My Favorite Boss

I woke up the next morning and brought my fingers to my lips. They were still tingling from the night before, when I kissed my boss Carson for the first time. I ran my hand along my jawline and remembered his soft and scratchy beard against my face and remembered his rugged hands pulling my body against his. I had to get up -- I was getting too excited before work.

Carson didn't come in until noon that day. The office was quiet without him, and I got good at finishing my work quickly, so this was the summer I not only dated my boss, but also became a crossword master. I completed two whole crossword books that summer.

When Carson came in, it was business as usual. We kept it professional the entire day, until we stepped outside the office to lock up. "I had a great time last night," Carson said with a genuine smile.

"Me too," I said. "You're not a bad date."

"Yeah?" he said, laughing. He put his hands on my hips and pulled me in to a kiss.

"You're not bad yourself."

"Yeah?" I replied, smiling myself, as we kissed again.

"Let me take you out on Saturday," Carson said. "There's a fair in town for the summer, we should go and check it out."

"Sounds fun," I said. "I've always wanted to die in a rickety carnival ride."

"Well, let's make that come true. I'll pick you up at 7 on Saturday?"

"Sounds fun," I said. I was excited that Carson was planning fun dates for us. He was a bit of a romantic like that.

"See you then," Carson said, and he kissed me once more. As he held me, my knees shivered as he moved his hands around my lower back and my waist. For a moment, I thought we were going to hook up, right there outside his office. "Fuck, you're too sexy, but I have to go!" He said and left. I wished he could have stayed.

I drove home, face red from how quickly I got heated in our conversations. At work, I could always tell he was being professional. From 9-5, we didn't flirt, and I didn't really think of him as the guy I was dating, but just a coworker. Outside of work hours, though, I couldn't help but get flustered around him. His handsomeness and charisma had me by the hook.

I got home, worked out, and ate dinner. As I got out of the shower that night, I stared at myself in my mirror. Carson was taking me on our third date. I knew the third date was the sex date, and though I was sure Carson would have been fine if I wasn't ready for that step, the truth was I wanted it. I wanted it desperately. I've always found sexual connection with someone to be the highest form of intimacy. I've had people I've trusted with all of my being, like close friends, but there was something about having sex with someone that was a step beyond that honesty. Admittedly, I didn't known Carson that well. We'd only worked together three weeks and been on two dates. But I wanted to have sex with him, not just to sate my youthful horniness, but to be vulnerable and open with him.

I turned sideways and looked at the profile of my ass. As I've said before, I'm lucky to have a bit of a natural bubble butt. I've trained my glutes, sure, with squats and training for football, but I wouldn't say I have just a muscle ass. There's a distinct roundness to my butt. My ass curved out smoothly in a perfect mathematical curve. Future boyfriends of mine have always admired this, and even women have commented on it. While I typically don't like attention, I was flattered whenever someone would compliment my backside.

In the mirror, I scooped my fingers under my asscheeks and pulled them up and let them bounce before flicking them again. As I thought about my own hands being replaced with Carson's, I realized that I wanted to do something new with Carson. I'd never done it before, but I wanted Carson to fuck me. At the time, my greatest fear was that Carson was a strict bottom. That first night in the gas station parking lot, though, as I felt his hands run through my hair, I'd known I wanted him to top me.

I typically don't buy into the whole submissive/dominant kink. While I've since had some hookups where that kind of dynamic can be hot, in my relationships it's never worked. I couldn't describe the feeling. I didn't want Carson to dominate me, but rather just love me. I wanted to feel his body weight on me as he was intimate with my body, and I wanted to feel his warmth assure me that everything was okay. I wanted for him to touch my ass more than anything. I wanted each of my asscheeks in each of his big, rough hands. That was my goal.

I realized that I was incredibly ill prepared to bottom. Dating Danny, I had always topped, but I wasn't oblivious to how he prepped. I had to get stuff to get ready on Friday so I could be prepared on Saturday. I looked up nearby sex shops and planned to go right after work the next day. I forced myself to sleep and not jerk off, wanting to build my excitement for Carson that Saturday.

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All day on Friday I could hardly focus. I'd been thinking about my trip to the sex shop that night. I was nervous. What if I saw someone I knew? I was miles from home and I hardly knew anyone in Charlotte, but it wasn't impossible. I'd be mortified. I tried to look up pictures at the store I had picked out to see where the exact merchandise I needed was, but there were few pictures online. I'd be going in blind. I even packed an outfit so I could find to try to conceal my identity.

At five, Carson had already left the office for the day, so I used the opportunity to change into my disguise. I put on a big hoodie, sweatpants, and a pair of dark sunglasses. The second I stepped outside, I knew that this was not the ideal outfit for the summer in North Carolina, but it would get the job done.

I drove thirty minutes outside the city to a sex shop called "Eros Hideaway." I'd seen billboards for it all along the interstate for years but hadn't visited until that day. It was an unassuming building that was clearly a repurposed Pizza Hut. It had the distinct roof of an old Pizza Hut, but I doubted there was a salad bar inside. The windows were dark tinted, and I could see the faint glow of neon lights inside.

I put my hood up and walked inside. I was afraid the clerk would stop me and ask me if I needed help, but luckily they let me peruse the store on my own. I quickly found two of the things I was looking for -- water based lube and an anal douche. I'd dated Danny long enough to know how to get clean.

The last thing I was looking for was more daunting. I walked to the dildo section and stared. I remembered when Danny told me that he used a dildo to prepare for sex early in our relationship. "Do I not open you up well enough?" I'd asked.

"It's not that, it just helps to loosen things up a bit. It helps me get to a comfortable place faster."

I'd seen what Danny used and was looking for something similar. As I looked, I tried not to wonder how people used some of these things, especially the ridiculously sized things. Finally, I found what I was looking for -- a set of three, small, black butt plugs that increased in size. They had a wide base that connected to a bulbous hook. The packaging read "Beginners P-Spot Butt Plug Kit," and I knew that these would be perfect. "They get me ready really quick," Danny said.

I worked up the nerve to walk up to the counter and put my things down. The man behind the counter was muscular and wearing a mesh, almost see-through black tank top. He had tattoos covering his left arm, and a small gold loop earring on his left ear. "Looks like someone's having a fun night," he said dryly.

I didn't respond, instead giving a nervous chuckle. "You'll want to wash these before you use them," he said, scanning the butt plugs and the douche. "And always make sure you use plenty of this stuff," he said, scanning the lube. "Don't force it. If you need help, look it up online."

I nodded. "Thanks," I said.

"You playing alone with these?" the man asked with a suggestive hint in his voice.

I laughed a little, blushing severely. "Uh, no... well, yes, I'm, uh, preparing with them."

The man understood what I meant. "Well, you have fun then. Don't be afraid to go slow, it should be fun for both of you." He bagged everything up. "That'll be $42.76."

I paid, glad that I'd made my own debit card and my mom wouldn't see my purchases. "Thanks," I said, and started to leave.

"Wait," he said, and pulled out a post-it. He scribbled something down.

"Name's Rick, and here's my number. If you ever need to do more shopping." he said, putting emphasis on the last word. I grabbed it and walked out of there, flustered, creeped out, and a little turned on.

I drove home and opened everything. I washed my toys with dishsoap, as it said to on the instructions, but didn't use them that night. I went for a nighttime run to try to calm myself down, or at least tire myself out. I knew that if I jerked off, I'd feel better, but I kept my promise with myself to save it for Carson. As I laid in bed, I thought of what I'd be doing the next day. My mind didn't go to the sex I might have with Carson, though. Sure, I was excited about that, but even more so I was just excited to spend time with him. I was excited to go to the carnival with him and see him try to win a teddy bear at a stand, or try to slam a mallet down to prove his strength, or eat the biggest corn dog I'd ever seen. I fell asleep, dreaming about what fun I'd have with Carson.

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I slept in that day and was too nervous to eat lunch. I looked outside and saw that it had just been raining. The sky was gray and dark, and I worried that our date would be ruined.

Regardless, I wanted my plumbing to be clear, and while I was regular and knew that Danny never had an issue, I wanted to be extra careful. Instead, I worked out. I was getting really sick of working out in my apartment complex at the time. There was always a mom who talked on the phone the whole time, or a high school kid who had no idea what he was doing with the weights.

Around five, I decided to start preparing. I was afraid it was early, but I'd taken care of my business that day, and wanted to give myself enough time to shower and get ready.

My first time douching took much longer than I thought. It took me a while to figure out how to do it right, but finally got it down after I looked up tips online. I took a quick shower, careful not to get my hair wet as I'd already styled it perfectly for the night, then I laid a towel out on my bathroom floor.

I grabbed the lube and the smallest of the three buttplugs. I'd fingered myself twice before, not for prolonged periods of time. They'd both happened towards the end of a jerk-off session where I was feeling especially horny, but it was no production. In my hand, the toy didn't feel big at all, hardly larger than my thumb. The package read that it was two and a half inches long, so I thought it'd be no problem.

I started with a finger. I put lube on my left middle finger and coated my hole. I had my knees on the towel, my ass in the air, and my chest and face pressed against the floor. I reached my finger back and pressed it against my hole, and it only took a little push to get it in. The man at the sex shop had been right about using plenty of lube. After a couple minutes, I could get my finger down to my knuckle into my hole and could pulse it in and out without pain. Actually, it was quite pleasurable.

I was confident going into the first plug. I put plenty of lube on it, too, and positioned its head against my butthole. I thought that it wouldn't be much worse than my finger, but it proved to be a bigger challenge going in. I had to put my one finger in, and use it to guide it into my hole. I pushed it in, and after a minute of letting my hole loosen for it, it slid in.

After it went in, I drove it a bit deeper, then just laid there for a moment. I was in a bit of pain, but I was also rock hard. My dick was leaking onto the towel beneath me, and I knew I couldn't go too hard with my toy or I'd ruin the night.

My hole got used to it, and I pushed it in all the way. I got to the point where I could push it in and pull it out no problem, and it would go back in again easy. I upgraded to the next toy, which was girthier and 3.5 inches. I was again generous with lube, but faced the same resistance that I did with the first toy. It took me a while to push it in my hole, and it felt a bit painful as it pushed my hole open. I was determined, though, and tried to relax my muscles. I finally got it in, and got to the same level of comfort with it, sliding it in and out with ease.

I pulled it out, and was going to move onto the next one when I checked my phone. It was 6:45, and Carson would be here in 15 minutes! I knew I didn't have time to work in the largest one. I got dressed and got my boner to go away, but I was nervous. I hadn't warmed up with the biggest toy, and Carson was longer and wider than that one. It had been much harder to get each of them inside me than I thought. Would I really be okay?

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I waited on the curb. I was wearing a casual t-shirt, a pair of summer linen drawstring shorts, and my moccasins. Carson pulled up in his truck, and I got in. "Hey babe," he said, and kissed me on the cheek. He wore a lavender collared shirt tucked into khaki shorts with a brown belt and some tennis shoes. "You look cute."

"Thanks," I said, "You too. I like your shirt."

"Thank you," he said, and kissed me again. "Let's go to the fair, before it gets too dark!"

We drove about fifteen minutes to the fair, and we were quickly surrounded by colorful lights, sinful smells, and cheerful, loud people. It was an odd, cool summer night, which only rarely comes after a morning rain. The sky was dotted with wispy clouds that caught the sun's rays as it began to set on the horizon. It was a beautiful night, and I was with a beautiful man.

First, we played some games. Carson was determined to win me a prize. "I'll win my boyfriend a prize or I'll go home a loser," he said boldly, winding up a baseball to throw at stacked milk bottles. He totally missed, and I smiled. He called me his boyfriend for the first time. He threw another ball and hit the top bottle down. I stepped in and threw a ball that struck the center of the stack, but one of the outer bottles was still standing.

"These are definitely weighted," I said to Carson. "Let's try a different one."

We played a couple other games with no luck, but Carson was finally victorious on a water shooting game. He had finally won me a prize. It wasn't a bear, but a scratchy, hairy, blue plush gorilla. I loved it.

We rode a ride that raised you high in the air on swings and twirled you around. We'd watched several people go on it before, and the only thing bad that happened was that someone dropped a sandal, so we figured it would be safe enough. We had a blast, and it was funny to see Carson a little scared. He seemed nervous to be that high up, strapped in with nothing but a seatbelt. I held his hand, and he smiled at me.

After that, we got a funnel cake. I insisted that I didn't want anything to eat, but he insisted. It was delicious -- we ate the whole thing like wild animals. We liked it so much that we got another one, this one with chocolate syrup and strawberry sauce. I was starving after not eating all day, and this really hit the spot. "You have a little something on your face," Carson said, laughing. He took a picture of me on his phone and showed me a stripe of chocolate on my face. "Here, let me," he said, and without warning, he licked my face.

"Ew!" I said loudly, laughing as he scurried away from me. I chased him a bit before catching him and pushing him, just to be pulled back in for a kiss. We kissed for a moment, in the middle of the fair, and I didn't care who saw. We laughed.

We asked a young couple to take a picture of us. Looking back, I still have this picture printed out in a frame somewhere in storage. It perfectly captured Carson's grin. It was special because I knew I made him happy.

We finished the night by waiting in line for the Ferris wheel. It was mid-summer, so the sun didn't set until late. "Are you afraid of heights?" I asked Carson.

"No," Carson said bravely.

"Really? You were freaking out a bit on the swing ride," I teased.

"That thing does not feel safe," he said in defense.

"It's okay, everyone has dumb fears."

"What's yours?" he asked.

I blushed a bit, embarrassed. "Cats."

"Cats?" he said, laughing. "Like, a house cat?"

"They just freak me out. I always feel like cats follow me around. They stare funny."

"Stare funny?" he said, laughing loudly. "It's a cat!"

"They just freak me out a little! God, screw you, I didn't roast you for being afraid of heights," I said.

"I know, I know," he said, laughing. "You get more and more interesting the more I learn about you. I like it." I shrugged and smiled.

We finally got on the Ferris wheel, which took you around three times. As we got to the top, we stared out at the flat horizon. Over the treeline we stared into the dusk sky, and I rested my head on his shoulder. He wrapped his arm around me and leaned into me, too, and we rode in silence for a moment. Up high, the sounds of the carnival were muted, and we were able to enjoy the space around us in peace for a moment.

As we went down, Carson tilted my head and pulled me into a kiss. We kissed as we went around, and as we started to go back up, his hand started to move on my chest, and I touched him too. As we rounded the top for the second time, he stopped kissing me, but kept his hands on me. Our faces were close, the tips of our noses touching, as we stared into each others eyes in the dim night.

"I want you to come home with me tonight," he whispered, only loud enough to barely reach my ears.

"Yes..." I breathed softly, and he once again kissed me. His hand wandered to my legs, and he rubbed my chest and thighs. I let my hand explore the inside of his legs, up towards his crotch. As we circled down to the bottom, we separated and tried to act normal, so the people on the ground wouldn't be staring at us, but as soon as we got high enough again we resumed our making out. We couldn't keep our hands to each other. I tried to crawl over onto his lap, but the entire carriage shook as I moved. I sat back down, and we enjoyed each other.

It was late, and the crowds were thinning at the fair. We headed towards the truck, an excited tension between us. The fifteen minute car ride to Carson's house was torture, as we made small talk to keep us from pulling off to the side of the road and satisfying our carnal urges right there.

We finally pulled into Carson's driveway, and although it was dark, Carson's house looked beautiful. It was in a nice, expensive neighborhood, which I could have guessed based on his business's success.

We went in through the garage, and we quickly walked through his house as he led me to his bedroom. "I had a great time tonight," he said sweetly.

"Me too," I said, almost bursting with anticipation.

"So, do you, uh, want to watch a movie, or..." Carson said, clearly wanting to be polite.

"How about we just do this?" I said, and leaned in to kiss him. He gave in completely, and we quickly got back to what we started on the Ferris wheel.

I pulled his shirt up, using my hands to explore his hairy chest and his muscular back. He pulled his shirt off over his head and helped me out of mine. We pressed our bare chests against each other, my dark body hair brushing against his brown fur. We squeezed each other's pecs, and he ran his fingers down my abs as I petted his strong, hard-as-steel belly. I fiddled with his belt, which he helped me undo, then he dropped his pants, and I rubbed his dick through his navy briefs. I felt him growing each time my hand passed over his package.