The next day I was a little bit of a wreck. Still coming down from the high of my fantasy time with Mike Keenan. Sucking his cock. Kissing him. Enjoying the privacy and the deep conversation. I thought of texting him but decided that wouldn't be welcome. It hadn't been a date, it had ust been something that had happened. A combination of Mike taking pity on me and wanting to get his rocks off. We both got something out of it, but it was surely a one-time thing.
I had class that next morning and baseball practice that afternoon, then weightlifting. It was early evening when I got done and saw I had a text from Mike.
"Hi Luke, sorry no contact, I had a long day here. Enjoyed last night. Any chance for a repeat some time?"
My heart pounded. Maybe I was the one overthinking things. Mr. Keenan just wanted his cock sucked again.
"I'd love that," I wrote.
"Nice," came the reply. "You around to talk?"
I said good night to my buddies and told them I had to get back to study for a test. Then I texted a "yes" to Mike. A second later my phone rang.
"Hey," I said. God, I was majorly crushed out on the guy.
"Hey Luke," he said. His voice was sexy as fuck. "What are you up to?"
"Just getting out of practice. Bout to grab some dinner."
"I haven't eaten either. Want to come over? We can get dinner in the hotel bar."
"I probably need to change," I said. I was still in my workout clothes.
"I bet you look sexy as fuck," he growled. It was a trip to hear him lust for another man. "But take your time."
"Yeah, I probably shouldn't go to some fancy bar in my gym clothes."
"They don't give a fuck," he said. "But do what you feel comfortable with."
"All right," I said. "I'll text you when I'm on my way."
"Take an Uber," he said. "I'll pay."
"OK." Then I hung up. I was going to object, but I was eager to see the man. And truth be told I was hungry, real hungry. Maybe that's what made me decided to head right over, underdressed as I was.
"OK, I'm getting in my Uber," I typed to him five minutes later.
He sent a smiley face reply.
The man was in his suit, without tie, on one of the bar stools and his eyes lit up as I walked in. He had a smirk as I set down my backpack and pulled out the adjacent stool to sit. "I was right," he said softly. "Sexy as fuck."
I blushed. "I didn't think you went for guys that way," I whispered.
His blue eyes twinkled some as he patted my back. "No labels, remember?"
I was getting hard in my shorts. Unfortunately the thin fabric wasn't going to hide my boner, but fortunately, it was hidden by the bar. And my hunger was going to win out.
"The steak here is great," the man said as he handed me a menu.
"I dunno," I said as I looked over the option. "A burger is fine." Of course I was concerned about the price.
Mr. K could read me, though. "Get the steak," he grunted.
I felt a little chastised and said something I instantly regretted. "Is that how the Sugar Daddy treatment works?"
Mike gave me a quick glance then replied without missing a beat. "Buddy, you don't eye me up like a cash machine like those girls do. You don't know how nice a change that is."
I blushed and I felt his hand pat my bare thigh.
"I like that I can be honest with you, Luke, for real." His bossy tone was gone, replaced with the old Mr. Keenan charm.
I gulped. "I like being honest with you, too," I said. Until Mr. Keenan re-entered my life six months prior, I hadn't realized how rare it was I could be honest about things. I gave him a smile and saw him smile in return.
"Since I'm being honest," I started, but just then the bartender came over to take our order.
"Two steaks," Mr. Keenan said, ordering for me. "And another scotch and..." he turned to me.
"An IPA?" I asked. The bartender nodded and named off some brewery. Sounded good. We watched as he poured our drinks in front of us and placed them on the bar before going off to ring up our order.
"So..." Mike picked up. "Since you're being honest..."
I lowered my voice. "It's like I said before. You don't need to pay for anything, Mike. Or be a sugar daddy or anything."
He grinned. "There's always trade offs," he said. "And maybe I enjoy the control."
"Control?" I asked dumbly.
"If you're paying, you get your say in a lot of things," he said. He paused and watched me blush. "You think less of me."
"Honesty, right? You don't know how crushed out I am on you."
He smiled. "I have an idea. It's flattering." He took a sip of his scotch and looked over at me like a wolf eyeing up his prey. "I'm hoping you stay over tonight."
I was in over my head. Emotionally, but also with a man like Keenan. Decisive. "If you want, I will," I said.
"Good," he said, satisfied.
***
Mike Keenan surprised me that evening. After we ate and he paid the check, we went up to our room. We showered together, making out, feeling each other up. I was surprised how much this straight man was into my very male body and my cock. Well, he was probably bi and in any case had his no-labels motto. I was gonna embrace it.
Particularly as we made out on the bed, me beneath his middle aged, fit hairy body. I'd eventually find a real boyfriend, I knew, but I also knew it was going to be hard for any man to live up to hot how Mr. K was. His cock felt hard and even bigger as we humped our bodies together and kissed.
"So, Luke... you up for me being inside you?"
I nodded, hungrily. "God yeah, Mr. Keenan."
He grinned. "You have much experience?" That concern coming in.
"A couple of guys, yeah," I said. Then with deep candor, I added, "I wish you'd taken my cherry, Mike."
His voice got husky. "I've done anal a couple of times. With an ex-girlfriend."
His words made me actually break out into goosebumps. For some reason the idea of Mr. K doing some woman in the backdoor seemed kinky as fuck. But also the way he unmistakeably was communicating that he knew how to fuck me. "You liked it, I bet," I said with a lusty smile.
He nodded and winked just as he leaned up and knelt on the bed. His hardon looked magnificent, the thickness perfectly framed by his hairy, DILF-y body. I decided then and there I'd have a hard time sleeping with a man under 40. "Oh, yeah, buddy," he said. Then my body shivered again as I watched the confidence with which he picked up the lube he'd set out next to the bed. As he returned his focus, I pulled back my legs and spread them some, letting his slick hand in to lube up my hole. "It's probably my favorite thing. Hard to talk a woman into it, though."
"I can imagine," I hissed, enjoying the cool contact of the lubed finger on my ring. "I bet that costs extra huh?" Maybe that sounded accusatory, but from my tone it was clear that it was a joke, and Mr. Keenan picked up on that.
He laughed. "I don't hire hookers, but don't think I haven't thought about it." His cock jerked, and I was relieved that being with a dude seemed to work for him as much as fucking a chick.
He pressed in and worked me open some. "That feel OK, buddy?"
I looked at him excitedly and nodded. I kept expecting resistance as the man fingered me but there was none. At all. "Feels amazing Mr. K." My longtime nickname for him just slipped off my tongue, but the man seemed excited to hear it. His cock actually jerked.
He now slipped in a third finger, twisting me open and working in and out. "You're ready," he said, though I knew there was a questioning behind his assured tone.
"Yes, sir," I hissed.
Mike was horny, too, I realized as he scooted in to place and nudged his meaty cock right into place. I don't know the approach he took with women, but he angled his finger to let his prick push in just as he withdrew his hand. Kind of a shoehorn move that slid his meaty cock right into me. Three solid inches inside me in one go.
"There ya go," he said with satisfaction. Then he moved forward, his hips driving more meat into me, as he leaned his upper body forward. I was getting well and truly penetrated.
The thing was, my insides were starting their natural resistance, my guts clenching down on the invader and trying to repel it. Mr. Keenan mistook my discomfort for a natural stimulation of an ass on his cock. "That's goddamn nice, buddy," he hissed and like that he was kissing me, hard and possessively.
I met his tongue as well as I could, but there was something that clicked in me. I was a dude, a masculine dude. I didn't like to think of myself as feminine, and I got offended by the way people would associate gay sex with being feminized. And yet, I was pinned down beneath Mike Keenan and all I could think was to compare myself to those college chicks Mike banged. My hole relaxed around him and I wrapped my legs around his waist. Not slutty or anything, but damn I needed and wanted a Mike Keenan fuck.
He must have sensed the change but in any case pulled back from the kiss. "I guess I didn't even ask about protection," he hissed, his hips slowly pumping me.
"This is perfect, Mr. K," I growled. His dick was rubbing right over my prostate, not punching the button, but playing it like a violin string. It was a surprisingly new sensation for me.
The man liked my answer. He pulled back, further back, and pushed all the way. Then again. Not rushing it, but definitely claiming me with this cock. All the while his blue eyes bore down on mine. "How do you normally like it, Luke?" he asked.
I racked my brain. It was actually hard to think with the man's cock pressing in and out. And I'd only had a few experiences bottoming. "Slow, I guess," I replied. But then as I felt up the man's naked torso and strong arms, I wanted more. "But this is weird to ask... but I'd like you to show me how I like it."
THAT turned Mike on like crazy. "Yeah?" His nostrils flared. "I can do that buddy."
He pulled back and I felt his prick punch into me. In retrospect it probably wasn't rough, but I'd never been fucked with that much force. Then another. Slow, steady, and hard.
The fact that it was Rich's dad doing this drove me wild. I looked up into his handsome face and imagined him rough fucking some sugar baby who'd have to work for her apartment money.
"Shit!" I gasped. My prick was dripping already, a telltale sign that I was about to cum. I gripped it, just in time to let the pleasure boil to a full orgasm, all while Mr. Keenan pounded it out of me.
His own face was scrunching into a clear sign of pleasure. The man was ejaculating into my guts, and good.
"Well, fuck me," he sighed as he lay his forehead against mine. We lay like that, my hands on him and my legs wrapped around him. His more mature, fit body resting on top of me as he caught his breath. "Please tell me you liked that buddy," he hissed.
I felt weirdly emotional. I don't know, it wasn't just the crush I had on Mr. K. It was the hormonal rush on top of the mind fuck of having had such hot sex. "A little too much," I admitted.
That made him smile.
He finally leaned up and slid out of me, and off me. His dick was thick and plump but softening, and very wet. He looked down on me with a mix of surprise, paternal-like affection, and pride in conquest. I loved it all, and it was then that I realized I was hooked on the Mike Keenan experience.
"I thought I was pushing my luck asking you to meet me again," he said as he stepped off the bed and down some water from a water bottle. His middle-aged muscle was covered in a sheen of sweat. The man was sexy as fuck. His eyes barely left my nakedness. "But I guess not," he continued.
I felt all sorts of weird, and more than a little cheap now that the endorphins were wearing off. I sat up in bed, my hole feeling used and wet now. "You really do like being on control, don't you, Mike?"
My words caught him by surprise. "I guess I come on strong, huh?"
"A little," I admitted. "I should probably go," I said as I searched for my briefs.
"Will it make you feel better to stay over?" he asked.
It was my turn to be surprised. "You think I'm like a chick?" I asked. I wasn't sure I was upset he was stereotyping me as a gay guy. Or upset because maybe he was right.
"It's just a question, Luke," he replied. "I'll give you Uber money."
I swallowed my pride. "I'd love to stay. Sorry I was giving you grief."
He smiled. "It's fine buddy. I'm used to game playing. But you're a straight shooter. I like that." Then matter of factly, he added, "I get up early."
"That's cool," I said.
****
I gave Mr. K a blowjob early the next morning. And he stroked me off. I guess I was leaning toward being a bottom before Mike Keenan, but I'd never embraced the label. What the fuck, the man was making me realize the shoe fit.
I was happy and content all day. I kind of wanted a text from Mr. K, but I didn't need one. Even being young and naive, I knew I had to take this for what it was, or not at all.
Around 5:30 I got a text. "Dinner?"
I had a late game and plans with my buddies. "I'm tied up, Mike," I wrote. "Sorry."
"What time you done?" came that reply.
"I don't know. 10?"
"Come over then. You know the room number."
Maybe it should have rubbed me the wrong way, but it didn't. I was horny for this man. So bad.
Only after I replied with an OK, I got a Venmo alert. Mr. K had sent me money. Not an exhorbitant amount. But a lot.
Oh shit.
***
I was nervous as Mike ushered me in. The worst part was how fucking handsome he looked, even in his readers and plush hotel bathrobe. He didn't look exactly sleepy, but he seemed in a relaxed, tired state as he looked me up and down.
"Thanks for coming, Luke," he said. That easygoing charm I remember from going over to his place when I was visiting my buddy Rich.
"Sure," I said. Looking around, I wondered what it was like to live in a hotel like this a few nights a week, always being on the road. I smelled Mr. Keenan's cologne before I felt his hand on my shoulder and his warm body press against my back. Already he was kissing softly at my neck.
"Listen, Mr. K... can we talk about the money thing?"
His voice had a throaty growl. Maybe he'd been thinking all evening, all day about sex, because he seemed to be in a horny mode. "Sure. Was it not enough?"
"No, Jesus," I hissed, feeling his fingers already running beneath the hem of my T-shirt tracking my abs. "I don't need anything. For real."
OK, now his fingers stopped their seductive movement. I guess the man was getting it. "You offended?" he asked.
I blushed. "I dunno," I replied. "It didn't make me feel great."
I felt his breath against my neck. "You deserve the money more than Kimberly," he said. "Or the others. It's just a little something, Luke. Use it to have fun. Or save it for a rainy day."
I don't know how Mike Keenan was so persuasive a man, but he was. Maybe because those fingers are once again tracing up my abs and pulling my shirt with them. "Come on, buddy, let me see that hot baseball jock body," he urged.
I went with it. I knew I was good looking, and even if I had some bulking goals for the off season, I knew I had a solid body. But the fact Mr. Keenan was into it had me so turned on. I turned around to see a smile on his five-o-clock-shadowed face.
"Nice," he said, eyes sweeping up and down my build. "Lose the shorts, Luke," he said.
Mr. K had talked about enjoying being in control. I was now wrestling with the fact that I enjoyed being bossed around, at least by this man. I stepped back and undid my shorts, stripping down completely for him. I was rock hard.
My heart pounded as I watched Mike get a more serious look on his face, as his hands reached down to undo the tie on the robe. The white terry cloth flapped open to show off his furry fit torso and, beneath that, his thick boner. "Come on buddy," he said in a deep whisper, nodding down at his crotch in an unmistakable signal.
I gulped. I assumed my normal catcher's squat, a position which made my hard dick stick up at an angle.
"Fuck yeah," Mike said. He scooted up to offer me his prick. It was fat and veiny, and while not porn-long that dick was pretty damn big.
I leaned forward just an inch to start licking him. Top to bottom. Along his furry nuts. Tasting every inch of Mike Keenan. Maybe his relaxed vibe gave me the implicit permission to take my time.
Only by the time I actually began sucking him, working my mouth up and down on him and doing my best to coordinate suction and tongue along his shaft, the man was starting to get worked up.
"Easy there, buddy," he hissed, gently pushing me off his dick, which throbbed and jerked a little, wet with my saliva. "I almost blew there."
I grinned. I felt so fucking proud. I didn't have a ton of sexual experience and it was good to know I was doing something right to get Mike so close so soon. "Why don't you?" I asked, sitting back on my haunches and looking up at him. I was getting more confident in having sex with this older man.
He let out a heavy sigh, like he was fighting off the urge to do just that. A smile crossed his lips, though. "Guess I'm like a kid with a new toy," he explained.
It took me a second to get it. "You wanna fuck me again." Half statement, half question.
Mike nodded. "Been thinking about it all fucking day, man. Your ass is so fucking tight."
I knew this was a possibility, and I wondered if I should be giving my hole some rest. But I also knew it was going to be hard to turn down a Mr. Keenan fuck. I stood up, my dick riding that crest between pure excited hardness and nervous flagging.
"Ok if we kiss a little, Mike?" I asked feeling almost embarrassed to ask. "You know, make out a little?"
My buddy's dad nodded and grinned as he stepped up to me, placing his hands on my waist. "I guess I can come on strong, huh?" he asked.
God, feeling his dick press against mine and the heat and the soft-hard combo of fur and muscle against me was going to drive me wild. "Some, yeah," I admitted with a laugh. Then blushing, I added, "Part of me really likes it, but fuck it's intimidating too, you know?"
Mike didn't reply but just gave a sympathetic nod and leaned in for a soft kiss. We made out some, and it was incredible to feel the contrast between the gentle approach kissing and the mauling of his hands on my jock body, particularly my butt. Mr. K wasn't kidding about having a new toy. He seemed to really love my ass.
He walked me back to the bed and I went back down on the mattress with a motion of his that was between guiding and pushing. He quickly lost his bathrobe and joined me, covering my body with his older, more experienced one, feeling me up and kissing along my neck, my ear, my upper chest. Mike was in full-on horny mode and bring me there right with him.
Finally he lifted off and rolled to the side. His erection was dripping and rock hard and looked amazing against all that body hair. "All right buddy, get on all fours."
I was primed for Mike Keenan in full on control mode. I scrambled to do as the man asked, facing the headboard and feeling the man settle in behind me. Already his hands were cupping my glutes and feeling the smooth muscle.
"You got a hot fucking ass, Luke," he growled. He pawed at me another few seconds then reached for some lube. The first wet finger felt great, and went in pretty easy.
"You're looser today, buddy," Mike hissed. A second finger popped in.
"Yeah, probably," I responded. "After yesterday."
"I wanna keep you this way," came his deep voice. "Ready for me."
"Oh fuck, Mr. K," I whined. There was an edge to his tone that drove me wild. And as his prick pushed in, I felt a welcome pleasure, even with my residual tightness.
"Fuck yeah," Mike grunted as he felt my insides and pushed to bottom out. "Right back in the saddle."
His grip clenched roughly on my waist. Just as quickly as that thick cock pulled out, it barreled back in. And again. One hard thrust right after the other as Mr. K grunted deeply. "Ung. Ungh. Ung."
The man was fucking for his pleasure, not mine. Still I felt an excited thrill. I wouldn't say I enjoyed this nearly as much as the missionary mating the night before but it felt new to me. Animalistic and raw. I was hard even with the discomfort of the shafting.
Wham. Wham. Wham. That thick piece of hard dad meat was drilling steadily. Then the cadence went off. Mr. Keenan's rhythm was getting more spasmodic and jerky as he pounded me. Then I felt those fingers dig into my hips.
"FUCK!"
From his cry and the sudden stop of his thrusts, I knew the man was seeding me.
I loved every part of the experience, but I now regretted that I hadn't gotten off. The fuck had been too hard and too quick.
Thankfully I felt the man shift behind me and, prick still buried inside me, he leaned forward to press against, my back.
I loved the feeling of his kiss on my neck, but even more I loved the slickness of his palm as he wrapped his hand around my hardon. Mike didn't even need to do much. Just give slow soft pumps in and out of my guts while his fingers ran along my dick. I fired off, heavy and hard. I felt lightheaded when I came.
We were quiet as we uncoupled. The shame was coming back to me as I showered off. Shame that I enjoyed what others might see as a dominant, selfish fuck. Shame that there were funds in my Venmo account. Shame that I was falling for Mr. Keenan so hard. I knew I couldn't stay over in this hotel room, not tonight. I needed some space to think.
Mike had his robe back on. To this day a white terry bathrobe is a fetish for me. His tone was more serious. "You mad at me Luke?" he asked as he sat in the hotel chair and watched me get dressed.
I grimaced but shook my head no. "I didn't think I'd like sex that rough," I said softly.
I could see a sly grin from on his lips. But he continued. "I wasn't talking about the fuck."
God, the man could be intense, behind the suave businessman outgoingness and the friendly paternal vibe. It was like I was seeing the real Mr. Keenan. Intimidating, sure, but I also wondered if he had a hard time with real relationships. His marriage hadn't worked out, he was clearly estranged from his son, and he basically hired dates instead of having real girlfriends.
I paused, just holding the T shirt I was going to put back on. "Can I be blunt, Mr. K? You say you don't want a hooker, and yet have a way of treating me like one."
He was prepared for that. "You're not that, Luke. But I'm not ready for anything serious. I figure I can help you out, and you can help me out." He looked at me and could tell I still didn't get it. "Listen, it's not just sex. I love spending time with you buddy. You're a hell of a lot more fun than those sugar babies, I'll tell ya." He cracked a smile, and I had to as well.
"I guess," I said. Remembering Kimberly, I could imagine she'd be more work than fun.
My conciliatory tone made him happy, and I was glad to see the friendly Mr. Keenan return. "Well, it's just I don't always have the time or interest for all the other boyfriend bullshit. Checking in, looking after emotional needs, dealing with jealousy."
I gulped. I was starting to get a better picture of Mike. The side Rich hated. The side I should hate more.
He watched my reaction but continued. "I know that wouldn't be fun for you to deal with, so I want to make it worth your while."
"Make what worth my while?" I asked. Again, as persuasive as he was, I felt he kept talking around the sex part.
He laughed, almost amused at how astute I was. "Luke, I'm not going to pay you per sex act. Or per night. But..." his voice got conspiratorial. I wondered if he knew what that supportive dad-figure tone did for me, and just weaponized it to get his way. Honestly I think it just came naturally to him. "Well, bud, I'd love an arrangement when you're able to keep me company when I'm in DC." His blue eyes got an impish cast to them, and I knew he was in seal-the-deal mode. "I'm pretty sure we could have a lot of fun together."
"You wanna be my sugar daddy?" I asked, point blank. It's not that I was dumb, but I actually didn't think Mr. Keenan was outright going there.
He nodded. But his face had a caution to it. "Would it better if we ditched the labels?" he asked, a smirk on his face reminding me of his own no-labels policy.
"It would," I answered. Then. "OK if I think on it, Mike?"
"Of course," he said.
He stood up as I finished putting on my shoes. Seeing how handsome he was I almost asked if I could stay over again. But the vibe wasn't right for that.
As I made my way to the room door, Mr. K patted my shoulder. "You're a fine young man, Luke," he said. His fingers gave my muscle a little squeeze before letting go. "I mean that."
"Thanks, Mr. Keenan," I said.
***
The Uber ride was quick at that time of night. I'd have to come up with an excuse to my roommate while I was out again. I'd probably have to come up with a lot more excuses if I hung out more with Mr. K. Or, if he got me my own apartment, things would be easier. Meeting up with him. Having sex with him.
I pulled out my phone. I thought I'd hesitate before sending but I knew I knew my answer.
"You'll have to let me know how it works Mr. K," I texted. "But I'm in."
No labels. But if Mike Keenan was going to call himself my sugar daddy that was probably OK too.
I got a quick reply. "That makes me happy Luke. Talk tomorrow sexy."
I felt warm inside. Mike Keenan was going to make this worth my while. But I was determined to make it worth his, too.
