“So, you probably didn’t start to come into yourself until college?” Mr. Callahan asked, leaning forward just slightly.
“Yeah, I still made the grade, but people started to see me as more than just a smart kid. I’m still that guy who waits to be approached at the bar though. I’ll have to improve on that pretty quick, though,” I said.
“Why is that?” Mr. Callahan asked.
“Well, another assistant invited me to join some of the rest of the staff for drinks later this week. I want them to think of me as friendly, outgoing,” I replied.
“Well, you seemed fine speaking to me after the meeting,” he said.
“That’s true, but the way you came to introduce yourself had a lot to do with that. A lot of bosses are standoffish. You were willing to come say hello, a man of the people. Plus you even wanted to meet with me. It’s good you take the time to get to know the staff,” I said.
“Well, I think I intimidate most of the staff, but I am glad you think well of me. First impressions matter to both sides of a meeting,” Mr. Callahan said.
I nodded in agreement. As the conversation began to lag, I excused myself. I could feel his assistant’s eyes on me as I made my way down the hall toward the elevator around the corner.
Chapter 6
Tyler
My conversation with Miles had been pleasant, but still left me wondering whether he preferred men or women. My instincts said that there were a few things about himself he didn’t realize he hadn’t figured out yet in that area. I wanted to teach him.
I felt fond of him overall the more we talked. Just as I had been Claudia’s protégé, business-wise, I felt I could do the same for him. Aside from my personal interest in him, he might prove to be an asset to consider in further discussions with Claudia. Once I was sure he was gone, I decided to speak briefly with Tina.
“He has got to be ten years younger than you, and he is company ink,” she said.
“Yes, but discretion has always been the name of the game. Also, age is only relevant in legal instances, otherwise you limit yourself in life’s buffet,” I replied.
“Well, he was cute. He spoke well in your office. His enthusiasm and positivity is endearing, and newly found self-confidence would be an interesting match for you. You could be catching a butterfly just as it emerges from the cocoon,” Tina said.
She gave me a knowing smile and returned to working on something on her computer. I returned to a few tasks I wanted to complete before leaving the office for the day as well.
Over the next few days I made a few inquiries about where I could bump into the staff for drinks some time and put forth some effort into being the kind and approachable boss that Miles seemed to think I was. Claudia was supportive of being friendlier with the staff, so it was an easy transition to make. After merely suggesting there was some distance between the staff and upper management, she issued memos encouraging us to visit with departments, sit in on meetings, and join the staff for lunch or dinner when they went out from time to time.
Friday night, the chief marketing officer and I joined Miles and company for drinks.
“It’s so cool of you guys to come out with us,” said a drunken girl from advertising.
She had the liquid courage to attempt sleeping her way to a promotion, because the CMO was old, fat, and married. He was clearly uncomfortable.
“I thought this would be more like a quiet sports bar type thing. I’m going to go,” he said, quickly getting up and leaving.
His playmate looked my way. I simply shook my head. She returned to drinking and left a little later. As she left, Miles and the other new assistant, Marjorie, walked in.
“Hey, everybody. This is miles. He’s Chase’s new assistant, floor six,” Marjorie said.
He received hellos and handshakes as they made their way through the group. I continued to sip on the Old Fashioned I had ordered. I listened as they talked about their days and told Miles things to look out for, or forward to, about the company. I could tell some things were somewhat censored for my presence.
“I can tell you guys are happy I’m here, but that it’s awkward. In good faith, I’ll put tonight on my charge account with the company. Just relax. Claudia and a few more officers, myself included, think that upper management could stand to get to know our staff and really hear them out on what the company is like for them,” I said, reassuringly.
The conversation relaxed much more after that. A few minutes later Miles came to sit near me.
“That was pretty awesome,” he said.
“I don’t know about that. It could have backfired. I could have been accused of liquoring them up to make them tell bad things about each other,” I replied, jokingly.
“Well, I have never had anyone in upper management come out with the staff and buy drinks,” he replied.
“Well, it’s hard to get to know people when they feel guarded. I’m having an Old Fashioned to ease into the situation myself. You may as well have something. I’m paying,” I said.
He stopped to think for a moment. I knew the moment I saw the face he made for this internal debate that I wanted to see more faces he could make. His thinking face made him bite his lip just slightly. I wanted to do that, too.
Chapter 7
Miles
“I really try to stick to one or two drinks normally, but you’re great. These guys are just great. I’m excited about my new job,” I said.
I could hear myself and could tell that I was babbling like a drunk college girl. I wasn’t far from it. I was six foot tall, but I weight maybe 175 pounds on a good day. I had drunk two shots and three Old Fashioneds in my night out with my coworkers.
Everyone from work was gone. Most had families or were middle aged and went to bed a little earlier. Others who were still single decided to find a place to go dancing.
“So, why didn’t you join the girl you came with to the next hot spot?” Tyler asked.
“Me? I don’t dance. I can’t dance,” I said, shaking my head.
I pushed away the glass in front of me.
“You didn’t go either. I think a couple of them were interested in you,” I noted.
“Well, I think the better company was here,” he replied.
He finished his drink. He handled his liquor much better than me. He seemed to be as composed as when I saw him in his office, but dressed more casually and a little more relaxed.
He had stared at me off and on in our conversation and as my mind wandered back from assessing him I realized he was staring at me again. Before I could comment on it, he leaned over and kissed me. Before I could think about it, I kissed him back.
“Um, I’m straight,” I said, pulling back.
“I think you just realized you don’t know what you are,” Tyler said, sitting back as though he had never moved.
I opened my mouth to speak, but wasn’t really sure what to say. Instead, I stood and felt for my wallet. I placed money on the bar. I didn’t know if it would cover my drinks or not, but I knew my point would be made. I turned to leave and Tyler grabbed my arm.
“Look, sorry about that. I misread you. Let’s not mention this at work, okay?” he said.
I nodded. I grabbed a cab to take me home. I could come get my car tomorrow.
At home, I couldn’t stop thinking about what could have happened if I had gone out with Marjorie instead. The whole thing with Tyler could have been avoided. I also thought about my response to the kiss. I wasn’t angry. I was shocked. I was shocked it happened and shocked that I returned the kiss.
Thinking on it, it was a good kiss. It was a good kiss not just because it was a good kiss, but it made something spark inside me. I hadn’t felt anything quite like this with the few girls I had dated, not even the two I had slept with a few times in college.
Once I was awake and sober the following morning, the kiss was still on my mind, but I also realized in the moment I had sense enough to make myself clear that I wasn’t interested. I assumed th
at meant even drunk, I liked women. I felt bad about not taking the opportunity to spend time with Marjorie, so I invited her to diner and drinks, just the two of us, the following Friday night.
When she said yes, I felt relieved.
Chapter 8
Tyler
“So he didn’t bite?” Claudia asked.
She and Tina were in my office first thing Monday morning expecting either juicy details of a lustful weekend or my turning a new leaf in the name of love. They both seemed genuinely surprised at the possibility of neither.
“I have seen straight men become gay just at the idea of you. You kissed this guy and he just left?” Tina said, flabbergasted.
“Yep, some challenges are only there to remind us of our limits,” I said.
I saved face for myself and Miles. I was sure he would act awkward or quit now. I knew I felt him kiss me back, and I knew the way he left meant he knew there was some new or repressed feeling he would have to deal with.
“Well, it is certainly nothing I can’t move on from. There is a lot going on in the company right now, some interesting things on the horizon, and some people I think we should discuss as key players,” I said, redirecting their attention.
I had Claudia on board and, as always, Tina was my partner in crime. We were diligently working on a personal project of mine that could have a large effect on Sir Name. Each of us were also using this get-to-know-the-staff thing to look for key players in the changes I was proposing.
“I would like to consider Miles. I think once he and I can discuss things and he can relax again, he will be an asset to this new project. He is a recent graduate with an energy that is appreciated by those around him. He’s pliable, but also firm in his ideals,” I said.
“I think he carried himself well when he came to your office. Chase has been spreading the word that he has only had Miles a week, but that he has the best assistant in the building,” Tina said with a shrug.
“Well, my impression of him is only based on knowledge at a distance from last week’s meeting and what you’ve both said. I will have to feel him out at the meeting this afternoon. There is not a lot on the docket to be discussed, so I will make it a point to introduce myself after. If we are going to consider him to be a part of such a large project, he will have to have my personal stamp of approval,” Claudia said.
We discussed a few other people we each needed to take a little extra one-on-one time with. Then we resumed business as usual.
Instead of having my usual lunch brought in, Claudia and I had lunch brought in for each floor. We had it staggered to arrive for two floors each hour. I ate lunch when five and six were delivered.
“Have you gotten something to eat yet?” I asked Miles.
He was at his desk, outside Chase’s office. He shook his head.
“Well, let’s get something together. I want to talk to you,” I said.
I was trying to approach him tactfully. He may not have been my next playmate, but he was still a valuable asset businesswise.
He thought for a moment. I still liked his thinking face. Then he nodded and got up from his desk. We walked to the food and picked a few things we liked in silence.
“I apologize for what occurred the other evening, but I want you to continue to feel as comfortable as you did before at work. This is water under the bridge if you choose to let it be,” I said.
“Yeah, that sounds good,” he said.
He seemed to relax a little. He ate bite of food as we were walking toward the elevator. He broke the ice with a small joke about the previous outing.
“Yeah, never would have happened if you’d seen me dance,” he teased.
We laughed a bit at both our expense. Then Marjorie arrived with her dessert to share with Miles. As I left, I overheard Marjorie whispering loudly.
“I’m looking forward to alone time with you Friday,” she said, giggling.
He could do worse for an office romance. He could also do better.
Chapter 9
Miles
Lunch with Tyler had reassured me about my decision to remain with the company. Dessert with Marjorie made me realize I had half-hearted feelings about our date.
All the same, Friday night, I showed up at her house with a small bouquet. We went to dinner and had drinks.
“It’s amazing that we would be made assistants at the same time, don’t you think? It is like fate made a job for you and a promotion for me, so we could sit next to each other and spark conversation,” she said.
I nodded.
“Yep, the universe wanted us to get to know each other,” I said, hoping to slow her talk about fate down a little.
“The better I get to know you the better I like you, Miles. Miles and miles,” she said.
She was repeating my name, half singing. She kept giving me bedroom eyes across the table and reaching to touch my hand or face. I tried my best not to be rude, but the entire situation felt wrong.
There was still a lot on my mind about the past two weeks. I had started a new job, been kissed by one of the bosses who was also a man, and started dating a woman who had commitment and fate on the brain.
“I don’t know what I’m doing,” I said.
“Excuse me?” Marjorie asked, still smiling.
“I don’t know what I’m doing. Work seems to be going smoothly, but I think my personal life needs some attention,” I said.
“Well, we can go back to my place and I can give you all kinds of attention,” she said.
This seemingly quiet woman had become all vixen tonight, and everything in me was not interested. She looked beautiful, and I knew it. I also knew that she didn’t make me feel anything.
I placed money on the table for the meal and a cab for Marjorie. I mumbled some kind of excuse and apology and just left. After riding around to nowhere in a cab for a while, I decided to go to the office. I could work on some of the projects I had from Chase.
Once I was inside the building, I rode the elevator to six. When the doors opened, I stayed in the elevator.
Chapter 10
Tyler
I stepped out of my office to Tina’s desk to get back a file I’d left with her earlier. I was surprised I wasn’t alone. I was more surprised that the person before me was Miles.
“I left a date and came here,” he said.
“You shouldn’t be working this late,” I said.
“You are,” he replied.
“Well, I drown myself in work when there is a problem,” I said.
“What is your problem?” Miles asked.
“Well, I’ve always been a bit of a playboy, but I think I may be interested in taking things slowly with someone I met recently,” I said.
He nodded. Then he offered a confession of his own.
“I keep busy when I have problems, too. I’ve always been a bit relationship shy, but I’m starting to think it is because I’ve been trying to have the wrong kind of relationship,” he said.
We both looked at each other for a long moment. The tension in the air was thick and my basket was getting thicker, too.
“Come on,” I said, leading Miles into my office.
He came in quietly and closed the door. He stood beside a visitor chair at my desk. Even nervous, there was something about him I couldn’t take my eye off of. When I put my hand on his wrist he stepped in place just a little.
“Is this okay?” I asked.
“Yeah, I was just sorting in my head what is about to happen and if I would want to be top or bottom and how to phrase asking about it,” he said.
I kissed him, and felt him kiss me back deeply and relax. We both stepped closer together surrendering to the kiss more deeply.
“Don’t think about it. Sex is something where your body can naturally guide itself to pleasure,” I said.
Chapter 11
Miles
I knew I had made the right choice leaving my date. When I reached the top floor, I saw Tyler at Tina’s desk. He had taken off
his tie and jacket, and his top few buttons were undone.
The arousal I had always imagined I should feel when I slept with a woman flooded me immediately. As he kissed me now, in his office, I felt harder than any time I could remember.
I was surprised when he touched my dick, and I jumped a little. It was like sparks ran from the head down the shaft. He moved into me more until my hip bumped his desk. As he continued to kiss and stroke me, he guided my movements until I was sitting on the desk.
He lifted my shirt over my head and unbuttoned his own. He unbuttoned his pants and pulled out his own cock, rubbing it intently. He took my hand and encouraged me to stroke our dicks, too. He stepped back into me and kissed me. I enjoyed it.
I liked the scent of the day on him after he had been at the office working. I liked feeling his cock in my hand and occasionally rubbing against my own. As he took my cock in his hand again I felt myself spasm slightly and erupt with a bit of precum.
He knelt and licked it of the tip of my dick. Then he hoisted me back, pulled my pants off, and tossed them on a chair. Before I could ask what we were doing next he started licking my ass.
“One of the things I really enjoy is a good ass blow, particularly if I’m receiving. It relaxes me and excites me all at the same time. Luckily for you, I am a bilingual artiste,” Tyler said.
“I don’t understand any of that,” I said, feeling my ass pulsate with every lick of his tongue and my dick throbbing as we both moved our hands up and down.
“I enjoy rimming, giving and receiving depending on if I feel like being top or bottom, I’m great at oral, and I’ll blow your cock and your ass,” he said calmly, still working me with both hands.
I could feel myself starting to rock and want for something.
“Talk to me,” Tyler said. “Tell me what you want to do. Tell me what you want me to do. Tell me what you want to experience.
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