My Manager and I

My manager and I arrived at the hotel a little after seven after spending most of the day on a plane to visit a client. It was just a single day's visit as we'd be flying back right after our meeting ended the next afternoon. A little tired and hungry, we agreed to meet in the hotel bar for dinner and drinks after freshening up in our respective rooms. We ended up having adjoining rooms with those doors in between them.

We got a table in the bar and ordered our dinner. I ordered a beer, and she ordered wine. I had worked with and for her for a number of years, so we were very comfortable with each other, personally and professionally. She took care of the client relationship, while I dealt with the technical tasks and issues. We'd become genuine friends over the years as well.

We spoke a little about the client meetings we had the next day but eventually branched off to other topics since we were already prepared. When we reached a pause in our conversation, she asked how come I had never married. (She was married with children.)

"I just enjoy my solitude and am not looking to have someone living in the same house as me all the time."

"Don't you ever miss, um... 'female companionship'?"

"I don't lack for that."

"But you've never mentioned a girlfriend."

"I didn't say I've had girlfriends. I said female companionship. A girlfriend wants to move in with me or get married. So, I choose companions who aren't looking to settle down with me."

"How do you do that?"

"It helps if they're already in a relationship. If she has someone else in her life, she doesn't start thinking about working her way into mine. It also makes it easier when the relationship has run its course; she can just go back home to her boyfriend or husband without a huge sense of loss."

"So, even married women? Does that cause you any guilt?"

"It's not my job to police their relationships. If they feel they need a little more than they're getting, that's their decision. I'm not forcing any of them to sleep with me. It's completely their choice."

"Are you 'seeing' someone right now?"

"I've got three women I'm currently hooking up with."

"Three?"

"Well, it's best to have more than one at any given time. These sorts of relationships tend to fizzle out over time, so if I have a few going on at once, I can avoid having a gap where I'm not seeing anyone."

"Where do you meet these women?"

"A variety of places. The gym, the bus, community groups I'm involved without in public, work."

"Work?"

I nodded.

"Coworkers or clients?"

"Yes."

"Anyone I know?"

"Yes."

"Who?"

I shook my head. "Part of the implicit deal is that neither of us talk about it. I'm not trying to blow up any relationships."

We had been leaning closer to each other during this conversation, and I noticed her starting to breathe a little heavier. I had always found her attractive, so, even though it probably wasn't the smartest decision, I decided to see where I could take this.

Seeing that she was not turned off yet, I leaned even closer to her, put my hand on her knee and whispered to her. "The women I see know they can experience the pleasure they're looking for without risking their relationship. Their boyfriend or husband will never know that they're getting something they're lacking at home."

She looked me in the eye and said, "It's getting late. I should probably be getting to bed." I could tell she wasn't talking about sleeping at that point, so naturally I agreed.

After stepping into the elevator, we were the only two in there, so we quickly wrapped our arms around each other and started making out. Suddenly, the elevator dinged and slowed, signaling that we were stopping at a floor other than ours. She quickly pulled away from looking flustered and guilty as someone stepped into the elevator with us.

Damn it.

When the elevator reached our floor, we stepped off and walked towards our rooms. When we reached her room, I went in for a kiss, trying to recapture the mood. She put her arm out to stop me and said, "I almost made a mistake tonight. I'll see you in the morning."

Not ready to give up yet, I told her I'd leave the adjoining door on my side unlocked in case she changed her mind. She shook her head and went into her room.

I sighed and went to mine. At that point, I gave up, got ready for bed and was about to get into bed when I decided to unlock the door like I said even though I didn't think it would go anywhere. I got into bed and quickly fell asleep after the long day.

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I was startled awake when I felt the mattress move. I felt an arm slide over my body, a hand rub my crotch and then heard my manager's voice whisper, "I decided some mistakes are worth making."

I immediately rolled over, put my hand behind her head and pulled her in for a passionate kiss. As we continued to make out, our hands started roaming around each other's body. She was wearing loose exercise shorts that I quickly pulled off her, then started rubbing her pussy through her panties. We then took off each other's T-shirts, leaving me in just my boxers and her in her bra and panties.

She took her bra off and I slid down to start kissing those breasts I had admired so often, not too large, but perfect for her slender frame. After focusing on her breasts for a while, I started kissing down her stomach. When I reached her panties, I pulled them off her as she raised her hips to help me. I kissed around her inner thighs for a bit before focusing on her pussy. I was careful to get her wet while making sure to hold off her orgasm. I wanted her excited, but still wanting more. Climaxing could bring her a moment of clarity that might give her a chance to rethink things before I finished.

I kissed my way back up her body. We made out for a while longer with my dick rubbing against her the outside of her pussy.

She reached down and directed me into her. We sighed and I slowly worked deeper into her. I continued thrusting forcefully in a steady pace. After a few minutes, she told me she was about to cum, and I told her the same. She said she was on the pill so I could finish inside her, which was music to my ears. When her pussy began spasming, it triggered my own orgasm, so we came together. We kissed again briefly before heading to the bathroom to clean up. After that, we headed back to bed where we quickly fell asleep while spooning.

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I woke up with the sun later that morning as I usually do. I carefully slipped out of bed doing my best not to disturb her. I crept into the bathroom and closed the door before turning on the light. I used the toilet before washing my face in the sink. While doing that, I heard the door open, my manager walked in, reached around me and started stroking my dick.

I turned around and began kissing her. She wrapped her arms around my neck as we continued to make out. I picked her up, lifted her on to the bathroom counter and slipped in between her legs. I rubbed her pussy with my fingers until she was wet again while she was stroking me to get me hard.

Once I was hard enough, I slipped inside her and began thrusting. She wrapped her legs around me, cinching her ankles together. We went on like this for a while until I told her I was about to cum again. She pulled me in tight, and I exploded into her for the second time in about six hours.

I pulled out of her as she grabbed a towel off the rack and put it under her pussy to catch any droppings. She said she was heading back to her room to shower, since showering together would distract us enough to make us late for meeting our clients. We agreed to meet at the car in an hour.

The meetings with the clients went well and we flew back home that night. Following the rule of discretion, we didn't discuss what has happened between us while in public. We parted at the airport as we each took a different Uber ride back to our respective houses.

In our next one-on-one at work, we agreed that it would be safest to never hook up when we were home. On future road trips, though, we would often joke about how much of our company's money we were wasting by never using both rooms they were booking for us.