff cock and began to jerk himself off. His own ecstasy was spurred on by the raw eroticism that was the realisation that he was truly being fucked. That he was close to having his insides anointed by the orgasmic fluid of another man.

Mike thrusted hard, and moaned. His cock spasmed and twitched as he pushed his rod and his seed deep inside of his lover. Anthony responded by shooting more streamers of love cream out and on to Mike's belly and chest.

Anthony stopped moving. He realised there was a discomfort that came immediately post-climax, but he managed to ignore it. He liked feeling Mike's post-orgasmic twitching inside him. He playfully licked up one of the ropes of jism that adorned Mike's tanned chest, then kissed him. Then he quickly extricated himself and jogged to the bathroom again, where he dribbled a much smaller stream of piss into the toilet. He had a slight moment of alarm when he felt a warm dribble down his scrotum, but a glance at his fingers after touching the fluid made him smile. Just Mike's cum.

They laid together in bed, enjoying the afterglow.

"Do you only fuck guys?" Anthony asked.

"Yeah. Last time I fucked a woman was five years ago. And she came on to me because she knew I fucked guys. Good looking woman I worked with. Came in my office one day after everyone had gone home. Told me that she heard that I liked to fuck other men. Don't know how, but she had. Then she bent over the desk and begged me to fuck her in the ass, because her husband wouldn't. So, I did. About once a month for a year, actually. She always wanted it in the ass, and I was happy to do it."

"But, like, do you just fuck other guys, or do other guys fuck you sometimes?"

"Oh god. Down here, it's a smorgasbord of fucking." Mike shifted so they were a bit more face-to-face. "Some guys, like me, go both ways. I like getting fucked, about as much as I like to fuck. Just depends on what's happening. Some guys don't fuck at all. They only suck cocks. There's even the odd guy who only wants a blow job, as long as it's a guy's mouth doing it."

He shrugged. "Then there's guys who only want to be fucked. A couple of times I've hitched up with guys who really want to get fucked. I think it's a chemistry thing. And when the chemistry's really good, it's really good. Two, three days of lazing around the house with a guy who's attitude is 'you get that thing hard, I've got a place you can stick it.' Then there's the flip side. Some guys will only fuck, and not get fucked."

"Is there a lot of guys down here just looking for someone to fuck, or suck?"

Mike laughed. "Like I said, it's a smorgasbord down here. There's lots of guys to choose from that live here, plus a steady stream of vacationers. And that hotel clerk? You cum in his mouth, and he'll cum all over himself. Just a month ago, he introduced one of the guests to me. I gave him a really good tip for that. I fucked him twice. And sucked him off. The guy that he introduced me to was a real stud. Our chemistry was wild, and I was the guy who spent three days getting him hazard so that I could give him a place to stick it.

The best times are when you connect with some stud, and the chemistry clicks, and you spend a couple days together, and every time you get hard, one of you has a hole ready. Either a mouth or an asshole, and you just fuck and suck each other until you simply can't even think of getting hard."

Anthony reached down and made sure he was feeling what he thought he was feeling. Mike's cock was thick and hard against his thigh. He kissed him, again thrilling at the taste of his spunk on the other man's lips and tongue.

"I'd like you to fuck me, now." Mike whispered between the tangling of their tongues. He turned away and raised his ass. He used both hands to spread his cheeks. "Lick my asshole. Stick your fingers in me. I want you to feel what a man feels like on the inside."

Anthony had never thought about licking a man's fuck-hole before, but the pink knot of flesh, that he couldn't take his eyes off of, drew him in. He licked it. Probed it with his tongue. That alone was so infused with the excitement of forbidden erotica, it almost made him cum. At Mike's instruction, he lubed his fingers and slipped one inside.

The thrill of touching, and penetrating, another man so intimately was intoxicating. As intoxicating as the feeling of Mike's thick rod stretching and filling his hole had been. Mike shifted, pushing his ass a bit higher. He reached back with both hands and spread his cheeks wider.

"Now mount me. Shove that big cock of yours in me and give me some good fuck!"

Anthony straddled the older man, then pushed his cock against the the puckered circle of flesh. He pressed gently, and the purple head was swallowed. Then Mike pushed back and he was balls deep inside a man! The feeling of being en-sheathed by Mike's body sent a thrill through every nerve in his body. He was fucking a man! A strong, beautiful, and virile man! And he followed his instinct, which was to fuck. And he began to pump his cock in and out of Mike's pleasure hole.

"That's it, fuck me big boy! Fuck me hard! Give me some of that hot jizz!"

And he did. For the third time that night, Anthony's cock pulsed with orgasmic pleasure and he drove his seed deep into this lover he had found. And the feeling of cumming into another man was more than just raw physical pleasure. It made him feel powerful, as well. It made him feel as though he was cumming right from his toes.

He fell away exhausted, and Mike rolled to his back. Anthony saw that he was still hard.

"I didn't make you cum?" he asked, disappointed, and a bit puzzled.

"I was getting there, but you were a bit quick." A smile. "That's okay. You're young. You get some miles under your belt, you'll be fucking like a pro."

Anthony reached across and gripped the swollen shaft. "I want to make you cum. Do you want to fuck me again?"

"No. Jack me off. You can watch me cum. I'll bet you've never seen a man squirt before, have you? And I like it when a guy watches me squirt."

Anthony slid down a bit, and Mike poured another squirt of lube on himself. Anthony dreamily ran his hand up and down the rigid muscle, loving the feel of it in his grip. And was soon enough rewarded with several spurts of thick, creamy love juice that landed in streams arrayed across Mike's belly. He smeared the liquid around with his hand, fascinated by the feel of it.