My Favorite Boss

I woke up the next morning around 11 AM, groggy from my restless night. I had the weekends off, but the first thing that came to my thoughts was last night with my boss — sucking each other off in the cover of darkness in the gas station parking lot. For a moment, I wondered if it was a dream, but my body remembered it was all too real.

I grabbed my phone, and just then, my boyfriend, Danny, videochatted me. I turned my light on and quickly sat up. I’d been feeling guilty about cheating on him all night, so I decided I would tell him. “Hey,” I said as I answered the phone.

“Hey cutie,” he said. Bright white daylight surrounded Danny’s cute face. Danny had bleached blond hair and light blue eyes. I loved how his narrow nose scrunched up whenever he was uncomfortable. He had thin lips which matched his thin frame, though he’d recently been working out and had built some muscle definition. “How was your second week at work?”

“Pretty good, actually,” I said. “How’s lifeguarding at the country club?”

“It’s amazing,” he said. “I was thinking how lucky I am to sit out in the sun and enjoy the pool all day, and hardly have to do anything.”

“Don’t brag,” I said, smiling.

“Well, it’s not all great,” he said. “All these divorced dads keep coming up to me and hitting on me…”

“Oh?” I asked. “That’s weird.”

“I guess. I’m the only lifeguard who wears a speedo, and they always use that as a conversation starter.”

“Oh, so they’re just getting to see your cute ass in those little things? Hell, I’d hit on you too.”

“Ugh, I miss you,” he said giggling. He panned his camera up to reveal that he was lying naked in bed. He was lying on his stomach, and wiggled his butt a little, making me hard.

“Ooh, I miss that,” I said. In our relationship, Danny was strictly a bottom. In the bedroom I sometimes wished he was verse, but he was a good lover and we always had fun together.

“Yeah?” Danny said, touching his ass with his free hand. “God, I miss you so badly.”

I pulled out my dick and panned my camera down. “My guy misses you, too,”

I said, stroking it for the camera.

“Fuck, Blake! I hate long distance!” He said, pulling the camera up to his face. “I wish you could be down in Florida with me.”

“Same to you here,” I said. “It sucks.”

“Yeah, it does…” he said. An alarm went off in the background of his room.

“Ugh, I have to go to work. Just wanted to call and say I miss you.”

“I miss you too,” I said. At that moment, I decided not to tell him about my night with Carson. I didn’t want to mess our relationship up, so I made a pledge to not do anything more with Carson. It was more professional, anyway. “Have a good day at work.”

“Thanks. Enjoy your day off!” he said, then he hung up. I took a deep breath, feeling a little guilty that I wasn’t honest with him. To start my day, I decided to go work out.

I hadn’t found a gym yet in town, so I used the gym in my apartment complex. It was small and only really had dumbbells, but I made do. After my workout, I went for a walk to grab lunch.

As I sat at a local deli, I thought back on my night with Carson. My favorite thing about him was his smile. It was warm when I met him, and it was the same smile when I looked up after sucking him off. I liked that he wasn’t some other person when hooking up. It always felt like him: comfortable, kind, and strong. I smiled as I thought about him, and realized I was developing a crush on him. Did he feel the same way about me?

I spent the rest of the weekend trying to focus on why I’d moved to Charlotte in the first place. I was here for work, not for pleasure. I needed to focus on building my career and ignore anything that would get in the way of that.

————————————————————————————————————-

On Monday, I got to work and made the coffee. I was nervous to see Carson again. We hadn’t communicated since that night, so I had no idea where he was in terms of our relationship, professional or personal. I nearly jumped when he came into the office around 1 PM.

“Hey, Blake,” he said warmly. “I have some notes from some job sites I visited today, do you mind typing them up and sending emails to the clients?”

Seeing him again, he had the same inviting smile and kind tone he had before. He seemed to be acting like nothing had happened, that we were business as usual. I followed his lead. “Of course.”

He handed me his notes, and he went over and sat at his computer. The rest of the day, we worked mainly in silence. We made small talk a couple of times, but he put in his headphones and seemed to be listening to music as he worked, so I didn’t bother him.

Finally, 5 o’clock rolled around, and we both stood up to finish for the day.

“Hey, Blake,” Carson said as he got up. “Hang out for a minute after, I have something I need to talk to you about.”

My heart dropped into my stomach, and the few minutes it took me to pack up felt like hours. I knew he was going to mention last Friday, but what would he say? What did I want him to say?

We walked out of the office, and he waited as I locked the door. I followed him to the parking lot, where there was a small bench, where he sat down.

“Have a seat,” he said, inviting me to sit next to him.

I sat next to him and looked at him. I tried to put on a brave face, even though my heart was beating fast. I hadn’t ever felt so nervous about a guy before, but something about Carson made me nervous and excited.

“Look, I wanted to be direct with you, because I’ve learned that’s the best way to do things,” he said, looking at me in the eyes. “I wanted to apologize for what happened the other night between us, because it was unprofessional of me.”

I looked at him. I could tell he was a little nervous as well, but his tone didn’t sound apologetic. “It wasn’t fair to you, either. You’ve done a great job at work, and I don’t want you to think that what happened will change anything. But also you’re a smart, funny, and handsome man, and I’m interested in you as more than a hookup.”

I looked at him, and my heart leapt as he said that last line. “Okay…” I said slowly.

“So, here’s what I wanted to say. I want to take you out this Wednesday, and have a re-do first date. We’ll go get tacos and just talk, get to know each other. But, I know that I’m the boss, and don’t want you to feel uncomfortable. So…” he said, rubbing his hands on his thigh nervously. “Just let me know tomorrow morning.”

I looked at his handsome face and stared into his honest eyes. “If you don’t feel the same, I won’t take it personal. I’m an adult and can move on.”

I looked down for a moment to process. “This is a little formal,” I said lightly, cutting the tension a bit.

He chuckled. “Yeah, I know. I’m normally smoother than this…” he said.

“Okay. I’ll think about it,” I said. “Thank you.”

“No problem,” Carson said. “I’ll see you tomorrow.”

He got up and walked to his truck. My heartbeat blocked out almost all sound around me as I stayed seated and watched him drive away. I couldn’t think straight. Finally, I got in my car and drove home.

When I got home, I knew I had to show up and show responsibility. I video chatted Danny, and luckily, he picked up. “Hey,” he said. “What’s up?”

“Hey,” I said. “I’ve got something to talk to you about, is now a good time?”

“Sure,” he said. I sat down and explained everything to him. I told him about Carson, what happened at the gas station, and what happened at work that day. I apologized for not being honest and got a little emotional as I did so. I cared about Danny. I didn’t know if I loved him, but I didn’t want to hurt him.

Danny sat quietly for a moment after I finished explaining everything. “Thank you for telling me,” he said after what felt like an eternity of silence. “I guess I should tell you something, too. I know I told you about all the guys hitting on me at the country club. Well… last Saturday, after we talked, one of them asked me to come shower in front of him at his house, and I did. We didn’t do anything physical, but he did jerk off to me, and I admit, I was really, really tempted…”

I understood the feeling. “Okay, I understand. I fucked up by actually doing something, though.”

“No, I don’t want to compare that stuff,” Danny said. “Look, we both know we’re sexual people. I mean, damn, we certainly know how horny we could be.” I nodded and smiled. We hooked up almost every day at school, maybe even more.

“Yeah,” I said.

“If I’m being honest, I’m not really interested in an open relationship,” Danny said. “We’ve talked about that, and I know you aren’t, either.”

“Yeah,” I said. After a moment, I said, “Do you want to take a break? Just for the summer? And see where we are when we get back to school?”

“I think that would be great,” Danny said. “We can both have our summer fun, you know, but I don’t want this to be the end for us.”

“Me neither,” I said. I was so relieved he was so understanding. “I don’t want to lose you as a friend this summer, though.”

Danny laughed. “Me neither. Besides, we can share our conquests. I’ll say I’m really intrigued by this whole scenario with your boss now…”

I chuckled. “I know, it’s kind of hot, right?”

“You think you’re going to say yes?”

“I don’t know… I think I just want to see where this goes. I’ll say, it makes me excited.”

“Okay. Then it’s settled,” Danny said. “Let’s take a break. You have fun with your boss, I’ll have fun with the country club guys. But let’s keep in touch. Okay?”

“Okay,” I said. “Thanks for being so cool.”

“You too,” Danny said. “I miss you.”

“I miss you too,” I said. We sat for a moment, in silence, just looking at each other. Danny had been a lot of my firsts — my first time having anal sex, yeah, but my first boyfriend. We got each other Christmas gifts. I booked us a weekend away in a hotel room for Valentines. I stared at his face: he had a handsome, defined chin. His thin lips puffed out at the end just perfectly and looked as if he was always about to say something to you. I stared into his blue eyes, which I saw remember widening and sparkling the first time we kissed, and the first time I slid into him.

“You know, I wasn’t lying when I said I miss your ass, either.”

“Me neither,” he said, smiling.

I moved over to my couch and propped my phone up on a candle, facing me as I took a seat on the couch. I pulled my pants down, and pulled my dick out of my underwear and started stroking it. “There he is,” Danny hissed, and moved into a similar position himself.

I stroked my cock as I watched Danny undress. He pulled his tank top off his lean body, and I admired the new definition in his abs. When we first started dating, Danny was pretty much only thin — but Danny asked me to help him build some muscle, and now I was enjoying the rewards of my training. He turned around and seductively pulled his shorts down a bit, bending over to show the top of his underwear.

“Stop teasing me, man,” I said, stroking hard. I generally didn’t get too much out of porn. It always got the job done, sure, but it didn’t excite me. It met a need. As I watched Danny pull down his pants and stick his ass out in his slutty underwear, though, I salivated. I remember touching him, feeling my hands slip past his elastic waistband and grab his ass as we kissed. He wiggled his ass for the camera, showing off his tight-fitting white bikini briefs, before pulling them down, ass bent over, naked. “Fuck, man,” I whimpered. I took off my shirt and shorts, joining him in the nude.

He spread his legs wide, bent over still, and I watched him stroke his dick from under his legs. His dick was five inches long and narrow. Danny didn’t like me sucking him much, and he never topped. One time, I asked him why he didn’t like having his dick sucked often. He told me he got more pleasure out of other things than getting blown, and I certainly took advantage of what he liked to do.

Danny flipped over to see me better, pulling his legs up on the couch with him and jerking himself like a frog. As he stretched his flexible hips, I grabbed the base of my cock and slapped the palm of my free hand with the head of my cock, making a light slapping sound. “I miss you,” Danny said, stroking himself. I watched as he slid a hand down to caress the inside of his legs and watched as the tips of his fingers began to walk down his taint and towards his asscrack. I imagined my fingers first exploring his ass, timid at first.

I continued to jerk off as I watched himself do the same. I could tell he was letting his fingers massage his hole, poking as the rosebud I’d so often deflowered. With my free hand, I massaged my chest, and twirled one of my nipples slowly between my fingers.

I could hear his soft moans and heavy breath through the phone, and I watched as his pale face turned pink. “I’m gonna cum Blake,” he said quickly, before shooting his spunk onto his chest. His mouth opened wide as he groaned loudly, and I watched his body shake as he let his orgasm take over him.

I couldn’t contain myself, either. “Me too,” I managed to squeak out, as I blew my load all over myself. The first shot of cum almost hit my chin as it erupted from the head of my dick, and I crunched over as much as I could before releasing the tension in my spine and laying back. White splattered covered my chest and down the middle of my abs, as my softening dick dribbled the aftermath onto my thigh.

“Now that’s how you say goodbye,” I said, laughing.

Danny giggled on the other end of the call. “Yeah, it sure as hell was,” he said with a huge grin.

I grabbed my phone and took Danny with me to the bathroom, where I used a towel to clean myself up. “We’ll keep in touch, right?” I asked. “I don’t want this to be the last time we talk.”

“Me neither,” Danny said. “I don’t want this to be the last time we do something like this, either.”

I smirked. “You liked that?”

“Yeah,” he said.

“Well, I don’t want it to be the last time either,” I said. “So we’ll get together back at school. Okay?”

“Okay,” he said, cleaning himself off, too. “Take care, Blake. Have a good rest of your summer.”

“You too,” I said. Danny hung up the phone, and for a moment, I wondered if I’d made a mistake. Danny was so sexy and comfortable to be around. He was so understanding, too; he was cool about my hookup with Carson in a way I don’t know if I would have been. A relationship with Carson was scary: he was older and bigger. More than that, he was experienced. He’d certainly had many lovers beforehand, which meant I had a lot to live up to. Could I meet his expectations of me? I wasn’t sure I was “gay” enough for him. Despite my penchant for cocksucking, I really acted more like a frat guy. Was Carson going to get bored with me?

I went to bed, unsure of what I was going to say the next morning, but I slept well, knowing that Danny would always have a special place in my heart.

————————————————————————————————————-

The next morning, I woke up, still unsure of what I wanted to do. I looked over at my phone to see a good morning text from Danny. “Go get him!” the message read, and I smiled.

I got to work and did my morning routine of making coffee and looking over the schedule for the day. At around 9:30, Carson walked in, wearing a bright red collared shirt and nice dress pants. Looking at him with fresh eyes, he seemed even sexier than I thought. His huge arms filled out his sleeves and his broad chest pulled the tight shirt taught across his breadth. What decided it for me, however, wasn’t his big, white smile that morning.

“I brought us donut holes,” he said, putting the box down on my desk. “I ate all the jelly ones, though.”

I looked up at him. “Thanks,” I said, and popped a powdered donut in my mouth. “Jelly are my least favorite, anyway.”

“No problem,” he said, and went over to his desk.

“Carson,” I said. “I’ll go out with you tomorrow night.”

Carson looked at me with a satisfied smile. “Cool. Let’s keep relationship talk out of the office, but I’ll pick you up at your place at 7 tomorrow night?”

“I’ll text you my address,” I said with a smile. I had a warm feeling in my gut. Carson was new to me in so many ways. He was a man in every sense of the word: large, hairy, loud, rugged, and masculine. I’d watched him on job sites command others’ respect in an instant. I also saw his tender, kind, and responsible side, like when he changed my tire, or with the donuts I was eating that morning. And, that one Friday night, I felt things I hadn’t felt before. I felt relaxed in his hands, knowing he would take care of me and my body in every way he knew how. As I scarfed down another donut hole and sipped my coffee, I texted my family quickly: “I’m really glad I took this job.”

————————————————————————————————————

The day at work Tuesday and Wednesday passed quickly. Carson maintained his professionalism, which I later came to respect. Through my entire time working there, we never so much as kissed in the office. As an adult now, writing this, I can appreciate how this not only kept my professional experience focused, but it also helped steer me away from messy workplace romances.

Finally, after locking up on Wednesday, I ran home to get ready. I tried to get a quick workout in, at least my upper body, to look a bit pumped up for our date. After my workout, I quicky ran upstairs to shower and get dressed. I put on an undershirt and a casual collared shirt, though it was one I’d already worn to work. I wore my classic boxers, a pair of preppy khaki shorts, and my moccasins. By the time I was ready, Carson was there, and while my hair was still a bit wet, I rushed down to meet him in the truck.

When I got down there, he leaned over from the drivers seat to push my door open. He was wearing a sleeveless athletic jersey for the Miami Dolphins and a pair of khaki shorts.

“Am I overdressed?” I asked.

“No, you look perfect,” Carson said with a reassuring smile. My mother always taught me that I should dress up for a first date, but I didn’t mind that Carson hadn’t, especially since I could see the totality of his large muscular arms.

We drove and made small talk, then he pulled up to a cool modern taco shop. We ordered a couple tacos each, and he paid. As we waited for our number to be called, we grabbed a beer. The restaurant was called El Norte, and it had a big gravel yard filled with tables and backyard party games. Overhead a game of horseshoes or cornhole hung beautiful lights that zigzagged over the entire patio. “Have you ever been here before?” Carson asked.

“No,” I said. “I’m just now realizing that I haven’t explored much of Charlotte since moving here. I mostly eat at the same shitty places I have back home.”

“This is a cool, more modern part of town,” Carson explained, “They re-did a lot of this area a few years ago. There’s lots of cool places around here.”

“It looks like it,” I said.

“I’ll show you around to the cool spots,” he said with a smile. “So, do you think you want to stay in Raleigh after you graduate?”

“I’ve thought about it. I love my family, and don’t want to move too far away, but I’ll say I’ve been enjoying this summer living on my own.”

“Did you have a roommate at school?” he asked.

“Yeah, I did, same guy both years. He’s cool, but I’m glad I have a place to myself right now.”

“I remember when I first got my own place, and yeah, it’s fantastic. It made me feel like I was finally my own man, you know?”

“Yeah,” I said. We continued to make small talk for hours. We talked football for a lot of it, which was actually refreshing. Danny didn’t know anything about sports, so to talk to another man on a date about football felt nice. I was a Colts fan because my mom was from Indianapolis, and Carson was a Dolphins fan because he grew up in Jacksonville. We each had a couple beers, but neither of us needed to be too tipsy to enjoy each other’s company. We played cornhole, and he was out of practice, so I got to show him up game after game until he finally conceded. To be fair, I’m an absolute menace at cornhole at a tailgate. I’m the reason that the LGBT club at school made it to the finals of the cornhole bracket including all the frats at North Carolina.