Fiance of My Ex Boss

By I Dusk

Published on Jul 18, 2023

Gay

Hello dear readers.

This story is fiction, created for entertainment only, and I kindly ask

you not to repost this story without my permission.

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Hello, my lovely readers. I apologize for the delay.

Unfortunately, I was quite ill these past couple of days and

barely managed to write chapters. I will continue with

posting now.

Chapter 17 - Those firsts of mine

We spent the rest of the day in bed. We ate pizza, talked, and messed around. It was fun!

.

The day slowly ended, and we lay in my bed. Kyle was playing with my chest hair and kissing me. He looked at me with a wide smile as if something hilarious just came to his mind. "How was your first time?"

Right... So we are doing this now? "In general, or when someone topped me?"

Kyle took a little while thinking and rested his chin on my pec. "Both."

I smiled. "Well, the first time, I was sixteen." I caressed his head and reached for his knee, pulling it higher. Then with the second hand, I reached for his spread cheeks. "I was a big jock in a leather jacket, and he was this straight, tall, lean biker. He was eighteen at the time. Brown hair and green eyes. Our parents knew each other, and we went on these long-ass road trips every summer."

Kyle moved his leg and grazed my dick slightly. I smirked at him and held that knee.

.

"How it happened?"

"I liked him pretty much since I was fourteen, so I was always looking forward to summer because of that. He smelled of leather. At night we were mostly camping around the country. When I was fifteen, I pretty much demanded to be in the tent with him. He agreed, and our parents understood since we were not kids anymore, so sleeping in tents with our parents was uncomfortable for everyone."

Kyle smiled, and his fingers started playing with my ear.

"So that next year, we took one more tent. It was fun; we were fooling around and laughing pretty much every night. But never did something sexual. Sometimes at night, he went to take a leak only in his jeans and that jacket on his bare chest. I loved the way he looked dressed like that. One night he didn't come back for a while, so I dressed the same way and went looking for him. I found him behind one bush with a view of the lake. And I sat next to him. We talked for a while, and then he laughed at something I said, looked me in the eyes, and kissed me."

Kyle raised his head in interest. "You topped him, or was he the special one?"

"You see, my dad is 6'5, and since I can remember, we went to the gym, wore leather jackets, and drove bikes. That was pretty much my childhood. So at sixteen, I was already a little higher than him and about 20 pounds heavier with broad muscles. He was in no way small, but even though he was older, I was bigger. He liked that."

.

Kyle smirked and checked me out. "I can believe that. It sounds hot. Do you still wear them?"

"Leather jackets?"

Kyle nodded.

I laughed. "When I am back home, it's more like dress code."

"I want to see you in leather sometime!" his eyes glistened. He was so cute right now that I had to smirk.

"If you want, we can fuck in leather jackets. I love the smell of leather and how it feels on bare skin."

His eyes narrowed, and they looked somewhat dim. "Deal."

"Do you have one?" I asked. Damn, this guy will look hot in it!

"Leather jacket?"

I nodded playfully, caressing the curve of his butt.

"No, but I will probably buy one."

"Go for it. I think that will be hot!" I felt my dick filling. I liked where this was going. With the image of Kyle in leather, I was seriously starting to think about taking him now and not waiting till tomorrow. We can fuck all night and sleep in the morning!

.

"You can take me on a bike sometime."

"Can you take some time off Karl in the summer? I will take you on the trip, and we can fuck around the country." I started kissing his neck and trailed his firm pecs. He moaned sweetly and scratched my chest.

"Karl goes himself somewhere like that in the summer. Don is also a biker," he laughed, realizing that. "I love that idea!"

"True." That reminded me that I didn't mention that Don knows about us. I should.

.

"So did he top you or you him?" Kyle licked my nipple and bit it lightly. I purred and grinned. I will tell him tomorrow.

"I topped him." I licked his ear.

"He wasn't straight then," Kyle stated confidently.

"Well, I suppose he was curious; he had a girlfriend back home, and last I heard about him, he was married to a woman, but who knows." I shrugged. Not like I cared about labels that much.

"Yeah, I would just assume he'd let you suck him off or fuck you. Not let you fuck him."

"Man, do you want to hear it, or do you have some questionnaire I just need to fill out?" I smirked at him playfully.

"Sorry, continue," he grinned. Fuck he's cute!

"Let's just say I was that hot, and I was never a timid person," I winked at him. "We have been eating each other out every night since then. At some point, I wanted to try sucking him off, and then I didn't stop at that. He was already naked except for that leather jacket, and when I saw him completely delirious, I started to rim him. I knew I wanted to fuck him since the year prior, and this just worked out perfectly. He loved that. The next night I added fingers, and on the third, I got to fuck him. It was, as many first times are, a bit awkward at points, but we were both too horny to care much about it then. We were already on the way back then, so we slept after that together only twice before we returned home, and he went to college. It was one of those rememberable summer romances." I smiled. "We kept meeting over the summers for the next few years, he always had some girl back then, and we loved the thrill of hiding. I suppose there started my obsession with straight-taken guys."

.

"Was he a virgin?"

"He has slept with a few girls before me, but he never had someone play with his ass. He said he didn't even consider himself gay."

"Then how did you do it?"

"I can be very charming," I winked at him.

"That you can." Kyle grinned. "Did you meet him after that?"

"We kept meeting over the summers for the next few years, he always had some girl back then, and we loved the thrill of hiding. I suppose there started my obsession with straight-taken guys." I chuckled. "We actually fucked a couple of years ago, but by that point, he was married."

Kyle rolled his eyes. "Shocker!"

.

"Did you tell your parents?"

"That I fucked straight son of their friends?" I laughed. "Not specifically. I mean, both my parents are really cool. Until guys in locker rooms started talking only about pussy, I thought everyone liked both. When I told my parents I liked some guy, they didn't have any other reaction, as you would expect if I told them I liked girls. So I assumed it was the norm. Since they were straight, I thought I might have stages or something like that. Like, for now, I like guys, and maybe I will like girls later in life. Who knows... But as I grew older and spoke more to friends about this kind of stuff, I realized that I will probably never care much about girls as I do about guys."

"Damn! That's amazing! I can't imagine my father or anyone I know would take it so well."

I shrugged, "My dad is great, he's got a few quirks, but I love him. Mom is just an angel. Those two are striking opposites, but they fit so well together it's beautiful."

"That's nice. So you were open from the start?"

"Pretty much. I was big, so no one dared to bully me for that, and confident enough to be myself without the need to broadcast it. Who knew me knew, and if someone assumed I was straight, I didn't care."

"Damn..." he looked dreamy.

."What? Did I ruin your image of me as a troubled boy with issues you could save?"

Kyle frowned. "No, why?"

"Nothing. I just remembered when you looked at me like I was a lost puppy back then."

"Yeah, you told me you'd bite me," Kyle grinned smugly.

"I still can." I bit his nose playfully and pounced on his lips while grabbing his ass and caressing his crack.

.

"So, how it happened with the special one?"

"How do you know he was the first?"

"Wasn't he?"

I chuckled. "Yeah, he was." I reached for his lips and traveled along their length. I was getting hungry for him.

"Well..." I reached for the lube and smeared some on my fingers. "I was in college, and this cute tall kid entered my dorm room." I circled his crack and slowly massaged it.

"Right..." Kyle spread his legs wider and watched me with a lusty smile.

"He had this longish brown hair and one of those sad blue-gray eyes. I was set on taking him one day. Especially when I later found out he is gay. But he always just glossed over my efforts with a laugh."

.

I slowly entered Kyle's hole with one finger, and he hissed softly. I kissed him and turned the finger inside him, making him moan.

"At first, I told myself it's okay since I don't do openly gay guys anyway, and we became buddies. I even started training him, and he nicely bulked up over time."

"What did you train?" Kyle watched my eyes and lips and moaned softly as I gently fingered his hole and grazed his button.

"Box, some weight training, cardio, usual stuff one trains at the gym. We found one small not far away, which was usually empty at times that suited us."

.

"About a year later, one night, we returned to our dorm room from one party, and we kept talking about how we like sex. He told me about his ex and some fuck buddies he had, and I told him about some of mine. We got into a heated discussion about how we fuck, since we both topped our bitches. He was pretty built by then."

"Uh-uh... more..." Kyle sighed and spread his legs wider. I added a second finger. He kissed me and put his arms around my neck.

"What happened then?"

"I don't know who kissed who, but we started making out heavily, and by that point, I already had a huge crush on that boy. He was fierce! He bit my lip and nearly ripped my shirt off when he started undressing me, and he gave me a really good head. At first, I thought we would just suck each other off, but he wouldn't have that, and I am not someone who refuses a challenge."

I added a third finger to Kyle's pussy and slightly increased the rhythm of fingering him. He groaned.

"Did it hurt?" he asked, and slight fear crossed him.

Like a bitch! It was pretty much the reason why I decided to top after that mainly... I kissed his nose and smiled gently.

"Yes. I was a virgin, and we were young and rough. We both played the tough top jocks to the very end. I suppose neither of us wanted to seem like we had emotions or were looking for more than just hunting our prey and fuck him. But I enjoyed it a lot in the end. We fucked the whole night."

.

Kyle looked at me thoughtfully. "You loved him, did you?"

"I think few of us loved him at some point. He was that kind of distant guy with an edge and issues he wouldn't tell anyone about. We were like his big brothers trying to save him when he refused to be saved, and the more he played the tough guy, the more we could see he was just a scared little kid, and we wanted to be the ones to shield him against the world."

Kyle looked at me, and he seemed moved by it. "Did you in the end?"

"No... I came late." I shrugged.

"How's that?"

"Kyle, I am trying to fuck you now. I don't want to shed my soul here."

"Why not?" he looked at me so earnestly.

I sighed, pulled out the fingers, and sat. I wasn't even angry that it ruined the mood. In a way, I was grateful he cared, but this took a whole different turn than I intended...

.

I kissed him. "Fine." I combed through his hair and kissed his nose. So, I have a boyfriend. How hilarious.

"He and this girl met in one class, Cor. She was the one who found the gym, actually, and they trained there, but since I knew about that stuff more than any of them, they asked me to join. Since Rick was asking, I didn't want to refuse," I leaned over the backrest, and Kyle sat next to me with his torso turned toward me.

"At that time, this guy Ben started working there as well. He was this huge mountain. Black guy with a menacing stare. If I should ever pick a single person I wouldn't ever want to fight, it would be this one. And it was obvious that he liked Rick as well. So every time we came there, Ben came over. At one point, we were in this weird triangle where it was obvious to all of us what was happening, but Rick just laughed at us since neither one of us two was his type, and he wasn't looking for a boyfriend anyway. Too many twinks to fuck, I suppose. So after some time, Ben and I just gave up and enjoyed having him around. And we became friends."

.

"Then he found a boyfriend?"

I laughed sadly. "When he was twenty, his grandfather died. He looked like some huge stone was just lifted off his shoulders, and for a few months, he was a bundle of joy. Carefree and even said that it's the first time he is looking forward to going back home. After summer, he was a bit down but never said anything. But then his birthday came up, and he went home. He had this determined face on him and said he was coming out to his family."

Kyle looked at me intently as if he was expecting what I was about to say.

"When he came back, he was a mess. I mean, an utter mess. He kept crying at night, and no matter what I said, cheered him up or calmed him down. He refused to let any of us in. His parents renounced him."

"Fuck..."

.

One day he called me, but I left my phone in the dorm that day by dumb accident, and I found out only after I came back. By that time, he was nowhere to be found. I called Cor, and she told me she didn't know either. So we started looking for him, and it was evening when we knocked on Ben's door. He was only in shorts and told us Rick was sleeping. I knew from the way he looked that they were together."

"Maybe they just talked."

"This was different. In those times, we were all sexually very open, and Rick had already slept with Ben and me a few times, but it was always just sex. When Ben opened, I could see in his eyes that this was a big deal. Emotionally, I don't know what Rick told him, but Ben was definitely crying at some point, and no matter if they slept together then, something between them shifted."

I felt sad remembering that. I looked away and just continued. "I knew that Rick had finally decided to open up to someone, and when he called Cortney and me, we didn't pick up, so he went to Ben's. I hoped it was just the heat of the moment kind of thing, but they've been dating for nearly three years after that. And during that time, I just accepted being stuck in a friend zone."

.

"Did you ever sleep together afterward?"

"Yeah, sure, a few times. He is the only one before you that I was okay with switching roles." I looked at Kyle with a small smile.

"Why didn't you ask him to date you?"

"I did, but he preferred me as a friend. When he broke up with Ben, they had a few months when they didn't contact each other, and Rick missed him as a friend very much. He told me he doesn't want that to happen again."

"Did you ever get over him?"

"No, but I never cared about doing so, to be honest. It's part of me. In a way, I'm grateful for that cos with the kink I have for taking straight unkeepable guys; This makes me believe I actually can care about someone. However twisted that may sound." I smiled at him weakly.

.

"You really do, do you?"

"What?"

"Care."

"Depends on the person." I looked seriously at him.

"How did you manage to live together after?"

"We didn't. His parents cut him off. And he went to live with Ben in that gym. Worked there for a while even. Tom, another friend of ours, rented a place and needed a roommate, so I went there. Honestly, since then, Rick and I have become a bit more distant. But we are still friends; I hate his boyfriends, though. Every single one he ever had." I laughed, and palm faced, realizing how petty that was of me.

.

Kyle kissed me and brushed my face.

"And what about the second one?"

I chuckled. "That would be Ben."

Kyle's brows shot up. "Ben, that one who dated Rick?"

"Yeah, twice, once in a threesome with Rick and then once in a threesome with his now husband."

"Man... Why?"

"Who knows? First, it was a dumb try for closure, and since Rick topped me, it went naturally. It was fucking hot night, though! We all bottomed and topped each other. One of the best threesomes I have ever had. And after a while, Ben and I clicked, and we are good buddies to this day. And he is a great top. One of best I know."

"Really?"

"Yeah."

"Well, in that case, I hope I will change your mind sometime."

I grinned, not even realizing he could take that personally. He was cute!

"Sure, I would love that." I dove into those welcoming lips.

.

"What time is it?"

"Not sure, wait... nearly midnight."

"Let's sleep, Ross. We will need a lot of strength tomorrow."

"You bet we will, boy," I smirked.

I kissed him, and we both went into the bathroom. I then switched lights everywhere and tucked in next to this man. We kissed for a long time, and then he cuddled beside me, his face pressed against my chest.

"I'm not sure I can fall asleep like this, Kyle," I grinned.

"Try. If you don't just move away after I fall asleep, I want to hear your heartbeat."

I covered my eyes and laughed. For real?

What is weird is that I fell asleep, and I think I never slept so well.

.

.

Chapter 18 - Kyle's first - https://www.patreon.com/posts/fiance-of-my-ex-78675281


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Next: Chapter 18


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