Best Friend's Dad - Dinner After

(Continued from "My Best Friend's Dad - Mr. Anderson." Chapter 3 will flip power dynamics back ;) Enjoy!)

"It's Mr. Anderson, is this Jack?"

My heart skipped a beat. I pulled out my phone during my statistics lecture and saw Dan had messaged me. It had been three days since our encounter in the locker room, and I haven't stopped thinking about it since. It was my best friend's dad, which made it so wrong... and it made it so hot. I'd jerked off at least 6 times to that scenario alone. The way his body felt on mine, his rough 5 o'clock shadow, his veiny forearms. His meaty cock. I needed to see him again. I needed to play this cool.

"I think you mean 'Dan' :) Yes, this is Jack. Hope you're doing well! I had a great time at racquetball this weekend," I responded. Fun, flirty, but no explicit paper trail of what we did. I put my phone on my desk and glanced between the professor and any incoming messages I got, all unfortunately not from a hot 40-something guy.

I left lecture and went back to my apartment, just off campus. I shrugged my backpack off and took my shirt and shorts off since it was another hot day. I looked in the mirror and flexed a bit. Damn. I really liked what I looked like with my 6-pack and broad shoulders, decent pecs and biceps, solid quads, and not a lick of hair to be seen besides my shaggy hair on top. I was loosely what they called a "twunk." My self-ogling was interrupted by the ding of my phone notification. It was Dan!

"Haha. Yeah, me too. Family dinner tonight was cancelled, I'm suddenly free. Want to come over?"

Yes. God, Yes. I want to come over, cum on, cum in, whatever he wants. Whatever plans I had are now cancelled. But play it cool, Jack.

"Yeah," I typed out, "that sounds good to me. Say 7PM?"

I saw his typing bubbles pop up immediately. "Perfect," he sent. "See you then. Looking forward to it."

And I'm looking forward to much, much more.

I saw it was 5:45PM and decided I should shower up. I glanced back in the mirror, slid my boxer briefs off, posed just a little bit more, then and walked over to the shower to freshen up. After that, I brushed my teeth, put on some tight shorts, a flowy shirt, and headed out the door.

As I was driving up, I got hit with a sudden worry: What if Dan called me over to let me down gently? What if he regrets what we did and needed to break things off?. I swallowed hard and my heart started beating faster. Maybe I really messed up with this. However, all my worries flew away when I saw Dan sitting on the porch as I pulled into the driveway. He was sitting wide legged with his loose cargo shorts, a button up short sleeve shirt leaving not a lot to the imagination, flip flops, and a big grin. So he was happy to see me! Phew.

"Hey, Dan," I called out, waving with a grin to match his. "How's it going?"

"Ah, you know, can't complain. Hey, thanks for making it over here, I got a dinner all set for us." He walked us into the dining room and pulled my seat out for me. A gentleman. It looked like he made us a potato salad and steaks. He took the seat next to me and poured himself a glass of wine and gestured to my glass. I nodded as he gave me a heavy pour.

"Wow, Dan, this looks delicious. Thanks so much! Mrs. Anderson not joining us today?" I asked, sipping on my wine, hoping the answer was no.

"Nah, she's shacked up at her sister's for a few weeks. It's looking like things are finalizing with the divorce soon. I know Lisa told you, so no need to act shocked," he laughed.

"Yeah, she did tell me, but again, I'm really sorry to hear that. It must be tough on everyone." I tested the waters as I reached out to grab his forearm in a show of comfort.

"Thanks, Jack, I really appreciate it. It is hard, but I think we are both ready for other things in our lives. We grew apart and are both headed towards new things."

New things...? I hope that involves something that's between your legs and something that's between mine.

"Time will tell where you go, but let me know if I can ever help out with anything!"

"I appreciate it, there might be a few things later," he said, with just a hint of a smirk on his face. Hmm. So he is playing with me right now. Perfect.

I started to go in on the food, which was unsurprisingly amazing, and he did the same. We both started going heavy on the dessert and even heavier on the wine, laughing and talking about shows and movies we liked, our hobbies, how we grew up. We shared more in common than we think. I always thought guys like Dan, "real men," couldn't be relatable to me, but he definitely showed me wrong. After my third glass, I had to say something.

"Dan, I'm having a great time and this wine is great... and also strong. I don't think I'm going to be able to drive back any time soon." I left this open-ended to see what he would say.

Dan looked at his watch and said "Well, it is pretty late, by the time you sober up completely, it might be too late to drive back. Wanna shack up here?"

Yes. Oh, absolutely. Everything that shack up entails, I wanna do.

"Wow, thanks much! I think I might take you up on that offer. But I didn't bring any of my stuff..."

"No worries, you can use anything I have! Mi casa es su casa, right? If you don't have any pajamas, you can use something of mine."

I was about to tell him I didn't wear pajamas, just my underwear when I slept, but I stopped myself because I wanted to sleep in something he wore. Something that smelled like his natural musk. Some shorts his dick might have touched.

"That would be great, could I see what you got?"

"Yeah, of course, follow me."

Dan took the lead up the stairs and I followed after him, watching his perfectly sculpted ass climb up to the next floor. He led me into what I was assuming was his room, which had gorgeous large windows and a huge bed. A bed I hoped we would try something on very soon.

Dan rifled through his dresser and pulled out a pair of thin sweatpants; the kind where, if you turned, you could watch the outline of your dick swing after you.

"These ones are from when I was younger, maybe closer in size to you. You're more than welcome to try them on, if you'd like. It's late and I'll probably change into something more comfortable, too," he said as he pulled out a pair of silk boxers. Dan, you sly dog; silk boxers and trying to get me to change in front of you?

I grabbed the sweatpants and said, "Looks perfect, thanks. And I hear silk boxers are very comfortable."

"Oh yeah, I'm never going back," he responded as he started to unbutton his shirt. Fuck yeah, Dan, show me that huge, hairy chest.

He threw the shirt into the laundry hamper and, while keeping eye contact with me, slowly shimmied out of his cargo shorts. No underwear underneath. I glanced down and saw he had a half chub going on. Actually, now more than half a chub happening, growing from between those huge thighs. Fuck me sideways.

To my disappointment, he slipped his silk boxers on, but was very obviously tenting in them. "Let's get you dressed for bed," he said in a quieter, half gravelly voice. He was putting on his sexy daddy voice and I was listening, intently.

"Whatever you say, Dan," I replied as he reached for my shirt. He slipped it off me easily and took a few seconds to look at my chest, just inches away from me. He then brought his hands to my small hips and brought my shorts and underwear off at the same time. I had a raging erection that I was weirdly proud of. I wanted to show him how much I wanted him. He reached for the sweatpants and told me to step into them. What kind of daddy role-play are we doing, now? I thought to myself, but obliged. He had only a bit of struggle getting his sweatpants over my dick. I was throbbing just thinking about how his dick was touching the same pants mine was. He probably got hard in these pajamas and touched himself through these. Fuck. Dan started to push me backward onto the bed until I was forced to sit down. He pushed his hand into my chest until my back was on the bed.

"I just wanted to suck you through the sleep pants I used to wear. Thought it would be hot."

Oh my god, he's so sweet and hot at the same time. I could get used to this. And I wanted this so bad. Don't waste any time, Dan.

Dan then placed his hand on my dick through the sweatpants and rubbed at it, using some force. I humped against his hand for what seemed like forever but was probably 30 seconds. He then fumbled for the fly in the pants, reached inside, and I felt his warm hands grasp my cock and pull it out.

"Fuck, Dan, please suck me," I moaned as he gave me a slow handjob.

"Only because you said please," he grinned as he brought his lips to the underside of my cock and started to kiss it, starting at the tip, kissing down to the base, and then back to the top. He opened his lips and starting tonguing around my cock head before finally giving up his little tease and moved to the main event. He wrapped his lips around my cock head and slowly dropped his head closer and closer to the base of my cock until he had everything all the way down. He held himself there for a while while I enjoyed the warm sensations of this DILF's mouth enveloping my 6.5" cock. He wasn't able to do this last time, I thought to myself. He then used some new techniques, swirling his tongue around as he bobbed his head up and down, changing up rhythms and grip. Holy shit. I can't get enough of this. He's gonna need to slow down soon.

Dan came up for air and said "So, do you like?"

"Like?" I laughed, "Fuck, I'm a changed man! You're so fucking good at that."

"Ha, thanks," he let out, "I did some research on how to deepthroat better. Oh, and I put these on to tease you a bit," he said, gesturing to the silk boxers he put on to deprive me of seeing his glorious man cock. And research? It was so cute how he wanted to impressive. Cute and so fucking hot.

"Well, I'm sure the research was at least fun," I joked, "and it looks like the real-life application is very enjoyable... Want to try something?" I asked.

"Sure, hit me with it," he said.

I gestured for him to get up on the bed and I moved myself up as we both were kneeling, facing each other. I brought my hand up to his face and moved in for a gentle kiss. He responded with some pressure and I opened up his lips with my tongue, pushing it further inside as our kiss gradually turned into a full makeout session. My other hand was exploring his body, first his back, pulling him closer to me, then his huge, muscle-y arms, then his furry stomach, and then finally, I snuck my hand under his waistband and grabbed his cock, hard. He moaned into my mouth and I started to jerk him off under his silk boxers. I broke our kiss and pulled his underwear off as he waddled around so I could pull it completely off his body. I then pulled his sweatpants off my lower body, brought it up to my nose, and took a deep sniff. Mmm... it even still smelled like his cock. Dan took the sweatpants from me and took a sniff himself.

"Smells a bit like you on here, now. So fucking hot."

Oh, it's on now.

I pushed him down on the bed so he was laying down, and I angled myself parallel to him, on my back as well, and grabbed his cock.

"69." I said. I wasn't wasting any more time. I needed this cock in my mouth. Bad.

He seemed to agree as he shoved my dick in his mouth and went immediately to giving a thorough blowjob. I groaned as I licked his meaty cock from the base to the tip and worked the tip with my tongue before putting all 7.5" of him past my throat. I started to bob up and down on his cock and he kept moaning, which was putting vibrations on my dick. Goddamnit, this is the best blowjob I've ever gotten. And I get to have a real man's dick in my mouth while I get it.

We went like this for a bit before he popped off and brought my head in for a kiss. I returned it, letting my tongue go wherever the fuck it wanted. He then looked me in my eyes and swallowed hard.

"Jack, I've never done this before, but if you're down, let's take it to the next step."

Assuming he meant anal, I was all in. "Yeah, absolutely, let's do this. Do you have lube? Condoms?"

"Lube, no condoms, but I haven't had sex with anyone in the past 6 months and was tested, so I am good, what about you?" he said.

6 months! Wow, Jenny really didn't let him have it at all.

"Tested as of my last rendezvous, so I am good, too."

"Perfect," he grinned as he reached for the bedside table and brought out a tiny bottle of lube. He and I were both kneeling as he inched toward me, started kissing me, and brought the bottle above our cocks. He started to pour lube on my cock and rubbed it in a bit before turning around.

What? There's no way this man is a bottom. Does he want me to fuck him? I mean, I'm very and all, but what? He started to bend over and show me his perfectly shaved ass, muscle striations clearly visible from his hamstrings, putting lube on his tight pink hole. He was arching his ass and looking back over at me with a seductive look. "What are you waiting for?" he asked.

"U-uh, nothing," I stuttered out, taken aback, "I'm just a little shocked you're a bottom."

"I always like having things up my ass, and to be taken for the first time by a young stallion like you..."

"Wow," I let out, "uh, yeah, I'm absolutely in."

"Well, then, why don't you get in?" he retorted playfully.

The power dynamic was kinda hot to me. A young, sorta thin guy fucking this absolute man in all senses of the word, right up the ass? Count me the fuck in.

I grabbed the lube and stroked my dick with it a few times, then covered my right few fingers with some more as I starting toying with his hole. I circled his ring a few times with my pointer finger and slowly prodded his hole as I pushed forward. He practically sucked up my finger and once it was in, I pushed back and forth, using the "come hither" motion trying to find his prostate. Dan let out a manly, gravelly groan and I knew I found it. After stroking that for a bit, I entered one more finger in, then one more. He was ready to get fucked by a man half his age.

I stroked my dick one last time before I put it up against his hole. I slapped my cock around on it a few times and then pushed it into his hole. I got the head in and he was so fucking tight. I looked up at his face and he had a look of pleasure and pain mixed together. "You okay?" I asked, to which he only responded with a moan. Damn. He wants it bad.

I pushed my dick slowly further in until my balls were at his ass. God fucking damnit, this feels amazing. He's so fucking tight. I pulled out a bit, then was shocked for him to push back on it. Yeah, it's on.

I grabbed his hips, just above his ass, and pulled him onto me, really letting him feel every inch and every vein on my young cock. I slowly started to pick up the pace and could hear my torso and balls slapping up against his ass as I really started to fuck him. At this point, both of us were moaning so loud, I don't know who was enjoying it more, me or him. I wagered a few smacks on his ass, which were well received with a look of pure content, like he was made to be there, getting fucked.

Out of nowhere, Dan pushed forward and off of me and spun around with an intensity only a seriously horned up man could manage. He practically threw me onto the bad and straddled me, hovering his ass over my dick as he grabbed for my cock to point toward his hole. This absolute DILF lowered himself onto my dick until I was fully inside him. He started to bounce up and down and reached for his cock, jerking it madly. I was in heaven. Absolute, hot, sweaty, manly heaven.

Dan placed his left hand over my head as he brought his torso closer to me, violently making out with me while still jerking his cock. All the while, I was feeling his tight ass hug my dick like it needed it. This feels fucking amazing.

"Jack, I think I'm close." Dan whispered as he brought his forehead to mine, maintaining intense eye contact.

"Dan, I want you to cum for me. I need you to cum for me."

I felt him start stroking himself faster and knew my reward was coming, and fast. His hole started to contract around my cock and I looked into his eyes, Dan looking into mine as he let out a deep, long groan. "OH GODDDD" he yelled as I felt a hot shot of cum hit under my chin, another two on my chest, and three more on my abs. This was too much for me. I am gonna fucking cum. Holy shit. Oh my god. Oh fuck. "OH FUCKKKKKKK" I moaned as Dan's hole still pulsed around my cock, which was now shooting fat loads of cum right up his ass. I lifted my hips up to be as far inside him as I could as I spent myself inside him, shaking from the huge orgasm that just blew my entire body apart. Holy fucking shit. That was absolutely amazing, I thought to myself as I pulled him into me, his cum sliding between us as we shared a passionate kiss. We unlocked lips and looked at each other, both of us feeling a grin creep up on our faces.

"Jack, that was... that was..."

"Fucking amazing, I know. You're sure you never done this before?"

He let out a hearty chuckle. "No, but I'm very glad my first time was as amazing as this."

I could feel the oxytocin, the "cuddle hormone," running through my veins as I slipped my now softening dick out of him. He pulled the blanket we pushed off over us and wrapped his arms around me, facing me away from him so I was the little spoon. The difference in our body sizes was kind of incredible as he enveloped me in his huge arms, slipping a meaty leg between mine and putting the other over me where I was being only slightly crushed, but in a good way. He buried his face into my back, kissed it a few times, and I felt his body start to relax. I was so filled with content that I let myself drift off, tangled into his body, until I finally fell into a deep, sweet sleep.