Daddy Playdate Ch 17

Josh:

"Thank you so much, Corey, you are the best!" I thanked Corey on the phone, as I stood naked in the bathroom.

"No problem, have fun with your date." Corey said, "And tell me all the details...I mean everything..." I could hear his smug face over the phone as he spoke.

"Fuck no, you creep!" I laughed.

"Oh yeah? That means you're finally fucking Adam tonight, huh..."

"Just pick up the kids...Bye." I rolled my eyes, and hung up the phone. Corey was kind enough to help babysitting the kids, so Adam and I would have a peaceful and quiet night alone for the date, but that didn't mean I was going to give him all the private details...yes, I was planning to finally fuck Adam, or rather, Adam could finally fuck me.

I stood in front of a mirror, checking out my own body. I want tonight to be perfect, I know Adam has seen my body plenty of times, but tonight is different, it is our first official date, it should be special. Fuck! Do I look sexy enough? I know I'm not bad looking, but I wish my pecs were bigger, and more defined abs...I've seen people with the perfect bubble butt, mine is a lot flatter...Adam's ass is round and thick, he won't think mine is too flat, right? My cock does look bigger after trimming my bush, I should do it more often...Damn it, I need to stop checking out myself, I don't have much time...thank god Brad gave me a check list. I have no idea how to prepare for a date, it has been a while...ok...trim beard, check...trim pubes, check...clean my hole, check...deodorant and cologne, check...that leaves the outfit...

I sauntered to my bedroom naked, and opened my closet. I knew exactly what to wear. At the bottom of a drawer, I found a red jockstrap. I bought it a long time ago when I saw someone at the gym wearing a similar one, I was so turned on by it I just bought one to try it on. It accentuated my ass and bulge significantly, but I only wore it that one time, for myself. I was still married back then, it didn't feel appropriate to wear something like that for my wife, and I certainly didn't want any hint revealing my attraction to men, so I hid it. But today was the perfect day to finally put it on, I was excited to show Adam my sexy surprise, and the easy access to my ass was a plus.

I put it on and checked myself out, happy with the form fitting jockstrap, I moved on to put on my khaki pants and blue dress shirt, I didn't bother with a tie, I didn't want to to be too formal, and it was going to be taken off later on anyway. I specifically found a tighter, more fitting shirt, I could see my muscles bulging as I moved. I turned around and checked out my ass, the jockstrap definitely helped make my ass look thicker. I was satisfied with how I look, I was feeling sexy, I was ready for the date.

Adam:

Fuck! I am so late! I didn't even have time to shower before I left the station, I'm already an hour late. I stink...and smell like sex, well...I fucked Mike, what was I thinking? You idiot! I can't believe I'm late to my date with Josh because of my horny brain...Fuck! I mean...you can't fully blame me, right? That guy Rob sent me a suspicious photo, Mike was all tied up in it, what am I supposed to do? Just leave him like that? I'll admit, I got hard looking at that photo, he looks sexy as hell tied up like that, I guess that's why I didn't resist much was the option to fuck Mike proposed, I was so horny...I supposed I should have left when all the miscommunication was cleared up, but I couldn't control myself, his hole was so inviting...and...it felt so good, my dick is getting hard again thinking about it...

I hurried to the restaurant Josh picked. It wasn't too fancy, but fancy enough to feel underdressed in my t-shirt. My heart was pounding, both from being nervous with the date, and also the guilt. I looked around, the place looked busy, but I didn't see Josh at first glance.

"Hey, excuse me, is there a Josh Cooper here? The reservation was an hour ago, I'm late." I grabbed the waitress's attention and asked, I was panting from the half running to the restaurant.

"Josh Cooper...Oh! The guy who was sitting alone...I'm so sorry sir, he just left." The waitress said apologetically.

"Shit! Um..thanks for the help." I said, and quickly turned around. I pulled my phone out, I needed to call Josh immediately.

"Hello! Josh! I'm so sorry, I'm late. Where are you?" As soon as the call was connected, I blurted out.

Josh didn't say a word as I spoke, and he remained silent after. My heart clenched, the nerves were getting to me, so I continued speaking, "I...I got caught up at work, someone needed my help...I'm very sorry, I'll make up with you, I swear..." I lied, well, not exactly, I thought Mike needed help.

"You were working?" Josh finally spoke, "Working with Mike?"

"Um...yeah? He's my partner..." I felt guilty for saying this, I was lying to Josh, I felt so bad doing this to him. No way in hell will I admit fucking Mike right before going on a date with him, I had already done enough damage for being late.

"I...I need some time alone..." Josh said, his voice was shaky. My heart skipped a beat listening to him, "Please don't call me, not now." With that, he hung up. I stood with my phone in my hand, defeated.

What the fuck was that? Was he crying? It sounded like it. Fuck! Did I really mess up that much? I know I was late, but that seems like a little bit overreacted. I was panicking, I needed to talk to Josh. I went to send Josh a message, I wanted to apologize again, and salvage the date, but my face went pale as I was typing in the apology. There was a video that I sent an hour ago. Well, not me, but someone sent a video through my phone, and just looking at the preview image, I knew exactly what that video was about. It showed my full rear view, completely naked, a pair of legs were raised, wrapped around my waist. There were no mistake of what this video is, I was fucking Mike.

"Fuck!" I yelled in the middle of the street, people were looking at me but I didn't care. Rob...It must be Rob. He secretly recorded me fucking Mike, and sent it to Josh. I was furious, not only did he invade my privacy, he potentially ruined my relationship with Josh. There was no going back from this, it was worse enough to ghost Josh to fuck Mike, and I just realized I basically lied to him face, he knew what I did the whole time we were on the phone. There was no apology that could fix this, I couldn't think of anything I could do to mend this. I took a deep breath, controlling my anger and the urge to find Rob and punch him in his face. I looked around, and saw a pub around the corner, and I slowly headed there. I need a drink.

Josh:

I sat in my car for a while now, calming myself down. I'd never felt more heartbroken, not even when I got divorced. This just showed how deeply in love I was with Adam, and how much he wasn't in comparison. It all started making sense now, why Mike was acting suspicious at the hospital, and why they always seemed very close even as partners. They were fucking, behind my back. I had no idea this was going on, and even though we were never exclusive, I thought we were heading that direction. I was going to ask him to be my boyfriend, but that all went down the drain, I guess we were not on the same page.

I sighed, and basically dragged myself to my apartment. The kids were still with Corey, I would have a few hours left to get myself together. As I walked up to my door, I saw Caleb pacing in the hallway, shirtless.

"Oh hi Josh...this is awkward..." Caleb said, he raised his hand to scratch his head. Caleb looked good shirtless, he was lean and fit, his chest was covered with thin light brown hair, and his armpit was a lot hairier in comparison. I was surprised to see he had a pretty six pack, he didn't strike me as someone who worked out a lot. "I locked myself out, I didn't bring my keys when I was throwing out the trash. I'm waiting for the locksmith."

"That sucks...hey, would you like to come in, you can wait at my place." I said. Oddly enough, I felt more calm with Caleb's presence. Perhaps it was the fact that I knew he was going through a divorce, he would relate to what I'm feeling right now, and I need someone to talk to.

"I don't want to intrude, you...you look like you are busy, all dressed up and everything..." Caleb hit a nerve, I could feel my eyes starting to get watery.

"No...I was going on a date, but...it's not happening." I opened my door, and invited him in.

"Sorry, that's her lost then, you look sexy...I mean, you look great."

"It's a he...he was fucking someone else and missed the date..." I said, and I couldn't hold it any longer, tears started running down my face. "I'm sorry...I'm a mess. Damn it, I promised to hang out with you, not like this, you have a lot on your plate already..." I wiped my tears, almost breaking down in front of Caleb.

"Don't apologize, you're not a mess, you have no idea how many times I cried alone...shit, I didn't mean you are alone, I mean I'm alone...I...I should stop talking..." Caleb pulled me closer and wrapped his arm around me. His body was warm, hot even, I could hear his heart beating as I rested my head on his chest. I looked up, and Caleb was staring at me, I swore I could see the lust in his eyes.

Get your shit together, Josh! Caleb is straight, and he just got divorced. Just because you are horny and vulnerable doesn't mean you can go after your straight neighbor. But what if...what if he is interested? Can it be possible? I mean, I was married, and look at me now, getting his heart broken by another man...

"Sorry, let me freshen up a bit." I pulled myself away from Caleb, and headed to the bathroom. Inside, I looked at the mirror. It wasn't a good look, my eyes were all red, I was sniffing from the crying, my shirt had marks of tears dropping down. I washed my face, and took my shirt off, and before I was about to head back out, I stopped. I unzipped my pants, and dropped them down. I stepped out of them, taking the remaining clothes off, except for my red jockstrap. Was this a good idea to walk out naked? Perhaps not, but I was at the point of not caring.

"You feeling okay...wow, is that a jockstrap?" Caleb said, slightly surprised at my lack of clothes.

"Yeah...my clothes are wet from the tears, this is more comfortable...hope you don't mind."

"I don't mind, it's your place, you can do whatever you want. I wouldn't care even if you are naked." Caleb grinned.

"Do you want a drink?" I said as I sauntered to the kitchen, "I definitely need one." I said, as I opened the top shelf, and took out the whiskey that I hid from Peter.

"Sure...are you okay?" Caleb asked.

"I'm better now that I cried...thanks." I said, and handed Caleb his drink. "Enough about me, how are you...you know, the divorce."

"It's rough, everything is finalized, and I know I'm the one who asked for a divorce, it still hurts. I know it's the right thing to do for the both of us, but it doesn't change the fact that I loved her."

"I understand the feeling...it takes time, but you'll feel better." I took a sip of my whiskey, and said. "You said you caught feelings with someone else, maybe you can ask her out? It helps to go out and socialize."

"I...I'm not sure they feel the same way...and I'm just out of the previous marriage..." Caleb said.

"There's no time like tomorrow! Just go for it! Look at me, almost 10 years alone with no one...don't waste anymore time, you'll regret it like me..." I said, as I took another sip.

"Yeah, of course..." Caleb murmured, "um...can I use your bathroom?"

"Go ahead." I said, and I took a big gulp, downing the remaining whiskey.

No time like tomorrow...why don't I follow my own advice? What am I afraid of? Fuck it, I'm gonna do it...

I slowly sneaked up to the bathroom, I could hear my own beating heart. I reached my hands out and gripped on the doorknob. Should I do it, this is my last chance to back out...

The alcohol didn't have an effect on me yet, I wasn't drunk or tipsy, but it gave me a good enough excuse to convince myself to go ahead. I turned the door knob and pushed the door opened, Caleb was facing away from me, pissing. His pants were slightly down, his hairy ass was in full view.

"I need to piss too...I'm joining you." I said, as I stepped next to Caleb, and pulled my cock out. Both of us were pissed in silence, Caleb didn't flinch at all from me barging in uninvited, his occasional glance at me gave me the courage to gawk at his cock. His cock was thin and long like him, resting on his low hanging balls. I was expecting his bush to be hairy and wild like his armpit, but it was neatly trimmed. I kept on staring at his beautiful cock, I wasn't peeing at all, my cock grew in my hands, until it was at full mast.

"You have a nice cock..." I said, my hands moving up and down the shaft slowly.

"Um...thanks? You too..." It seemed like my compliment broke to tension, as Caleb was now staring at my stiff cock directly. He finished pissing already, but he did leave. He was holding his cock, which was semi hard, nodding as it grew in size.

"Do you want to touch it?" I said, I turned slightly, aiming my hard cock at Caleb.

Caleb gulped, he hesitated. His cock was rock hard now, he wasn't much of a grower, but his 6 inches cock looked impressive pointing up.

"Touch it, feel it in your hands." I said, as I released my cock. I grabbed Caleb's empty hand, and guided him towards my throbbing cock, and closed his fist around my shaft. I moaned as he tightened his grip, I could feel his hand slightly shaking.

"Yes...jerk me off...please..." I groaned. With that, Caleb began stroking my cock, it surged as he reached my tip, and he rubbed it in a circular motion. "Oh...fuck! You are great at this..." I moaned, and turned to Caleb. His face was flushed, his mouth was opened slightly, breathing heavily. He was stroking his own cock while jerking me at the same time. He seemed to notice my gaze, as he looked up and looked into my eyes. My heart skipped a beat, Caleb looked incredibly sexy. It was almost involuntary as I leaned in and kissed on his lips, he was surprised by it, but he smiled, and kissed back. We pressed our lips together for quite awhile, kissing and sucking on each other's lips, our tongues intertwined.

"I want you to fuck me...I need it." I whispered, as we finally broke apart.

"What? I...I have never done it...I mean...with a man..." Caleb said sheepishly.

"Me neither..." I replied, "Today is the day...I want my hole to be filled...Will you take my virginity?"

Caleb nodded. I leaned in to kiss him again, before I guided him to the bedroom. I laid on my back, lifting my legs up, showing my hole. "Fuck me...Caleb...I want your big cock..." I groaned, as I reached down and teased my hole with my fingers.

"I...I don't know how..." Caleb said quietly.

"Come here..." I said. Caleb climbed on top of me, as I grabbed the lube on my nightstand. I grabbed his hardened cock, I gave it a few tugs and lubed it generously, and aimed it at my tight hole.

"Push in gently...don't stop unless I ask you to..." I said. I could feel his cock pressed against my hole, his soft tip slowly sinking in, stretching my hole open.

"Ugh...your ass is tight..." Caleb moaned as he shoved his cock in, it felt amazing feeling his hardness sliding in.

"Fuck...fuck me Caleb, fuck me with your big cock..." I cried out loud. It was better than I imagined, his cock reached deeper and deeper, until his torso pressed against my thigh, I could feel his cock throbbing inside me. He kept it in for a moment, and he started pulling back, and about half way through, he thrusted forward, slamming his cock deep in me. "Oh my god! Ugh...this is incredible..." As he continued to fuck me, plunging my hole, my cock twitched with each thrust, I could feel his cock rubbing my prostate as it went in and out, precum oozing out my tip, and dripping down onto my abs.

"Your hole is so warm and tight...fuck, I'm cumming soon..." Caleb was panting heavily, he was pounding me faster and faster, his cock surges within me.

"Come in me...fill my hole with your cum..." I yelled. Caleb got increasingly excited, fucking me harder and harder, and with one loud growl, he plunged in me deep, his cock exploded, I could feel his cum unloaded inside my hole. Caleb collapsed on me, his spent cock slipped out.

"That was great...you are a quick learner..." I said, as I wrapped my arms around him, and kissed his cheek. "Can you get up now? I still want to cum..." Caleb pushed himself and sat on the bed. He looked at me, and turned to stare at my leaking cock. "Maybe you can help?" I said, as I grabbed my cock and started stroking.

Caleb kept staring, I had no idea what he was thinking, but eventually he muttered, "I...I'm so sorry...I need to go..." He quickly zipped up his pants, and hurried out of the door. I didn't know how to react, other than sitting up and staring at the door. I felt empty, both physically and mentally, I thought to myself, "I think I made a huge mistake."