Nancy and Her Boss

Other stories in this series

Nancy Remembers Chap. 1

Nancy Remembers Chap. 2

Nancy Remembers Chap. 3

Then the following are separate but related stories and may be read without regard to sequence.

Nancy and the Guard

Nancy visits the Poop Deck

Nancy and her Observer

Nancy and her Boss Part 1

Nancy and her Boss Part 2

Nancy and her Boss - The Weekend

Nancy and her Son

*

Nancy had been called into her boss's office for her rather smutty dress at work and told that she could lose her job. Her boss discovered she was under the control of a BDSM master and was making her dress and act sluttish to humiliate and stimulate her. Her boss, who secretly had admired her ever since she became his assistant, asks if she wants his help to keep her job and get out of this disgraceful lifestyle she got involved with. She spent all of Sunday afternoon with him revealing her recent sexual activities and why she felt so aroused by it. She had found out something she had never suspected in all the years she worked around and for him – that her boss was into BDSM himself. After a nice Sunday afternoon tryst they decided to work after hours on a way to resolve her problem with the minimum of consequences to her.

Monday morning she dragged into work, still a little hung over from last nights activities at the bachelor party her son had set her up with. In her new office attire she put her purse in her desk and headed for her boss's office. No sign of her boss so she opened his middle desk drawer and got the keys for the conference room and the storage room.

Closing and locking the conference room behind her she opened the storage room. She felt foolish doing this but she also felt excited about it, she moved to the envelope containing the clit stimulator and removed it from the envelope. She lifted her skirt and sat on a chair so she could spread her legs wide, so wide in fact that her lips spread open making it easy for her to take hold of her clit. Her hand lingered as her fingers took hold of her clit and squeezed it a little. A moan escaped her mouth letting her know that even as tired and bad as she felt this was a pleasurable thing. Playing with her clit a little she got aroused before she realized the objective wasn't to make her sluttish twat feel good, it was to put the clit vibrator on so her boss could summon her when he desired.

A fleeting thought ran through her mind that she hoped he summoned her many times a day – whether it be for her to pleasure him or to have her do some office work. She was a little disappointed that the remote wasn't with the vibrator because she would have enjoyed a little test of the toy before going to work. She realized she had been gone from her desk long enough and that she better get back to work. She let her dress fall covering her naked pussy and thought how strange the dress he required compared to what the mystery man had made her wear. Her new dress fell to about 3 inches below her knees compared to the skirt she wore Friday that was about 3 inches below her crotch.

She sat at her desk thinking how wonderful if her boss could become her new Master and lover. He seemed very interested in maintaining a professional image at work and in public but had a very erotic and randy attitude when in private or where others who had no idea who you were or anything about your special kink and she liked that idea. She liked the humiliation and exhibitionism but not when people you worked with or close friends were involved. She felt that with him she could and would go naked if he wanted it because he would never allow her to do it where it could cause her any harm. This was in absolute contrast to her mystery men, who made her take lots of risks and expose her almost all the time. She was beginning to fall for her boss's way of doing things. She knew she would get cock when she needed it but in a safe manner. She knew she would get spanked and whipped a lot but not so it would endanger her public image. She knew she wanted her boss to turn on the vibrator demanding her presence. Just as she had all these thought in her mind the clit vibrator went off.

Nancy stood up from her desk, the vibrator causing her a little bit of arousal and lots of difficulty standing, she proceeded into her boss's office. Looking at him behind his desk she smiled and said good morning. The clit vibrator had her aroused enough to want to go to his side and suck his cock but as she advanced the vibrator stopped. "Good morning sir," she addressed him formally.

"Good morning Nancy," he replied. "I see you have done everything we discussed yesterday but why do you look so tired?" he asked.

"I was out late last night at one of the parties my son organized." She responded, not daring to tell him the whole story of the party. Like the fact that it was a bachelor party and she was the center of attraction. Or that she had gotten smashed and fucked or sucked every guy there, or that she was tied and whipped at her request. This was a little more than she was ready to tell him.

"Are you going to be able to work an hour or so after hours? If you're too tired we can wait a day but not too long or your problem may not be so easy to resolve." He looked at her questioningly.

"Tonight is not a problem for me and I look forward to working this out," she replied, looking into his eyes just knowing that she would do anything he asked.

"Okay, that will be all Nancy," he said in a very professional voice that let her know she was dismissed.

Returning to her desk she engaged in her normal office busy work that occupied her until it was time for the morning mailroom run. As she worked she was thinking – no hoping – that he would find some reason to start her clit vibrator. She began to realize her observer was looking her way with a puzzled look. She knew he was looking for her short skirt and her normal masturbation show under her desk. How was she going to tell him that was a thing of the past; she already missed putting on the show for the hidden camera. She couldn't very well just wander over to his desk and discuss this matter with him but she knew she owed him an explanation.

She got up from her desk and headed off to the mailroom, as was her normal routine. What wasn't normal routine was that she made sure she took the long way to the mailroom so she would be sure to walk by her boss' door, hoping that he might ask her to do something or at least acknowledge her presence. It frustrated her that she was going to be his nighttime slut but be ignored all day long at work. Of course there was the fact that if he needed something he would turn her clit vibrator on to summon her, she kept hoping that she might be summoned frequently but just knew he was too professional to do that at work.

When she arrived back at her desk she found a manila envelope with a question mark written on it. She glanced at her boss' door, sat down and opened the sealed envelope. Her mind told her it had to be from her observer and that was confirmed when she read the note within. The note simply read, 'the camera is rolling, what happened?' She knew he wanted some sort of explanation but she couldn't be seen hovering over his desk whispering any kind of lengthy explanation. Putting the note in her desk she scrawled out a note to him, saying 'things have changed, will email you late tonight', placing the note back in the manila envelope. She waived the manila envelop at him until she caught his attention and then placed it on the edge of her desk.

Nancy returned to her work, answering emails, printing and filing documents and such. She almost missed him as he passed by her desk and retrieved her note but his being so close to her gave her a nervous feeling, goose bumps ran up her spine as he walked off. It was too easy for her boss to see anyone stopping at her desk like that and she didn't want any more of this mess she was in coming out.

Her phone rang so she answered, "D & R Pharmaceuticals, this is Nancy, how may I help you?"

"On your way out to lunch please stop by my desk and bring that little note you got with you. I will expect a short explanation too," her boss said. As she sat shocked at his commanding voice she knew all too well that he had seen the note put on her desk and that her observer picked up a response.

"Yes sir," was all she could say. He hung up the phone so she did the same. The rest of the morning dragged on as she thought what to tell him. Most of all she knew, no matter what she told him, it would come out that she failed to tell him about everything involved in her life since the mystery man took control of her. She felt bad about it, disappointing and deceiving him was not something she wanted to do. He was a very caring person and a very dominant man. He wanted her in his life, now that he discovered her love of bdsm, and she wanted him plus she felt safe with him – why then did she hide so much from him? It wasn't the punishment she would receive over this, and she knew she deserved punishment, but the humiliation of telling him there was more involved in this mess that she hadn't told him about.

Finally lunchtime arrived, she picked up her purse and turned to head into his office. She paused, opened her drawer to retrieve the note and then walked on shaky legs toward his office door. At the door she paused for a moment, note in hand, and waited. It seemed like a long time but after a few moments he motioned for her to come to his desk. Reaching out for the note she handed it to him and stood quietly while he read it.

Glancing up at her he said, "this has more to do with your problem and lifestyle change doesn't it?"

"Yes sir, but I can explain," she began but was cut off by her boss' response.

"Not here, not now. We will discuss this later but you need to recognize that your failure to tell me everything may affect the solution I had come up with. Now we have new players in the situation so I don't know how that will affect the final outcome. I am disappointed in you Nancy and we will discuss this, in detail, further but right now you go to lunch." His voice was firm, his command clear and she knew she had been dismissed with nothing further to be said.

Nancy left for lunch feeling … well she didn't know how she felt. Humiliated, yes, but also ashamed that she had disappointed him and yet she felt there were things she shouldn't have to disclose – private things. She went to the cafeteria but couldn't bring herself to eat, she was upset with herself, her situation, her emotions and her body. She was on her way back from lunch when her clit vibrator started, she felt the stimulation begin and quickly spread from her clit to her nipples. By the time she arrived at her desk her nipples were so erect they were as painful as if she had nipple clamps on. Her body was going into overdrive producing juices that started running down her inner thighs.

She reached the office door and had to grasp the doorframe to keep her knees from buckling, "Yes sir," was all she could gasp out. She felt climax approaching rapidly.

Standing at the doorway, still grasping the doorframe, she began to climax. "Ahhh .. I'm ahhh.." when as suddenly as it had begun the vibrator quit. Almost collapsing she leaned into the doorframe and stood panting. "I got here as quickly as I could. That was driving me crazy. I almost .."

"I noticed," he said with an almost sadistic smile. That was the closest to a smile she had seen on his face as long as she had known him. "Come in and have a seat."

As she entered the office and sat down in the chair in front of his desk he continued, "Nancy I am going to say what is on my mind and I don't want you to interrupt at all. If I ask you a question you are to answer the question and nothing more. Do you understand?"

She nodded her understanding but there was a pause, a long pause, with him staring into her eyes the whole time. Finally she realized he was waiting for a verbal answer, "Yes sir."

"Nancy, for the first time in twenty years on the job I find myself breaking the one rule that business and only business be done during working hours. This is a business hour and yet I find it necessary to talk to you about personal life and I don't like it. I was angry, I was disappointed, I was confused and a lot of other things when you brought me the note passing between you and Joe. I was disappointed because the note showed me there is more to your situation other than the guard and your mystery man but yet you told me that you had revealed everything related to your predicament. I was disappointed because I thought I had your trust and devotion. I was confused because you should know if you want my help getting out of this predicament that you have to help me by telling me everything. That is why, when I read the note, I dismissed you. I don't like to talk about things when I am angry so I needed time to think things over. Now is not a good time to be talking about it – during business hours – but it is something I can't get off my mind."

He continued, "Nancy, I told you yesterday that I have feelings for you and always have but they became quite intense when I discovered you enjoyed the same kinks I have. You seemed to indicate that you had feelings for me also and I believed you." He paused for a moment but she realized he hadn't ended on a question but rather a statement so he wasn't waiting for her to answer.

Finally the pause ended with, "Regardless of how it works out between us I want you to know that I will do my best to help you out of your current predicament. I respect you too much to see you ruin your life, loose your job and the respect of your friends and neighbors because you enjoy sex and have hooked up with the wrong teacher/Master. You should be able to enjoy the bdsm lifestyle without anyone outside of the bdsm world knowing your special interests." This was followed by another long pause but again she realized there was nothing for her to say.

Again he began, "now I want an honest and truthful response to these next few questions."

"First question. Nancy do you want my help resolving this problem with as little damage to you or your family and friends as possible?"

She felt a knot begin in her stomach as she knew it was time to answer, "Oh .. ahhh .. Yes Sir." She finally stammered.

"Second question. You do understand for me to come up with the best solution to this problem I need to know everything, and I mean everything, that has to do with your recent experience of personal sexuality, don't you?" He stared at her eyes, looking at the sparkle waiver as he asked the question.

Again she stammered and hesitated in her answer, "Yes Sir. But .. ah I ah just ah don't want to reveal how smutty I can get. It is degrading for me to have to admit some of the things I have done or been forced to do, some of which a common whore wouldn't even do. I don't want to fail you but I am so afraid that if I tell you everything you won't want me anymore."

"Wow!" he exclaimed. "We will leave most of that for a discussion later but for now you just need to know there is nothing you can tell me that would make you less desirable to me, nothing. Now on to the third question."

"Nancy, I don't want you to answer this question until after work but I want you to sit at your desk and think about what it means and if you truly want this. Last night you said you had, and have for a long time, had feelings for me and that you would like for me to become your new Master. This means you would be trained by me to be able to walk proudly in a society that thinks of our lifestyle as kinky and perverted, wearing a collar that signifies your devotion to our lifestyle, yet not a one of them would recognize this symbol as anything unusual. This means that I would be the one making sure you are well satisfied in the lifestyle but appeared to all others as the kind, generous and wonderful person that I know you to be. Can you accept me as that Master?" He concluded with, "Don't try to answer that now, just think about and we will talk later. Now I want you to go back to your desk and get the rest of your work done while you think about your answer."

Again she felt dismissed. She sat for a moment trying to avoid his gaze but knowing he wanted her to maintain eye contact. After all her mind and her butt were told that more than once yesterday. She managed to put a smile on her face as she arose from the chair to return to her desk. She paused for a moment, looking at him, as if she was about to say something.

His eyes looked into hers and he simply said, "Nancy, desk, now!"

With all kinds of emotion filling her heart she walked to her desk to finish her days work. As she sat down she could feel the tears that had developed in her eyes. Try as she would she had a very hard time concentrating on her work. What would she tell him about her observer, what would she tell him about how she felt about him, what did she want to do about this crazy lifestyle she had entered and most of all what was she discovering about her sexuality. These and other questions made her head spin to the point where she found it impossible to concentrate on her work.

Her concentration on these questions had her in an almost trancelike state, to the point she sat at her desk all afternoon and didn't even notice when all her fellow coworkers began to leave for the day. She continued to think about things for over an hour after everyone left. The first notice of anything strange was when her clit vibrator went off and she got up to see what her boss wanted. As she got out of her chair she noticed there were no employees anywhere to be seen and some of the lights had been turned out for the evening. She glanced at her watch and noticed it was almost 7pm – where had she been – over 2 and a half hours after closing time.

She started to rush to his office but the vibrator was taking its toll. If she moved fast it shot sensations up to her nipples moving her toward a climax, if she moved slowly it made her legs feel weak. She slowly approached his office and moved toward his desk.

Standing in front of his desk she weakly managed to say, "sorry sir, I don't know where the time went." He stopped the vibrator and she felt her body go weak as it relaxed.

"Well I didn't think the question I asked earlier was that difficult to formulate an answer to but I didn't want you sitting at your desk all night. Have you an answer for me?"

"Oh, yes Sir." She began but he held up his hand indicating she wait.

"Tell you what, here is the key to the conference room and the storage room, suppose you go in there and knowing what we are about to talk about, knowing what you have deliberately hidden from me, suppose you go back there and prepare yourself for how and what we will be discussing," he handed her the key.

She felt dismissed again; she realized he was very good at that. As she entered the conference room and headed to the supply room she wondered what she should prepare herself for. What did he think she did, all afternoon at her desk play tiddlywinks? She looked about her in the supply room, a table, a spanking bench, a cross and realized he didn't mean what but how. How was she to prepare herself, was he going to fuck her on the table, was he going to spank her on the bench or was he going to whip her on the cross? How was she supposed to know what he was going to do to her. Then it came to her, he wanted her to decide how he was going to discuss the matter with her. Her mind whirled with the events of the past week – he knew most of the detail so why would he want to fuck her so the table was out, she knew how mad he was about her lying and withholding information so she was sure it had to be the spanking bench or cross. She felt ashamed that she lied and knew she deserved a severe whipping but wasn't sure which place. Standing there she unconsciously unbuttoned her blouse and let it drop to the floor, and then she unzipped the dress and let it slide down. She realized she was now naked and it was up to her where to go – spanking bench or cross. She realized he had every right to be furious with her so she stepped up to the cross and locked her left hand into the cuff, then reached for the other cuff but couldn't fasten it with her right hand alone.