Very important detail for those who are reading both My New Personal Assistant and HomHS

These two books are happening simultaneously, but in My New Personal Assistant, it is still only November 2019, while in HomHS, it is March 2020 (you can see this best in Nate's story ch. 1)

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This story is part of Project Cheaters (2020)
Trigger warning for this / future chapters: BDSM, cheating, seducing the brother-in-law, turning gay, trauma, PTSD, mentioning of homophobia.

All characters are consenting adults (18+)

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RICK

I woke up at 6. My inner clock worked again, even if I felt a bit tired. I looked at Nate, still asleep in the same position he was the night before. I loved what I saw. His face was so calm and peaceful while sleeping. I didn't want to miss a second of this weekend. Who knows how much will change on Monday? If anything, I decided I would enjoy it as much as possible.

I raised the blanket a little and saw his cock swelling. I went down to it and licked its full length before engulfing it with my mouth and feeling it grow. I heard a moan above, and Nate turned to lie on his back. I continued satisfyingly licking his shaft, which had instantly started filling to a full mast. I kissed his balls, taking them in my mouth and licking each. He put his hand on my hair, brushing it back.

"Good morning Richard." He smiled lazily.

I looked at him and started sucking him. His abs moved and twitched as he moaned. I sucked and licked his cock, gripping him at the base, and started jerking it at a fast pace. He growled and grabbed my hair, thrusting his cock in me. I felt his body jerk and balls tightened under his shaft when I pushed his cock into my throat. He screamed and cried out. He was cumming. His body shook under me as a couple of volleys of his cum filled my stomach.

I came up to him and kissed his lips.

"Good morning, Nathaniel." I smiled, and he hugged and rolled with me so that he came on top.

"My turn now."

"Be my guest, boy." With a wicked grin, he went down and took me to the base in about five trusts. Fucking hell, is this man for real? I sat up in shock. Is he secretly practicing somewhere, or is he just this damn talented? 

He gagged but was able to compose himself and started long-dicking his fucking throat! Who the absolute fuck is this man?! I didn't last more than a few minutes and was blasting into his mouth with a loud cry.

"You gotta be kidding me, man! Where the fuck you learned that?"

"Trade secret." He winked at me.

For real?! I remember the first time he sucked me. I believed he never did it, there were occasional teeth and gagging, and even the way he was holding it was odd in some way, but this fucking head was like a professional porn actor aspires to learn to do it. How the hell did he do that?

"No, seriously, man." I lay out of breath, my dick still twitching. "I'm starting to think you lied to me about never having a dick."

He laughed and left for the bathroom. He closed the door and, after a couple of minutes, came back.

"I wasn't joking."

"I really haven't ever been with a man Richard." He said plainly.

"Bullshit," I said in a mocking tone. Nate looked at me, confused. Finally, he saw that I meant it.

"Look, I was insecure about sex my whole life. Most of my girlfriends thought I had ED. So, I learned as much as possible about sex. I practiced licking pussy as one practiced musical instruments, regularly and methodically." He grinned 

"In the end, it's just skill. Once you master the basics, everything similar becomes easier. You just tweak it some way." He shrugged his shoulders as if he had just told me how to learn a new language. Damn!

"That's why you were so good at eating my ass?"

He chuckled at the compliment. He looked proud of himself.

"Well, to be honest, I specifically learned that because of one ex, she thought I would like it. And me being me, I took it very seriously to learn as much as I could. The gay sources were already more out, and thanks to the internet, I found out most on gay websites. But, if I have to say, back then, I thought of it mostly as practicing and performing. I was glad when they liked what I did, and if I made them come, I felt good. But it never excited me the way sucking your cock does for me. I feel like a whole different person when I am between your legs or having that thing inside me." He looked at my cock with nearly an appreciation. I must have smiled at that.

"Do you think she thought you may be gay?"

"If she did, she never mentioned it."

"Tell me her name and address. I feel like sending her some nice flowers," I said with a genuine smile. He laughed at that.

"Did you also research how to give a blowjob?"

"Yeah." He said it like it's the most natural thing one does.

"And you have practiced methodically?" I leaned in, ready to swallow him whole.

"Yes." He said slowly, looking into my eyes with those wicked green ones.

I would have dived on him hard if I hadn't blown just a few minutes ago. I felt excited, but my dick was a bit sensitive now after the treatment I just had and after shooting four times yesterday. It was fucking hot imagining him with that dildo of his, deep in his throat, practicing, thinking about pleasing me.

"You are fucking driven, boy."

"I tend to take my assignments seriously."

"My little achiever." I kissed him.

The morning was good. We made it out to run, eventually, even a bit later. We found a path with no people around, so we took our masks down. Enjoying the fresh chilly air. We weren't really looking where we were going and ended up in a spot with a view of the district below. We stopped, and I pointed to him a few places I could see from above here that I remembered growing up. We talked there for maybe half an hour about our childhood and fun memories from our teenage years. He was fun, and I don't remember the last time I laughed so hard. How could I think of him as a cold, strict man? I couldn't even remember now. 

We just walked from then on, talking. From what I learned, we had very different experiences growing up. I was a quiet kid who grew up all proper, with the best grades and no fun, and then making up for all the experiences I missed after I moved out of there. And damn, was I compensating a lot.

On the other hand, Nate was one of those cool kids and quite wild, based on his stories.

I found out that Nate is from a nearby city, and both of his parents are still living there, they don't talk much, but he visits a couple of times every year, they probably had some issues, but I am guessing that mainly from the tone he had when he mentioned them briefly. 

Nate mostly talked about his teenage times and early college years, he has had four best friends since childhood, and they haven't hung out much in the last couple of years, but they contact each other frequently. Only two are married like he is, and one is recently divorced. As far as he knows, they are straight.

"So, you've never experimented with them or jerked off together?"

He smiled at me. "I heard it's a wet dream of many gay guys imagining a couple of straight best friends jerking off together or experimenting in some way. But, no, we never even mentioned the idea. We goofed around, wrestled, and made sick jokes, but they were like brothers to me. I would run into a burning building for any of them. I never considered them in any sexual way. Even when we talked about porn, it was mainly informative than anything else."

"Shame. It would be hot to imagine you all jerking together."

He laughed at that. "I believe it could be for you. Sorry to disappoint. But even making that up just for you would feel weird for me."

"Have you told them back then?"

"About me being asexual?"

I nodded

"Yes, they were the first I ever told. It was one of those beer talks we had where we started talking girlfriends and porn." He looked at me, and when he saw my interest, he just continued in a way like 'what-more-is-it-there-to-say'?

"Well. I was young, maybe 15 or 16, and I mentioned that I wasn't attracted to my then-girlfriend. She was hot by their standards, and I was with her because she wanted me, and all of them already had someone. So John told me that maybe she just wasn't my type, and Dan insisted I should sleep with her so I would see what it was about. Brandon, I remember, told me that if I was not into the girls all the more for them, to just pass them down to him." He laughed for himself at that memory. 

"We had a blast in those days. I don't know if I was worried before, but I could tell how it really was when I was with them. When I slept with her, I was genuinely disappointed and told them I might not work that way. They have been good and had some funny remarks, but every time something like this came up, they became more used to the idea that I am not that into sex. They accepted it and were an amazing help when I struggled to keep relationships. I didn't want sex, but I didn't want to be alone. I wanted someone by my side to have something intimate."

"Neither of them mentioned the possibility of you being gay?"

"Sure, they have. Being gay was more known than being asexual. That one came much later. But I was watching gay porn with the same results back then, and when I told them, they dropped it. We never lied to each other. It's our pact. So, if one of us says something, no one questions whether they believe what they are saying."

"So, what are you going to tell them now?"

He looked at me

"You already told them?" I was genuinely shocked.

"Do you remember the night I came to your room in the middle of the night?"

"I hope I will never forget it." 

He smiled at me

"That day, you hugged me in the kitchen when I was at my lowest. Ashley told me she was returning the night before, and I was nowhere near getting my head sorted. Then you hugged me, and I knew I meant everything I did. I felt your neck, and I knew I would need much more to be happy again. I admitted to myself that I was probably gay. But I was still confused and worried. So I sent them a message in our group chat." 

"I was a mess, and I needed help. They logged in immediately, Dan made a Zoom call, and everyone but Matt was there. He didn't see the message. Brandon called Matt even though I told him not to bother him. It was a work day, and Matt is a very carrier-driven man. Brandon looked at me. I was messy, unshaven, my eyes probably red from all the crying, and called Matt again with words that Matt would drive over to each of our houses just to kick our butts if we thought he'd prioritize work over this. meaning me, of course." Nate lowered his head slightly, his eyes watery, and a little smile was on his lips.

Then he chuckled. "Brandon told him, when he finally picked up, to get out of his fucking meeting, run to his office, and turn on that Zoom call. The way he spoke really broke me down, and I cried then from being so thankful I have them." 

I felt like crying hearing that. I never had such immense support. It was moving to listen to it, and I was really happy for him.

"Matt logged on just maybe a minute later. He had sent everyone out from the meeting room and took my call just to sit there and watch me cry as my life broke before me." He wiped his eye with his sleeve. "They all wanted to drive the next minute to come, visit, be there for me. We talked for over two hours." 

"They didn't bat an eye when I told them about thinking I am gay. Not even 'I thought so.' Nothing. Just nod, like, 'I hear you. I am here for you. It was all I needed. They listened and then asked how I felt about you and Ashley. They were there for me, and they cared. No judgments, no advice. I am sure they would have given me plenty if I had asked for some, but they mostly wanted to know what I needed, what I wanted, and what I thought. They assured me that they were here for me no matter what. They are the best. I hadn't made a decision then, but it helped me calm down, breathe, and take one step at a time. Steps I can judge and back up if needed." 

"I returned to being able to carry my decisions through without backstabbing myself with regret. In a way, I made peace with what happened and who I am. I was ready to look at myself and be brave enough to learn more about this part of me. Honestly, I wanted to find some safer and better way than to cheat on my wife with her brother, but when I realized being close to you it's so intoxicating, I suppose I made my peace with it." He looked at me with a smile.

We walked silently for a little while, and then he started laughing. When I asked him about it, he told me a story about their escape from home to one concert that went awfully wrong, and his parents had to bail him out for underage drinking and creating quite a mess with his friends. His parents seemed cool or distant, but he didn't mention them much, so I could only guess.

"I have to say, I would have never guessed! I had you for a boring blue collar with no life." I laughed at it now but realized he was not laughing with me.

"I think you're kind of on the point with that." He looked a bit serious now. "I changed a lot, I guess."

"What happened?"

"Let's just say life." He looked at me

It seemed he didn't want to tell me more, and I chose not to pry.

As we were walking and talking, I saw an old hiding spot. It was more uphill, but if I remember correctly, there was a way to it from nearby bushes. And there was a fantastic view.

"Look, I don't know if it will still be there, but up there was a hiding spot. Steve and I used to sneak there. Actually, I lost my virginity there. Do you want to go? It has the best city view."

"Sure, that actually sounds hot."

"I like that you think so. But don't get your pussy ready just yet, boy. I haven't been there in years."

"Well, maybe we will find another and make new memories." He winked at me and as he whispered, lightly grazing my crotch.

"Fuck, you are making me crazy, Nate." I looked ahead, trying to regain composure as he turned me on so much, and I didn't think launching myself on him right now would be appropriate.

He looked around like he was making extra sure no one was in sight and then kissed me so hungrily I could feel his wood in running pants.

"You better know what you're doing now, boy."

"Show me the way, Richard." 

Who the hell is this man?!

I focused seriously on the area we were in, trying to recall the way. I may have walked there dozens of times, but after all those years, it seemed like it was a whole different place with few known spots. I struggled a bit and probably took a way longer route, but in a good couple of minutes, I finally found the spot, at least to the best of my knowledge. I kneeled and looked at the tree before me.

"If I am right, there should be something written here."

Nate seemed intrigued and knelt beside me. I found it. I had to remove a few branches from bushes that weren't here then, but I found it.

"I don't remember precisely what we've written, but I remember we wrote it low, so even if they cut it down, we had a bigger chance to keep it. Seems this area wasn't cut for a long time." I smiled nostalgically.

"We are gay!" Nate read the sign carved deeply into the wood

"Well, it's not the most creative…"

"Feels cathartic." Nate interrupted my self-doubt

I just looked at him, lost for words. If I had to be honest, I got really emotional hearing him say that. Yes, it was. 

I remember that at that time, being up here with Steve was probably the only time I felt like I was truly myself. How could I forget what we wrote here? Well, it was a bit silly, but we were young, and neither of us could say it to anyone else than to each other back then.

Nate hadn't broken the silence. He just took my hand. He didn't need to do anything else. Just being present was everything I wanted right now as I thought back to those times. How different have I been?

I wanted to come here and have sex with him, but suddenly the whole situation changed tone with that one sentence for me. I felt like I wanted to be known by this man, bitterly remembering that this was not even summer romance. This is just a weekend thing that will be destroyed Monday morning. How pathetic of me. I broke the spell myself in the end.

I stood up. Taking Nate up by hand. "Well, it used to be a spectacular view, but it seems most of it is overgrown now." I pointed in the direction I remembered looking through back then. "Sorry for dragging you all the way up here for nothing."

"I love the view I have."

I looked, realizing he was referring to me.

"What a charmer," I smirked at him.

"I mean it." It took all my willpower not to reply with something like 'Until Monday morning' … fuck I am starting to be bitter.

He must have sensed something was up. He leaned in and kissed me. It suited me instantly. I returned his kiss and embraced him closer.

He trailed his hands beneath my shirt, played with my pecs, scratched them, and moved to my back.

We were grinding on each other, our cocks trying to burst out of our pants. Our kiss became hungrier with each touch. I held Nate's neck and ran my tongue from his lips to his ear, sucking on his earlobe and moving to his neck. I lightly bit it. Nate moaned into my ear, and I wanted to bury myself in him.

His warm hand slipped into my jock and slowly spread my precum over my shaft. He spat in his hand and returned to jack my dick at a slow, mesmerizing tempo. Fuck I liked what this man could do to me.

I pushed Nate back to that now overgrown tree. Pinned one of his hands to the trunk above Nate's head as I pulled his shirt up and licked my way down his chest.

When I was too low for him to reach my shaft, I took both his hands, pinned them behind his lower back with one hand, lowered his pants to ankles, and fished out his shaking and leaking dick with the other.

I looked at him like that, shirt raised above his firm pecs, nipples hard and goosebumps all over his chest, hands behind his back, pants on his ankles, and hard dick twitching with anticipation. But most of all – he had a crazed, hungry look in his dazed green eyes, and his lips were red and swollen, parted as if ready for eating cock.

I didn't know how he'd react, but this was too perfect to be forgotten in a mass of random memories.

"Do you trust me, Nathaniel?" I asked in a deep and horny voice but with a touch of care for him.

"Yes, Richard." He said, closing his eyes in pleasure as I licked his leaking dick.

I took a step back, took the phone out of my pocket, and set the camera.

"Look at me, Nathaniel."

As he opened his lusty eyes, I pressed the screen to capture it just before his face crumbled in worry.

"Why did you take a picture of me, Richard?"

"I want to remember this. You look so fucking hot right now. Waiting like a beautiful, muscular slut for me. I needed it."

"Just don't misplace it somewhere." He looked sternly at me, but his eyes softened as I kissed him again.

"I had this idea so many times. I wish I could have a picture like that of you." He said in a husky whisper

"Next time, take one or more. We can make a video if you are up for it." I replied

"Fuck me, Richard."

I kissed him again, reaching one hand to grab his wrists and a second pressed into his mouth deep.

"Lick it, boy, you will need it moist," I growled into his ear as I was humping his raw cock with mine.

And he did lick it well. If that were my cock I would be shooting so hard I would see stars.

"You like this, boy, do you?" I said as I was putting two fingers into his pussy and fingering it slowly

"You love being my little bitch pushed against the tree like this. Fucked raw and hard." I increased the rhythm and added the third finger.

"Tell me slut."

"Yes, I fucking love it, sir."

"This what makes you hard? Being used by a man? Having that pussy ravished? How hungry is she? Fuck, how tight!"

"Take it, sir. Please."

"On your knees bitch, show me how much you need it." He slid fast on that rough dirt and sticks beneath him, pants around his ankles, holding to my legs for support, and lustily sucked my cock, licking it from below.

"What a fucking good cocksucker you are. My overachiever. Suck it good." I started with slow trust in his throat. 

"That's it, good boy. Take it, good."

He was really killing it. The suction he started as he put his arms behind his back without asking was getting me into override. I started fucking his throat hard and had to stop myself from blasting.

"Stand up, boy, show me that pussy. It needs to be filled."

I helped him up and turned his chest to the tree trunk, and his bubble-muscled ass was looking at me with need. Fuck how much I needed to fuck him now. I was so frustrated and angry at how fucked up our situation was that I felt the need for redemption. I originally wanted to make love to him here. Nothing would be more perfect. But realizing he is a borrowed goods made me bitter about it. I wanted this man badly. I wanted all of him for as long we would make it, not for as long my fucking homophobic sister is not at home!

I spread his cheeks, admiring that beautiful pussy as I watched my swollen spit-soaked cock trust in. I pushed continuously in slow but steady motion, doing everything in my power not to savagely rape him here and now. He moaned and pressed against my pole, trusting in small movements.

I filled him to the base and stood still, breathing into his neck from behind.

With one hand, I took his wrists resting on his lower back and slowly but forcefully pinned him to the tree. My second hand took his jaw and turned him towards me.

"Neck or hair, boy?" His tight hot asshole twitched around my cock as I said this.

"Hair, sir."

Without a word, I spat into my hand and applied more to my cock and his hole. Then I took the hair on his nape and pulled it tightly.

"Can you take it, boy?"

"Yes, sir."

I slowly started moving. "If it is too much, you say Red. If you need to stop completely, say Stop."

"Yes, sir."

I don't think either of us fully knew what he had just signed up for. With those last two words, I laid every bit of my maddening anger on him. I fucking revenge fucked him, and I fucked him hard. The sheer violence should have scared him, but he seemed like he was just now getting what he needed all this time.

Neither of us had said a word. All we heard were growls, grunts, muffled screaming, moaning, and silent swearing. And above all, this noise was rapidly pounding into that poor, hungry asshole trusting back on me for more.

I never hatefucked before, but I needed it now, and fuck, he seemed like he needed it too. At one point, his whole body started jerking violently, and he screamed into the woods around us as he shot his load all over the tree I carved my first confession on all those years ago. I fucking loved it. I fucking lost it. I pounded that tight, twitching asshole for the next moments as he milked me, took it, spent, leaning, and repeatedly pushed harshly into the trunk and its hard and rough bark.

I finally felt my balls reaching that limit, and shivers ran all over my body as I screamed into his neck, breeding him hard. Shattered to pieces, darkness all around me and shaking. For hours it seemed I was falling into nothingness.

I came to, surprised I was still standing, and leaned over Nate's firm back, holding him around his neck for support. I do not even remember moving that hand. I stepped back, taking my dick out and watching in awe like his hole was gaping, filled with my cum. 

"That's fucking hot," I said under my breath.

I put my dick in my pants and jock. He was still standing or, better say, leaning against the tree.

"Nathaniel? Are you alright?" I took his hands from his lower back and turned him to me.

He looked like he was crying.

"Nathaniel, have I hurt you?" I said with genuine fear, taking his head into my hands.

He shook his head in negative. Still silent.

"Are you sure?" I looked into his eyes, seriously worried

He nodded and tried a weak smile.

"Do you just need some time?"

He nodded once slowly. His eyes seemed thankful.

I nodded also and pulled down his shirt. He had scratches all over his chest, but thankfully no blood.

"Stay," I said and raised his briefs and pants, dressing him.

Then I took him into my arms and sat with him there on the ground.

We sat there for a long time, silent, without moving, just occasional caresses or soft kisses.

I don't know about him, but I was starting to get thirsty after a while. Truthfully, we went initially just for a morning run, and even though I drank one bottle before, I haven't drunk or eaten anything since. And Nate, neither. I, however, didn't want to rush him and decided to wait for him to speak.

He finally looked up at me and kissed me, smiling.

"Better?"

"Yes, thank you," he said silently

"Was this because of the sex?"

"I loved it, Richard. Really."

"You could have stopped me."

"I would have. I wanted it."

I kissed his forehead. "In that case, you really scared me there."

"Sorry." He said with a tender smile."

There was so much I wanted to know, but at the same time, I wondered if getting even more attached was a good idea, given that we have an expiration date. I sighed. This fucking regret is becoming an annoying theme. I promised myself no regrets and no thinking about such shit for the rest of the weekend. If I burn Monday, please, my stupid conscience, let me enjoy the ride!

"I am starving."

"Me too. Let's go home."

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>> 11. Chapter – Saturdays Pet play

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Hi

This story is part of a larger collection of stories set in the same city, at the same time, happening to a group of friends and acquaintances.

Each story is a standalone storyline, but some side characters may have their own story either in this project or my other.

Feel free to check out my profile or Patreon page for more content.

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