One Year Internship Ch. 16 – Wk 35

Week 35

The weather is amazing this early Spring morning, as I enjoy a morning run on the greenway. I use these opportunities to clear the clutter out of my head and to analyze how things have been going and identify any adjustments. Nicole has expressed to me numerous times the value of reflecting, making changes, and to plan and prepare, and plan and prepare some more.

A pretty significant change has happened to my psyche as a result of a somewhat traumatic experience on New Year's Eve. As it relates to this role, that event was probably rock bottom. What should have been a mostly good experience in a hotel room turned into a four-hour gangbang. While the alcohol made sure I did not remember all the bad things about the event, the toll it took on my body will never leave my memory.

It took more than a week for me to physically recover and get back to normal. But the mental aspect has taken an interesting journey. Shana was a life saver during that week as she cleared my schedule and spent so much time tending to my most immediate needs. The most positive and significant outcome of that process was the establishment of a really strong connection with her. I have come to love her as a respected, commanding, intellectual executive assistant, and as a caring, considerate friend, and as a sexual nymphomaniac. I am not sure where our relationship is going to go or what is going to happen after I am no longer in this role, but for now it is a blessing.

Maybe the more important thing that came out of that experience was a reset of my mindset. I think I had started to sway away from one of the most important lessons that Nicole taught me on day one of this internship. That lesson was to attack every situation aggressively and meaningfully, to strive for the best possible outcome each and every time. The recovery from this bad experience pushed me to understand that I need to be less relaxed about these appointments and to take control of each situation and go for the best possible outcome for me, and for the customer.

As I continue my run, I reflect on the actual events the past several weeks and note that I seem to be driving more aggressively for more extreme results. For example, in my training, I have been going harder at the gym and pushing myself in my runs. I have eclipsed my personal records multiple times in multiple areas over the past two months.

I pushed through the assessment and onboarding of the entire document drive for the product team. Sam was shocked at how much I knew about their product and the questions that I asked. From an Operations perspective, Marsha asked me if I wanted to lead a project, because she thought I was ready. As tempting as it was, I needed to respectfully decline until at least this internship is over. Victor told me a couple weeks ago as we came back from a sales visit, that he thought I was capable to be a lead on the next trip.

As it relates to my sexual appointments, I have been more aggressive there too, taking on more challenging situations, and relishing in the physicality of the experiences. Most of the time, I have been the driver of the events that happen in each appointment, even though it isn't me that schedules them.

I look at my run tracker and notice that I am almost at my turnaround point of my half marathon goal this morning. Time to play my favorite video. It is a hard-core motivational video that talks about making each moment the best of your life. It is energetically expressed by a guy with a deep voice. Add in the background music and I feel like I can do anything, like maybe break another personal time record.

Later that morning, I am on my back on a 7^th floor conference room table, with my legs in the air. A guy named Robert from HR is dripping sweat all over me as he works to bring us both to an orgasm. "Harder! Faster!" I prompt him. He is pounding his above average cock as hard as he can into my squishy pussy.

"Ah Fuck!" he moans, "I am about to cum. Where do you want it?" he asks.

"In my mouth." I reply. Anytime I can avoid cleaning cum out of my pussy, I am going to take it.

Maybe a dozen more thrusts and he pulls out. I am ready and I slide down the table and onto my knees. I have executed this move many times before. He pushes his glistening cock into my mouth just as he explodes. Three or four good shots of nice warm cum fill my mouth and slide down my throat. It is satisfying for both of us.

The conversation is minimal as we both attempt to get cleaned up and presentable. Soon he is gone, and I am heading back down the stairwell to my apartment. One more appointment completed.

As I come around the corner to the door of my apartment, I almost topple Shana who is waiting outside. "Oh, hi. What are you doing outside my apartment?"

She smiles and responds, "I came to see you silly." She raises her hand and shows off a decorated plastic t-shirt bag and adds, "And I brought us lunch."

I open the door to the apartment to let us in and offer, "You could have come in and waited for me."

She heads to the kitchen and replies, "Megan, I want you to feel like your home is your home and that you have privacy."

I give her a smirk. She walks over to me after dropping the food off in the kitchen. "Plus, I don't have access to your apartment remember?"

"That still seems weird to me. That THE Shana wouldn't have access to everything."

"Well, that just goes to show how important Jon thinks the privacy of the intern and their apartment is. Neither he nor I have access to this apartment."

I lean in to kiss her, our tongues gently exploring the other. It is sensual and sweet. I am glad to see her. As she pulls away, she says, "I can taste a little bit of your pussy and some guys cum in your mouth."

I turn a little red. "Yeah, well, I did not have time to get cleaned up from my last appointment obviously."

She kisses me again. As she walks to the kitchen she says, "I like it."

Soon after we are at the table eating. I ask, "Why do you almost always bring Italian?"

"Because it is your favorite remember?"

"Mmmm Hmmm."

"Are you saying I should bring something different?"

I laugh. "Well, if we are going to have lunch together almost every day, we should have some variety."

She returns a laugh. We continue to eat. Finally, she breaks the silence. "Megan, can I ask you to help me with something?"

I look at her intently. Normally she does not ask for help from anyone. "Uh... Of course."

"I am slightly embarrassed to talk about it, but I feel like you and I have a circle of trust, right?"

"Of course, Shana. What is it?"

There was a long pause as I could tell she was building up the courage. The anticipation was almost overwhelming.

"You see, my boyfriend, Brad, and I are celebrating our anniversary this Friday night. He is taking me to dinner at a really nice place that I have wanted to go to forever and all that."

She went silent again as I waited to see what she was going to ask for. A million possibilities ran through my head and none of them made sense to me. The silence lasted so long I had to speak up. "Shana, what is it? You can trust me."

"I want to do anal with him." She blurted out.

I was a little surprised by her comment. "What brought this on?"

She seemed quite bashful and nervous to be having this conversation, but she did continue. "He has asked me a number of times since we have been together, but I have never been willing."

"And you are now? Why?"

"Because now I know someone who has done it and likes it." She was turning red for some reason. I guess this topic was really embarrassing her.

"I don't really understand why that would influence you to want to do it. There are probably a lot of things that I like to do that you would not be interested in."

"Name one!" she sharply responded.

"Uhhh... Well... I was going to say anal, but I guess that is not true." I continued to try to identify something, but was struggling to find anything my new adventurous lover might not be interested in.

"What about a threesome?" I finally asked.

"I would be interested in doing that. I think that is hot."

"With 2 guys or a guy and a girl?"

She paused for a moment. "If I did it with another girl, she would have to be you. I don't think I have any interest in being with any other girl besides you."

"And with two guys?"

"I like the idea of it. It turns me on, thinking about being fucked while I suck on another guy's dick."

"So, you are going to invite another guy along with your boyfriend?"

"Uhh... I don't know. I said it turned me on. Not that I had thought it through."

"I see. So, what about a gangbang? You want to be fucked by three or four or five guys at a time?"

"Megan, when you tell me about it, it turns me on so much. Thinking about being a little fucktoy for a bunch of guys makes me horny and wet. Just talking about it right now makes me want to masturbate."

I smiled at her. Now I was sure there is a little nympho underneath her conservative exterior.

"Okay. Okay. Back to anal with your boyfriend. What do you need from me?"

"I need you to teach me about it and to help me prepare."

"That process is a bit personal. I mean teaching you how to clean your anal passage out. Uh... preparing your backdoor is very personal. It is not quite like me licking your pussy."

"I know. But I trust you. And I am willing to share every square inch of me with you. And I cannot be this vulnerable with anyone else. And I really want to do this with him."

I could see the genuine concern in her face. It melted away any resistance I had. If she wanted it this bad, I would help her. "You said your date night is Friday night? And that is when you want to do this?"

In a very sweet puppy dog look kind of way, she nodded her head.

"Okay. Then I need you here about three hours ahead of when you are leaving for your date. And you need to get ready for your date here and meet your boyfriend at the restaurant."

She nodded.

"That means that you have to block my calendar and reschedule any appointments that might be there right now."

She nodded.

"I will have everything else prepared and ready. Limited meat on Thursday and pretty much liquid calories only on Friday."

She nodded.

I looked at the clock in the kitchen. "I need to get cleaned up for my next appointment. I'll see you on Friday then?"

"You'll see me before that!"

We stood up and met on the other side of the table. We kissed in appreciation of each other and then she thanked me. We separated and then went about what was next for each of us. What an eventful Monday it has been already.

I am basically three quarters of the way through this internship. It has been grueling and rewarding. Thankfully not equal parts. The positives that have come out of the last nine months far outweigh the negatives. I don't let myself think of the finish line just yet. I am still focused on one day at a time, one appointment at a time.

It is now Wednesday late afternoon, and I am getting out of the shower for the third time today. This time I had to clean my ass out and get it ready. In forty-five minutes, I will be in Stella's office for our weekly appointment. She has been my primary mentor this year and also my most challenging executive sexually.

On the 8^th floor, I stop to talk to Seema, one of the executive admins, for a few minutes before Stella is ready for me. She is an interesting person, who has shown no interest in spending 'quality' time with me. It is unfortunate, as I think she would have been a fun partner.

Just then Stella calls me in.

As I come in the door, she points to her couch against the side of her office. This is unusual as we have never spent any time on the couch in the basically nine months, I have been doing this internship. When we do our mentoring sessions, she wants me at her desk. When we fuck... that's right... what Stella and I do is pure physical fucking. When we fuck, we are almost always on her conference table. It is a little bit of a fetish of hers, I think.

I sit at her couch and patiently wait for her to join me. It takes a few minutes and when she finally comes over, she is empty handed. I look at her inquisitively. She sits in the chair next to the table. I recognize her configuration is similar to that of Jon's office and this is where he would sit when we meet.

Once comfortable, Stella starts, "Megan, I am going to be straight with you. From a mentoring perspective, you have far exceeded my expectations and certainly the accomplishments of your predecessors. From a finance perspective, there is nothing else I can teach you unless you wanted to start working in my department."

I showed a little concern on my face. "So, what do we do now?"

"You have a little less than three months left and knowing you, you do not want to be idle. I assume you will still be learning as much as you can and readying yourself for the next steps in your career."

I nodded my agreement, but still had some concern on my face. "I am concerned that means that you are not going to mentor me any longer."

She laughed. "Oh sweety, I am still the primary mentor for this internship and there are still things for me to work with you on. They are just not finance focused any longer."

"Uhhh. Okay. Then what will we work on?"

"Things like preparing you for your college entry process. You are still interested in going to college, aren't you?"

I energetically nodded my agreement.

"And I should be helping you decide whether you want to gain full time employment at Tri-Star and if so, what department you will be going into. You get the idea."

I think my expression softened. Stella tapped me on the leg and said, "Plus, I think you'd miss our fuck sessions if I cut you off."

While I small moment of freedom flashed across my eyes, I boldly replied, "I think YOU would miss our sessions if you cut me off."

She leaned back in her chair and smirked at me. "Maybe. Maybe..."

We shared a laugh. She stood up and went back to her desk to grab her pad and pen, and on the way back commented, "I'd like to get started now. Are you opposed?"

I shook my head no and asked, "Do you want to do it here or at your desk?"

She sat back down and got comfortable. "I am not showing you anything, so I am okay us discussing right here where we can be comfortable. I probably don't use this space in my office enough as it is."

We spent the next half hour walking through what I had left within Tri-Star. The outcome was acknowledging that I had finished all the certifications I could, and had maxed out functional mentoring with Finance, Operations, Legal, and IT. I still had some topics left with Sam and the product teams and in theory, HR would never be done as there is always more to learn about dealing with people and corporate situations.

She finally asked me directly if my intention was to come on full time with the company.

I thought I had more time before I needed to think about this, so it took a moment to respond. Finally, I replied, "I think that is my intention. I have not thought it completely through, but it seems like the overwhelmingly best choice, right?"

"I completely agree. It is the best choice for both the company and for you as both sides have invested so much into this relationship. Assuming that is the case, what function are you leaning towards?"

There it was. I was put on the spot again. I tried to think quickly but was really struggling to come to an answer. Stella eventually interrupted, seeing my difficulty. "You do not have to decide this very moment Megan, and I will not hold you to whatever we talk about right now. I am even okay if you don't choose finance, but I cannot advise you if you are not open to the conversation."

That eased some fears and I felt more comfortable opening up and thinking out loud. We discussed the positives and negatives to each function and where my interests lie. We ended the conversation with Operations slightly in the lead.

We then moved onto discussing college, and what options I had. The local University is one of the top colleges in the country and I found out that many of the executives have relationships with the University and that they could assist in my admissions. She gave me homework to work through a plan, and a schedule for the application.

At some point, after maybe an hour of discussion, she finally cut it off and commented that we would have to continue it next week. She was ready to move onto what was next.

Stella rose and walked back over to her desk and put away her pad and pen. When she walked over to her closet, I knew what I needed to do. I walked over to her conference table and began to get ready. As she headed over to meet me, I noticed she had two buttplugs and two dildos in her hands, along with her strap-on equipment. "I'm feeling very hardcore this evening Megan. I hope you are ready."

I took that moment to clear my mind and repeat a saying that I have been telling myself before every challenging situation. 'You are strong. You are capable. You can handle anything. This situation is here for you to take control. Go out and do it.'

I arrogantly replied to her, "Oh, I am ready. I hope you are ready."

She paused to look at me. Then a semblance of a smile broke through. I knew the battle had begun.

It is a mixed bag with Stella. Her version of romantic has some kissing and some groping, similar to what a man might do. Today, started out less romantic than usual. We quickly took our clothes off and without any kissing or petting, she ordered me to bend over the conference table and spread my legs.

I was a little wet with anticipation and had spent some time warming myself up before coming to this appointment. Stella likes to be rough and a slight bit extreme. Most recently, I have given it back to her just as severe if not more. I feel like I have been more sexual and more extreme in general lately. So, I was prepared for whatever she had planned.

There was a long, almost uncomfortable pause before anything happened. Finally, I felt cold lube being squirted in the crack of my ass and her hand work it thoroughly around both of my wanton holes.

My ass was first to get attention. I felt an object pressed against my sensitive anal bud until it finally gave way and let it enter. I moaned slightly as I recognized it as the smaller of the two buttplugs that I knew so intimately.

Once that was in place, she moved to my pussy. I felt the smaller of the dildos slide a few inches into me. This dildo is average in size and completely smooth. It is what she uses to get me used to penetration before she moves to the bigger equipment.

I enjoyed her fucking me with that dildo and gave her a few noises to show my appreciation, but I knew we were both anxious to move on. After a few solid minutes of that, she pulled the dildo completely out and removed the buttplug as well. I felt more lube drip down my crack.

Pressure soon came back to my ass as I felt her start to work the bigger of the plugs into my tiny hole. It did not take long as I was completely relaxed and ready for the invasion. Over the past several months, I have also come to recognize that Stella is not very patient nor gentle. So, I have gone out of my way to prepare my body and mind before showing up to our appointments.

Stella started to move the plug around in my ass in a circular manner, sending jolts through my body and causing my pussy to throb. My holes were unusually hungry, and I was looking forward to her feeding them soon.

She stopped the motion, and pulled the plug part of the way out, leaving the fat middle stretching my hole. She left it there for a count of seven or eight before she pulled the plug most of the way out, letting my hole partially collapse. I felt some lube being applied before she pushed the plug forward again, stretching me out slowly.