Top Lessons

probably wasn't one of those "top from the bottom" kind of men, but I was 18 when we started up and I didn't have much experience. Well, any experience, really, when it came to fucking. I'd watched a ton of porn and fantasies about bottom daddies. But that was it.

The fantasy men weren't even as hot as Don Grayson, at least not to me. He was late 50s, pushing 60, and on the mature side of the daddy spectrum. Balding, mustached, mostly gray in the remaining salt and pepper hair, and silver all in the thick chest, leg and arm fur. I was surprised how much I was into a look about two decades older than the "daddies" I had jerked off to in my teen years.

The age of a lot of the guys on Daddyhunt was in that older range, too, and maybe that helped. Don stood out from the rest, in large part from the respectful, friendly way he responded when I first messaged him. I'd been used to guys on the lecherous side and to men trying to convince me to give up my anal cherry to them. I was still feeling out my own wants, desperately craving sex and ready to take the plunge but also protective of my limits.

On one hand, Don was the most amazing first fuck I could have imagined. I'd gotten head from a couple of older men before, but I realized I barely counted them after my first time with Don. He came to the city once a month for business, and after meeting up for a coffee to see we were both on the up and up, I went back to his hotel room. We stripped and made out some on the bed before he guided me into lubing him up and entering him. 

At the same time, I was nervous and too in my head to really enjoy it. And I came prematurely, which embarrassed me. 

I apologized to him profusely, feeling like I'd let him down but also myself. I wanted to be the stud top in my fantasy, but I'd not been able to last ten seconds inside him. 

"It's OK, buddy," he said pulling my lithe naked body to his burly beef. "I'm pleased you get turned on my an old dude like me," he said, giving a reassuring grin beneath his mustache.

I ran my hand along his beefy furry chest. "God, you're incredible," I enthused. "I'm gonna think of you for a long time."

He ran his hand up my taut belly. "That mean you're not interested in meeting up again?"

I sat up a little, surprised. "Oh, yeah, I'd love to... just figured after just now..." I still felt embarrassed, too embarrassed to finish my sentence. 

He gave me a leer of a smile. "Maybe I can coach you a little, stud... if you're up for that."

"I think my ego can stand it," I winked.

***

The man was married. He said he and his wife had an understanding about Don's side activities with younger men. I didn't know if he was telling the truth. but I had no reason not to believe him. So he hit me up the next time he was in town.

The second time was easier, more relaxed. I think the fact that Don approached it as a lesson for my topping took away some of the performance anxiety. I was a novice top in his hands, learning what a bottom daddy like him wanted and how he wanted it. He had me do this trick of fucking him with slow, deep strokes while I kept my fingers at the base of my cock, pinching it tight when I was getting too worked up. I managed to stave off orgasm for a good twenty minutes. I watched the middle aged businessman work himself into a deep cum, shooting heavy ropes of daddy cum all over his fur. Mission accomplished, I let go of my dick grip and instantly I was cumming too. Intense pleasure as I pumped a heavy load inside his hot guts. 

The smile on his face as we came down was a real rush of a reward. That approval warmed me deep inside. Yeah, I had some daddy issues, for sure.

The next time we experimented with different positions. Don coaching me into each of them, but I think he was also figuring out which one worked best for him and my cock size and shape. I did the pinching trick again but found I didn't need to as much. 

We timed our orgasms that day, and I learned how hot a simultaneous cum could be with your partner. 

The third time was an extended visit. Don gave me an extra key card for his hotel room, and I'd come over after his meetings. That felt fun as hell. I knew we weren't a romantic couple, but the man indulged that deeper, more sensual time. We made out for a long time, then fucked, Don telling me to go for a quicker missionary pounding. Then we enjoyed some naked time on his hotel bed, talking.

We talked about what drew us to intergenerational sex. I confessed my daddy issues and some of my incest fantasies. 

"That's pretty common," he said, like he'd heard what I was saying a hundred times. Maybe he had. 

"What about you?" I asked. "What makes you go for young guys?"

He was caressing my stomach but he now moved his hand down to grip my soft cock. "This is my fountain of youth, buddy," he said with a strange sincerity.

I was getting less soft by the minute.

"Yeah?" I laughed, though getting turned on by his admission. 

He nodded. "Something about being pursued by a young guy... being nailed by a young guy... makes me feel younger too. It's hard to explain."

"You're explaining it pretty well," I said. "I dunno... it's hot as fuck."

His look got serious. "You know I'm married, so I'm not gonna lead you on for more than what this is, bud.... But I'm really glad you reached out to me on the app."

My cock was hardening up to full staff in his hand. "You're my dream dad," I said, horniness catching in my throat. "You probably hear from a lot of hot guys."

"You're not the only one," he admitted. "But the only one right now. I prefer to be with a guy I trust... who's not fucking other guys." We'd had conversations about barebacking. I made a deal that if I became sexually active with anyone else I'd let him know and if I fucked with other guys, I'd go on PREP. 

"I'm not," I reassured him. 

"You're probably horny enough to," he said, looking down to see the way my dick throbbed in his slowly stroking hand. I wasn't sure what he was fishing for. But I think he was just checking in and maybe teaching me to be honest about things.

I thought a second. "Yeah, definitely. But fuck, the sex wouldn't be as good as with you. Maybe that takes away the motivation to look for a local daddy."

He liked that answer. A lot. "Well, I probably shouldn't be working so much to boost your sexual confidence." To this day, I loved how open and direct Don Grayson was. He could say things that from other guys might seem challenging or hurtful. But he was my supportive dad, and I ate up any lesson from him. "Once you realize what a stud you are in the sack, you're gonna be trouble."

I felt a rush of excitement at that idea. I climbed onto his beefy body and met him for a kiss. Taking the top position on him. "I will, huh?" I growled into his mouth. Humping my now rigid cock into his genitals which were firming up against mine. 

"Absolutely," he growled back into my lips.

"How bout I give you more of that fountain of youth?" I hissed, kicking his legs apart and communicating my desire to fuck again.

"Fuck yes," came his response.

***

The fourth visit was just a quickie hookup for us, but the fifth gave him a couple of nights in the city. We were getting used to the extra time together. Don Grayson had me rim him when we met up. Not a quick lick as before, but a true asseating. He was face down on his bed as I licked and explored his trench and hole. Sometime he told me what to do, sometimes he let me follow my impulses.

"Put your thumbs in my ring," he finally said, raising his upper body off the mattress a couple of inches as he spread his legs further. "My hole is completely clean, buddy, so  you can root around up there..... aw fuck, that's it, push it in, man."

I'd enjoyed rimming up until then, but the minute my tongue pushed further into his ring, my cock surged and I went wild. This was the primal sex I didn't realize I was missing. 

"Oh fuck... you like that buddy, huh? I can feel it... that's a good boy... eat your daddy's hole.... As YEAH!"

I had to use the pinch-my-prick trick when I finally mounted him. Even if it was awkward in that face down position, I just knew I was too worked up. But I got into the groove of that fuck and pretty quickly had both my hands by Don's meaty arms, using my full body for a nice rocking leverage in and out of his hot daddy hole while I kissed his neck. 

"Am a I good boy, now, Daddy?" I hissed.

That got a choked grunt from the man. "Oh yeah, son... making your daddy feel so good...."

That was gonna get me off. Maybe it was OK I was coming first. It'd have to be, because I didn't feel like pinching my cock or slowing my fuck. I threw all my power into thrusting into him with fast, steady strokes. And, like that, I had an incredible orgasm that lasted a good half minute.

***

The next visit was actually his 60th birthday, and we went out for dinner together for the first time. A date in a way. I took it for what it was, but it was also my first date with a man, and I was going to enjoy it.

"Thanks for making an old man feel a little younger," he winked as he clinked his wine glass to my glass of soda.

"Well, thanks for helping me feel a little older," I shot back. Then lowering my voice, I added. "Besides... I'll let you in on a secret... I love fucking old men."

He laughed. "Happy birthday to me, then."

We were in a good mood when we went back to his hotel. Part of me wished I could host for once, but I had just a dorm room, which meant a small bed and a roommate who was always around. My roommate knew I was gay, but I had never admitted my preference for older men to him. It didn't seem worth the conversation.

We were sensual once we got naked but also didn't take it too slow. Don and I were both worked up. We made out a little, then I got down to rim him. Don pulled his legs back and let me feast on his daddy hole. Not a long rim session but deep and intense, before I pulled back and reached for the lube.

I loved being trained by Don. I loved the way he had worked up my ego and confidence. I loved how he articulated what he liked most in a top and I loved trying to live up to it.

But the hottest sex so far was gonna be now: the time I just fucked. No lesson, other than maybe the silent approval I'd mastered the kind of foreplay that got Don Grayson to put out in a major way. To have him place those strong legs on my shoulder and look me direct in the eye as I penetrated him. 

This wasn't me being green or impetuous. But it wasn't also fucking strictly how Don wanted. This was a melding of me and him, of my top desire and his bottom urges. Feeding off one another. Working up steadily from slow to fast, gentle to hard. I'd not actually fucked the man that hard, though the face down fuck had come close. Now that I could see his face I knew he wanted this. That urged me on, and my hips worked harder. He stroked his dick wildly. Getting closer.

"Come on, Daddy," I growled. "Come for you boy." I fucked harder. "My hot 60 year old daddy," I added. "Hot 60 year old dad for my 19 year old cock."

OK that part was for me and my excited headspace, but it turned Don on, too. His cum flew out everywhere, just two seconds before I began my own cum. I kept fucking him, though with nice gentle massaging of his insides to let us both ride out our orgasms. 

His eyes were wide when I pulled out my dick at last, still firm and very wet with sperm.

Greedily, he reached down to grip the cock that had just been inside him. 

"Damn... I'm gonna have to worry about you going around chasing other daddies now, aren't I?" 

It was another one of Don's astute, directly honest comments. It was amazing how he could read me better than I could read myself.

My dick twitched in his hand. Not wanting another fuck just then or anything but very much enjoying the postcoital stimulation of his touch. I knew then that Don was right. I'd want to tap other men's asses, other older men. "Yeah, probably, and probably soon," I responded truthfully. "But I'll let you know when I do."

I got off the bed and helped him up so he could go shower off. I downed one of the bottled waters on the table, eager to rehydrate after that sexual performance. I took a rinse  after he got out. 

When I got back he was on the bed, waiting for me. Fully naked, looking amazing for 60. "You got a second, or do you need to get back?"

"No rush," I said. "I'm pretty much caught up on schoolwork for tomorrow," I replied as I got back on the bed. The sheets were damp from our coupling and our sweat, but I didn't mind.

He gave me a soft look that contrasted to his hard masculine features. "In that case, you feel like staying over?" I could tell he was nervous asking me.

"Yeah, I'd like that," I replied. We kissed. And kissed some more. Something about kissing a man 41 years older than you is a turn on, even if you've already just had a hard cum. My dick was firming up again. But neither Don nor I made a move to do anything about that.

We pulled back and focused instead on caressing each other's bodies. Me indulging my daddy fantasies, Don appreciating the fountain of youth I represented to him. 

"How do you know what's on my mind?" I finally asked.

"Whaddya mean?" he asked, showing he did not in fact have ESP.

"I mean about me wanting to fuck other dads now."

He shrugged. "You're not the first shy top I've been with.... eventually you guys become less shy."

"Is that your thing?" I asked. Not judgmental, and Don knew I wasn't being judgmental.

"Maybe more than I'll admit," he said. 

I felt he had some insecurity on his mind. Like that milestone birthday was weighing on him more than he expected. Don was normally confident and easy going. But tonight he was moody as hell. I gripped his shoulder and enjoy the feel of his more mature muscle. "You know when I start fucking other dads, I'm still gonna want to be with you... anytime you're in town." I scooted in. "You're not jealous are you?"

He nodded. "A little," he admitted. "But I also want that for you, you know? For real, I do. I dunno... I guess I'm sound like a mess of contradictions."

I leaned up, running my hand over his chest now. "How bout this... no more talk about other guys until I actually do it, OK? I'm just honored you decided to spend your birthday with me."

That made him smile. His dick was filling out some, I could feel it against my hip. "It was hot when you started talking about our ages, while you were in me."

I grinned. "I didn't know that worked for you like it does for me."

"I was surprised, actually," Don said. "You're teaching me some new stuff, son," he hissed. 

That got me full on boned. I wasn't sure what Don was thinking but the vibe was becoming very sexual. "You ready for sex again?" I asked, a probing question that suggested I'd be surprised if he was.

"I can't get off again, not anytime soon," he admitted. "But I want you in me again. Now."

"Yeah," I grunted. My dick loving the idea. 

"Just go slow," he cautioned. And like that he was getting up onto all fours. We had tried out doggy position briefly but never had a full mating that way. 

But I wanted this. Wanted that deep connection with this perfect man and a chance to enjoy a less rush fuck for the second round. I knelt behind him and lined up my prick to tease his recently fucked ring. It gave way with some work, and I was soon tapping my own cum just inside him. 

"You're a hot fucking 60 year old," I growled as I bottomed out inside him. Enjoying the view of his strong back, smooth and tan and a contrast to his paler, meaty buns. "You're gonna be hot when you're 65. Or 70. Fuck."

I don't know Don pushed my buttons so much. But if I knew, it would probably take away the magic of the sexual chemistry. I was responding to this older man with my heart and my cock and not my head. It was better that way.

After five minutes, Don had me stop and pull out. He wanted a break. But went down on me for a bit then we made out before I entered him again. Missionary. For a while. Then another break. I was getting into this pace, this alternation, the claiming and reclaiming of his hole as we worked our way around the bed, alternating between silent fucking and hot verbal. 

It was my first marathon fuck. Topping Don Grayson until the wee hours of the morning. Edging myself and geting him back into the place where he was finally ready to cum again. Celebrating the big 6-0 in style, his body went into overdrive as he came. My orgasm when I finally nutted in the man was the absolute deepest and most pleasurable of my life.

Leave it up to Don to give me one last lesson.