We had gone out of town to check on a branch office that was having problems. Sheila had transferred in to the main office about 3 months earlier. I had worked with her a little but this was the first time we traveled together.
Sheila was in her mid to upper 40s. She had dishwater blonde hair that she wore in a part with the part coming down over one eye. It was short in the back. Her skin looked like it couldn't tolerate sun very well—I suppose it was a result of her freckles.
I liked working with her. She had a good sense of humor, always dressed very classily and was open and friendly. She had lost a little of her humor on this job, though. There were a lot of problems in her area.
We were in her hotel suite going over our notes. It was early evening. I looked at her and noticed her eyes were closed and she was rubbing her head.
"I know something that might help," I said.
I moved my chair behind hers and started to massage her shoulders. Then I moved on to her neck. She really seemed to be enjoying the massage—she almost started to purr. Frankly, I was getting a little turned on, being so close to her and smelling her heady perfume.
She laid her head back and closed her eyes. I decided to take a chance and moved one hand to the top of her blouse. Slowly I slipped it in, rubbing her chest and heading for her breast. I held my breath but she didn't try to stop me.
I grabbed her left breast. It was nice and heavy. She let out a little moan. With that I started to nibble her ear while I cupped her breast in my hand.
Soon I got up and pulled her to her feet. She threw her arms around my neck and we locked in a passionate embrace.
After a few minutes I led her to the bed. She lay down on it while I slowly undressed in front of her. She smiled and licked her lips when I lowered my shorts to reveal my semi-erect cock.
Then it was her turn. I lay on the bed while she undressed for me. Her breasts were big. They swayed back and forth as she removed her skirt and slip. Then she joined me naked on the bed.
We kissed again as she ran her hands over my back and ass. I cupped a breast in each hand and kissed her nipples in turn. Soon she was reaching for my cock. We lay on our sides facing each other. I began to rub my cock along the outside of her pussy—getting her wet.
When I felt we were both ready I rolled on top of her. She was so wet my cock slid right in her hairy pussy. She wrapped her legs around me and we began to fuck slowly so we could enjoy the feeling of my cock going in and out of her cunt.
We fucked like this for about 10 minutes. Then she rolled over to be on top of me. Her tits beat against my chest as she rocked back and forth. She would slide my cock almost all the way out, then reverse and take it deep inside again.
We fucked like this for another 10 or 15 minutes.
"Do me from behind, baby," she said. She got on all fours on the bed. I positioned myself behind her. She had a nice, full ass. With one hand I guided my dick into her cunt. When it was in I grabbed her hips with both hands and began shoving my cock in and out. Her ass was flat against my groin.
I could sense her orgasm coming. I began to fuck her faster and faster. Her pussy was so hot. Finally I couldn't take it any more. With one final thrust I bent over her back. I began kissing her shoulder blade as the cum spurted out of my cock. Before I was done cumming, I positioned my dick against her clit. The feel of my hot, sticky cum hitting her clit pushed her over the edge. She moaned "Ooooooooh" as the orgasm washed over her.
Before the night was over we tried out 6 or 7 other positions. I even took her against the wall in the shower.
Over breakfast in the morning, we came up with several ways we could extend our trip.
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