Sugar Daddy

I was cooling down from my run, and I was paying more attention to the traffic light to cross. I almost didn't see them. 

But the man saw me, a look of embarrassment sweeping his face before the familiar friendly tone won out. 

"Luke?" he said. 

"Mr. Keenan," I replied automatically, as if the recognition was coming out of my mouth before it hit my brain. Mr. Keenan was my buddy Rich's dad, a successful corporate lawyer or something. I know Rich had issues with his father, made even worse by his parent's divorce, but Mr. K was always beyond nice to me. And truth be told, I always found him incredibly attractive. Tall, handsome, salt and pepper coming in on the temples, kind of like a TV dad. Even now he was in a nice-cut navy suit, dress shirt and no tie. 

His blue eyes were taking me in. It had been over three years since I'd last seen the man, since high school graduation, and I'm sure I looked different now. "I almost forgot you went to school here," he said. "Georgetown?" he prompted.

"Yes, sir. They haven't kicked me out yet," I smiled in my self-deprecating way. 

It was then that I noticed the woman standing next to him. She couldn't have been any older than me. She was pretty, real pretty, with that sorority girl look. Straight blond hair and big tits for a girl with her trim frame. At least they showed off well in that spaghetti strap cocktail dress she had on. Her high heels didn't get her close to Mr. K's 6'3" height but they added a couple of inches. 

I now had a pretty good idea why Rich's parents got divorced.

The man's date was good at hiding her annoyance at my presence but not good enough that I couldn't see that she wanted to get on to where they were going. Part of me couldn't blame her. It was fall, the evening was cool, and she was underdressed for it.

Mike Keenan realized where I was looking and that embarrassed look came back on his face. "Luke, this is Kimberly..." he turned to his girlfriend or date or whatever. "Luke's from back home," he explained. Almost with an emphasis of meaning. 

Turning back to me. "We should go, buddy... but it's great running into you, Luke."

"You, too, Mr. Keenan," I said. It was only then that I was self conscious about standing on a busy Georgetown sidewalk in my sweat-drenched running clothes, the cool getting to me now that the exercise was wearing off. 

He flashed his trademark smile, like he always did when I came over. He reached into his pocket and pulled out his wallet, deftly extracting a business card. "I'm in DC a few nights a week these days. Reach out and we'll catch up, OK?"

"Sure thing, Mr. K," I said, taking the card in my fingers. 

Then I watched as my friend's dad and his college-aged girlfriend went walking on to their date spot.

****

"I was gonna ask if you can keep things under wraps about Kimberly," Mr. Keenan said as we waited for our burger at a nice but not overly fancy bistro that DC seemed to have a ton of. I'd met Mr. K closer to his hotel, just two nights after running into him. 

"Oh yeah, sure," I said. If the man had asked me to give an alibi to the police for something I probably would have. I mean, Mike Keenan always was great to me, encouraging me in my baseball playing and even helping me out with college admissions stuff, since my folks were more blue collar. His dating life was really none of my business, but I felt like it was conversation worthy. "How long have you two been dating?"

He squirmed in his seat and sighed. "A while... not too long..." he said then gave me a long hard look. "Listen, Luke, you can keep this between us, right?"

The blue eyes and handsome jawline and perfect teeth were gonna make me crush out a little on the man, like I did back in high school. "Absolutely," I replied. Earnest as hell.

He smiled. He could read my sincerity, and I think it amused him. He leaned back and had a soft leer on his face, a side of him I'd never seen. "She's not my girlfriend," he explained. "I met her on one of those sugar daddy sites."

I may have been a dumb jock, but I figured out what he meant pretty quick. "You mean she's a hooker?" I asked. I had to laugh, and Mr. K laughed back.

"No, well, not exactly," he replied. "But there's a little of that, even if we both pretend that's not what's going on." His eyes searched out mine, and I knew he was trying to read if I was freaked out or judgmental. I wasn't, just surprised. 

I tried to pass off my shock with a joke. "She expensive?" I said.

He grinned, with a I-can't-believe-you-asked-that look. But he replied anyway. "Very. But I can afford it."

Something about his tone and lecherous nature got me hard. Not chubbed, but full on erect in my jeans. 

The man mistook my horniness for a different reaction. "Sorry Luke," he said. "I shouldn't have said that... only you asked."

"No, it's good," I assured him. "Just didn't expect it, is all."

"Fair," he said. He sighed again. "Seriously, Luke, not a fucking word to Rich. Or anyone. I mean it." 

"I won't, Mr. K, promise," I assured him. He probably didn't want to talk about it anymore, but I was very curious. "So... how's it work exactly?"

"How's what work?" 

"The sugar daddy thing."

He seemed more businesslike. Maybe he enjoyed being able to confide, or maybe he just was humoring me. "I pay for Kimberly's apartment and of course for dates," he explained. "There are gifts, too, but she doesn't make me jump through hoops like some of the others." 

I was letting it sink in that this one wasn't Mr. K's first. I knew the guy was loaded, but that kind of money was wild to me. 

"Damn, I should get a sugar daddy," I joked.

Without missing a beat, Mr. Keenan shrugged his shoulders and said, "You could. If that's what you wanted."

I blushed. I was still pretty closeted though Rich Keenan knew. Maybe Mike Keenan knew too. 

The man seemed to enjoy catching me off guard. "A colleague of mine goes for high-class call boys, but I've been trying to convince him to go for something more legit." This was definitely a new side to Mike Keenan than I'd seen. 

He paused. "Sorry, Luke. I'm not really suggesting... You know that, right?" The old Mr. K was back.

"Yeah, Mr. Keenan," I said. I wasn't totally naive, but this evening had already made me feel more green than I wanted. 

He held up his empty rocks glass in a gesture for the bartender to bring another. He then turned to me. "You have any special man in your life?"

So Mr. K did know. 

I shook my head. "I've hit the apps some," I said with candor. "But no one special."

He patted me on my shoulder, like he used to back when I'd come over to visit Rich. Like a buddy or a dad. "Well, you've grown into a fine young man, Luke Bowman. I'm sure that someone special will come soon... maybe when you're not expecting it." 

OK, I was more than a little crushed out. 

***

Something about seeing Mr. Keenan was a spark in my life that I needed. I'd spent too much of my college years scared. Scared of getting out there, of meeting men. I liked men who were older. Coach types, though that was out of bounds and not realistic. But I changed the age range on my app profile and decided I was going to be open to engaging with men who turned me on there. 

It was hit or miss. I heard from some real obnoxious guys. I went on some dates with a really fucking hot doctor who was great sex but then basically ghosted me. I had a couple of hookups that were good for what they were. 

I wasn't being a man-whore exactly, but I enjoyed making up for lost time a little. 

Strangely Mr. K became my confidante. I don't know why I thought the man would be homophobic, hell maybe deep down he was, but we each shared a secret with the other. And once he was back in DC for business that spring, I met him every other Wednesday for burgers and beer, depending on my game schedule. I got the increasing feeling that he valued his time with me, since he and Rich didn't get along well these days. The man carried a lot of guilt for his broken marriage, but he'd be the first to admit that he'd probably do the same thing all over again.

"Buddy, college girls are the best," he leered one Spring night as we finished our meal. Mr. K let his hair down a LOT with me these days. "I know they don't do anything for ya, Luke, but Jesus, fuck..."

I laughed. I knew Mike Keenan was a grade-A horndog and probably not a good man in that way, but I enjoyed seeing his naughty side. 

"You ever think about dating one for real, Mr. K?" I asked. For most of our meetings, it had been mostly my buddy's dad asking me about my life, but it was just now getting to the point where I felt like I could ask personal questions like this. 

He shook his head. "It wouldn't work. Besides, I wouldn't do that to Rich." It was a strangely profound admission. 

I gulped. Yeah, I could see it from my buddy's perspective, having a stepmother his age, or younger even. 

"That's cool, Mr. Keenan. But you gotta live your life, too," I said. 

That caught the man off guard. He looked at me then smiled. He reached over and ruffled my hair. "You really think that, dont ya?" he asked.

I nodded, embarrassed. 

He grinned. "Don't worry, kiddo. I'm enjoying my middle age years. A little too much."

"With Kimberly?" I prompted. He hadn't mentioned her in a while.

"I called off that arrangement," he said bluntly. "She wanted more."

"A ring?" I laughed. I didn't get straight people, not really, but at the same time they were my entire world. 

That leer returned to the man. "No. More money. I'm taking a break for now."

"How long will that last?" I teased. 

"Dunno. A month. Maybe two. Till I get horny again."

"I'm pretty sure you wouldn't have to wait that long to get laid, Mr. K."

It was meant as a playful comment, at least in my head. But the second it came out I realized I'd said too much. That Mr. Keenan could read everything in my face, everything I'd kept hidden. How attracted I was to him, how crushed out I was on him, how jealous I was of Kimberly or whatever sorority chick he was banging. 

The look on the man's face could now see it all.

Tears welled up in my eyes and I started getting a panic attack. I stood up from the bar stool. "I should go," I said. 

A hand reached out and gripped my forearm. Mr. K's grip was surprisingly strong. "Luke. It's OK."

Somehow, his understanding made it worse. I shook my head and broke free. "Sorry," I muttered. Then made a beeline for the door.

I felt dumb and intensely vulnerable as I walked to the bus stop. I'd messed up this friendship thing I had with Mike Keenan, but maybe it was fucked up that I was hanging out with my friend's dad like this in the first place. No maybe about it: it was majorly fucked up. 

I was a block away from the stop when I got a text. 

"Can I convince you to come back, Luke?" the man wrote. "I get it buddy."

I knew the smart thing would be to keep walking. To send a polite no thanks reply. Or just ignore the text. Instead I typed. "Yes Mr. K." And I walked back to the restaurant. 

Mike Keenan was standing outside, looking handsome as fuck in his expensive suit. He had a worried look on his face, and I knew immediately he'd dashed out after me but didn't know which way I went. 

His face brightened when he saw me. "We don't have to stay here," he said. "I settled up."

"Oh," I said. "Sorry..." I started to apologize, but he stopped me. 

"You were honest," he said directly, blunt but still friendly. "Besides, what man doesn't like to hear he's attractive?"

I gave a wan smile and hunched my shoulders in a shrug. "A lot of straight men, I imagine."

I couldn't tell if Mike Keenan was just humoring me. He had a look of sympathy on his face for sure as he reached out and patted my arm. "How bout this? No labels between us, Luke?" 

I didn't get what he was saying exactly, but I knew it was meant to reassure me. I nodded.

"Feel like coming to my hotel?" he asked. "We can just talk."

"Yeah." I was feeling a ton of emotions coursing through me. But I wanted more Mr. K time. "Sounds nice."

That seemed to relax him and put him in a good mood as we walked the few blocks to the nice, business-class residence hotel where he was staying. I couldn't help but sneak looks over his way. He just looked incredible in his suit, not a trim cut one like younger guys sometimes wore, but it still flattered his build and height. In my mind, the suit made him look like one of those DC power players and in some messed up way that turned me on. 

We weren't too chatty as he led me up to his room. It was fancy to my eyes but had that empty aura that hotel rooms do, even if Mr. K's luggage and belongings were around.

I was looking around the place when the man stepped up right behind me and wrapped his arms around my midsection. I smelled his cologne and felt his kisses along my neck. I guess we were going to do more than just talk.

"Oh, God, Mr. K," I hissed. This probably a record time for how fast I could throw hard. That boner was nearly instant.

"You can call me Mike," he said. 

"OK," I said dumbly. 

His hands traveled up and down my T-shirt. I was primed to be turned on by this man, but he was going to put me in heat.

"You OK with this, buddy?"

"You have no idea, Mist.. Mike" I replied. 

My slip up got a chuckle from him. His fingers slipped beneath the hem of my shirt and the touch of his hand against my belly felt electric. "You have an amazing body, Luke."

"You too, sir," I replied. 

He kissed some more along my neck and his voice got deeper, hoarser. "Do you suck cock, Luke Bowman? I don't know that I'm good for all the other stuff," he said, "but I'd REALLY love to feel your mouth on me, buddy."

I knew what he meant. The man wasn't going to reciprocate, and I'd have to be fine with that. I was. "I don't need anything in return, Mike," I said. "I want to suck you."

The grunt from the man was an indication I'd said the right thing. He had that huge horndog grin on his face when I finally turned to face him. We were matched in height but he felt like my opposite in so many ways. Older, successful in his career, straight, though I was getting the fuller meaning of his "no labels" comment.

Especially as his face inched in and his lips met mine. I was kissing Rich Keenan's dad, and the forbidden nature of that just added to my thrill. I took a second to feel up his sides, under the suit coat. Mr. K didn't object, he just went deeper with the kiss. Mike Keenan was a great kisser.

"You're a very handsome young man," Mr. K finally said as he pulled back. 

"God, Mike," I grunted. This was every JO fantasy I'd had coming to life.

With that naughty look on his face, he reached down and started unzipping. I didn't even look down, not yet, but I could tell from his shoulder motion that he was hauling out his cock. 

"Please, buddy," he hissed. 

"Here?" I asked dumbly. In my hookups before BJs had been naked and on a bed. 

"Here," he growled. This was that other side of Mr. K, the kind who hired sugar babies to get his needs taken care of.

I squatted down. I was a catcher for the Hoyas baseball team, so at least I had this motion down, I thought to myself. 

Mike Keenan's cock was gorgeous. Big and meaty and cut but not overly long. It jerked and pulsed as he looked down on me.

"You done this before, right?" he asked. That concerned paternal voice coming out.

I nodded. "Some," I replied. "I wish I had more practice." Then with an honesty I probably shouldn't have had, I added, "I want this to be good for you, Mike."

He chucked and moved his hand to run through my hair. It was strangely affectionate. "You'll do great, buddy."

That was all the encouragement I needed. Leaning in, I could smell the mild, natural musk of a man's crotch, which was matched by Mr. K's saltiness as I began licking him. I gripped the base of his prick to steady it for my sucking, but I maybe didn't even need to do that. Mike was rock hard. 

"Yes..." he hissed as I went down on him. I was still pretty green at sucking cock, but I was probably better than Kimberly or whatever sugar baby he'd lined up in the past. Or even the former Mrs. Keenan, I thought crudely. 

That knowledge had me going for it. I swallowed four inches of the man in one go, held just a second to let my throat get used to it. Then I started going up and down. It took a second for me to get my rhythm and another for me to get the suction. But I knew I did by the urgency of the man's fingers in my hair, not exactly pushing me down on his crotch but aiding and guiding me in my bobbing motion. He was probably thinking of some chick while I blew him, but I was OK with that.

Only his next words broke me of that idea. "Luke, buddy... you're getting me there," he hissed. Mr. K was very present in this blowjob. I paused a second and looked up at him, and could see he was looking down at me. 

I wanted to get him off. So I looked back forward and went for it. The best I could deliver. I hoped it was enough.

The fingers grew tighter. "Gonna cum... Don't pull off," Mike growled. "Please."

At that moment I felt bad for straight men. Even if I should have felt bad that Mr. K wasn't gonna suck me. I just felt any woman was stupid not to want to swallow Mike Keenan's cum.

"UNNFH!" came the sound of his release as he flooded my mouth and throat with his salty-sweet cum. Maybe Mike was backed up, but he was a heavy shooter all right. I accepted it all, swallowing it in waves as quickly as he fed it to me. I think my sucking sensation only added to his orgasm. He finally pulled out, prick wet and still hard. 

"God fucking damn, buddy, that was great," he said with a satisfied smile. Then as he caught his breath and I stood up, he added, "Can I jerk you off or anything?"

That sounded great. "You got any lube?" 

He nodded and walked over to the bathroom to root around his toiletries bag. He stepped back in, his prick softer but still sticking out. With a grin, he tossed me travel container of lube. "Don't be shy," he said. 

I was already undoing my shorts, which fell to the floor. Then I peeled down my underwear, letting Mike see my hardon. It was a trip for me, being mostly naked in front of him. Maybe he wasn't gonna be fully gay for me, but he was open to seeing my dick as I squirted the liquid on my stalk and start stroking. 

With a grin he stepped up to me, a little to the side, placing his hand on my belly and working up beneath my shirt as he met me for a kiss. 

That's all it took. I didn't come instantly but instantly I began that climb to orgasm. Mr. Keenan's kiss and touch was the extra stimulation to get me there. 

I moaned into his mouth as I shot my cum, shooting out onto the hotel carpet. 

He broke the kiss when I was done and patted my chest. "You needed that, buddy," he said with satisfaction.

"I did," I nodded. "Thanks."

Things felt a little awkward now. I'd crossed some major lines with this guy that evening, and now that I'd gotten off I felt majorly self conscious about it.

"You OK, Luke?" he asked as we tucked back in.

"I'm OK, Mr. Keenan." 

"You can NEVER tell Rich about what just happened," he said. 

"You know I'm gonna keep everything private," I said. "You can trust me."

He nodded. "Why don't you get cleaned up. Feel like a drink? I have some scotch here or you can raid the mini bar."

I nodded. "I don't know anything about scotch, but you can teach me."

He chuckled. "All right."

It felt nice to just talk. Mr. K let me open up, about men and being gay and what I really wanted from dating and sex. The man talked about his very limited experience with guys when he was a teen. 

"I should have figured men would be better at giving head," he said with a playful leer. "That was incredible, Luke. For real."

"I'm glad," I said. Maybe this wasn't a healthy hookup, but it had felt incredibly satisfying for me, a dream come true. 

"You're going to make some dude VERY happy," he said with a smile.

"I hope so," I said with a defensive chuckle. "I hope he makes me happy too."

Mr. Keenan got what I meant. "Yeah, you deserve that," he said a little chastised. He polished off the last of his liquor in the rocks glass. "Listen, it's been a long day."

"Yeah, I'll head off," I said, drinking the rest of my scotch and standing up. 

Mr. K pulled his walled out and fished out a couple of twenties. "Here you go... you're not taking the bus back. Especially at this hour."

I tried not to take it. "It's Ok, Mike," I said.

He shook his head. "Just get a fucking Uber, Luke. I insist."

"OK," I said, capitulating. The man could be bossy, and I didn't know whether I liked that or not.

He was quieter now, as he led me to the door but he said before I stepped out. "I'm gonna sleep like a baby tonight, buddy. Thanks."

"Thanks to you too, sir."