The Boss's Secretarybytantricjim©
I regularly travel to my Head Office back east, usually every four to six weeks. My visits entail meetings with the heads of various departments with who I am in regular contact. The last afternoon is reserved for a meeting with my boss, the President and CEO of the company.
His office arrangement is very traditional and one must go through an outer office guarded by his Executive Secretary in order to meet with him. There have been a number of different ladies occupying that position over the years, invariably efficient and determined women. It is important to keep on the good side of the incumbent.
This story took place during a period when this secretary was a woman in her late forties name of Elizabeth. She perfectly fit the description of what an Executive Secretary should look and act like. Tall and slim, calm and elegant, she exuded control over her domain. One did not challenge her suggestions or instructions.
Elizabeth always wore high heels and black stockings in combination with a business suit. Her makeup was understated and her grooming immaculate. I have always admired strong women and I could barely keep my eyes off of her. Office gossip was that she was divorced and that her private life was very much her own.
She was always kind and helpful to me. If I needed an unscheduled appointment she always managed to fit me in.
I had occasion to attend a Friday afternoon meeting. The meeting took place in the Presidents office and it was almost 7 pm before it was over. Elizabeth was in the outer office as I exited. She made some comment about a late dinner and I jabbered out an invitation for her to join me.
She looked a little stunned by my outburst, paused to read my eyes and said, "How nice of you to ask. Yes I would be pleased to join you. Shall we meet later at The Panda Room? I can call and make a reservation if you like."
The Panda Room was a very high-end restaurant in my hotel. It was a perfect choice for dining with an elegant woman and very appropriate that she had suggested it. I told her that I would wait for her in the lobby and stuffed papers in my brief case and almost ran to my hotel.
I showered and changed to a less formal jacket and tie and went down to wait in the Lobby. Elizabeth had changed from her business suit to a light summer dress but was still in heels sans the black stockings. She smiled warmly and linked her arm through mine. "I'm famished," she said and we walked across the lobby to the restaurant.
I felt like a high school kid on a first date. I am certainly not a sophisticate but am quite comfortable in my own skin on most social occasions. But I was in awe of this lady. I am sure that my chest expanded in pride as we walked across the lobby with her clinging to my arm.
The dinner was relaxed and I became much more comfortable with her and feeling less intimidated. She totally focused on me and her eyes never seemed to leave mine. Our discussions were mostly business related and touched on people and events in the company. We talked very little about our personal lives.
It was all over too soon and I walked her out to catch a taxi without even considering asking her to my room. Just as the hotel attendant opened the cab door, she leaned into me. Her body melted against mine and her soft lips held just that little bit longer in a kiss and whispered, "I enjoyed that very much, thank you, maybe we can do it again soon."
A flash of her bare legs, a little wave and she was gone. I stood there enthralled and wondering why I had not been bolder. I definitely wanted more and was beginning to think that I could have had more.
Back home I thought often and long about her. Her scent seemed to linger in my memory. Until this last dinner date I had never seriously thought about making love to her. But now the thought of her naked under me raced through my mind like a repeating video clip.
Elizabeth called a few weeks later. She asked if I would be able to attend an important meeting. I hastily confirmed that I could and she said that she would make my air and hotel reservations.
I thanked her and said, "Why not make another reservation for the Panda Room." I held my breath waiting for her reply and it came quickly.
Her voice was just a tad less business-like as she replied, "I would love that."
She was all business in the office, striding around the office, locating documents and organizing proceedings. She was lovely to look at.
As I left the office at the end of the day she said in a low voice, "Call me when you get to your room, I have a few things to clear up before I go."
I could barely control my fingers as I dialed her number a little while later.
"Hi Jim, our reservation is for 7:30, I will be at your room in 15 minutes and will change for dinner there."
I was certain that I would be feasting on more than dinner that evening. I secured my stiff cock within my shorts so as not to be too obvious when I opened the door.
She was still in her office suit and carried a small overnight bag. She smiled at me and brushed my cheek with her lips and entered the room, placing the bag on the bed. She turned to me and melted into my arms.
I could feel her breasts, her hips and belly and thighs right to the knees. I ran my hands down her back to her hips, pulling her tight and rubbing my body against hers. We kissed softly at first and then more passionately. I fondled her ass, grinding my cock against her hip.
She took a deep breath and said, "I have been thinking of doing that since I kissed you goodbye last month." She stepped back from me and straightened her suit.
She was once more in control although I realized for the first time that she could lose control on occasion. I was ready to fuck her and fully believed that she wanted it as well.
She smiled, "Let me change now for dinner. First things first you know, I am famished once more."
I had a different idea of what came first but progress is progress and there seemed little doubt that I would have her in bed that night. I watched her open her night bag and remove and hang a dress in the closet. She pulled out black lace panties and bra and, smiling at me, entered the bathroom.
She did not close the door and much as I wanted to watch her strip I could not force myself to peek. I had fantasized for weeks about watching those long black stockings come off.
She returned to the room after fussing around a while wearing only the black bra and mini panties plus heels. She was more soft and slender than she had appeared to be in the business suit. Her tits were on the small side but looked great in the uplift bra. Her hips and ass were nicely rounded.
I could make out the shadow of her bush covering her prominent mound through the sheer lace panties. Her hair was loosened and overall she looked fucking gorgeous. I can assure you that the dinner I wanted was not down in the Panda Room.
She had not yet looked in my direction as she began to pull the dress over her head. "You like?" she said, "I can feel your eyes on me and it excites me. But dinner first." She returned to the bathroom to finish her make-up.
It was obvious that she enjoyed the tease and foreplay, and I was certain that this performance had been planned.
Dinner seemed endless. I could not push the thought of being in her from my mind. She was much more informal during dinner and her eyes were soft and steadily fixed on mine. I had the feeling that I was the only person in her world. She sure as hell held my mind captive.
I asked her how it came about that she was interested in me. We had met only a few times a year over a short period, and our office meetings had never been much more than a pleasant 'hello' and 'Mr. Bailey will see you now'.
She replied, "I have liked you from the first time we met. But I seldom rush into anything of a personal sort. You were always calm and never flustered and most important to me, never rushed or made a move on me. Pushy men do not attract me in the least.
I could sense that you were interested. I could feel your eyes following me when I was near you. I was surprised and delighted when you asked me to dinner last time and our short time together made me think I wanted to be closer to you."
It sounded as if I had made the right move by doing nothing much, and I took it as a warning about what might happen if I rushed things on our return to the room. Our knees touched under the table and I pushed mine between hers. I restrained a groan as the thought of her bare legs and her slit in black panties raced through my mind.
She must have sensed my thoughts, as her eyes were half closed when she whispered, "I am wet and squishy, and I want you."
We rose immediately without further words, only pausing to sign the bill at the counter on the way out. There were others in the elevator, so we could not kiss. But she had her arm through mine and pressed her breast against my upper arm. My hands trembled so much that I could barely get the room card in the slot.
We kissed a wild kiss just inside the room as I pressed her against a wall. I slid my hands down her back desperate to feel her ass. She placed her hands on my shoulders and forced me back a step. "A minute please, let me do what I have been dreaming of doing before you start feeling me."
We moved to the middle of the room and she began to undress me. She was very slow and deliberate, stretching this agonizing play to its limit. She hung each piece of my clothing in the closet before returning for the next article. She pulled my shorts down and gazed at my cock and ran her hand up the bottom of the shaft, then traced a finger around the knob.
Stepping back she pulled her dress over her head to stand there in the black lace bra and panties. Her pretty tits popped out as the bra came off, the nipples jutting out like rosebuds. My heart pounded wildly as she slipped her panties down along her legs to lie in a pool on the floor.
I love women's mounds, and hers bumped out like half an apple covered by a dark crescent shaped bush. The tip of her slit showed through the hairs.
She moved smoothly into my arms, her tits belly and thighs engaging mine. Our mouths met softly, her lips were parted as her tongue tip traced the outline of my lips.
I was overcome with desire, my hands pressed firmly down her back and hips as if trying to absorb her. She trembled as my fingers dug into her ass cheeks pulling and parting them.
My cock was jammed against her hip. I moved it between her legs and felt the knob slide along the wet slit. Her hips swayed back and forth, her wet slit licking the top of my shaft.
She breathed, "Anything you want, take anything you want, I have no rules."
I lifted her slender body up, sliding it along my body until her tits were at my mouth. The nipples were rubber hard as I nuzzled them with my face and nose. I began to suck each one in turn, back and forth, sucking harder and harder each time.
My cock was pressed up along the inside of her thigh. I braced her against the wall; she raised her legs around and behind me opening her wet cunt. I lowered her until the knob was pressing between her legs. She moved her hole to permit it into her slit.
I whispered, "I am going to fuck you."
She said, "So do it."
We began a standing fuck with her back pressed to the wall but I found it too restrictive. I duck walked her across the room with my cock still in her and lay her down cross-wise on the bed. There was no pause for gentle words or kisses, just continuous fucking until we both came. The long build-up ended abruptly with both of us arched into each other, our bodies jerking spasmodically. We lay like that for minutes before I rolled off to my side.
She was smiling at me, "Glad we got that one out of the way."
I said, "That was even better than I have imagined that it would be. You are as beautiful naked as you are dressed." Reaching down I caressed her pussy and said, "I love your pussy."
She rolled to her side facing me and began tracing her fingers around my chest. She threw one leg over mine and snuggled her face into my neck. I was a little afraid that she wanted more immediately. There had been a time when I could get it up back to back, but it had been a few years.
I was having a little problem deciding who this lady really was. I had grown used to viewing her on a pedestal and far above all worldly passions and excesses, but she had just fucked me as hard as I had fucked her and it appeared she wanted more.
She took her time, seemingly content with touching and rubbing on me, applying soft kisses to my neck and chest.
I felt her pussy rubbing on my thigh, her nipples inching upwards towards my mouth. One hand hovered over my bush, teasing the ends of my pubic hairs. My cock began to react and stiffen.
"Hmmm good," she moaned, "I have stirrings here. Let me make it harder." She turned on her knees beside me and bent down over my cock. She stroked it a bit and then circled the knob with her tongue and slowly swallowed a good portion. I arched my back upwards at her, trying to stuff more of it in her mouth. She lifted off of it and turned again to my side.
There was not much of the calm elegant executive secretary remaining. Her hair was matted with moisture, her lips and nipples were red and swollen and her pretty bush sticky with cum.
My cock had found its way between her legs. She reached down and stuffed it in her pussy and moved up over top of me. Leaning over me with her hands braced each side of my head; her tits dangled over my face, her ass began to lift and fall as my cock stiffened enough to fuck. I let her go at her own speed and soon she was driving her hips down hard on me. As soon as she started to cum I rolled her to her back and got off myself.
"Lets have a shower now, we might need it for my next move," she smiled.
We enjoyed a warm shower, rubbing and kissing and soaping each other. She was in full hot mode now. She changed from sweet and gentle to vampy and wicked and back again. I very much enjoyed this other personality of the Iron Maiden.
During the shower she knelt down and took my soft cock into her mouth grazing the knob with her teeth while looking up to read my reaction. There was no lead for the pencil available as yet. I toweled her off first and she went out to the main room pulling a robe around her.
She was on the phone, sitting with her back against the backrest of the bed with her legs stretched out in front of her. She patted the bed inviting me to sit down beside her.
Covering the mouthpiece with her hand she said, "I called my closest friend Gail, you don't mind if we chat for a while do you?"
I smiled at her and opened her robe. What a beautiful body, I could look at it forever. She cupped a breast in her hand, her legs spread just a little.
I leaned in towards her and rubbed my fingertips along each side of her slit. She spread more and slid down a little from the sitting position. I kissed the inside of her knee, and slipped two fingers easily into her pussy. I smiled at her as I finger fucked her.
Elizabeth continued her conversation with her friend as I worked away at her. She was obviously excited about the situation and was slowly sliding down from the pillow as my fingers worked madly away.
I pulled my fingers out and rubbed the juices on her nipples and then licked my fingers. Her eyes went wide as if shocked, but she 'air-kissed' me to confirm that she loved it.
I leaned over Elizabeth and licked the wet nipples, and then began to work my way down her body until my face was buried between her legs. I nuzzled around her swollen pussy, kissing and licking gently.
"Oh God," she groaned, "No, no I am alright, the TV is on and something startled me. No, no, it is not a porno."
By now I had her legs up over my shoulders and was licking and sucking at her pussy. I gradually concentrated more on her swollen hard clit. I toyed with the little hood, flicking it with my tongue. Elizabeth was virtually vibrating, lifting her hips up to rub on my face and moving to present the most pleasurable spot for licking.
I am not sure how she was able to maintain any sort of conversation. It appeared that her friend was the chatty sort with stories to tell because all that came from Elizabeth were 'yes', 'no' and 'is that right?'
I was very excited in this novel attempt at fucking a lady otherwise intent on a phone conversation. I moved around and faced Elizabeth with my legs stretched out towards her and slid mine under hers. We were now facing each other in a sitting position, my cock rubbing the inside of her thigh. Her cunt was swollen and juicy and wide open.
I pushed my knob into her hole and leaned back waiting for her to make her move. I smiled a dare at her and she reacted by pushing her hips at me and taking another inch or so of cock. Her flint hard eyes glared at me as she massaged the end of my cock with her pussy muscles, pinching it just behind the knob.
When she relaxed a bit I continued our game of chicken and jammed a little more into her, and then slow fucked her pussy with part of a cock.
"Well yes, why don't we meet for lunch next week," to her phone friend, gritting her teeth as half my cock moved in and out of her. Her eyes were half closed, heavy with lust, she wanted all my cock now and quite frankly I wanted her to have it.
I jammed the rest of my cock into her and grabbed her ass and pulled her tight against me. Our pubic bones were grinding, her little crescent shaped bush intermingled with mine as she said, "Bye now, oh no, I am alright, will call you tomorrow."
She fumbled to get the receiver back in the cradle, her hips twisting around my cock. I pulled her flat on her back and struggled to get to my knees between her legs. My cock slipped out during the move and she cried out grabbing for it and jamming it back in her wildly thrusting pussy.
I fucked her from my knees, gradually leaning over her until her knees were jammed against my shoulders and my arms under her pulling her to a fetal position as we got off in unison.
"You bad man, taking advantage of me while I was talking on the phone. What an awfully pleasant thing to do."
"I think that you planned that Elizabeth. You wanted me to fuck you. Will you confess to your friend what was happening to you while she was talking?"
"I am not sure. Would you like me to tell her? Should I give her your name?"
"Only if you give her full details, and my phone number."
We laughed together at what we had pulled off.
That was to be the only time Elizabeth and I were to separate our work from pleasure. It had been the most erotic night of my life. When I allow myself to relive that night my cock aches.
Thinking back, it was not the most sensible thing to have done, fucking the Boss's Secretary I mean. It was hardly a prescription for advancement. But I would do it again in a heartbeat.
Elizabeth left the firm a few months after our encounter in the hotel. Another stern efficient woman took her place. I have not yet invited her out to dinner, but I may.