Country Club Stud

This story was inspired by jhtravus’s “Country Club Prostate Masseur”

It wasn't hard to get a caddying job at other clubs, but East Hills Country Club had a very well-to-do membership and had the reputation for having big tippers. I had a leg up being on the Canton High golf team for a few years, and with a prior summer's experience caddying at my dad's (less exclusive) club. And Dad's boss Dave Powell, an East Hills member, knew of an opening at the club and put in my name to the staff. A week later I got a call and an interview.

So, yeah, I was pretty lucky, since I was heading off to college at the end of summer and could use the spare money. I even started in April, on the weekends, to learn the ropes and build up a clientele before summer hit. Adam, one of the older caddies, who I'd guess was about 25, gave me my orientation, which included a tour of the course, information about the clientele and club etiquette, and my uniform of a forest green polo with the club logo and a white baseball cap, which I was to wear with neat, pressed khaki shorts. "Don't forgot the sunblock," he added. "I got burnt to hell my first weekend out."

It was cool to have an older brother figure show me the ropes, but I wasn't prepared for the last bit of advice. "One thing I have to emphasize is that this is a pretty exclusive club."

"I gathered," I said. I wondered why he was telling me this, but I figured it was part of the pep talk for the caddies.

"I mean," he explained, "you'll see lots of stuff. All sorts of behavior, actually. And you gotta keep it to yourself. No blabbing, no gossip. Keep that in mind and you'll do well."

"Got it," I said. I'm sure my eager beaver attitude was annoying as hell to Adam, but he just nodded and looked at me carefully, trying to read me.

"There's more," Adam said, lowering his voice a little and looking around. "Um, some of the men might hit on you. Married guys, too, guys you wouldn't expect. It can be great for your tips, but if that's not your scene, just deflect their advances."

I blushed, I know. Sexually I was still figuring myself out. I'd dated some girls and had lost my virginity to Susan Conrad and then had a couple of other experiences. But my experience was limited. While I hadn't done anything with a dude beyond some early teen show and tell on a camping trip, I had jerked off to gay porn videos. First, with fascination, then with increasing interest. Of course the men in those were all young lithe porn models, not suburban middle-aged men.

Adam saw my discomfort and gave me a playful half-punch to my arm. "That's cool, man. I just wanted to warn you. Remember, though, keep your lips sealed about that stuff. If it becomes a real problem, go see Mike," he referred to the club's assistant manager. "I don't think it'll come to that. The members know the rules."

With that advice, the next weekend I had my first caddy job, a pick up for a last minute cancellation. It was a great weather, and it was for two buddies who had a standing Saturday tee time. They tipped well, and it was an easy 150 bucks.

I quickly learned not to expect the job to go that smoothly. Summer heat hit early in May that year, which made carrying the bags and being under the sun exhausting. And I had a string of asshole members and lousy tippers. Guys who got a power trip by bossing me around and yelling at me for suggesting the wrong club. Men who wouldn't make eye contact with me, in order to show me my place. I grew a thick skin fast.

One benefit was the exercise. I had been pretty athletic in high school and had regularly trained at the gym, and porting bags was adding muscle to my 5'10" frame (actually 5-9-and-three-quarters, but I rounded up). Dad even noticed and commented on it one night at dinner. "Looks like they're keeping you fit at the club, Matt," he said.

I did examine my young body in the mirror that night. I did look great, I had to admit. Muscular but trim and lean with an eight pack that was readily visible given my smoothness. The fact that I had classic boy-next-door looks, blue eyes, and light brown hair gave me a certain confidence about myself. I had taken Adam's advice about the sunscreen and wore it religiously. Even so, my face, arms, and legs were chestnut brown, giving me a major farmer's tan.

Fortunately I had a few more laid back members to caddy for the next couple of weeks, and my increased familiarity with the course meant I was getting better at the job. A month and a half in, and Adam's warning hadn't come to bear. So far, none of the members had hit on me. I had been nervous that would happen, particularly since some of the guys weren't especially attractive or in shape. I had memorized my "no thank you, sir" rebuttals, but hadn't had to use them.

My guard was down, though, and the first time came when I least expected it. Ed Cahill was a senior VP at a Fortune 500 company. Mid 50s, I'd guess, but good looking in that executive sort of way. Tall, trim, mostly white haired with WASPy good looks. He played golf really well and was very serious about his game. He talked with his partner but didn't have much to say to me, beyond a distant but polite word here and there. I didn't take it personally. Like I say, I had experience with far worse and learned to do my job without much interaction. Some members were chatty. Mr. Cahill was not.

So I was surprised when he was the one who came over at the end with a couple of hundred folded in his hand. Which he placed in mine. "Excellent job, Matt. Maybe you'll be free next time?"

"Yes, sir," I said. As the new guy and the youngest, I still didn't have more than one regular and was doing pickups, though those kept me busy.

He gave me a smile and a wink and shook my hand. Then he walked off to the club house.

I had another duo to caddy, husband and wife, so I had to go on for another 18. It was later in the afternoon when I wrapped up. I was sweaty and wanted to shower, but I always waited until I got home. So in the staff changing room, I took off my cap and gave my face a quick splash to rinse off the sweat and salt and dried off with a towel. Putting my cap back on, I grabbed my wallet and keys out of my locker and headed out to the parking lot.

I was about half way to my car when a Range Rover pulled up beside me. The window rolled down. Ed Cahill's sun-tanned face appeared with a bright expression. He was definitely in a chattier mood now. "Thanks again for a good job today, Matt," he said, his face friendly and open.

"My pleasure, sir," I said, stepping toward the window. "See you next week? Or week after?"

"You bet," he said. Only he didn't roll up the window and drive off like I expected. Instead, his eyes lingered on me, and his fingers tapped the rim of the window. "You interested in earning some more today?"

My heart dropped. Shit. I had mentally prepared myself for this moment, but now that it was here all that was out the window. Thankfully, Cahill read my shock for incomprehension.

"Why don't you get into the air conditioning here? We can talk about it?"

"Sure," I nodded and walked around to the passenger side. I could have said no, but he hadn't actually asked for anything. Maybe it wasn't a good idea to get in his car, but a part of me was curious. I hadn't pegged Mr. Cahill to be gay or even interested in guys. Willing myself to act as if everything were normal, I opened the door and climbed in.

The cool air inside did feel great, and the man's smile put me at ease some. He'd clearly had a few drinks at the club house, and I could smell the alcohol on his breath. Probably he shouldn't be driving, but he wasn't smashed or anything.

"Mind if we drive on a little? I can bring you back to your car," he said, looking at me expectantly for permission.

"Sure," I said, leaning back into the comfortable leather seat.

We drove on, and Cahill kept looking over. "You're a good looking young man," he said, in his clipped WASP voice, like he was from New England or at least Ivy educated. "Clean cut."

"Thanks, sir," I said. I mustered the courage to look back at him, eyes meeting. I smiled, nervously and he smiled, too, and placed his hand on my bare knee. He had a nice strong hand. A man's grip.

"Have you ever had a blow job?" The words that would change my life.

"No sir." I hadn't either, despite my ham-handed attempts to request one from my girlfriends.

His fingers gave a small gentle caress of my leg, which sent electrical currents to my dick. I was nervous as hell but getting an erection.

He flicked on his right blinker and we were turning into a state park. "I'd like to give you one," Ed said. His brown eyes were on the road as he guided us to a deserted part of the park, but he looked over, waiting for a reply.

"Um, sure," I said, in a response that felt immediately stupid.

Cahill gave a gentle pat to the knee before withdrawing his right hand to pull the car into park and turn it off.

He unbuckled, a slight eager grin on his face, and I followed suit. His eyes were on me but mostly they were on my crotch, which was pretty hard now. "You look like you have a big dick," he said, reaching over to undo my belt.

"I dunno," I gulped. I felt stupid. All the hardons I'd seen were in porn, and I guessed I measured up to normal.

He seemed to know how not to go too fast so I'd be scared off, but he was skilled in undoing my shorts and peeling down my briefs.

"Fuck..." he whistled. "You're a big boy all right." Gingerly he stroked my hardon as he pulled it out. I was going from pretty firm to hard as nails and my prick stuck up from my open fly. "I'm gonna love sucking you." It was a trip to see this older successful man so enthralled with my endowment. "Lower your shorts," he urged, and I did, letting my shorts and briefs slide down to my ankles. I worried what would happen if someone discovered us but I had to figure Mr. Cahill knew what he was doing.

His fingers gave a couple more strokes to my boner, teasing it some, then he leaned down and took the head in his mouth.

My first blowjob, and it exceeded all expectations. The sensations, the pleasure, on top of the excitement of watching this good looking silver-haired man giving me head. Mr. Cahill knew what he was doing. He started with regular bobs before going deeper, almost deep throating me, before backing off to bathe my balls with his tongue.

"God, even your nuts are huge," he sighed before licking his way back up my stalk and plopping my cock back in his mouth. He went for the kill now, rapidly suctioning my dick and working to get me off. I couldn't hold back. I grunted out a "Mr. Cahill," in warning then my dick spurted its heavy load into his mouth. It was an intense cum, and I knew my sperm was pumping out in heavy gushes. He sucked me dry and swallowed every drop.

When I was done, he sat up and leaned back in his seat, jerking his own meat with just a few strokes until he came into his own hand and then sighed in relief.

"Mind getting me a Kleenex out of the glove compartment?" he asked.

I nodded and as he wiped off, I pulled my shorts back on. I couldn't believe I'd just had my first experience with a man. It wasn't romantic, but it wasn't like a porn video either. This was real sex and it was hot as hell.

Mr. Cahill was no nonsense after that, and he started the car and drove me back to the club. We even made small talk and he asked me about college plans and my time on the golf team. It was only then that it sunk into me that the man was almost 40 years older than me. I wondered what kind of perv I was to be getting blowjobs from old guys like him. Then I thought about what kind of perv he was. Still, it didn't take away from my excitement at a sexual milestone.

"Here you are, my young man," he said as he pulled up next to my used Toyota. I was about to get out, when he stopped me. "Wait a minute," he said and I turned to have him push a wad of bills in my hand. "I take it you can be discreet, Matt?"

"Oh yes, sir. And thank you, that was awesome."

He smiled. "Thank YOU," he countered, his eyes looking at me intently again. "You're going to make someone very happy with that cock."

I laughed at the absurd forwardness of his statement and fortunately he laughed too. I gave a friendly wave as he pulled off, feeling happy to have had my first BJ. It wasn't until I got into the car that I unfurled two crisp fifties. Holy fuck, I thought.

****

Word got around quickly. That's the only way I could explain the number of requests I had for the following weeks. My schedule started to fill up. Wednesday was a group of three friends, all very fit and muscular business men in their mid-to-late 30s. I'd guess in sales. Fortunately I had to carry only one bag, Mitch Ellis's. Unlike Cahill he was the chatty, backslapping type and I warmed to him immediately. It helped he was good to look at. Perfect teeth, bright smile, well-groomed dark hair. Filled out his golf shirt with bulging muscle. In the back of my mind I imagined what it would be like to have Mitch hit on me. My encounter with Cahill had definitely opened a new world for me and fired up my sexual imagination.

I didn't really expect anything, though, until at the end, when he gave an opening. "My wallet's in the locker room, Matt. Mind coming with me so I can give you your tip?"

"No problem, sir."

"It's Mitch," he said with a smile and gentle nudge to my arm. "I get enough of that sir business at work."

"All right, Mitch."

We got back to the locker room. "I can wait outside," I said. There was no prohibition from us caddies entering the main locker room but we had our own changing room and I didn't want to overstep any lines.

"Nonsense," Mitch said, patting my back and ushering me in. "I'll get you your money."

I stood awkwardly while the man opened his locker. He reached in for his wallet and pulled out some cash. I knew better than to count it in his presence. I just thanked him and stuffed the bills in my pocket.

He held his wallet and fished out some extra bills. "Want to earn some more?"

"Maybe," I said. My heart pumped again, double time, but this time it was more in excitement about what might come than in apprehension.

He peeled off his shirt. Damn he looked fine. All muscle, and just the right amount of hair. He gave me a coy look and examined our surroundings. He stepped up to me and whispered, "I hear you're hung like a mule."

I guess discretion goes only one way, I thought, knowing Cahill had talked. No blushing this time. The idea this stud was potentially into my dick was a real fucking turn on and ego boost. I nodded. "Pretty much." I took a chance.

Mitch smiled, amused by my cocky turn and undid his shorts. He slid out of his boxer briefs and wrapped a towel around his midsection. Picking up a couple of small tubes, he walked past me. "Follow me."

I did, to series of cabin like rooms that were private. I'm not sure what purpose they were supposed to serve, massage rooms I think. We stepped in and shut the door. I removed my cap and peeled off my shirt while Mitch sat down on the padded table and watched. "How old are you?" he asked.

"Eighteen," I answered. I was going to ask if that was a problem, but I was getting horny and I didn't want to hear him call this off.

That seemed to be the last thing on his mind as he ran his hands up the sides of my flank, giving me goosebumps. "Damn, you're hot. Great body. You work out?"

"Yeah," I answered. Hearing this guy praise me egged me on, and I undid my khakis. In no time I was stepping out of them and my briefs.

"Wow," Mitch gasped at my size watching my dong swing back and forth as it hardened up. "Ed wasn't exaggerating." He leaned forward and gave my prick a quick kiss before pulling back to stare at it some more. My dick continued to grow and stiffen. "If anything he was selling you short, Matt."

"Thanks, man," I said. To be honest, I wasn't sure what I should say in the situation. I just knew I wanted Mitch's mouth on my dick.

Mitch looked up at me, with brown puppy dog eyes, looking younger than his years. "You ever kiss a guy?"

Another first, but I wanted it. I leaned down and met this hot man for a heated kiss. His lips parted and instinctively I knew I should slip my tongue between them, so I did. It was an incredible rush. Different from a girl, that's for sure.

"Nice," he said softly as we finally pulled apart. "Ready to have this monster sucked?"

"Fuck yeah," I growled leaning up and letting my hard prick jut out in front of him.

He didn't take it immediately but instead undid his towel and let his nice but regular sized dick stand up exposed. He plopped the cap of one bottle and lubed up before unscrewing the top to another brown bottle and raising it to each nostril.

"Aw fuck!" he exclaimed then dove onto my dick. He didn't have Cahill's skill, quite, but he had double the enthusiasm. Mitch Ellis fucking loved sucking dick. He grunted and swallowed and fought his gag reflex. But mostly he stuffed my cock into his throat and bobbed vigorously on it while he jerked himself. It felt good. No, it felt great.

But he backed off. "You can take charge if you want." His voice heavy with desire.

I didn't understand what he was getting at.

"You know, fuck my face. I like that." He took a couple more hits from the bottle.

God, if Mitch's buddies could see him now, I thought, as I stepped up and speared my fat stick into his mouth. He grunted, letting me know I was doing the right thing. So I did it more. Harder, deeper, using my hand on the back of head to steady him as I fucked his throat. I loved the contrast of sensation. Mitch's warm wet throat, his gelled hair in my fingers, the heat emanating from his body. It was one hell of a rush and after a minute I started cumming, hard.

Like Mr. Cahill, Mitch swallowed my seed without hesitation.

I was lightheaded when I stepped back and had to marvel at the semen that dotted Mitch's hairy chest and stomach. Clearly he'd fired off big, too, while I'd ridden his mouth.

"I'll get you a towel," he said with a wink, as he collected my clothes. He was gone a minute then came back with an extra towel for the shower.

"I'll say... you earned a big stud fee," he teased. We hung up our towels on adjacent hooks and showered next to one another. At that hour on the weekday the showers were deserted. It felt like we were buddies in a way, despite our age difference and the fact he was a club member and I an employee.

It was only as we showered that I noticed his wedding band. I thought back to what Adam had told me. It was the ones you didn't expect.

"Thanks for making my week, buddy," he said as we rinsed off.

My impulse was to thank him, like I had Cahill. After all Mitch had serviced me. But I didn't want to seem too willing. "You're welcome, Mitch," I said, being sure to flop my sated junk with my towel for his viewing.

"Fuck," he shook his head and laughed a little. "You're trouble," he teased.

I didn't have to wait for my next week's assignment to know I'd be caddying for Mitch regularly now.

***

I came home that day two hundred bucks richer. I knew then that I'd have to start saving my money. I set up an investment account online for some of it, but I figured I should be keeping most of my earnings under the table. I found a good place to stash my cash in my bedroom. There'd be more to come, I had a feeling.

I was right. The next day was my biggest tip of the month. He wasn't an exec but a blond stock broker about my height. Thinning hair, barrel chested build, almost stocky. And he was the direct, no-BS type. As he teed off on the 17th hole, he handed me his iron and said in a low voice, "I'd love to suck your dick after this."

I wasn't sure if he was offering me money to do so, and while I very much liked the idea of this dude going down on me, I wasn't ready to give it away for free. "I don't know," I said, my voice guarded and my face dead panning as I cleaned the club and placed it back in the bag. I picked it up and walked alongside him.

He was talking to his golf partner, but the minute the other man stepped away he leered at me. "I'll make it worth your while."

"How?" I asked. In the course of a week I'd gone from stumbling into my sexual encounters to negotiating my fee.

"One fifty. Plus fifty if you let me lick your hole."

Damn. My account was going to grow fast. I still wasn't sure about the rimming, so I said. "Let's just start with the blowjob."

The man smiled. "If you're as hung as they say, you're going to do well around here."

"Thanks, sir."

"You mind a bit of advice?" His eyes looked at me seriously, sexually.

"Not at all sir." I was nervous he was going to tell me that I was risking my job soliciting members for sex.

Instead he just patted my shoulder and leaned in to speak closer to my ear. "Lose the underwear. Advertise the goods a little. You're the whole package, stud."

I smiled. "Yes, sir."

Mr. Stock Broker was a good but not great golf player. And when we got into one of those private rooms, I found out he was a good but not great cock sucker. He was appreciative, though. Praising me, praising my dick. He liked its shape, liked its size, liked how hard I was. The man took his time to lick up and down and nurse the head a little between bobs.

"You definitely need to show this baby off, Matt," he growled before taking me into his mouth again. His sucking started to feel good, that gonna-get-me-to-cum good. But an idea had stuck with me.

"If you want to lick my ass," I said. "That'd be cool."

"It would huh?" he laughed. He leaned back and nudged my legs up. I pulled them back and used my core strength to keep me upright. I wasn't sure what to expect but the feeling of the man's tongue on my exposed pucker was incredible. Mr. Stock Broker may have been just good as a cocksucker but he was an expert at eating ass. Not that I had anyone to compare him to, but his rim job felt incredible and moreover seemed to drive him wild. I was surprised at how eager he was, and how deep he went with his tongue.

He was really turning me on, like body-shaking turned on, until he finally pulled off and went straight to my dick. Three bobs and I was cumming in his mouth.

Unlike Mr. Cahill and Mitch he wasn't friendly afterward. He was downright standoffish and gruff. But I was two hundred bucks richer, and sure enough he booked me for the following week.

***

I stopped wearing underwear between my khaki shorts. I blushed nervously the first time or two a member did a double take at my hanging junk, but after that I ate up the attention. I got a lot of it, too. I'm sure not all the guys were interested in sucking me, but knowing they were comparing themselves to me and falling short, I felt grown up for the first time in my life.

Fridays were busy and I had a double shift. And I got sucked off twice, first by a local politician, the second time by a real big burly guy, a former NFL player who was about 6'5" and 250 pounds. Politician Dude gave a measly tip but the NFL-er's made up for it. He seemed very excited by my endowment. After I came he asked if he could keep playing with my dick.

"Have at it, sir," I said, leaning back and letting him caress and lick my dick as I softened. If I hadn't already come once that day I'm sure I would have thrown hard again.

"I'd love to do more to take care of this," he said in his deep voice.

Other than my time with Mitch I didn't shower in the main locker room but instead waited outside for the men to clean up and get dressed. It was weird seeing Mr. NFL all preppy like one of the executives, but the mismatch in clothing looked good on him. "Think you can keep your Fridays free for me?" he asked as he stuffed what turned out to be a flat two-fifty in my fist.

"I'll check with Mike but I'm pretty sure I can," I replied with a respectful, can-do tone in my voice.

"All right, see you next week, hopefully." He gave me a wink and a handshake.

Damn, this club was one surprise after another.

***

"You should take a day off," Dad said one Monday as I came in just in time for dinner. I'd hadn't caddied that day actually but I'd gotten a call from Mr. Cahill. He'd gotten home from his business trip early and wanted to know if I wanted to swing by his place? I did swing by and left the Cahill house two loads lighter. I guess I had that exhausted look on my face when I came home.

"I got to make the money while I can, Dad," I said defensively. "I have only little over a month before I go away to college." Of course I didn't tell my parents where most of my earnings were coming from. By now I'd developed a steady rotation of regulars - one shift Tuesday through Thursday and doubles Friday through Sunday - and unless one had to cancel I never had a new member to caddy for. And of the 9, 7 were blowing me regularly for an extra fee. The sex and the money were addictive.

Still, I sensed Dad's frustration and I started turning down any Monday pickups. And when my Tuesday guy went on vacation for a couple of weeks I told Mike I wanted to keep that as a day off. Those days, I did some chores around the house, mowing the lawn and tidying up the house, and I hung out with my buddies in the evening. Oh, and I jacked off a lot. My libido was really keyed up and even a day without head had me thinking about sex a lot.

By early July Mr. NFL, Andrew Carter was his name, had taken things further. He was going to town sucking me. I stood while he was on his knees. The man had actually gotten better at it over the summer. It's funny, each member sucked dick differently, and I was learning what I liked best.

Not that I could pick a favorite. Maybe Mitch, because of his laid back demeanor and the fact we kissed. I realized I enjoyed the kissing, too. A lot.

I wanted to kiss Mr. Carter that day, so I went ahead and did it, leaning down and meeting his mouth for a kiss. I wasn't sure the big guy would be into it, but he was, moaning into my mouth as my tongue pushed in. He was more passive than Mitch when it came to making out, practically sucking my tongue in but not pushing into my mouth with his. That turned me on big time for some reason.

He stood up, erect and clearly horny. His hairy burly body lorded over mine by a half foot and some considerable bulk. Still he craned his head down and we continued to make out, me taking charge and now exploring his body with my hands.

"Can we try more today, Matt?" he asked me with his booming voice. Despite his gruff appearance, he was surprisingly sheepish as he put forth his request.

"What do you have in mind?"

"You ever fuck a guy?"

"No," I said. "But I'm game."

"There'll be extra in it for you," he reassured me as if the idea was repulsive to me. It wasn't.

"Cool," I said. "Um... how should...?" I wasn't sure how fucking went down between men. It looked too easy in the porn videos.

Mr. Carter nodded and reached over to a small bag, where he pulled out lube and started slathering my cock. The liquid felt cool but the knowledge I was about to bone this big beefy ex-athlete had me rock hard.

"Never taken one this big," Mr. Carter said, as he ran his fist up and down my lubed erection. "Hell I didn't even know they made them this big."

He seemed not to want to let it go but he did and turned around leaning over the massage table. Hiking his ass up and spreading his strong legs he gave a half look back over his shoulder. "Lube me up Matt. With your fingers first. Then go slow, OK?"

"Yes, sir," I said. Me and Mr. Carter weren't on a first name basis yet.

His body shivered as I teased his cleft with my fingers. And practically let out a deep coo as I sunk one finger in. Mr. Carter had been fucked before, no doubt. It wasn't till I got three fingers in him, pushing and twisting that I encountered any resistance.

Finally, I lubed my cock up some more and slowly fed it inside this beefy man's hole. Instant heaven. Snug, warm insides undulating around my dickhead. And the view of his strong backside only added to my excitement.

"Go slow, man," he urged. "You got a horse dick on you."

"You like that horse dick," I replied, feeling my oats.

He leaned up, wincing a little. "Yeah, I do. Oof. Oh fuck, you're big."

It took me a while to work my way into his tight hole, but once we got to fucking we both loved it. I sank deeper, and was surprised to see it go in stages. A few inches would push in easily, like a knife through soft butter, then I'd hit a knot of tightness that would make me have to wait to let him relax. I'd coax against the tightness with small mini-thrusts, till it gave way and I'd sink a few more easy inches inside the ex-footballer. Finally my balls kissed his ass cheeks and I heard a soft "Oh God," from the man as he realized I was completely buried.

I leaned down and kissed between his shoulder blades then slowly pulled back for my first thrust. At that moment I knew that I not only liked fucking, I LOVED it. Even more than the blow jobs. It was a physical cascade of pleasure but also a head rush. "Oh fuck, sir, your ass is so fucking hot." I pushed in again.

"God, fuck me, stud. Getting fucked by a goddamn horse," he grunted, gripping the edge of the table tightly. I could tell it was intense for him, but I also figured he could tell me to stop when it was getting to be too much.

He never told me to stop, so I kept at it. Fucking him steadily then gaining speed and power.

"Use me, Matt. Fucking wreck my hole, man. Shit!"

I'd gone quiet now, putting my energy into the fucking. Trying to keep myself from coming too soon. Thankfully I saw his right hand leave the table and reach down to his own cock, flogging in synch with my thrusts.

I was able to focus on both our pleasure now, fucking us to climax together. I leaned later in life that not all tops found that easy, but at that moment it seemed the most natural thing, the short circuit between me and Mr. Carter. The more excited he got, the more excited I got. Till he finally grunted as he came into his fist. I gripped his hips and pounded my own sperm into him.

"Oh fuck," I hissed as I fell onto his bare back, my ejaculating dick buried deep inside him. This was hands down the most intense orgasm I'd ever experienced.

Mr. Carter had a quiet, serious look on his face as we finally uncoupled and stood up. His dick hung soft from his hairy crotch.

"I didn't think I could do that. But, fuck, that was the best sex of my life. Can I kiss you again?"

I nodded and stepped up to him for another kiss, softer this time. I don't know if Mr. C was the romantic type but after our fuck it felt like the proper way to communicate our intimate connection.

Finally, he let out a nervous laugh and patted my hip. "Damn, you earned the extra money all right."

"I feel bad taking it," I admitted. "That was pretty awesome for me, too."

That made the big man smile. "You said that was your first time? Seems like you have a lot of experience topping."

"Topping?" I had a good idea what he was talking about but hadn't heard the word.

"Fucking," he clarified.

"No, actually," I said with a smile. "It was my first time. For real."

Mr. Carter's teeth formed a bright smile. "No shit? I got your assfucking cherry, huh?"

"Yep."

He reached back and felt along his ass. "You came buckets, too. Fuck!"

"Sorry," I said. "I was kind of horny."

"Don't ever apologize for a load like that," the ex-athlete grinned. "Us bottoms love a guy who shoots heavy. It's hot as fuck."

We kissed again.

"I hope this isn't the last time you fuck me," he said softly as his hand reached down to cup my mostly soft dick.

"No, sir."

Now, blowjobs were off the menu with us and each week Mr. NFL bent over or lifted his legs for me. Already generous, his tips grew bigger.

And by end of July I had over $10,000 in my personal piggy bank.