Under the guise of wishing to carpool I road with my boss, Kyle, as we made our way to the district conference that no one in the company wanted to go to but was mandatory all the same. At first it was just like any other road trip, I toggled through playlists on my phone to find one that we both would like. We talked a little and stopped at a convenience store to get snacks. But when we hit the longest stretch of highway Kyle turned down the music and told me to take my dick out.
I obeyed him, like I always eagerly and willingly do. I used the button on the side of my seat to push my chair back so he could better see me.
"Stroke it until it's hard."
I did as I was told, looking over ever so often to see if Kyle was looking. He wasn't, he kept his eyes on the road. Somehow seeing him seem so uncaring about what I was doing turned me on more. Like he was just testing my loyalty and I was happy to perform.
"Tell me when you're leaking," finally he glanced over, "the messy way you do when you're really hard up. Constantly dripping like a broken faucet. Let me know when your fingers get wet."
I groaned. We hadn't been doing this for long, a few weeks or so, but it was the best sex of my life. My tiny supervisor with his filthy mouth and dominate personality made my decidedly larger body go weak for him. He knew just how to pound me, suck me, spank me, lick me. All of it. And it was so so good.
When I was oozing precum I breathlessly let him know and I saw his small smirk before he said, "Now, stop touching it and play with your tits. I want you to keep yourself hard with just your perky nipples alone."
I let out a whine without meaning too.
"What's wrong?" Another glance from him. God he was gorgeous.
"It doesn't feel the same when I do it to myself."
"I know. Now keep yourself hard."
I nodded then reached up and started to tweak my nipples. They grew hard instantly, lewdly pressing against my button up. I used to be a little insecure about them. They are thick and kinda long, but watching Kyle worship them gave me a better appreciation for them. I liked to tease him when we were apart. Late at night I'd send him a picture of my tits being played with. One night it was my kitchen tongs, another they were wrapped with string, another still and I was rubbing them with ice. It never failed to get him to call me, either video or audio, and use his voice to get me off. He always came too, saying my voice and "sexy nipples" were too enticing.
I don't know how long I flicked and squeezed my tits, but I was able to stay hard while he drove. He would sing along to songs and talk about work all while I'm dripping precum onto his leather seat and fondling my muscular chest. His nonchalance really was a turn on.
After about 30 minutes he said, "Cover up, I'm gonna pull into a rest stop, I need to piss real bad."
I tucked my penis as best I could and was glad I hadn't unbuttoned my shirt because we were at the rest stop sooner than I thought we'd be. After doing our business we were on the road again. This time he had me suck him off as he drove, he never got close to coming but he did say I was 'such a good cock warmer' and I swooned at the praise.
It was evening by the time we made it to the hotel. We both looked ourselves over, being sure we didn't look like we had engaged in sexual activities on the road in case we ran into our coworkers. We gathered our bags and checked in. Once the bellhop took our luggage we went to the nearest elevator. Our room was on the 28
th
floor and Kyle took advantage of that time to tease me immediately after the door shut.
He walked up to me with a soft smile. He placed his hands flat on my chest and looked up at me, "You said it didn't feel as good when you touched them huh?" He grinned wider when I shook my head, "Maybe I should do something about that," then he dragged his fingers down my pecs until he reached my nipples and he pinched them both.
They instantly hardened and I let out a soft gasp. He pulled them gently then rolled them under the pads of his thumbs. Shocks of pleasure raced through my body as he continued to play with them.
"You look so hot right now," he leaned forward and slipped his lips around my left tip.
He began to suck at my nipple. Long draws like he thought it would feed him. I could feel his tongue lapping at the underside every now and then and I couldn't help my moans. I could feel each pull of his mouth, my nipple elongating with each suck. I was trembling, my hands flat against the wall behind me as I fought to stay still.
Suddenly the car began to slow and he pulled off quickly and gave me an inquisitive look. We both glanced at the numbers and realized we had only made it to floor 10. Someone had pushed the button and we had missed it. He moved to lean against the wall perpendicular to me and the expression on his face looked the way that I felt. We both hoped that whoever came through that door was not a coworker.
The door opened and thankfully a stranger stepped in wearing red pajama pants and nothing else. He gave me an openly appreciative look, lingering at my chest. He was handsome so I didn't mind the attention, but I wondered what Kyle thought of it. As I went to glance at him the man spoke.
"Y'all here for that conference?"
Kyle answered, "Yes."
"Me too," he nodded like he was thinking, "my third fucking year. I never learn anything new, they are like five years behind the market. All their ideas are stale."
"It's my first year," I offered up, trying to be polite and calm my nerves. We had been so close to being caught.
The handsome man looked at me and gave me a smirk. I didn't know what that meant so I didn't engage, but I watched as he took in my form once more.
