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Jason, my Somnambulist Boss, Part 3

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It was a Wednesday morning, just past 11 AM, and Jason and I had just boarded the airplane for the first leg of our journey to New York. We would have a short layover in Chicago before finally arriving at our destination around 4:40. I had never been seated in business class before and I did feel a little fancy. It’s weird how you dress differently for a flight when it’s work-related. I wore a white shirt and grey slacks. Jason, unlike me, had been to the office before coming to the airport. He wore a dark blue blazer and matching slacks with a lighter blue shirt. He looked amazing as always. He had kept the boss persona up while we waited at the airport. He was reading this folded up newspaper and had only asked me work-related questions. It was only recently I had started to unravel what was behind Jason’s mask, and I was intrigued to know more.

“So, have you been to New York before?”, I tested the waters. “I have”, Jason replied. He then looked at me and followed with, “Actually, New York was the reason I wanted to stay in the US initially.” He paused again and looked away. “It’s where I fell in love for the first time. I don’t go back enough, it’s a great city.” I don’t know what it is about this guy, but he barely ever opens up about his personal life, but now he did, it was surprisingly intense. “It is, it is”, I said, absent-mindedly. I looked out of the airplane window. I had gotten the window seat. Jason preferred the aisle, which made sense as he was taller than me. The next few days could get quite interesting. I had an opportunity to get to know my boss better, if he would let me. He had been in the office for quite a few months now, almost half a year, and really all I knew about him is that he’s 32, from New Zealand, single, went to law school in Chicago… and he is a somnambulist. Oh, and he likes to play with a dildo.

I looked back at him and saw he was fidgeting with his seat belt as the plane started taxiing. “You OK?”, I asked. “Yep. I get a little nervous for take-off and landing, that’s all. I’ll be fine.” He continued to look ahead and play with his seat belt. Somehow it seemed unlikely that someone who moved to the US from New Zealand would be a nervous flyer. But I didn’t say that. Instead I tried to reassure him. “All right, we’re going to be fine. Keep breathing.” “I am. I am fine. Just a little nervous, that’s all.” “You know, hypnosis can be really relaxing…” Now he turned his head to face me. His expression was one of confusion, disbelief almost. I could tell he didn’t know what to say. “Not… here. Not now”, he managed to blurt out. “Why not?”, I asked. “You’re clearly nervous. Let’s see if the suggestion still works!” The plane was clearly getting to its takeoff strip. Jason looked straight ahead again and lightly shook his head. I knew he wanted to stop me, but I knew I had to snap my fingers. “Sleep!” I saw Jason’s eyes roll back, his head flopped forward and then toward me, ending up on my shoulder. His entire body flopped over and ended up leaning against me. His left hand fell out his lap onto the chair, with his palm facing up. “That’s right, deeper and deeper”, I said softly in his ear. “So relaxed and calm. Take slow, deep breaths. Your mind is free of stress, worry, and tension. That’s right, deeper and deeper.” The plane took off. I looked across the aisle, and Jason’s sudden loss of consciousness had thankfully gone unnoticed. Then I spotted something moving. Jason’s bulge was growing in his tight-fitting trousers. He wasn’t full-on pitching a tent, as he most likely had underwear on. But the bulge that had been there before was now growing in the limited space of his crotch so I could basically see the outline of his cock in his briefs rise up. It looked very hot and I was getting quite turned on myself. I had never had Jason’s body this close to mine. He smelled great.

I realized the plane had taken off. I again spoke softly into Jason’s ear, while I felt my hard-on grow. “Soon, I will wake you up from trance. You will feel awake and refreshed, calm and relaxed. And every time you fly from now on, you will be able to remain relaxed during both take-off and landing. You will realize there is no need to get nervous. Nod if you understand.” I felt the head on my shoulder move. “I will now wake you up from hypnosis. 3… 2… 1… Eyes open, wide awake.” Slowly Jason’s head moved off my shoulder. The first thing I saw him do was wipe some drool off his chin. “What… I…”, he mumbled as he looked around. He looked at me and then at my shoulder. “Oh, man, I’m sorry. I got some on your shirt.” “That’s all right”, I said. He sat straight up and clearly only then realized he had a boner. So he quickly covered his crotch, but he didn’t mention it. “You… put me under?” “Yeah”, I said. “How do you feel?” “I feel very relaxed. Thanks.”

Jason’s relaxed state was obvious, as for the rest of our trip, he dropped the boss persona and chatted to me about several things. Why did I choose to follow the hypnosis course, where I lived and how I liked my neighborhood, about how he ended up living downtown, and we even gossiped about some of the co-workers. He clearly was a really nice guy, he just didn’t show it in the office. He didn’t flinch during take-off or landing for the second leg of the trip. Before I knew it, we had landed at LaGuardia.

At the airport, there was someone waiting for us with a sign that said “JASON WHITTINGHAM”. We were driven to our hotel, not in a regular cab, but in a luxurious car. I felt very fancy. Jason acted like he was used to this, but when we got ourselves into the leather seats in the back, he said “I’ve never had my name on a card at the airport before” and smiled.

It didn’t take the driver long to get us to a highway. Jason told me about the schedule for the conference. All of tomorrow and Friday morning would be the conference, with a formal dinner and party on Friday evening. So this evening we could just wander around and do whatever. I suggested we go for dinner and drinks, explore the town. Jason agreed, but did say we had an early morning tomorrow, so nothing too crazy. Oh right. He was the boss. I looked out the window to my right and suddenly saw the New York skyscrapers in the distance. We crossed a bridge and the skyline I had seen on photos and film so often was now actually right there. There was quite some traffic, but I was fine sitting in this nice car, with Jason right next to me and the views out the window. Not too much further, the skyline was now right in front of us and we were heading straight for it. “Wait, where is our hotel?” “It’s near Ground Zero, I think?” “Oh wow!” “I know, they really went all out putting us right downtown”, Jason said, looking down at his phone. When we finally exited the highway, I got very excited about where we would end up. I had actually never been to New York, as much as I had travelled around the States, I somehow never made it to New York. We went down Flushing Avenue, quickly turned onto Navy Street, and by the end of Sands Street I could see the skyscrapers again, this time a lot closer. “Is… Is that the Brooklyn Bridge?” “Yeah”, the driver said. Jason also looked up. “Pretty, isn’t it?” “Yeah, it’s cool”, I said, trying not to sound too much like a tourist.

Once we got off the bridge, the driver made a big turn and we ended up driving by the East River, the water to our left. On the right, there was nothing but tall buildings. We went into an underground tunnel and then tall buildings surrounded us. Much like I always thought I would in New York, I felt tiny. I looked around in awe. The driver said, “This is your hotel”, as he parked near a tall building on the right side of the street. It was a Marriott hotel. The driver took our luggage out of the trunk. He said the service was paid for by the company, so Jason just tipped him. We walked into a beautiful lobby and checked in. “Anything you consume at the lobby bar behind you can be charged to the company. It opens at 4:00 PM every day. Your conference tomorrow and Friday will start at 9:00 AM in Grand Ballroom Salon A, which is on the third floor. Here are your key cards for your room, which is on the 25th floor. Elevators are right over there. Mr Salcedo, Mr Whittingham, enjoy your stay.” “Thank you.”

When we walked into the room, I couldn’t believe what I saw. I walked into what seemed more like a small living room, there was a desk with a chair, with a large sofa and a more comfortable chair, a big TV, some cabinets, but no bed. I walked to the window and admired the view outside, which showed the Hudson River. On the right there was a door to the bedroom, which had a kingsize bed and another TV. On the right there was another door, to the bathroom, simple but sufficient. Through the bathroom one could walk back into the living room area. I had never been in a hotel room like this. “There’s only one bed?”, Jason said. I found him in the bedroom. “It’s a big bed though”, I argued. “I guess because they expected me to bring a partner…”, he started. “Not a big deal though, right?” I could feel my heart beating in my chest. I really wanted Jason and I to share this bed. I needed to convince him without looking like I wanted it too much. “I can sleep on the sofa”, was his proposal. “No, that’s crazy. It’s a big enough bed for the two of us.” “You sure?” “Absolutely.” “All right.” It worked.

I claimed the bathroom first as I was dying for a hot shower and to slip into something more comfortable. I took my clothes with me into the bathroom and came out feeling fresh and clean, wearing a stripey T-shirt in blue and green and light blue jeans. I found Jason on the sofa, he wasn’t really watching anything but continuously changing the channel. He didn’t look up when I came in the room. He was still wearing the light blue shirt, but it was untucked. The blazer was draped over the sofa, right next to him. He sat with his legs wide, which I always considered something very sexual, as my eyes went straight to his crotch. And with his tight pants, it was quite the sight. “Do you want to go for a walk around and grab a bite to eat soon?”, I offered. “Oh, yeah!”, he said, excited. Now he looked at me. “I also need a shower and a change though. Give me 15.” “Sure”, I said. Jason walked straight into the bathroom. I went to the bedroom and started hanging up some of my outfits in the one closet. I heard the shower go, and Jason sometimes sang a little tune I could not recognize. He wasn’t a very good singer. It kept popping into my mind that the bathroom had two doors, and I wanted to check if he had locked both. But I didn’t.

I continued unpacking until I heard the shower stop. Jason’s suitcase was right here in the bedroom, unopened. It dawned on me what was about to happen, just as it started happening. The bathroom door opened and Jason walked in with a towel wrapped around his waist. His upper body glistened from the water and he looked superhot. His beautifully smooth body walked in and went for the suitcase. He bent over in the towel and his ass looked great, but I really wanted the towel to drop. “So, I’m in the mood for sushi, you OK with that?” “Sure”, I stammered, not looking away. Then I found out just how little he cared as he stood up and threw the towel on the bed, still facing away from me. His ass was a beauty in real life. Perfectly round and smooth. Only once they covered his ass I realized he was putting on white briefs with a black waistband. They still made his ass look phenomenal. He then put on this dark blue T-shirt and some jeans. “Right, I’m good to go”, he said once he was dressed. I looked back at what I was doing, hoping he hadn’t noticed. He walked toward me and put his arm around me. “You ready to explore NYC?” “Heck yeah!”, I said. Well, this was a change of character. I loved it!

In the elevator, Jason was looking for the nearest sushi place. He had clipped his sunglasses into the opening of his T-shirt, so that it dangled on his chest. It was a nice evening in June, weather was great. “Do you wanna pass by the Ground Zero memorial on our way to dinner? It’s right next door!” “I don’t know, is it the type of place to just pass by?” “Maybe you’re right, we’ll have more time Friday afternoon.”

In under 10 minutes we walked to Blue Ribbon Sushi Bar. We literally sat on stools by a bar and had some amazing sushi. The conversation was also great, Jason had completely loosened up. Jason talked about how he loved good food, but was a complete mess in the kitchen. I said I loved cooking and he said I would have to teach him sometime. “Well, you’ve got one important bit down”, I said, “get your ingredients at the farmers’ market when you can!” He laughed. “My friends, Tom and Tyrone, they do make really nice food. They made me dinner that day.” “They seem like fun, how do you know them?” “I met them at this bar, I don’t know if you know it. Belle’s Basix?” “I’ve heard of it”, I said. As far as I knew it was the only gay bar in Cedar Rapids. Jason still hadn’t technically come out to me, but at this point I would be shocked if he wasn’t gay. “It’s quite a bit up North, like just before Memorial Park?” “I don’t really get to those parts of town”, I said, which was true. After years in Cedar Rapids, I had mostly stuck to downtown and my own neighborhood. Belle’s Basix was the type of bar with drag performances, which wasn’t really my scene. I preferred a quiet pub. “I’ll tell you what, you help me make a nice dinner, I’ll take you dancing, what do you say?” “Sounds like a plan”, I said. Also sounds like a date. Was I imagining this?

After dinner we walked around a bit, and found a bar to have a drink. I mentioned I was having a great time hanging out with him. “You’re quite serious in the office, so this is a pleasant surprise”, I said. “Yeah, I know what you mean”, he came across sincere. “I’m still so young, and I feel like I need to act a certain way to be taken seriously as a supervisor, you know?” I nodded, and I actually did understand. “Is this the first time you have people working under you?” “Only if you don’t count team manager at Starbucks during college”, he smiled. “I can imagine this was intimidating for you then”, I said. “It really was. And people like Reda and Taka, I just really want their respect. They are so experienced, and I’m sure they wanted my job”. “I don’t know if they did, but I know they respect you”, I said. “Thanks, I appreciate you telling me that”. He smiled at me again. His smile lit up his face and made his gorgeous eyes hard to look away from. He put an arm around me. “What do you say we head back?”, he suggested. I looked at my watch and it was 10:53 PM. “Long day tomorrow”, I said. “Let’s head back.”

By the way he walked, I could tell Jason was a little tipsy. I’m sure he wasn’t used to my pace of drinking, considering he had a body like that. “It’s been a while since I’ve had this much to drink”, he admitted when we walked into the lobby on our way to the elevator. “You know”, Jason suddenly changed topic, “did they ever say anything on the course about people getting aroused in hypnosis?” Oh wow, he did have a lot to drink. I laughed. “No… Sorry”, was all I could come up with to say. I pressed the button for our floor. The doors closed. “Because I think I know what it is. You see, in bed, I like to be the submissive one.” “Jason, I think…” “And being hypnotized is like, giving away all control, right? The ultimate submission. I give you my conscious mind”, he laughed. I got a bit uncomfortable with him talking like this, so I didn’t react. “Erick, come on! I know you’re gay!” “What?!” Ding! The elevator doors opened. “I saw you in the reflection of the window, checking me out when I changed!” Jason walked into the corridor to our room. I didn’t know what to say. “So?” I followed him. “It’s OK, I am too!” “…yeah?” “It made me so happy when I found out, because you have this power over me to get me all worked up, and now I feel like it’s a more level playing field that you like to check out my body.” I opened the door with my key card. “But I love how I feel whenever you w-wake me up from hypnosis, it’s so hot. Don’t you wanna play some more? Are there any sexy suggestions you can give me?” Jason’s sexually playful tendencies I had been aware of. I had not expected them to come out during this trip. I felt unprepared for the situation and didn’t know how to act. Yet at the same time, this was great. “First, let me use the restroom”, I said, buying myself some time. “All right!”

In the bathroom, I calmed down. I was out to Jason. Or, well, Jason had outed me. And himself. And he wanted to play. For now. Once he was all sobered up tomorrow, he might think differently. By the time I had calmed down from the rollercoaster of a conversation I had just been in, I got excited. I opened the door and saw Jason in just his white briefs, face down on the bed. He had passed out. His ass was like two perfectly round hills covered in snow. He looked hella hot. But no hypnosis play tonight.

To be continued…

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