One Year Internship Ch. 09 – Week 01

My conversations with Ashley and with Victor were both stuck in my head. They both seemed so weird. Maybe weird should take on a new definition in this internship. Ashley had asked me to come back to see her this week as I flew past her for my appointment with Stella on my first day. It has taken me some time to get the hang of things and get used to doing what I am doing and where to go. So, fitting in a random conversation around appointments and all the other things I have going on turned out to be a challenge.

Apparently, Ashley got tired of waiting and sent me a meeting invite. I have quickly learned that if I don't set a meeting invite for something, it won't happen. I vaguely remember Nicole telling me that during my onboarding.

Ashley set the invite for Friday morning. By then, I had started to get a handle on most things. I had finally gotten used to the color coding on the calendar. I could glance at an invite and know what it was for. I learned my way around my computer and read through the instructions sheet that explained how to do certain things like book hotel space or to get an apartment cleaned, which I am going to need a lot of as it turns out.

Earlier this week I got my first notification that I had received a tip. When I read the email, it had a message telling me to log in to my account to see the specific details. The tip was from Ralph, a guy in Operations who works for Marsha. I met with him on Tuesday, and he was thanking me for cheering him up after a recent breakup with his girlfriend. Amazing how a sympathetic ear, a blowjob, and some rebound sex can cheer a man up and make him forget his woes.

I logged into my bank account expecting to see the couple thousand I had left in there from my interview bounty. I giggled as I saw another thousand compliments of Ralph. Seeing that tip energized me and powered me through several additional appointments that day and the next.

I was doing quite well until I went on a run of three straight sex appointments with no break yesterday. I was fortunate that none of the guys were particularly big, or rough, but it still took it out of me. I had dinner with Nicole that night and she showed me how to block off time in between to allow for recovery and to clean myself up. Rookie mistake.

Steve set up time with me first thing Friday morning, 7 am. He wanted to see how my week was going and to see if I needed anything. I gave him a wonderful blowjob and swallowed his huge load to show him my appreciation for checking up on me.

This brings me to the meeting with Ashley. I entered the executive area on the 8^th floor a few minutes before 9 am. I stopped by the break room to see if she was in there only to find Beatrice, who told me where to find her.

I zig zagged my way through the hallways passing a few executive offices before I found Ashley toward the back, by Michael and Curt's offices. She was on the phone but indicated it would only be a few minutes. I sat in an open chair against the back wall. I guessed this is where guests for Michael or Curt would sit and wait.

Ashley finished her phone call and told me to follow her. She led me past a few cubes to a tall door against the wall. She flashed her badge to the reader, and it unlocked. At first glance, it appeared to be a storage room, mostly filled with long file cabinets. She confirmed, "This is where our company keeps all of its files that are not digital. I need to do some monthly filing, so I figured you and I could talk while I do it."

I nodded my head and waited. She continued, "I know what your role is with this company. I respect it and understand the value. I am not going to judge you at all. But I need to figure out what our relationship is going to look like."

I replied, "I am a little confused. I think it can look like whatever you want it to look like. You have all the power."

She stopped doing what she was doing to look at me. "I don't want to force you or even unduly influence you. I would like for whatever we do to be because we mutually enjoy it."

"I appreciate that, Ashley. But I am still a bit confused."

She sat on a box and started again, "Let me explain. I am a lesbian. Like full lesbian, no men at all. I have a girlfriend that I live with. We have been together for more than a year. I'd say we are almost as happy as a gay couple could be."

I interjected, "Then why do you want or need anything with me?"

She continued, "I was getting to that. You see, my girlfriend is what most heterosexual people would call butch. She shaves the sides of her head, has multiple piercings and tattoos, prefers to be in jeans over a dress or a skirt. You get the idea. She was my effort to be rebellious and try something that I had never had before."

I was still a bit confused. "But you have been together for more than a year and live together. Something must be going right."

She smiled, "It is. She has this tough exterior but has really been a sweetheart to me. She cares about me tremendously. But I feel like I am missing something I enjoy a lot."

I looked at her with an obviously quizzical look. She added, "I miss the girly part of being with a girl. Does that make sense?"

I paused and tried to grasp what she was wanting. I finally nodded no. "Not exactly," I replied.

She frowned and continued, "Okay. Let me try this. You've been with Stella now a couple times, right?"

I nodded. She continued, "Well, I have been with her a half dozen times. And I didn't really like it that much."

I asked, "Why not?"

"Well, for one thing, I am not into rough sex, especially rough sex with a strap-on. That's not my thing. Secondly, I felt weird being a subordinate of hers and having sex with her."

"I can understand that."

"You understand what I don't like with Stella?"

"Yes."

"And if I state that my wonderful girlfriend is closer to Stella than any other previous relationship or lover I have had, can you see what I might be missing?"

It was starting to come together. I asked, "So what do you want from me then?"

"I want to have a appointment with you, as a trial run, to see if you have what I am looking for. I want us to have something sensual as opposed to overtly sexual. I want to experience what it feels like to be a frilly lesbian again. Can you do that for me?"

My heart rate rose a little bit. I felt the need to share my concerns. "Ashley, can I be honest with you?"

She looked worried. "You don't think I'm attractive and therefore you're not interested?"

"No. That is not it at all. I think you are quite sexy."

Still looking very worried she asked, "Then what is it? You have to like girls if you are doing this role right?"

"Yes of course... Listen... What I wanted to tell you is that I am not sure that I am the right match for you. You are looking for a traditional girl on girl lesbian experience. I don't know anything about that. I have only been with 3 girls and all of those were in the past few weeks. I am not very experienced at all."

She scooted off the box she was sitting on and walked over to me. She looked me in the eyes for a moment before she leaned in and kissed me. It was overly sensual as I felt her body press into me. I reached down and ran my hands along the silky material covering her back.

We kissed for a long time before she finally backed away. She smiled at me and commented, "You are a very good kisser, Megan. You did not rush through it. You did not seem impatient. You did not make it overly sexual by grabbing my ass or anything. Did you enjoy kissing me?"

I smiled at her. "Of course. You are a sexy woman and a good kisser yourself."

"I know you said you have limited experience, but do you enjoy being with another woman?"

"I do. Much like you, I like the sensuality of it."

"Then I think you and I may be a match. I'd like to set up an appointment with you to try it out. You game?"

I smiled, "I am. I'm looking forward to it."

We talked a bit more before I finally went on my way. As I left the small storage room, I considered how odd the scenario seemed to me. I mean, she could have just set up an appointment with me and we could have seen how it went, without all the pre-meeting context. I guess we will see what happens.

After my meeting with Ashley, I grabbed a bottle of water from the break room and met with Victor in his office. I was surprised to get a meeting invite from him that did not include mentoring or sex and that it was supposed to only last 30 minutes. As I walked in, he pointed to his couch as he pulled his desk chair over opposite me.

He began, "Megan, I am very excited that you chose to accept this internship. I think the fact that you experienced what you did with Frank, and Arthur, and me, and still chose to join us is remarkable. We really put you through the wringer."

I replied, "It was quite an experience. A definite first for me."

"And yet you still joined. That tells me something about your grit, about your ambition. You have so much potential that you can't even see right now. I hope you realize it before you lose half the year."

I felt a little bold, so I responded, "So why don't you set up mentoring sessions with me and teach me? Explain to me what I am missing. Help me not lose time."

He looked at me and pondered. Then he smiled and sat back in his chair. He replied, "I am not much of a mentor Megan."

"How about I make it worth your while? You mentor me in sales and the right approach and how to be incredibly successful in supporting your efforts on the road. And in return, I will not only suck and fuck you during every mentoring session, but I will make it a point to join you on regular sales calls and we will go make a bunch of money together."

His smile was so large, I could see his full set of teeth glowing back at me. "Now that is an incentive if I have ever seen one. I will get us started next week."

I started to get up when Victor told me to stay. He continued, "That is not why I set this meeting up. I actually have a request for you."

I sat back down. "Okay. What is it?"

"I have an account executive in my team that I have been mentoring a little, I guess." I gave him a look based on his stated resistance to it. He recognized my smirk and continued, "Let's just say I have been pushing him to get better at selling. Anyway, he just hit a really big milestone and I want to reward him."

I was nervous about where I thought this was going.

"His name is Carlton. He has been with us since we acquired the company he was working for 5 years ago. He has struggled to continue to progress as a sales executive, but somehow, I have a soft spot for him. He has continued to be humble and take direction and work hard to get better. And now I want to reward him for finally landing a big deal mostly by himself."

"And you want to reward him by hooking up with me?"

"Exactly."

I sighed, "And what do you want me to do."

"I am sure you guys will work it out. It doesn't seem that the guy has much adventure in his life."

"And where would I meet him and when?"

"Tomorrow sometime for a couple of hours; maybe you can book one of the apartments on the 5^th floor to be more comfortable."

"You aren't going to surprise me and have a group of guys there to gangbang me, are you?"

Victor laughed, "No Megan. That was a one-time set up. I will never consciously set you up for an event like that. I'm not saying something like that might not occur on a sales trip, but I would not choose it for you."

That gave me a little comfort. I replied, "I see."

"Listen, just give the guy a good time and I will make sure you get a solid tip for Saturday and of course it would go a long way towards your first monthly bonus."

He knew how to entice me with money. "Okay. Tell him to send me an invite and I will book Apartment 2."

"Excellent. That is all I had for you today."

I was surprised that he did not want to do anything sexual. But I remember Nicole telling me that if I can get away with not doing anything sexual, take advantage of it. Don't kick a gift horse in the mouth they say. So, I did not say anything, and we parted ways and I went about my schedule.

I had a few more appointments and a training session to do before I was to meet with Jon at the end of the day.

Just before 5:30, I got a call on my cell phone from a number I did not recognize. Thinking it could be someone important from my new job, I answered it. "Hello, this is Megan."

"Hi Megan, it's Jon." I recognized his voice right away.

"Hi Jon. What's up? Please tell me you are not calling to cancel our meeting?"

Jon laughed, "Quite the contrary. I was calling to let you know that I finished early if you are ready, you could come to my office now."

"That's great. I will be there in a couple minutes."

I was grateful that I had already cleaned up from my last appointment and had been doing a self-paced training module. I grabbed my little purse and headed for the elevator. A couple minutes later I was tapping on his office door.

I entered his office and he directed me over to his couch. His office was larger than the ones I had seen to this point. It had a couch, a coffee table, and two nice chairs off to the right, like Matt's. He had a nice set of bookshelves off to the left like the others. But his office had room for a conference table and chairs like Stella, a wet bar, and a handful of other amenities. He also had a huge set of windows that covered the entire far wall.

He broke my gaze when he sat down in one of the chairs and started the conversation. "So how has your first week been?"

"I think it has been okay. I really don't have anything to compare it to."

He laughed, "I'm sure you don't. Well, tell me something that happened this week that you liked a lot."

"I think the apartment is amazing. I have really enjoyed having my own space, and after a busy day it has been nice to have the peace and quiet."

"So have your days been really busy?"

"I have had around 5-6 appointments a day, plus training sessions."

"So, you have been able to do some training already?"

"I have. I got some direction from Stella and from Nicole."

"I think training is super important as is mentoring. Have you had any mentoring sessions yet?"

"I had a mentoring session with Stella on Monday but that has been it so far."

He got up and walked over to his desk and typed something into his computer. He returned in a few minutes and sat back down. "I have asked my staff to make time to mentor you. I know it is just the first week, but I want to remind them of this request. I can ask the executive admins to come up with a schedule for you. I do not want you to be overwhelmed with a 2--3-hour session every day."

"Thank you. I appreciate that."

"Tell me one thing that happened this week that you did not like."

"Well, it isn't so much something that happened, but rather something that did not happen."

"Okay. What was that?"

"I did not get in a bit of exercise... Well... outside of having sex of course."

Jon laughed. "I see. I will assume as soon as you get used to the schedule and how you can control your own calendar you will get that remedied."

"I hope so. I feel a little lost, not working out or at least running."

"If you like to run, there is a greenway about half mile south of this building."

"Really? I didn't know that. I'll have to check it out."

"Have you been taking advantage of the other perks that come with your role, like the chef?"

"Yes indeed. It has been a god send. I am not up to par to cook and even if I was, it is not like I can go grocery shopping."

"If there is anything you need. Clothes, groceries, electronics, whatever, you order it. Steve will approve it and you will have it. I do not want you to be without anything you need to be successful and happy in this role. Do you understand?"

I nodded my head.

"Last question. Now that you have been here for the good part of 5 days, do you regret making this decision?"

I smiled. "Not at all."

"Good. Well, if you noticed I planned a long session for us this evening. I have some mentoring I want to do with you, and I am very interested in giving you an opportunity to make progress on your unofficial official goal."

I smiled as I thought about this goal for me to take his huge cock all the way inside each of my holes before the year is done. The thought made my pussy tingle. I smiled at him and said, "I am ready when you are."

Jon stood up and walked over to the couch, unbuttoned his slacks and dropped them to the floor. My mouth watered in anticipation as his boxers soon joined his slacks by his ankles. His thick limp cock hung below the ends of his dress shirt.

He unbuttoned the first few buttons and then slipped both shirts over his head exposing himself completely. I hesitated, slightly intimidated by his hefty tool hanging inches from my face. Even soft his cock was large and demanding.

Jon reached down and gripped his limp unit and aimed it at my mouth. He slowly rubbed the mushroom head over my lips. I closed my eyes and concentrated on the softness of his skin and the smell of his manhood. Finally, I parted my lips and he pushed himself into my mouth. Even limp I had to open wide to accommodate his girth.

I pulled his manhood as far as I could into my mouth and sucked on him gently. It was not long before I felt him grow and stiffen in my mouth. I hummed as I moved up and down his monster rod. It was glorious and I was getting more turned on by the second.

After several minutes of me pleasuring him, he pulled himself out of my mouth. I opened my eyes and saw his glistening cock mere inches away from my face. I reached out to grip it. I needed both hands to hold it. The enormity of it still shocked me, even after having it in my hands and mouth twice now. It was the most beautiful sexual organ I had ever seen.

He broke the spell when he commented, "I want to taste you. Come up here."

I looked up at him as I rose. He took my face in his hands and leaned down and kissed me. His tongue explored me gently; he was a fantastic kisser. I felt him unbuttoning my blouse. I started working on my skirt. Our kiss paused long enough for us to finish undressing.

With our clothes on the floor, Jon leaned back in and kissed me again. It was more aggressive this time. I felt my body getting warmer by the second. He broke the kiss and eased me down onto his leather couch. His body parted my legs.

I felt his warm breath as he kissed my neck and chest, his hands gripping my bare breasts. His mouth continued to move reaching my left nipple. It firmed up inside his mouth. He soon moved over to the other one. He left me wanting more when he finally moved down my flat stomach. I felt his hot breath over my belly button as he left a trail of sweet kisses down my pubic bone.

My pussy was very wet in anticipation. I was quickly becoming intoxicated by this powerful man I barely knew. A tingle shot through my body when he kissed the inside of my thigh inches from my wetness. Another fired when he kissed the other side. I could feel my juices flowing down my cheeks.

Jon intently ran his tongue up my gash causing me to slightly jerk. There was a small pause before he did it again. A strong warmth started to fester in my groin. He ran his tongue up again this time gently brushing my clit. This teasing, however brief it was to be, was driving me crazy. Thankfully he settled in soon after.

Jon explored every millimeter of my tiny pussy. He brought me close to an orgasm before moving to a different place. He pulled my clit into his mouth and flicked it with his tongue several times before backing off. Then he would push his tongue into my tasty hole and drive it in and out before pulling away and licking up my slit. His variety kept me on edge for what seemed like forever before he gave in to finish me off.