Dinner with my boss.

Please note that there is no one in the following story under the age of 18.

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It had been the third long day in a row.

Corporate meetings in the dead of winter, it was dark when I got up, and it was dark when the last meetings finished. I am younger than all of the other managers and the only male in a group of twenty-five women, all in their late-fifties and early sixties.

The women had worked together for many years and I felt very much the outsider, and not just because of the age difference. Although I am polite and respectful, I have lots of new ideas and I am not afraid of speaking my mind, which in this very staid group of retail managers, only combines to make me even more unwelcome.

They were friendly and nice enough, but as I sat alone in the hotel restaurant, I knew I just didn't fit in. I was figuring that after having a bite to eat, I would go workout in the weight room and maybe have a swim before heading back to my room and summarizing my meeting notes from today for my staff.

Sitting at a table in the back corner, I was working on those notes, when I heard a voice behind me.

"I thought you would have gone for dinner with the rest of the managers?"

Jean Edwards, my boss. The person who hired me to shake things up.

She was tough, opinionated, and outspoken; but she was fair, and I can't think of a person male or female that I respect more. She is also funny and a good mentor; and although likely more than twenty-five years my senior, she was, very beautiful. She was the subject of many quiet fantasies that had bounced around in my mind during some of the more boring segments of the meetings.

"Hi Jean, I figured you would be out with them too", I said and smiled.

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"I wanted to check to see if anyone was eating alone, and besides, I thought I would skip the gossip-fest."

She added, "They are all nice enough, but they only ever talk about the same things and after two nights of listening to that I am getting a little sick of them."

I smiled again and said "Thanks, I appreciate the company, would you join me?"

"I would love to. I was actually planning on a quick supper and then I wanted to try to get some rest because my neck and back are killing me. These meetings are so stressful with all the head office brass around."

I could see how tense and tight she seemed and I said as much.

"It's nice that you noticed, I appreciate that," she replied with a tired smile.

Before I could say any thing else, the menus arrived and we both ordered and then we talked about the meetings, our opinions of the speakers, her goals, and how difficult it is to inject new ideas to a group of people who didn't want to change.

"I think that is why, I'm sick of listening to them, they don't want to change despite the pressures of the economy. There is so much pressure to adapt and be more flexible."

I laughed and said "Right now, even you don't look very flexible, with your stiff back and neck."

She gave me that tired smile again, "I would love a good massage, with the rest of the week to go, I'm afraid I will be stiff as a board before the end of the week."

The meal arrived, we ate, and talked the entire time. As I listened to her, my appreciation for her only grew stronger, as did my concern for the stress that she was under.

"I am so glad you are here. I know that I can count on you to help turn things around."

When she said that I smiled again, and that made me feel a little bit better about being an outsider.

I decided to take a chance, knowing that the odds were against me, and that I would likely have my offer turned down.

"Jean, why don't you let me see if I could help with your neck and shoulders, I'm worried about you; you look like you are in real pain."

"I wish I could, and I'm grateful for the offer, but could you imagine the gossip; it's bad enough that I'm having dinner with you in a quiet restaurant."

I was surprised at the response; I had figured that I was going to get brushed off or worse. When I didn't, I took another chance.

"Jean, I am pretty good with massaging and I know that I could help, and besides, the place is deserted and nobody will know, do you want to feel like this for the rest of the meetings?"

"Okay, just a short one, after we finish the meal."

Totally, not what I had expected.

Not wanting to seem too excited, I steered the conversation back to dinner and working. I was glad I did, because she told me more stories of the funny things that she had experienced in her different jobs with the company and I could tell she was relaxing a little.

When it came time to leave, she paid the bill with the company credit card and we walked through the empty lobby to the elevator. I was almost afraid she had forgotten her massage.

"What floor are you on? We better use your room because too many of "them" have visited mine."

When she said that, it would have been impossible for her not to see the huge smile on my face.

I told her the floor, she pressed the button, and I forced myself to relax.

The elevator doors opened and the hall was empty. We walked to my room and I swiped the door lock and turned on the room lights.

She asked where I wanted her to be, and wanting to keep her comfortable, I suggested the swivel chair with the low back by the small desk.

First though, I moved the chair to the window so she would be able to look at the lights of the city and she sat down.

As she looked at the lights of the city below, I started to rub her neck.

"Your hands are nice and warm, but a little rough," she said quietly.

I apologized, saying, "Despite working in an office, I do a lot of outside work with my hands."

"Don't apologize, I like how they feel, they feel strong."

I continued to work her neck muscles; I could feel the tension slowly start to ease from her. Moving down a little to the tops of her shoulders, I could not believe how tight they were. Finally, after several minutes though they started to loosen.

I had noticed Jean had closed her eyes.

"MMMMmmmmmmmmmmmm that is so wonderful, I can't remember the last time somebody gave me a massage. "

My hands massaged lower, but I was stopped by the back of the chair.

"Would you like to me try your lower back as well?"

She nodded, and without me asking, she got up and lay face down on the bed.

Not wanting to press much my luck too much, I massaged her back through her clothes. It wasn't as effective, but I wanted her to feel comfortable.

Standing beside the bed wasn't the best way either, but my hands worked her back and she responded with further light moans and smiles. Her eyes were closed again.

In a quiet voice she asked, "Do you have any oil?"

"In the bathroom I have some, I'll go and grab it."

"Good, would you get it and bring two towels to protect the bed?"

I left the room to get them and when I returned.

Jean was standing up and said, "Okay, before I let you massage me anymore, you have to promise not to say a word to anyone, not ever, and if you do, I will fire your tight little ass?

"Jean, I would never breathe a word about this to anyone, I promise."

"Okay, close your eyes for a minute and I will tell you when you can open them, I don't want to get any oil on my clothes."

Closing my eyes, I imagined her undressing.

I could hear, the sound of her pulling her sweater over her head, the faint sounds of her bra clasp coming undone and the little sign of relief that accompanied the freeing of her boobs, the sounds of her shoes coming off, and the soft sounds of her slacks and panties falling on the floor.

Then I heard the sound of one towel being placed on the bed, then the quiet sound of her wrapping the smaller towel around herself and then of her lying back down on the bed.

"Okay, I'm ready."

"Jean, I am going to make you feel so much better, you already look so much more relaxed."

She closed her eyes again and murmured something I couldn't hear as I rubbed the baby oil on my hands and started again at her neck and shoulders.

I moved down her back and as I did, she repositioned the towel so that it only covered her nice ass.

"Jean, I don't know if anyone has told you today, what a beautiful woman you are?"

She laughed, "I am old enough to be your mother"

"That doesn't change anything, you are so beautiful", I said.

She smiled and closed her eyes again.

As I massaged her lower back, my fingers approached the edge of the towel and briefly slipped underneath the edges. My heart was beating faster and faster and the bulge in my pants was also starting to become more noticeable.

Taking a deep breath, I straightened up and then I started massaging her feet.

She didn't object, simply saying quietly "That feels so nice, please don't stop."

I massaged each toe, then the arch of her foot, her heel, and started on her calves. The oil helped and she let out a series of light moans and kept her eyes closed.

Moving up her thighs, I worked her muscles and noticed that ever so slightly she opened her legs just a tiny bit. My hands moved up under the towel slightly and slightly brushed against her pussy.

There was no resistance, only a slight widening of her legs a little more. Under the towel, I ran a bold finger from her pussy up her ass.

Her breath became a little more rapid and she stiffened slightly, but she said nothing.

I heard a small sigh as I stopped and turned my attention to her other foot and repeated the same massage.

Pausing at her calf, I stopped and removed my tie, slowly undoing it and the buttons on my shirt. Jean turned, watched, and smiled as I took off my shirt and undid my belt. I slid down my dress pants and socks. When I removed my underwear, Jean smiled and laid back onto her stomach.

"Your hands feel so wonder, I can't wait for you to continue."

Approaching the towel again, my hands moved under it and I could feel her tense again and then relax as my fingers moved, working every inch of her. I pulled the towel away and poured a little oil onto her ass.

"Don't stop," was the whisper that came from her mouth as the oil dripped into the space between her cheeks.

I climbed up onto the bed and straddled her legs.

My strong hands were now kneading her ass as I rubbed the oil into her cheeks. Taking a finger, I traced the passage from her pussy to her rosebud. She inhaled sharply and I felt her body tense as her first small orgasm happened. She lifted her ass up to meet my fingers and one set of fingers worked her pussy, moving gently around her outer lips and then into the small inner folds and then to the little nub of her clit.

My other fingers were rimming her beautiful ass, rounding the edges and then pushing in slightly. The oil provided the key and as my fingers penetrated her; as a second, more powerful orgasm struck her.

Her moan started small and rose to almost a scream as her body arched and shivered from the intensity of the climax. As she slowly began to breathe normally, I bent down and holding her cheeks apart, licked her beautiful asshole. My tongue circled the rim and probed forcefully at the tight opening.

She turned over and pulled my face to her lips and we kissed deeply for several minutes.

"I've seen how you've been looking at me during the meetings, I've wanted to get you alone since we got here, but I didn't expect this," she smiled and said quietly.

It was my turn to smile.

I moved down and my lips found her nipples, using one hand to lightly stroke one breast while my lips and tongue alternated lightly sucking and then slowly biting on the other. Her eyes closed again and she lightly moaned while I made love with my tongue to her breasts.

My fingers tips made lots of small slow circles and then larger ones on her flat tummy.

"That feels so amazing" she whispered.

Moving back up to her face, we kissed again and again, our tongues exploring every inch of each other's mouths.

"Now I need to finish your massage," and I kissed my way down to between her legs.

My tongue and face made contact with her well trimmed little box, starting from the outside and working towards her little clit. I circled her folds with my tongue and then used my whole mouth to devour her beautiful pussy.

"Suck my little clitty," came in a ragged whisper, and I did as she asked.

My hands and fingers had not forgotten their part. All the while I had been running my hands over her body. Using my fingers to massage the little space between her pussy and her ass, the effect was driving her closer to the edge. One then two fingers re-penetrated her ass, first just the tips, then to the first joint, and then slowly working her ass in and out.

Her back arched and her body went rigid as her legs clamped around me and she shook uncontrollably for what seemed like forever and she screamed as loud as I had ever heard anyone in a hotel room.

All of the stress and the strain of the last few days was gone, and I moved up beside her and held her tight in my arms.

We lay together, both drenched in baby oil and sweat.

Then she moved up and straddled my legs, looking so amazingly beautiful. She moved herself to directly over my hard cock and then slowly impaled herself on it, inch by inch. Our bodies now joined at the hips, we rocked back and forth, in and out as she took control.

Leaning forward she lowered her chest to my mouth, as her hips rocked with me deep inside her.

I took one nipple into my mouth and suckled her rock-hard nipple, and then after sucking and gently biting them, switched to the second one.

After everything that we had done, it did not take long for me to feel the pressure building.

"I'm going to cum."

"Come inside me, I want you to fill my pussy, I want to feel you letting go inside me."

A second or two later I came and I came, filling her sweet pussy.

I felt her pull herself off me and she moved up my chest and brought her dripping pussy to my mouth.

I tasted the combination of cum and her juices, and cleaned her now puffy red pussy inside and out. She moaned loudly again, and her body was wracked by another orgasm and then she collapsed onto my body.

Kissing me deeply and licking the cum from my face, she smiled at me.

"That was an incredible massage."

We pulled back the blanket and the towels and climbed between the sheets.

We lay together, just holding each other in our arms and at some point, we fell asleep.

When the alarm woke me up, she was gone. A little note was on the bed and it said ...

"Good morning, you give amazing massages, my neck and shoulders feel so much better, tonight let's skip the supper and I will come to your room and give you a massage ... Jean"