One Year Internship Ch. 12 – Week 15

CHAPTER 12

Week 15

I am more than 3 months in. More than 25% through this long, intense, energy draining, crazy internship. At this point, I feel like I have settled in. I have explored the rest of the complex, finally, and know where to find things and who to talk to if I need anything.

Financially, things have still been going quite nicely. No huge sales commission recently, but I am still doing well. I am past my probationary period, so my paychecks have started to get bigger. Apparently, they will continue to grow each week until the very end. I am up to almost $90,000 in my bank account. It is crazy to see it just go up and up. I have not had a single debit from the account since I started this internship. Even the birthday gift I got my mom, was approved by Steve, and paid by the company.

Speaking of which, I started taking advantage of the advice that Shana gave me to buy more things. Steve was a little nervous at first, but I suggested that he talk to Shana. When he did, she gave him a lecture about keeping me happy and approving anything I want. I think her words were, "Jon doesn't care if she buys herself a car. Approve it."

I don't think I will push for a car, but I ordered a slew of new clothes, a few pieces of jewelry, a bunch of makeup, and health supplies. I even upgraded my phone. I have blocked off 2 hours every Saturday afternoon, just to shop and I have a list on the counter next to my fridge in case I think of something specific before then.

My escrow is up to a mind-blowing $270k. I mean, I could pay off my parent's house for that. Sometimes I question whether that escrow and the deal I made is real. Nicole convinces me it is every single time I ask her.

I have continued my insane workout regimen. It is like one day I saw some progress in the mirror, and it tipped me over into an exercise addict. Ashley's workout is doing wonders, as I am down to single digits body fat, and I can see excellent definition in my abs. I wanted to eat better to accompany my workout, so I proposed to Shana and Jon that they hire a nutritionist. They agreed and he starts next week. I am looking forward to working with him and seeing how much more progress I can make.

I am maybe a third of the way through the sales certification. Victor was excited by my pursuit of it and has wanted to meet with me twice a week to review the content. The unexpected benefit for him is that we have used me as a guinea pig to improve the content. He has taken several of my suggestions and is working with the education department to update the training.

The bad result is that we have been so busy with the sales training discussions, that even though we have met more than a half dozen times in the past few weeks, we have not done so much as share a kiss during any of them. I know that Nicole keeps telling me to be thankful any time I can get away without any sexual activity, but I feel some unexplained attraction to Victor.

Executive mentoring has been slow the past month or so as well. Marsha has been a bit busy, so she has canceled a couple appointments. Stella was on vacation for two weeks, so I did not have my usual sessions with her either. I have not been able to spend any more significant time with Jon since our adventure in the apartment a month ago. All our run-ins have been in passing or had a business agenda. He assures me that another opportunity for us to be together is coming up.

I had dinner with Lance and Nicole last week. They are doing amazing in the first few weeks of their official dating relationship. We did not have any intimacy, but I felt the love and warmth from their visit. They seem super happy, like a weight has been lifted from their shoulders.

My calendar has been overly full of appointments the past few weeks. I asked Nicole about it, and she explained that it takes several weeks for word to get around to the rest of the middle layer that I am available. She also noted that right about now, I should be seeing several people putting reoccurring appointments on my calendar once they have experienced me once and decide they want to do it regularly. Both of her comments were right on when I went back to audit my calendar.

Friday last week, I had 9 straight 30-minute appointments just for blowjobs. By the end of the day, my jaw was sore, and for the first time, I was truly tired of tasting cum. Looks like it is more important than ever for me to block off time for myself. Otherwise, I will find myself sucking and fucking 12 hours a day.

I am sad that I have not had a follow up visit from Shana. I have seen her a few times, as I am on the 8^th floor often. She reassured me that she is not avoiding me. To prove it, she pulled me into a conference room and initiated a passionate kiss. She told me that she would set up time with me soon, to discuss some ideas she has related to improvements in the compensation for my role, and "maybe for some other stuff."

It is now Friday afternoon. I blocked off the late afternoon this time to recover a little bit from the busy schedule and to get ready, both mentally and physically for this evening's date. That's right, a date. Curt, our CIO asked me during our mentoring session if I would be willing to go on a date with his nephew. "What's wrong with him?" I asked.

Curt laughed it off and said, "He is an intellectual and has focused on his studies. So, he has limited to no experience with girls."

"So, he's an awkward virgin then?"

He shaped his fingers into the shape of a gun and as he shot me, he replied, "Bingo!"

I frowned. "And what are your expectations from me on this date?"

"Show him a good time."

"That means different things to different people Curt."

He leaned forward to give me his full attention. "Listen, let me be honest with you. He is the youngest son of my youngest brother. The whole darn family is awkward. I am trying to insert myself a little bit to potentially alter the path of this young man. Maybe have him be more like his uncle Curtis."

He chuckled at his own compliment. I replied, "Okay..."

"Flirt with him. Give him some confidence. Then use your charm to see what happens."

"See what happens? Are you hoping I sleep with him? Take his virginity?"

"If he is lucky enough. Megan, I know this is unusual and does not really fit under the umbrella of your job role per se. But it would be a really big favor to me. I will make it worth your while."

So, here I sit, Friday afternoon, reapplying a little bit of makeup after taking yet another shower to make myself clean and ready for any kind of sex that may come my way tonight. It has been a long week.

I took an uber and met him at a restaurant that I found out later was Curt's suggestion. I was looking forward to being away from the office or surrounding areas for the first time in more than a month. Even though I was 10 minutes early, he was already at the table. He was focused on the menu and did not look up as I approached. "Thomas?" I asked.

It must have taken him by surprise as he dropped the menu, almost knocking over the glass of water in front of him over and practically knocking the chair over getting out of his seat. A few people looked over to see what the ruckus was. His face turned a bright red, and he looked like he wanted to crawl under the table. As the restaurant went back to normal, I extended my hand and introduced myself.

He replied, "Hi I'm Thomas. I guess you already knew that. God, I'm such an idiot. I'm sorry."

"It's okay Thomas. It is nice to meet you."

He pulled a chair out and indicated I should sit down. Signs of him being a gentleman was a good start to the night. Once we were seated, he commented, "I apologize for seeming clumsy. I know it's not a good first impression."

I laughed. "Don't worry about it. I am sure before the night is over, I will have my own moments."

I felt like that eased his concerns a little. Conversation after that was the usual feeling out process and learning about each other. I had to lead most of the topics, and I tried to insert compliments and flirt whenever I had a natural opportunity. I could tell he was very nervous.

Thomas was nice looking in his own way. He was clean shaven and had a well-structured face. He had a few random pimples showing his youth. His brown hair was a little messy, but he looked like he tried to get himself together for this date. While his clothes did not exactly match, they were nice quality.

As we made our way through dinner, Thomas started to demonstrate his surprisingly diverse knowledge on several topics. But every few minutes, an instance of social awkwardness would pop out. I rubbed his leg with my foot, to flirt a little, and he stopped eating to look under the table to see what was happening. When we had dessert, I tried to feed him a bite of my tiramisu and he froze up, not quite knowing what to do.

Our meal was finally over, and he paid the bill. We walked out of the restaurant, and I asked him what else he had planned for us. He froze again. I realized that he had not planned anything for us; that he really was completely lost on what to do on a date with a girl. The restaurant was in a quaint part of downtown that had several stores and shopping along the rest of the main street. The scene was nice as the light poles and trees were decorated with white lights. I suggested we go for a walk and talk about ideas.

As I guided him down the street I asked him, "Thomas, how many dates have you been on?"

He fumbled around a bit and then asked, "With a girl who was not just a friend?"

"Yes, an actual date that you might have a romantic interest in."

"And a date with one of our parents chaperoning does not count right?"

"Let's take those out as well."

After a moment of silence, he said, "I hope you don't think less of me, but this is my first actual real date." He mumbled some harsh criticism of himself before I could respond. My assumption was confirmed. I was completely set up to be a guinea pig.

I replied, "Thomas, it is completely okay. Everyone must start somewhere."

I stopped walking and forced him to turn and face me. We were close to eye level, and I demanded his attention with my gaze. I continued, "Thomas, I am open to doing anything you want to do tonight. I want this to be an amazing date for you. Tell me, what you want to happen tonight?"

Even in the twilight, I could see the despair on his face. I had put him on the spot. He struggled to begin a response. I wanted to make the process easier for him, so I turned and started walking and pulled him with me. I continued, "I guess we can figure this out as we go."

As we walked, I asked him more leading questions about what he liked in a girl, and what things he would feel comfortable doing. At some point, I stopped again and faced him. "Thomas, have you kissed a girl?"

He nodded no. I asked, "Would you like to kiss one? Like me? Maybe right now?"

He nodded shyly. I leaned in and kissed him. I kept our lips pressed together and waited to see if he would press the romantics. When he didn't, I pulled away. But stayed close. "Did you like that?" I asked.

He nodded. I did it again, lingering a little while longer. He softened and I gave him the slightest bit of tongue. He pulled away a little in shock. "Are you okay?" I asked him.

"Yeah. That just surprised me."

"Okay. I want to do it again."

We kissed again. This time he did not pull away when I gave him some tongue. He tried to kiss me back, but it was clunky. When we broke our kiss, I asked, "Did you enjoy that?"

"I think so." He sighed heavily. "I am probably bad at it, so you probably didn't enjoy it."

I smiled at him. "You just need some practice. Do you want to practice some more?"

As he took my hand and led us down the street he replied, "Maybe later."

We made it to a park at the end of the street and sat on a bench. I scooted right next to him, so our legs were completely touching. I took his hand and wrapped it around my shoulders and put my hand on his thigh. I let us marinate in the moment to see whether he would settle in.

After the moment of silence, he asked, "Megan, why are you on this date with me tonight?"

"You know why. This is a blind date coordinated by your uncle, who I work with."

"What did he tell you about me?"

"Practically nothing."

"Sounds like him. So why did you agree to it? I mean, you could be on a date with anyone. And yet, you are here with me."

"Maybe I am a bit of a rebellious wild child and wanted to see what happens tonight."

There was another pause that seemed to last an unusual amount of time. I finally broke down and asked, "Why are you asking Thomas?"

"I am not stupid Megan. I am an inexperienced nerd that would never have a shot of getting you to talk to me let alone going on a date with me. And now you kissed me and are offering to kiss me again, even though I suck. If I did not know better, I would swear you lost some bet or something."

I laughed and turned to face him. I kissed him again. It was nice and he did not shy away. I finally pulled away and commented, "In the past hour or so, I have learned you are a sweet considerate guy who just lacks some confidence with girls. I want to make this a great date, for both of us."

"And what would make this a great date for you?" he asked.

"I would like you," I poked him in his chest. "To break out of that shell and go for it. Enjoy yourself with a very willing date that wants to have a good time."

He laughed. "Go for it? That's what you want?"

I smiled and nodded my agreement. He asked, "And what if I mess up and do something stupid?"

"You might not do something as well as an experienced person might do it. But it does not make it stupid. Relax and enjoy yourself. Try new things. I am a very chill person."

He looked at me hard. I could tell he was processing. He surprised me be leaning in and kissing me. He drove the action, sliding his tongue into my mouth. It was still a little clunky, but I liked his assertiveness.

He pulled away finally with a big smile on his face. "Like that?" he asked.

"Just like that."

He flashed his biggest smile of the night, "What do you say we go somewhere more private so we can try some other things?"

I energetically nodded. He pulled out his phone and ordered us an Uber. About 15 minutes later, we pulled up in front of Curt's house. Thomas had explained that his uncle offered it to him, just in case, noting that he and his wife were going to be out of town for the weekend.

Thomas let us in, and we made our way into the living room. The house was a bit cluttered, like it had too much furniture and had things on top of the furniture. The walls had so many pictures, that none of them could breathe. I could see that Curt's personal life was much like his work life.

As I was taking in the room, Thomas stopped next to me. I moved my gaze to him. He looked at me very intently and said, "Megan, I have no idea what I am doing. Only in my greatest fantasies am I alone with a hot girl at the end of a date. I am scared shitless that I am going to do something or say something that is going to turn you off and you are going to bail on me and leave me here in my own disappointment. But I am equally scared that I am not going to take advantage of this opportunity that may never come again, and I will hate myself for it."

I felt bad for him. I smiled gently, trying to ease his concerns. I replied, "Well Thomas, we have two paths forward. One, you can tell me exactly what you want to do tonight, and we can do those things. That is a very methodical and predictable and mostly stress-free approach. Or we can sit on the couch, throw the tv on and see what happens."

There was a pause while he considered those options. "How about I go get us a beverage and I will think about it and tell you when I get back."

I nodded and he left toward what I assumed was the kitchen. While he was gone, I considered what I was willing to do with this guy. I was never the person to be attracted to nerds, even innocent, somewhat charming ones. I was also never the person to have sex on a first date. But well, I have done many things a bunch of times that I never would have seen myself doing 3 months ago.

By the time he returned, I had reminded myself that all day long I have sex with people as my job, doing whatever makes them happy, even if it does not pleasure me. I convinced myself that this was no different and that I was going to do what I could to bring excitement and pleasure to Thomas tonight. I would get pleasure out of making his first date one he would never forget.

Thomas handed me a root beer in a glass with ice. "I hope this works for you. Uncle Curtis does not have much of a selection to choose from."

I took a drink and nodded my approval. I asked, "Have you decided?"

"Yes. I think I want a little bit of both."

I frowned, "How can it be both?" I asked.

"I want to do as much as you are willing to do. It would be amazing to have as many firsts as I can tonight with you. But I will totally understand if you are not interested."

"Okay. What is the catch?"

Bashfully he replied, "I want you to drive. I want you to initiate. I want you to lead. Since you know what you're doing of course."

I caught his embarrassed smile. There it was. I now understood. "Can I ask you something Thomas?"

"Of course. What is it?"

"I am a super relaxed person and whatever happens tonight happens and however it happens it's fine, but I'd like to give you advice along the way. I want you to learn, so that when you are on another date with someone else in the future, you have a little more experience and be better prepared. Is that okay?"

"Yeah of course. That would be amazing."

"For example, I have a couple pieces of advice right now."

Thomas looked nervous. I continued, "You should have more confidence. You are a funny, well-educated guy. And as you get more experience, what to do on dates will become more natural and easier."

He nodded. "Also, I think the restaurant was a good touch, but you should always consider what other things you can do on a date in case it is going really well, and she wants to spend more time with you."

He nodded again.

"Does your uncle have any movies we can throw on? Something that we can have in the background to fill in the gaps when we need it."

Thomas walked over to the end table and grabbed a remote. He pushed a handful of buttons and before I knew it, a movie was on the tv.

I walked over to the couch and sat down. When he looked over to me, I patted the cushion next to me, indicating he should join me. He took a deep breath and walked over to sit next to me.

As soon as he sat down, I pulled him in for a kiss. His slightly increased confidence was leading to better technique. I placed his hand on my bare leg and he jumped a little and broke the kiss. Still very close, I whispered to him, "Thomas, I am going to touch you, and I want you to touch me."

Our kissing resumed and he started to rub my leg. I eventually put my hand on his leg and soon after moved up to his groin. He jumped a little again, as I grazed his manhood. He completely pulled away when I gripped his cock.

"What's wrong?" I asked.

"I uhh... I... Ummm..."

"Spit it out Thomas. What is it? Do you not want me to touch you there?"

"Quite the opposite. I want you to. But I am so turned on right now, I might prematurely explode if you touch me there."

"I see. Why don't we fix that?"

"How are you going to fix that?"

I slid off the couch and in between his legs. As I started to unbutton his slacks, I replied, "I know exactly what you need."

He looked slightly panicked. "What is that?"

I started pulling his slacks and underwear down. "Lift up."