Daddy Playdate Ch 22

Jack:

I was deep in sleep when I was woken up by a warm body, snuggling in my arms. "Morning...honey..." I murmured to my wife, half awake still, eyes closed, I had no intention to get up. Still in my groggy state, I pulled her closer, we were both on our sides, pressing our bodies together. I was always horny in the morning, my morning wood poking her legs, I instinctively started bucking my hips, rubbing my hardened cock against her thighs.

"Babe...hmm.." I let out a deep groan, feeling the pleasure in my groin. I snuggled up and kissed her neck, my chest pressed against her back as I whispered, "Babe...I'm horny...I want my dick in you..." She didn't respond, probably still asleep, I continued to grind on her, my hard cock now lodged between her round ass cheeks, sliding along her cracks.

I wasn't going to fuck her without her consent, but it didn't stop me from feeling her up. I knew how to get her going, fun little foreplays that got me plenty of morning sex, I wrapped my arms around her, found her nipples and began to pinch and flick them. Something felt off though, but dazed with sleepiness and drunkenness that was slowly wearing off, I couldn't put my head on it, I continued to play with her tits, as I humped her back.

My cock was leaking precum, leaving her behind with slickness, I was gliding my throbbing cock up and down her crack, my horniness slowly taking over, I needed to fuck her. I could feel her waking up, shifting her body in my embrace, backing her ass against my crotch. "Yeah? You want my big fat cock? I'm gonna give it to you..." I thrusted my hips against her, while I retrieved my hands and slid them down from her back, until I reached her butt, before squeezing and kneading her round ass cheeks.

"Hmmm...babe...you are so fucking hot..." I whispered in her ear as I played with her ass, it felt bigger and meatier than I remembered, but it made me more turned on, who didn't want a thicker ass to play with? I messaged her buttocks, spreading them apart as I slipped closer to the middle, rubbing and lightly scratching her ass hole. She was hairier than I expected, was she not shaving her body? I didn't care, lust was taking over my mind, I was no stranger to ass play, and we had done anal from time to time, and today was one of those days that I craved fucking her ass from behind. I teased her hole and pressed my finger against it, passing through the resistance as I stretched it open and entered. She let out a sharp exhale, pushing back her ass as I probed with my finger, encouraging me to go deeper inside her.

Fucking hell, I'm so horny...I can't remember the last time I wanted to fuck her ass so bad...not gonna lie, seeing Adam plays with his ass made me so hard, he has a great ass, and he was so into it, I fucking came without touching his cock...I wonder if that's what she feels when I fuck her ass, it's so fucking hot if I can make her orgasm by fucking her ass...they say men have a g spot in their ass, does it feels better for men? Fuck! If I fuck Adam, can I fuck the cum out of him? Adam...Adam...why do I feel like I'm missing something...

I was lost in my mind for a moment, something was clicking, falling into place, I was connecting the dots, but ultimately I gave in to my desire to fuck my wife, I shook off the feelings and continued to shove my finger into her hole. I explored the inside, sliding in and out, stretching her hole open to prepare for my thick member to enter.

"Are you ready...I'm so fucking hard right now..." I finally pulled my finger out, my thick cock found its place in her crack again, rubbing against her hole this time, ready to go in. I could feel her backing up, I reached around to grope her breast as I thrust forward, my cock slowly pushed through the tight muscle, I moaned as the tip penetrating passed the ring, I hugged her tightly, and kissed her neck...something was not right, her chest was hairy, and firm, my hand slid down to her equality hairy abs, tracing down to her lower abdomen, something was poking my hand, I touched and wrapped around it, feeling it throbbed and pulsed in my palm. I finally opened my eyes, and I stared at the short reddish brown hair, it was unlike the hair of my wife, long wavy blonde. It suddenly hit me, remembering what was happening the night before, it wasn't my wife sleeping next to me, it was Adam.

Oh my fucking god! What the fuck did I do? I...I was groping him, I fucking fingered his asshole, and I'm about the fuck him! Why didn't I realize it sooner? It is so obvious now. Is he awake? He should be, right? He was moving. Why didn't he stop me? Or did he want me to fuck him? Fuck! What should I do? I need to stop and apologize, this is inappropriate...but I'm so horny, it feels so good, if he wants me to...damn it! What am I thinking, this needs to stop.

"Fuck! Adam!" I yelled, my heart sank and I immediately pulled away from him. I sat up and caught my breath, calming myself down, before pushing Adam's shoulder attempting to wake him up. "Adam! Are you awake?" I asked, while Adam rolled over, and laid on his back. His eyes were half opened, his face was flushed, he was breathing heavily and as I looked down, I could see his throbbing cock glistening with precum.

"Were you awake when I..." I asked, and I already knew the answer. Adam nodded without saying a word, I had no idea knowing he was awake the whole time made this situation worse or not. "I...I'm so sorry, Adam...I thought you were my wife..." I apologized, trying to explain myself, when Adam interrupted me.

"Fuck me...Captain..." He whispered, "You can fuck me, please..."

"No! I'm not going to fuck you!" I exclaimed, "I'm your fucking boss! This is crossing a boundary."

"We jerked off together yesterday, the line is crossed already."

"That doesn't mean we should cross this line...and I'm straight..."

"So? I was straight a few weeks ago, and it seems like you were enjoying it." He said, as he glanced down to my raging hard cock. He was right, I enjoyed it, and I was fighting hard not to shove my cock in him.

"I...I'm not fucking you! This is the end of discussion."

"Why not? Please...just fuck me already...I need it..." Adam said, I could sense the desperation, and sadness in his voice.

"What is going on? Where does this come from all of a sudden?" I asked, "Are you okay?"

Adam remained silent for a moment, before opening his mouth, "You told me I should lose some steam, I should have some fun, so I'm doing that."

"That doesn't mean I should fuck you, just go out a find a date! Didn't you say you almost fucked your neighbor? Go fuck him, not me!"

"I...I can't..." Adam said, "I'm sorry, just forget it..." He paused, before speaking again, "I'm just tired. I'm tired of feeling sad, I'm tired of feeling guilty...Everything reminds me of Josh, every time I jerked off, I think about him. I didn't fuck my neighbor because I couldn't stop thinking about Josh, I...I always thought I'm going to lose my virginity with him, you know, explore being with a guy with him, but I fucked up. I fucked Mike. And now every time I mess around with a guy, I just feel guilty, and hoping that it could be Josh that I'm with..."

"Then why do you want me to fuck you?"

"I'm sick of feeling like that, and I just hope that you can fuck me to get it over with, to break this cycle of self loathing...and I trust you more than a random stranger on a date..."

"Me fucking you is not going to fix anything..." I sighed, "You are deeply in love with him...does he know that?"

"It doesn't fucking matter...He's not talking to me, I don't think he wants to see me..." Adam said, and his eyes started watering.

"Talk to him, tell him how you feel, that's what you need, not fucking someone to numb your pain. At the very least you'll get closure, you don't want to regret it for the rest of your life."

"I...I'll try...Thanks for everything you did for me, captain..." Adam said, "and thanks for inviting me here, it was a great time..."

"You're welcome, you better join next time, you are part of the group now." I smiled.

"Of course, how can I pass up jerking off with two hot men?" Adam smirked, "Maybe you can finger my hole for real next time."

"You little shit! It's a mistake, you better not tell anyone, especially Robbie." I grinned, "I'm not going to let him tease me about it."

"Well...if you're not going to fuck me, can we at least jerk each other off? Or I can ask Robbie to help me out next time..."

"Are you blackmailing me?" I laughed and smirked, "I guess I have no choice then." I said, as I reached for his hard cock, stroking it as he reached for mine.

Josh:

I was walking in the hallway to my apartment when I spotted Caleb walking out of his. This was the first time we saw each other since the incident where he ran after we had sex. I was contemplating if I should turn around to avoid him, when he approached me.

"Hey...Josh...can we talk?" Caleb asked.

"Yeah, of course. I have a few hours to kill before I have to pick the kid up from school...I need to talk to you too." I replied.

Caleb invited me to his apartment, and I was greeted by Cooper the dog. "Hey buddy! Long time no see! Peter misses you so much!" I pet Cooper as I walked in, I was immediately calmer than before, breaking the tension for whatever awkward conversation you were about to have.

"He misses you guys too." Caleb smiled, and asked, "Want anything to drink?"

"Not alcohol, don't want to repeat what happened." I said, "Just water is fine, thanks."

"Got it."

Caleb brought me a glass of water, and we sat on the couch. We sipped on our glass of water, neither of us wanted to talk first. I stole a few glances at Caleb, he was looking ahead, clearly avoiding eye contact with me, and probably doing the same as me, we sat in silence for quite some time, until we broke the tension.

"I'm sorry..." We both spoke at the same time, which surprised the both of us.

"I'm sorry. I panicked after...you know...after I fucked you, and I ran away..." Caleb apologized.

"No! You don't need to apologize. I am the one who should apologize." I said, "I...I was heartbroken, and I got drunk. I'm an idiot, I don't know what I was thinking, I...I guess I wanted revenge, I used you and came on to you, and I'm sorry for that. I knew you were straight, and I still did it, I never should have done that. Don't get me wrong, you are hot, I don't regret what we did, it's just...just not an excuse for what I did to you, it was for the wrong reason."

Caleb didn't say a word for a short moment, he simply stared at his glass, before turning his head to me. "You didn't come on to me..." he said, "I...I have something I've been hiding from you. I'm keeping a secret from you. Remember I told you I caught feelings with someone?"

"Yeah?"

"I...I like you Josh. You are the one I caught feelings with." Caleb said, as he stared into my eyes. It was a shock to me, I had never suspected Caleb to have been attracted to men, let alone have an interest in me, I sat in silence, processing what he told me.

"So your divorce...it is because of me?"

"No! Well, partly...Ashley is always away from home, and I was lonely. Talking to you and babysitting Peter is the best time of my day, and along the way I started getting feelings. I didn't know at first, I just thought I liked you as a friend, but I started getting these urges to see your muscular body, fantasize about kissing you...I realized how unhappy I was with Ashley, and you convinced me to get a divorce. I never thought I'll be with you or anything, I just thought I needed to explore this new side of me, and then we did what we did..."

"Wait, then why did you walk out? You wanted to have sex with me right?" I asked.

"I did! And I enjoyed every second of it...but it all happened so quickly, one moment I was hiding my crush from you, the next second I had my dick inside you...I don't know, I just panicked, I guess I was worried you would figure out my secret, I felt like I took advantage of you...I know, it's stupid."

"I didn't know that's what you were thinking, I just thought we panicked because you fucked a guy..." I said, "I understand, I was in your shoes. When I first messed around with Adam, I almost stomped out of the room after we came, luckily he stopped me before I could." I smiled thinking back to the first time with Adam.

"So...I guess the cat's out of the bag..." Caleb shrugged, "I understand if you don't want to do anything with me anymore, I just want to let it out of my chest..." Before Caleb could finish the sentence, I leaned in and kissed him. It surprised him for a moment, but he kissed back eventually, and we sat there kissing until we were out of breath.

"That...that was unexpected..." Caleb said as we broke apart.

"I told you, you are hot." I grinned.

"Can I...um...can I suck you dick?" Caleb asked bluntly, "I've been thinking about it...I want to try it."

"Yeah? Why don't you pull it out?" I said as I leaned back, spreading my legs. Caleb reached for my pants, unzipping it before pulling them down, my cock was already semi hard in my underwear. He kneeled on the floor, between my legs, he slowly peeled my underwear off, revealing my growing cock.

"It's beautiful..." Caleb gulped and said, he wrapped his hand around my thick cock, and gave it a few tugs. "I can't believe it's happening..." He said, inching closer to examine my cock, before putting it in his mouth. His tongue licked my tips, tracing the veins on my shaft as it slid in, my cock grew and surged in his mouth, I threw my head back trying to enjoy it.

It's not perfect, but his passion makes up for it...I can't believe it's happening, who'd have thought Caleb had a thing for me.  He is sucking my cock right now! I fucking miss having my dick sucked, Adam and I used to do it almost every morning, those were the best part of my day...I wonder what Adam is doing right now, is he getting blowjobs from his partner Mike? I...I miss him...maybe I overreacted, it sucks that he was late to our date, but...we weren't exclusive, he can fuck whoever he wants...I'm just jealous, I wanted to be his first, I wanted him all for myself...Why am I thinking about Adam when I'm getting my dick sucked by Caleb? Just stop thinking about him and enjoy the blowjob! Fuck! Why can't I stop thinking about him...

"Stop!" I yelled and stopped Caleb from bobbing his head on my cock.

"Am I doing something wrong? Did I hurt you?" Caleb asked with concern.

"No...you didn't do anything wrong, it felt great..." I said, "It's just...I'm sorry, I can't do this, not right now."

"Is something wrong?"

"I'm sorry...I didn't mean to lead you on...but you know my situation with Adam..." I said, and he nodded, "I couldn't stop thinking about him, and it's not fair to you when you have my cock in your mouth. I don't know how long it will take, but at least for now I don't think it's a good idea for us to fuck around, we both have our fresh wounds."

"I understand..." Caleb nodded, "Can we at least stay as friends? I would hate to see Cooper and Peter separated."

"Of course we can." I smiled, as I pulled up my pants, "And I would hate to stop seeing you around."

"Thanks..." Caleb stood up and hugged me, "For all it's worth, you helped me figure out my sexuality, whether you knew it or not...thank you."

"You are welcome. And you helped me go through a lot of hard times, thank you." I said, and hugged back, and stayed in this position for a long time, feeling each other's warm embrace.