CEO Meets His New Intern

Introduction

As CEO of the second biggest group of companies in the United States, William Anthony was one of the most powerful and richest men in the world.

Jessica had seen him on TV and had become rather obsessed by him. Bought up in a wealthy family she wanted to achieve great things her. Leaving college she decided that an internship in Mr. Anthony's group would be the best way to pursue her ambitions.

Chapter One

"I have your briefing papers for your early morning meeting Mr. Anthony."

"Thank you eh.... eh"

"Jessica, Mr. Anthony. Shall I put them down over here? You look absolutely exhausted can I offer you a shoulder massage?"

Jessica was amazed at how direct she had been when talking to someone she thought of as almost god like.

"I am sure that your duties as an intern do not include massaging anyone Jessica."

"No Sir but I am a fully trained masseur and would be happy use my skills on you. I am told that I have a real talent for it and not only massaging shoulders."

She was feeling completely overwhelmed by the charismatic boss and her nerves had made her act much more forward than she would have expected. She was afraid that she might have completely blown any chase of meeting him again when he said,

"Men in my position in the past would have had you publicly whipped for such comments young lady."

Just when she was afraid that she would just get out of his office as soon as possible a smile crossed his face softening his whole demeanor. She knew she was in a bit of a hole but she couldn't resist digging further.

"I might have enjoyed it if it were you doing the whipping Mr. Anthony."

"Now that is enough, or rather much too much. You are barely more than a child and talk like that could get you in serious trouble."

"I am 22 years old and very capable of looking after myself Sir. For my age I have a very wide span of interests and great experience in many things."

"Well you do not have experience of massaging CEOs and by the time you are my age you will look back and realize that the 22 year old you has very little experience of many things. Do you have a boyfriend Jessica?"

"Yes Mr. Anthony he is actually my fiancé."

"Good if you want my advice I suggest that when you next see him you find something you have never done and try it. Now please go home before I change my mind and put you over my knee Jessica."

"Yes Mr. Anthony I will take that as an order although your knee also sounds very tempting Sir."

As she closed the door behind her they both realized that the meeting had left them intrigued and strangely aroused. It was not until two days later that Jessica again delivered papers to the CEO's office.

"Oh it's Jessica isn't it? Please put the papers over here. Well did you follow my orders and if so please tell me what the outcome was?"

Jessica instantly went bright red from her forehead to below the low-cut front of her old-fashioned and rather frilly dress.

"I take it from that reaction that you did indeed follow my orders. Please tell."

"I wasn't sure what to suggest to my fiancé as we have tried most things together. There was one thing that he had pestered me about for months and it was, well, an order wasn't it Sir?"

"Well if you say so Jessica. It was certainly the way you took my advice. So tell me Jessica what did you do to follow my orders?"

"It is embarrassing Mr. Anthony. I am not sure how to say it Sir?"

"You are now behaving more like a child than an experience woman of the world. If you do not wish to tell me that is up to you."

"I let him. I let him take me in the bottom Sir."

"There that was not difficult to say was it Jessica, even if it was rather childishly worded. The more important question was did you enjoy it?"

"I couldn't believe how quickly, how quickly I got aroused. It did hurt but it was also very exciting. Pete was delighted as he said he had never seen me have such a powerful orgasm before."

"Why do you think that you responded as you did Jessica?"

"It was you Sir."

"Was it because you were following my orders?"

"Well yes kind of but more because I thought of you. I imagined that it was you buried in my bottom and I lost all control. Now I do feel like a child and so embarrassed I had better go. It would have been less embarrassing if you had taken me over your knee instead."

"Well no harm done, you have a happy fiancé, you have followed orders and you have experienced something new and exciting. Maybe I should give you more advice or if you prefer more orders."

"Would I still have the option of going over your knees Mr. Anthony?"

"No Jessica but my advice would be that next time you see your fiancé you admit to thinking about someone else while he fucked your ass. Then you could suggest that he takes you over his knee as punishment."

"I know he would love the punishment bit but he might struggle with knowing that I had fantasized."

"A little bit of jealousy can sometimes add spice to a relationship. Trust me I have plenty of experience of it. Now go home and next time we meet you can tell me how it went."

This particular intern intrigued the CEO. He ensured that it was her that delivered his papers the next evening. He welcomed her into his huge office and told her where to leave the papers. He could not wait any longer when he asked her.

"So how did your finance enjoy you following your orders? I take it you did follow orders Jessica?"

"I will always follow your orders Sir. He said he did not understand what was getting into me recently. I said not as much as I would like, which fortunately he did not understand. He did love giving me the spanking almost as much as I enjoyed receiving it."

"Did you admit that you had fantasized?"

"Yes that is how I got him to spank me. I told him I had orgasmic strongly because I was fantasizing about you."

"You cannot tell him anything about me."

"Don't worry Sir he laughed at me and said that you were far too important for me to even fantasize about. It almost gave me the permission to imagine that it was your hand bringing the heat to my bottom. That heat nearly brought me to climax but it did fall just short. My bottom was hot and red and when I looked this morning it was still red."

"I am sure it looks just wonderful Jessica. I would love to see whether he gave it the attention it deserves but I don't think that would be very appropriate."

Jessica faced the CEO and held his stare with her eyes. With her hands she took the hem of her full dress on each side and pulled it up until everything below her bellybutton was uncovered. She was wearing black stockings held up by the belt that was under her black panties.

"I don't think I have been very appropriate with my boyfriend the last few days. Being inappropriate has been great fun and I think this could be even more fun. Unless you give me a direct order I am going to turn round and drop my panties."

She held his stare for only a couple of seconds before turning round. She now took her time lowering her full panties over her large bottom in three teasing movements. She knew she had a very big bottom and was slightly worried about his reaction.

"My god Jessica that is one of the most stunning view I have ever had. I would not have been as lenient on you as your fiancé obviously was. You would have been struggling to sit down today. As it is your bottom is pale compared to how red and flushed your wet pussy looks. Please open your legs a little wider and hold your position. My goodness you are really are wet aren't Jessica? What has caused that young lady?"

"I am sorry Mr. Anthony I cannot help it. Every time I get close to you like this I cannot help fantasizing. When I do I get uncontrollably aroused just as I am now."

"What have you been fantasizing about since you came in today?"

"It is really embarrassing but I was imagining that it was you not my boyfriend spanking me yesterday. You were spanking me really hard and when you finished spanking me you bent me over and took me from behind. I love it when you give me orders but I would love it even more right now if you just took me from behind just like my fantasy."

"I am not going to fuck you Jessica but if you want a prick I can find one for you."

"No I don't want anybody else's cock in me I want yours."

"Don't worry no one else is coming in here. Go to my briefcase over there and you will find something of interest."

Still holding her dress up above her waist she opened the briefcase and found two very lifelike rubber-looking dildos. One was huge and the other probably a little smaller than her fiancé. Even as aroused as she was she decided that the big one would be painful.

"What do you want me to do with it Sir?"

"Well cooking an omelets with it might prove tricky but I do have another idea."

Taking it from her he stuck it on the side of his desk, using the suction pad at its base, so it stuck out horizontally.

"I don't think you will need any lubrication when you back up onto will you Jessica? Before I introduce you more formally to our little friend you can put your other red lips around a real prick."

He moved his chair round and moved her so that she was aware of the dildo behind her but had her hands on the arms of his chair. He was naked from the waist down in seconds and his prick was fully erect.

"Stand up and remove the rest of your clothes so that I have something to play with as you entertain me. Oh I was afraid that your nipples might look rather small on your very ample boobs but no they are magnificent and so erect."

"Thank you Sir they do get very sensitive when I am aroused. I do get very aroused when I take my boyfriend's cock in my mouth and yours looks beautiful."

"I need to make a short phone call. While I do so please be very quiet. It should be easy, as you will have your mouth full. I am going to move my chair towards the desk. When my little toy is fully engaged you may begin. When I move my chair back I suggest you maintain contact with the real cock rather than the rubber one. You may get excited but you will not orgasm. Trust me if you do you will not enjoy your punishment."

"May I bring you to orgasm Sir?"

"You are only required to stimulate me to the best of your abilities. If you do that well you have nothing to worry about. Now use your mouth only for my pleasure."

His cock was deep in her mouth as he reached past her for the phone. She was incredibly excited to have HIS cock in her mouth, she was incredibly excited by fucking the dildo deep in her pussy but she tried to hear what he was saying.

"Yes I have a lot in my lap at the moment..... oh lots of staffing issues but I am getting to the bottom of this training....... staff discipline is such a problem.... my head of entertainment is so sensitive right now....... I am sure it will all come to a climax very soon......these things nearly always have a happy ending."

Looking down into the intern's eyes he saw panic. She was rhythmically fucking the dildo while working really hard on his rock-hard cock. She was good, very good but he didn't want her to cum yet. He backed his chair away from the desk. Her look changed from panic to confused as she followed his prick rather than the dildo. He thought he heard the dildo as it flopped out of her pussy. He sat back and played even more firmly with her huge, hard nipples.

The look in her eyes was now one of desperation and need. He loved the control he now felt over the stunning young intern. He eased his chair towards the desk and her eyes lost focus as she impaled herself again. He felt her change in breathing along the length of his warm wet prick. He was tempted to turn her round and sink into her squelching pussy. She again struck a rhythm fucking herself deeply and firmly. She attempted to keep eye contact with him at all times but did struggle when once again she started to panic.

"This time I am not going to help you control yourself Jessica. Carry on fucking the dildo but do not climax. When you feel me start to cum and only then you will cum very hard."

She confirmed she understood using just her eyes. He loved watching her struggle to contain her arousal. He knew she would fail if he wished her to but was happy when his own excitement was such that he could simply sit back and let her take him over the edge. He gave her no warning before he squirted deep in her mouth. Her surprised look was cut very short as her body was at last able to obey his orders and explode.

His cock was shrinking long before she slowed her fucking of the dildo. She had struggled to keep his prick in her mouth as her body spasmed violently until it finally slumped, defeated and deeply satisfied.

"My god that was like no orgasm I have ever had before Sir. It was as if my brain was being fucked as well as my pussy."

"I think you liked having the control taken away. You clearly have a submissive streak young lady. Did you enjoy trying to suppress your orgasm?"

"I loved it and I loved the fact that I managed to hold out as you ordered. My body was at a level of arousal I have never been able to maintain for more than a few seconds. It made the release and relief afterwards breathtaking."

"So you think you are now able to control your arousal do you? If you do I would be happy to set you a challenge."

"Anything Sir, anything."

"Ok. I will set you a challenge in a few days time. You will prepare for the challenge by playing with yourself each night while sucking your fiancé off. You will not orgasm yourself, but feel free to fake it if it makes your fiancé happier. Now you will not see me until I summons you and I will set the challenge then."

Jessica could think of nothing else for the following days. She sucked her boyfriend off every night much to his surprised delight. It was five days later that she was told to report to his office at 2.30 in the afternoon. This surprised her as the weekly meeting with his senior advisors was scheduled for 3.00pm. She got worried that in some way he was going to make her embarrassed or humiliate her.

When she arrived in the office he was sitting behind his desk alone in the room. Seeing this helped relax her a little but did nothing to reduce her excitement. He waved her to stand beside his chair. He put one hand under her dress just above her knee.

"Jessica I have a challenge for you that is really tough. You do not have to accept the challenge but once you have you will have little option than to see it through. Do you wish to accept the challenge?"

"What is the challenge Sir? I will do whatever you order me to."

"I will not tell you what the challenge is and I am not ordering you to do anything. You must decide and let me know your answer immediately."

"I accept any challenge that you wish to set me Sir."

"I will now tell you what you must do. You will go to my briefcase and bring the toy inside over to the chair over there. You will place the toy on the seat using the suction pad so that you can then impale yourself on it. You will remove your panties before taking up position with the toy fully inserted in your pussy. You will attend the meeting at 3.00pm and not move from the seat. We do on occasions allow interns to observe these meetings. You will not speak and my advisors will at most acknowledge your existence. You will endeavor not to show your arousal but you may increase this as you wish by moving."

She was shocked by the challenge but never thought to question him. She expected to see the dildo from the other day but found the larger one she had previously rejected. Saying nothing she approached the chair and worked out where she needed to place it. She knew her pussy was wet but the dildo was huge and she was concerned about lubrication. Not wanting to make a fuss she slipped off her panties lubricated the dildo with spit and lowered herself onto the huge phallus.

She had to work herself onto it gradually but having taken the first six or seven inches knew she could take the girth. She was still adjusting as the door swung open and the Chief of Staff walked in. She let herself go and the last few inches punched their way painfully into her.

The CoS barely noticed her and addressed the CEO. The room filled up quickly and she was able to try and settle the dildo deep inside her. She had lubricated quickly but the toy was bigger than anything she had ever seen let alone been penetrated by.

The meeting was surprisingly boring but she was unable to concentrate much on what was being said as what she really wanted was to bounce up and down. She found the most arousing thing was to roll her hips and grind down on the monster. She was soon desperate for the meeting to end, as she was scared that she would loose control and climax. She tried to think of boring things but kept returning to images of the Mr. Anthony fucking her frantically.

Her arousal was building all the time and she was beginning to get even more worried about losing control. How would she hide an orgasm from a room full of mature men? They were paying her little or no attention but she did notice Mr. Anthony give her a wicked smile. It was just before the dildo burst into action. It seemed to both vibrate and stroke even deeper into her defenseless pussy.

She quickly tried to stop herself cumming but also tried to work out how she would hide it if she failed, as she knew she would. She was able to slow the build up down and decided that when it hit she would try and keep her body totally relaxed. She was not going to ride the dildo however hard it was to resist. Looking round the room she saw no one was paying her much attention but the idea of trying to hide an orgasm from all these important people caused her to panic.

Nothing was going to stop it now; she was completely resigned to it. The spasms washed through her body blissfully but lacking the violence of those in her best orgasms. She welcomed the gentleness and the persistence of the vibrations but for the first time in her life wished the orgasm would end. The only way to control her breathing had been to hold her breath. She succeeded in keeping her hips still but her eyes were glazed over all the way through her longest ever climax. She had to breath out while her orgasm allowed her very little control of her body. She had to cough to hide the exhaling and this did attract some attention.

As the last spasms left her body the vibrations also stopped. She relaxed delighted that at the worst she had not made a spectacle of herself.

The meeting finished shortly afterwards and Jessica remained seated and impaled. Mr. Anthony smiled down at her as he approached her. As he dropped his trousers and offered her his semi-erect cock the vibrations in the dildo sprang into life. She had to lean forward to reach his growing erection. This brought the vibrator into direct contact with her clit. It also meant that it's enormous length probed previously un-probed depths. He loved looking down on her struggling body as she fucked herself with complete abandon. His cock responded to the vision in front of him. This was no typical blowjob. Her body was awash with arousal making it difficult to concentrate on his cock. Sensing this he took hold of her head on both sides and gently fucked her mouth.

"I would ask you to not cum until I have finished. I don't think it would make any difference would it?"

His words were all it took for her body to surrender to a spectacular climax. He held her face as still as possible as she rode the dildo so violently he struggled to stay in her mouth. This orgasm was not like the first. The violence of her thrusting on the dildo reflected the violence of her orgasm. She barely noticed as he squirted half a dozen times directly down her throat before allowing her to release his spent cock.